Curable resin composition

Patent metadata

Field	Value
Publication number	US-2022185946-A1
Application number	US-202017436498-A
Country	US
Kind code	A1
Filing date	Mar 27, 2020
Priority date	Mar 27, 2019
Publication date	Jun 16, 2022
Grant date	—

Abstract

Disclosed is a curable resin composition that has excellent curability by irradiation of light and heating and that is suitable for such applications as liquid encapsulants, liquid adhesives, adhesives for camera modules, and liquid crystal sealants. The curable resin composition contains (A) an aromatic epoxy resin having an allyl group, (B) a thiol-based curing agent, (C) a photoradical initiator, and (D) a thermally latent curing agent. Preferably, (A) the compound having an allyl group and an epoxy group is an aromatic epoxy resin having an allyl group. Preferably, the thiol-based curing agent, which is component (B), is in liquid form at 25° C.

First claim

1 . A curable resin composition comprising:
(A) a compound having an allyl group and an epoxy group; (B) a thiol-based curing agent; (C) a photoradical initiator; and (D) at least one type of compound selected from the group consisting of thermally latent curing agents and curing catalysts.

2 . The curable resin composition according to claim 1 , wherein (A) the compound having an allyl group and an epoxy group is an aromatic epoxy resin having an allyl group.

3 . The curable resin composition according to claim 2 , wherein the aromatic epoxy resin having an allyl group contains a benzene ring, and the allyl group is located at an ortho position with respect to the epoxy group.

4 . The curable resin composition according to claim 2 , wherein the aromatic epoxy resin having an allyl group is a compound represented by formula (1) below:

(wherein m represents 0 or a positive number, Y represents —S— or an unsubstituted or fluorine-substituted divalent hydrocarbon group, and R 1 , R 2 , R 3 , and R 4 each independently represent a hydrogen atom, a C 1-4 alkyl group, an allyl group, or a glycidyloxy group).

5 . The curable resin composition according to claim 4 , wherein Y in the formula (1) is at least one selected from the group consisting of formulas (Y-1) to (Y-9) below:

(wherein n represents an integer from 4 to 12, R 5 , R 6 , R 7 , and R 8 each independently represent a hydrogen atom or an unsubstituted or fluorine-substituted methyl group, and * represents a bonding site).

6 . The curable resin composition according to claim 1 , wherein the thiol-based curing agent which is the component (B) is in liquid form at 25° C.

7 . The curable resin composition according to claim 1 , wherein the thiol-based curing agent which is the component (B) is a polythiol compound.

8 . The curable resin composition according to claim 7 , wherein the polythiol compound is a polythiol ether of a polyol, or a polythiol having a heterocycle containing at least one nitrogen in a ring thereof.

9 . The curable resin composition according to claim 1 , comprising, per 1 equivalent of the allyl group in the component (A), from 0.5 to 1.5 equivalents of the thiol-based curing agent which is the component (B).

10 . The curable resin composition according to claim 1 , wherein the photoradical initiator which is the component (C) is at least one type of compound selected from the group consisting of acetophenone-based compounds, benzil-based compounds, benzophenone-based compounds, thioxanthone-based compounds, and oxime ester-based compounds.

11 . The curable resin composition according to claim 10 , wherein the component (C) is an aminoacetophenone-based compound.

12 . The curable resin composition according to claim 1 , wherein the component (D) is a modified amine-based curing agent.

13 . The curable resin composition according to claim 12 , wherein the modified amine-based curing agent is a polyepoxy and/or isocyanate adduct of an amine compound containing at least one active hydrogen.

14 . A method for curing a curable resin composition, comprising:
a step of pre-curing the curable resin composition according to claim 1 by irradiating the curable resin composition with light; and a step of curing the pre-cured curable resin composition by heating the pre-cured curable resin composition.

15 . A cured product obtained by first pre-curing the curable resin composition according to claim 1 by light, and then curing the pre-cured curable resin composition by heat.

16 . The curable resin composition according to claim 3 , wherein the aromatic epoxy resin having an allyl group is a compound represented by formula (1) below:

(wherein m represents 0 or a positive number, Y represents —S— or an unsubstituted or fluorine-substituted divalent hydrocarbon group, and R 1 , R 2 , R 3 , and R 4 each independently represent a hydrogen atom, a C 1-4 alkyl group, an allyl group, or a glycidyloxy group).

17 . The curable resin composition according to claim 2 , wherein the thiol-based curing agent which is the component (B) is in liquid form at 25° C.

18 . The curable resin composition according to claim 3 , wherein the thiol-based curing agent which is the component (B) is in liquid form at 25° C.

19 . The curable resin composition according to claim 4 , wherein the thiol-based curing agent which is the component (B) is in liquid form at 25° C.

20 . The curable resin composition according to claim 5 , wherein the thiol-based curing agent which is the component (B) is in liquid form at 25° C.

Assignees

• Adeka Corp

Inventors

• Kobayashi Shota
• Tamaso Ken-Ichi
• Ogawa Ryo
• Nagamatsu Tamotsu

Classifications

• C09J163/00

  Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins · CPC title

• C08G59/68

  characterised by the catalysts used · CPC title

• C08G59/66

  Mercaptans · CPC title

• C08G59/56

  together with other curing agents · CPC title

• C08G2170/00

  Compositions for adhesives · CPC title