Catalytic compositions and thiolene-based compositions with extended pot life

Patent metadata

Field	Value
Publication number	US-11628431-B2
Application number	US-202117177885-A
Country	US
Kind code	B2
Filing date	Feb 17, 2021
Priority date	Dec 20, 2018
Publication date	Apr 18, 2023
Grant date	Apr 18, 2023

Abstract

The present invention is directed to curable compositions comprising: (a) a polyene; (b) a polythiol, present in an amount greater than 10 percent by weight based on the total weight of components (a) and (b) in the curable composition; and (c) a catalytic component consisting essentially of: (i) a metal compound; and (ii) a compound different from (i) that catalyzes an addition reaction between an ethylenically unsaturated compound and a thiol. The catalytic composition is essentially free of vanadium compounds. In the curable composition, either (1) both components (i) and (ii) of the catalytic composition (c) are added as a single package to (a) and/or (b); or (2) component (i) and/or (ii) of the catalytic composition (c) is added in separate packages to (a) and/or (b) of the curable composition. The present invention is further drawn to coated articles and methods of extending pot life of a curable composition.

First claim

What is claimed is:

1. A curable composition comprising:
(a) a polyene;
(b) a polythiol, present in an amount greater than 10 percent by weight based on the total weight of components (a) and (b) in the curable composition;
(c) a catalytic component consisting essentially of:
(i) a metal compound; and
(ii) a compound different from (i) that catalyzes an addition reaction between an ethylenically unsaturated compound and a thiol, wherein said catalytic composition is essentially free of vanadium compounds; and

(d) a pigment;

wherein either (1) both components (i) and (ii) of the catalytic composition (c) are added as a single package to (a) and/or (b), or (2) component (i) and/or (ii) of the catalytic composition (c) is added in separate packages to (a) and/or (b) of the curable composition.

2. The curable composition of claim 1 wherein both components (i) and (ii) of the catalytic composition (c) are added as a single package to (a) and/or (b).

3. The curable composition of claim 1 wherein component (i) and/or (ii) of the catalytic composition (c) is added in separate packages to (a) and/or (b) of the curable composition.

4. The curable composition of claim 1 wherein the metal compound (i) comprises an iron compound.

5. The curable composition of claim 4 wherein the metal compound (i) is present in the curable composition in amounts of 1 to 1000 ppm metal, based on the total weight of components (a) and (b) in the curable composition.

6. The curable composition of claim 1 , wherein the compound (ii) is selected from the group consisting of oxazolidines, triethylamine, dimethylcyclohexylamine, dimethyloctylamine, dimethyldodecylamine, dimethylamino ethanol, tetramethyl guanidine, diaza-bicyclo-octane, diaza-bicyclo-undecene, diaza-bicyclo-nonene, n-methyl-triaza-bicyclodecene, trioctyl phosphine, triphenyl phosphine, and mixtures thereof.

7. The curable composition of claim 6 wherein the compound (ii) is present in the curable composition in amounts of 0.001 to 10 percent by weight, based on the total weight of components (a) and (b) in the curable composition.

8. The curable composition of claim 1 wherein the polyene has the structural formula
A-(X) m

where A is an organic moiety; X is an olefinically unsaturated moiety and m is at least 2.

9. The curable composition of claim 8 wherein X is selected from
—C(O)CR═CH 2 , —CH 2 —CHR═CH 2 and mixtures thereof, where R is hydrogen or methyl.

10. The curable composition of claim 8 wherein A contains groups selected from ester and urethane groups.

11. The curable composition of claim 8 wherein A is derived from a polyisocyanate.

12. The curable composition of claim 8 wherein A-(X) m comprises a polyurethane (meth)acrylate and/or a polyester (meth)acrylate.

13. The curable composition of claim 1 wherein the polythiol comprises a reaction product of a thiol-functional organic acid and a polyol.

14. The curable composition of claim 1 wherein the equivalent ratio of thiol functional groups in the polythiol (b) to ethylenically unsaturated groups in the polyene (a) is from 0.1 to 10:1.

15. A coated article comprising
(a) a substrate comprising metal, glass, wood, and/or a polymer; and
(b) a curable composition applied to a surface of the substrate as a coating layer, wherein the curable composition comprises the curable composition of claim 1 .

16. The coated article of claim 15 , wherein the coating layer comprises a sealant.

17. The coated article of claim 15 , wherein the coating layer comprises a primer coat or topcoat.

18. A method of extending pot life of a curable composition, comprising
(1) preparing a catalytic composition consisting essentially of:
(i) a metal compound; and
(ii) a compound different from (i) that catalyzes an addition reaction between an ethylenically unsaturated compound and a thiol, wherein said catalytic composition is essentially free of vanadium compounds; and

(2) adding the catalytic composition to the curable composition, wherein the curable composition comprises:
(a) a polyene;
(b) a polythiol, present in an amount greater than 10 percent by weight based on the total weight of components (a) and (b) in the curable composition; and
(c) a pigment.

19. The method of claim 18 , wherein either: (1) both components (i) and (ii) of the catalytic composition are added as a single package to (a) and/or (b); or (2) component (i) and/or (ii) of the catalytic composition is added in separate packages to (a) and/or (b) of the curable composition.

Assignees

• Ppg Ind Ohio Inc

Inventors

• Moravek Scott J
• Schwartzmiller Davina J
• Gianellini Stefano
• Bertoli Matteo
• Ballarino Maurizio
• Bowles Steven
• Powell Adam Bradley

Classifications

• B01J2231/4294

  using S nucleophiles, e.g. thiols · CPC title

• B01J2531/842

  Iron · CPC title

• B01J2540/40

  Non-coordinating groups comprising nitrogen · CPC title

• C08L33/10

  Homopolymers or copolymers of methacrylic acid esters · CPC title

• C09D175/14

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