WO1994010212B1 - Aqueous aminoplast-curable film-forming compositions providing films having resistance to acid etching - Google Patents
Aqueous aminoplast-curable film-forming compositions providing films having resistance to acid etchingInfo
- Publication number
- WO1994010212B1 WO1994010212B1 PCT/US1993/010173 US9310173W WO9410212B1 WO 1994010212 B1 WO1994010212 B1 WO 1994010212B1 US 9310173 W US9310173 W US 9310173W WO 9410212 B1 WO9410212 B1 WO 9410212B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition
- groups
- pendant
- methylol
- film
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract 29
- 239000002253 acid Substances 0.000 title claims abstract 3
- 238000005530 etching Methods 0.000 title 1
- 239000000463 material Substances 0.000 claims abstract 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract 5
- 239000011248 coating agent Substances 0.000 claims abstract 3
- 238000000576 coating method Methods 0.000 claims abstract 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims abstract 2
- 239000003431 cross linking reagent Substances 0.000 claims abstract 2
- 229920000058 polyacrylate Polymers 0.000 claims 6
- ARZLUCYKIWYSHR-UHFFFAOYSA-N hydroxymethoxymethanol Chemical group OCOCO ARZLUCYKIWYSHR-UHFFFAOYSA-N 0.000 claims 4
- 125000003010 ionic group Chemical group 0.000 claims 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 4
- 125000004432 carbon atoms Chemical group C* 0.000 claims 3
- 239000007787 solid Substances 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000000129 anionic group Chemical group 0.000 claims 2
- 239000004202 carbamide Substances 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 229920005989 resin Polymers 0.000 claims 2
- 239000011347 resin Substances 0.000 claims 2
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N Melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims 1
- 229920000877 Melamine resin Polymers 0.000 claims 1
- 238000007720 emulsion polymerization reaction Methods 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 229920000728 polyester Polymers 0.000 claims 1
- 239000004814 polyurethane Substances 0.000 claims 1
- 229920002635 polyurethane Polymers 0.000 claims 1
Abstract
An aqueous aminoplast-curable film-forming composition is disclosed. The aqueous film-forming composition is a crosslinkable composition comprising (1) a material containing a plurality of carbamate and/or urea functional groups and (2) an aminoplast crosslinking agent. The aqueous composition provides a coating with improved acid etch resistance, making the compositions particularly useful as automotive clear coats.
Claims
1. An aqueous-based curable liquid film-forming composition comprising (1) 50 to 90 percent by weight based on weight of resin solids in the film-forming composition of a material containing a plurality of terminal or pendant urea or carbamate groups only of the structure:
R I
X - C - N - H
II o and/or urethane group of the structure:
where X is -N or -O and R is H and R1 is alkyl of 1 to 18 carbon atoms; and (2) 10 to 50 percent by weight based on weight of resin solids in the film-forming composition of an aminoplast crosslinking agent containing methylol and/or methylol ether groups; said film-forming composition being crosslinkable through reaction of said pendant or terminal groups with said methylol and/or methylol ether groups; said film-forming composition being further characterized as having a calculated hydroxyl value less than 50 based on solid weight of said film-forming composition, excluding any hydroxyl functionality associated with N-methylol groups so as to result in a crosslinked coating which has a substantial number of urethane and/or urea crosslinks arising from said reaction of pendant or terminal groups with said methylol and/or methylol ether groups, giving said crosslinked coating a high level of acid etch resistance.
2. The composition of claim 1 in which the material is an acrylic polymer.
3. The composition of claim 2 in which the acrylic polymer is prepared by aqueous emulsion polymerization techniques.
4. The composition of claim 2 in which the acrylic polymer is prepared in organic solvent and inverted into aqueous medium.
5. The composition of claim 4 in which the acrylic polymer contains ionic groups.
6. The composition of claim 5 in which the ionic groups are anionic groups.
7. The composition of claim 2 in which the acrylic polymer has an equivalent weight less than 5000 based on equivalents of said terminal or pendant groups.
