CA2435430A1 - Two-component polyurethane binders as adhesion promoters - Google Patents
Two-component polyurethane binders as adhesion promoters Download PDFInfo
- Publication number
- CA2435430A1 CA2435430A1 CA002435430A CA2435430A CA2435430A1 CA 2435430 A1 CA2435430 A1 CA 2435430A1 CA 002435430 A CA002435430 A CA 002435430A CA 2435430 A CA2435430 A CA 2435430A CA 2435430 A1 CA2435430 A1 CA 2435430A1
- Authority
- CA
- Canada
- Prior art keywords
- use according
- group
- isocyanate
- polyisocyanate
- organic
- 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.)
- Granted
Links
- 239000004814 polyurethane Substances 0.000 title claims abstract 3
- 229920002635 polyurethane Polymers 0.000 title claims abstract 3
- 239000002318 adhesion promoter Substances 0.000 title claims 3
- 239000011230 binding agent Substances 0.000 title claims 2
- 239000005056 polyisocyanate Substances 0.000 claims abstract 10
- 229920001228 polyisocyanate Polymers 0.000 claims abstract 10
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract 4
- 239000011347 resin Substances 0.000 claims abstract 3
- 229920005989 resin Polymers 0.000 claims abstract 3
- 238000000576 coating method Methods 0.000 claims 6
- 239000000758 substrate Substances 0.000 claims 6
- 239000011248 coating agent Substances 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims 1
- 239000005058 Isophorone diisocyanate Substances 0.000 claims 1
- 239000004793 Polystyrene Substances 0.000 claims 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 claims 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 claims 1
- 239000011521 glass Substances 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 101150009274 nhr-1 gene Proteins 0.000 claims 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims 1
- 239000004417 polycarbonate Substances 0.000 claims 1
- 229920000515 polycarbonate Polymers 0.000 claims 1
- 239000004926 polymethyl methacrylate Substances 0.000 claims 1
- 229920002223 polystyrene Polymers 0.000 claims 1
- 239000004800 polyvinyl chloride Substances 0.000 claims 1
- 229920000915 polyvinyl chloride Polymers 0.000 claims 1
- 229910052710 silicon Inorganic materials 0.000 claims 1
- 239000010703 silicon Substances 0.000 claims 1
- 239000007767 bonding agent Substances 0.000 abstract 3
- 239000000470 constituent Substances 0.000 abstract 2
- 239000000853 adhesive Substances 0.000 abstract 1
- 230000001070 adhesive effect Effects 0.000 abstract 1
- -1 alkoxy silane Chemical compound 0.000 abstract 1
- 239000004922 lacquer Substances 0.000 abstract 1
- 229910000077 silane Inorganic materials 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000002966 varnish Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/80—Masked polyisocyanates
- C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
- C08G18/8083—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with compounds containing at least one heteroatom other than oxygen or nitrogen
- C08G18/809—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with compounds containing at least one heteroatom other than oxygen or nitrogen containing silicon
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6633—Compounds of group C08G18/42
- C08G18/6637—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/664—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
- C08G18/6644—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203 having at least three hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/06—Polyurethanes from polyesters
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
Abstract
The invention relates to the use of polyurethane bonding agents as adhesives, said bonding agents having two constituents and containing a solvent. Said bonding agents also contain a hardening constituent consisting of an addition product of a polyisocyanate with an alkoxy silane and a resin for lacquers and varnishes which reacts in relation to isocyanate groups.
Claims (12)
1. Use of solventborne two-component polyurethane binders comprising 1. a curing component (A) comprising an adduct of at least one organic polyisocyanate (B) having an average NCO
functionality of from 2.5 to 5.0 and an isocyanate content of from 8 to 27% by weight and an alkoxysilane (C) having at least one isocyanate-reactive group of the general formula (I) Q-Z-SiXaY3-a in which Q is an isocyanate-reactive group, Z is a linear or branched C1-C12 alkylene group, X is a hydrolyzable group, preferably C1-C4 alkoxy, Y is identical or different C1-C4 alkyl groups, and a is an integer from 1 to 3, and
functionality of from 2.5 to 5.0 and an isocyanate content of from 8 to 27% by weight and an alkoxysilane (C) having at least one isocyanate-reactive group of the general formula (I) Q-Z-SiXaY3-a in which Q is an isocyanate-reactive group, Z is a linear or branched C1-C12 alkylene group, X is a hydrolyzable group, preferably C1-C4 alkoxy, Y is identical or different C1-C4 alkyl groups, and a is an integer from 1 to 3, and
2. an isocyanate-reactive film-forming resin (D), as adhesion promoters.
