WO1994024186B1 - Color-clear composite coatings having improved intercoat adhesion - Google Patents
Color-clear composite coatings having improved intercoat adhesionInfo
- Publication number
- WO1994024186B1 WO1994024186B1 PCT/US1994/002736 US9402736W WO9424186B1 WO 1994024186 B1 WO1994024186 B1 WO 1994024186B1 US 9402736 W US9402736 W US 9402736W WO 9424186 B1 WO9424186 B1 WO 9424186B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- carbon atoms
- bonded
- pendant groups
- containing acrylic
- Prior art date
Links
- 239000002131 composite material Substances 0.000 title claims abstract 3
- 229920000642 polymer Polymers 0.000 claims abstract 4
- 239000003795 chemical substances by application Substances 0.000 claims abstract 3
- 239000000203 mixture Substances 0.000 claims 11
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 125000004432 carbon atoms Chemical group C* 0.000 claims 10
- 238000000034 method Methods 0.000 claims 10
- 125000003700 epoxy group Chemical group 0.000 claims 8
- 229920001577 copolymer Polymers 0.000 claims 7
- 239000004593 Epoxy Substances 0.000 claims 4
- 239000000758 substrate Substances 0.000 claims 4
- VOZRXNHHFUQHIL-UHFFFAOYSA-N Glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 239000000178 monomer Substances 0.000 claims 2
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 claims 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims 1
- 239000011248 coating agent Substances 0.000 claims 1
- 238000000576 coating method Methods 0.000 claims 1
- 229920000058 polyacrylate Polymers 0.000 claims 1
- 239000008199 coating composition Substances 0.000 abstract 2
- 229920000647 polyepoxide Polymers 0.000 abstract 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 abstract 1
Abstract
Curable coating compositions based on polyepoxide-containing polymers and polyacid curing agents are disclosed. The polyepoxide-containing polymers contain one or more pendant groups of carbamate, urea or urethane groups. The coating compositions are useful as clear coats in composite color plus clear coatings where the pendant groups provide for better intercoat adhesion.
Claims
1. A curable composition comprising an epoxy group- containing acrylic copolymer having pendant groups of the structure
H H
I I
X - C - N - R or - N - C - O - R'
II II O O
I wherein X is -N or -0; R is H or an alkyl of 1-18 carbon atoms, or R is bonded to X and forms part of a five- or six-membered ring; and R' is an alkyl of 1-18 carbon atoms, and a polyacid curing agent which is a carboxylic acid group-containing oligomer or polymer.
2. The composition of claim 1 where R is H or alkyl of 1-6 carbon atoms or R is bonded to X and forms part of a 5 or 6 membered ring and R' is alkyl of 1-6 carbon atoms.
3. The curable composition of claim 2 in which X is -0 and R is selected from the group consisting of H and alkyl having 1-6 carbon atoms.
I
4. The curable composition of claim 2 in which X is N-, R is bonded to X and is -CH2-CH2.
5. The curable composition of claim 1 in which the epoxy group-containing acrylic copolymer is a copolymer of glycidyl acrylate or glycidyl methacrylate with at least one other copolymerizable ethylenically unsaturated monomer.
6. The curable composition of claim 1 in which the epoxy group-containing acrylic copolymer has an equivalent weight - 40 -
of from about 5000 to 100,000 based on equivalents of pendant groups.
7. The curable composition of claim 1 where for each equivalent of carboxyl there are 0.8 to 1.5 equivalents of epoxy.
8. A process for applying a composite coating to a substrate which comprises applying to the substrate a colored film-forming composition to form a base coat and applying to said base coat a clear film-forming composition to form a transparent top coat over the base coat, characterized in that the clear film-forming composition is a crosslinkable composition comprising an epoxy group-containing acrylic copolymer and a polyacid curing agent, wherein the epoxy group-containing acrylic copolymer contains one or more pendant groups of the structure:
H H
I I
X - C - N - or - N - C - O -
II II O 0
I where X is -N or -O.
