Epoxy resin composition, process for producing same, and uses of said composition

Patent metadata

Field	Value
Publication number	US-11066510-B2
Application number	US-202016882016-A
Country	US
Kind code	B2
Filing date	May 22, 2020
Priority date	Jul 10, 2015
Publication date	Jul 20, 2021
Grant date	Jul 20, 2021

Abstract

The present invention provides an epoxy resin composition that can produce a cured product maintaining good dielectric characteristics (low dielectric constant and low dielectric loss tangent), and having high adhesion strength to metal; and also provides a process for producing the same, a cured product obtained by curing the epoxy resin composition, and use thereof. The present invention includes an epoxy resin composition comprising an epoxy resin, an acid anhydride-based curing agent, and a curing accelerator, the epoxy resin being represented by the formula (1):wherein X is a divalent group obtained by removing two hydrogen atoms from a hydrocarbon ring, or a divalent group represented by the formula (2):wherein Y is a bond, a C1-6 alkylene group, etc.;R1 is the same or different, and is a C1-18 alkyl group, etc.,R2 is the same or different, and is a C1-18 alkylene group, etc.,R3 is the same or different, and is a C1-18 alkyl group, etc., andn is the same or different, and is an integer of 0 to 3. The present invention also includes a process for producing the same, a cured product of the epoxy resin composition, and use thereof.

First claim

The invention claimed is:

1. A method of improving adhesion strength of a cured product of an epoxy resin composition to metal, the method comprising:
(1) mixing an epoxy resin, an acid anhydride-based curing agent, and a curing accelerator,
(2) applying the mixture of step (1) on a metal, and
(3) curing the mixture of step (1) on the metal,
wherein the epoxy resin is represented by the formula (1):

wherein X is a divalent group obtained by removing two hydrogen atoms from a hydrocarbon ring, or a divalent group represented by the formula (2):

wherein Y is a bond, a C 1-6 alkylene group, an oxygen atom (—O—), or a group represented by the formula: —S(O) m — wherein m is 0, 1, or 2;
R 1 is the same or different, and is a C 1-18 alkyl group, a C 2-9 alkenyl group, a cycloalkyl group, an aryl group, or an aralkyl group, wherein one or more carbon atoms of these groups may be replaced by at least one atom selected from the group consisting of an oxygen atom and a nitrogen atom;
R 2 is the same or different, and is a C 1-18 alkylene group, wherein one or more carbon atoms of this group other than a carbon atom directly bonded to a silicon atom may be replaced by at least one atom selected from the group consisting of an oxygen atom and a nitrogen atom;
R 3 is the same or different, and is a C 1-18 alkyl group, a C 2-9 alkenyl group, a cycloalkyl group, an aryl group, or an aralkyl group, wherein one or more carbon atoms of these groups may be replaced by at least one atom selected from the group consisting of an oxygen atom and a nitrogen atom; and
n is the same or different, and is an integer of 0 to 3, and
wherein the curing accelerator is a tertiary amine compound or an imidazole compound.

2. The method according to claim 1 , wherein the curing accelerator is an imidazole compound.

3. The method according to claim 1 , wherein the curing accelerator is a tertiary amine compound.

4. The method according to claim 1 , wherein the epoxy resin is represented by the formula (1a):

wherein X is a divalent group obtained by removing two hydrogen atoms from a hydrocarbon ring, or a divalent group represented by the formula (2a):

wherein Y is a bond, a C 1-6 alkylene group, an oxygen atom (—O—), or a group represented by the formula: —S(O) m — wherein m is 0, 1, or 2;
R 1 is the same or different, and is a C 1-18 alkyl group, a C 2-9 alkenyl group, a cycloalkyl group, an aryl group, or an aralkyl group, wherein one or more carbon atoms of these groups may be replaced by at least one atom selected from the group consisting of an oxygen atom and a nitrogen atom;
R 2 is the same or different, and is a C 1-18 alkylene group, wherein one or more carbon atoms of this group other than a carbon atom directly bonded to a silicon atom may be replaced by at least one atom selected from the group consisting of an oxygen atom and a nitrogen atom;
R 3 is the same or different, and is a C 1-18 alkyl group, a C 2-9 alkenyl group, a cycloalkyl group, an aryl group, or an aralkyl group, wherein one or more carbon atoms of these groups may be replaced by at least one atom selected from the group consisting of an oxygen atom and a nitrogen atom; and
n is the same or different, and is an integer of 0 to 3.

5. The method according to claim 1 , wherein the epoxy resin is represented by the formula (1a):

wherein all R 1 are C 1-3 alkyl groups, both n are 0, both R 2 are dimethylene groups, and X is a 1,4-phenylene group.

6. The method according to claim 1 , wherein the acid anhydride-based curing agent is at least one member selected from the group consisting of cyclic aliphatic acid anhydrides, aromatic acid anhydrides, and aliphatic acid anhydrides.

7. The method according to claim 1 , wherein the acid anhydride-based curing agent is at least one member selected from the group consisting of hexahydrophthalic anhydride, 3-methylhexahydrophthalic anhydride, 4-methylhexahydrophthalic anhydride, 1-methylnorbornane-2,3-dicarboxylic anhydride, 5-methylnorbornane-2,3-di carboxylic anhydride, norbornane-2,3-dicarboxylic anhydride, 1-methylnadic anhydride, 5-methylnadic anhydride, nadic anhydride, phthalic anhydride, tetrahydrophthalic anhydride, 3-methyltetrahydrophthalic anhydride, 4-methyltetrahydrophthalic anhydride, and dodecenylsuccinic anhydride.

8. The method according to claim 1 , wherein the metal is copper or aluminum.

Assignees

• Sumitomo Seika Chemicals

Inventors

• Fukuda Noriaki
• Harisaki Ryota
• Yamamoto Katsumasa
• Nemoto Nobukatsu

Classifications

• H10W74/47

  comprising organic materials, e.g. plastics or resins · CPC title

• H10W74/10

  characterised by their shape or disposition · CPC title

• C08G59/306 Primary

  containing silicon · CPC title

• C08G59/4215

  cycloaliphatic · CPC title

• C09K3/1018

  Macromolecular compounds having one or more carbon-to-silicon linkages · CPC title