CA2031472A1 - Thermoplastic resin composition - Google Patents
Thermoplastic resin compositionInfo
- Publication number
- CA2031472A1 CA2031472A1 CA002031472A CA2031472A CA2031472A1 CA 2031472 A1 CA2031472 A1 CA 2031472A1 CA 002031472 A CA002031472 A CA 002031472A CA 2031472 A CA2031472 A CA 2031472A CA 2031472 A1 CA2031472 A1 CA 2031472A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- polyamide
- acid
- weight
- resin composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 33
- 229920005992 thermoplastic resin Polymers 0.000 title claims abstract description 7
- -1 alkenyl aromatic compound Chemical class 0.000 claims abstract description 56
- 239000004952 Polyamide Substances 0.000 claims abstract description 54
- 150000001875 compounds Chemical class 0.000 claims abstract description 52
- 229920002647 polyamide Polymers 0.000 claims abstract description 52
- 239000002253 acid Substances 0.000 claims abstract description 45
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 42
- 229920001955 polyphenylene ether Polymers 0.000 claims abstract description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 16
- 150000001412 amines Chemical class 0.000 claims abstract description 16
- 229920000642 polymer Polymers 0.000 claims abstract description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
- 229920005604 random copolymer Polymers 0.000 claims abstract description 9
- 230000005494 condensation Effects 0.000 claims abstract description 8
- 229920001519 homopolymer Polymers 0.000 claims abstract description 8
- 230000009257 reactivity Effects 0.000 claims abstract description 8
- 238000007363 ring formation reaction Methods 0.000 claims abstract description 8
- 238000007142 ring opening reaction Methods 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims description 31
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 23
- 229920001577 copolymer Polymers 0.000 claims description 20
- 229920002292 Nylon 6 Polymers 0.000 claims description 16
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 229920002302 Nylon 6,6 Polymers 0.000 claims description 11
- 125000000524 functional group Chemical group 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 238000004898 kneading Methods 0.000 claims description 10
- 150000003951 lactams Chemical class 0.000 claims description 9
- 150000001993 dienes Chemical class 0.000 claims description 8
- 239000011256 inorganic filler Substances 0.000 claims description 8
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 8
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 229920000877 Melamine resin Polymers 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 7
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000004760 aramid Substances 0.000 claims description 6
- 229920003235 aromatic polyamide Polymers 0.000 claims description 6
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 6
- 229920006177 crystalline aliphatic polyamide Polymers 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 239000004593 Epoxy Substances 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical group NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 4
- 229920003189 Nylon 4,6 Polymers 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229920000098 polyolefin Polymers 0.000 claims description 4
- 239000001993 wax Substances 0.000 claims description 4
- 229920000299 Nylon 12 Polymers 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 150000001244 carboxylic acid anhydrides Chemical group 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- 239000003365 glass fiber Substances 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 150000004053 quinones Chemical class 0.000 claims description 3
- 150000004756 silanes Chemical class 0.000 claims description 3
- 239000000454 talc Substances 0.000 claims description 3
- 229910052623 talc Inorganic materials 0.000 claims description 3
- 229920000571 Nylon 11 Polymers 0.000 claims description 2
- 229920000265 Polyparaphenylene Polymers 0.000 claims description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004018 acid anhydride group Chemical group 0.000 claims description 2
- 239000004927 clay Substances 0.000 claims description 2
- 229910052570 clay Inorganic materials 0.000 claims description 2
- NJLLQSBAHIKGKF-UHFFFAOYSA-N dipotassium dioxido(oxo)titanium Chemical compound [K+].[K+].[O-][Ti]([O-])=O NJLLQSBAHIKGKF-UHFFFAOYSA-N 0.000 claims description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical group O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 2
- 239000000347 magnesium hydroxide Substances 0.000 claims description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 2
- 239000004953 Aliphatic polyamide Substances 0.000 claims 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims 1
- 229920003231 aliphatic polyamide Polymers 0.000 claims 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims 1
- 230000000295 complement effect Effects 0.000 claims 1
- 125000005462 imide group Chemical group 0.000 claims 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 claims 1
- 229920001169 thermoplastic Polymers 0.000 abstract description 5
- 239000004416 thermosoftening plastic Substances 0.000 abstract description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 20
- 229920002943 EPDM rubber Polymers 0.000 description 16
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 239000001530 fumaric acid Substances 0.000 description 10
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 239000004677 Nylon Substances 0.000 description 9
- 150000004985 diamines Chemical class 0.000 description 9
- 229920001778 nylon Polymers 0.000 description 9
- PBLZLIFKVPJDCO-UHFFFAOYSA-N 12-aminododecanoic acid Chemical compound NCCCCCCCCCCCC(O)=O PBLZLIFKVPJDCO-UHFFFAOYSA-N 0.000 description 8
- 150000001408 amides Chemical class 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 229920001971 elastomer Polymers 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 239000005060 rubber Substances 0.000 description 7
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 6
- 229920000181 Ethylene propylene rubber Polymers 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 6
- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 229920001935 styrene-ethylene-butadiene-styrene Polymers 0.000 description 5
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000001746 injection moulding Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 3
- DPQHRXRAZHNGRU-UHFFFAOYSA-N 2,4,4-trimethylhexane-1,6-diamine Chemical compound NCC(C)CC(C)(C)CCN DPQHRXRAZHNGRU-UHFFFAOYSA-N 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 description 3
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 3
- 229920000298 Cellophane Polymers 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 229920002633 Kraton (polymer) Polymers 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- 239000005062 Polybutadiene Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
- 229920000578 graft copolymer Polymers 0.000 description 3
- 150000004820 halides Chemical group 0.000 description 3
- 150000003949 imides Chemical class 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 239000001630 malic acid Substances 0.000 description 3
- 235000011090 malic acid Nutrition 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229920006131 poly(hexamethylene isophthalamide-co-terephthalamide) Polymers 0.000 description 3
- 229920002857 polybutadiene Polymers 0.000 description 3
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229920000638 styrene acrylonitrile Polymers 0.000 description 3
- 229920001897 terpolymer Polymers 0.000 description 3
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- QQOMQLYQAXGHSU-UHFFFAOYSA-N 2,3,6-Trimethylphenol Chemical compound CC1=CC=C(C)C(O)=C1C QQOMQLYQAXGHSU-UHFFFAOYSA-N 0.000 description 2
- WSWCOQWTEOXDQX-UHFFFAOYSA-N 2,4-Hexadienoic acid Chemical compound CC=CC=CC(O)=O WSWCOQWTEOXDQX-UHFFFAOYSA-N 0.000 description 2
- ATGFTMUSEPZNJD-UHFFFAOYSA-N 2,6-diphenylphenol Chemical compound OC1=C(C=2C=CC=CC=2)C=CC=C1C1=CC=CC=C1 ATGFTMUSEPZNJD-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- TYKJILJOXAHUFO-UHFFFAOYSA-N 2-amino-1,4-dihydroimidazol-5-one Chemical compound NC1=NC(=O)CN1 TYKJILJOXAHUFO-UHFFFAOYSA-N 0.000 description 2
- HZLCGUXUOFWCCN-UHFFFAOYSA-N 2-hydroxynonadecane-1,2,3-tricarboxylic acid Chemical compound CCCCCCCCCCCCCCCCC(C(O)=O)C(O)(C(O)=O)CC(O)=O HZLCGUXUOFWCCN-UHFFFAOYSA-N 0.000 description 2
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 2
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 2
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 2
- IGSBHTZEJMPDSZ-UHFFFAOYSA-N 4-[(4-amino-3-methylcyclohexyl)methyl]-2-methylcyclohexan-1-amine Chemical compound C1CC(N)C(C)CC1CC1CC(C)C(N)CC1 IGSBHTZEJMPDSZ-UHFFFAOYSA-N 0.000 description 2
- DEFCWQPPZCNKIQ-UHFFFAOYSA-N 4-[(4-amino-3-methylcyclohexyl)methyl]-2-methylcyclohexan-1-amine;benzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1.C1CC(N)C(C)CC1CC1CC(C)C(N)CC1 DEFCWQPPZCNKIQ-UHFFFAOYSA-N 0.000 description 2
- IMAJIPBIVGZIET-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine;benzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1.C1CC(N)CCC1CC1CCC(N)CC1 IMAJIPBIVGZIET-UHFFFAOYSA-N 0.000 description 2
- BDBZTOMUANOKRT-UHFFFAOYSA-N 4-[2-(4-aminocyclohexyl)propan-2-yl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1C(C)(C)C1CCC(N)CC1 BDBZTOMUANOKRT-UHFFFAOYSA-N 0.000 description 2
- CSVBIURHUGXNCS-UHFFFAOYSA-N 6-azaniumylhexylazanium;terephthalate Chemical compound NCCCCCCN.OC(=O)C1=CC=C(C(O)=O)C=C1 CSVBIURHUGXNCS-UHFFFAOYSA-N 0.000 description 2
- CIRRFAQIWQFQSS-UHFFFAOYSA-N 6-ethyl-o-cresol Chemical compound CCC1=CC=CC(C)=C1O CIRRFAQIWQFQSS-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- GVNWZKBFMFUVNX-UHFFFAOYSA-N Adipamide Chemical compound NC(=O)CCCCC(N)=O GVNWZKBFMFUVNX-UHFFFAOYSA-N 0.000 description 2
- UIERETOOQGIECD-UHFFFAOYSA-N Angelic acid Natural products CC=C(C)C(O)=O UIERETOOQGIECD-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229920000305 Nylon 6,10 Polymers 0.000 description 2
- 229920005647 Nylon TMDT Polymers 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- MBHRHUJRKGNOKX-UHFFFAOYSA-N [(4,6-diamino-1,3,5-triazin-2-yl)amino]methanol Chemical class NC1=NC(N)=NC(NCO)=N1 MBHRHUJRKGNOKX-UHFFFAOYSA-N 0.000 description 2
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- SECPZKHBENQXJG-BQYQJAHWSA-N palmitelaidic acid Chemical compound CCCCCC\C=C\CCCCCCCC(O)=O SECPZKHBENQXJG-BQYQJAHWSA-N 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- LQAVWYMTUMSFBE-UHFFFAOYSA-N pent-4-en-1-ol Chemical compound OCCCC=C LQAVWYMTUMSFBE-UHFFFAOYSA-N 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-N pent-4-enoic acid Chemical compound OC(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-N 0.000 description 1
- ICMWSAALRSINTC-UHFFFAOYSA-N penta-1,4-dien-3-ol Chemical compound C=CC(O)C=C ICMWSAALRSINTC-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920000314 poly p-methyl styrene Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920006123 polyhexamethylene isophthalamide Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920013636 polyphenyl ether polymer Polymers 0.000 description 1
- 229920000346 polystyrene-polyisoprene block-polystyrene Polymers 0.000 description 1
- 229920002102 polyvinyl toluene Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- 125000004151 quinonyl group Chemical group 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 238000003385 ring cleavage reaction Methods 0.000 description 1
- 235000019512 sardine Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- WQDUMFSSJAZKTM-UHFFFAOYSA-N sodium methoxide Substances [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
- UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- HMFPLNNQWZGXAH-OCOZRVBESA-N trans-2-hexacosenoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCC\C=C\C(O)=O HMFPLNNQWZGXAH-OCOZRVBESA-N 0.000 description 1
- XKZKQTCECFWKBN-UHFFFAOYSA-N trans-4-decenoic acid Natural products CCCCCC=CCCC(O)=O XKZKQTCECFWKBN-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- ZHYZQXUYZJNEHD-UHFFFAOYSA-N trans-geranic acid Natural products CC(C)=CCCC(C)=CC(O)=O ZHYZQXUYZJNEHD-UHFFFAOYSA-N 0.000 description 1
- UIUWNILCHFBLEQ-NSCUHMNNSA-N trans-pent-3-enoic acid Chemical compound C\C=C\CC(O)=O UIUWNILCHFBLEQ-NSCUHMNNSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- AMJYHMCHKZQLAY-UHFFFAOYSA-N tris(2-isocyanatophenoxy)-sulfanylidene-$l^{5}-phosphane Chemical compound O=C=NC1=CC=CC=C1OP(=S)(OC=1C(=CC=CC=1)N=C=O)OC1=CC=CC=C1N=C=O AMJYHMCHKZQLAY-UHFFFAOYSA-N 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
- 229960002703 undecylenic acid Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
- C08L71/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
- C08L71/12—Polyphenylene oxides
- C08L71/123—Polyphenylene oxides not modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/315—Compounds containing carbon-to-nitrogen triple bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
- C08K5/34922—Melamine; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S525/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S525/905—Polyphenylene oxide
Abstract
ABSTRACT
THERMOPLASTIC RESIN COMPOSITION
The present invention provides a thermo-plastic resin composition which comprises:
(i) at least one compatibilizing agent in an amount effective for compatibilization, (ii) (A) a polyphenylene ether in an amount of about 40 - 100 % by weight based on the total amount of (A) and (B) and (B) a homopolymer of alkenyl aromatic compound or a random copolymer of alkenyl aromatic compound and unsaturated compound in an amount of 0-about 60 % by weight based on the total amount of (A) and (B), the total amount of (A) and (B) being about 10 % by weight or more based on total amount of all polymer components, (iii) at least one polyamide in an amount more than the amount required for forming a continuous phase, and (iv) a compound having a molecular weight of 2,000 or less, containing nitrogen element, and having ring opening or condensation polymerizability or reactivity with acid or amine.
THERMOPLASTIC RESIN COMPOSITION
The present invention provides a thermo-plastic resin composition which comprises:
(i) at least one compatibilizing agent in an amount effective for compatibilization, (ii) (A) a polyphenylene ether in an amount of about 40 - 100 % by weight based on the total amount of (A) and (B) and (B) a homopolymer of alkenyl aromatic compound or a random copolymer of alkenyl aromatic compound and unsaturated compound in an amount of 0-about 60 % by weight based on the total amount of (A) and (B), the total amount of (A) and (B) being about 10 % by weight or more based on total amount of all polymer components, (iii) at least one polyamide in an amount more than the amount required for forming a continuous phase, and (iv) a compound having a molecular weight of 2,000 or less, containing nitrogen element, and having ring opening or condensation polymerizability or reactivity with acid or amine.
