Lithographic printing plate precursor, and method for producing lithographic printing plate

Patent metadata

Field	Value
Publication number	US-11294279-B2
Application number	US-201916599394-A
Country	US
Kind code	B2
Filing date	Oct 11, 2019
Priority date	Jul 13, 2017
Publication date	Apr 5, 2022
Grant date	Apr 5, 2022

Abstract

A lithographic printing plate precursor including an image recording layer on a hydrophilic support, in which the image recording layer includes a polymerization initiator, an infrared absorbent, a polymerizable compound, and an acid color former, and the infrared absorbent includes a compound represented by Formula 1, as well as a method of preparing a lithographic printing plate by use of the lithographic printing plate precursor. In Formula 1, at least one of Ar1 or Ar2 has a group represented by —X, where X represents a halogen atom, —C(═O)—X2—R11, —C(═O)—NR12R13, —O—C(═O)—R14, —CN, —SO2N15R16, or a perfluoroalkyl group, X2 represents a single bond or an oxygen atom, R11 and R14 each independently represents an alkyl group or an aryl group, and R12, R13, R15 and R16 each independently represents a hydrogen atom, an alkyl group, or an aryl group:

First claim

What is claimed is:

1. A method of preparing a lithographic printing plate, comprising
imagewise exposing a lithographic printing plate precursor, thereby forming an exposed portion and an unexposed portion, and
feeding at least one of printing ink or dampening water, thereby removing the unexposed portion, wherein
the lithographic printing plate precursor comprises an image recording layer on a hydrophilic support,
the image recording layer comprises a polymerization initiator, an infrared absorbent, a polymerizable compound, a polymer particle, and an acid color former,
the infrared absorbent comprises a compound represented by the following Formula 1, and
the difference between the highest occupied molecular orbital (HOMO) of the compound represented by Formula 1 and the highest occupied molecular orbital of the polymerization initiator is 0.57 eV or less:

wherein R 1 and R 2 each independently represents a hydrogen atom or an alkyl group, R 1 and R 2 are optionally mutually linked to form a ring, R 3 to R 6 each independently represents a hydrogen atom or an alkyl group, R 7 and R 8 each independently represents an alkyl group or an aryl group, Y 1 and Y 2 each independently represents an oxygen atom, a sulfur atom, —NR 0 — or a dialkylmethylene group, R 0 represents a hydrogen atom, an alkyl group, or an aryl group, Ar 1 and Ar 2 each independently represents a group that forms a benzene ring or a naphthalene ring optionally having —X described below, A 1 represents —NR 9 R 10 , —X 1 -L 1 , or —X described below, R 9 and R 10 each independently represent an alkyl group, an aryl group, an alkoxycarbonyl group, or an arylsulfonyl group, X 1 represents an oxygen atom or a sulfur atom, L 1 represents a hydrocarbon group, a heteroaryl group, or a group where a bond with X 1 is to be cleaved by heat or infrared exposure, Za represents a counter ion that neutralizes charge, and at least one of Ar 1 or Ar 2 has —X, X represents a halogen atom, —C(═O)—X 2 —R 11 , —C(═O)—NR 12 R 13 , —O—C(═O)—R 14 , —CN, —SO 2 NR 15 R 16 , or a perfluoroalkyl group, X 2 represents a single bond or an oxygen atom, R 11 and R 14 each independently represents an alkyl group or an aryl group, and R 12 , R 13 , R 15 and R 16 each independently represents a hydrogen atom, an alkyl group, or an aryl group.

2. A method of preparing a lithographic printing plate, comprising
imagewise exposing a lithographic printing plate precursor, thereby forming an exposed portion and an unexposed portion, and
at least one of printing ink or dampening water, thereby removing the unexposed portion, wherein
the lithographic printing plate precursor comprises an image recording layer on a hydrophilic support,
the image recording layer comprises a polymerization initiator, an infrared absorbent, a polymerizable compound, and an acid color former,
the polymerization initiator comprises a tetraarylborate compound,
the polymerizable compound comprises a urethane-based addition-polymerizable compound,
the infrared absorbent comprises a compound represented by the following Formula 1, and
the difference between the highest occupied molecular orbital (HOMO) of the compound represented by Formula 1, and the HOMO of the polymerization initiator is 0.57 eV or less;

