Curable composition, cured product, and method of producing cured product

Patent metadata

Field	Value
Publication number	US-12110360-B2
Application number	US-201917270974-A
Country	US
Kind code	B2
Filing date	Aug 27, 2019
Priority date	Aug 28, 2018
Publication date	Oct 8, 2024
Grant date	Oct 8, 2024

Abstract

One embodiment of the present invention provides a curable composition, including a polyfunctional isocyanate compound, a compound selected from the group consisting of a multivalent alcohol and an epoxy compound, and a base amplifier.

First claim

What is claimed is:

1. A curable composition, comprising:
a polyfunctional isocyanate compound;
a compound selected from the group consisting of a multivalent alcohol and an epoxy compound;
a base amplifier; and
a base generator,
wherein a content of the base amplifier in the curable composition is from 3% by mass to 15% by mass with respect to a total amount of the multivalent alcohol and the epoxy compound.

2. The curable composition according to claim 1 , wherein the base amplifier comprises a compound represented by the following General Formula (1):

wherein, in the formula, G represents an organic group; and X is a group represented by the following General Formula (1)-11, General Formula (1)-12, General Formula (1)-13, or General Formula (1)-14:

wherein, in the formulae, each of R 11 , R 12 , R 13 , R 21 , R 22 , R 23 , R 24 , R 31 , R 32 , R 33 , R 41 , R 42 , R 43 , and R 44 independently represents a hydrogen atom or a hydrocarbon group; when two or more of R 11 , R 12 , or R 13 are hydrocarbon groups, the two or more hydrocarbon groups may be bonded to each other to form a ring; when two or more of R 21 , R 22 , R 23 , or R 24 are hydrocarbon groups, the two or more hydrocarbon groups may be bonded to each other to form a ring; when two or more of R 31 , R 32 , or R 33 are hydrocarbon groups, the two or more hydrocarbon groups may be bonded to each other to form a ring; when two or more of R 41 , R 42 , R 43 , or R 44 are hydrocarbon groups, the two or more hydrocarbon groups may be bonded to each other to form a ring; and * represents a site that is bonded to a carbon atom.

3. The curable composition according to claim 2 , wherein the compound represented by General Formula (1) comprises at least one compound selected from the group consisting of a compound represented by the following General Formula (1)-A and a compound represented by the following General Formula (1)-B:

wherein, in the formulae, R 1 represents an organic group; each of R 2 and R 3 independently represents a hydrogen atom or an organic group; each X independently represents the group represented by General Formula (1)-11, General Formula (1)-12, General Formula (1)-13, or General Formula (1)-14; at least one of R 2 or R 3 represents an organic group; and when R 2 and R 3 are both organic groups, they may be bonded to each other to form a ring.

4. The curable composition according to claim 1 , wherein the base generator is a compound that generates a base in response to irradiation by light or heating.

5. A cured product obtained by curing the curable composition according to claim 1 .

6. The cured product according to claim 5 , having a thickness of 1×10 −3 m or more.

7. A method of producing a cured product, the method comprising:
forming a urethane bond using, as a catalyst, a base that is generated by applying energy to the curable composition according to claim 1 .

8. A method of producing a cured product, the method comprising:
applying energy to the curable composition according to claim 1 , to generate a base from the base generator and to generate a base from the base amplifier;
wherein a part of the generated base activates a hydroxyl group of the multivalent alcohol or an epoxy group of the epoxy compound, to promote generation of a base from the base amplifier, and another part of the generated base, as a catalyst, initiates or promotes a urethane bond formation reaction of the polyvalent isocyanate compound and the multivalent alcohol, to produce a polyurethane that is a reacted cured product.

9. The method of producing a cured product according to claim 7 , wherein the application of energy is at least one of irradiation by light or heating.

10. The method of producing a cured product according to claim 7 , wherein the curable composition is a film having a thickness of 1×10 −3 or more.

Assignees

• Univ Tokyo Science Found

Inventors

• Arimitsu Koji

Classifications

• C08J2375/04

  Polyurethanes · CPC title

• C08J5/18

  Manufacture of films or sheets · CPC title

• C08G18/7642 Primary

  containing at least two isocyanate or isothiocyanate groups linked to the aromatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate groups, e.g. xylylene diisocyanate or homologues substituted on the aromatic ring · CPC title

• C08G18/584

  having nitrogen · CPC title

• C08G18/581

  Reaction products of epoxy resins with less than equivalent amounts of compounds containing active hydrogen added before or during the reaction with the isocyanate component (with amines C08G18/584) · CPC title