2. The use according to claim 1, characterized in that the ratio of the isocyanate-reactive groups of the film-forming resin (D) to the isocyanate groups of the curing agent (A) lies between 0.5 : 1 to 2 : 1.
2. The use according to claim 1, characterized in that the ratio of the isocyanate-reactive groups of the film-forming resin (D) to the isocyanate groups of the curing agent (A) lies between 0.5 : 1 to 2 : 1.
3. The use according to claim 1, characterized in that the polyisocyanate (B) containing in the curing component (A) has an average NCO functionality of from 2.3 to 4.5 and an isocyanate group content of from 11.0 to 24.0% by weight.
4. The use according to claim 1, characterized in that the organic polyisocyanate (B) stands for polyisocyanates or polyisocyanate mixtures containing exclusively aliphatically and/or cycloaliphatically attached isocyanate groups.
5. The use according to claim 1, characterized in that the organic polyisocyanate (B) stands for polyisocyanates or polyisocyanate mixtures having biuret or isocyanurate structure based on HDI, IPDI and/or 4,4'-diisocyanatodicyclohexylmethane.
6. The use according to claim 1, characterized in that organic polyisocyanates (B) is reacted with alkoxysilanes (C) in a molar NCO/Q ratio of 1 : 0.01 to 0.75, Q having the definition described in general formula (I).
7. The use according to claim 1, characterized in that alkoxysilanes (C) are compounds of the general formula (I) Q-Z-Si X a Y3-a (I), in which Q is OH, SH or NHR1, where R1 is a C1-C12 alkyl group or C6-C20 aryl group or is -Z-SiX a Y3-a, Z is a linear or branched C1-C4 alkylene group, X is a C1-C4 alkoxy group, Y is identical or different C1-C4 alkyl groups, and a is an integer from 1 to 3.
8. The use according to claim 1, characterized in that the adhesion promoter is applied to a substrate and subsequently a coating is applied.
9. The use according to claim 8, characterized in that the substrate is selected from the group of the polymeric substrates, metal substrates or glass substrates.
10. The use according to claim 9, characterized in that the polymeric substrate is selected from the group of polycarbonate, polymethyl methacrylate, polystyrene, polyvinylcyclohexane and copolymers thereof, polyvinylchloride or blends thereof.
11. The use according to claim 8, characterized in that the coating is selected from the group of inorganic coatings, organic coatings or inorganic-organic hydride coatings.
12. The use according to claim 11, characterized in that the inorganic coating is silicon-containing.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10103027A DE10103027A1 (en) | 2001-01-24 | 2001-01-24 | Adhesion promoter, e.g. for improving adhesion of silicon-based protective coatings to polymeric substrates, comprising two-component polyurethane binder based on alkoxysilane-modified polyisocyanate |
DE10103027.4 | 2001-01-24 | ||
PCT/EP2002/000205 WO2002059224A1 (en) | 2001-01-24 | 2002-01-11 | Polyurethane bonding agent having two constituents and used as an adhesive |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2435430A1 true CA2435430A1 (en) | 2002-08-01 |
CA2435430C CA2435430C (en) | 2011-12-13 |
Family
ID=7671531
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA2435430A Expired - Fee Related CA2435430C (en) | 2001-01-24 | 2002-01-11 | Two-component polyurethane binders as adhesion promoters |
Country Status (14)
Country | Link |
---|---|
US (1) | US6756464B2 (en) |
EP (1) | EP1356004A1 (en) |
JP (1) | JP2004525213A (en) |
KR (1) | KR20040030494A (en) |
CN (1) | CN1243808C (en) |
CA (1) | CA2435430C (en) |
CZ (1) | CZ20032033A3 (en) |
DE (1) | DE10103027A1 (en) |