8. The composition of claim 7 in which the acrylic polymer has an equivalent weight of from about 140 to 2500 based on equivalents of said terminal or pendant groups.
9. The composition of claim 1 in which the material is selected from the group consisting of polyesters, polyurethanes, and mixtures thereof.
10. The composition of claim 9 in which the material is prepared in organic solvent and inverted into aqueous medium.
11. The composition of claim 10 in which the material contains ionic groups.
12. The composition of claim 11 in which the ionic groups are anionic groups. - 26 -
13. The composition of claim 9 in which the material has on average at least two of said pendant or terminal groups.
14. The composition of claim 13 in which the material has an equivalent weight of from about 140 to 2500 based on equivalents of said terminal or pendant groups.
15. The composition of claim 1 in which X is -O and R1 is alkyl containing from 1 to 6 carbon atoms.
16. The composition of claim 1 in which the aminoplast is a condensate of melamine with formaldehyde and optionally an alcohol containing from 1 to 6 carbon atoms.
17. The composition of claim 15 wherein the equivalent ratio of said pendant or terminal groups to methylol or methylol ether groups is from 0.5 to 2:1 and is sufficient to form a crosslinked film.
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP93925020A EP0666876A1 (en) | 1992-10-30 | 1993-10-25 | Aqueous aminoplast-curable film-forming compositions providing films having resistance to acid etching |
AU54495/94A AU5449594A (en) | 1992-10-30 | 1993-10-25 | Aqueous aminoplast-curable film-forming compositions providing films having resistance to acid etching |
KR1019950701697A KR950704369A (en) | 1992-10-30 | 1993-10-25 | AQUEOUS AMINOPLAST-CURABLE FILM-FORMING COMPOSITIONS PROVIDING FILMS HAVING RESISTANCE TO ACID ETCHING |
BR9307431-0A BR9307431A (en) | 1992-10-30 | 1993-10-25 | Curable film-forming water-based composition |
JP6511210A JPH07508793A (en) | 1992-10-30 | 1993-10-25 | Aminoplast-curable aqueous film-forming compositions that provide coatings with acid etch resistance |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/968,807 US6103816A (en) | 1992-10-30 | 1992-10-30 | Aqueous aminoplast curable film-forming compositions providing films having resistance to acid etching |
US07/968,807 | 1992-10-30 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO1994010212A1 WO1994010212A1 (en) | 1994-05-11 |
WO1994010212B1 true WO1994010212B1 (en) | 1994-07-21 |
Family
ID=25514804
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1993/010173 WO1994010212A1 (en) | 1992-10-30 | 1993-10-25 | Aqueous aminoplast-curable film-forming compositions providing films having resistance to acid etching |
Country Status (9)
Country | Link |
---|---|
US (1) | US6103816A (en) |
EP (1) | EP0666876A1 (en) |
JP (1) | JPH07508793A (en) |
KR (1) | KR950704369A (en) |
AU (1) | AU5449594A (en) |
BR (1) | BR9307431A (en) |
CA (1) | CA2145849A1 (en) |
MX (1) | MX9306713A (en) |
WO (1) | WO1994010212A1 (en) |
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-
1992
- 1992-10-30 US US07/968,807 patent/US6103816A/en not_active Expired - Fee Related
-
1993
- 1993-10-25 CA CA002145849A patent/CA2145849A1/en not_active Abandoned
- 1993-10-25 EP EP93925020A patent/EP0666876A1/en not_active Withdrawn
- 1993-10-25 BR BR9307431-0A patent/BR9307431A/en not_active Application Discontinuation
- 1993-10-25 AU AU54495/94A patent/AU5449594A/en not_active Abandoned
- 1993-10-25 WO PCT/US1993/010173 patent/WO1994010212A1/en not_active Application Discontinuation
- 1993-10-25 JP JP6511210A patent/JPH07508793A/en active Pending
- 1993-10-25 KR KR1019950701697A patent/KR950704369A/en not_active Application Discontinuation
- 1993-10-28 MX MX9306713A patent/MX9306713A/en unknown
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