Silicone-modified epoxy resin, composition containing said epoxy resin, and cured product thereof

Patent metadata

Field	Value
Publication number	US-9944760-B2
Application number	US-201515120482-A
Country	US
Kind code	B2
Filing date	Feb 18, 2015
Priority date	Feb 19, 2014
Publication date	Apr 17, 2018
Grant date	Apr 17, 2018

Abstract

The purpose of the present invention is to provide a silicone-modified epoxy resin which produces a cured product having excellent low gas permeability and strength; a composition of the resin; and an epoxy resin cured product obtainable by curing the composition.
Disclosed is an epoxy resin represented by the following Formula (1):

wherein R 1 independently represents a monovalent aromatic hydrocarbon group having 6 to 12 carbon atoms; R 2 independently represents a monovalent aliphatic hydrocarbon group having 1 to 12 carbon atoms; R 3 independently represents a monovalent aliphatic hydrocarbon group having 1 to 12 carbon atoms or a monovalent aromatic hydrocarbon group having 6 to 12 carbon atoms; R 4 represents an oxygen atom or a divalent hydrocarbon group having an aliphatic cyclic structure; R 5 represents silicone chain having a norbornane epoxy structure at either end; and X represents an organic group having a norbornane epoxy group.

First claim

What is claimed is:

1. A silicone-modified epoxy resin having a branched structure represented by the following Formula (1):

wherein R 1 independently represents a monovalent aromatic hydrocarbon group having 6 to 12 carbon atoms;
R 2 independently represents a monovalent aliphatic hydrocarbon group having 1 to 12 carbon atoms;
R 3 independently represents a monovalent aliphatic hydrocarbon group having 1 to 12 carbon atoms or a monovalent aromatic hydrocarbon group having 6 to 12 carbon atoms;
R 4 represents an oxygen atom or a divalent hydrocarbon group represented by the formula:

provided that at least one R 4 represents the divalent hydrocarbon group represented by the formula (2);
wherein R 6 represents a single bond or an alkylene group having 1 to 6 carbon atoms; and m represents an integer from 0 to 2;
R 5 represents a group represented by the following Formula (3):

wherein R 1 , R 2 , R 3 , and R 4 respectively have the same meanings as described above; r and s each represent an integer from 0 to 10; X represents a structure represented by the following Formula (5); and the repeating units represented by r and s in the formula respectively include a block unit structure and/or a random unit structure; or
R 5 represents a group represented by the following Formula (4):

wherein R 2 , R 4 , and X respectively have the same meanings as described above;
X represents a group represented by the following Formula (5):

wherein R 7 represents a single bond or an alkylene group having 1 to 6 carbon atoms and optionally containing an ester bond or an ether bond; and m represents an integer from 0 to 2; and
n represents an integer from 1 to 10; and p and q each represent an integer from 0 to 10, provided that the repeating units represented by p, n, and q in the formula respectively include a block unit structure and/or a random unit structure.

2. The silicone-modified epoxy resin having a branched structure according to claim 1 , wherein in Formula (1), R 1 represents a group selected from a phenyl group, a benzyl group, a 2-phenylethyl group, and a 2-phenylpropyl group.

3. The silicone-modified epoxy resin having a branched structure according to claim 1 , wherein in Formula (1), n represents 1 or 2.

4. The silicone-modified epoxy resin according to claim 1 , wherein the silicone-modified epoxy resin is an addition reaction product between a compound represented by the following Formula (6):

wherein m has the same meaning as described above; and R 8 represents a single bond or an alkylene group having 1 to 4 carbon atoms and optionally containing an ester bond or an ether bond,

and a compound represented by the following Formula (7):

wherein R 1 to R 4 , n, p, and q respectively have the same meanings as described above; and R 9 represents a group represented by the following Formula (8):

wherein R 1 to R 4 , R 9 , r, and s respectively have the same meanings as described above, or
R 9 represents a group represented by the following Formula (9):

wherein R 2 and R 4 respectively have the same meanings as described above.

5. The silicone-modified epoxy resin according to claim 1 , wherein the silicone-modified epoxy resin is obtained by oxidizing a polyvalent olefin-based compound represented by the following Formula (10):

wherein R 1 to R 4 , n, p, and q respectively have the same meanings as described above; and R 10 represents a group represented by the following Formula (11):

wherein R 1 to R 4 , R 10 , r, and s respectively have the same meanings as described above,
or the following Formula (12):

and Y represents a group represented by the following Formula (13):

wherein R 7 and m respectively have the same meanings as described above.

6. An epoxy resin composition comprising (A) a silicone-modified epoxy resin according to claim 1 ; and (B) an epoxy resin curing agent.

7. An epoxy resin composition comprising (A) a silicone-modified epoxy resin according claim 1 ; and (C) an epoxy resin curing accelerator.

8. The epoxy resin composition according to claim 6 , wherein the epoxy resin curing agent is at least any one selected from an amine-based curing agent, a phenolic curing agent, an acid anhydride curing agent, and a polyvalent carboxylic acid resin.

9. A cured product formed by curing the epoxy resin composition according to claim 6 .

10. A polyvalent olefin-based compound represented by the following formula (10):

wherein R 1 independently represents a monovalent aromatic hydrocarbon group having 6 to 12 carbon atoms;
R 2 independently represents a monovalent aliphatic hydrocarbon group having 1 to 12 carbon atoms;
R 3 independently represents a monovalent aliphatic hydrocarbon group having 1 to 12 carbon atoms or a monovalent aromatic hydrocarbon group having 6 to 12 carbon atoms;
R 4 represents an oxygen atom or a divalent hydrocarbon group represented by the formula:

provided that at least one R 4 represents the divalent hydrocarbon group represented by the formula (2);

R 6 represents a single bond or an alkylene group having 1 to 6 carbon atoms; and m represents an integer from 0 to 2;
n represents an integer from 1 to 10;
p and q each represent an integer from 0 to 10, provided that the repeating units represented by p, n, and q in the formula respectively include a block unit structure and/or a random unit structure;
and R 10 represents a group represented by the following Formula (11):

wherein R 1 to R 4 , and R 10 , respectively have the same meanings as described above;

wherein r and s each represent an integer from 0 to 10; and the repeating units represented by r and s in the formula respectively include a block unit structure and/or a random unit structure;
or the following Formula (12):

Assignees

• Shinetsu Chemical Co
• Nippon Kayaku Kk

Inventors

• Shiobara Toshio
• Sawada Junichi
• Wakao Miyuki
• Kashiwagi Tsutomu
• Miyagawa Naofusa
• Kawada Yoshihiro
• Sasaki Chie
• Taniguchi Naosuke

Classifications

• C08G59/027

  obtained by epoxidation of unsaturated precursor, e.g. polymer or monomer · CPC title

• C08G59/4276

  Polyesters · CPC title

• C08G59/688

  containing phosphorus · CPC title

• C08K5/12

  of cyclic polycarboxylic acids · CPC title

• C08G59/4215

  cycloaliphatic · CPC title