Description
2031~7~
T~IERMOPLASTIC RESIN COMPOSITION
The present invention relates -to a thermo-plastic resin composition which can be suitably utilized as three-dimensional shaped articles, sheets and the like, especially automobile parts and electric par-ts made by injection molding, extrusion molding and blow molding.
More particularly, the present invention relates to a novel thermoplastic resin composition excellent in processability and paintability which comprises at least one compatibilizing agent, a polyphenylene ether, at least one polyamide resin, and a reactive compound having a molecular weight of 2,000 or less and containing nitrogen element and, as optional components, an inorganic filler and an impact strength improver.
Resin compositions comprising polyphenylene ether and polyamide have been known for a long time and a composition comprising polyphenylene ether and at most 25 ~ by weight of polyamide is disclosed in U.S. Patent No. 3,379,792, but no compatibilizing agents for compatibilizing polyphenylene ether and polyamide are disclosed therein.
A liquid diene polymer, an epoxy compound and a compound having in the molecule both la) carbon-carbon double bond or carbon-carbon triple bond and (b) carboxylic acid, acid anhydride, acid amide, imide, carboxylate ester, amino or hydroxyl group are disclosed as compatibilizing agents in U.S. Patent No. 4,315,086. This patent further discloses as impact strength improvers ethylene .
,:
:'~
propylene rubber, ethylene propylene polyene rubber or unsaturated carboxylic acid-modified products of these rubbers, SBR, polybutadiene, polystyrene-diene rubber diblock or triblock copolymers or compositions with par-tial hydrides of these copolymers.
Processes for obtaining compositions by grafting unsaturated carboxylic acids on polyphenylene ether in the presence or absence of radical initiators and mixing the resulting graft polymer with poly-amides are disclosed in Japanese Patent Kokai Nos.
59-59724 and 59-86653, U.S. Patent No. 4,654,405 and International Patent Publication WO 87/00540.
Alkenyl aromatic compounds and ~,~ un-saturated dicarboxylic acid anhydridesor their imide compounds are disclosed as compatibilizing agents for polyphenylene ether and polyamide in European Patent Publication EP-0046040.
Aliphatic polycarboxylic acids such as malic acid are disclosed in International Patent Publication WO 85/05372, oxidized polyethylene waxes are disclosed in U.S. Patent No. 4,659,760, quinones are disclosed in U.S. Patent No. 4,659,763, polyphenylene ethers made functional by epoxy compounds are disclosed in U.S. Patent No. 4,732,937, and polyfunctional compounds comprising anhydrotrimellitic acid chloride are disclosed in U.S. Patent No. 4,600,741 as compatibilizing agents for polyphenylene ether and polyamide. All of these compounds can be used in the present invention as compatibilizing agents.
Compositions comprising combination of compatibilizing agent, polyphenylene ether and crystalline polyamide with non-crystalline polyamide 2031~7~
~re disclosed in Japanese Patent Kokai Nos. 63-108060 and 63-113071 and International Patent Publication W~ 88/06173.
Fur-thermore, compositions containing nitrogen-containing heterocyclic compounds or melamine as flame retardants are known in Japanese Patent Kokai Nos. 62-236853 and 1-139642. However, resin compositions superior in paintability and other properties have not yet been developed.
Polyphenylene compositions have excellent mechanical properties and heat resistance, but have the defect that they are susceptible to discoloration when exposed to ultraviolet rays and sunlight. This defect is conspicuous especially in compositions comprising polyamide and polyphenylene ether and in general, molded articles of these compositions are painted for solving the defect or imparting decorative beautiful appearance and so compositions excellent in adhesion to coating have been demanded. However, conventional compositions comprising compatibilizing agent, polyphenylene ether and polyamide are not necessarily satisfactory in adhesion to coating and improvement of adhesion has been desired.
As a result of intensive research on various components conducted by the inventors, it has been found that compositions comprising a compatibilizing agent, polyphenylene ether and polyamide are markedly improved without damaging the excellent mechanical properties of the compositions by adding a small amount of a compound which has a molecular weight of 2,000 or less, contains nitrogen element and has ring opening or condensation polymerizability or has reactivity with acid or amine. Thus, the present 203~ ~7~
invention has been accomplished.
Tha-t is, the present invention is a thermo-plastic resin composition which comprises:
(i) at least one compatibilizing agent in an amount effective for compa-tibilization, (ii) (A) a polyphenylene ether in an amount of about 40 - 100 % by weight based on the total amount of (A) and (B) and (B) a homopolymer of alkenyl aromatic compound or a random copolymer of alkenyl aromatic compound and unsaturated compound in an amount of 0-about 60 % by weight based on the total amount of (A) and (B), the total amount of (A) and (B) being about 10 % by weight or more based on total amount of all polymer components, (iii) at least one polyamide in an amount more than the amount required for forming a continuous phase, and ~iv) a compound having a molecular weight of 2,000 or less, containing nitrogen element, and having ring opening or condensation polymeri-zability or reactivity with acid or amine.
The polyphenylene ether (ii) (A) is a polymer obtained by oxidation polymerization of at least one phenol compound represented by the formula:
- s - 203147~
0~1 R I R
`,~
(wherein Rl, R2, R3, R4 and R which may be identical or different each represents a hydrogen atom, a hologen atom, a hydrocarbon group or a substituted hydro-carbon group and at least one of them is a hydrogen atom) with oxygen or a gas containing oxygen using an oxidation coupling catalyst.
Examples of R , R , R , R and R in the above formula are hydrogen atom, halogen atoms such as chlorine, fluorine, bromine, and iodine, and hydrocarbon groups or substituted hydrocarbon groups of 1 - 18 carbon atoms, for example, alkyl groups or substituted alkyl groups such as methyl, ethyl, n-propyl, iscpropyl, pri-, sec- or t-butyl, chloroethyl, hydroxyethyl, phenylethyl, hydroxymethyl, carboxyethyl, methoxycarbonylethyl, and cyanoethyl, aryl groups or substituted aryl groups such as phenyl, chlorophenyl, methylphenyl, dimethylphenyl, and ethylphenyl, benzyl group and allyl group.
Examples of the phenol compounds shown by the above formula are phenol, o-, m- or p-cresol, 2,6-, 2,5-, 2,4- or 3,5-dimethylphenol, 2-methyl-6-phenylphenol, 2,6-diphenylphenol, 2,6-diethylphenol, 2-methyl-6-ethylphenol, and 2,3,5 ,2,3,6-, or 2,4,6-trimethylphenol, 3-methyl-6-t-butylphenol, thymol, and 2-methyl-6-allylphenol. Further, the phenol compounds may be copolymers of the compounds of the above formula and other phenol compounds, for - 6 - 203147~
example, polyhydric hydroxy aromatic compounds such as bisphenol A, tetrabromobisphenol A, resorcin, hydroquinone, and novolak resins.
Among them, preferred are homopolymers of 2,6-dimethylphenol or 2,6-diphenylphenol or copolymers of major part of 2,6-dimethylphenol and minor part of 3-methyl-6-t-butylphenol or 2,3,6-trimethylphenol.
Any oxidation coupling catalysts can be used for oxidation polymerization of the phenol com-pounds as far as they have polymerization ability.
Typical examples thereof are catalysts comprising cuprous salt and tert. amine such as cuprous chloride-triethylamine and cuprous chloride-pyridine;
catalysts comprising cupric salt-amine and alkali metal hydroxide such as cupric chloride-pyridine-potassium hydroxide; catalysts comprising manganese salt and primary amine such as manganese chloride-ethanolamine and manganese acetate-ethylenediamine;
catalysts comprising manganese salt and alcoholate or phenolate such as manganese chloride-sodium methylate and manganese chloride-sodium phenolate;
catalysts comprising cobalt salt and tert. amine.
Oxidation polymerization temperature for obtaining polyphenylene ether is 40C or higher (high temperature polymerization) or lower (low temperature polymerization). Either temperature may be used, although polymers produced thereby have different properties.
At least one polyamide (iii) used in the present invention is at least one polyamide selected from crystalline aliphatic polyamides and aromatic polyamides.
The crystalline aliphatic polyamides used in the present invention include, for example, the following.
They have a molecular weight of 10,000 or more and can be produced by bonding equimolar of a saturated aliphatic dicarboxylic acid containing 4 -12 carbon atoms and an alipha-tic diamine containing 2 - 12 carbon atoms. In this case, if necessary, the diamine may be used so as to provide more amine terminal groups than carboxyl terminal groups in the polyamide, or alternatively, a dibasic acid may be used so as to provide more acid groups. Similarly, these polyamides can be produced from the above acid and acid production derivatives and amine production derivatives such as esters, acid chlorides and amine salts of the above mentioned acids and amines.
Typical examples of the aliphatic di-carboxylic acids used for production of the polyamides include adipic acid, pimelic acid, azelaic acid, suberic acid, sebacic acid and dodecanedioic acid. Typical examples of the aliphatic diamines include hexamethylenediamine and octamethylenediamine.
Besides, these polyamides can also be produced by self-condensation of lactam.
Examples of the polyamides are polyhexamethyl-ene adipamide (nylon 66), polyhexamaethylene azelamide (nylon 69), polyhexamethylene sebacamide (nylon 610), polyhexamethylene dodecanoamide (nylon 612), poly-bis-(p-aminocyclohexyl)methane dodecanoamide, polytetramethylene adipamide (nylon 46) and polyamides 203147~
produced by ring cleavage of lactam such as polycapro-lactam (nylon 6) and polylauryl lactam. Furthermore, there may be used polyamides produced by polymeri-zation of at least two amines or acids used for production of -the above-mentioned polymers, for example, polymers produced from adipic acid, sebacic acid and hexamethylenediamine. The polyamides further include blends of polyamides such as a blend of nylon 66 and nylon 6 including copolymers such as nylon 66/6.
Preferably, these crystalline polyamides used in the present invention are nylon 46, nylon 6, nylon 66, nylon 11 and nylon 12. More preferred are nylon 6, nylon 66 and blends of nylon 66 and nylon 6 at optional blending ratio.
Furthermore, those which have terminal functional groups excess in amine terminal groups, excess in carboxyl terminal groups or balanced in these groups, or mixtures of them at optional ratio can be suitably used.
The aromatic polyamides used in the present invention are copolyamides containing an aromatic component therein, for example, polyhexamethylene isophthalamide (nylon 6I). The thermoplastic copolyamides containing aromatic component means melt-polymerizable polyamides containing as a main component an aromatic amine acid and~or an aromatic dicarboxylic acid such as para-aminoethylbenzoic acid, para-aminoethylbenzoic acid, terephthalic acid, and isophthalic acid.
Diamines which may constitute another component of the polyamide include hexamethylene-2~3~ 47~
diamine, undecamethylenediamine, dodecamethylene-diamine, 2,2,4-/2,4,4-trimethylhexamethylenediamine, m-xylylenediamine, p-xylylenediamine, bis(p-amino-cyclohexyl)methane, bis(p-aminocyclohexyl)propane, bis(3-methyl-4-aminocyclohexyl)methane, 1,3-bis(amino-methyl)cyclohexane, and 1,4-bis(aminomethyl)cyclohexane.
An isocyanate may also be used in place of the diamine.
Examples of the isocyanate are 4,4'-diphenylmethane diisocyanate and tolylene diisocyanate.
Comonomers which are used, if necessary, have no limitation and examples of the comonomers are a unit of lactam, a unit of ~-amino acid of 4 - 12 carbon atoms, a compound derived from an aliphatic dicarboxylic acid of 4 - 12 carbon atoms and an aliphatic diamine of 2 - 12 carbon atoms, for example, lactams and amino acids such as ~-caprolactam, w-laurolactam, ll-aminoundecanoic acid, and 12-aminododecanoic acid, and equimolar salts of the above-mentioned various diamines and adipic acid, azelaic acid or sebacic acid.
Typical example of the thermoplastic aromaticcopolyamidescomprising these component~ are copolymer polyamide of p-aminomethylbenzoic acid and ~-caprolactam (nylon AMBA/6), polyamides mainly composed of 2,2,4-/2,4,4-trimethylhexamethylene-diamine terephthalate (nylon TMDT and Nylon TMDT/6I), polyamide mainly composed of hexamethylene diamine isophthalate and/or hexamethylenediamine terephthalate and containing, as a comonomer, bis(p-aminocyclo-hexyl)methane isophthalate and/or bis(p-aminocyclohexyl) methane terephthalate, bis(3-methyl-4-aminocyclo-hexyl)methane isophthalate and/or bis(3-methyl-4-amino-cyclohexyl)methane terephthalate or bis(p-amino-cyclohexyl)propane isophthalate and/or 20~47~
bis(p-aminocyclohexyl)propane terephthalate (nylon 6I/PACM I, nylon 6I/DMPACM I, nylon 6I/PACP I, nylon 6I/6T/PACM I/PACM T, nylon 6I/6T/
DMPACM I/DMPACM T, nylon 6I/6T/PACP I/PACP T), polyamide mainly composed of hexamethylenediamine-isophthalate or hexamethylenediamine terephthalate and containing, as a comonomer, ~-caprolactam, 12-aminododecanoic acid, hexamethylenediamine adipate, bis(p-aminocyclohexyl)methane adipate or bis(3-methyl,4-amlnocyclohexyl)methane adipate (nylon 6I, 6I/6T, 6I/12,6T/6, 6T/66, 6I/PACM 6, 6I/DMPACM 6), and polyamides mainly composed of bis(p-aminocyclo-hexyl)methane isophthalate or bis(3-methyl,4-amino-cyclohexyl)methane-isophthalate and containing, as a comonomer, hexamethylenediamine dodecanedioate or 12-aminododecanoic acid (nylon PACM I/612, nylon DMPACM I/12).
Of these aromatic polyamides, non-crystalline aromatic polyamides are suitable.
