Ambient cure weatherable coatings

Patent metadata

Field	Value
Publication number	US-9567480-B2
Application number	US-201314423503-A
Country	US
Kind code	B2
Filing date	Oct 23, 2013
Priority date	Oct 24, 2012
Publication date	Feb 14, 2017
Grant date	Feb 14, 2017

Abstract

An adduct including a reaction product of (a) at least a first cycloaliphatic amine compound; (b) at least a second cycloaliphatic amine compound; and (c) at least one cycloaliphatic epoxy resin compound; a curable epoxy resin coating composition including (i) the above adduct; and (ii) at least one thermosetting epoxy resin compound; said curable composition being curable at ambient temperature; and a cured weatherable coating prepared from the above curable composition.

First claim

The invention claimed is:

1. An adduct comprising a reaction product of
(a) at least a first cycloaliphatic amine compound;
(b) at least a second cycloaliphatic amine compound; and
(c) at least one cycloaliphatic epoxy resin compound;
wherein the first and second cycloaliphatic amine compounds comprise bis(2-(piperazin-1-yl)ethyl amine; aminoethyl piperazine; isophorone diamine; bis-am inomethylcyclohexane; bis(aminocyclohexyl)methane; or mixtures thereof; provided that the first and second cycloaliphatic amine compounds are not the same compound.

2. The adduct of claim 1 , wherein the at least one cycloaliphatic epoxy resin compound comprises cyclohexanedimethanol epoxy resin; hydrogenated bisphenol A epoxy resin; or mixtures thereof.

3. The adduct of claim 1 , wherein the at least one cycloaliphatic epoxy resin compound comprises 1,4-cyclohexanedimethanol epoxy resin.

4. The adduct of claim 1 , wherein the at least one cycloaliphatic epoxy resin compound comprises a mixture of 1,3-cyclohexanedimethanol epoxy resin and 1,4-cyclohexanedimethanol epoxy resin.

5. The adduct of claim 1 , wherein the first and second cycloaliphatic amine compounds independently have between 2 and 6 amine nitrogen atoms per molecule.

6. The adduct of claim 1 , wherein the first cycloaliphatic amine compound comprises isophorone diamine.

7. The adduct of claim 1 , wherein the second cycloaliphatic amine compound comprises bis(2-(piperazin-1-yl)ethyl amine, bis(aminocyclohexyl)methane, bis-aminomethylcyclohexane, or mixtures thereof.

8. The adduct of claim 1 , wherein the molar ratio of the sum of active hydrogen (N—H) of the first and second cycloaliphatic amine compound to the epoxy functionality of the at least one epoxy resin compound is from about 2 to about 20.

9. A process for preparing a curable composition comprising admixing
(A) the adduct of claim 1 ; wherein the at least one cycloaliphatic epoxy resin compound comprises 1,4-cyclohexanedimethanol epoxy resin; hydrogenated bisphenol A epoxy resin; or mixtures thereof; and (B) at least one thermosetting epoxy resin compound; said curable composition being curable at ambient temperature.

10. The process of claim 9 , wherein (C) at least one accelerator compound is admixed with compounds (A) and (B).

11. An adduct comprising a blend of
(I) at least a first adduct comprising:
(a) at least a first cycloaliphatic amine compound; and
(b) at least one cycloaliphatic epoxy resin compound; and
(II) at least a second adduct comprising:
(a) at least a second cycloaliphatic amine compound; and
(b) at least one cycloaliphatic epoxy resin compound;
wherein the first and second cycloaliphatic amine compounds comprise bis(2-(piperazin-1-yl)ethyl amine; am inoethyl piperazine; isophorone diamine; bis-aminomethylcyclohexane; bis(aminocyclohexyl)methane; or mixtures thereof; provided that the first and second cycloaliphatic amine compounds are not the same compound.

12. A process for preparing a curable composition comprising admixing
(A) the adduct of claim 11 ; wherein the at least one cycloaliphatic epoxy resin compound comprises 1,4-cyclohexanedimethanol epoxy resin; hydrogenated bisphenol A epoxy resin; or mixtures thereof; and (B) at least one thermosetting epoxy resin compound; said curable composition being curable at ambient temperature.

