Aqueous coating compositions containing acetoacetyl-functional polymers, coatings, and methods

Patent metadata

Field	Value
Publication number	US-9803045-B2
Application number	US-30007005-A
Country	US
Kind code	B2
Filing date	Dec 14, 2005
Priority date	Dec 17, 2004
Publication date	Oct 31, 2017
Grant date	Oct 31, 2017

Abstract

Aqueous coating compositions that include polymers having one or more of the following acetoacetyl-functional groups:

wherein R 1 is a C1 to C22 alkylene group and R 2 is a C1 to C22 alkyl group.

First claim

What is claimed is:

1. A coating composition consisting of:
water;
a latex polymer stabilized with an alkali-soluble polymer;
wherein the alkali-soluble polymer is derived from greater than 10% by weight of one or more polymerizable acid monomers;
wherein the latex polymer comprises one or more acetoacetyl-functional groups of the formula:

wherein R 1 is a C1 to C22 alkylene group and R 2 is a C1 to C22 alkyl group;

trimethylolpropane ethoxylate tri(meth)acrylate;
and
a hydrogen abstraction-type photoinitiator; wherein the hydrogen abstraction-type photoinitiator is selected to cure the acetoacetyl-functional latex polymer via a free radical UV cure mechanism through hydrogen abstraction of the —C(O)—CH 2 —C(O)— hydrogens;
wherein the coating composition does not include a multifunctional amine crosslinker.

2. The coating composition of claim 1 comprising no more than 10 wt-% volatile organic compounds, based on the total weight of the composition.

3. The coating composition of claim 1 wherein the acetoacetyl-functional polymer comprises an acetoacetyl-functional polyurethane, epoxy, polyamide, chlorinated polyolefin, acrylic, oil-modified polymer, polyester, or mixtures or copolymers thereof.

4. The coating composition of claim 1 wherein the acetoacetyl-functional polymer comprises an acetoacetyl-functional latex polymer prepared from ethylenically unsaturated monomers.

5. The coating composition of claim 4 wherein the latex polymer comprises particles having an average particle size of less than 75 nm.

6. The coating composition of claim 1 wherein the acetoacetyl-functional group is incorporated into the latex polymer using 2-(acetoacetoxy) ethyl methacrylate, t-butyl acetoacetate, diketene, or combinations thereof.

7. The coating composition of claim 1 wherein the hydrogen abstraction-type photoinitiator is benzophenone or 4-methylbenzophenone.

8. The coating composition of claim 7 which is at least partially curable by ultraviolet or visible light.

9. A method of coating a substrate, the method comprising applying the coating composition of claim 1 to a substrate and allowing the coating composition to harden.

10. A coating on a substrate preparable by the method of claim 9 .

11. The coating composition of claim 1 wherein trimethylolpropane ethoxylate tri(meth)acrylate is present in an amount of at least 5 wt-%, based on the combined weight of trimethylolpropane ethoxylate tri(meth)acrylate and the acetoacetyl-functional polymer.

12. The coating composition of claim 11 wherein the acetoacetyl-functional polymer is present in an amount of at least 30 wt-% and no more than 95 wt-%, and trimethylolpropane ethoxylate tri(meth)acrylate is present in an amount of at least 5 wt-% and no more than 70 wt-%, based on the combined weight of trimethylolpropane ethoxylate tri(meth)acrylate and the acetoacetyl-functional polymer.

13. The coating composition of claim 11 wherein trimethylolpropane ethoxylate tri(meth)acrylate is present in an amount of at least 7.5 wt-%, based on the combined weight of trimethylolpropane ethoxylate tri(meth)acrylate and the acetoacetyl-functional polymer.

14. The coating composition of claim 11 wherein trimethylolpropane ethoxylate tri(meth)acrylate is present in an amount of at least 10 wt-%, based on the combined weight of trimethylolpropane ethoxylate tri(meth)acrylate and the acetoacetyl-functional polymer.

