WO2000034381A1 - Conductive, low warp polyetherimide resin compositions - Google Patents
Conductive, low warp polyetherimide resin compositions Download PDFInfo
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- WO2000034381A1 WO2000034381A1 PCT/US1999/024295 US9924295W WO0034381A1 WO 2000034381 A1 WO2000034381 A1 WO 2000034381A1 US 9924295 W US9924295 W US 9924295W WO 0034381 A1 WO0034381 A1 WO 0034381A1
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- WIPO (PCT)
- Prior art keywords
- composition
- filler
- present
- amount
- polyetherimide
- Prior art date
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- 229920001601 polyetherimide Polymers 0.000 title claims abstract description 42
- 239000004697 Polyetherimide Substances 0.000 title claims abstract description 41
- 239000011342 resin composition Substances 0.000 title description 8
- 239000000203 mixture Substances 0.000 claims abstract description 98
- 239000000945 filler Substances 0.000 claims abstract description 48
- 239000011231 conductive filler Substances 0.000 claims abstract description 28
- 229920005989 resin Polymers 0.000 claims abstract description 14
- 239000011347 resin Substances 0.000 claims abstract description 14
- 229920006026 co-polymeric resin Polymers 0.000 claims abstract description 7
- 239000004917 carbon fiber Substances 0.000 claims description 15
- 229920000049 Carbon (fiber) Polymers 0.000 claims description 14
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 11
- 239000010445 mica Substances 0.000 claims description 11
- 229910052618 mica group Inorganic materials 0.000 claims description 11
- -1 polyethylene Polymers 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000011521 glass Substances 0.000 claims description 6
- 239000004698 Polyethylene Substances 0.000 claims description 5
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical group C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical group [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229920000573 polyethylene Polymers 0.000 claims description 4
- 229920000098 polyolefin Polymers 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- QYFRTHZXAGSYGT-UHFFFAOYSA-L hexaaluminum dipotassium dioxosilane oxygen(2-) difluoride hydrate Chemical compound O.[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[F-].[F-].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[K+].[K+].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O QYFRTHZXAGSYGT-UHFFFAOYSA-L 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 150000003462 sulfoxides Chemical class 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 14
- 239000000463 material Substances 0.000 description 12
- 238000000465 moulding Methods 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000004985 diamines Chemical class 0.000 description 6
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 6
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 5
- 239000000654 additive Substances 0.000 description 4
- 238000000137 annealing Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- FLZYQMOKBVFXJS-UHFFFAOYSA-N 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoic acid Chemical compound CC1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O FLZYQMOKBVFXJS-UHFFFAOYSA-N 0.000 description 2
- SGEWZUYVXQESSB-UHFFFAOYSA-N 3-methylheptane-1,7-diamine Chemical compound NCCC(C)CCCCN SGEWZUYVXQESSB-UHFFFAOYSA-N 0.000 description 2
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 2
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 239000006082 mold release agent Substances 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 150000008442 polyphenolic compounds Chemical class 0.000 description 2
- 235000013824 polyphenols Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000012756 surface treatment agent Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- RGASRBUYZODJTG-UHFFFAOYSA-N 1,1-bis(2,4-ditert-butylphenyl)-2,2-bis(hydroxymethyl)propane-1,3-diol dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O.C(C)(C)(C)C1=C(C=CC(=C1)C(C)(C)C)C(O)(C(CO)(CO)CO)C1=C(C=C(C=C1)C(C)(C)C)C(C)(C)C RGASRBUYZODJTG-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- GXURZKWLMYOCDX-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O.OCC(CO)(CO)CO GXURZKWLMYOCDX-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- YXOKJIRTNWHPFS-UHFFFAOYSA-N 2,5-dimethylhexane-1,6-diamine Chemical compound NCC(C)CCC(C)CN YXOKJIRTNWHPFS-UHFFFAOYSA-N 0.000 description 1