HK (1) | HK1064697A1 (en) |
HU (1) | HUP0302795A3 (en) |
MX (1) | MXPA03006536A (en) |
PL (1) | PL205153B1 (en) |
SK (1) | SK9182003A3 (en) |
WO (1) | WO2002059224A1 (en) |
Families Citing this family (32)
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DE10103026A1 (en) * | 2001-01-24 | 2002-07-25 | Bayer Ag | A two-layer protective coating useful for protecting coated bases against mechanical damage comprises a first layer of a two component polyurethane primer and a second layer with (in)organic coating |
EP1502927A1 (en) * | 2003-07-31 | 2005-02-02 | Sika Technology AG | Isocyanate free primer composition for glass and glass-ceramics |
US20050238899A1 (en) * | 2004-04-27 | 2005-10-27 | Isao Nagata | High solids clearcoat compositions containing silane functional compounds |
DE102004050746A1 (en) * | 2004-10-19 | 2006-04-20 | Basf Coatings Ag | Thermally hardened coating agents, useful for coating plastics, comprises a mixture of polymethacrylate-copolymerisate and adduct of polyisocyanate and alkoxysilane; catalyst for cross-linking siloxane units; and aprotic solvent |
DE102006006656A1 (en) * | 2005-08-26 | 2007-03-01 | Degussa Ag | Silane-containing binder for composites |
CN101096472A (en) * | 2006-06-26 | 2008-01-02 | 上海飞凯光电材料有限公司 | Adhesive property promoter for radiation curing material |
US8569438B2 (en) * | 2006-12-19 | 2013-10-29 | Basf Coatings Gmbh | Coating agents having high scratch resistance and weathering stability |
CN101050223B (en) * | 2007-05-14 | 2010-12-01 | 张群朝 | Tripolymer in isocyanic ester class modified by silicane or functional polusiloxane, preparation method |
DE102007061855A1 (en) | 2007-12-19 | 2009-06-25 | Basf Coatings Ag | Coating agent with high scratch resistance and weathering stability |
DE102007061856A1 (en) * | 2007-12-19 | 2009-06-25 | Basf Coatings Ag | Coating agent with high scratch resistance and weathering stability |
DE102007061854A1 (en) | 2007-12-19 | 2009-06-25 | Basf Coatings Ag | Coating agent with high scratch resistance and weathering stability |
WO2009086256A1 (en) * | 2007-12-27 | 2009-07-09 | E. I. Du Pont De Nemours And Company | Adhesion-promoting agent for protective coatings |
DE102008030304A1 (en) | 2008-06-25 | 2009-12-31 | Basf Coatings Ag | Use of partially silanated polyisocyanate-based compounds as crosslinking agents in coating compositions and coating compositions containing the compounds |
DE102008050916A1 (en) * | 2008-10-10 | 2010-04-15 | Basf Coatings Ag | Two-component polyurethane lacquer containing silanized polyisocyanate hardeners, process for the preparation of silanized polyisocyanate hardeners and hardeners prepared by the process |
DE102010005994B4 (en) * | 2010-01-27 | 2022-07-28 | Tianjin Shenglong Fibre Co., Ltd. | Method for producing a hybrid upholstery element, in particular a seat and backrest upholstery element for use in a motor vehicle, an upholstery element and a vehicle seat with an upholstery element. |
US8133964B2 (en) * | 2010-06-29 | 2012-03-13 | Science Applications International Corporation | Single-component coating having alkoxysilane-terminated N-substituted urea resins |
CN102416373B (en) * | 2011-09-22 | 2014-03-12 | 东莞广泽汽车饰件有限公司 | High gloss coating process of surface of plastic substrate |
EP2602109A3 (en) | 2011-12-06 | 2013-07-10 | Alporit AG | Styrene polymer foam compound body |
CN104583260B (en) * | 2012-09-04 | 2017-10-20 | 科思创德国股份有限公司 | The adhesive of silane-functional with thiocarbamate structure |
EP2871194B1 (en) | 2013-11-12 | 2016-08-03 | nolax AG | Dual component adhesive |
KR101688938B1 (en) * | 2014-09-29 | 2016-12-23 | 한경대학교 산학협력단 | Method for preparing of environment-friendly flame retardancy polyurethane resin including phosphorus |
