# US 10,308,803 B2 · Epoxy resin containing silicone-modified epoxy resin and polyvalent carboxylic acid compound, and cured product thereof

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- Number: US 10,308,803 B2
- Document ID: US10308803B2
- Status: Granted
- Kind: B2
- Application number: 14/973,162
- Filed: 2015-12-17
- Published: 2016-06-23
- Granted: 2019-06-04
- Earliest claimed: 2014-12-18
- Assignees: Shin-Etsu Chemical Co., Ltd.; Nippon Kayaku Kabuhiki Kaisha
- Applicants: Shin-Etsu Chemical Co., Ltd.; Nippon Kayaku Kabushiki Kaisha
- Inventors: Toshio Shiobara; Junichi Sawada; Miyuki Wakao; Tsutomu Kashiwagi; Naofusa Miyagawa; Yoshihiro Kawada; Chie Sasaki
- Web page: https://patentgrep.com/patent/US10308803B2

## CPC

- C08L 63/00: Compositions of epoxy resins; Compositions of derivatives of epoxy resins
- C08G 59/3281: {containing silicon}
- C08G 59/42: Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
- C08G 59/4215: {cycloaliphatic}
- G02B 1/04: made of organic materials, e.g. plastics (G02B1/08 takes precedence)
- H10W 74/476: {Organic materials comprising silicon}
- C08L 2205/025: containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- H10W: GENERIC PACKAGES, INTERCONNECTIONS, CONNECTORS OR OTHER CONSTRUCTIONAL DETAILS OF DEVICES COVERED BY CLASS H10

## Abstract

A silicone-modified epoxy resin composition that offers a cured product excellent in low permeability to gas, mechanical strength, and heat resistance and transparency and further offers an optical semiconductor sealing material excellent in heat cycle resistance, and a cured epoxy resin product obtained by curing the composition. The epoxy resin composition comprises the following components (A) to (C): (A) a silicone-modified epoxy resin having a cyclic siloxane structure, (B) a silicone-modified epoxy resin having a branched siloxane structure, and (C) an epoxy resin curing agent containing a polyvalent carboxylic acid having a tricyclodecane structure and a carboxylic anhydride compound.

## Claims

### Claim 1

An epoxy resin composition comprising the following components (A) to (C):
(A) a silicone-modified epoxy resin represented by the formula (1),
wherein R1 represents a monovalent aliphatic hydrocarbon group having 1 to 6 carbon atoms or a monovalent aromatic hydrocarbon group having 6 to 12 carbon atoms; X is selected from a group consisting of a 3,4-epoxycyclohexylethyl group and a 3-glycidoxypropyl group; n represents an integer of 1 to 3; and a plurality of groups R1 or X present in the formula are the same or different from each other;
(B) a silicone-modified epoxy resin represented by the formula (2),
wherein R1 and X are each as defined above; and a plurality of groups R1 or X present in the formula are the same or different from each other; and
(C) an epoxy resin curing agent containing a polyvalent carboxylic acid represented by the formula (3) and a carboxylic anhydride compound:
wherein R is selected from the group consisting of methyl, COOH and H, wherein the components (A) to (C) are contained at the following ratios:
the amount of the component (A) is 20 to 80% by mass with respect to the total amount of the component (A) and the component (B),
the amount of the component (B) is 20 to 80% by mass with respect to the total amount of the component (A) and the component (B), and
wherein the mixing ratio is set such that the total number of carboxyl groups and carboxylic anhydride groups in the epoxy resin curing agent (C) is 0.4 to 0.7 mol with respect to 1 mol of the total number of epoxy groups in the whole epoxy resin composition.

### Claim 2 (depends on 1)

The epoxy resin composition according to claim 1,
wherein X is a 3,4-epoxycyclohexylethyl group.

### Claim 3 (depends on 1)

The epoxy resin composition according to claim 1, further comprising (D) an epoxy resin curing accelerator.

### Claim 4 (depends on 3)

The epoxy resin composition according to claim 3, further comprising (E) an antioxidant.

### Claim 5 (depends on 1)

The epoxy resin composition according to claim 1, wherein the epoxy resin composition offers a cured product in which the temperature at a relative maximum point of the loss coefficient (tanδ=E″/E′) indicated by a quotient of a loss elastic modulus (E″) divided by a storage elastic modulus (E′) is 145° C. or higher in DMA (dynamic mechanical analysis) analysis.

### Claim 6 (depends on 1)

A cured product prepared by curing an epoxy resin composition according to claim 1.

### Claim 7 (depends on 1)

The epoxy resin composition according to claim 1, wherein the epoxy resin composition is used for optical semiconductor sealing.

### Claim 8 (depends on 1)

The epoxy resin composition according to claim 1,
wherein the component (B) is a silicone-modified epoxy resin represented by the following formula: