Latent additive and composition containing latent additive

Patent metadata

Field	Value
Publication number	US-9777138-B2
Application number	US-201314405159-A
Country	US
Kind code	B2
Filing date	Jun 21, 2013
Priority date	Jul 31, 2012
Publication date	Oct 3, 2017
Grant date	Oct 3, 2017

Abstract

A latent additive which is represented by general formula (1). (In the formula, A represents a five-membered or six-membered aromatic ring or heterocyclic ring; each of R 1 and R 2 independently represents a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an optionally substituted alkyl group having 1-40 carbon atoms, an aryl group having 6-20 carbon atoms, an arylalkyl group having 7-20 carbon atoms or a heterocyclic ring-containing group having 2-20 carbon atoms; and R 4 represents an alkyl group having 1-20 carbon atoms, an alkenyl group having 2-20 carbon atoms, an aryl group having 6-20 carbon atoms, an arylalkyl group having 7-20 carbon atoms, a heterocyclic ring-containing group having 2-20 carbon atoms or a trialkylsilyl group.)

First claim

The invention claimed is:

1. A composition comprising
a latent additive represented by formula (1):

wherein A represents a benzene ring;
R 1 represents a C4-C6 alkyl group;
R 2 represents a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an optionally substituted C1-C40 alkyl group, a C6-C20 aryl group, a C7-C20 arylalkyl group, or a C2-C20 heterocyclic ring-containing group;
R 4 represents a C2-C9 alkoxycarbonyl group;
R 1 is adjacent to —(O—R 4 ) k ;
the methylene moiety of the alkyl or arylalkyl group represented by R 1 , and R 2 may be replaced by a combination of one or more groups selected from a carbon-carbon double bond, —S—, —O—CO—, —CO—O—, —O—CO—O—, —O—CO—O—, —S—CO—, —CO—S—, —S—CO—O—, —O—CO—S—, —CO—NH—, —NH—CO—, —NH—CO—O—, —NR′—, >P═O, —S—S—, and —SO 2 —;
the methylene moiety of the alkyl or arylalkyl group represented by R 4 may be replaced by a combination of one or more groups selected from a carbon-carbon double bond, —O—, —S—, —CO—, —O—CO—, —CO—O—, —O—CO—O—, —O—CO—O—, —S—CO—, —CO—S—, —S—CO—O—, —O—CO—S—, —CO—NH—, —NH—CO—, —NH—CO—O—, —NR′—, >P═O, —S—S—, and —SO 2 —;
R′ represents a hydrogen atom or a C1-C8 alkyl group;
a plurality of R 2 's may be taken together to form a benzene ring or a naphthalene ring;
a plurality of R 2 's may be the same or different; a plurality of R 4 's may be the same or different;
n represents an integer of 1 to 10;
d represents an integer of 1 to 3;
k represents an integer of 1 to 3; and
X represents a single bond, a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, a group represented by

 >P═O, >C═O, >NR 10 , >PR 10 , —OR 10 ,—SR 10 , —NR 10 R 11 , —PR 10 R 11 , a C1-C120 aliphatic hydrocarbon group, a C6-C35 aromatic ring-containing hydrocarbon group, or a C2-C35 heterocyclic ring-containing group, the aliphatic hydrocarbon group, aromatic ring-containing hydrocarbon group, and heterocyclic ring-containing group having as many valences as n and optionally having a substituent;
R 10 and R 11 each represent a hydrogen atom, an optionally substituted C1-C35 aliphatic hydrocarbon group, an optionally substituted C6-C35 aromatic ring-containing hydrocarbon group, or an optionally substituted C2-C35 heterocyclic ring-containing group, the aliphatic hydrocarbon group, aromatic ring-containing group, and heterocyclic ring-containing group being optionally substituted by a combination of one or more groups selected from a carbon-carbon double bond, —O—, —S—, —CO—, —O—CO—, —CO—O—, —O—CO—O—, —O—CO—O—, —S—CO—, —CO—S—, —S—CO—O—, —O—CO—S—, —CO—NH—, —NH—CO—, —NH—CO—O—, —NR′—, >P═O, —S—S—, —SO 2 —, and a nitrogen atom;
the aromatic or heterocyclic ring may be fused to one or more additional rings;
when X is a nitrogen atom, a phosphorous atom, or the group represented by

 n is 3;
when X is an oxygen atom or a sulfur atom, n is 2;
when X is >C═O, —NH—CO—, —CO—NH—, >NR 10 , or >PR 10 , n is 2; and when X is —OR 10 , —SR 10 , —NR 10 R 11 , or —PR 10 R 11 , n is 1; and
X may be taken together with A to form a ring,

a radical polymerizable organic substance, and
a photo-radical polymerization initiator or a thermal radical polymerization initiator.

