WO2020090996A1 - Plaque originale de plaque d'impression lithographique, procédé de production de plaque d'impression lithographique et procédé d'impression lithographique - Google Patents

Plaque originale de plaque d'impression lithographique, procédé de production de plaque d'impression lithographique et procédé d'impression lithographique Download PDF

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Publication number
WO2020090996A1
WO2020090996A1 PCT/JP2019/042872 JP2019042872W WO2020090996A1 WO 2020090996 A1 WO2020090996 A1 WO 2020090996A1 JP 2019042872 W JP2019042872 W JP 2019042872W WO 2020090996 A1 WO2020090996 A1 WO 2020090996A1
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Prior art keywords
group
printing plate
lithographic printing
compound
plate precursor
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PCT/JP2019/042872
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English (en)
Japanese (ja)
Inventor
啓介 野越
彬 阪口
Original Assignee
富士フイルム株式会社
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Priority claimed from JP2019122487A external-priority patent/JP2020069790A/ja
Application filed by 富士フイルム株式会社 filed Critical 富士フイルム株式会社
Priority to EP19880350.4A priority Critical patent/EP3875282A4/fr
Priority to CN201980071585.7A priority patent/CN112930266B/zh
Publication of WO2020090996A1 publication Critical patent/WO2020090996A1/fr

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41C—PROCESSES FOR THE MANUFACTURE OR REPRODUCTION OF PRINTING SURFACES
    • B41C1/00—Forme preparation
    • B41C1/10—Forme preparation for lithographic printing; Master sheets for transferring a lithographic image to the forme
    • B41C1/1008—Forme preparation for lithographic printing; Master sheets for transferring a lithographic image to the forme 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
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • 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
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • 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
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • 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
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • 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
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • 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
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • 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
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41C—PROCESSES FOR THE MANUFACTURE OR REPRODUCTION OF PRINTING SURFACES
    • B41C2210/00—Preparation or type or constituents of the imaging layers, in relation to lithographic printing forme preparation
    • B41C2210/04—Negative working, i.e. the non-exposed (non-imaged) areas are removed
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41C—PROCESSES FOR THE MANUFACTURE OR REPRODUCTION OF PRINTING SURFACES
    • B41C2210/00—Preparation or type or constituents of the imaging layers, in relation to lithographic printing forme preparation
    • B41C2210/08—Developable by water or the fountain solution
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41C—PROCESSES FOR THE MANUFACTURE OR REPRODUCTION OF PRINTING SURFACES
    • B41C2210/00—Preparation or type or constituents of the imaging layers, in relation to lithographic printing forme preparation
    • B41C2210/22—Preparation or type or constituents of the imaging layers, in relation to lithographic printing forme preparation characterised by organic non-macromolecular additives, e.g. dyes, UV-absorbers, plasticisers

Definitions

  • the present disclosure relates to a lithographic printing plate precursor, a method for producing a lithographic printing plate, and a lithographic printing method.
  • a lithographic printing plate comprises a lipophilic image area that receives ink during the printing process and a hydrophilic non-image area that receives fountain solution.
  • the lipophilic image part of the lithographic printing plate is used as the ink receiving part and the hydrophilic non-image part is dampening water receiving part (ink non-receiving part) by utilizing the property that water and oil-based ink repel each other.
  • a difference in ink adhesion is caused on the surface of the lithographic printing plate, the ink is applied only to the image area, and then the ink is transferred to a printing medium such as paper for printing.
  • a lithographic printing plate precursor in which a lipophilic photosensitive resin layer (image recording layer) is provided on a hydrophilic support has been widely used.
  • the lithographic printing plate precursor is exposed through an original image such as a lith film, and then a portion to be an image portion of the image recording layer is left, and the other unnecessary image recording layer is treated with an alkaline developer or an organic solvent.
  • a lithographic printing plate is obtained by carrying out plate making by a method of dissolving and removing with a solvent and exposing the surface of a hydrophilic support to form a non-image area.