US10190020B2 (en) | 2014-10-22 | 2019-01-29 | The United States Of America, As Represented By The Secretary Of The Navy | Siloxane-based coatings containing polymers with urea linkages and terminal alkoxysilanes |
WO2016064481A1 (en) * | 2014-10-22 | 2016-04-28 | The Government Of The United States Of America, As Represented By The Secretary Of The Navy | Two-component siloxane-based coatings containing polymers with urea linkages and terminal alkoxysilanes |
CN107922574B (en) | 2015-09-09 | 2021-02-26 | 科思创德国股份有限公司 | Scratch-resistant water-based 2K PU coating |
CN108026237B (en) * | 2015-09-09 | 2020-12-22 | 科思创德国股份有限公司 | Scratch-resistant two-component polyurethane coating |
FR3054837B1 (en) | 2016-08-08 | 2020-06-19 | Bostik Sa | PROCESS FOR THE SYNTHESIS OF SILYLATED POLYURETHANES AND COMPOSITION OF SILYLATED POLYURETHANES |
EP3505549A1 (en) * | 2017-12-28 | 2019-07-03 | Covestro Deutschland AG | Silane-modified polyurea compounds based on polyisocyanates with isocyanurate and allophanate groups |
CN112204063B (en) * | 2018-04-30 | 2022-12-09 | 陶氏环球技术有限责任公司 | Two-component adhesive composition based on isocyanate-terminated silanes and method for producing same |
EP3760658A1 (en) * | 2019-07-03 | 2021-01-06 | Covestro Deutschland AG | Resistant 2k-pur coatings |
CN111363460B (en) * | 2020-03-18 | 2021-11-26 | 深圳飞扬骏研新材料股份有限公司 | Environment-friendly baking-free finishing varnish for spraying, preparation method and curing material |
WO2023117034A1 (en) * | 2020-12-17 | 2023-06-29 | Akzo Nobel Coatings International B.V. | Multi-layer coating system for polycarbonate substrates |
CN114479626B (en) * | 2022-01-26 | 2023-07-07 | 广州市捷晟智谷颜料有限公司 | Coating composition |
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-
2001
- 2001-01-24 DE DE10103027A patent/DE10103027A1/en not_active Withdrawn
-
2002
- 2002-01-11 MX MXPA03006536A patent/MXPA03006536A/en active IP Right Grant
- 2002-01-11 CA CA2435430A patent/CA2435430C/en not_active Expired - Fee Related
- 2002-01-11 PL PL361766A patent/PL205153B1/en not_active IP Right Cessation
- 2002-01-11 KR KR10-2003-7009731A patent/KR20040030494A/en not_active Application Discontinuation
- 2002-01-11 HU HU0302795A patent/HUP0302795A3/en unknown
- 2002-01-11 CN CNB028040880A patent/CN1243808C/en not_active Expired - Fee Related
- 2002-01-11 JP JP2002559513A patent/JP2004525213A/en not_active Ceased
- 2002-01-11 WO PCT/EP2002/000205 patent/WO2002059224A1/en active Application Filing
- 2002-01-11 EP EP02708272A patent/EP1356004A1/en not_active Withdrawn
- 2002-01-11 CZ CZ20032033A patent/CZ20032033A3/en unknown
- 2002-01-11 SK SK918-2003A patent/SK9182003A3/en unknown
- 2002-01-22 US US10/054,386 patent/US6756464B2/en not_active Expired - Fee Related
-
2004
- 2004-09-30 HK HK04107542A patent/HK1064697A1/en not_active IP Right Cessation
Also Published As
Publication number | Publication date |
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HK1064697A1 (en) | 2005-02-04 |
MXPA03006536A (en) | 2004-06-25 |
PL205153B1 (en) | 2010-03-31 |
HUP0302795A3 (en) | 2012-09-28 |
CZ20032033A3 (en) | 2003-10-15 |
HUP0302795A2 (en) | 2003-11-28 |
US6756464B2 (en) | 2004-06-29 |
EP1356004A1 (en) | 2003-10-29 |
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PL361766A1 (en) | 2004-10-04 |
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WO2002059224A1 (en) | 2002-08-01 |
JP2004525213A (en) | 2004-08-19 |
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CA2435430C (en) | 2011-12-13 |
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CN1243808C (en) | 2006-03-01 |
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