2. A compound represented by formula (2):

wherein
A represents a benzene ring;
R 201 represents a C4-C6 alkyl group;
R 202 represents a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an optionally substituted C1-C40 alkyl group, a C6-C20 aryl group, or a C7-C20 arylalkyl group;
d represents an integer of 1 to 3;
k represents an integer of 1 to 3;
R 204 represents a C2-C9 alkoxycarbonyl group;
R 201 is adjacent to —(O—R 204 ) k ;
the methylene moiety of the alkyl or arylalkyl group represented by R 201 and R 202 may be replaced by a combination of one or more groups selected from a carbon-carbon double bond, —S—, —O—CO—, —CO—O—, —O—CO—O—, —O—CO—O—, —S—CO—, —CO—S—, —O—CO—S—, —S—CO—O—, —CO—NH—, —NH—CO—, —NH—CO—O—, —NR′—, >P═O, —S—S—, and —SO 2 —;
the methylene moiety of the alkyl or arylalkyl group represented by R 204 may be replaced by a combination of one or more groups selected from a carbon-carbon double bond, —O—, —S—, —CO—, —O—CO—, —CO—O—, —O—CO—O—, —O—CO—O—, —S—CO—, —CO—S—, —O—CO—S—, —S—CO—O—, —CO—NH—, —NH—CO—, —NH—CO—O—, —NR′—, >P═O, —S—S—, and —SO 2 —;
R′ represents a hydrogen atom or a C1-C8 alkyl group;
a plurality of R 202 's may be taken together to form a benzene ring or a naphthalene ring;
a plurality of R 202 's may be the same or different;
a plurality of R 204 's may be the same or different;
X 2 represents an oxygen atom, a sulfur atom, a group represented by

 >C═O, —NH—CO—, —CO—NH—, >NR 12 , >PR 12 , a substituent represented by a group selected from formula (3), formula (4), or [Chem. 10] shown below;
R 12 represents a hydrogen atom, an optionally substituted C1-C35 aliphatic hydrocarbon group, an optionally substituted C6-C35 aromatic ring-containing hydrocarbon group, or an optionally substituted C2-C35 heterocyclic ring-containing group, the aliphatic hydrocarbon group, aromatic ring-containing hydrocarbon group, and heterocyclic ring-containing group being optionally substituted by a combination of one or more groups selected from a carbon-carbon double bond, —O—, —S—, —CO—, —O—CO—, —CO—O—, —O—CO—O—, —O—CO—O—, —S—CO—, —CO—S—, —O—CO—S—, —S—CO—O—, —CO—NH—, —NH—CO—, —NH—CO—O—, —NR′ 13 , >P═O, —S—S—, and —SO 2 —;
the aromatic or heterocyclic ring may be fused to one or more additional rings; and
X 2 may be taken together with A to form a ring;

wherein Y 1 and Y 5 each independently represent a single bond, a C1-C4 alkylene group;
Y 2 and Y 4 each independently represent an oxygen atom or —NR 13 —;
R 13 represents a hydrogen atom or a C1-C20 aliphatic hydrocarbon group;
Y 3 represents a single bond, —NR 16 —, a divalent C1-C35 aliphatic hydrocarbon group, a divalent C6-C35 aromatic ring-containing group, or a substituent represented by formula (5) below, the aliphatic hydrocarbon group and C6-C35 aromatic ring-containing hydrocarbon group being optionally substituted by —COO—, —O—, —OCO—, 13 NHCO—, —NH—, or —CONH—;
and
R 16 represents a hydrogen atom, an optionally substituted C1-C35 aliphatic hydrocarbon group, an optionally substituted C6-C35 aromatic ring-containing hydrocarbon group, or an optionally substituted C2-C35 heterocyclic ring-containing group, the aliphatic hydrocarbon group, aromatic ring-containing hydrocarbon group, and heterocyclic ring-containing group being optionally substituted by a combination of one or more groups selected from a carbon-carbon double bond, —O—, —S—, —CO—, —O—CO—, —CO—O—, and —SO 2 —;

wherein Y 6 and Y 8 each independently represent —NR 17 — or an optionally

Assignees

• Adeka Corp

Inventors

• Okada Mitsuhiro
• Ariyoshi Tomoyuki

Classifications

• C08K5/11

  of acyclic polycarboxylic acids · CPC title

• C09B23/105

  two >CH- groups · CPC title

• C08K5/3475

  condensed with carbocyclic rings · CPC title

• C08K5/34924 Primary

  containing cyanurate groups; Tautomers thereof · CPC title

• C08K5/315

  Compounds containing carbon-to-nitrogen triple bonds · CPC title