Compounds (iv) used in the present inventionwhich have a molecular weight of 2,000 or less, contain nitrogen atom and have ring opening or condensation polymerizability or reactivity with acid amine are those of the following group.
(a) Lactams and derivatives thereof (b) Diamines and derivatives thereof (c) Diisocyanates and derivatives thereof (d) Triazines and derivatives thereof Examples of the compounds are shown below.
(a) Lactams and derivatives thereof:
203~472 11 .
Lactams such as ~-cap:rolactam, ~-laurolactam, ll-aminoundecanoic acid, 12-aminododecanoic acid, glycocyamidine, oxindol, isatin, and cyclic ureide, and derivatives thereof such as low molecular weight oligomers and metallic salts thereof.
(b) Diamines and derivatives thereof:
Diamlnes such as hexamethylenediamine, undecamethylenediamine, dodecamethylenediamine, 2,2,4-/
2,4,4-trimethylhexamethylenediamine, m-xylylenediamine, p-xy~ylenediamine, bis(p-aminocyclohexyl)methane, bis(p-aminocyclohexyl)propane, bis(3-methyl,4-amino-cyclohexyl)methane, 1,3-bis(aminomethyl)cyclohexane, and 1,4-bis(aminomethyl)cyclohexane, and derivatives thereof such as salts of these diamines with dicarboxylic acids.
(c) Diisocyanates and derivatives thereof:
Tolylene diisocyanate, diphenylmethane diisocyanate and polymers thereof, naphthalene diiso-cianate, tolidine diisocyanate, triphenylmethane triisocyanate, tris(isocyanatophenyl) thiophosphate, p-phenylene diisocyanate, hexamethylene diisocyanate, xylylene diisocyanate, isophorone diisocyanate, bis(isocyanatomethyl)cyclohexane, dicyclohexylmethane diisocyanate, lysine diisocyanate, trimethylhexa-methylene diisocyanate, 2-chloroethyl isocyanate, chloroacetyl isocyanate, 4-chlorobenzenesulfonyl isocyanate, 3,4-dichlorophenyl isocyanate, 2-isocyanatobenzoyl chloride, chlorosulfonyl isocyanate, N-(chlorocarbonyl) isocyanate, 2,4-difluorophenyl isocyanate, 4-fluoro-3-nitrophenyl isocyanate, 2-fluorophenyl isocyanate, 2-chlorophenyl isocyanate, 3-fluorophenyl isocyanate, 3-chlorophenyl isocyanate, 2031~7~
T~IERMOPLASTIC RESIN COMPOSITION
The present invention relates -to a thermo-plastic resin composition which can be suitably utilized as three-dimensional shaped articles, sheets and the like, especially automobile parts and electric par-ts made by injection molding, extrusion molding and blow molding.
More particularly, the present invention relates to a novel thermoplastic resin composition excellent in processability and paintability which comprises at least one compatibilizing agent, a polyphenylene ether, at least one polyamide resin, and a reactive compound having a molecular weight of 2,000 or less and containing nitrogen element and, as optional components, an inorganic filler and an impact strength improver.
Resin compositions comprising polyphenylene ether and polyamide have been known for a long time and a composition comprising polyphenylene ether and at most 25 ~ by weight of polyamide is disclosed in U.S. Patent No. 3,379,792, but no compatibilizing agents for compatibilizing polyphenylene ether and polyamide are disclosed therein.
A liquid diene polymer, an epoxy compound and a compound having in the molecule both la) carbon-carbon double bond or carbon-carbon triple bond and (b) carboxylic acid, acid anhydride, acid amide, imide, carboxylate ester, amino or hydroxyl group are disclosed as compatibilizing agents in U.S. Patent No. 4,315,086. This patent further discloses as impact strength improvers ethylene .
,:
:'~
propylene rubber, ethylene propylene polyene rubber or unsaturated carboxylic acid-modified products of these rubbers, SBR, polybutadiene, polystyrene-diene rubber diblock or triblock copolymers or compositions with par-tial hydrides of these copolymers.
Processes for obtaining compositions by grafting unsaturated carboxylic acids on polyphenylene ether in the presence or absence of radical initiators and mixing the resulting graft polymer with poly-amides are disclosed in Japanese Patent Kokai Nos.
59-59724 and 59-86653, U.S. Patent No. 4,654,405 and International Patent Publication WO 87/00540.
Alkenyl aromatic compounds and ~,~ un-saturated dicarboxylic acid anhydridesor their imide compounds are disclosed as compatibilizing agents for polyphenylene ether and polyamide in European Patent Publication EP-0046040.
Aliphatic polycarboxylic acids such as malic acid are disclosed in International Patent Publication WO 85/05372, oxidized polyethylene waxes are disclosed in U.S. Patent No. 4,659,760, quinones are disclosed in U.S. Patent No. 4,659,763, polyphenylene ethers made functional by epoxy compounds are disclosed in U.S. Patent No. 4,732,937, and polyfunctional compounds comprising anhydrotrimellitic acid chloride are disclosed in U.S. Patent No. 4,600,741 as compatibilizing agents for polyphenylene ether and polyamide. All of these compounds can be used in the present invention as compatibilizing agents.
Compositions comprising combination of compatibilizing agent, polyphenylene ether and crystalline polyamide with non-crystalline polyamide 2031~7~
~re disclosed in Japanese Patent Kokai Nos. 63-108060 and 63-113071 and International Patent Publication W~ 88/06173.
Fur-thermore, compositions containing nitrogen-containing heterocyclic compounds or melamine as flame retardants are known in Japanese Patent Kokai Nos. 62-236853 and 1-139642. However, resin compositions superior in paintability and other properties have not yet been developed.
Polyphenylene compositions have excellent mechanical properties and heat resistance, but have the defect that they are susceptible to discoloration when exposed to ultraviolet rays and sunlight. This defect is conspicuous especially in compositions comprising polyamide and polyphenylene ether and in general, molded articles of these compositions are painted for solving the defect or imparting decorative beautiful appearance and so compositions excellent in adhesion to coating have been demanded. However, conventional compositions comprising compatibilizing agent, polyphenylene ether and polyamide are not necessarily satisfactory in adhesion to coating and improvement of adhesion has been desired.
As a result of intensive research on various components conducted by the inventors, it has been found that compositions comprising a compatibilizing agent, polyphenylene ether and polyamide are markedly improved without damaging the excellent mechanical properties of the compositions by adding a small amount of a compound which has a molecular weight of 2,000 or less, contains nitrogen element and has ring opening or condensation polymerizability or has reactivity with acid or amine. Thus, the present 203~ ~7~
invention has been accomplished.
Tha-t is, the present invention is a thermo-plastic resin composition which comprises:
(i) at least one compatibilizing agent in an amount effective for compa-tibilization, (ii) (A) a polyphenylene ether in an amount of about 40 - 100 % by weight based on the total amount of (A) and (B) and (B) a homopolymer of alkenyl aromatic compound or a random copolymer of alkenyl aromatic compound and unsaturated compound in an amount of 0-about 60 % by weight based on the total amount of (A) and (B), the total amount of (A) and (B) being about 10 % by weight or more based on total amount of all polymer components, (iii) at least one polyamide in an amount more than the amount required for forming a continuous phase, and ~iv) a compound having a molecular weight of 2,000 or less, containing nitrogen element, and having ring opening or condensation polymeri-zability or reactivity with acid or amine.
The polyphenylene ether (ii) (A) is a polymer obtained by oxidation polymerization of at least one phenol compound represented by the formula:
- s - 203147~
0~1 R I R
`,~
(wherein Rl, R2, R3, R4 and R which may be identical or different each represents a hydrogen atom, a hologen atom, a hydrocarbon group or a substituted hydro-carbon group and at least one of them is a hydrogen atom) with oxygen or a gas containing oxygen using an oxidation coupling catalyst.
Examples of R , R , R , R and R in the above formula are hydrogen atom, halogen atoms such as chlorine, fluorine, bromine, and iodine, and hydrocarbon groups or substituted hydrocarbon groups of 1 - 18 carbon atoms, for example, alkyl groups or substituted alkyl groups such as methyl, ethyl, n-propyl, iscpropyl, pri-, sec- or t-butyl, chloroethyl, hydroxyethyl, phenylethyl, hydroxymethyl, carboxyethyl, methoxycarbonylethyl, and cyanoethyl, aryl groups or substituted aryl groups such as phenyl, chlorophenyl, methylphenyl, dimethylphenyl, and ethylphenyl, benzyl group and allyl group.
Examples of the phenol compounds shown by the above formula are phenol, o-, m- or p-cresol, 2,6-, 2,5-, 2,4- or 3,5-dimethylphenol, 2-methyl-6-phenylphenol, 2,6-diphenylphenol, 2,6-diethylphenol, 2-methyl-6-ethylphenol, and 2,3,5 ,2,3,6-, or 2,4,6-trimethylphenol, 3-methyl-6-t-butylphenol, thymol, and 2-methyl-6-allylphenol. Further, the phenol compounds may be copolymers of the compounds of the above formula and other phenol compounds, for - 6 - 203147~
example, polyhydric hydroxy aromatic compounds such as bisphenol A, tetrabromobisphenol A, resorcin, hydroquinone, and novolak resins.
Among them, preferred are homopolymers of 2,6-dimethylphenol or 2,6-diphenylphenol or copolymers of major part of 2,6-dimethylphenol and minor part of 3-methyl-6-t-butylphenol or 2,3,6-trimethylphenol.
Any oxidation coupling catalysts can be used for oxidation polymerization of the phenol com-pounds as far as they have polymerization ability.
Typical examples thereof are catalysts comprising cuprous salt and tert. amine such as cuprous chloride-triethylamine and cuprous chloride-pyridine;
catalysts comprising cupric salt-amine and alkali metal hydroxide such as cupric chloride-pyridine-potassium hydroxide; catalysts comprising manganese salt and primary amine such as manganese chloride-ethanolamine and manganese acetate-ethylenediamine;
catalysts comprising manganese salt and alcoholate or phenolate such as manganese chloride-sodium methylate and manganese chloride-sodium phenolate;
catalysts comprising cobalt salt and tert. amine.
Oxidation polymerization temperature for obtaining polyphenylene ether is 40C or higher (high temperature polymerization) or lower (low temperature polymerization). Either temperature may be used, although polymers produced thereby have different properties.
At least one polyamide (iii) used in the present invention is at least one polyamide selected from crystalline aliphatic polyamides and aromatic polyamides.
The crystalline aliphatic polyamides used in the present invention include, for example, the following.
They have a molecular weight of 10,000 or more and can be produced by bonding equimolar of a saturated aliphatic dicarboxylic acid containing 4 -12 carbon atoms and an alipha-tic diamine containing 2 - 12 carbon atoms. In this case, if necessary, the diamine may be used so as to provide more amine terminal groups than carboxyl terminal groups in the polyamide, or alternatively, a dibasic acid may be used so as to provide more acid groups. Similarly, these polyamides can be produced from the above acid and acid production derivatives and amine production derivatives such as esters, acid chlorides and amine salts of the above mentioned acids and amines.
Typical examples of the aliphatic di-carboxylic acids used for production of the polyamides include adipic acid, pimelic acid, azelaic acid, suberic acid, sebacic acid and dodecanedioic acid. Typical examples of the aliphatic diamines include hexamethylenediamine and octamethylenediamine.
Besides, these polyamides can also be produced by self-condensation of lactam.
Examples of the polyamides are polyhexamethyl-ene adipamide (nylon 66), polyhexamaethylene azelamide (nylon 69), polyhexamethylene sebacamide (nylon 610), polyhexamethylene dodecanoamide (nylon 612), poly-bis-(p-aminocyclohexyl)methane dodecanoamide, polytetramethylene adipamide (nylon 46) and polyamides 203147~
produced by ring cleavage of lactam such as polycapro-lactam (nylon 6) and polylauryl lactam. Furthermore, there may be used polyamides produced by polymeri-zation of at least two amines or acids used for production of -the above-mentioned polymers, for example, polymers produced from adipic acid, sebacic acid and hexamethylenediamine. The polyamides further include blends of polyamides such as a blend of nylon 66 and nylon 6 including copolymers such as nylon 66/6.
Preferably, these crystalline polyamides used in the present invention are nylon 46, nylon 6, nylon 66, nylon 11 and nylon 12. More preferred are nylon 6, nylon 66 and blends of nylon 66 and nylon 6 at optional blending ratio.
Furthermore, those which have terminal functional groups excess in amine terminal groups, excess in carboxyl terminal groups or balanced in these groups, or mixtures of them at optional ratio can be suitably used.
The aromatic polyamides used in the present invention are copolyamides containing an aromatic component therein, for example, polyhexamethylene isophthalamide (nylon 6I). The thermoplastic copolyamides containing aromatic component means melt-polymerizable polyamides containing as a main component an aromatic amine acid and~or an aromatic dicarboxylic acid such as para-aminoethylbenzoic acid, para-aminoethylbenzoic acid, terephthalic acid, and isophthalic acid.
Diamines which may constitute another component of the polyamide include hexamethylene-2~3~ 47~
diamine, undecamethylenediamine, dodecamethylene-diamine, 2,2,4-/2,4,4-trimethylhexamethylenediamine, m-xylylenediamine, p-xylylenediamine, bis(p-amino-cyclohexyl)methane, bis(p-aminocyclohexyl)propane, bis(3-methyl-4-aminocyclohexyl)methane, 1,3-bis(amino-methyl)cyclohexane, and 1,4-bis(aminomethyl)cyclohexane.
An isocyanate may also be used in place of the diamine.
Examples of the isocyanate are 4,4'-diphenylmethane diisocyanate and tolylene diisocyanate.
Comonomers which are used, if necessary, have no limitation and examples of the comonomers are a unit of lactam, a unit of ~-amino acid of 4 - 12 carbon atoms, a compound derived from an aliphatic dicarboxylic acid of 4 - 12 carbon atoms and an aliphatic diamine of 2 - 12 carbon atoms, for example, lactams and amino acids such as ~-caprolactam, w-laurolactam, ll-aminoundecanoic acid, and 12-aminododecanoic acid, and equimolar salts of the above-mentioned various diamines and adipic acid, azelaic acid or sebacic acid.