15. The coating composition of claim 1 wherein the latex polymer is distinct from the alkali-soluble polymer.

16. A method of coating a substrate surface, the method comprising:
providing a coating composition consisting of:
water;
a latex polymer stabilized with an alkali-soluble polymer;
wherein the alkali-soluble polymer is derived from greater than 10% by weight of one or more polymerizable acid monomers;
wherein the latex polymer comprises one or more acetoacetyl-functional groups of the formula:

wherein R 1 is a C1 to C22 alkylene group and R 2 is a C1 to C22 alkyl group;

an ethylenically unsaturated compound distinct from the polymer comprising acetoacetyl functionality; wherein the ethylenically unsaturated compound is a monomer, oligomer, or mixture thereof comprising a multifunctional (meth)acrylate-functional monomer selected from the group consisting of isobornyl (meth)acrylate, isodecyl (meth)acrylate, phenoxyethyl (meth)acrylate, trimethylolpropane tri(meth)acrylate, trimethylolpropane ethoxylate tri(meth)acrylate, tripropylene glycol di(meth)acrylate, hexanediol di(meth)acrylate, tetrahydrofurfuryl (meth)acrylate, beta-carboxyethyl (meth)acrylate, bisphenol A ethoxylate di(meth)acrylate, ethoxylated neopentyl glycol di(meth)acrylate, propoxylated neopentyl glycol di(meth)acrylate, di-(trimethylolpropane tetra (meth)acrylate), pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, and mixtures thereof;
and
optionally an initiator;

applying the coating composition to a substrate surface; and
at least partially curing the coating composition.

17. The method of claim 16 wherein the coating composition comprises no more than 10 wt-% volatile organic compounds, based on the total weight of the composition.

18. The method of claim 16 wherein the acetoacetyl-functional polymer comprises an acetoacetyl-functional polyurethane, epoxy, polyamide, chlorinated polyolefin, acrylic, oil-modified polymer, polyester, or mixtures or copolymers thereof.

19. The method of claim 16 wherein the latex polymer comprises particles comprising the acetoacetyl-functional polymer, the alkali-soluble polymer, and the ethylenically unsaturated monomer, oligomer, or mixture thereof.

20. The method of claim 19 wherein the latex polymer comprises particles having an average particle size of less than 75 nm.

21. The method of claim 16 wherein the acetoacetyl-functional polymer is present in an amount of at least 30 wt-% and no more than 95 wt-%, based on the combined weight of ethylenically unsaturated monomer, oligomer, or mixture thereof and the acetoacetyl-functional polymer, and wherein the ethylenically unsaturated monomer, oligomer, or mixture thereof is present in an amount of at least 5 wt-% and no more than 70 wt-%, based on the combined weight of the ethylenically unsaturated monomer, oligomer, or mixture thereof and the acetoacetyl-functional polymer.

22. The method of claim 16 wherein the acetoacetyl functionality is incorporated into the latex polymer using 2-(acetoacetoxy) ethylmethacrylate, t-butyl acetoacetate, or diketene.

23. The method of claim 16 wherein the initiator is present in the latex polymer and comprises a photoinitiator, wherein the photoinitiator comprises benzophenone, 4-methylbenzophenone, benzoyl benzoate, phenylacetophenones, 2,2-dimethoxy-2-phenylacetophenone, alpha,alpha-diethoxyacetophenone, hydroxycyclo-hexylphenylketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, bis-(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentyl phosphine oxide, 2,4,6-trimethylbenzoyl-diphenylphosphine oxide, or combinations thereof.

24. The method of claim 16 wherein the initiator is present in the la

Assignees

• Killilea T Howard
• Valspar Sourcing Inc

Inventors

• Killilea T Howard

Classifications

• C09D133/14

  of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen · CPC title

• C08G18/6659

  with compounds of group C08G18/34 · CPC title

• C08G18/0823 Primary

  containing carboxylate salt groups or groups forming them · CPC title

• C09D175/16

  having terminal carbon-to-carbon unsaturated bonds · CPC title

• C08G18/672

  Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen · CPC title