IP Library › Granted Patent US 11,079,675
Granted Patent B2
US 11,079,675 · App. 16/096,401 · Granted Aug 3, 2021

Compound, photocurable composition, cured product of same, printing ink, and printed matter curing the printing ink

Inventors: Masanori Miyamoto (Sakura, JP); Keisuke Wakahara (Tokyo, JP); Tomokazu Yamada (Tokyo, JP)
Assignee: DIC CORPORATION
G03F7/027C07D241/04C07D295/192C08F2/50C09D11/101G03F7/031C08F290/06
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Quick Facts
Patent No.
US 11,079,675
App. No.
16/096,401
Granted
Aug 3, 2021
Kind
B2
Abstract

A novel compound is used as a novel photopolymerization initiator, the novel compound having a molecular structure represented by general formula 1 below [R 1 represents an alkyl group having 1 to 10 carbon atoms, R 2 represents an alkyl group having 1 to 12 carbon atoms or the like, R 3 represents an alkyl group having 1 to 12 carbon atoms or the like, R 4 to R 7 each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or the like, Y 1 represents an alkyl group having 3 to 19 carbon atoms or the like, Y 2 represents an organic linking group, X 1 represents an ethylene group or the like, X 2 and X 3 each represent an ethylene group or the like, Y 3 represents a single bond or an alkylidene group, and n represents an integer of 1 to 3].

Claims (42)

1. A novel compound having a molecular structure represented by general formula 1 below,

wherein R 1 is an alkyl group having 1 to 10 carbon atoms, R 2 is an alkyl group having 1 to 12 carbon atoms, a hydroxyalkyl group having 2 to 4 carbon atoms, or an alkyl group having 2 to 4 carbon atoms and substituted by an alkoxy group having 1 or 2 carbon atoms, R 3 is an alkyl group having 1 to 12 carbon atoms, a hydroxyalkyl group having 2 to 4 carbon atoms, a methoxyethyl group, or an ethoxyethyl group, R 2 and R 3 are alkylene groups which are combined to form a cyclic structure together with a nitrogen atom, R 2 and R 3 are cyclic structure-forming parts which are combined to form a morpholine skeleton, a N-methylpiperazine skeleton, or a 2,6-dimethylmorpholine skeleton together with a nitrogen atom,

R 4 to R 7 are each independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group,

Y 1 is an alkyl group (y1-1) selected from the group consisting of a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a 1-methylundecyl group, a 1-chlorododecyl group, a 1,1,1-trichlorododecyl group, a 1-chlorooctadecyl group, a 1,1,1-trichlorooctadecyl group, a 1-hydroxydodecyl group, a 1-hydroxyoctadecyl group, an aralkyl group (y1-2) having 7 to 19 carbon atoms, a structural part represented by structural formulae (y1-3), (y1-4), (y1-5), (y1-6), (y1-7), (y1-8) and (y1-9) below

R 9 —O R 8 —O m R 8 —  (y1-3)

in the formula (y1-3), R 8 represents an alkylene group having 2 to 4 carbon atoms, R 9 represents a hydrogen atom, a phenyl group, or an alkyl group having 1 to 4 carbon atoms, and m represents an integer of 0 to 20,

a structural part (y1-4) represented by structural formula (y1-4) below

in the formula (y1-4), R 8 represents an alkylene group having 2 to 4 carbon atoms, R 9 represents a hydrogen atom, a phenyl group, or an alkyl group having 1 to 4 carbon atoms, R 10 represents a hydrogen atom or a methyl group, and m represents an integer of 0 to 20, a structural part (y1-5) represented by structural formula (y1-5) below

in the formula (y1-5), R 10 represents a hydrogen atom or a methyl group, and Ru represents a group selected from the group consisting of a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a 2-ethylbutyl group, an isopentyl group, a 1-methylpentyl group, a 1,3-dimethylbutyl group, a 1-methylhexyl group, an isoheptyl group, a 1,1,3,3-tetramethylbutyl group, a 2,2,4,4-tetramethylbutyl group, a 1-methylheptyl group, a 3-methylheptyl group, a 2-ethylhexyl group, a 1,1,3-trimethylhexyl group, a 1,1,3,3-tetramethylpentyl group, an isodecyl group, a 1-methylundecyl group, a 1,1,3,3,5,5-hexamethylhexyl group, a cycloheptyl group, a cyclohexyl group, a cyclopentyl group, or an aryl group having 6 to 18 carbon atoms,

a structural part (y1-6) represented by structural formula (y1-6) below

in the formula (y1-6), R 12 represents a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a 2-ethylbutyl group, an isopentyl group, a 1-methylpentyl group, a 1,3-dimethylbutyl group, a 1-methylhexyl group, an isoheptyl group, a 1,1,3,3-tetramethylbutyl group, a 2,2,4,4-tetramethylbutyl group, a 1-methylheptyl group, a 3-methylheptyl group, a 2-ethylhexyl group, a 1,1,3-trimethylhexyl group, a 1,1,3,3-tetramethylpentyl group, an isodecyl group, a 1-methylundecyl group, a 1,1,3,3,5,5-hexamethylhexyl group, a cycloheptyl group, a cyclohexyl group, or a cyclopentyl group,