Typical example of the thermoplastic aromaticcopolyamidescomprising these component~ are copolymer polyamide of p-aminomethylbenzoic acid and ~-caprolactam (nylon AMBA/6), polyamides mainly composed of 2,2,4-/2,4,4-trimethylhexamethylene-diamine terephthalate (nylon TMDT and Nylon TMDT/6I), polyamide mainly composed of hexamethylene diamine isophthalate and/or hexamethylenediamine terephthalate and containing, as a comonomer, bis(p-aminocyclo-hexyl)methane isophthalate and/or bis(p-aminocyclohexyl) methane terephthalate, bis(3-methyl-4-aminocyclo-hexyl)methane isophthalate and/or bis(3-methyl-4-amino-cyclohexyl)methane terephthalate or bis(p-amino-cyclohexyl)propane isophthalate and/or 20~47~
bis(p-aminocyclohexyl)propane terephthalate (nylon 6I/PACM I, nylon 6I/DMPACM I, nylon 6I/PACP I, nylon 6I/6T/PACM I/PACM T, nylon 6I/6T/
DMPACM I/DMPACM T, nylon 6I/6T/PACP I/PACP T), polyamide mainly composed of hexamethylenediamine-isophthalate or hexamethylenediamine terephthalate and containing, as a comonomer, ~-caprolactam, 12-aminododecanoic acid, hexamethylenediamine adipate, bis(p-aminocyclohexyl)methane adipate or bis(3-methyl,4-amlnocyclohexyl)methane adipate (nylon 6I, 6I/6T, 6I/12,6T/6, 6T/66, 6I/PACM 6, 6I/DMPACM 6), and polyamides mainly composed of bis(p-aminocyclo-hexyl)methane isophthalate or bis(3-methyl,4-amino-cyclohexyl)methane-isophthalate and containing, as a comonomer, hexamethylenediamine dodecanedioate or 12-aminododecanoic acid (nylon PACM I/612, nylon DMPACM I/12).
Of these aromatic polyamides, non-crystalline aromatic polyamides are suitable.
Compounds (iv) used in the present inventionwhich have a molecular weight of 2,000 or less, contain nitrogen atom and have ring opening or condensation polymerizability or reactivity with acid amine are those of the following group.
(a) Lactams and derivatives thereof (b) Diamines and derivatives thereof (c) Diisocyanates and derivatives thereof (d) Triazines and derivatives thereof Examples of the compounds are shown below.
(a) Lactams and derivatives thereof:
203~472 11 .
Lactams such as ~-cap:rolactam, ~-laurolactam, ll-aminoundecanoic acid, 12-aminododecanoic acid, glycocyamidine, oxindol, isatin, and cyclic ureide, and derivatives thereof such as low molecular weight oligomers and metallic salts thereof.
(b) Diamines and derivatives thereof:
Diamlnes such as hexamethylenediamine, undecamethylenediamine, dodecamethylenediamine, 2,2,4-/
2,4,4-trimethylhexamethylenediamine, m-xylylenediamine, p-xy~ylenediamine, bis(p-aminocyclohexyl)methane, bis(p-aminocyclohexyl)propane, bis(3-methyl,4-amino-cyclohexyl)methane, 1,3-bis(aminomethyl)cyclohexane, and 1,4-bis(aminomethyl)cyclohexane, and derivatives thereof such as salts of these diamines with dicarboxylic acids.
(c) Diisocyanates and derivatives thereof:
Tolylene diisocyanate, diphenylmethane diisocyanate and polymers thereof, naphthalene diiso-cianate, tolidine diisocyanate, triphenylmethane triisocyanate, tris(isocyanatophenyl) thiophosphate, p-phenylene diisocyanate, hexamethylene diisocyanate, xylylene diisocyanate, isophorone diisocyanate, bis(isocyanatomethyl)cyclohexane, dicyclohexylmethane diisocyanate, lysine diisocyanate, trimethylhexa-methylene diisocyanate, 2-chloroethyl isocyanate, chloroacetyl isocyanate, 4-chlorobenzenesulfonyl isocyanate, 3,4-dichlorophenyl isocyanate, 2-isocyanatobenzoyl chloride, chlorosulfonyl isocyanate, N-(chlorocarbonyl) isocyanate, 2,4-difluorophenyl isocyanate, 4-fluoro-3-nitrophenyl isocyanate, 2-fluorophenyl isocyanate, 2-chlorophenyl isocyanate, 3-fluorophenyl isocyanate, 3-chlorophenyl isocyanate, 2031~7~
4-fluoropheny:Lisocyanate,4-chlorophenyl isocyanate, and 3-fluorosulfonylphenyl isocyanate.
(d) Triazines and derivatives thereof:
Compounds represented by the formula (I):
N N (I) ~ N-l Y z (wherein X, Y, and Zeach represents Rl or NR2R3 in which Rl, R2 and R3 each represents a hydrogen atom, an alkyl group, an aryl group or a substituent represented by the formula (II):
_~ CE~2 - o-~ R4 (II) where R4 represents a hydrogen atom or analkyl or a cycloalkyl group of 1 - 10 carbon atoms).
Examples of the compounds are melamine(2,4, 6-triamino-1,3,5-triazine), various methylolmelamines of from monomethylolmelamine to hexamethylolmelamine, etherified melamines prepared by modifying various methylolamines with monohydric alcohols, guanamine various methylolguanamines oE from monomethylol-guanamine to hexamethylolguanamine, etherifiedguanamines prepared by modifying various methylol-guanamines with monohydric alcohols, ammelide, ammeline, guanylmelamine, cyanomelamine, arylguanamines, melam, melem, and mellon.
In the present invention, adhesion to coat-203147~2 ing can be markedly improved by adding at least one compound selected from the groups of (a) - (d).
Addition amount of the compound is preferably 0.01 -10 % by weight, more preferably 0.05 - 2 ~ by weight as the amount present in the composition. If the amount is more than 10 % by weight, impact re-sistance lowers much and if it is less than 0.01 %
by weight, adhesion to coating is not improved.
(ii) (B) Homopolymers of alkenyl aromatic compounds or random copolymers of alkenyl aromatic compounds and unsaturated compounds include, for example, polystyrene, poly-p-methylstyrene, styrene-a-methylstyrene copolymer, polyvinyltoluene, styrene-alkyl (meth)acrylate copolymer and styrene-glycidyl (meth)acrylate copolymer.
In the present invention, inorganic filler and/or impact strength improver can be used as additional components. The inorganic filler is preferably at least one selected from talc, kaolin, mica,titanium oxide, clay, magnesium hydroxide, potassium titanate whisker and glass fiber. These may be used singly or in combination.
Amount of the inorganic filler is preferably 1 - 70 parts by weight per 100 parts by weight of the resin composition composed of (i), (ii), (iii) and (iv).
As the impact strength improver, various organic polymer materials used as impact resistance improver for polyamide, polyphenylene ether, polystyrene, polyolefin, and the like can be used singly or in combination. Many of them are disclosed in U.S.Patent No. 4,315,086, International Patent Publication WO/85/05372, and European Patent Publlcation EP 0236S93.
As examples of them, mention may be made of diblock copolymers, triblock copolymers, and radial teleblock copolymers of styrene and conjugated diene, and partial hydrides thereof as the first group.
These are marketed under trademarks of KRATO ~ D and KRATON~G by Shell Chemical Co. and SOLPRENE~ by philips Petroleum Co. and are easily available.
The second group includes homopolymers and random copolymers of conjugated diene monomers.
Examples of the second group are polyisoprene, polybutadiene, styrene-butadiene copolymer, isoprene-isobutylene copolymer, butadiene-acrylonitrile random copolymer, and polyoctenylene, and graft copolymers of these polymers grafted with styrene and/or unsaturated compounds having polar group such as acrylic acid, methacrylic acid, maleic anhydride and fumaric acid and derivatives thereof, glycidyl tmeth)acrylate, acrylamide, and N-methylolacrylamide.
The third group includes non-polar olefinic polymers. Examples thereof are ethylene-propylene rubber ~EPM), ethylene-propylene-polyene rubber (EPDM), ethylene-butene rubber, ethylene-butene-polyene rubber, propylene-butene rubber, polyiso-butylene, and linear low-density polyethylene, and graft copolymers of these polymers grafted with styrene, acrylonitrile and/or unsaturated compounds having polar group such as acrylic acid, methacrylic acid, maleic anhydride and fumaric ~3~7~
acid and derivatives thereof, glycidyl (meth)acrylate, acrylamide, and N-methylolacrylamide.
The fourth group includes copolymers of ethylene and unsaturated compounds having polar group.
Examples of them are ethylene-alkyl (meth)acrylate copolymers, ethylene-alkyl (meth)acrylate-maleic anhydride copolymer, ethylene-(rneth)acrylic acid copolymer, ethylene-glycidyl (meth)acrylate copolymer, ethylene-glycidyl (meth)acrylate-alkyl (meth)acrylate copolymer, and ethylene-glycidyl (meth)acrylate-vinyl acetate copolymer, and ionomers derived from these copolymers.
It is also possible to use the impact strength improvers of the first group to the fourth group in any combination of two or more.
The compatibilizing agent (i) used for compatibilization of polyphenylene ether and poly-amide in the present invention has no special limi-tation, but is suitably at least one compatibilizing agent selected from the following groups (1) - (10).
(1) Liquid diene polymers.
(2) Epoxy compounds having no ethylenically or acetylenically unsaturated bond.
(3) compounds having in the same molecule both (a) at least one unsaturated group, namely, carbon-carbon double bond or carbon-carbon triple bond and (b) at least one polar group.
(4) Oxidized polyolefin waxes.
(d) Triazines and derivatives thereof:
Compounds represented by the formula (I):
N N (I) ~ N-l Y z (wherein X, Y, and Zeach represents Rl or NR2R3 in which Rl, R2 and R3 each represents a hydrogen atom, an alkyl group, an aryl group or a substituent represented by the formula (II):
_~ CE~2 - o-~ R4 (II) where R4 represents a hydrogen atom or analkyl or a cycloalkyl group of 1 - 10 carbon atoms).
Examples of the compounds are melamine(2,4, 6-triamino-1,3,5-triazine), various methylolmelamines of from monomethylolmelamine to hexamethylolmelamine, etherified melamines prepared by modifying various methylolamines with monohydric alcohols, guanamine various methylolguanamines oE from monomethylol-guanamine to hexamethylolguanamine, etherifiedguanamines prepared by modifying various methylol-guanamines with monohydric alcohols, ammelide, ammeline, guanylmelamine, cyanomelamine, arylguanamines, melam, melem, and mellon.
In the present invention, adhesion to coat-203147~2 ing can be markedly improved by adding at least one compound selected from the groups of (a) - (d).
Addition amount of the compound is preferably 0.01 -10 % by weight, more preferably 0.05 - 2 ~ by weight as the amount present in the composition. If the amount is more than 10 % by weight, impact re-sistance lowers much and if it is less than 0.01 %
by weight, adhesion to coating is not improved.
(ii) (B) Homopolymers of alkenyl aromatic compounds or random copolymers of alkenyl aromatic compounds and unsaturated compounds include, for example, polystyrene, poly-p-methylstyrene, styrene-a-methylstyrene copolymer, polyvinyltoluene, styrene-alkyl (meth)acrylate copolymer and styrene-glycidyl (meth)acrylate copolymer.
In the present invention, inorganic filler and/or impact strength improver can be used as additional components. The inorganic filler is preferably at least one selected from talc, kaolin, mica,titanium oxide, clay, magnesium hydroxide, potassium titanate whisker and glass fiber. These may be used singly or in combination.
Amount of the inorganic filler is preferably 1 - 70 parts by weight per 100 parts by weight of the resin composition composed of (i), (ii), (iii) and (iv).
As the impact strength improver, various organic polymer materials used as impact resistance improver for polyamide, polyphenylene ether, polystyrene, polyolefin, and the like can be used singly or in combination. Many of them are disclosed in U.S.Patent No. 4,315,086, International Patent Publication WO/85/05372, and European Patent Publlcation EP 0236S93.
As examples of them, mention may be made of diblock copolymers, triblock copolymers, and radial teleblock copolymers of styrene and conjugated diene, and partial hydrides thereof as the first group.
These are marketed under trademarks of KRATO ~ D and KRATON~G by Shell Chemical Co. and SOLPRENE~ by philips Petroleum Co. and are easily available.
The second group includes homopolymers and random copolymers of conjugated diene monomers.
Examples of the second group are polyisoprene, polybutadiene, styrene-butadiene copolymer, isoprene-isobutylene copolymer, butadiene-acrylonitrile random copolymer, and polyoctenylene, and graft copolymers of these polymers grafted with styrene and/or unsaturated compounds having polar group such as acrylic acid, methacrylic acid, maleic anhydride and fumaric acid and derivatives thereof, glycidyl tmeth)acrylate, acrylamide, and N-methylolacrylamide.
The third group includes non-polar olefinic polymers. Examples thereof are ethylene-propylene rubber ~EPM), ethylene-propylene-polyene rubber (EPDM), ethylene-butene rubber, ethylene-butene-polyene rubber, propylene-butene rubber, polyiso-butylene, and linear low-density polyethylene, and graft copolymers of these polymers grafted with styrene, acrylonitrile and/or unsaturated compounds having polar group such as acrylic acid, methacrylic acid, maleic anhydride and fumaric ~3~7~
acid and derivatives thereof, glycidyl (meth)acrylate, acrylamide, and N-methylolacrylamide.
The fourth group includes copolymers of ethylene and unsaturated compounds having polar group.
Examples of them are ethylene-alkyl (meth)acrylate copolymers, ethylene-alkyl (meth)acrylate-maleic anhydride copolymer, ethylene-(rneth)acrylic acid copolymer, ethylene-glycidyl (meth)acrylate copolymer, ethylene-glycidyl (meth)acrylate-alkyl (meth)acrylate copolymer, and ethylene-glycidyl (meth)acrylate-vinyl acetate copolymer, and ionomers derived from these copolymers.
