Ketimines of benzylated polyamines as curing agents

Patent metadata

Field	Value
Publication number	US-9708248-B2
Application number	US-201514861154-A
Country	US
Kind code	B2
Filing date	Sep 22, 2015
Priority date	Sep 22, 2014
Publication date	Jul 18, 2017
Grant date	Jul 18, 2017

Abstract

Ketimines of benzylated polyamines and MEK are disclosed. The ketimines can be used as an epoxy curing agent and impart improved potlife, and enhanced blush and chemical resistance of cured epoxy coatings.

First claim

The invention claimed is:

1. A compound comprising a ketimine of benzylated polyamines represented by the formula:

wherein R1 is benzyl, R2 is H, alkyl, cycloaliphatic or benzyl;
R3 and R4 are (CH 2 ) m provided that m=2-6; n=1-3; and R5 and R6 are C1-C10 linear or branched aliphatic or cycloaliphatic or substituted cycloaliphatic hydrocarbon or aromatic hydrocarbon, and R7 is H or C3-C10 containing linear or branched aliphatic or cycloaliphatic or substituted cycloaliphatic hydrocarbon or aromatic hydrocarbon or hydroxyl.

2. A method for making a ketimine of benzylated polyamines comprising contacting at least one ketone with at least one benzylated polyamine;
wherein the contacting employs the following formula:

wherein R1 is benzyl, R2 is H, alkyl, cycloaliphatic or benzyl;
R3 and R4 are (CH 2 ) m provided that m=2-6; n=1-3; and R5 and R6 are C1-C10 linear or branched aliphatic or cycloaliphatic or substituted cycloaliphatic hydrocarbon or aromatic hydrocarbon, and R7 is H or C3-C10 containing linear or branched aliphatic or cycloaliphatic or substituted cycloaliphatic hydrocarbon or aromatic hydrocarbon or hydroxyl.

3. The method of claim 2 wherein the ketone comprises methyl ethyl ketone.

4. A composition comprising at least one ketimine of benzlyated polyamines represented by the formula:

wherein R1 is benzyl, R2 is H, alkyl, cycloaliphatic or benzyl;
R3 and R4 are (CH 2 ) m provided that m=2-6; n=1-3; and R5 and R6 are C1-C10 linear or branched aliphatic or cycloaliphatic or substituted cycloaliphatic hydrocarbon or aromatic hydrocarbon, and R7 is H or C3-C10 containing linear or branched aliphatic or cycloaliphatic or substituted cycloaliphatic hydrocarbon or aromatic hydrocarbon or hydroxyl.

5. An epoxy curing agent comprising at least one ketimine of benzylated polyamines represented by the formula:

wherein R1 is benzyl, R2 is H, alkyl, cycloaliphatic or benzyl;
R3 and R4 are (CH 2 ) m provided that m=2-6; n=1-3; and R5 and R6 are C1-C10 linear or branched aliphatic or cycloaliphatic or substituted cycloaliphatic hydrocarbon or aromatic hydrocarbon, and R7 is H or C3-C10 containing linear or branched aliphatic or cycloaliphatic or substituted cycloaliphatic hydrocarbon or aromatic hydrocarbon or hydroxyl.

6. The epoxy curing agent of claim 5 further comprising at least one member selected from the group consisting of modified amines, like, aliphatic amine adducts, cycloaliphatic amine adducts, unmodified cycloaliphatic amine, Mannich Base, Phenalkamines, Polyamides and Amidoamines.

7. A composition comprising at least one ketimine of benzylated polyamines and at least one epoxy resin;
wherein the at least one ketamine of benzylated polyamines is represented by the formula:

wherein R1 is benzyl, R2 is H, alkyl, cycloaliphatic or benzyl;
R3 and R4 are (CH 2 ) m provided that m=2-6; n=1-3; and R5 and R6 are C1-C10 linear or branched aliphatic or cycloaliphatic or substituted cycloaliphatic hydrocarbon or aromatic hydrocarbon, and R7 is H or C3-C10 containing linear or branched aliphatic or cycloaliphatic or substituted cycloaliphatic hydrocarbon or aromatic hydrocarbon or hydroxyl.

Assignees

• Evonik Degussa Gmbh

Inventors

• Minnich Kristen Elaine
• Rufo Marcelo
• Vedage Gamini Ananda

Classifications

• C08G59/50

  Amines · CPC title

• C07C249/02 Primary

  of compounds containing imino groups · CPC title

• C07C251/08 Primary

  being acyclic · CPC title

• C08G59/56

  together with other curing agents · CPC title

• C08G59/4042

  Imines; Imides · CPC title