# US 10,870,769 B2 · Photocurable ink composition and image forming method

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- Number: US 10,870,769 B2
- Document ID: US10870769B2
- Status: Granted
- Kind: B2
- Application number: 16/695,074
- Filed: 2019-11-25
- Published: 2020-03-26
- Granted: 2020-12-22
- Earliest claimed: 2017-06-20
- Assignees: FUJIFILM Corporation
- Applicants: Fujifilm Corporation
- Inventors: Ichiro Koyama; Noriaki Sato; Shota Suzuki; Yasuhiro Sawamura
- Web page: https://patentgrep.com/patent/US10870769B2

## CPC

- B41M 7/0081: {using electromagnetic radiation or waves, e.g. ultraviolet radiation, electron beams}
- B41M 5/0023: {Digital printing methods characterised by the inks used (inks per se C09D11/00)}
- 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
- C09D 11/102: containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds
- C09D 11/107: from unsaturated acids or derivatives thereof
- C09D 11/30: Inkjet printing inks
- B41M: PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING, (correction of typographical errors B41J; processes for applying transfer pictures or the like B44C1/16; fluid media for correction of typographical errors by coating C09D10/00; printing textiles D06P)
- 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

Provided is a photocurable ink composition including a resin which has an amine structure having an α-hydrogen atom and contains at least one selected from the group consisting of an alkylthio group, an alkylenethioalkylene group, and a mercapto group and at least one selected from the group consisting of a fluorinated hydrocarbon group, a polysiloxane group, and a hydrocarbon group having 12 or more carbon atoms; at least one of a monofunctional radically polymerizable monomer or a bifunctional radically polymerizable monomer; and a photopolymerization initiator.

## Claims

### Claim 1

A photocurable ink composition comprising:
a resin which has an amine structure having an α-hydrogen atom and contains at least one selected from the group consisting of an alkylthio group, an alkylenethioalkylene group, and a mercapto group and at least one selected from the group consisting of a fluorinated hydrocarbon group, a polysiloxane group, and a hydrocarbon group having 12 or more carbon atoms;
at least one of a monofunctional radically polymerizable monomer or a bifunctional radically polymerizable monomer; and
a photopolymerization initiator,
wherein a weight-average molecular weight of the resin is in a range of 5000 to 30000.

### Claim 2 (depends on 1)

The photocurable ink composition according to claim 1,
wherein the resin has a structural unit (1) which has an amine structure having an α-hydrogen atom;
a structural unit (2) which contains at least one selected from the group consisting of an alkylthio group, an alkylenethioalkylene group, and a mercapto group; and
a structural unit (3) which contains at least one selected from the group consisting of a fluorinated hydrocarbon group, a polysiloxane group, and a hydrocarbon group having 12 or more carbon atoms.

### Claim 3 (depends on 1)

The photocurable ink composition according to claim 1,
wherein the resin contains an alkylthio group.

### Claim 4 (depends on 1)

The photocurable ink composition according to claim 1,
wherein the resin contains an alkylthio group as a terminal group in a main chain.

### Claim 5 (depends on 1)

The photocurable ink composition according to claim 1,
wherein the resin is a (meth)acrylic resin.

### Claim 6 (depends on 1)

The photocurable ink composition according to claim 1,
wherein the resin has a structural unit (1A) and a structural unit (3A),
in the structural unit (1A), R11 represents a hydrogen atom or a methyl group, R12, R13, and R14 each independently represent a hydrogen atom or a hydrocarbon group, L11 represents a linking group, and two symbols “*” each represent a bonding position, R12 and L11 may be linked to each other to form a ring, and R12 and R13 may be linked to each other to form a ring, and
in the structural unit (3A), R31 represents a hydrogen atom or a methyl group, L31 represents a single bond or a linking group, X31 represents a fluorinated hydrocarbon group, a monovalent group containing a polysiloxane group, or a hydrocarbon group having 12 or more carbon atoms, and two symbols “*” each represent a bonding position.

### Claim 7 (depends on 1)

The photocurable ink composition according to claim 1,
wherein the amine structure having an α-hydrogen atom is a tertiary amine structure in which three carbon atoms are bonded to one nitrogen atom,
the three carbon atoms are each independently a carbon atom in a methyl group, a primary carbon atom, or a secondary carbon atom, and
any of all the three carbon atoms is not a carbon atom in a methyl group.

### Claim 8 (depends on 1)

The photocurable ink composition according to claim 1,
wherein the amine structure having an α-hydrogen atom is a dimethylaminoalkyl group.

### Claim 9 (depends on 1)

The photocurable ink composition according to claim 1,
wherein the amount of an ethylenically unsaturated bond in the resin is in a range of 0 mmol/g to 1.0 mmol/g.

### Claim 10 (depends on 1)

The photocurable ink composition according to claim 1,
wherein a total content of the monofunctional radically polymerizable monomer and the bifunctional radically polymerizable monomer is 50% by mass or greater with respect to a total amount of the photocurable ink composition.

### Claim 11 (depends on 1)

An image forming method comprising:
a step of applying the photocurable ink composition according to claim 1 onto a base material to form an ink film; and
a step of irradiating the ink film with active energy rays and curing the ink film to form an image.