It is also possible to use the impact strength improvers of the first group to the fourth group in any combination of two or more.
The compatibilizing agent (i) used for compatibilization of polyphenylene ether and poly-amide in the present invention has no special limi-tation, but is suitably at least one compatibilizing agent selected from the following groups (1) - (10).
(1) Liquid diene polymers.
(2) Epoxy compounds having no ethylenically or acetylenically unsaturated bond.
(3) compounds having in the same molecule both (a) at least one unsaturated group, namely, carbon-carbon double bond or carbon-carbon triple bond and (b) at least one polar group.
(4) Oxidized polyolefin waxes.
(5) Quinones.
(6) Silane compounds having in molecular structure both (a) at least one silicon atom bonded to carbon atom through crosslinkage of oxygen and 2n3~47~
(b) at least ethylenic carbon-carbon double bond or carbon-carbon triple bond and/or a functional group selected from amino group and rnercapto group, said functional group being not bonded directly to silicon atom.
(b) at least ethylenic carbon-carbon double bond or carbon-carbon triple bond and/or a functional group selected from amino group and rnercapto group, said functional group being not bonded directly to silicon atom.
(7) Compounds having, in the same molecule, (a) -~ OR) (wherein R is hydrogen, analkyl group, an aryl group, an acyl group, or a carbonyldioxy group) and (b) at least two same or different functional group selected from carboxylic acid, acid halid, acid anhydride, anhydroacid halid, acid ester, acid amide, imide, amino and salts thereof.
(8) Compounds having, in the same molecule, (a) acid halide group and (b) at least one of carbo-xylic acid, carboxylic anhydride, acid ester and acid amide groups.
F'urthermore, those of the following groups (9) and (10) are also included in the compatibilizing agents which can be used in the present invention as one embodiment.
(9) Polyphenylene ethers made functional which are obtained by previously allowing poly-phenylene ether to react with at least one com-patibilizing agent selected from the groups (1) -(3) and (5) - (8).
F'urthermore, those of the following groups (9) and (10) are also included in the compatibilizing agents which can be used in the present invention as one embodiment.
(9) Polyphenylene ethers made functional which are obtained by previously allowing poly-phenylene ether to react with at least one com-patibilizing agent selected from the groups (1) -(3) and (5) - (8).
(10) Compositions obtained by rnelt knead-ing at least one compatibilizing agent selected from the groups (1) - (8), polyphenylene ether and a small amount of polyamide.
Compatibilizing agents of group (1) include, for example, homopolymers of conjugated diene and copolymers of one conjugated diene and other conjugated diene or vinyl monomer, namely, styrene, ethylene, 203~7~
propylene or the like which have a number-average molecular weight of 150 - 10000, preferably 150 -5000. Examples thereof are polybutadiene, polyisoprene, poly(butylene/isoprene), and poly(styrene/butadiene).
As compatibilizing agents of group (2), mention may be made of ~ condensates of polyhydric phenols (such as bisphenol A, tetrabromobisphenol A, and resorcin) and epichlorohydrin and ~ condensates of polyhydric alcohols (such as ethylene glycol, propylene glycol, and polyethylene glycol) and epichlorohydrin.
Compatibilizing agents of group (3) are compounds having in the same molecule both an unsaturated group, namely, a carbon-carbon double bond or a carbon-carbon triple ond and a polar group, namely, a functional group having affinity for or chemical reactivity with amide bond contained in polyamide resin and carboxyl group or amino group present at terminal of chain. Examples of such functional groups are carboxylic acid group, groups derived from carboxylic acid, namely, carboxyl groups whose hydrogen or carboxyl group is substituted such as various salts and esters, acid amide, acid anhydride, imide, acid azide, and acid halide groups, oxazoline group, nitrile group, epoxy group, amino group, hydroxyl group, and isocyanate ester group.
As these compounds having both the unsaturated group and polar group, there may be used unsaturated carboxylic acids, unsaturated carboxylic acid derivatives, unsaturated epoxy compounds, unsaturated alcohols, unsaturated amines, and unsaturated iso-cyanate esters.
Examples of the compounds are maleic 2031~7~
anhydride, maleic acid, fumaric acid, maleimide, maleic acid hydrazide, reaction products of maleic anhydride and diamines, for example, compounds having the formulas:
O O O O
Il 11 11 11 .
¢ C,--C 3 ¢ C C 3 ll ll ¦¦ OH HO ll O O O O
(wherein R is an aliphatic or aromatic group), methylnadic anhydride, dichloromaleic anhydride, maleic acid amide, itaconic acid, itaconic anhydride, natural fats and oils such as soybean oil, tung oil, caster oil, linseed oil, hempseed oil, cottonseed oil, sesame oil, rapeseed oil, peanut oil, camellia oil, olive oil, coconut oil, and sardine oil; epoxi-dized natural fats and oils such as epoxidizedsoybean oil: unsaturated carboxylic acids such as acrylic acid, butenoic acid, crotonic acid, vinyl-acetic acid, methacrylic acid, pentenoic acid, angelic acid, tiglic acid, 2-pentenoic acid, 3-pentenoic acid, a-ethylacrylic acid, B-methylcrotonic acid, 4-pentenoic acid, 2-hexenoic acid, 2-methyl-2-pentenoic acid, 3-methyl-2-pentenoic acid, ~-ethyl-crotonic acid, 2,2-dimethyl-3-butenoic acid, 2-heptenoic acid, 2-octenoic aci.d, 4-decenoic acid, 9-undecenoic acid, 10-undecenoic acid, 4-dodecenoic acid, 5-dodecenoic acid, 4-tetradecenoic acid, 9-tetra-decenoic acid, 9-hexadecenoic acid, 2-octadecenoic acid 9-octadecenoic acid, eicosenoic acid, docosenoic acid, erucic acid, tetracocenoic acid, mycolipenic acid, 2,4-pentadienoic acid, 2,4-hexadienoic acid, diallylacetic acid, geranic acid, 2,4-decadienoic 2~3~ ~72 acid, 2,4-dodecadienoic acid, 9,12-hexadecadienoic acid, 9,12-octadecadienoic acid, hexadecatrienoic acid, linolic acid, linolenic acid, octadecatrienoic acid, eicosadienoic acid, eicosatrienoic acid, eico-satetraenoic acid, ricinoleic acid, eleostearic acid,oleic acid, eicosapentaenoic acid, erucinic acid, docosadienoic acid, docosatrienoic acid, docosatetra-enoic acid, docosapentaenoic acid, tetracosenoic acid, hexacosenoic acid, hexacodienoic acid, octacosenoic acid, and triacontenoic acid; and esters, acid amides and anhydrides of these unsaturated carboxylic acids; unsaturated alcohols such as allyl alcohol, crotyl alcohol, methylvinyl carbinol, allyl carbinol, methylpropenyl carbinol, 4-pentene-1-ol, 10-undecene-1-ol, propargyl alcohol, 1,4-pentadiene-3-ol, 1,4-hexadiene-3-ol, 3,5-hexadiene-2-ol, 2,4-hexadiene-1-ol, alcohols represented by the n 2n-5H~ CnH2n_7H, CnH2 9 OH (n is a positive integer), 3-butene-1,2-diol, 2,5-dimethyl-3-hexene-2,5-diol, 1,5-hexadiene-3,4-diol, and 2,6-octadiene-4,5-diol and unsaturated amines such as ones where an OH group of these unsaturated alcohols is replaced by an -NH2 group, glycidyl (meth)acrylate and allylglycidyl ether.
Moreover, low polymers (e.g., 500 - 10,000 in average molecular weight) or high polymers (e.g., at least 10000 inaverage molecular weight) of butadiene, isoprene, etc. to which maleic anhydride orphenols are added or into which amino group, carboxylic acid group, hydroxyl group, epoxy group, or the like is introduced, and allyl isocyanate.
It is a matter of course that the definition of the compound having both unsaturated group and polar group in the same molecule includes 203~ ~7~
compounds having -two or more unsaturated groups and two or more polar groups (which may be identical or different) and furthermore, it is also possible to use two or more of -the compounds.
Among them, preferred are maleic anhydride, maleic acid, fumaric acid, itaconic anhydride, itaconic acid, and glycldyl (meth)acrylate and more preferred are maleic anhydride and fumaric acid.
The compatibilizing agents of group (4) are usually prepared by oxidation of polyolefin wax in the air or in suspension and polyethylene wax is preferred.
The compatibilizing agents of group (5) are compounds having quinone structure and examples thereof are 1,2- and 1,4-benzoquinone, Z,6-di-phenylquinone, and 2-chloro-1,4-benzoquinone.
The compatibilizing agents of group (6) are silane compounds having, in molecular structure, both (a) at least one silicon atom bonded to carbon atom through crosslinkage of oxygen and (b) at least ethylenic carbon-carbon double bond or carbon-carbon triple bond and/or functional group selected from amino group and mercapto group, said functional group being not directly bonded to silicon atom.
Examples are y-aminopropyltriethoxysilane and 2-(3-cyclohexyl)ethyltrimethoxysilane.
The compatibilizing agents of group (7) are aliphatic polycarboxylic acids, acid esters or acid amides and are represented by the formula:
(R O)mR(COOR )n (CONR R )Q
A
~, 203147~
(wherein R is a linear or branched saturated aliphatic hydrocarbon having 2 - 20, preEerably 2 - 10 carbon atoms; RI is a hydrogen atom or an alkyl, aryl, acyl or carbonyldioxy group having 1 - 10, preferably 1 - 6, more preEerably 1 - 4 carbon atoms and is most preferably hydrogen atom; RII is a hydrogen atom or an alkyl or aryl group having 1 - 20, preferably 1 -10 carbon atoms; RIII and R V are independently a hydrogen atom or an alkyl or aryl group of 1 10, preferably 1 - 6, more preferably 1 - 4 carbon atoms;
m is 1, (n+Q) is 2 or more, preferably 2 or 3, n and Q are each 0 or more than 0; (ORI) is at ~- or ~-position in respect to carbonyl group and at least two carbonyl groups are isolated by 2 - 6 carbon atoms; and carbon atom number of each of R , RII, R , and R is less than 6, it is obvious that they are not aryl groups.
Examples of these polycarboxylic acids are malic acid, malic acid and agaricic acid. Anhydrides and hydrates of these polycarboxylic acid may also be used. Examples of the acid esters are acetyl citrate and mono-ordi-stearyl citrate.
Examples of the acid amides are N,N'-diethylcitric acid amide and N-dodecylcitric acid amide.
Furthermore, derivatives of the polycarbo-xylic acids, especially salts thereof can also be suitably used.
The compatibilizing agents of group (8) are compounds having in the same molecule at least one acid halide group, most preferably acid chloride group and at least one of carboxylic acid group, - 22 - 203147~
carboxylic acid anhydride group, acid ester group and acid amide group, peferably carboxylic acid group or acid anhydride group.
Examples of these compounds are trimellitic acid chloride and anhydrotrimellitic acid chloride.
Compatibilizing agent (i) can attain the object of the present invention in an amount effective to carry out compatibilization, but amount of the compatibilizing agent (i) is preferably 0.01 - 20 parts by weight based on 100 parts by weight of (ii) and (iii). If it is less than 0.01 part by weight, the effect is small and if it is more than 20 parts by weight, further increase in effect is not obtained.
Total arnount of (ii) polyphenylene ether and random copolymer of vinyl cyanide compound and alkenyl aromatic compound and homopolymer of alkenyl aromatic compound or random copolymer of alkenyl aromatic compound and unsaturated compound is prefer-ably 10 - 95 parts by weight per 100 parts by weight of (ii) and (iii). If it is outside this range, inherent properties of the composition such as impact strength cannot be obtained.
Further, amount of (iii) at least one polyamide is preferably 90 - 5 parts by weight per 100 parts by weight of (ii) and (iii). When it is outside this range, inherent properties of the composition such as impact strength cannot be obtained.
The thermoplastic resin composition of the present invention can be produced by melt knead-ing these components (i), (ii), (iii) and (iv).
- 23 - 20~1~72 'rhe melt kneading method has no special limltation and the composition can be produced by simultaneously kneading these components by single or twin screw extruder or the like.
Preferable melt kneading method comprises previously melt kneading compatibilizing agent (i) and polyphenylene ether (ii), then adding thereto polyamide (iii) and compound (iv) having a molecular weight of 2,000 or less, containing nitrogen element and having ring opening or condensation polymeriza-bility or reactivity with acid or amine, and further melt kneading them.
lS The following nonlimiting examples illus-trates some embodiments of the present invention. The mixing ratios are all % by weight unless otherwise notified.
Izod impact strength in the following examples and comparative examples was measured in accordance with JIS K7110 (thickness 3.2 mm with notch) at room temperature.
Evaluation of paintability was conducted in the following manner: Composition of examples and comparative examples was molded into a plate of 150 x 150 x 3 mm at 290C and this plate was used for evaluation. As paint, ORIGIN PLATE ZNY (black) (manufactured by Origin Denki Co.) was used and painted at a thickness of about 25 ~ by a painting gun under ordinary conditions and the painted plate was dried in an oven at 70C for 30 minutes. After lapse of 1 hr, 2 hr, 5 hr, 12 hr, and 24 hour from drying, the plate was subjected to adhesive cellophane tape peeling test (A cellophane tape was allowed to ~031~72 adhere to the plate, then this was cut cross to form 100 squares of about 2 mm width, and thereafter the cellophane tape was peeled and percentage of remaining squares was obtained) to evaluate adhesive.
Impact strength improvers used in the examples and comparative examples were obtained by the followlng methods.
