Curing accelerator and radical polymerizable resin composition

Patent metadata

Field	Value
Publication number	US-10975227-B2
Application number	US-201716341151-A
Country	US
Kind code	B2
Filing date	Sep 4, 2017
Priority date	Oct 26, 2016
Publication date	Apr 13, 2021
Grant date	Apr 13, 2021

Abstract

A curing accelerator can exhibit good curing acceleration performance and is excellent in storage stability, while maintaining sufficient pot life in a curing reaction of radical-polymerizable resins, and a radical-polymerizable resin composition uses the curing accelerator. The curing accelerator for radical-polymerizable resins includes a metal-containing compound (A), a thiol compound (B) and an aprotic solvent (C) having a dielectric constant of 10 or less, wherein the metal-containing compound (A) is one or more compounds selected from a metal soap (A1) and a β-diketone skeleton-having metal complex (A2), the thiol compound (B) is one or more compounds selected from a mono-functional primary thiol compound (B1), a secondary thiol compound (B2) and a tertiary thiol compound (B3), and the content of the aprotic solvent (C) is 10 to 1,000 parts by mass relative to 100 parts by mass of the total of the metal-containing compound (A) and the thiol compound (B).

First claim

The invention claimed is:

1. A curing accelerator for radical-polymerizable resins, comprising a metal-containing compound (A), a thiol compound (B) and an aprotic solvent (C),
wherein the metal-containing compound (A) is one or more compounds selected from the group consisting of a metal soap (A1) and a β-diketone skeleton-having metal complex (A2),
a metal element to constitute the metal-containing compound (A) is at least one selected from the group consisting of iron, cobalt, manganese, titanium and zirconium,
the thiol compound (B) is one or more compounds selected from the group consisting of a mono-functional primary thiol compound (B1), a secondary thiol compound (B2) and a tertiary thiol compound (B3),
the thiol compound (B) has an ester structure represented by the following general formula (Q-1):

Wherein R 1 and R 2 each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aromatic group having 6 to 18 carbon atoms; * bonds to an organic group; and a represents an integer of 0 to 2, and
the content of the aprotic solvent (C) is from 10 to 1,000 parts by mass relative to 100 parts by mass of the total of the metal-containing compound (A) and the thiol compound (B).

2. The curing accelerator according to claim 1 , wherein the thiol compound (B) is one or more selected from the group consisting of a secondary thiol compound (B2) and a tertiary thiol compound (B3), and is an ester compound of a mercapto group-containing carboxylic acid represented by the following general formula (S) and a polyhydric alcohol:

wherein R 3 represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aromatic group having 6 to 18 carbon atoms; R 4 represents an alkyl group having 1 to 10 carbon atoms, or an aromatic group having 6 to 18 carbon atoms; and a represents an integer of 0 to 2.

3. The curing accelerator according to claim 1 , wherein the aprotic solvent (C) is one or more compounds selected from the group consisting of an aliphatic hydrocarbon, an aromatic hydrocarbon, an ether, a ketone, an ester and a chain carbonate.

4. The curing accelerator according to claim 1 , wherein the content of the thiol compound (B) is from 0.01 to 15 mol relative to 1 mol of the metal component of the metal-containing compound (A).

5. A radical-polymerizable resin composition comprising the curing accelerator of claim 1 , and a radical-polymerizable compound (D).

6. The radical-polymerizable resin composition according to claim 5 , further comprising a radical polymerization initiator (E).

Assignees

• Show A Denko K K
• Showa Denko Kk

Inventors

• Sakaguchi Yoichiro
• Minami Takuya
• Okuno Yoshishige
• Umino Atsushi
• Ishibashi Yoshitaka

Classifications

• C08K5/0091 Primary

  Complexes with metal-heteroatom-bonds · CPC title

• C08K5/548 Primary

  containing sulfur {(C08K5/5477 takes precedence)} · CPC title

• C08F2/38

  Polymerisation using regulators, e.g. chain terminating agents {, e.g. telomerisation} · CPC title

• C08K5/098

  Metal salts of carboxylic acids · CPC title

• C08F20/00

  Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof · CPC title