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 description 1
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 1
- POTQBGGWSWSMCX-UHFFFAOYSA-N 3-[2-(3-aminopropoxy)ethoxy]propan-1-amine Chemical compound NCCCOCCOCCCN POTQBGGWSWSMCX-UHFFFAOYSA-N 0.000 description 1
- WQYOBFRCLOZCRC-UHFFFAOYSA-N 3-[4-[4-(2,3-dicarboxyphenoxy)benzoyl]phenoxy]phthalic acid Chemical compound OC(=O)C1=CC=CC(OC=2C=CC(=CC=2)C(=O)C=2C=CC(OC=3C(=C(C(O)=O)C=CC=3)C(O)=O)=CC=2)=C1C(O)=O WQYOBFRCLOZCRC-UHFFFAOYSA-N 0.000 description 1
- ARNUDBXPYOXUQO-UHFFFAOYSA-N 3-[4-[4-(3,4-dicarboxyphenoxy)benzoyl]phenoxy]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC=C(C(=O)C=2C=CC(OC=3C(=C(C(O)=O)C=CC=3)C(O)=O)=CC=2)C=C1 ARNUDBXPYOXUQO-UHFFFAOYSA-N 0.000 description 1
- YEEIWUUBRYZFEH-UHFFFAOYSA-N 3-methoxyhexane-1,6-diamine Chemical compound NCCC(OC)CCCN YEEIWUUBRYZFEH-UHFFFAOYSA-N 0.000 description 1
- ZWIBGDOHXGXHEV-UHFFFAOYSA-N 4,4-dimethylheptane-1,7-diamine Chemical compound NCCCC(C)(C)CCCN ZWIBGDOHXGXHEV-UHFFFAOYSA-N 0.000 description 1
- WYHSHHJLHFEEFE-UHFFFAOYSA-N 4-(4-aminophenyl)-6,6-dimethylcyclohexa-1,3-dien-1-amine Chemical compound C1=C(N)C(C)(C)CC(C=2C=CC(N)=CC=2)=C1 WYHSHHJLHFEEFE-UHFFFAOYSA-N 0.000 description 1
- NJWZAJNQKJUEKC-UHFFFAOYSA-N 4-[4-[2-[4-[(1,3-dioxo-2-benzofuran-4-yl)oxy]phenyl]propan-2-yl]phenoxy]-2-benzofuran-1,3-dione Chemical compound C=1C=C(OC=2C=3C(=O)OC(=O)C=3C=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=CC2=C1C(=O)OC2=O NJWZAJNQKJUEKC-UHFFFAOYSA-N 0.000 description 1
- GAUNIEOSKKZOPV-UHFFFAOYSA-N 4-[4-[4-(3,4-dicarboxyphenoxy)benzoyl]phenoxy]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC=C(C(=O)C=2C=CC(OC=3C=C(C(C(O)=O)=CC=3)C(O)=O)=CC=2)C=C1 GAUNIEOSKKZOPV-UHFFFAOYSA-N 0.000 description 1
- MRTAEHMRKDVKMS-UHFFFAOYSA-N 4-[4-[4-(3,4-dicarboxyphenoxy)phenyl]sulfanylphenoxy]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC(C=C1)=CC=C1SC(C=C1)=CC=C1OC1=CC=C(C(O)=O)C(C(O)=O)=C1 MRTAEHMRKDVKMS-UHFFFAOYSA-N 0.000 description 1
- IPDXWXPSCKSIII-UHFFFAOYSA-N 4-propan-2-ylbenzene-1,3-diamine Chemical compound CC(C)C1=CC=C(N)C=C1N IPDXWXPSCKSIII-UHFFFAOYSA-N 0.000 description 1
- MQAHXEQUBNDFGI-UHFFFAOYSA-N 5-[4-[2-[4-[(1,3-dioxo-2-benzofuran-5-yl)oxy]phenyl]propan-2-yl]phenoxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC2=CC=C(C=C2)C(C)(C=2C=CC(OC=3C=C4C(=O)OC(=O)C4=CC=3)=CC=2)C)=C1 MQAHXEQUBNDFGI-UHFFFAOYSA-N 0.000 description 1
- MBRGOFWKNLPACT-UHFFFAOYSA-N 5-methylnonane-1,9-diamine Chemical compound NCCCCC(C)CCCCN MBRGOFWKNLPACT-UHFFFAOYSA-N 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 1
- 239000004734 Polyphenylene sulfide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 241001582429 Tetracis Species 0.000 description 1
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006085 branching agent Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 1
- CBLAIDIBZHTGLV-UHFFFAOYSA-N dodecane-2,11-diamine Chemical compound CC(N)CCCCCCCCC(C)N CBLAIDIBZHTGLV-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical compound NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- KMBPCQSCMCEPMU-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)CCCN KMBPCQSCMCEPMU-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 description 1
- CJYCVQJRVSAFKB-UHFFFAOYSA-N octadecane-1,18-diamine Chemical compound NCCCCCCCCCCCCCCCCCCN CJYCVQJRVSAFKB-UHFFFAOYSA-N 0.000 description 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 125000005000 thioaryl group Chemical group 0.000 description 1
- MZHULIWXRDLGRR-UHFFFAOYSA-N tridecyl 3-(3-oxo-3-tridecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCC MZHULIWXRDLGRR-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08K7/00—Use of ingredients characterised by shape
-
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
Definitions
- the present invention relates to conductive, low a ⁇ polyetherimide resin compositions. BACKGROUND OF THE INVENTION
- Polyetherimide resin compositions have been used to fabricate parts for numerous applications. Each application requires particular tensile and flexural properties, impact strength, heat distortion temperature, and resistance to wa ⁇ .