9. The process of claim 8 wherein the pendant groups are of the structure:
H H
I I
X - C - N - R or - N - C - O - R1
II II 0 O
I where X is -N or -O and R is H or alkyl of 1-18 carbon atoms or R is bonded to X and forms part of a five- or six-membered ring and R' is alkyl of 1-18 carbon atoms.
10. The process of claim 9 where R is H or alkyl of 1-6 carbon atoms or R is bonded to X and forms part of a 5 or 6 membered ring and R' is alkyl of 1-6 carbon atoms. - 41 -
11. The process of claim 10 in which X is -0 and R is selected from the group consisting of H and alkyl having 1-6 carbon atoms.
I
12. The process of claim 10 in which X is N-, R is bonded to X and is -CH2-CH2.
13. The process of claim 13 in which the epoxy group- containing acrylic polymer is a copolymer of glycidyl acrylate or glycidyl methacrylate with at least one other copolymerizable ethylenically unsaturated monomer.
14. The process of claim 8 in which the polyepoxide- containing polymer has an equivalent weight of from about 5000 to 100,000 based on equivalents of pendant groups.
15. The process of claim 8 in which for each equivalent of carboxyl there are 0.8 to 1.5 equivalents of epoxy.
16. A substrate coated by the process of claim 8.
17. A substrate coated by the process of claim 9.
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP94913903A EP0695317A1 (en) | 1993-04-19 | 1994-03-14 | Color-clear composite coatings having improved intercoat adhesion |
JP6523181A JPH09509434A (en) | 1993-04-19 | 1994-03-14 | Color-clear composite coating with improved intercoat adhesion |
KR1019950704549A KR960701918A (en) | 1993-04-19 | 1994-03-14 | COLOR-CLEAR COMPOSITE COATINGS HAVING IMPROVED INTERCOAT ADHESION With Improved Inner Coating Adhesion |
AU65881/94A AU6588194A (en) | 1993-04-19 | 1994-03-14 | Color-clear composite coatings having improved intercoat adhesion |
CA002160777A CA2160777C (en) | 1993-04-19 | 1994-03-14 | Color-clear composite coatings having improved intercoat adhesion |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/047,904 US5384367A (en) | 1993-04-19 | 1993-04-19 | Carbamate urea or urethane-functional epoxy acrylic with polyacid |
US08/047,904 | 1993-04-19 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO1994024186A1 WO1994024186A1 (en) | 1994-10-27 |
WO1994024186B1 true WO1994024186B1 (en) | 1994-12-22 |
Family
ID=21951667
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1994/002736 WO1994024186A1 (en) | 1993-04-19 | 1994-03-14 | Color-clear composite coatings having improved intercoat adhesion |
Country Status (8)
Country | Link |
---|---|
US (2) | US5384367A (en) |
EP (1) | EP0695317A1 (en) |
JP (2) | JPH09509434A (en) |
KR (1) | KR960701918A (en) |
AU (1) | AU6588194A (en) |
CA (1) | CA2160777C (en) |
TW (1) | TW260699B (en) |
WO (1) | WO1994024186A1 (en) |
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-
1993
- 1993-04-19 US US08/047,904 patent/US5384367A/en not_active Expired - Fee Related
-
1994
- 1994-03-14 CA CA002160777A patent/CA2160777C/en not_active Expired - Fee Related
- 1994-03-14 WO PCT/US1994/002736 patent/WO1994024186A1/en not_active Application Discontinuation
- 1994-03-14 JP JP6523181A patent/JPH09509434A/en not_active Ceased
- 1994-03-14 KR KR1019950704549A patent/KR960701918A/en active IP Right Grant
- 1994-03-14 EP EP94913903A patent/EP0695317A1/en not_active Withdrawn
- 1994-03-14 AU AU65881/94A patent/AU6588194A/en not_active Abandoned
- 1994-04-06 TW TW083102974A patent/TW260699B/zh active
- 1994-09-08 US US08/303,264 patent/US5547757A/en not_active Expired - Fee Related
-
2003
- 2003-12-09 JP JP2003410941A patent/JP2004156042A/en active Pending
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