Curable coating compositions

Patent metadata

Field	Value
Publication number	US-11518904-B2
Application number	US-201916581810-A
Country	US
Kind code	B2
Filing date	Sep 25, 2019
Priority date	Sep 26, 2018
Publication date	Dec 6, 2022
Grant date	Dec 6, 2022

Abstract

Described herein are two-component curable compositions for coatings, paints, primers, topcoats, and the like. The systems herein include curable components that permit a wide latitude in additional additives used in the product formulation. In one aspect, the curable components of the compositions include a first component of polymer(s) or oligomer(s) having a beta-dicarbonyl group or dicarbonyl functionality of 1 or greater combined with a separate, second component of polymer(s) or oligomer(s) having an alkylidene malonate functionality of 1 or greater in the presence of a catalyst or initiator and other acidic compositional components.

First claim

What is claimed is:

1. A curable composition comprising:
(i) a first cure component of a polymer or oligomer having a dicarbonyl functionality of 1 or greater provided by a moiety on the polymer or oligomer having the structure of Formula (I)

wherein
X is a heteroatom linker or organic group to a polymer or oligomer backbone;
Y is —OR 1 or a —C1 to —C4 hydrocarbyl group; and
R 1 is a C1 to C20 hydrocarbyl group;

(ii) a second cure component of another polymer or oligomer having an alkylidene malonate functionality of 1 or greater provided by the structure of Formula (III)

wherein R 6 is hydrogen, a C1 to C9 alkyl group, or an aryl group; and

a catalyst or initiator;
about 5 to about 15 weight percent of an acid; and
wherein the curable composition includes additives having a pKa of about 7 or less.

2. The curable composition of claim 1 , wherein the dicarbonyl structures are selected from the moieties of Formula (Ia), Formula (Ib), or mixtures thereof:

3. The curable composition of claim 1 , wherein the first cure component is a polymer or oligomer having the structure of Formula (II):

wherein
R 3 is hydrogen or a linear, branched, or cyclic C1 to C4 hydrocarbyl group;
R 4 is a linear, branched, or cyclic C1 to C4 hydrocarbyl linking group or an ester group of the structure —C(O)OR 5 — with R 5 being a C1 to C4 linear, branched, or cyclic hydrocarbyl group.

4. The curable composition of claim 1 , wherein monomers to form the polymer or oligomer forming the first cure component are selected from the group consisting of acetoacetoxyethyl (meth)acrylate; acetoacetoxypropyl (meth)acrylate; acetoacetoxybutyl (meth)acrylate; allyl acetoacetate; 2,3 -di(acetoacetoxy)propyl methacrylate; and mixtures thereof.

5. The curable composition of claim 1 , wherein the alkylidene malonate functionality of the second cure component has the structure:

6. The curable composition of claim 1 , wherein the polymer or oligomer having the dicarbonyl functionality further includes acrylic monomer units, vinyl monomer units, polyester monomer units, polycarbonate monomer units, polyepoxyester monomer units, polyurethane monomer units, or mixtures thereof.

7. The curable composition of claim 1 , wherein the polymer or oligomer having the alkylidene malonate monomer is a condensation product of diethyl methylene malonate and 1,4-butanediol.

8. The curable composition of claim 1 , wherein the catalyst or initiator is polymeric, oligomeric, or a compound.

9. The curable composition of claim 1 , wherein the catalyst or initiator is a compound selected from the group consisting of guanidines, amidines, hydroxides, alkoxides, oxides, tertiary amines, alkali metal carbonates, alkali metal bicarbonates, alkali metal phosphates, alkali metal hydrogen phosphates, phosphines, alkali metal salts of carboxylic acids, alkali silicates, tetra methyl guanidine (TMG), 1,8-Diazabicyclo(5.4.0)undec-7-ene (DBU), 1,5-Diazabicyclo(4.3.0)non-5-ene (DBN), 1,4 diazabicyclo (2.2.2)octane (DABCO), tertiary butyl ammonium hydroxide (TBAH), sodium hydroxide, potassium hydroxide, sodium methoxide, sodium ethoxide, tri potassium phosphate, calcium oxide, triethylamine, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, potassium hydrogen phosphate (mono-basic and di-basic), triphenyl phosphine, triethyl phosphine, sodium silicate, potassium acetate, potassium acrylate, potassium octanoate, and combinations thereof.

10. The curable composition of claim 1 , wherein the catalyst or initiator has a pKa of about 12 or less.

11. The curable composition according to claim 1 , wherein the acid is added to adjust pot-life and/or cure properties.

12. The curable composition of claim 1 , wherein the acid is selected from acetic acid, propionic acid, benzoic acid, ethylhexanoic acid, or combinations thereof.

13. The curable composition of claim 1 , further comprising organic pigments, inorganic pigments, or combinations thereof.

14. The curable composition of claim 13 , wherein the organic pigments have an acidic surface treatment.

15. The curable composition of claim 1 , further comprising components having a pKa between 3 and about 6.

16. The curable composition of claim 1 , when cured, further comprising over about 200 MEK double rubs after about 24 hours of ambient cure.

17. The curable composition of claim 1 , further including inorganic pigments having an acidic surface treatment.

18. The curable composition of claim 1 , further including benzotriazole-based UV absorbers.

19. The curable composition of claim 1 , wherein the curable composition is applied to a substrate having an acidic surface.

Assignees

• Swimc Llc

Inventors

• Tye Anthony J

Classifications

• C09D165/00 Primary

  Coating compositions based on macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain (C09D107/00 - C09D157/00, C09D161/00 take precedence); Coating compositions based on derivatives of such polymers · CPC title

• C08K3/013

  Fillers, pigments or reinforcing additives · CPC title

• C09D129/12

  Homopolymers or copolymers of unsaturated ketones · CPC title

• C09D133/12 Primary

  Homopolymers or copolymers of methyl methacrylate · CPC title

• C08K5/31

  Guanidine; Derivatives thereof · CPC title