- U.S. Patent 4,455,410 provides a polyetherimide-polyphenylenesulfide blend having good flexural strength characteristics.
- U.S. Patent 3,983,093 provides polyetherimide compositions having improved solvent resistance and suitable for use in preparing films, molding compounds, coatings, and the like.
- a combination of low wa ⁇ and low surface resistance are required.
- the wa ⁇ of a given product is dependent upon composition, the geometry of the product and processing conditions such as molding temperature and pressure.
- the material For a material to be useful in computer chip tray applications, the material must provide low wa ⁇ properties and must possess a surface resisit y of less than about 10 6 ohms per square centimeter (ohms/cm 2 ). This is difficult to achieve because the Dolyetherimide is non-conductive and high levels of conductive materials, such as carbon fiber, added to achieve the desired low surface resistance may contribute to an increase in wa ⁇ .
- the present invention provides a polyetherimide composition having low wa ⁇ and conductive properties prepared by combining a polyetherimide resin or polyetherimide-copolymer resin and a filler composition wherein the filler composition comprises a plate-like filler and a conductive filler.
- the present invention provides a polyetherimide composition having low wa ⁇ and conductive properties prepared by combining a polyetherimide resin or polyetherimide-copolymer resin and a filler composition wherein the filler composition comprises a plate-like filler and a conductive filler.
- the polyetherimide compositions comprise a polyetherimide resin or polyetherimide-copolymer resin and a filler composition comprising a platelike filler material present in an amount sufficient to impart dimensional stability, in particular, low wa ⁇ , to the composition and a conductive filler present in an amount sufficient to impart conductive properties to the composition.
- polyetherimide resins useful in the compositions of the present invention are known compounds whose preparation and properties are described in U.S. Patent Nos. 3,803,085 and 3,905,942, each of which is inco ⁇ orated herein by reference.
- the polyetherimide used for preparing the compositions of this invention comprise about 10 to about 1000 or more, and more preferably about 10 to about 500 structural units, of the formula (I): wherein T is -0-, carbonyl, sulfur, sulfoxide or a residue of a bisphenol group of the formula -0-Z-O- wherein the divalent bonds of the -0- or the -0-Z-O- group are in the 3,3', 3,4', 4,3', or the 4,4' positions; Z includes, but is not limited to, a divalent radical of formulae (II):
- X includes, but is not limited to, divalent radicals of the formulae (III): -4-
- R includes, but is not limited to, a divalent organic radical: (a) aromatic hydrocarbon radicals having from 6 to about 20 carbon atoms and halogenated derivatives thereof, (b) alkyiene radicals having about 2 to about 20 carbon atoms, (c) cycioalkylene radicals having about 3 to about 20 carbon atoms, and (d) divalent radicals of the general formula (IV):
- the polyetherimide may be a copolymer which, in addition to the etherimide units described above, further contains polyimide structural units of the formula (VI):
- the polyetherimide can be prepared by any of the methods well known to those skilled in the art, including the reaction of an aromatic bis(ether anhydride) of the formula (VIII):
- the reactions can be carried out employing well-known solvents, e.g., o- dichlorobenzene, m-cresol/toluene and the like to effect interaction between the anhydride of formula (VIII) and the diamine of formula (IX), at temperatures of about 100°C to about 250°C.