13. A process for preparing an adduct comprising reacting (a) at least a first cycloaliphatic amine compound; (b) at least a second cycloaliphatic amine compound; and (c) at least one cycloaliphatic epoxy resin compound
wherein the first and second cycloaliphatic amine compounds comprise bis(2-(piperazin-1-yl)ethyl amine; aminoethyl piperazine; isophorone diamine; bis-am inomethylcyclohexane; bis(aminocyclohexyl)methane; or mixtures thereof; provided that the first and second cycloaliphatic amine compounds are not the same compound.

14. A process for preparing an adduct comprising blending:
(I) at least a first adduct comprising the reaction product of:
(a) at least a first cycloaliphatic amine compound; and
(b) at least one cycloaliphatic epoxy resin compound; and
(II) at least a second adduct comprising the reaction product of:
(a) at least a second cycloaliphatic amine compound; and
(b) at least one cycloaliphatic epoxy resin compound
wherein the first and second cycloaliphatic amine compounds comprise bis(2-(piperazin-1-yl)ethyl amine; am inoethyl piperazine; isophorone diamine; bis-am inomethylcyclohexane; bis(aminocyclohexyl)methane; or mixtures thereof; provided that the first and second cycloaliphatic amine compounds are not the same compound.

15. A curable epoxy resin composition comprising
(i) an adduct comprising a reaction product of
(a) at least a first cycloaliphatic amine compound;
(b) at least a second cycloaliphatic amine compound; and
(c) at least one cycloaliphatic epoxy resin compound; and
(ii) at least one thermosetting epoxy resin compound
wherein the first and second cycloaliphatic amine compounds comprise bis(2-(piperazin-1-yl)ethyl amine; am inoethyl piperazine; isophorone diamine; bis-am inomethylcyclohexane; bis(aminocyclohexyl)methane; or mixtures thereof; provided that the first and second cycloaliphatic amine compounds are not the same compound.

16. The curable epoxy resin composition of claim 15 , wherein the at least one cycloaliphatic epoxy resin compound or comprises cyclohexanedimethanol epoxy resin; hydrogenated bisphenol A epoxy resin; or mixtures thereof.

17. The curable epoxy resin composition of claim 15 , wherein the molar ratio of active hydrogen (N-H) in the at least one adduct to the epoxy functionality in the at least one thermosetting epoxy resin compound is from about 0.5 to about 1.5.

18. The curable epoxy resin composition of claim 15 , wherein either the first or second cycloaliphatic amine compound comprises bis(2-(piperazin-l-yl)ethyl amine.

19. The curable epoxy resin composition of claim 15 , wherein the at least one thermosetting epoxy resin compound comprises 1,4-cyclohexanedimethanol epoxy resin.

20. The curable epoxy resin composition of claim 15 , including at least one of a cure catalyst; a second epoxide compound separate and different from the at least one thermosetting epoxy resin compound, a filler, a reactive diluent, a flexibilizing agent, a processing aide, a toughening agent, or a mixture thereof.

21. A process for preparing thermoset comprising:
(I) providing a curable composition of:
(i) an adduct of (a) at least one cycloaliphatic amine compound, and (b) at least one epoxy resin compound; wherein the at least one epoxy resin compound comprises 1,4-cyclohexanedimethanol epoxy resin;
hydrogenated bisphenol A epoxy resin; or mixtures thereof; and (ii) at least one thermosetting epoxy resin compound; said curable composition being curable at ambient temperature; and
(II) curing the curable composition of step (I);
wherein the at least one cycloaliphatic amine compound comprises bis(2-(piperazin-1-yl)ethyl amine; aminoethvl piperazine; isophorone diamine; bis-aminomethylcyclohexane; bis(aminocyclohexyl)methane; or mixtures thereof.

22. The process of claim 21 , wherein (iii) at least one accelerator compound is admixed with compounds (i) and (ii) in step (I).

23. A cured thermoset article prepared by the process of claim 21 .

24. The cured thermoset article of claim 23 comprising a weatherable coating.

Assignees

• Blue Cube Ip Llc

Inventors

• Vogel Erin B
• Drumright Ray E
• Machelski Susan
• Ladewski Rebecca L

Classifications

• C09D163/00 Primary

  Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins · CPC title

• C08G59/1477

  containing nitrogen · CPC title

• C08G59/24

  carbocyclic · CPC title

• C08G59/5006

  aliphatic · CPC title

• C08G59/5026

  cycloaliphatic · CPC title