Cyclic siloxane compounds and compositions comprising the same

Patent metadata

Field	Value
Publication number	US-10138258-B2
Application number	US-201615348106-A
Country	US
Kind code	B2
Filing date	Nov 10, 2016
Priority date	Nov 19, 2015
Publication date	Nov 27, 2018
Grant date	Nov 27, 2018

Abstract

A composition comprises a plurality of cyclic siloxane compounds. At least a portion of the cyclic siloxane compounds comprise first and second siloxane moieties having specified structures. A cyclic siloxane compound comprises a first siloxane moiety having a specified structure and a second siloxane moiety having a specified structure. An epoxy composition is made by reacting a composition comprising a plurality of cyclic siloxane compounds, an epoxy resin, and a curative. An epoxy composition is made by reacting a cyclic siloxane compound, an epoxy resin, and a curative.

First claim

What is claimed is:

1. A composition comprising a plurality of cyclic siloxane compounds, at least a portion of the cyclic siloxane compounds comprising a first siloxane moiety and a second siloxane moiety, wherein:
(a) the first siloxane moiety is 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;
(b) the second siloxane moiety is selected from the group consisting of moieties conforming to the structure of Formula (X)

where R 10 is a methyl group; R 11 is a 2-methylethane-1,2-diyl group; and R 12 is a phenyl group; and
(c) about 35% or more of the cyclic siloxane compounds present in the composition comprise at least one first siloxane moiety and at least one second siloxane moiety.

2. The composition of claim 1 , wherein about 10% or less of the cyclic siloxane compounds present in the composition contain only second siloxane moieties.

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

4. The composition of claim 1 , 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. A cyclic siloxane compound comprising a plurality of siloxane moieties, the compound comprising:
(a) at least one first siloxane moiety conforming to the structure of Formula (C)

wherein R 101 is selected from the group consisting of alkyl groups; and R 102 is a group comprising a cyclic ether moiety; and
(b) at least one second siloxane moiety conforming to the structure of Formula (CX)

wherein R 110 is a methyl group; R 111 is a 2-methylethane-1,2-diyl group; and R 112 is a phenyl group.

7. The cyclic siloxane compound of claim 6 , wherein R 102 comprises an epoxide moiety.

8. The cyclic siloxane compound of claim 6 , wherein R 102 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.

9. The cyclic siloxane compound of claim 8 , wherein R 5 is a propane-1,3-diyl group, and R 6 is a glycidyl group.

10. An epoxy composition made by reacting:
(a) a composition comprising a plurality of cyclic siloxane compounds, at least a portion of the cyclic siloxane compounds comprising a first siloxane moiety and a second siloxane moiety, wherein:
(i) the first siloxane moiety is 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;
(ii) the second siloxane moiety is selected from the group consisting of moieties conforming to the structure of Formula (X)

where R 10 is a methyl group; R 11 is a 2-methylethane-1,2-diyl group; and R 12 is a phenyl group and
(iii) about 35% or more of the cyclic siloxane compounds present in the composition comprise at least one first siloxane moiety and at least one second siloxane moiety;

(b) an epoxy resin; and
(c) a curative.

11. The epoxy composition of claim 10 , wherein R 2 comprises an epoxide moiety.

12. The epoxy composition of claim 10 , 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.

13. The epoxy composition of claim 12 , wherein R 5 is a propane-1,3-diylgroup, and R 6 is a glycidyl group.

14. The epoxy composition of claim 10 , wherein the epoxy composition is made by reacting the composition comprising a plurality of cyclic siloxane compounds, the epoxy resin, the curative, and a second siloxane compound, and the second siloxane compound is an amine-terminated, substantially linear siloxane compound comprising a plurality of siloxane moieties, wherein:
(a) a portion of the siloxane moieties are independently selected from the group consisting of siloxane moieties conforming to the structure of Formula (CC)

wherein R 201 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; R 202 is selected from the group consisting of alkanediyl groups and alkenediyl groups; and R 203 is selected from the group consisting of aryl groups, substituted aryl groups, heteroaryl groups, and substituted heteroaryl groups;
(b) a portion of the siloxane moieties are independently selected from the group consisting of siloxane moieties conforming to the structure of Formula (CCX)

wherein R 211 and R 212 are independently 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
(c) the amine-terminated, substantially linear siloxane compound comprises terminal groups conforming to the structure of Formula (CCXX) and Formula (CCXXI)

wherein R 220 is selected from the group consisting of hydrogen, 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; R 221 is selected from the group consisting of alkanediyl groups and substituted alkanediyl groups; R 222 and R 223 are independentl

Assignees

• Milliken & Co

Inventors

• Christiano Steven P
• Hoy Olha V
• Fresia Megan J
• Hayes Nathaniel O
• Lever John G

Classifications

• C08L63/00

  Compositions of epoxy resins; Compositions of derivatives of epoxy resins · CPC title

• C07F7/0812

  comprising a heterocyclic ring · CPC title

• C07F7/21 Primary

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

• C08G59/1438

  containing oxygen · CPC title

• C08G59/504

  containing an atom other than nitrogen belonging to the amine group, carbon and hydrogen · CPC title