a structural part (y1-7) represented by structural formula (y1-7) below

in the formula (y1-7), R 8 represents an alkylene group having 2 to 4 carbon atoms, R 13 represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a halogen atom, and m represents an integer of 0 to 20,

a structural part (y1-8) represented by structural formula (y1-8) below

in the formula (y1-8), R 8 each independently represent an alkylene group having 2 to 4 carbon atoms, R 10 represents a hydrogen atom or a methyl group, R 14 represents a hydrocarbon group having 3 to 25 carbon atoms and (p+1) bonds, 1 represents an integer of 0 to 20, and p represents an integer of 1 to 3, or

a structural part (y1-9) represented by structural formula (y1-9) below

in the formula (y1-9), R 15 represents an alkyl group having 4 to 18 carbon atoms, an aliphatic cyclic hydrocarbon group having 6 to 10 carbon atoms, or an aromatic group,

X 1 is an ethylene group, a 1,3-propylene group, a 1,2-propylene group, or a 2,3-propylene group,

X 2 is a hydrogen atom or a methyl group, X 3 is a hydrogen atom, a methyl group, or an ethyl group,

or X 2 and X 3 integrally represent an ethylene group, a 1,3-propylene group, a 1,2-propylene group, or a 2,3-propylene group while forming a covalent bond in a broken line portion, or X 1 , X 2 , and X 3 integrally represent a tetravalent aliphatic hydrocarbon group which forms a bicyclo ring together with a nitrogen atom and is represented by structural formula below

Y2 represents a structural part structural part represented by one selected from the group consisting of formulae (y2-1) to (y2-9) below:

—NH—R 16 —NH—  (y2-1)

in the formula (y2-1), R 16 represents a linear or cyclic alkylene group having 2 to 18 carbon atoms, a phenylene group, a xylylene group, a phenylene group having an alkyl group having 1 to 3 carbon atoms as a nuclear substituent, or a xylylene group having an alkyl group having 1 to 3 carbon atoms as a nuclear substituent),

—NH—R 17 O—R 18 O—R 17 —NH—  (y2-2)

in the formula (y2-2), R 17 represents a linear or branched alkylene group having 2 to 6 carbon atoms or a phenylene group, R 18 represents a linear or branched alkylene group having 2 to 6 carbon atoms or a phenylene group, and q represents an integer of 1 to 22),

in the formula (y2-3), R 19 to R 22 each independently represent a hydrogen atom or a linear or branched alkyl group having 1 to 3 carbon atoms,

in the formula (y2-4), R 23 represents an oxygen atom, a methylene group, an ethylene group, an ethylidene group, a 2,2-propylene group, or a 1,3-propylene group,

in the formula (y2-5), R 24 each independently represent a hydrogen atom or a linear or branched alkyl group having 1 to 3 carbon atoms, R 25 each independently represent a hydrogen atom or a linear or branched alkyl group having 1 to 3 carbon atoms, and R 26 represents an oxygen atom, a methylene group, a 2,2-propylene group, a sulfonyl group, or a carbonyl group, or in the general formula 1, n is 2 or 3,

in the formula (y2-6), R 27 represents an alkylene group having 2 to 6 carbon atoms, R 28 represents a hydrocarbon group having 4 to 12 carbon atoms and a number of bonds of (n+1), and r represents an integer of 0 to 3,

—O—R 29 —O—  (y2-7)

in the formula (y2-7), R 29 represents a linear, branched, or cyclic alkylene group having 2 to 18 carbon atoms, a phenylene group, or a xylylene group

—O—R 30 O—R 30 q O—  (y2-8)

in the formula (y2-8), R 30 each independently represent an alkylene group having 2 to 6 carbon atoms, and q represents an integer of 1 to 20), or in the general formula 1, n is 2 or 3,

in the formula (y2-9), R 31 represents a hydrocarbon group having 4 to 12 carbon atoms and a number of bonds of (n+1)), R 32 represents an alkylene group having 2 to 6 carbon atoms, and s represents an integer of 0 to 3,

Y 3 represents a single bond, an alkylene group having 1 to 3 carbon atoms, or an alkylidene group having 1 to 3 carbon atoms, and

n represents an integer of 1 when Y2 is one of (y2-1) to (y2-5), (y2-7) and (y2-8), or an integer of 2 or 3 when Y2 is one of (y2-6) or (y2-9).

2. The novel compound according to claim 1 , wherein in the general formula 1, the total number of structural parts represented by structural formula 1a below is 300 to 2000,

in the structural formula 1a, R 4 to R 7 , X 1 to X 3 , and Y 1 represent the same meanings as in the general formula 1.

3. A polymerization initiator comprising the novel compound according to claim 1 .

4. A photocurable composition comprising the photopolymerization initiator according to claim 3 and a photocurable compound as essential components.

5. A cured product produced by curing the photocurable composition according to claim 4 .

6. A photocurable printing ink comprising the photocurable composition according to claim 4 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 25, 2018
From: MIYAMOTO, MASANORI; WAKAHARA, KEISUKE; YAMADA, TOMOKAZU
To: DIC CORPORATION
Reel/Frame 047312/0953 →
Priority Claims (1)
JP JP2016-097074 · May 13, 2016 · national
Continuity (1)
Related Publication 20190137872A1 · May 9, 2019
Cited By (1)
US 12,215,248