# US 11,079,675 B2 · Compound, photocurable composition, cured product of same, printing ink, and printed matter curing the printing ink

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- Number: US 11,079,675 B2
- Document ID: US11079675B2
- Status: Granted
- Kind: B2
- Application number: 16/096,401
- Filed: 2017-02-21
- Published: 2019-05-09
- Granted: 2021-08-03
- Earliest claimed: 2016-05-13
- Assignees: DIC Corporation
- Applicants: DIC Corporation
- Inventors: Masanori Miyamoto; Keisuke Wakahara; Tomokazu Yamada
- Web page: https://patentgrep.com/patent/US11079675B2

## CPC

- G03F 7/027: Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds (G03F7/075 takes precedence)
- C07D 241/04: having no double bonds between ring members or between ring members and non-ring members
- C07D 295/192: from aromatic carboxylic acids
- C08F 2/50: with sensitising agents
- C09D 11/101: Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
- G03F 7/031: Organic compounds not covered by group G03F7/029
- C08F 290/06: Polymers provided for in subclass C08G
- G03F: PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR; (phototypographic composing devices B41B; photosensitive materials or processes for photographic purposes G03C; electrophotography, sensitive layers or processes therefor G03G)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)

## Abstract

A novel compound is used as a novel photopolymerization initiator, the novel compound having a molecular structure represented by general formula 1 below [R1 represents an alkyl group having 1 to 10 carbon atoms, R2 represents an alkyl group having 1 to 12 carbon atoms or the like, R3 represents an alkyl group having 1 to 12 carbon atoms or the like, R4 to R7 each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or the like, Y1 represents an alkyl group having 3 to 19 carbon atoms or the like, Y2 represents an organic linking group, X1 represents an ethylene group or the like, X2 and X3 each represent an ethylene group or the like, Y3 represents a single bond or an alkylidene group, and n represents an integer of 1 to 3].

## Claims

### Claim 1

A novel compound having a molecular structure represented by general formula 1 below,
wherein R1 is an alkyl group having 1 to 10 carbon atoms, R2 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, R3 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, R2 and R3 are alkylene groups which are combined to form a cyclic structure together with a nitrogen atom, R2 and R3 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,
R4 to R7 are each independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group,
Y1 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
R9—OR8—OmR8— (y1-3)
in the formula (y1-3), R8 represents an alkylene group having 2 to 4 carbon atoms, R9 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), R8 represents an alkylene group having 2 to 4 carbon atoms, R9 represents a hydrogen atom, a phenyl group, or an alkyl group having 1 to 4 carbon atoms, R10 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), R10 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), R12 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), R8 represents an alkylene group having 2 to 4 carbon atoms, R13 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), R8 each independently represent an alkylene group having 2 to 4 carbon atoms, R10 represents a hydrogen atom or a methyl group, R14 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), R15 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,
X1 is an ethylene group, a 1,3-propylene group, a 1,2-propylene group, or a 2,3-propylene group,
X2 is a hydrogen atom or a methyl group, X3 is a hydrogen atom, a methyl group, or an ethyl group,
or X2 and X3 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 X1, X2, and X3 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—R16—NH— (y2-1)
in the formula (y2-1), R16 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—R17O—R18O—R17—NH— (y2-2)
in the formula (y2-2), R17 represents a linear or branched alkylene group having 2 to 6 carbon atoms or a phenylene group, R18 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), R19 to R22 each independently represent a hydrogen atom or a linear or branched alkyl group having 1 to 3 carbon atoms,
in the formula (y2-4), R23 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), R24 each independently represent a hydrogen atom or a linear or branched alkyl group having 1 to 3 carbon atoms, R25 each independently represent a hydrogen atom or a linear or branched alkyl group having 1 to 3 carbon atoms, and R26 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), R27 represents an alkylene group having 2 to 6 carbon atoms, R28 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—R29—O— (y2-7)
in the formula (y2-7), R29 represents a linear, branched, or cyclic alkylene group having 2 to 18 carbon atoms, a phenylene group, or a xylylene group
—O—R30O—R30qO— (y2-8)
in the formula (y2-8), R30 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), R31 represents a hydrocarbon group having 4 to 12 carbon atoms and a number of bonds of (n+1)), R32 represents an alkylene group having 2 to 6 carbon atoms, and s represents an integer of 0 to 3,
Y3 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).

### Claim 2 (depends on 1)

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, R4 to R7, X1 to X3, and Y1 represent the same meanings as in the general formula 1.

### Claim 3 (depends on 1)

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

### Claim 4 (depends on 3)

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

### Claim 5 (depends on 4)

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

### Claim 6 (depends on 4)

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