  • Y 2 - has the following structure:
  • R 1 and R 2 are independently optionally substituted.
  • a hydrocarbon group, or two of the R 1 , R 2 , R d or R a groups described above comprise the atoms necessary to form a cyclic structure together and at least 1 of the R d groups One is a group that is converted to a group that is an electron-donor stronger than R d by a chemical reaction induced by IR-irradiation or exposure to heat, or at least one of the R a groups is IR-irradiated.
  • R d and R a groups are independently a hydrogen atom, a halogen atom, R e, -OR f, selected from the list consisting of -SR g and -NR u R v
  • the display by a group wherein R e, R f, R g , R u and R v is an optionally substituted optionally which may aliphatic hydrocarbon group or a substituted independently optionally ( Hetero) aryl groups, and are characterized in that the above conversion provides an integrated increase in light absorption of the dye between 400 and 700 nm.
  • color-forming composition used in the conventional lithographic printing plate precursor examples include those described in Patent Document 2.
  • Patent Document 2 describes a color-forming composition containing a compound represented by the following formula 1.
  • R 1 represents a group in which the R 1 —O bond is cleaved by heat or infrared exposure
  • R 2 and R 3 each independently represent a hydrogen atom or an alkyl group
  • R 2 and R 3 are linked to each other.
  • Ar 1 and Ar 2 each independently represent a group that forms a benzene ring or a naphthalene ring
  • Y 1 and Y 2 each independently represent an oxygen atom, a sulfur atom, or —NR.
  • R 4 and R 5 each independently represent an alkyl group
  • R 6 to R 9 each independently represent a hydrogen atom or an alkyl group
  • R 0 represents a hydrogen atom or an alkyl group. Or, it represents an aryl group
  • Za represents a counter ion that neutralizes charge.
  • Patent Document 1 Japanese Patent Publication No. 2008-544053 Publication
  • Patent Document 2 International Publication No. 2016/027886
  • the problem to be solved by one embodiment of the present disclosure is to provide a lithographic printing plate precursor capable of obtaining a lithographic printing plate having excellent printing durability even when a UV ink is used.
  • a problem to be solved by another embodiment of the present disclosure is to provide a method for producing a planographic printing plate using the planographic printing plate precursor, and a planographic printing method using the planographic printing plate precursor.
  • Means for solving the above problems include the following aspects. ⁇ 1> having an image recording layer on a support,
  • the image recording layer contains an infrared absorber represented by the following formula 1-1, a polymerization initiator, and a polymerizable compound, Original planographic printing plate.
  • R 1 represents a group represented by the following Formula 2, and R 11 to R 18 each independently represent a hydrogen atom, a halogen atom, —R a , —OR b , —SR c or —NR.
  • R e , R a to R e each independently represents a hydrocarbon group, and A 1 , A 2 and a plurality of R 11 to R 18 may combine to form a monocyclic or polycyclic ring.
  • a 1 and A 2 each independently represent an oxygen atom, a sulfur atom or a nitrogen atom
  • n 11 and n 12 each independently represent an integer of 0 to 5, provided that the sum of n 11 and n 12 is 2 or more
  • n 13 and n 14 each independently represent 0 or 1
  • L represents an oxygen atom, a sulfur atom or —NR 10 —
  • R 10 represents a hydrogen atom, an alkyl group or an aryl group
  • Za represents a counter ion that neutralizes charge.
  • R Z represents an alkyl group
  • the wavy line represents a bonding site with the group represented by L in Formula 1-1.
  • R 1 represents a group represented by the following Formula 2
  • R 2 and R 3 each independently represent a hydrogen atom or an alkyl group
  • R 2 and R 3 are linked to each other to form a ring.
  • Ar 1 and Ar 2 each independently represent a group forming a benzene ring or a naphthalene ring
  • Y 1 and Y 2 are each independently oxygen atom, sulfur atom, —NR 0 — or dialkyl.
