# US 2015/0104651 A1 · Epoxy resin, method for producing expoxy resin, epoxy resin composition, cured product thereof, and heat-dissipating resin material

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- Number: US 2015/0104651 A1
- Document ID: US20150104651A1
- Status: Published application
- Kind: A1
- Application number: 14/389,068
- Filed: 2013-03-19
- Published: 2015-04-16
- Earliest claimed: 2012-03-27
- Assignees: DIC Corporation
- Applicants: DIC Corporation
- Inventors: Kazuo Arita; Hajime Watanabe
- Web page: https://patentgrep.com/patent/US20150104651A1

## CPC

- C08J 7/043: Improving the adhesiveness of the coatings per se, e.g. forming primers (adhesives in the form of films or foils characterised by the primer layers between the polymer carriers and the adhesives C09J7/50)
- C08G 59/1494: {followed by a further chemical treatment thereof}
- C08G 59/22: Di-epoxy compounds
- C08G 59/245: {aromatic}
- C08J 5/244: {using glass fibres}
- C08J 7/0427: {with only one layer of a composition containing a polymer binder (with more layers C08J7/042)}
- C08K 3/013: Fillers, pigments or reinforcing additives
- C08K 3/22: of metals
- H05K 1/0209: {External configuration of printed circuit board adapted for heat dissipation, e.g. lay-out of conductors, coatings}
- H05K 1/0326: {containing O}
- C08J 2363/00: Characterised by the use of epoxy resins; Derivatives of epoxy resins
- C08K 7/18: inorganic
- C08K 2003/2227: {of aluminium}
- H05K 3/4676: {Single layer compositions}
- H05K 2201/0209: Inorganic, non-metallic particles
- Y10T 428/31529: Next to metal
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- H05K: PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

The present invention provides an epoxy resin having a low melting point, low melt viscosity, excellent solvent solubility, and excellent processability. Also, the present invention provides an epoxy resin composition and a cured product thereof having excellent fluidity, processability, flexibility, adhesion, and thermal conductivity. The epoxy resin is represented by general formula (I) below (Q: an alkylene chain having a C1-C9 linear part which may have a C1-C18 alkyl group in a side chain, or a linkage chain having an ether bond present between two continuous methylene groups in the alkylene chain; A: a phenylene unit in which 2 to 4 phenylene groups are bonded directly or through a linkage chain, or a naphthylene unit, n: 0 to 10). The epoxy resin composition contains the epoxy resin and a curing agent. The composition includes the epoxy resin.

## Claims

### Claim 1

An epoxy resin represented by general formula (I) below,
[in the formula, Q each independently represent a linear alkylene chain having 1 to 9 carbon atoms, a branched alkylene chain having a structure in which an alkyl group having 1 to 18 carbon atoms is bonded to a carbon atom of the linear alkylene chain, or a linkage chain having an ether bond present between two continuous methylene groups in the alkylene chain; A each independently represent a phenylene unit represented by general formula (i) below
{in the formula, Y each independently represent a halogen atom, a hydrocarbon group having 1 to 8 carbon atoms, or an alkoxyl group having 1 to 8 carbon atoms; X represents a single bond, a —O— group, a —CH═CH— group, a —CH═C(CH3)— group, a —CH═C(CN)— group, a —C≡C— group, a —CH═N— group, a —CH═CH—CO— group, a —N═N— group, a —COO— group, a —CONH— group, or a —CO— group; 1 each independently represent an integer of 0 to 4; and m represents an integer of 1 to 3}, or a naphthylene unit represented by general formula (ii) below
{in the formula, Z each independently represent a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 8 carbon atoms, or an alkoxyl group having 1 to 8 carbon atoms}; and n represents an integer of 0 to 10].

### Claim 2 (depends on 1)

The epoxy resin according to claim 1, wherein in the general formula (I), A each independently represent a structural site represented by any one of general formulae (i-1) to (i-3) and (ii-1) below, and Q each independently represent a linear alkylene chain having 3 to 7 carbon atoms or ethyleneoxyethylene.

