Curable film-forming compositions containing hydroxyl functional, branched acrylic polymers and multilayer composite coatings

Patent metadata

Field	Value
Publication number	US-10767073-B2
Application number	US-201615296514-A
Country	US
Kind code	B2
Filing date	Oct 18, 2016
Priority date	Oct 18, 2016
Publication date	Sep 8, 2020
Grant date	Sep 8, 2020

Abstract

A curable film-forming composition is provided, comprising:
(a) a polymeric polyester binder comprising a plurality of carbamate groups; (b) a curing agent reactive with the carbamate functional groups of (a); and (c) a reaction product of: (1) a hydroxyl functional polymer comprising the reaction product of:
(i) a monomer comprising at least two ethylenically unsaturated double bonds; (ii) a monomer comprising a carbon atom that is bonded to four moieties wherein one of the moieties is a hydrogen atom and the remainder of the moieties comprises an alkyl group, wherein at least one of the alkyl group-containing moieties comprises an ethylenically unsaturated double bond; and (iii) at least one monomer that is polymerizable with (i) and (ii); and
(2) a lactone or lactam. Also provided are a multi-component composite coating composition that includes the curable film-forming composition described above and methods for forming a composite coating on a substrate.

First claim

We claim:

1. A curable film-forming composition comprising:
(a) a polymeric binder comprising repeating ester groups in the polymer backbone and further comprising a plurality of carbamate groups of the structure:

(b) a curing agent comprising functional groups that are reactive with the carbamate functional groups of (a); and
(c) a reaction product of:
(1) a hydroxyl functional (meth)acrylic polymer comprising the reaction product of:
(i) at least 1 percent by weight of a (meth)acrylic monomer comprising at least two ethylenically unsaturated double bonds;
(ii) at least 10 percent by weight of a (meth)acrylic monomer comprising a carbon atom that is bonded to four moieties wherein one of said moieties is a hydrogen atom and the remainder of said moieties comprises an alkyl group, wherein at least one of the alkyl group-containing moieties comprises an ethylenically unsaturated double bond; and
(iii) at least one ethylenically unsaturated monomer that is polymerizable with (i) and (ii); wherein each monomer (i), (ii), and (iii) is different and wherein the monomer (i), (ii) and/or (iii) contains a hydroxyl functional group; and

(2) a lactone or lactam; wherein the reaction product (c) has a weight average molecular weight of at least 500 to 8504.

2. The curable film-forming composition according to claim 1 , wherein (i) comprises a di(meth)acrylate monomer.

3. The curable film-forming composition according to claim 1 , wherein (ii) comprises 2-ethyl hexyl(meth)acrylate, 2-butyl hexyl(meth)acrylate, 2-methyl hexyl(meth)acrylate, isobornyl acrylate, isobornyl methacrylate, or combinations thereof.

4. The curable film-forming composition according to claim 1 , wherein (iii) comprises a hydroxy functional (meth)acrylate.

5. The curable film-forming composition according to claim 4 , wherein (iii) further comprises an ethylenically unsaturated monomer that does not contain any additional, different reactive functional groups.

6. The curable film-forming composition of claim 1 , wherein the polymeric binder (a) comprises a polyester which is a reaction product of (i) an alkyl carbamate; (ii) an organic polycarboxylic acid or anhydride and (iii) a mixture of at least one diol and at least one triol.

7. The curable film-forming composition of claim 6 , wherein the alkyl carbamate comprises methyl carbamate.

8. A multi-component composite coating composition comprising a first film-forming composition applied to a substrate to form a colored base coat, and a second, transparent film-forming composition applied on top of the base coat to form a clear top coat, wherein the transparent film-forming composition comprises a curable film-forming composition comprising:
(a) a polymeric binder comprising repeating ester groups in the polymer backbone and further comprising a plurality of carbamate groups of the structure:

(b) a curing agent comprising functional groups that are reactive with the carbamate functional groups of (a); and
(c) a reaction product of:
(1) a hydroxyl functional (meth)acrylic polymer comprising the reaction product of:
(i) at least 1 percent by weight of a (meth)acrylic monomer comprising at least two ethylenically unsaturated double bonds;
(ii) at least 10 percent by weight of a (meth)acrylic monomer comprising a carbon atom that is bonded to four moieties wherein one of said moieties is a hydrogen atom and the remainder of said moieties comprises an alkyl group, wherein at least one of the alkyl group-containing moieties comprises an ethylenically unsaturated double bond; and
(iii) at least one ethylenically unsaturated monomer that is polymerizable with (i) and (ii); wherein each monomer (i), (ii), and (iii) is different and wherein the monomer (i), (ii) and/or (iii) contains a hydroxyl functional group; and

(2) a lactone or lactam; wherein the reaction product (c) has a weight average molecular weight of at least 500 to 8504.

9. The multi-component composite coating composition according to claim 8 , wherein (i) comprises a di(meth)acrylate monomer.

10. The multi-component composite coating composition according to claim 8 , wherein (ii) comprises 2-ethyl hexyl(meth)acrylate, 2-butyl hexyl(meth)acrylate, 2-methyl hexyl(meth)acrylate, isobornyl acrylate, isobornyl methacrylate, or combinations thereof.

11. The multi-component composite coating composition according to claim 8 , wherein (iii) comprises a hydroxy functional (meth)acrylate.

12. The multi-component composite coating composition according to claim 11 , wherein (iii) further comprises an ethylenically unsaturated monomer that does not contain any additional, different reactive functional groups.

13. The multi-component composite coating composition of claim 8 , wherein the polymeric binder (a) comprises a polyester which is a reaction product of (i) an alkyl carbamate; (ii) an organic polycarboxylic acid or anhydride and (iii) a mixture of at least one diol and at least one triol.

14. The multi-component composite coating composition of claim 13 , wherein the alkyl carbamate comprises methyl carbamate.

15. A method for forming a composite coating on a substrate comprising:
(A) applying a first film-forming composition to at least a portion of a surface of the substrate to form a colored base coat;
(B) applying a second, transparent film-forming composition to at least a portion of the base coat formed in step (A) prior to curing the first film-forming composition, to form a clear top coat thereon, wherein the transparent film-forming composition comprises a curable film-forming composition comprising:
(a) a polymeric binder comprising repeating ester groups in the polymer backbone and further comprising a plurality of carbamate groups of the structure:

(b) a curing agent comprising functional groups that are reactive with the carbamate functional groups of (a); and
(c) a reaction product of:
(1) a hydroxyl functional (meth)acrylic polymer comprising the reaction product of:
(i) at least 1 percent by weight of a (meth)acrylic monomer comprising at least two ethylenically unsaturated double bonds;
(ii) at least 10 percent by weight of a (meth)acrylic monomer comprising a carbon atom that is bonded to four moieties wherein one of said moieties is a hydrogen atom and the remainder of said moieties comprises an alkyl group, wherein at least one of the alkyl group-containing moieties comprises an ethylenically unsaturated double bond; and
(iii) at least one ethylenically unsaturated monomer that is polymerizable with (i) and (ii); wherein each monomer (i), (ii), and (iii) is different and wherein the monomer (i), (ii) and/or (iii) contains a hydroxyl functional group; and

(2) a lactone or lactam; wherein the reaction product (c) has a weight average molecular weight of at least 500 to 8504; and
(C) holding the substrate at a temperature and for a time sufficient to cure the composite coating after all coating layers have been applied to the substrate.

Assignees

• Ppg Ind Ohio Inc

Inventors

• Swarup Shanti
• Lewis Jason Ryan

Classifications

• C08F220/1808

  C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate · CPC title

• C08F220/1804 Primary

  C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate · CPC title

• C09D167/00 Primary

  Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain (based on polyester-amides C09D177/12; based on polyester-imides C09D179/08); Coating compositions based on derivatives of such polymers · CPC title

• C08L2205/05

  containing polymer components which can react with one another · CPC title

• C08G63/685

  containing nitrogen · CPC title