  • R 0 represents a hydrogen atom, an alkyl group or an aryl group
  • R 4 and R 5 each independently represents an alkyl group, a —CO 2 M group or a —PO 3 M 2 group
  • M represents a hydrogen atom.
  • R 6 to R 9 each independently represents a hydrogen atom or an alkyl group
  • L represents an oxygen atom, a sulfur atom or —NR 10 —
  • R 10 represents hydrogen.
  • Za represents a counter ion that neutralizes charge.
  • R Z represents an alkyl group
  • the wavy line represents a bonding site with the group represented by L in Formula 1-2 above.
  • L in the formula 1-1 represents a sulfur atom or —NR 10 —
  • the R 10 represents a hydrogen atom, an alkyl group or an aryl group.
  • R 4 and R 5 in Formula 1-2 above each independently represent a —R w4 —SO 3 M group, and M represents a hydrogen atom, a sodium atom, a potassium atom or an onium group
  • M represents a hydrogen atom, a sodium atom, a potassium atom or an onium group
  • ⁇ 5> The lithographic printing plate precursor as described in any one of the above items ⁇ 1> to ⁇ 4>, wherein L in the formula 1-1 is an oxygen atom.
  • ⁇ 6> The lithographic printing plate precursor as described in any one of ⁇ 1> to ⁇ 5>, wherein the polymerizable compound has a trifunctional or higher functional polymerizable group.
  • ⁇ 7> The lithographic printing plate precursor as described in any one of ⁇ 1> to ⁇ 5>, wherein the polymerizable compound has a 7-functional or higher-functional polymerizable group.
  • ⁇ 8> The lithographic printing plate precursor as described in any one of ⁇ 1> to ⁇ 5>, wherein the polymerizable compound has a 10- or more-functional polymerizable group.
  • ⁇ 9> The lithographic printing plate precursor as described in any one of ⁇ 1> to ⁇ 8> above, wherein the polymerizable compound has an ethylenically unsaturated bond equivalent of 200 g / mol or less.
  • ⁇ 10> The lithographic printing plate precursor as described in any one of ⁇ 1> to ⁇ 9>, wherein the polymerizable compound has CLogP of 6 or less.
  • ⁇ 11> The lithographic printing plate precursor as described in any one of ⁇ 1> to ⁇ 10> above, wherein the polymerizable group of the polymerizable compound contains a vinyl group or a (meth) acryloyl group.
  • the image recording layer further contains a binder polymer, The lithographic printing plate precursor as described in any one of the above items ⁇ 1> to ⁇ 11>, wherein the binder polymer has a structural unit formed of an aromatic vinyl compound.
  • ⁇ 13> The lithographic printing plate precursor as described in any one of ⁇ 1> to ⁇ 12>, wherein the image recording layer further contains polymer particles.
  • the polymer particles include polymer particles having a hydrophilic group.
  • the polymer particles have a polyalkylene oxide structure as the hydrophilic group.
  • the polymerization initiator contains at least one polymerization initiator selected from the group consisting of an electron donating polymerization initiator and an electron accepting polymerization initiator.
  • ⁇ 17> The lithographic printing plate precursor as described in ⁇ 16> above, wherein the electron-donating polymerization initiator is an onium salt compound.
  • the electron donative polymerization initiator has a HOMO of ⁇ 6.0 eV or more.
  • the electron accepting polymerization initiator has a LUMO of ⁇ 3.0 eV or less.
  • ⁇ 20> Any one of the above items ⁇ 16> to ⁇ 19>, wherein the polymerization initiator is a compound in which the electron donating polymerization initiator and the electron accepting polymerization initiator form a counter salt.
  • ⁇ 21> The lithographic printing plate precursor as described in any one of the above items ⁇ 1> to ⁇ 20>, wherein the image recording layer further contains an acid color former.