0 Preparation Example A (preparation of maleic anhydride-modified styrene grafted EPR) 100 parts by weight of EPR (ethylene-propylene copolymer, ESPRENE ~E-120P manufactured by Sumitomo Chemical Co., Ltd.), 1.5 part by weight of styrene monomer, 1.5 part by weight of maleic anhydride, and 0.1 part by weight of a free radical iniliator, namely, dicumyl peroxide (DCP manufactured by Nippon Oil &
Fats Co., Ltd.) were previously well mixed using Henschel mixer, and then extruded by twin-screw extruder (TEX 44 manufactured by Nippon Steel Works Co., Ltd.). Cylinder temperature was set at 230C and screw speed was set at 190 rpm.
Preparation Example B (Preparation of styrene grafted EPDM) 100 g of ethylene-propylene-ethylidene-norbornene terpolymer (ESPRENE~Y E-502 manufactured by Sumitomo Chemical Co., Ltd.) ground to particles of less than 5 mm edge and 350 g of water were charged in a 1.0 Q glass autoclave and with stirring thereto were added a solution prepared by dissolving 0.65 g of benzoyl peroxide in 30 g of styrene and a solution prepared by dissolving 4.0 g of polyvinyl alcohol (GOSENOL~ GL-05 manufactured by Nippon Synthetic Chemical Industry Co., Ltd.) in 100 g of water as a dispersion stabilizer in this order, followed by stirring Eor 1 hour to impregna-te the ethylene-propylene-ethylidenenorbornene terpolymer with the solutions. Then, reaction was allowed to proceed for 6 hours at 90C and Eor 2 hours at 115DC. After completion of the reaction, the reaction product was filtrated, washed with water and vacuum dried to obtain 127 g of styrene grafted EPDM.
Preparation Example C (Preparation of styrene-acrylonitrile grafted EPDM) 100 g of ethylene-propylene-ethylidene-norbornene terpolymer (ESPRENE ~ E-502 manufactured by Sumitomo Chemical Co., Ltd.) ground to particles of less than 5 mm edge and 350 g of water were charged in a 1.0 Q glass autoclave and with stirring thereto were added a solution prepared by dissolving 0.65 g of benzoyl peroxide in 25 g of styrene and 5 g of acrylonitrile and a solution prepared by dissolving 4.0 g of polyvinyl alcohol used in Preparation Example B in 100 g of water as a dispersion stabilizer in this order, followed by carrying out impregnation and reaction under the same conditions as in Preparation Example B.
After completion of the reaction, the reaction product was filtrated, washed with water and vacuum dried to obtain 125 g of styrene-acrylonitrile grafted EPDM.
Example 1 Polyphenylene ether manufactured by Nippon Polyether Co. (having a reduced viscosity of 0.54 dl/g measured in chloroform of 0.5 g/dl at 25C;
hereinafter referred to as "PPE-A"), a hydrogenated styrene-butadiene-styrene block copolymer (KRATON
G-1651 manufactured by Shell Chemical Co.; herein-2031~7-h, after referred to as "SEBS") and fumaric acid as a compatibilizing agent were dry blended and the mixture was fed from the first hopper of a twin-screw kneader (TEM-50 manufactured by Toshiba Machine Co., Ltd.) and polyamide (UNITIKA NYLON 6 A1030BRL) and ~-caprolactam as a paintability improver were introduced from the second hopper between the first hopper and vent hole and these were kneaded. That is, 100 parts by weight of a mixture of PPE-A 40 wt~, SEBS 10 wt~ and polyamide 50 wt~, and 0.5 part by weight of fumaric acid and 0.5 part by weight of ~-caprolactam were kneaded and granulated. Kneading conditions were cylinder temperature 260C and screw speed 330 rpm. The resulting composi-tion was dried and a plate of 150 x 150 x 3 mm and a test piece for Izod impact test were molded therefrom by an injection molding machine (Toshiba IS-220EN). Molding conditions were set temperature 290C and mold temperature 80C. Results of evaluation of paintability and Izod impact strength are shown in Table 1.
Example 2 Example 1 was repeated except that styrene-acrylonitrile grafted EPDM (shown in PreparationExample C, hereinafter referred to as "St-AN-g-EPDM") was used in place of SEBS and 1.0 part by weight of ~-laurolactam was used in place of ~-caprolactam as a paintability improver.
Example 3 Example 1 was repeated except that 0.8 part by weight of melamine was used in place of ~-caprolactam as paintability improver.
Comparative Example 1 Example 1 was repeated except that the paintability improver was not used.
Example 4 Example 1 was repeated except that the paintability improver was introduced not from the second hopper, but from the first hopper.
Example 5 Example 1 was repeated except that polyamide and paintability improver were not introduced from the second hopper, but introduced from the first hopper together with PPE-A, SEBS and fumaric acid.
Comparative Example 2 Example 1 was repeated except that compati-bilizing agent was not introduced.
Example 6 Example 1 was repeated except that PPE-B
(reduced viscosity in chloroform : 0.46 dl/g) was used in place of PPE-A, styrene-butadiene-styrene block copolymer (CALIFLEX ~3 TRllOl manufactured by Shell Chemical Co.; hereinafter referred to as "SBS") was used in place of SEBS, 0.5 part by weight of maleic anhydride was used in place of fumaric acid as compatibili~ing agent, 45 wt% of nylon 6 A1030BRL
and 5 wt% of nylon 66 A100 ~MARANYL ~ A100 manufactured by ICI) were used in place of 50 wt~ of polyamide nylon 6 A1030BRL, and 0.4 part by weight of hexamethylol-melamine was used in place of ~-caprolactam.
Example 7 Example 6 was repeated except that 11-aminoundecanoic acid was used as paintability improver.
- 28 - 2031~72 Example 8 Example 6 was repeated except that hexa-methylenediamine was used as paintability improver.
Example 9 Example 6 was repeated except that diphenyl-methane diisocyanate was used as paintability improver.
Comparative Example 3 Example 6 was repeated except that painta-bility improver was not used.
Example 10 45 wt% of PPE-B, 10 wt% of styrene grafted EPDM (shown in Preparation Example B; hereinafter referred to as "St-g-EPDM"),and 0.5 part by weight of fumaric acid (based on 100 parts by weight of PPE-B, St-g-EPDM, and polyamide component) as compati-bilizing agent were introduced from the first hopper and 45 wt% of polyamide (nylon 6, A1030BRL) and 0.6 part by weight of guanamine (based on 100 parts by weight of PPE-B, St-g-EPDM, and polyamide component) as paintability improver were introduced from the second hopper. The resulting composition was evaluated in the same manner as in Example 1.
Example 11 Example 10 was repeated except that 10 wt%
of St-AN-g-EPDM was used in place of St-g-EPDM, 0.5 part by weight of maleic anhydride was used in place of fumaric acid, and 0.2 part by weight of ~-caprolactam was used as paintability improver.
Comparative Example 4 2031~72 Example 10 was repeated except that 10 wt%
of maleic anhydride modlfied styrene grafted EPR
(shown in Preparation ~xample A; hereinafter referred to as "m-EPR") was used in place of St-g-EPDM
and 12 parts by weight of melamine was used as paintability improver.
Example 12 Comparative Example 4 was repeated except that 45 wt~ of PPE-A was used in place of PPE-B, 0.6 part by weight of citric acid was used in place of maleic anhydride as compatibilizing agent, and 0.4 part of -caprolactam was used in place of 12 parts of melamine as paintability improver.
Example 13 Example 10 was repeated except that 45 wt%
of PPE-A was used in place of PPE-B, 10 wt~ of ESPRENE EMA ~ 3601 (manufactured by Sumitomo Chemical Co., Ltd.; hereinafter referred to as "EMA") was used in place of St-g-EPDM, 45 wt~ of nylon 66 (A100) was used in place of nylon 6 (A1030BRL) as polyamide, and 0.2 part by weight of melaminewas used as painta-bility improver.
Comparative Example 5 Example 13 was repeated except that painta-bility improver was not used.
Example 14 Example 10 was repeated except that hydrogenated styrene-isoprene block copolymer (KRATON G ~ 1701 manufactured by Shell Chemical Co.
was used in place of St-g-EPDM and 3.0 parts by weight of ~-caprolac-tam was used as paintability improver.
203~47~
Example 15 50 wt% of PPE-B and 0.5 part by weight of maleic anhydride (based on 100 parts by weight of PPE-B and polyamide component) as compatibilizing agent were introduced from the first hopper and 50 wt% of polyamide (nylon 6 A1030BRL) and 0.5 part by weight of ~-caprolactam (based on 100 parts by weight of PPE-Band polyamide component) as painta-bility improver were introduced from the second hopper and the resulting product was evaluated on paintability in the same manner as in Exarnple 1.
Comparative Example 6 Example 15 was repeated except that painta-bility improver was not used.
Example 16 45 wt% of PPE-B and 0.5 part by weight of maleic anhydride (based on 100 parts by weight of PPE-B, polyamide and SBS component) as compatibi-lizing agent were introduced from the first hopper and 45 wt% of polyamide (nylon 6 A1030 BRL), 10 wt%
of SBS and O.S part by weight of ~-caprolactam (based on 100 parts by weight of PPE-B, polyamide and SBS
component) as paintability improver were introduced from the second hopper and the resulting product was evaluated on paintability and Izod impact strength in the same manner as in Example 1.
Results obtained in these Examples and Comparative Examples are shown in Tables 1 - 3.
As is clear from Tables 1 - 3, according to the present invention, film adhesion can be improved by adding specific paintability improver.
Futher more, resin compositions having good impact 203147~
resistance with improving film adhesion can be obtained by introducing PPE and compatibilizing agent from the first hopper and paintability improver from the second hopper to carry out multi-stage kneading.
2~31~7~
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2031~7~
~ ccording to the present invention, it has been found that thermoplastic resin compositions comprising polyphenylene ether, polyamide, compatibi-lizing agent and impact strength improver can be remarkably improved in paintability, espetially adhesion in a short time after painting by adding thereto a compound having a molecular weight of 2,000 or less, containing nitrogen element and having ring opening or condensation polymerizability.
Thus, paintability which is one of the problems of compositions of polyphenylene ether and polyamide can be solved and the compositions have a wide variety of uses.
The novel resin compositlons provided by the present invention can be easily processed into shaped products, sheets and films by processing method used for thermoplastic resin compositions such as injection molding and extrusion molding. The thus obtained products have very good balance in properties such as impact resistance, heat re-sistance and flexural rigidity and besides are superior in paintability. The compositions are especially suitable for being processed by injection molding.
Compatibilizing agents of group (1) include, for example, homopolymers of conjugated diene and copolymers of one conjugated diene and other conjugated diene or vinyl monomer, namely, styrene, ethylene, 203~7~
propylene or the like which have a number-average molecular weight of 150 - 10000, preferably 150 -5000. Examples thereof are polybutadiene, polyisoprene, poly(butylene/isoprene), and poly(styrene/butadiene).
As compatibilizing agents of group (2), mention may be made of ~ condensates of polyhydric phenols (such as bisphenol A, tetrabromobisphenol A, and resorcin) and epichlorohydrin and ~ condensates of polyhydric alcohols (such as ethylene glycol, propylene glycol, and polyethylene glycol) and epichlorohydrin.
Compatibilizing agents of group (3) are compounds having in the same molecule both an unsaturated group, namely, a carbon-carbon double bond or a carbon-carbon triple ond and a polar group, namely, a functional group having affinity for or chemical reactivity with amide bond contained in polyamide resin and carboxyl group or amino group present at terminal of chain. Examples of such functional groups are carboxylic acid group, groups derived from carboxylic acid, namely, carboxyl groups whose hydrogen or carboxyl group is substituted such as various salts and esters, acid amide, acid anhydride, imide, acid azide, and acid halide groups, oxazoline group, nitrile group, epoxy group, amino group, hydroxyl group, and isocyanate ester group.
As these compounds having both the unsaturated group and polar group, there may be used unsaturated carboxylic acids, unsaturated carboxylic acid derivatives, unsaturated epoxy compounds, unsaturated alcohols, unsaturated amines, and unsaturated iso-cyanate esters.
Examples of the compounds are maleic 2031~7~
anhydride, maleic acid, fumaric acid, maleimide, maleic acid hydrazide, reaction products of maleic anhydride and diamines, for example, compounds having the formulas:
O O O O
Il 11 11 11 .
¢ C,--C 3 ¢ C C 3 ll ll ¦¦ OH HO ll O O O O
(wherein R is an aliphatic or aromatic group), methylnadic anhydride, dichloromaleic anhydride, maleic acid amide, itaconic acid, itaconic anhydride, natural fats and oils such as soybean oil, tung oil, caster oil, linseed oil, hempseed oil, cottonseed oil, sesame oil, rapeseed oil, peanut oil, camellia oil, olive oil, coconut oil, and sardine oil; epoxi-dized natural fats and oils such as epoxidizedsoybean oil: unsaturated carboxylic acids such as acrylic acid, butenoic acid, crotonic acid, vinyl-acetic acid, methacrylic acid, pentenoic acid, angelic acid, tiglic acid, 2-pentenoic acid, 3-pentenoic acid, a-ethylacrylic acid, B-methylcrotonic acid, 4-pentenoic acid, 2-hexenoic acid, 2-methyl-2-pentenoic acid, 3-methyl-2-pentenoic acid, ~-ethyl-crotonic acid, 2,2-dimethyl-3-butenoic acid, 2-heptenoic acid, 2-octenoic aci.d, 4-decenoic acid, 9-undecenoic acid, 10-undecenoic acid, 4-dodecenoic acid, 5-dodecenoic acid, 4-tetradecenoic acid, 9-tetra-decenoic acid, 9-hexadecenoic acid, 2-octadecenoic acid 9-octadecenoic acid, eicosenoic acid, docosenoic acid, erucic acid, tetracocenoic acid, mycolipenic acid, 2,4-pentadienoic acid, 2,4-hexadienoic acid, diallylacetic acid, geranic acid, 2,4-decadienoic 2~3~ ~72 acid, 2,4-dodecadienoic acid, 9,12-hexadecadienoic acid, 9,12-octadecadienoic acid, hexadecatrienoic acid, linolic acid, linolenic acid, octadecatrienoic acid, eicosadienoic acid, eicosatrienoic acid, eico-satetraenoic acid, ricinoleic acid, eleostearic acid,oleic acid, eicosapentaenoic acid, erucinic acid, docosadienoic acid, docosatrienoic acid, docosatetra-enoic acid, docosapentaenoic acid, tetracosenoic acid, hexacosenoic acid, hexacodienoic acid, octacosenoic acid, and triacontenoic acid; and esters, acid amides and anhydrides of these unsaturated carboxylic acids; unsaturated alcohols such as allyl alcohol, crotyl alcohol, methylvinyl carbinol, allyl carbinol, methylpropenyl carbinol, 4-pentene-1-ol, 10-undecene-1-ol, propargyl alcohol, 1,4-pentadiene-3-ol, 1,4-hexadiene-3-ol, 3,5-hexadiene-2-ol, 2,4-hexadiene-1-ol, alcohols represented by the n 2n-5H~ CnH2n_7H, CnH2 9 OH (n is a positive integer), 3-butene-1,2-diol, 2,5-dimethyl-3-hexene-2,5-diol, 1,5-hexadiene-3,4-diol, and 2,6-octadiene-4,5-diol and unsaturated amines such as ones where an OH group of these unsaturated alcohols is replaced by an -NH2 group, glycidyl (meth)acrylate and allylglycidyl ether.