wherein R 1 and R 2 each independently represents a hydrogen atom or an alkyl group, R 1 and R 2 are optionally mutually linked to form a ring, R 3 to R 6 each independently represents a hydrogen atom or an alkyl group, R 7 and R 8 each independently represents an alkyl group or an aryl group, Y 1 and Y 2 each independently represents an oxygen atom, a sulfur atom, —NR 0 — or a dialkylmethylene group, R 0 represents a hydrogen atom, an alkyl group, or an aryl group, Ar 1 and Ar 2 each independently represents a group that forms a benzene ring or a naphthalene ring optionally having —X described below, A 1 represents —NR 9 R 10 , —X 1 -L 1 , or —X described below, R 9 and R 10 each independently represent an alkyl group, an aryl group, an alkoxycarbonyl group, or an arylsulfonyl group, X 1 represents an oxygen atom or a sulfur atom, L 1 represents a hydrocarbon group, a heteroaryl group, or a group where a bond with X 1 is to be cleaved by heat or infrared exposure, Za represents a counter ion that neutralizes charge, and at least one of Ar 1 or Ar 2 has —X, X represents a halogen atom, —C(═O)—X 2 —R 11 , —C(═O)—NR 12 R 13 , —O—C(═O)—R 14 , —CN, or —SO 2 NR 15 R 16 , or a perfluoroalkyl group, X 2 represents a single bond or an oxygen atom, R 11 and R 14 each independently represents an alkyl group or an aryl group, and R 12 , R 13 , R 15 and R 16 each independently represents a hydrogen atom, an alkyl group, or an aryl group.

3. The method according to claim 1 , wherein X represents a fluorine atom, a chlorine atom, or —C(═O)OR 17 , provided that R 17 represents an alkyl group or an aryl group.

4. The method according to claim 1 , wherein A 1 in Formula 1 represents —NR 18 R 19 or —S—R 20 , provided that R 18 and R 19 each independently represents an aryl group and R 20 represents a hydrocarbon group or a heteroaryl group.

5. The method according to claim 1 , wherein the polymerization initiator is a borate compound.

6. The method according to claim 5 , wherein the borate compound is a tetraarylborate compound or a monoalkyltriarylborate compound.

7. The method according to claim 1 , wherein the polymerization initiator comprises an electron-donating polymerization initiator and an electron-accepting polymerization initiator.

8. The method according to claim 1 , wherein the acid color former is at least one compound selected from the group consisting of a spirolactone compound and a spirolactam compound.

9. The method according to claim 1 , wherein Za represents a carbon atom-containing organic anion.

10. The method according to claim 1 , wherein Za represents a sulfonimide anion.

11. The method according to claim 1 , wherein the polymerizable compound comprises an ester compound of unsaturated carboxylic acid.

12. The method according to claim 5 , wherein the polymerizable compound comprises an ester compound of unsaturated carboxylic acid.

13. The method according to claim 1 , wherein X represents a halogen atom, —C(═O)—X 2 —R 11 , —C(═O)—NR 12 R 13 , —O—C(═O)—R 14 , —CN, or —SO 2 NR 15 R 16 .

14. The method according to claim 1 , wherein the difference between the HOMO of the compound represented by Formula 1 and the HOMO of the polymerization initiator is 0.45 eV or more.

15. The method according to claim 1 , wherein, in Formula 1, Za represents a sulfonamide anion or a sulfonimide anion.

16. The method according to claim 2 , wherein X represents a halogen atom, —C(═O)—X 2 —R 11 , —C(═O)—NR 12 R 13 , —O—C(═O)—R 14 , —CN, or —SO 2 NR 15 R 16 .

17. The method according to claim 2 , wherein the image recording layer further comprises a polymer particle.

18. The method according to claim 2 , wherein the difference between the HOMO of the compound represented by Formula 1 and the HOMO of the polymerization initiator is 0.45 eV or more.

19. The method according to claim 2 , wherein, in Formula 1, Za represents a sulfonamide anion or a sulfonimide anion.

Assignees

• Fujifilm Corp

Inventors

• Ishiji Yohei
• Nogoshi Keisuke
• Inasaki Takeshi

Classifications

• B41C1/1008 Primary

  by removal or destruction of lithographic material on the lithographic support, e.g. by laser or spark ablation; by the use of materials rendered soluble or insoluble by heat exposure, e.g. by heat produced from a light to heat transforming system; by on-the-press exposure or on-the-press development, e.g. by the fountain of photolithographic materials · CPC title

• G03F7/027 Primary

  Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds (G03F7/075 takes precedence) · CPC title

• B41C2201/10

  characterised by inorganic compounds, e.g. pigments · CPC title

• B41C2210/22

  characterised by organic non-macromolecular additives, e.g. dyes, UV-absorbers, plasticisers · CPC title

• B41C2210/04

  Negative working, i.e. the non-exposed (non-imaged) areas are removed · CPC title