### Claim 3

A method for producing an epoxy resin, the method comprising reacting a diol compound (a) with at least one diglycidyl ether compound (q), the diol compound (a) being represented by general formula (1),
{in the formula, Y each independently represent a halogen atom, a hydrocarbon group having 1 to 8 carbon atoms, or an alkoxyl group having 1 to 8 carbon atoms; X represents a single bond, a —O— group, a —CH═CH— group, a —CH═C(CH3)— group, a —CH═C(CN)— group, a —C≡C— group, a —CH═N— group, a —CH═CH—CO— group, a —N═N— group, a —COO— group, a —CONH— group, or a —CO— group; 1 each independently represent an integer of 0 to 4; and m represents an integer of 1 to 3}, or general formula (2) below,
{in the formula, Z each independently represent a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 8 carbon atoms, or an alkoxyl group having 1 to 8 carbon atoms}, and the at least one diglycidyl ether compound (q) being selected from the group consisting of a diglycidyl ether of a linear alkylene diol having 1 to 9 carbon atoms, a diglycidyl ether of a branched alkylene diol having a structure in which an alkyl group having 1 to 18 carbon atoms is bonded to a carbon atom of the linear alkylene diol, and a diglycidyl ether of a diol compound having an ether bond present between two continuous methylene groups in the alkylene diol.

### Claim 4 (depends on 3)

The method for producing an epoxy resin according to claim 3, wherein the diol compound (a) is a diol compound represented by any one of general formulae (1-1) to (1-3) and (2-1) below, and the diglycidyl ether compound (q) is a diglycidyl ether of a linear alkylene diol having 2 to 7 carbon atoms or diethylene glycol.

### Claim at position 5

5-12. (canceled)

### Claim 13

An epoxy resin composition comprising an epoxy resin and a curing agent, the epoxy resin being represented by general formula (I) below,
[in the formula, Q each independently represent a linear alkylene chain having 1 to 9 carbon atoms, a branched alkylene chain having a structure in which an alkyl group having 1 to 18 carbon atoms is bonded to a carbon atom of the linear alkylene chain, or a linkage chain having an ether bond present between two continuous methylene groups in the alkylene chain; A each independently represent a phenylene unit represented by general formula (i) below
{in the formula, Y each independently represent a halogen atom, a hydrocarbon group having 1 to 8 carbon atoms, or an alkoxyl group having 1 to 8 carbon atoms; X represents a single bond, a —O— group, a —CH═CH— group, a —CH═C(CH3)— group, a —CH═C(CN)— group, a —C≡C— group, a —CH═N— group, a —CH═CH—CO— group, a —N═N— group, a —COO— group, a —CONH— group, or a —CO— group; 1 each independently represent an integer of 0 to 4; and m represents an integer of 1 to 3}, or a naphthylene unit represented by general formula (ii) below
{in the formula, Z each independently represent a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 8 carbon atoms, or an alkoxyl group having 1 to 8 carbon atoms}; and n represents an integer of 0 to 10].

### Claim 14 (depends on 13)

The epoxy resin composition according to claim 13, wherein in the general formula (I), A each independently represent a structural site represented by any one of general formulae (i-1) to (i-3) and (ii-1) below, and Q each independently represent a linear alkylene chain having 3 to 7 carbon atoms or ethyleneoxyethylene.

### Claim 15 (depends on 13)

A cured product produced by curing the epoxy resin position according to claim 13.

### Claim 16 (depends on 14)

A cured product produced by curing the epoxy resin position according to claim 14.

### Claim 17

A heat-dissipating resin material comprising an epoxy resin, a curing agent, and an inorganic filler, the epoxy resin being represented by general formula (I) below,
[in the formula, Q each independently represent a linear alkylene chain having 1 to 9 carbon atoms, a branched alkylene chain having a structure in which an alkyl group having 1 to 18 carbon atoms is bonded to a carbon atom of the linear alkylene chain, or a linkage chain having an ether bond present between two continuous methylene groups in the alkylene chain; A each independently represent a phenylene unit represented by general formula (i) below
{in the formula, Y each independently represent a halogen atom, a hydrocarbon group having 1 to 8 carbon atoms, or an alkoxyl group having 1 to 8 carbon atoms; X represents a single bond, a —O— group, a —CH═CH— group, a —CH═C(CH3)— group, a —CH═C(CN)— group, a —C≡C— group, a —CH═N— group, a CH═CH—CO— group, a —N═N— group, a —COO— group, a —CONH— group, or a —CO— group; 1 each independently represent an integer of 0 to 4; and m represents an integer of 1 to 3}, or a naphthylene unit represented by general formula (ii) below
{in the formula, Z each independently represent a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 8 carbon atoms, or an alkoxyl group having 1 to 8 carbon atoms}; and n represents an integer of 0 to 10], wherein a ratio of the inorganic filler is within a range of 20% to 95% by mass.

