Highly sensitive (meth)acrylate and radical curable material

Patent metadata

Field	Value
Publication number	US-9708432-B2
Application number	US-201314766384-A
Country	US
Kind code	B2
Filing date	Aug 9, 2013
Priority date	Feb 25, 2013
Publication date	Jul 18, 2017
Grant date	Jul 18, 2017

Abstract

Provided is a (meth)acrylate and a radical curable material with which the sensitivity can be enhanced to improve the curability, the increase in viscosity can be suppressed due to good compatibility with various acrylate compounds, and there is no risk that the physical properties of the curable material are deteriorated. The (meth)acrylate has one or more structures represented by Formula 1 in the molecule, and when the (meth)acrylate is used for radical curing, the sensitivity is enhanced. In Formula 1, R 1 is a hydrogen atom or a methyl group, R 2 is a C 1 -C 10 alkyl chain, R 3 is either Formula 2 or 3, and R 4 is an alkyl chain constituted by carbon atoms and hydrogen atoms.

First claim

The invention claimed is:

1. A radical curable material comprising:
a (meth)acrylate consisting of a structure represented by Formula 1:

where R 1 is a hydrogen atom or a methyl group, R 2 is a C 1 -C 10 alkylene group, R 3 is either Formula 2:

or Formula 3:

and R 4 is an alkyl chain constituted by carbon atoms and hydrogen atoms,
the (meth)acrylate being obtained by directly reacting a hydroxyl group of a (meth)acrylate having a hydroxyl group or an amino group of a (meth)acrylate having an amino group with an isocyanate group of a monoisocyanate compound; and
at least one metal-containing compound selected from the group consisting of bis(2,4-pentanedionato)tin, dibutyltin bis(trifluoromethanesulfonate), dibutyltin diacetate, dibutyltin maleate, phthalocyanine tin(IV) dichloride, tetrabutylammonium difluoro triphenyltin, phthalocyanine tin(II), tributyl(2-pyridyl)tin, tributyl(2-thienyl)tin, tributyltin acetate, tributyl(trimethylsilylethynyl)tin, trimethyl (2-pyridyl)tin, bis(hexafluoroacetylacetonato)copper(II), bis(2,4-pentanedionato)copper(II), bis(1,3-propanediamine)copper(II)dichloride, bis(8-quinolinolato)copper(II), bis(trifluoro-2,4-pentanedionato)copper(II), copper(II) bis(2-hydroxyethyl) dithiocarbamate, copper diethyldithiocarbamate, copper (II) dimethyldithiocarbamate, copper(II) disodium ethylenediaminetetraacetate, phthalocyanine copper(II), dichloro(1,10-phenanthroline) copper(II), phthalocyanine copper, tetra-4-tert-butylphthalocyanine copper, tetrakis(acetonitrile)copper(I) hexafluorophosphate, bis[2-(2-benzothiazolyl)phenolate]zinc(II), bis[2-(2-benzoxazolyl)phenolate]zinc(II), bis(2-hydroxyethyl)zinc(II) dithiocarbamate, bis(2,4-pentanedionato)zinc(II), bis(8-quinolinolato)zinc(II), bis(tetrabutylammonium)bis(1,3-dithiol-2-thione-4,5-dithiolato) zinc complex, zinc disodium ethylenediaminetetraacetate, zinc(II) dibenzyl dithiocarbamate, zinc (II) dibutyl dithiocarbamate, zinc diethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc phthalocyanine, bis(cyclopentadienyl)cobalt(III)hexafluorophosphate, [1,1′-bis(diphenylphosphino)ferrocene]cobalt(II)dichloride, bis(hexafluoroacetylacetonato)cobalt(II), (1R,2R)—N,N-bis[3-oxo-2-(2,4,6-trimethylbenzoyl)butylidene]-1,2-diphenylethylenediaminato cobalt(II), (1S,2S)—N,N′-bis[3-oxo-2-(2,4,6-trimethylbenzoyl)butylidene]-1,2-diphenylethylenediaminato cobalt(II), bis(2,4-pentanedionato)cobalt(II), bis(trifluoro-2,4-pentanedionato)cobalt(II), phthalocyanine cobalt(II), cobalt disodium ethylenediaminetetraacetate, hexaamminecobalt(III) chloride, N,N′-disalicylalethylenediamine cobalt(II), [5,10,15,20-tetrakis(4-methoxyphenyl)porphyrinato]cobalt(II), tris(2,4-pentanedionato)cobalt(III), [1,2-bis(diphenylphosphino)ethane]nickel(II)dichloride, bis(dithiobenzyl)nickel(II), bis(hexafluoroacetylacetonato)nickel(II), bis(2,4-pentanedionato)nickel(II), bis(tetrabutylammonium)bis(maleonitriledithiolato)nickel(II) complex, bis(tricyclohexylphosphine)nickel(II) dichloride, bis(triphenylphosphine)nickel(II) dichloride, bromo[(2,6-pyridinediyl)bis(3-methyl-1-imidazolyl-2-ylidene)]nickel bromide, nickel(II) disodium ethylenediaminetetraacetate, nickel(II) dibutyldithiocarbamate, and nickel diethyldithiocarbamate.

