Free radical-curable coating and sealant compositions with improved surface cure properties

Patent metadata

Field	Value
Publication number	US-10995219-B2
Application number	US-201716085011-A
Country	US
Kind code	B2
Filing date	Mar 6, 2017
Priority date	Mar 15, 2016
Publication date	May 4, 2021
Grant date	May 4, 2021

Abstract

Inhibition by oxygen of the peroxide-initiated cure of a composition based on (meth)acrylates or other compounds containing free radical-polymerizable functional groups is mitigated by inclusion of one or more polythiols in the composition. Such compositions may be formulated as multi-part systems, which are useful for the preparation of coatings and sealants.

First claim

The invention claimed is:

1. A multi-part system either a) or b) comprising, as separately packaged components, either:
a) a Part A comprising at least one compound having two or more free radical-polymerizable functional groups and at least one polythiol compound comprising two or more thiol groups and a Part B comprising at least one free radical initiator; or
b) a Part A comprising at least one compound having two or more free radical-polymerizable functional groups, a Part B comprising at least one polythiol comprising two or more thiol groups and a Part C comprising at least one free radical initiator,
wherein the free radical-polymerizable functional groups are selected from the group consisting of allyl groups, (meth)acrylate groups and combinations thereof.

2. The multi-part system of claim 1 , wherein the free radical-polymerizable functional groups are ethylenically unsaturated functional groups.

3. The multi-part system of claim 1 , wherein Part A comprises at least one hydroxyl-functionalized (meth)acrylate.

4. The multi-part system of claim 1 , wherein Part A comprises at least one hydroxyl-functional epoxy (meth)acrylate.

5. The multi-part system of claim 1 , wherein Part A comprises at least one urethane (meth)acrylate.

6. The multi-part system of claim 1 , wherein the at least one compound having two or more free radical-polymerizable functional groups comprises at least one crosslinking monomer which is a dual functional monomer comprising at least three free radical-polymerizable functional groups selected from the group consisting of allyl groups, (meth)acrylate groups and combinations thereof, including at least one allyl group and at least one (meth)acrylate group.

7. The multi-part system of claim 1 , wherein Part A comprises at least one epoxy (meth)acrylate and at least one crosslinking monomer which is a dual functional monomer comprising at least three free radical-polymerizable functional groups selected from the group consisting of allyl groups, (meth)acrylate groups and combinations thereof, including at least one allyl group and at least one (meth)acrylate group.

8. The multi-part system of claim 1 , wherein Part A additionally comprises at least one compound having a single free radical polymerizable group.

9. The multi-part system of claim 1 , wherein Part A comprises at least one compound having at least one (meth)acrylate functional group, at least one hydroxyl functional group and at least one epoxy group per molecule.

10. The multi-part system of claim 1 , wherein the at least one polythiol compound includes at least one polythiol compound having a molecular weight of from 350 Daltons to 2000 Daltons.

11. The multi-part system of claim 1 , wherein the at least one polythiol compound includes at least one polythiol compound having a molecular weight of from 400 Daltons to 1000 Daltons.

12. The multi-part system of claim 1 , wherein the at least one polythiol compound includes at least one polythiol compound comprising three or more thiol groups.

13. The multi-part system of claim 1 , wherein the at least one polythiol compound includes at least one polythiol compound comprising three to six thiol groups.

14. The multi-part system of claim 1 , wherein the at least one polythiol compound includes at least one polythiol compound comprising two or more thiol-functionalized carboxylate groups having a structure O—C(═O)—(CH 2 ) n —SH, where n is 1 or 2.

15. The multi-part system of claim 1 , wherein the at least one polythiol compound includes at least one polythiol compound obtained by esterifying a polyalcohol with a thiol-functionalized carboxylic acid.

16. The multi-part system of claim 1 , wherein the at least one polythiol compound includes at least one polythiol compound selected from the group consisting of pentaerythritol tetra(3-mercaptopropionate), trimethylolpropane tri(3-mercaptopropionate), pentaerythritol tetra(2-mercaptoacetate) and trimethylolpropane tri(2-mercaptoacetate).

17. The multi-part system of claim 1 , wherein the at least one polythiol compound includes at least one polythiol compound having a thiol equivalent weight of from 80 Daltons to 450 Daltons.

18. The multi-part system of claim 1 , comprising from 0.01 to 15 percent by weight of polythiol compound based on the total weight of said multi-part system, either a) with respect to Part A+Part B or b) with respect to Part A+Part B+Part C.

19. The multi-part system of claim 1 , comprising from 0.1 to 5 percent by weight of polythiol compound based on the total weight of said multi-part system, either a) with respect to Part A+Part B or b) with respect to Part A+Part B+Part C.

20. The multi-part system of claim 1 , wherein Part A further comprises at least one promoter.

21. The multi-part system of claim 20 , wherein the at least one promoter comprises one or more transition metals.

22. The multi-part system of claim 1 , wherein the at least one free radical initiator includes at least one peroxide.

23. The multi-part system of claim 1 , wherein Part A additionally comprises at least one free radical stabilizer.

24. The multi-part system of claim 1 , wherein Part A additionally comprises at least one wax.

25. The multi-part system of claim 1 , comprising not more than 5 weight % in total, based on the total weight of said multi-part system, either a) with respect to Part A+Part B or b) with respect to Part A+Part B+Part C of compounds having a boiling point of less than 250° C. at 760 mm Hg.

26. A method of forming a coating or sealant on a surface of a substrate, comprising combining either Part A and Part B according to multi-part system a) as defined in claim 1 or combining Part A, Part B and Part C according to multi-part system b) as defined in claim 1 , to form a coating or sealant composition, applying the coating or sealant composition to the surface of the substrate and curing the coating or sealant composition.

27. The method of claim 26 , wherein the curing of the coating or sealant composition is carried out in the presence of oxygen and the cured coating or sealant composition has a thickness as low as 0.003 inches (76μ).

28. A method of forming a coating or sealant on a substrate comprising combining Part A and Part B of a) of claim 1 or combining Part A, Part B, and Part C of b) of claim 1 to form a mixture and applying the mixture to the substrate.

29. The method according to claim 28 , wherein the coating or sealant is used for concrete or concrete repair or for metals or in gels coats for fiber composites.

30. The method according to claim 28 , wherein the coating or sealant is used in construction.

Assignees

• Arkema France

Inventors

• Bailey Michael A
• Wlodyga Ronald R

Classifications

• C08F222/10 Primary

  Esters · CPC title

• C09D4/06 Primary

  {Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond} in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00 · CPC title

• C08G75/00

  Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule · CPC title

• C09D133/14

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

• C09J4/00

  Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16} · CPC title