### Claim 18 (depends on 17)

The heat dissipating resin material according to claim 17, wherein in the general formula (I), A each independently represent a structural site represented by any one of general formulae (i-1) to (i-3) and (ii-1) below, and Q each independently represent a linear alkylene chain having 3 to 7 carbon atoms or ethyleneoxyethylene.

### Claim 19

A semiconductor encapsulating material comprising an epoxy resin, a curing agent, and an inorganic filler, the epoxy resin being represented by general formula (I) below,
[in the formula, Q each independently represent a linear alkylene chain having 1 to 9 carbon atoms, a branched alkylene chain having a structure in which an alkyl group having 1 to 18 carbon atoms is bonded to a carbon atom of the linear alkylene chain, or a linkage chain having an ether bond present between two continuous methylene groups in the alkylene chain; A each independently represent a phenylene unit represented by general formula (i) below
{in the formula, Y each independently represent a halogen atom, a hydrocarbon group having 1 to 8 carbon atoms, or an alkoxyl group having 1 to 8 carbon atoms; X represents a single bond, a —O— group, a —CH═CH— group, a —CH═C(CH3)— group, a —CH═C(CN)— group, a —C≡C— group, a —CH═N— group, a —CH═CH—CO— group, a —N═N— group, a —COO— group, a —CONH— group, or a —CO— group; 1 each independently represent an integer of 0 to 4; and m represents an integer of 1 to 3}, or a naphthylene unit represented by general formula (ii) below
{in the formula, Z each independently represent a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 8 carbon atoms, or an alkoxyl group having 1 to 8 carbon atoms}; and n represents an integer of 0 to 10], wherein a ratio of the inorganic filler is within a range of 20% to 95% by mass.

### Claim 20 (depends on 19)

The semiconductor encapsulating material according to claim 19, wherein in the general formula (I), A each independently represent a structural site represented by any one of general formulae (i-1) to (i-3) and (ii-1) below, and Q each independently represent a linear alkylene chain having 3 to 7 carbon atoms or ethyleneoxyethylene.

### Claim 21

A circuit board produced by heat-pressure-molding a plate-shaped material and a copper foil laminated on a surface of the plate, the plate-shaped material being composed of a varnish containing an epoxy resin, a curing agent, and an organic solvent, and the epoxy resin being represented by general formula (I) below,
[in the formula, Q each independently represent a linear alkylene chain having 1 to 9 carbon atoms, a branched alkylene chain having a structure in which an alkyl group having 1 to 18 carbon atoms is bonded to a carbon atom of the linear alkylene chain, or a linkage chain having an ether bond present between two continuous methylene groups in the alkylene chain; A each independently represent a phenylene unit represented by general formula (i) below
{in the formula, Y each independently represent a halogen atom, a hydrocarbon group having 1 to 8 carbon atoms, or an alkoxyl group having 1 to 8 carbon atoms; X represents a single bond, a —O— group, a —CH═CH— group, a —CH═C(CH3)— group, a —CH═C(CN)— group, a —C≡C— group, a —CH═N— group, a —CH═CH—CO— group, a —N═N— group, a —COO— group, a —CONH— group, or a —CO— group; 1 each independently represent an integer of 0 to 4; and m represents an integer of 1 to 3}, or a naphthylene unit represented by general formula (ii) below
{in the formula, Z each independently represent a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 8 carbon atoms, or an alkoxyl group having 1 to 8 carbon atoms}; and n represents an integer of 0 to 10].

### Claim 22 (depends on 21)

The circuit board according to claim 21, wherein in the general formula (I), A each independently represent a structural site represented by any one of general formulae (i-1) to (i-3) and (ii-1) below, and Q each independently represent a linear alkylene chain having 3 to 7 carbon atoms or ethyleneoxyethylene.