Moreover, low polymers (e.g., 500 - 10,000 in average molecular weight) or high polymers (e.g., at least 10000 inaverage molecular weight) of butadiene, isoprene, etc. to which maleic anhydride orphenols are added or into which amino group, carboxylic acid group, hydroxyl group, epoxy group, or the like is introduced, and allyl isocyanate.
It is a matter of course that the definition of the compound having both unsaturated group and polar group in the same molecule includes 203~ ~7~
compounds having -two or more unsaturated groups and two or more polar groups (which may be identical or different) and furthermore, it is also possible to use two or more of -the compounds.
Among them, preferred are maleic anhydride, maleic acid, fumaric acid, itaconic anhydride, itaconic acid, and glycldyl (meth)acrylate and more preferred are maleic anhydride and fumaric acid.
The compatibilizing agents of group (4) are usually prepared by oxidation of polyolefin wax in the air or in suspension and polyethylene wax is preferred.
The compatibilizing agents of group (5) are compounds having quinone structure and examples thereof are 1,2- and 1,4-benzoquinone, Z,6-di-phenylquinone, and 2-chloro-1,4-benzoquinone.
The compatibilizing agents of group (6) are silane compounds having, in molecular structure, both (a) at least one silicon atom bonded to carbon atom through crosslinkage of oxygen and (b) at least ethylenic carbon-carbon double bond or carbon-carbon triple bond and/or functional group selected from amino group and mercapto group, said functional group being not directly bonded to silicon atom.
Examples are y-aminopropyltriethoxysilane and 2-(3-cyclohexyl)ethyltrimethoxysilane.
The compatibilizing agents of group (7) are aliphatic polycarboxylic acids, acid esters or acid amides and are represented by the formula:
(R O)mR(COOR )n (CONR R )Q
A
~, 203147~
(wherein R is a linear or branched saturated aliphatic hydrocarbon having 2 - 20, preEerably 2 - 10 carbon atoms; RI is a hydrogen atom or an alkyl, aryl, acyl or carbonyldioxy group having 1 - 10, preferably 1 - 6, more preEerably 1 - 4 carbon atoms and is most preferably hydrogen atom; RII is a hydrogen atom or an alkyl or aryl group having 1 - 20, preferably 1 -10 carbon atoms; RIII and R V are independently a hydrogen atom or an alkyl or aryl group of 1 10, preferably 1 - 6, more preferably 1 - 4 carbon atoms;
m is 1, (n+Q) is 2 or more, preferably 2 or 3, n and Q are each 0 or more than 0; (ORI) is at ~- or ~-position in respect to carbonyl group and at least two carbonyl groups are isolated by 2 - 6 carbon atoms; and carbon atom number of each of R , RII, R , and R is less than 6, it is obvious that they are not aryl groups.
Examples of these polycarboxylic acids are malic acid, malic acid and agaricic acid. Anhydrides and hydrates of these polycarboxylic acid may also be used. Examples of the acid esters are acetyl citrate and mono-ordi-stearyl citrate.
Examples of the acid amides are N,N'-diethylcitric acid amide and N-dodecylcitric acid amide.
Furthermore, derivatives of the polycarbo-xylic acids, especially salts thereof can also be suitably used.
The compatibilizing agents of group (8) are compounds having in the same molecule at least one acid halide group, most preferably acid chloride group and at least one of carboxylic acid group, - 22 - 203147~
carboxylic acid anhydride group, acid ester group and acid amide group, peferably carboxylic acid group or acid anhydride group.
Examples of these compounds are trimellitic acid chloride and anhydrotrimellitic acid chloride.
Compatibilizing agent (i) can attain the object of the present invention in an amount effective to carry out compatibilization, but amount of the compatibilizing agent (i) is preferably 0.01 - 20 parts by weight based on 100 parts by weight of (ii) and (iii). If it is less than 0.01 part by weight, the effect is small and if it is more than 20 parts by weight, further increase in effect is not obtained.
Total arnount of (ii) polyphenylene ether and random copolymer of vinyl cyanide compound and alkenyl aromatic compound and homopolymer of alkenyl aromatic compound or random copolymer of alkenyl aromatic compound and unsaturated compound is prefer-ably 10 - 95 parts by weight per 100 parts by weight of (ii) and (iii). If it is outside this range, inherent properties of the composition such as impact strength cannot be obtained.
Further, amount of (iii) at least one polyamide is preferably 90 - 5 parts by weight per 100 parts by weight of (ii) and (iii). When it is outside this range, inherent properties of the composition such as impact strength cannot be obtained.
The thermoplastic resin composition of the present invention can be produced by melt knead-ing these components (i), (ii), (iii) and (iv).
- 23 - 20~1~72 'rhe melt kneading method has no special limltation and the composition can be produced by simultaneously kneading these components by single or twin screw extruder or the like.
Preferable melt kneading method comprises previously melt kneading compatibilizing agent (i) and polyphenylene ether (ii), then adding thereto polyamide (iii) and compound (iv) having a molecular weight of 2,000 or less, containing nitrogen element and having ring opening or condensation polymeriza-bility or reactivity with acid or amine, and further melt kneading them.
lS The following nonlimiting examples illus-trates some embodiments of the present invention. The mixing ratios are all % by weight unless otherwise notified.
Izod impact strength in the following examples and comparative examples was measured in accordance with JIS K7110 (thickness 3.2 mm with notch) at room temperature.
Evaluation of paintability was conducted in the following manner: Composition of examples and comparative examples was molded into a plate of 150 x 150 x 3 mm at 290C and this plate was used for evaluation. As paint, ORIGIN PLATE ZNY (black) (manufactured by Origin Denki Co.) was used and painted at a thickness of about 25 ~ by a painting gun under ordinary conditions and the painted plate was dried in an oven at 70C for 30 minutes. After lapse of 1 hr, 2 hr, 5 hr, 12 hr, and 24 hour from drying, the plate was subjected to adhesive cellophane tape peeling test (A cellophane tape was allowed to ~031~72 adhere to the plate, then this was cut cross to form 100 squares of about 2 mm width, and thereafter the cellophane tape was peeled and percentage of remaining squares was obtained) to evaluate adhesive.
Impact strength improvers used in the examples and comparative examples were obtained by the followlng methods.
0 Preparation Example A (preparation of maleic anhydride-modified styrene grafted EPR) 100 parts by weight of EPR (ethylene-propylene copolymer, ESPRENE ~E-120P manufactured by Sumitomo Chemical Co., Ltd.), 1.5 part by weight of styrene monomer, 1.5 part by weight of maleic anhydride, and 0.1 part by weight of a free radical iniliator, namely, dicumyl peroxide (DCP manufactured by Nippon Oil &
Fats Co., Ltd.) were previously well mixed using Henschel mixer, and then extruded by twin-screw extruder (TEX 44 manufactured by Nippon Steel Works Co., Ltd.). Cylinder temperature was set at 230C and screw speed was set at 190 rpm.
Preparation Example B (Preparation of styrene grafted EPDM) 100 g of ethylene-propylene-ethylidene-norbornene terpolymer (ESPRENE~Y E-502 manufactured by Sumitomo Chemical Co., Ltd.) ground to particles of less than 5 mm edge and 350 g of water were charged in a 1.0 Q glass autoclave and with stirring thereto were added a solution prepared by dissolving 0.65 g of benzoyl peroxide in 30 g of styrene and a solution prepared by dissolving 4.0 g of polyvinyl alcohol (GOSENOL~ GL-05 manufactured by Nippon Synthetic Chemical Industry Co., Ltd.) in 100 g of water as a dispersion stabilizer in this order, followed by stirring Eor 1 hour to impregna-te the ethylene-propylene-ethylidenenorbornene terpolymer with the solutions. Then, reaction was allowed to proceed for 6 hours at 90C and Eor 2 hours at 115DC. After completion of the reaction, the reaction product was filtrated, washed with water and vacuum dried to obtain 127 g of styrene grafted EPDM.
Preparation Example C (Preparation of styrene-acrylonitrile grafted EPDM) 100 g of ethylene-propylene-ethylidene-norbornene terpolymer (ESPRENE ~ E-502 manufactured by Sumitomo Chemical Co., Ltd.) ground to particles of less than 5 mm edge and 350 g of water were charged in a 1.0 Q glass autoclave and with stirring thereto were added a solution prepared by dissolving 0.65 g of benzoyl peroxide in 25 g of styrene and 5 g of acrylonitrile and a solution prepared by dissolving 4.0 g of polyvinyl alcohol used in Preparation Example B in 100 g of water as a dispersion stabilizer in this order, followed by carrying out impregnation and reaction under the same conditions as in Preparation Example B.
After completion of the reaction, the reaction product was filtrated, washed with water and vacuum dried to obtain 125 g of styrene-acrylonitrile grafted EPDM.
Example 1 Polyphenylene ether manufactured by Nippon Polyether Co. (having a reduced viscosity of 0.54 dl/g measured in chloroform of 0.5 g/dl at 25C;
hereinafter referred to as "PPE-A"), a hydrogenated styrene-butadiene-styrene block copolymer (KRATON
G-1651 manufactured by Shell Chemical Co.; herein-2031~7-h, after referred to as "SEBS") and fumaric acid as a compatibilizing agent were dry blended and the mixture was fed from the first hopper of a twin-screw kneader (TEM-50 manufactured by Toshiba Machine Co., Ltd.) and polyamide (UNITIKA NYLON 6 A1030BRL) and ~-caprolactam as a paintability improver were introduced from the second hopper between the first hopper and vent hole and these were kneaded. That is, 100 parts by weight of a mixture of PPE-A 40 wt~, SEBS 10 wt~ and polyamide 50 wt~, and 0.5 part by weight of fumaric acid and 0.5 part by weight of ~-caprolactam were kneaded and granulated. Kneading conditions were cylinder temperature 260C and screw speed 330 rpm. The resulting composi-tion was dried and a plate of 150 x 150 x 3 mm and a test piece for Izod impact test were molded therefrom by an injection molding machine (Toshiba IS-220EN). Molding conditions were set temperature 290C and mold temperature 80C. Results of evaluation of paintability and Izod impact strength are shown in Table 1.
Example 2 Example 1 was repeated except that styrene-acrylonitrile grafted EPDM (shown in PreparationExample C, hereinafter referred to as "St-AN-g-EPDM") was used in place of SEBS and 1.0 part by weight of ~-laurolactam was used in place of ~-caprolactam as a paintability improver.
Example 3 Example 1 was repeated except that 0.8 part by weight of melamine was used in place of ~-caprolactam as paintability improver.
Comparative Example 1 Example 1 was repeated except that the paintability improver was not used.
Example 4 Example 1 was repeated except that the paintability improver was introduced not from the second hopper, but from the first hopper.
Example 5 Example 1 was repeated except that polyamide and paintability improver were not introduced from the second hopper, but introduced from the first hopper together with PPE-A, SEBS and fumaric acid.
Comparative Example 2 Example 1 was repeated except that compati-bilizing agent was not introduced.
Example 6 Example 1 was repeated except that PPE-B
(reduced viscosity in chloroform : 0.46 dl/g) was used in place of PPE-A, styrene-butadiene-styrene block copolymer (CALIFLEX ~3 TRllOl manufactured by Shell Chemical Co.; hereinafter referred to as "SBS") was used in place of SEBS, 0.5 part by weight of maleic anhydride was used in place of fumaric acid as compatibili~ing agent, 45 wt% of nylon 6 A1030BRL
and 5 wt% of nylon 66 A100 ~MARANYL ~ A100 manufactured by ICI) were used in place of 50 wt~ of polyamide nylon 6 A1030BRL, and 0.4 part by weight of hexamethylol-melamine was used in place of ~-caprolactam.
Example 7 Example 6 was repeated except that 11-aminoundecanoic acid was used as paintability improver.
- 28 - 2031~72 Example 8 Example 6 was repeated except that hexa-methylenediamine was used as paintability improver.
Example 9 Example 6 was repeated except that diphenyl-methane diisocyanate was used as paintability improver.
Comparative Example 3 Example 6 was repeated except that painta-bility improver was not used.
Example 10 45 wt% of PPE-B, 10 wt% of styrene grafted EPDM (shown in Preparation Example B; hereinafter referred to as "St-g-EPDM"),and 0.5 part by weight of fumaric acid (based on 100 parts by weight of PPE-B, St-g-EPDM, and polyamide component) as compati-bilizing agent were introduced from the first hopper and 45 wt% of polyamide (nylon 6, A1030BRL) and 0.6 part by weight of guanamine (based on 100 parts by weight of PPE-B, St-g-EPDM, and polyamide component) as paintability improver were introduced from the second hopper. The resulting composition was evaluated in the same manner as in Example 1.
Example 11 Example 10 was repeated except that 10 wt%
of St-AN-g-EPDM was used in place of St-g-EPDM, 0.5 part by weight of maleic anhydride was used in place of fumaric acid, and 0.2 part by weight of ~-caprolactam was used as paintability improver.