- the polyetherimide can be prepared by melt polymerization of aromatic bis(ether anhydrides) and diamines accomplished by heating a mixture of the ingredients to elevated temperatures with concurrent stirring. Generally melt polymerizations employ temperatures of about 200°C to about 400°C. Chain stoppers and branching agents may also be employed in the reaction. Examples of specific aromatic bis(ether anhydrides) and organic diamines are disclosed, for example, in -U.S. Patent Nos. 3,972,902 and 4,455,410, which are incorporated herein by reference.
- aromatic bis(etheranhydride)s of formula (VIII) include: 2,2-bis [4-(3,4-dicarboxyphenoxy)phenyl]propane dianhydride; 4,4'- bis(3,4-dicarboxyphenoxy)diphenyl ether dianhydride; 4,4'-bis(3,4- dicarboxyphenoxy)diphenyl sulfide dianhydride; 4,4'-bis(3,4- dicarboxyphenoxy)benzophenone dianhydride; 4,4'-bis(3,4- dicarboxyphenoxy)diphenyl sulfone dianhydride; 2,2-bis[4-(2,3- dicarboxyphenoxy)phenyl]propane dianhydride; 4,4'-bis(2,3- dicarboxyphenoxy)diphenyl ether dianhydride; 4,4'-bis(2,3- dicarboxyphenoxy)diphenyl sulfide dianhydride; 4,4'-bis(2,3- di
- a preferred class of aromatic bis (etheranhydride)s included by formula (VIII) above includes, but is not limited to, compounds wherein T is of the formula (X):
- the bis(ether anhydride)s can be prepared by the hydrolysis, followed by dehydration, of the reaction product of a nitro substituted phenyi dinrtrile with a metal salt of dihydric phenol compound in the presence of a dipolar, aprotic solvent.
- Suitable organic diamines of formula (IX) include, for example: m- phenylenediamine; p-phenylenediamine; 4,4'-diaminodiphenylpropane, 4,4'- diaminodiphenylmethane (commonly named 4,4'-methylenedianiline); 4,4- diaminodiphenyl sulfide; 4,4'-diaminodiphenyl sulfone; 4,4'-diaminodiphenyl ether (commonly named 4,4'-oxydianiline); 1 ,5-diami ⁇ onaphthalene; 3,3- dimethylbenzidine; 3,3-dimethoxybenzidine; 2,4-bis (beta-amino-t- butyl)toluene; bis (p-beta-amino-t-butylphenyl)ether; bis(p-beta-methyl-o- aminophenyl)benzene; 1,3
- useful polyetherimides have a melt index of between 0.1 and 10 grams per minute (“g/min”), as measured by American Society for Testing Materials (“ASTM”) D1238 at 295°C, using a 6.6 kilogram (“kg”) weight.
- the polyetherimide resin of the present invention has a weight average molecular weight of from 10,000 to 150,000 grams per mole (“g/mole”). as measured by gel permeation chromatography, using a polystyrene standard.
- Such polyetherimide resins typically have an intrinsic viscosity [ ⁇ ] greater than about 0.2 deciliters per gram, preferably about 0.35 to about 0.7 deciliters per gram measured in m-cresol at 25 ⁇ C.
- the polyetherimide resin comprises structural units according to formula (I) wherein each R is independently paraphenylene or metaphenylene and T is a divalent radical of the formula (XII):
- Polyetherimide and polyetherimide-copolymers are suitable for the present invention, such as those disclosed in U.S. Patent 3,983,093, commonly assigned, which is hereby inco ⁇ orated herein in its entirety.
- Particularly preferred for compositions of the present invention are polyetherimide-pyromellitic dianhydride copolymer resins and polyetherimide resins available from General Electric.
- the polyetherimide resins and copolymers of this invention can be further blended with other high temperature thermoplastics.
- other amo ⁇ hous high glass transition temperature polymers such as polycarbonates, polyarylates, polyester carbonates, polysulfones, polyether sulfones, and polyphenylene ethers. Plate-jike Filler
- the plate-like filler may be any plate-like filler selected to impart dimensional stability, and in particular low wa ⁇ characteristics, to the composition, such as mica or flaked glass.
- Preferable mica fillers are the naturally occurring mica fillers such as phlogophite mica of the formula (XIII):
- a preferred plate-like flaked glass filler is borosilicate E glass.