2. A radical curable material comprising:
a (meth)acrylate consisting of a structure represented by Formula 17:

where R 1 is a hydrogen atom or a methyl group, R 2 is a C 1 -C 10 alkylene group, R 3 is either Formula 2:

or Formula 3:

and R 4 is an alkylene chain constituted by carbon atoms and hydrogen atoms,
the (meth)acrylate being obtained by directly reacting a hydroxyl group of a (meth)acrylate having a hydroxyl group or an amino group of a (meth)acrylate having an amino group with an isocyanate group of a diisocyanate compound; and
at least one metal-containing compound selected from the group consisting of bis(2,4-pentanedionato)tin, dibutyltin bis(trifluoromethanesulfonate), dibutyltin diacetate, dibutyltin maleate, phthalocyanine tin(IV) dichloride, tetrabutylammonium difluoro triphenyltin, phthalocyanine tin(II), tributyl(2-pyridyl)tin, tributyl(2-thienyl)tin, tributyltin acetate, tributyl(trimethylsilylethynyl)tin, trimethyl (2-pyridyl)tin, bis(hexafluoroacetylacetonato)copper(II), bis(2,4-pentanedionato)copper(II), bis(1,3-propanediamine)copper(II)dichloride, bis(8-quinolinolato)copper(II), bis(trifluoro-2,4-pentanedionato)copper(II), copper(II) bis(2-hydroxyethyl) dithiocarbamate, copper diethyldithiocarbamate, copper (II) dimethyldithiocarbamate, copper(II) disodium ethylenediaminetetraacetate, phthalocyanine copper(II), dichloro(1,10-phenanthroline) copper(II), phthalocyanine copper, tetra-4-tert-butylphthalocyanine copper, tetrakis(acetonitrile)copper(I) hexafluorophosphate, bis[2-(2-benzothiazolyl)phenolate]zinc(II), bis[2-(2-benzoxazolyl)phenolate]zinc(11), bis(2-hydroxyethyl)zinc(II) dithiocarbamate, bis(2,4-pentanedionato)zinc(II), bis(8-quinolinolato)zinc(II), bis(tetrabutylammonium)bis(1,3-dithiol-2-thione-4,5-dithiolato) zinc complex, zinc disodium ethylenediaminetetraacetate, zinc(II) dibenzyl dithiocarbamate, zinc (II) dibutyl dithiocarbamate, zinc diethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc phthalocyanine, bis(cyclopentadienyl)cobalt(III)hexafluorophosphate, [1,1′-bis(diphenylphosphino)ferrocene]cobalt(II)dichloride, bis(hexafluoroacetylacetonato)cobalt(II), (1R,2R)—N,N′-bis[3-oxo-2-(2,4,6-trimethylbenzoyl)butylidene]-1,2-diphenylethylenediaminato cobalt(II), (1S,2S)—N,N′-bis[3-oxo-2-(2,4,6-trimethylbenzoyl)butylidene]-1,2-diphenylethylenediaminato cobalt(II), bis(2,4-pentanedionato)cobalt(II), bis(trifluoro-2,4-pentanedionato)cobalt(II), phthalocyanine cobalt(II), cobalt disodium ethylenediaminetetraacetate, hexaamminecobalt(III) chloride, N,N′-disalicylalethylenediamine cobalt(II), [5,10,15,20-tetrakis(4-methoxyphenyl)porphyrinato]cobalt(II), tris(2,4-pentanedionato)cobalt(III), [1,2-bis(diphenylphosphino)ethane]nickel(II)dichloride, bis(dithiobenzyl)nickel(II), bis(hexafluoroacetylacetonato)nickel(II), bis(2,4-pentanedionato)nickel(II), bis(tetrabutylammonium)bis(maleonitriledithiolato)nickel(II) complex, bis(tricyclohexylphosphine)nickel(II) dichloride, bis(triphenylphosphine)nickel(II) dichloride, bromo[(2,6-pyridinediyl)bis(3-methyl-1-imidazolyl-2-ylidene)]nickel bromide, nickel(II) disodium ethylenediaminetetraacetate, nickel(II) dibutyldithiocarbamate, and nickel diethyldithiocarbamate.

3. The radical curable material according to claim 1 ,
wherein a molar content of the structure represented by Formula 2 or 3 (mole of functional group•bonding group per mass of (meth)acrylate) in the (meth)acrylate is 0.001 mol/g or more.

4. The radical curable material according to claim 1 , comprising the metal-containing compound in an amount of 0.0005 mass % or more of the entire curable material.

5. The radical curable material according to claim 1 , further comprising a photopolymerization initiator.

6. The radical curable material according to claim 1 , further comprising a heat polymerization initiator.

7. The radical curable material according to claim 1 ,
wherein R 4 in Formula 1 is one of a C 1 -C 18 linear alkyl group, br

Assignees

• Autonetworks Technologies Ltd
• Sumitomo Wiring Systems
• Sumitomo Electric Industries
• Univ Kyushu
• Sumitomo Wiring Systems

Inventors

• Hase Tatsuya
• Nakashima Kazuo
• Mizoguchi Makoto

Classifications

• C08L33/14

  of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen · CPC title

• C08F220/20

  of polyhydric alcohols or phenols {, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate} · CPC title

• C09J4/00

  Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16} · CPC title

• C09D4/00

  Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16} · CPC title

• C08L33/06

  of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical · CPC title