Comparative Example 4 2031~72 Example 10 was repeated except that 10 wt%
of maleic anhydride modlfied styrene grafted EPR
(shown in Preparation ~xample A; hereinafter referred to as "m-EPR") was used in place of St-g-EPDM
and 12 parts by weight of melamine was used as paintability improver.
Example 12 Comparative Example 4 was repeated except that 45 wt~ of PPE-A was used in place of PPE-B, 0.6 part by weight of citric acid was used in place of maleic anhydride as compatibilizing agent, and 0.4 part of -caprolactam was used in place of 12 parts of melamine as paintability improver.
Example 13 Example 10 was repeated except that 45 wt%
of PPE-A was used in place of PPE-B, 10 wt~ of ESPRENE EMA ~ 3601 (manufactured by Sumitomo Chemical Co., Ltd.; hereinafter referred to as "EMA") was used in place of St-g-EPDM, 45 wt~ of nylon 66 (A100) was used in place of nylon 6 (A1030BRL) as polyamide, and 0.2 part by weight of melaminewas used as painta-bility improver.
Comparative Example 5 Example 13 was repeated except that painta-bility improver was not used.
Example 14 Example 10 was repeated except that hydrogenated styrene-isoprene block copolymer (KRATON G ~ 1701 manufactured by Shell Chemical Co.
was used in place of St-g-EPDM and 3.0 parts by weight of ~-caprolac-tam was used as paintability improver.
203~47~
Example 15 50 wt% of PPE-B and 0.5 part by weight of maleic anhydride (based on 100 parts by weight of PPE-B and polyamide component) as compatibilizing agent were introduced from the first hopper and 50 wt% of polyamide (nylon 6 A1030BRL) and 0.5 part by weight of ~-caprolactam (based on 100 parts by weight of PPE-Band polyamide component) as painta-bility improver were introduced from the second hopper and the resulting product was evaluated on paintability in the same manner as in Exarnple 1.
Comparative Example 6 Example 15 was repeated except that painta-bility improver was not used.
Example 16 45 wt% of PPE-B and 0.5 part by weight of maleic anhydride (based on 100 parts by weight of PPE-B, polyamide and SBS component) as compatibi-lizing agent were introduced from the first hopper and 45 wt% of polyamide (nylon 6 A1030 BRL), 10 wt%
of SBS and O.S part by weight of ~-caprolactam (based on 100 parts by weight of PPE-B, polyamide and SBS
component) as paintability improver were introduced from the second hopper and the resulting product was evaluated on paintability and Izod impact strength in the same manner as in Example 1.
Results obtained in these Examples and Comparative Examples are shown in Tables 1 - 3.
As is clear from Tables 1 - 3, according to the present invention, film adhesion can be improved by adding specific paintability improver.
Futher more, resin compositions having good impact 203147~
resistance with improving film adhesion can be obtained by introducing PPE and compatibilizing agent from the first hopper and paintability improver from the second hopper to carry out multi-stage kneading.
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~ ccording to the present invention, it has been found that thermoplastic resin compositions comprising polyphenylene ether, polyamide, compatibi-lizing agent and impact strength improver can be remarkably improved in paintability, espetially adhesion in a short time after painting by adding thereto a compound having a molecular weight of 2,000 or less, containing nitrogen element and having ring opening or condensation polymerizability.
Thus, paintability which is one of the problems of compositions of polyphenylene ether and polyamide can be solved and the compositions have a wide variety of uses.
The novel resin compositlons provided by the present invention can be easily processed into shaped products, sheets and films by processing method used for thermoplastic resin compositions such as injection molding and extrusion molding. The thus obtained products have very good balance in properties such as impact resistance, heat re-sistance and flexural rigidity and besides are superior in paintability. The compositions are especially suitable for being processed by injection molding.
Claims (17)
1. A thermoplastic resin composition which comprises:
(i) at least one compatibilizing agent in an amount effective for compatibilization, (ii) (A) a polyphenylene ether in an amount of about 40 - 100 % by weight based on the total amount of (A) and (B) and (B) a homopolymer of alkenyl aromatic compound or a random copolymer of alkenyl aromatic compound and unsaturated compound in an amount of about 60 % by weight or less based on the total amount of (A) and (B), the total amount of (A) and (B) being about 10 % by weight or more based on total amount of all polymer components, (iii) at least one polyamide in an amount more than the amount required for forming a continuous phase, and (iv) a compound having a molecular weight of 2,000 or less, containing nitrogen element, and having ring opening or condensation polymerizability or reactivity with acid or amine.
(i) at least one compatibilizing agent in an amount effective for compatibilization, (ii) (A) a polyphenylene ether in an amount of about 40 - 100 % by weight based on the total amount of (A) and (B) and (B) a homopolymer of alkenyl aromatic compound or a random copolymer of alkenyl aromatic compound and unsaturated compound in an amount of about 60 % by weight or less based on the total amount of (A) and (B), the total amount of (A) and (B) being about 10 % by weight or more based on total amount of all polymer components, (iii) at least one polyamide in an amount more than the amount required for forming a continuous phase, and (iv) a compound having a molecular weight of 2,000 or less, containing nitrogen element, and having ring opening or condensation polymerizability or reactivity with acid or amine.
2. A resin composition according to claim 1, wherein compatibilizing agent (i) is at least one compatibilizing agent selected from the following groups (1) - (10):
(1) liquid diene polymers, (2) epoxy compounds having neither ethylenic unsaturated bond nor acetylenic unsaturated bond, (3) compounds having in the same molecule both (a) at least one unsaturated group selected from the group consisting of carbon-carbon double bond and carbon-carbon triple bond and (b) at least one polar group, (4) oxidized polyolefin waxes, (5) quinones, (6) silane compounds having in molecular structure both (a) at least one silicon atom bonded to carbon atom through crosslinkage of oxygen and (b) at least ethylenic carbon-carbon double bond or carbon-carbon triple bond and/or a functional group selected from amino group and mercapto group, said functional group being not directly bonded to silicon atom, (7) compounds having, in the same molecule, (a) -( OR) wherein R is hydrogen,an alkyl group, an aryl group, an acyl group, or a carbonyldioxy group and (b) at least two same or different functional groups selected from carboxylic acid group, acid halide group, acid anhydride group, anhydroacid halide group, acid ester group, acid amide group, imide group, amino group and salts thereof, (8) compounds having, in the same molecule, (a) acid halide group and (b) at least one of carboxylic acid group, carboxylic anhydride group, acid ester group and acid amide group, (9) polyphenylene ethers made functional by at least one compatibilizing agent selected from the groups (1) - (3) and (5) - (8), and (10) compositions obtained by melt kneading at least one compatlbilizing agent selected from the groups (1) - (8), polyphenylene ether and a small amount of polyamide.
(1) liquid diene polymers, (2) epoxy compounds having neither ethylenic unsaturated bond nor acetylenic unsaturated bond, (3) compounds having in the same molecule both (a) at least one unsaturated group selected from the group consisting of carbon-carbon double bond and carbon-carbon triple bond and (b) at least one polar group, (4) oxidized polyolefin waxes, (5) quinones, (6) silane compounds having in molecular structure both (a) at least one silicon atom bonded to carbon atom through crosslinkage of oxygen and (b) at least ethylenic carbon-carbon double bond or carbon-carbon triple bond and/or a functional group selected from amino group and mercapto group, said functional group being not directly bonded to silicon atom, (7) compounds having, in the same molecule, (a) -( OR) wherein R is hydrogen,an alkyl group, an aryl group, an acyl group, or a carbonyldioxy group and (b) at least two same or different functional groups selected from carboxylic acid group, acid halide group, acid anhydride group, anhydroacid halide group, acid ester group, acid amide group, imide group, amino group and salts thereof, (8) compounds having, in the same molecule, (a) acid halide group and (b) at least one of carboxylic acid group, carboxylic anhydride group, acid ester group and acid amide group, (9) polyphenylene ethers made functional by at least one compatibilizing agent selected from the groups (1) - (3) and (5) - (8), and (10) compositions obtained by melt kneading at least one compatlbilizing agent selected from the groups (1) - (8), polyphenylene ether and a small amount of polyamide.
3. A resin composition according to claim 1, which comprises:
(i) compatibilizing agent in an amount of 0.01 - 20 parts by weight, (ii) (A) polyphenylene and (B) the random copolymer of alkenyl aromatic compound and unsaturated compound in a total amount of 10 - 95 parts by weight, (iii) polyamide in an amount of 90 - 5 parts by weight, and (iv) compound having a molecular weight of 2,000 or less, containing nitrogen element, and having ring opening or condensation polymerizability or reactivity with acid or amine in an amount of 0.01 -10 % by weight based on the total amount of the components (i), (ii) and (iii).
(i) compatibilizing agent in an amount of 0.01 - 20 parts by weight, (ii) (A) polyphenylene and (B) the random copolymer of alkenyl aromatic compound and unsaturated compound in a total amount of 10 - 95 parts by weight, (iii) polyamide in an amount of 90 - 5 parts by weight, and (iv) compound having a molecular weight of 2,000 or less, containing nitrogen element, and having ring opening or condensation polymerizability or reactivity with acid or amine in an amount of 0.01 -10 % by weight based on the total amount of the components (i), (ii) and (iii).
4. A resin composition according to claim 1, wherein the alkenyl aromatic compound in (ii) is at least one compound selected from the group consisting of styrene, vinyltoluene and .alpha.-methylstyrene.
5. A resin composition according to claim 1, wherein the compound (iv) is lactam or derivative thereof.
6. A resin composition according to claim l, wherein the compound (iv) is melamine or derivative thereof.
7. A resin composition according to claim l, wherein the polyamide (iii) is at least one crystalline aliphatic polyamide.
8. A resin composition according to claim 7,the crystalline aliphatic polyamide is at least one polyamide selected from the group consisting of polyamide 46, polyamide 6, polyamide 66, polyamide 11, polyamide 12 and polyamide 6/10.
9. A resin composition according to claim 8, wherein the crystalline aliphatic polyamide comprises about 30-about 95 % by weight of polyamide 6 and about 70-about 5 % by weight of complementary polyamide 66 based on total amount of aliphatic polyamides.
10. A resin composition according to claim l, wherein the polyamide (iii) is a mixture of at least one crystalline aliphatic polyamide and at least one aromatic polyamide.
11. A resin composition according to claim 10, wherein the polyamide comprises about 70-about 99.5 % by weight of at least one crystalline alipha-tic polyamide selected from polyamide 46, polyamide 6 and polyamide 66 and about 30-about 0.5 % by weight of aromatic polyamide based on total amount of polyamides.
12. A resin composition according to claim 1, wherein polyphenylene ether (ii) is at least one selected from the group consisting of poly(2,6-dimethyl 1,4-phenylene) ether and 2,6-dimethyl phenol-2,3,6-trimethyl phenol copolymer.
13. A resin composition according to claim 5, wherein lactam is .epsilon.-caprolactam.
14. A resin composition according to claim 1, which contains about 1 - 70 parts by weight of an inorganic filler based on 100 parts by weight of the resin composition.
15. A resin composition according to claim 14, wherein the inorganic filler is at least one inorganic filler selected from the group consisting of talc, titanium oxide, clay, magnesium hydroxide, potassium titanate whisker and glass fiber.
16. A resin composition according to claim 15, wherein the inorganic filler is combination of talc and glass fiber.
17. A resin composition according to claim 1, which contains about 1 - 50 parts by weight of a impact strength improver based on 100 parts by weight of the resin composition.
Applications Claiming Priority (2)
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JP341454/89 | 1989-12-27 | ||
JP1341454A JP2841601B2 (en) | 1989-12-27 | 1989-12-27 | Thermoplastic resin composition |
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CA2031472A1 true CA2031472A1 (en) | 1991-06-28 |
Family
ID=18346200
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CA002031472A Abandoned CA2031472A1 (en) | 1989-12-27 | 1990-12-04 | Thermoplastic resin composition |
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US (1) | US5182336A (en) |
EP (1) | EP0435504A3 (en) |
JP (1) | JP2841601B2 (en) |
CA (1) | CA2031472A1 (en) |
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EP0302897A1 (en) * | 1987-02-12 | 1989-02-15 | General Electric Company | Polyphenylene ether polyamide blends |
JPS6432152A (en) * | 1987-07-29 | 1989-02-02 | Yokogawa Electric Corp | Moisture meter |
DE3732907A1 (en) * | 1987-09-30 | 1989-04-13 | Basf Ag | SELF-EXTINGUISHING, THERMOPLASTIC POLYPHENYLENETHER-POLYAMIDE MOLDING MATERIALS AND THEIR USE FOR THE PRODUCTION OF MOLDED BODIES |
JPH01139642A (en) * | 1987-11-26 | 1989-06-01 | Mitsubishi Kasei Corp | Resin composition |
JP2671382B2 (en) * | 1988-05-24 | 1997-10-29 | 住友化学工業株式会社 | Thermoplastic resin composition |
JPH02132152A (en) * | 1988-11-11 | 1990-05-21 | Sumitomo Chem Co Ltd | Resin composition |
JP2715499B2 (en) * | 1988-12-15 | 1998-02-18 | 住友化学工業株式会社 | Thermoplastic resin composition |
-
1989
- 1989-12-27 JP JP1341454A patent/JP2841601B2/en not_active Expired - Fee Related
-
1990
- 1990-12-04 CA CA002031472A patent/CA2031472A1/en not_active Abandoned
- 1990-12-07 US US07/624,304 patent/US5182336A/en not_active Expired - Fee Related
- 1990-12-11 EP EP19900313421 patent/EP0435504A3/en not_active Ceased
Also Published As
Publication number | Publication date |
---|---|
US5182336A (en) | 1993-01-26 |
JP2841601B2 (en) | 1998-12-24 |
EP0435504A2 (en) | 1991-07-03 |
EP0435504A3 (en) | 1992-10-28 |
JPH03199258A (en) | 1991-08-30 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
FZDE | Discontinued |