Curable resin composition, cured product thereof, and bonded body bonded by cured product

Patent metadata

Field	Value
Publication number	US-11155669-B2
Application number	US-201716330894-A
Country	US
Kind code	B2
Filing date	Sep 5, 2017
Priority date	Sep 27, 2016
Publication date	Oct 26, 2021
Grant date	Oct 26, 2021

Abstract

A manner for improving storage stability of a curable resin composition and close adhesion of a cured product to a polycarbonate. The present description relates to a curable resin composition including the following components (A) to (C): component (A): an isocyanate group-containing urethane prepolymer, component (B): a powder of a polyamine compound which is solid at 25° C., and component (C): at least one selected from the group consisting of a monofunctional (meth)acrylate compound having an alicyclic structure or a monofunctional (meth)acrylate compound having an aromatic ring, a monofunctional (meth)acrylate compound having a hydrolyzable silyl group, and a polyfunctional (meth)acrylate compound, where the composition does not substantially include a photoradical initiator.

First claim

The invention claimed is:

1. A curable resin composition comprising the following:
component (A): an isocyanate group-containing urethane prepolymer,
component (B): a powder of a polyamine compound which is solid at 25° C., and
component (C): at least one selected from the group consisting of a monofunctional (meth)acrylate compound having an alicyclic structure, a monofunctional (meth)acrylate compound having an aromatic ring, a monofunctional (meth)acrylate compound having a hydrolyzable silyl group, and a polyfunctional (meth)acrylate compound,
wherein the composition does not substantially comprise a photoradical initiator, wherein a content of a photoradical initiator is less than 1% by mass based on the total mass of the curable resin composition,
wherein the monofunctional (meth)acrylate compound having an alicyclic structure is at least one selected from the group consisting of cyclohexyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentenyloxy (meth)acrylate, isobornyl (meth)acrylate, and adamantyl (meth)acrylate,
wherein the monofunctional (meth)acrylate compound having an aromatic ring is at least one selected from the group consisting of phenoxyethyl (meth)acrylate, benzyl (meth)acrylate, phenyl (meth)acrylate, phenoxydiethyleneglycol (meth)acrylate, phenoxytetraethyleneglycol (meth)acrylate, and nonylphenoxyethyl (meth)acrylate,
wherein the monofunctional (meth)acrylate compound having a hydrolyzable silyl group is at least one selected from the group consisting of 3-(meth)acryloxypropyltrimethoxysilane, 3-(meth) acryloxypropyltriethoxysilane, 3-(meth)acryloxypropylmethyldimethoxysilane, and 3-(meth)acryloxypropylmethyldiethoxysilane, and
wherein the polyfunctional (meth)acrylate compound is at least one selected from the group consisting of 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, 1, 10-decanediol di(meth)acrylate, dipropyleneglycol di(meth)acrylate, tripropyleneglycol di(meth)acrylate, polypropyleneglycol di(meth)acrylate, neopentylglycol di(meth)acrylate, polytetramethyleneglycol di(meth)acrylate, neopentylglycoladipate di(meth)acrylate, hydroxypivalic acid neopentylglycol di(meth)acrylate, dicyclopentanyl di(meth)acrylate, dimethyloltricyclodecane di(meth)acrylate, caprolactone modified dicyclopentenyl di(meth)acrylate, ethyleneoxide modified phosphoric acid di(meth)acrylate, isocyanurate di(meth)acrylate, allylated cyclohexyldi(meth)acrylate, isocyanuric acid ethylene oxide modified di(meth)acrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol tri(meth)acrylate, propionic acid modified dipentaerythritol tri(meth)acrylate, trimethylolpropane triacrylate, ethyleneoxide modified trimethylolpropane tri(meth)acrylate, propyleneoxide modified trimethylolpropane tri(meth)acrylate, tris(acryloxyethyl)isocyanurate, isocyanuric acid ethylene oxide modified tri(meth)acrylate, pentaerythritoltetra(meth)acrylate, ditrimethylolpropanetetra(meth)acrylate, dipentaerythritolpenta(meth)acrylate, propionic acid modified dipentaerythritolpenta(meth)acrylate, dipentaerythritolhexa(meth)acrylate, caprolactone modified dipentaerythritolhexa(meth)acrylate, dipentaerythritolpenta(meth)acrylate, propionic acid modified dipentaerythritolpenta(meth)acrylate, dipentaerythritolhexa(meth)acrylate, and caprolactone modified dipentaerythritolhexa(meth)acrylate.

2. The curable resin composition according to claim 1 , wherein the component (A) is a reaction product of a polyol compound (a-1) and a polyisocyanate compound (a-2).

3. The curable resin composition according to claim 1 , wherein the component (B) has an average particle diameter of 0.1 to 100 μm.

4. The curable resin composition according to claim 1 , wherein the component (B) is at least one compound selected from the group consisting of an aliphatic polyamine compound, an alicyclic polyamine compound, an aromatic polyamine compound, and a hydrazide compound.

5. The curable resin composition according to claim 1 , wherein the component (B) is comprised at 0.1 to 100 parts by mass, based on 100 parts by mass of the component (A).

6. The curable resin composition according to claim 1 , wherein the polyfunctional (meth)acrylate compound is at least one selected from the group consisting of isocyanuric acid ethylene oxide modified di(meth)acrylate, trimethylolpropane triacrylate, and isocyanuric acid ethylene oxide modified tri(meth)acrylate.

7. The curable resin composition according to claim 1 , further comprising a compound having a glycidyl group as a component (D).

8. The curable resin composition according to claim 7 , wherein the compound having a glycidyl group is a compound having an alkoxysilyl group and a glycidyl group in the molecule.

9. The curable resin composition according to claim 7 , wherein the compound having a glycidyl group is at least one compound selected from the group consisting of 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, and 3-glycidoxypropyltriethoxysilane.

10. The curable resin composition according to claim 7 , wherein a combining amount of the component (D) is 0.1 to 10 parts by mass based on 100 parts by mass of the component (A).

11. A cured product of the curable resin composition according to claim 1 .

12. A bonded body wherein a first adherend, the cured product according to claim 11 , and a second adherend are laminated in this order, such that a surface of the first adherend and a surface of the cured product are adhered to each other, and a surface of the second adherend and a surface of the cured product are adhered to each other.

Assignees

• Three Bond Co Ltd

Inventors

• Watanabe Kentaro

Classifications

• C09J183/14

  in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms (C09J183/10 takes precedence) · CPC title

• B32B2457/00

  Electrical equipment · CPC title

• B32B17/06

  comprising glass as the main or only constituent of a layer, next to another layer of a specific {material} · CPC title

• B32B27/365

  comprising polycarbonates · CPC title

• B32B2457/10

  Batteries · CPC title