Polycarbamide resins for metal coating applications

Patent metadata

Field	Value
Publication number	US-2019031814-A1
Application number	US-201716072976-A
Country	US
Kind code	A1
Filing date	Feb 13, 2017
Priority date	Feb 12, 2016
Publication date	Jan 31, 2019
Grant date	—

Abstract

Polycarbamide coating compositions and secondary diamine curing agents used to produce the coating compositions are disclosed. Curing agent compositions comprising: (a) the reaction product of bis(4-aminocyclohexyl) methane and ethyl ester of 2-butendioc acid; and (b) the reaction product of bis(4-amino-3-methylcyclohexyl)methane and ethyl ester of 2-butendioic acid; and (c) at least one polyol are also disclosed. One aspect of the disclosure relates to a non-aqueous coating composition comprising the disclosed amine curing agents with a polyisocyanate resin. The coating compositions are suitable for use as direct to metal coatings or top coats. Methods of producing the curing agents and the coating compositions are also disclosed.

First claim

1 . A curing agent composition, comprising:
at least one polyol; a first secondary diamine consisting of the reaction product of bis(4-aminocyclohexyl) methane and ethyl ester of 2-butenedioic acid; and a second secondary diamine consisting of the reaction product of bis(4-amino-3-methylcyclohexyl) methane and ethyl ester of 2-butenedioic acid.

2 . The curing agent composition of claim 1 , wherein each of the at least one polyol is selected from the group consisting of: polyols synthesized using succinic acid, glutaric acid, and adipic acid; 2-methyl-1,3-propanediol; and 1,4-cyclohexanedimethanol.

3 . The curing agent composition of claim 1 , wherein the first secondary diamine comprises 20% to 50% by weight of the curing agent composition, wherein the second secondary diamine comprises 20% to 50% by weight of the curing agent composition, and wherein the at least one polyol comprises 20% to 50% by weight of the curing agent composition.

4 . (canceled)

5 . The curing agent composition of claim 1 , wherein the first secondary diamine comprises 45% to 85% by weight of the curing agent composition, wherein the second secondary diamine comprises 5% to 30% of the curing agent composition, and wherein the at least one polyol comprises 5% to 30% by weight of the curing agent composition.

6 . (canceled)

7 . The curing agent composition of claim 1 , wherein the first secondary diamine and the second secondary diamine are present in equal amounts by weight, and wherein the second secondary amine and the polyol are present in equal amounts by weight.

8 . (canceled)

9 . The curing agent composition of claim 1 , wherein the first secondary diamine and the second secondary diamine are present at a weight ratio of at least 2:1, and wherein the second secondary amine and the polyol are present in equal amounts by weight.

10 . (canceled)

11 . The curing agent of claim 1 , wherein the first secondary diamine being represented by the formula:

and
wherein the second secondary diamine being represented by the formula:

12 - 22 . (canceled)

23 . A coating composition, comprising:
a polyisocyanate; at least one polyol; a first secondary diamine, wherein the first secondary diamine consists of the reaction product of bis(4-aminocyclohexyl) methane and ethyl ester of 2-butenedioic acid; and a second secondary diamine, wherein the second secondary diamine consists of the reaction product of bis(4-amino-3-methylcyclohexl) methane and ethyl ester of 2-butenedioic acid.

24 . The coating composition of claim 23 , wherein each of the at least one polyol is selected from the group consisting of: polyols synthesized using succinic acid, glutaric acid, and adipic acid; 2-methyl-1,3-propanediol; and 1, 4-cyclohexanedimethanol.

25 . The coating composition of claim 23 , further comprising at least one selected from the group consisting of solvents, pigments and defoamers.

26 . (canceled)

27 . The coating composition of claim 24 , wherein the coating composition comprises a solvent comprising methyl n-amyl ketone.

28 . The coating composition of claim 23 , further comprising titanium dioxide.

29 . The coating composition of claim 23 , wherein the polyisocyanate comprises a compound represented by the general formula: R(NCO) i , where R is an organic radical having a valence of i, where i is greater than or equal to 2, and where R is a substituted or unsubstituted hydrocarbon group.

30 . The coating composition of claim 23 , wherein the isocyanate comprises hexamethylene diisocyanate.

31 . A method comprising:
(a) reacting bis(4-aminocyclohexyl) methane and ethyl ester of 2-butendioc acid to create a first reaction product comprising a first secondary diamine; (b) reacting bis(4-amino-3-methylcyclohexl) methane and ethyl ester of 2-butenedioic acid, to create a second reaction product comprising a second secondary diamine; and (c) mixing the first reaction product, the second reaction product and at least one polyol to produce a curing agent.

32 . The method of claim 31 , wherein step (c) further comprises mixing the first reaction product, and the second reaction product, and at least one polyol in proportions that result in the first secondary diamine comprising 20% to 50% by weight of the curing agent composition, the second secondary diamine comprising 20% to 50%of the curing agent composition, and the at least one polyol comprising 20% to 50%by weight of the curing agent composition.

33 . (canceled)

34 . The method of claim 31 , wherein step (c) further comprises mixing the first reaction product, and the second reaction product, and at least one polyol in proportions that result in the first secondary diamine comprising 45% to 85% by weight of the curing agent composition, the second secondary diamine comprising 5% to 30% of the curing agent composition, and the at least one polyol comprising 5% to 30% by weight of the curing agent composition.

35 . (canceled)

36 . The method of claim 31 , wherein step (c) further comprises mixing the first reaction product, and the second reaction product, and at least one polyol in proportions that result in the first secondary diamine and the second secondary diamine being present in substantially equal amounts by weight in the curing agent composition, and the second secondary diamine and the at least one polyol being present in substantially equal amounts by weight in the curing agent composition.

37 . (canceled)

38 . The method of claim 31 , wherein step (c) further comprises mixing the first reaction product, and the second reaction product, and at least one polyol in proportions that result in the first secondary diamine and the second secondary diamine being present at a weight ratio of at least 2:1 in the curing agent composition, and the second secondary diamine and the at least one polyol being present in substantially equal amounts by weight in the curing agent composition.

39 . (canceled)

40 . The method of claim 31 , wherein step (a) further comprises reacting bis(4-aminocyclohexyl) methane and ethyl ester of 2-butendioc acid to create a first reaction product comprising a first secondary diamine being represented by the formula:

and
wherein step (b) further comprises reacting bis(4-amino-3-methylcyclohexl) methane and ethyl ester of 2-butenedioic acid, to create a second reaction product comprising a second secondary diamine being represented by the formula:

41 . (canceled)

42 . The method of claim 31 , wherein step (c) mixing the first reaction product, the second reaction product and at least one polyol to produce a curing agent, wherein each of the at least one polyol is selected from the group consisting of: polyols synthesized using succinic acid, glutaric acid, and adipic acid; 2-methyl-1,3-propanediol; and 1,4-cyclohexanedimethanol.

43 . The method of claim 31 , f

Assignees

• Evonik Degussa Gmbh

Inventors

• Hegedus Charles Raymond
• Ananthachar Sudhir
• Corby Thomas T
• Fazel Shafiq

Classifications

• C08K5/07

  Aldehydes; Ketones · CPC title

• C08G18/6651 Primary

  with compounds of group C08G18/3225 or polyamines of C08G18/38 · CPC title

• C08G18/792

  formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates · CPC title

• C08K3/22

  of metals · CPC title

• C08K2003/2241

  Titanium dioxide · CPC title