- the particle size of the plate-like filler may range from a maximum dimension of from 5 to about 1000 microns, with about 20 to about 300 microns most preferred.
- the thickness of the plate-like filler is about 0.5 to about 300 microns.
- the plate-like fillers of the present invention may be treated to enhance performance as dimensional stabilizers.
- Suitable surface treatment agents include functionalized siianes such as amino, mercaptOi or epoxy functionaiized alkoxy siianes.
- Gamma-aminopropyltriethoxysilane is particularly preferred as a surface treatment agent.
- the plate-like filler and conductive filler are employed in relative amounts sufficient to impart the desired combination of low wa ⁇ and low surface resistivity to the composition
- the plate-like filler comprises about 1% to about 50% by weight based upon the total weight of the composition. More preferably tne Diate-like filler comprises about 5% to about 30% by weight based on the tctai weight of the composition. Most preferably, the plate-like filler comprises about 10% to about 20% by weight based on the total weight of the composition.
- the conductive filler may comprise any electrically conductive material capable of imparting sufficient electrical conductivity to the polyetherimide composition and which is compatible with polyetherimide.
- Suitable conductive materials include, but are not limited to, carbon fibers, carbon fibrils, conductive carbon powder, metal fibers, metal coated carbon fibers, especially nickel coated carbon fibers, metal flake, metal powder, or mixtures thereof and others, with materials exhibiting surface resistivities below about 10 6 ohms/cm 2 preferred.
- the conductive filler is a fibrous conductive filler such as carbon fiber, preferably having a diameter of about 1 to about 20 microns.
- the conductive filler material can be surface treated, preferably with a polyetherimide coating, to enhance performance.
- the conductive filler comprises about 9% to about 45% by weight of the total weight of the composition. In a most preferred embodiment, the conductive filler material comprises about 9% to about 15% by weight of the total weight of the composition.
- thermoplastic resin composition of the present invention may optionally also contain various additives, such as antioxidants, such as, for example, organophosphites, for example, tris(nonyl- phenyl)phosphite, tris(2,4-di-t-butylphenyl)phosphite, bis(2,4-di-t- butylphenyl)pentaerythritol diphosphite or distearyi pentaerythritol diphosphite, alkylated monophenols. polyphenols and alkylated reaction products of polyphenols with dienes.
- antioxidants such as, for example, organophosphites, for example, tris(nonyl- phenyl)phosphite, tris(2,4-di-t-butylphenyl)phosphite, bis(2,4-di-t- butylphenyl)pentaerythritol diphosphite or di
- mold release agents include UV absorbers, stabilizers such as light stabilizers, lubricants, plasticizers, pigments, dyes, colorants, blowing agents, and flame retardants, among others.
- the preferred lubricants (i.e., mold release agents) for these compositions are polyolefin materials such as polyethylene.
- the polyolefin can be added at about 0.1% to about 5% by weight, preferably about 0.2% to about 1 % by weight based on the total weight of the composition.
- the total amount of all filler, including plate-like filler, conductive filler, and any other additives, present in the inventive composition is preferably about 50% and most preferably about 15% to about 30% by weight based on the total weight of the composition.
- compositions of the present invention exhibit a surface resistance of less than about 10 6 ohms/cm 2 , preferably less than about 10 4 ohms/cm 2 , and most preferably less than about 10 3 ohms/cm 2 . While the compositions of the present invention have application in a wide variety of physical shapes and forms, including use as films, molding compounds, and the like, the surface resistivities achieved render the compositions particularly useful as electrostatic discharge materials for fabricating components such as computer chip trays. The compositions of the present invention possess good dimensional stability, i.e., exhibit low warp.
- wa ⁇ will partially depend on the geometry of the part and material processing, parts produced with the compositions of the present invention will exhibit less wa ⁇ than parts produced with resin compositions comprising only conductive filler or resin compositions comprising a blend of conductive filler with a non-platelike filler.
- compositions of the present invention are those disclosed in U. S. Patent Nos. 3,847,867, 3,850,885, 3,852,242, 3,855,178, and 3,983,093. These patents are incorporated herein by reference for the purpose of teaching, by way of illustration, general and specific methods for preparing polyetherimide for use in the compositions of this invention.
- the preparation of the compositions of the present invention is normally achieved by blending the ingredients under conditions for the formation of an intimate blend. Such conditions often include solution blending or melt mixing in single or twin screw type extruders, mixing bowl, roll, kneader, or similar mixing devices that can apply a shear to the components.
