Adduct of an amine and a cyclic siloxane compound

Patent metadata

Field	Value
Publication number	US-10155839-B2
Application number	US-201615348151-A
Country	US
Kind code	B2
Filing date	Nov 10, 2016
Priority date	Nov 19, 2015
Publication date	Dec 18, 2018
Grant date	Dec 18, 2018

Abstract

A composition comprises an adduct produced by reacting an amine compound and a cyclic siloxane compound. The amine compound comprises two or more amine groups independently selected from the group consisting of primary amine groups and secondary amine groups. The cyclic siloxane compound comprises two or more first siloxane moieties that contain cyclic ether moieties. An epoxy composition is made by reacting an epoxy resin and the composition comprising the adduct.

First claim

What is claimed is:

1. A composition comprising an adduct produced by reacting an amine compound and a cyclic siloxane compound, wherein (a) the amine compound comprises two or more amine groups independently selected from the group consisting of primary amine groups and secondary amine groups and (b) the cyclic siloxane compound comprises two or more first siloxane moieties and one or more second siloxane moieties, the first siloxane moieties being independently selected from the group consisting of moieties conforming to the structure of Formula (I)

where R 1 is selected from the group consisting of alkyl groups, substituted alkyl groups, cycloalkyl groups, substituted cycloalkyl groups, alkenyl groups, substituted alkenyl groups, cycloalkenyl groups, substituted cycloalkenyl groups, heterocyclyl groups, substituted heterocyclyl groups, aryl groups, substituted aryl groups, heteroaryl groups, and substituted heteroaryl groups, and R 2 is a group comprising a cyclic ether moiety, and the second siloxane moieties being independently selected from the group consisting of moieties of Formula (X)

where R 10 is selected from the group consisting of alkyl groups, substituted alkyl groups, cycloalkyl groups, substituted cycloalkyl groups, alkenyl groups, substituted alkenyl groups, cycloalkenyl groups, substituted cycloalkenyl groups, heterocyclic groups, substituted heterocyclic groups, aryl groups, substituted aryl groups, heteroaryl groups, and substituted heteroaryl groups; R 11 is selected from the group consisting of alkanediyl groups and alkenediyl groups; and R 12 is selected from the group consisting of aryl groups, substituted aryl groups, heteroaryl groups, and substituted heteroaryl groups.

2. The composition of claim 1 , wherein R 2 comprises an epoxide moiety.

3. The composition of claim 2 , wherein R 2 is selected from the group consisting of 5,6-epoxyhexyl and 2-(3,4-epoxycyclohexyl)ethyl.

4. The composition of claim 2 , wherein R 2 is a group conforming to the structure —R 5 —O—R 6 , where R 5 is an alkanediyl group and R 6 is a group comprising an epoxide moiety.

5. The composition of claim 4 , wherein R 5 is a propane-1,3-diyl group, and R 6 is a glycidyl group.

6. The composition of claim 1 , wherein R 1 is selected from the group consisting of alkyl groups.

7. The composition of claim 6 , wherein R 1 is a methyl group.

8. The composition of claim 1 , wherein R 10 is an alkyl group, R 11 is an alkanediyl group, and R 12 is an aryl group.

9. The composition of claim 8 , wherein R 10 is a methyl group, R 11 is a 2-methylethane-1,2-diyl group, and R 12 is a phenyl group.

10. The composition of claim 1 , wherein the cyclic siloxane compound comprises two or more second siloxane moieties.

11. The composition of claim 1 , wherein the cyclic siloxane compound comprises four to eight siloxane moieties.

12. An epoxy composition produced by reacting an epoxy resin and the composition of claim 1 .

13. An epoxy composition produced by reacting an epoxy resin and a composition comprising an adduct produced by reacting an amine compound and a cyclic siloxane compound, wherein (a) the amine compound comprises two or more amine groups independently selected from the group consisting of primary amine groups and secondary amine groups and (b) the cyclic siloxane compound comprises two or more first siloxane moieties, the first siloxane moieties being independently selected from the group consisting of moieties conforming to the structure of Formula (I)

where R 1 is selected from the group consisting of alkyl groups, substituted alkyl groups, cycloalkyl groups, substituted cycloalkyl groups, alkenyl groups, substituted alkenyl groups, cycloalkenyl groups, substituted cycloalkenyl groups, heterocyclyl groups, substituted heterocyclyl groups, aryl groups, substituted aryl groups, heteroaryl groups, and substituted heteroaryl groups, and R 2 is a group comprising a cyclic ether moiety.

14. The epoxy composition of claim 13 , wherein R 2 comprises an epoxide moiety.

15. The epoxy composition of claim 14 , wherein R 2 is selected from the group consisting of 5,6-epoxyhexyl and 2-(3,4-epoxycyclohexyl)ethyl.

16. The composition of claim 14 , wherein R 2 is a group conforming to the structure —R 5 —O—R 6 , where R 5 is an alkanediyl group and R 6 is a group comprising an epoxide moiety.

17. The composition of claim 16 , wherein R 5 is a propane-1,3-diyl group, and R 6 is a glycidyl group.

18. The composition of claim 13 , wherein R 1 is selected from the group consisting of alkyl groups.

19. The composition of claim 18 , wherein R 1 is a methyl group.

Assignees

• Milliken & Co

Inventors

• Christiano Steven P
• Hoy Olha V
• Hanssen Robbie W J M

Classifications

• C08L83/14

  in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms (C08L83/10 takes precedence) · CPC title

• C08G59/1477 Primary

  containing nitrogen · CPC title

• C08L59/00

  Compositions of polyacetals; Compositions of derivatives of polyacetals (of polyvinyl acetals C08L29/14) · CPC title

• C07F7/21 Primary

  Cyclic compounds having at least one ring containing silicon, but no carbon in the ring · CPC title

• C08G77/38

  Polysiloxanes modified by chemical after-treatment · CPC title