Process for curing thermoset resins

Patent metadata

Field	Value
Publication number	US-9840599-B2
Application number	US-201314421381-A
Country	US
Kind code	B2
Filing date	Aug 14, 2013
Priority date	Aug 17, 2012
Publication date	Dec 12, 2017
Grant date	Dec 12, 2017

Abstract

Process for curing a thermoset resin comprising the step of contacting said resin with (i) an imine of the structure C(R 2 )(R 3 )═N—R 1 wherein R 1 is selected from hydrogen, hydroxyl, linear or branched alkyl having 1-22 carbon atoms, cycloalkyl having 3-22 carbon atoms, aryl having 6 to 15 carbon atoms, and aralkyl having 7 to 22 carbon atoms, which alkyl, cycloalkyl, aryl, and aralkyl groups may be optionally substituted with one or more groups containing heteroatoms selected from S, O, P, and/or Si. R 2 is selected from C(R 6 )(R 5 )—C(═O)—R 4 , —C(R 6 )(R 5 )—C(═S)—R 4 , and —C(R 6 )(R 5 )—C(═N)—R 4 , wherein R 4 , R 5 , and R 6 are selected from hydrogen, linear or branched alkyl having 1-6 carbon atoms, cycloalkyl having 3-12 carbon atoms, aryl, aralkyl, alkoxy having 1-6 carbon atoms, and aryloxy. R 3 is selected from linear or branched alkyl having 1-22 carbon atoms, 1 cycloalkyl having 3-22 carbon atoms, aryl having 6 to 15 carbon atoms, and aralkyl having 7 to 22 carbon atoms, and (ii) methyl isopropyl ketone peroxide.

First claim

The invention claimed is:

1. A process for curing a thermoset resin comprising the step of contacting said resin with
(i) an imine of the structure C(R 2 )(R 3 )═N—R 1 wherein
R 1 is selected from the group consisting of hydrogen, hydroxyl, linear or branched alkyl having 1-22 carbon atoms, cycloalkyl having 3-22 carbon atoms, aryl having 6 to 15 carbon atoms, and aralkyl having 7 to 22 carbon atoms, said alkyl, cycloalkyl, aryl, and aralkyl groups may be optionally substituted with one or more groups containing heteroatoms selected from the group consisting of S, O, P, and Si,
R 2 is selected from C(R 6 )(R 5 )—C(═O)—R 4 , —C(R 6 )(R 5 )—C(═S)—R 4 , and —C(R 6 )(R 5 )—C(═N)—R4, wherein R 4 , R 5 , and R 6 are selected from the group consisting of hydrogen, linear or branched alkyl having 1-6 carbon atoms, cycloalkyl having 3-12 carbon atoms, aryl, aralkyl, alkoxy having 1-6 carbon atoms, and aryloxy,
R 3 is selected from the group consisting of linear or branched alkyl having 1-22 carbon atoms, cycloalkyl having 3-22 carbon atoms, aryl having 6 to 15 carbon atoms, and aralkyl having 7 to 22 carbon atoms, and

(ii) methyl isopropyl ketone peroxide.

2. The process according to claim 1 wherein R 2 has the formula —C(H)(R 5 )—C(═O)—R 4 .

3. The process according to claim 1 wherein R 5 is hydrogen.

4. The process according to claim 1 wherein R 4 is an alkoxy group and R 3 is an alkyl group.

5. The process according to claim 4 wherein R 4 is an ethoxy group.

6. The process according to claim 4 wherein and R 3 is a methyl group.

7. The process according to claim 1 wherein R 1 is selected from the group consisting of n-propyl, isopropyl, n-butyl, t-butyl, t-amyl, and cyclohexyl, and hydroxyethyl.

8. The process according to claim 1 wherein said resin is contacted with said imine in an amount of 0.5 to 2 parts by weight of imine per 100 parts by weight of resin.

9. The process according to claim 1 wherein said resin is contacted with said methyl isopropyl ketone peroxide in an amount of 1 to 2 parts by weight of imine per 100 parts by weight of resin.

Assignees

• Akzo Nobel Chemicals Int Bv

Inventors

• Koers Frederik Willem Karel
• Talma Auke Gerardus

Classifications

• C08K5/14 Primary

  Peroxides · CPC title

• C08J2335/02

  Characterised by the use of homopolymers or copolymers of esters (C08J2335/06, C08J2335/08 take precedence) · CPC title

• C08L67/06

  Unsaturated polyesters · CPC title

• C08K5/175

  containing COOH-groups; Esters or salts thereof · CPC title

• C08F283/01 Primary

  on to unsaturated polyesters {(C08F283/004 takes precedence)} · CPC title