- Twin screw extruders are often preferred due to their more intensive mixing capability over single screw extruders. However, severe compounding or mixing conditions should be avoided as such processing can break the plate-like filler and conductive filler down resulting in reduced performance. It is often advantageous to apply a vacuum to the blend through at least one vent port in the extruder to remove volatile impurities in the composition.
- Examples 1-9 were prepared as set forth in Table 1, in order to illustrate specific polyetherimide resin compositions comprising plate-like filler and conductive filler in accordance with the present invention.
- Comparative Examples A-H were prepared as set forth in Table 2. It should be understood that the examples and comparative examples are given for the pu ⁇ ose of illustration and do not limit the invention. In the examples and comparative examples, all parts and percentages are by weight.
- Computer chip trays and disk-shaped sample parts were prepared from the compositions of the present invention (Examples 1-9) and from comparative compositions (Examples A-H). Processing conditions were as set forth in the Tables. After forming the compositions into computer chip trays or sample disks, wa ⁇ on molding and wa ⁇ on annealing was determined Wa ⁇ on molding and wa ⁇ on annealing was measured using a "wa ⁇ test," which is performed by placing a sample on a flat surface and measuring the maximum height of the bottom surface both after molding and after annealing. Surface resistivity was determined using ASTM Test Method D157 using the 803B Surface Resistivity meter commercially available from ETS Co ⁇ oration.
- mice 1 phlogophite available from Suzorite Corporation as 150S.
- 'Mica 2 phlogophite available from Suzorite Corporation as 150 NY.
- Polyetherimide polymer available from General Electric.
- Molding condition for 1/16fb x 4fb disk is 750 * F; 500 psi hold pressure, 20 s cycle time, mold temp 350'
- Tables 1 and 2 show that disk-shaped parts formed with the poiyetherimide-pyromellitic dianhydride copolymer compositions of the present invention comprising about 20% mica filler and about 10% carbon fiber filler had the minimum (undetectable) wa ⁇ on molding and the minimum warp on annealing at temperatures of 350°F, as illustrated in Examples 7, 8, and 9, with surface resistivities of less than 10 ⁇ ohms/cm 2 .
- disk-shaped parts formed with compositions that were outside the scope of the present invention did not possess the advantageous combination of low warp and conductive (i.e., low surface resistivity) properties obtained with the compositions of the present invention.
- a disk-shape part was formed from a poiyetherimide-pyromellitic dianhydride copolymer composition comprising about 20% mica filler with about 8% carbon fiber filler.
- the part prepared with the composition of Comparative Example H exhibited adequate wa ⁇ properties but provided a surface resistivity of 10 12 ohms/cm 2 , which does not provide a conductivity suitable for many applications.
- the present inventors have shown that conductive filler and plate-like filler have significant effects on warp. Increasing the amount of conductive filler increases wa ⁇ while increasing the amount of plate-like filler material decreases warp. At the same time, however, a minimum amount of conductive filler material is necessary to impart the desired electrical conductivity to the compositions.
- the polyetherimide and polyetherimide- copolymer compositions of the present invention provide a balance of low wa ⁇ and low surface resistivity that render the compositions useful for applications requiring both dimensional stability and conductivity.
- compositions of the present invention are particularly suitable for forming computer chip trays and printed circuit board carriers, which much be dimensionaliy stable (i.e., exhibit low wa ⁇ ) and provide a surface resisitivy of less than about 10 6 ohms/cm 2 .
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
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JP2000586822A JP2002531668A (en) | 1998-12-09 | 1999-10-18 | Conductive and low warpage polyetherimide resin composition |
EP99954992A EP1141116A1 (en) | 1998-12-09 | 1999-10-18 | Conductive, low warp polyetherimide resin compositions |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US09/208,073 | 1998-12-09 | ||
US09/208,073 US6610773B1 (en) | 1998-12-09 | 1998-12-09 | Conductive, low warp polyetherimide resin compositions |
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WO2000034381A1 true WO2000034381A1 (en) | 2000-06-15 |
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PCT/US1999/024295 WO2000034381A1 (en) | 1998-12-09 | 1999-10-18 | Conductive, low warp polyetherimide resin compositions |
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US (1) | US6610773B1 (en) |
EP (1) | EP1141116A1 (en) |
JP (1) | JP2002531668A (en) |
WO (1) | WO2000034381A1 (en) |
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US7247822B2 (en) * | 2004-02-05 | 2007-07-24 | Methode Electronics, Inc. | Carbon fiber heating element assembly and methods for making |
US8663524B2 (en) * | 2009-05-12 | 2014-03-04 | Miller Waste Mills | Controlled geometry composite micro pellets for use in compression molding |
US9005748B1 (en) | 2011-03-04 | 2015-04-14 | Insulating Coatings Of America, Inc. | Coating containing borosilicate flake glass |
KR20170131575A (en) | 2015-03-25 | 2017-11-29 | 사빅 글로벌 테크놀러지스 비.브이. | Poly (arylene sulfide) blends and articles made therefrom |
Citations (3)
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JPH04342754A (en) * | 1991-05-20 | 1992-11-30 | Toyobo Co Ltd | Polyester resin composition |
EP0564660A1 (en) * | 1991-10-25 | 1993-10-13 | MITSUI TOATSU CHEMICALS, Inc. | Tray for integrated circuits |
JPH07242286A (en) * | 1994-03-01 | 1995-09-19 | Plus Teku Kk | Heat-resistant, electroconductive resin composition and heat-resistant tray made of this composition |
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US3847867A (en) | 1971-01-20 | 1974-11-12 | Gen Electric | Polyetherimides |
US3972902A (en) | 1971-01-20 | 1976-08-03 | General Electric Company | 4,4'-Isopropylidene-bis(3- and 4-phenyleneoxyphthalic anhydride) |
US3803085A (en) | 1972-12-29 | 1974-04-09 | Gen Electric | Method for making polyetherimides |
US3905942A (en) | 1973-06-22 | 1975-09-16 | Gen Electric | Method for making polyetherimides and products produced thereby |
US3850885A (en) | 1973-11-23 | 1974-11-26 | Gen Electric | Method for making polyetherimides |
US3855178A (en) | 1973-12-03 | 1974-12-17 | Gen Electric | Method for making polyetherimides |
US3852242A (en) | 1973-12-03 | 1974-12-03 | Gen Electric | Method for making polyetherimide |
US3983093A (en) | 1975-05-19 | 1976-09-28 | General Electric Company | Novel polyetherimides |
US4404125A (en) | 1981-10-14 | 1983-09-13 | General Electric Company | Polyphenylene ether resin compositions for EMI electromagnetic interference shielding |
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NL8204288A (en) | 1982-11-05 | 1984-06-01 | Gen Electric | POLYMER MIX, METHOD FOR PREPARING THE POLYMER MIX, ARTICLES FORMED FROM THE POLYMER MIX. |
US4596670A (en) | 1983-10-25 | 1986-06-24 | General Electric Company | EMI shielding effectiveness of thermoplastics |
NL8401545A (en) | 1984-05-14 | 1985-12-02 | Gen Electric | POLYMER MIXTURE CONTAINING A POLYPHENYLENE ETHER AND A POLYAMIDE. |
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1998
- 1998-12-09 US US09/208,073 patent/US6610773B1/en not_active Expired - Lifetime
-
1999
- 1999-10-18 EP EP99954992A patent/EP1141116A1/en not_active Withdrawn
- 1999-10-18 JP JP2000586822A patent/JP2002531668A/en active Pending
- 1999-10-18 WO PCT/US1999/024295 patent/WO2000034381A1/en active Application Filing
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JPH04342754A (en) * | 1991-05-20 | 1992-11-30 | Toyobo Co Ltd | Polyester resin composition |
EP0564660A1 (en) * | 1991-10-25 | 1993-10-13 | MITSUI TOATSU CHEMICALS, Inc. | Tray for integrated circuits |
JPH07242286A (en) * | 1994-03-01 | 1995-09-19 | Plus Teku Kk | Heat-resistant, electroconductive resin composition and heat-resistant tray made of this composition |
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DATABASE WPI Section Ch Week 199302, Derwent World Patents Index; Class A23, AN 1993-014147, XP002129513 * |
DATABASE WPI Section Ch Week 199546, Derwent World Patents Index; Class A23, AN 1995-354994, XP002129512 * |
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US6610773B1 (en) | 2003-08-26 |
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