  • ⁇ 22> The lithographic printing plate precursor as described in any one of ⁇ 1> to ⁇ 21>, further having an overcoat layer on the image recording layer.
  • the support has an aluminum plate and an anodized film of aluminum arranged on the aluminum plate, The anodized film is located closer to the image recording layer than the aluminum plate, The anodized film has micropores extending in the depth direction from the surface of the image recording layer side,
  • the lithographic printing plate precursor as described in any one of the above items ⁇ 1> to ⁇ 22>, wherein the average diameter of the micropores on the surface of the anodized film is more than 10 nm and 100 nm or less.
  • the micropore communicates with a large-diameter hole extending from the surface of the anodic oxide film to a depth of 10 nm to 1,000 nm and the bottom of the large-pore, and a depth of 20 nm to 2 nm from the communicating position. It consists of a small-diameter hole that extends to the position of 1,000 nm, The average diameter of the large-diameter pores on the surface of the anodized film is 15 nm to 100 nm, The lithographic printing plate precursor as described in ⁇ 23>, wherein the average diameter of the small-diameter holes at the communicating position is 13 nm or less.
  • a step of exposing the lithographic printing plate precursor according to any one of ⁇ 1> to ⁇ 24> above in an imagewise manner A method for producing a lithographic printing plate, comprising the step of supplying at least one selected from the group consisting of printing ink and fountain solution on a printing machine to remove the image recording layer in the non-image area.
  • ⁇ 26> a step of imagewise exposing the lithographic printing plate precursor according to any one of the above items ⁇ 1> to ⁇ 24>, A step of producing a lithographic printing plate by supplying at least one selected from the group consisting of printing ink and fountain solution to remove the image recording layer of the non-image area on a printing machine, A planographic printing method comprising the step of printing with the obtained planographic printing plate.
  • a lithographic printing plate precursor capable of obtaining a lithographic printing plate having excellent printing durability even when a UV ink is used. Further, according to another embodiment of the present disclosure, it is possible to provide a method for producing a planographic printing plate using the planographic printing plate precursor and a planographic printing method using the planographic printing plate precursor.
  • FIG. 6 is a schematic cross-sectional view of another embodiment of an aluminum support.
  • FIG. 3 is a schematic diagram of an anodizing apparatus used for anodizing in the production of an aluminum support.
  • the present disclosure is not limited to such an embodiment.
  • “to” indicating a numerical range is used to mean that numerical values described before and after the numerical range are included as a lower limit value and an upper limit value.
  • the upper limit value or the lower limit value described in one numerical range may be replaced with the upper limit value or the lower limit value of another stepwise described numerical range. ..
  • the upper limit value or the lower limit value of the numerical range may be replaced with the value shown in the examples.
  • the amount of each component in the composition is the total amount of the corresponding substances present in the composition, unless a plurality of substances corresponding to each component are present in the composition.
  • the notation in which substitution and non-substitution are not included includes not only those having no substituent but also those having a substituent.
  • the “alkyl group” includes not only an alkyl group having no substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
  • (meth) acrylic is a term used as a concept including both acryl and methacryl
  • (meth) acryloyl” is a term used as a concept including both acryloyl and methacryloyl. Is.
  • each component in the composition or each structural unit in the polymer may be contained alone or in combination of two or more. .. Further, in the present disclosure, the amount of each component in the composition or each constitutional unit in the polymer is such that there are a plurality of substances or constitutional units corresponding to each component in the composition or each constitutional unit in the polymer.
  • the weight average molecular weight (Mw) and the number average molecular weight (Mn) in the present disclosure are columns of TSKgel GMHxL, TSKgel G4000HxL, and TSKgel G2000HxL (both manufactured by Tosoh Corp.) unless otherwise specified.
  • the term “lithographic printing plate precursor” includes not only the lithographic printing plate precursor but also the discarded plate precursor.
  • the term “lithographic printing plate” includes not only a lithographic printing plate precursor prepared through an operation such as exposure and development, but also a discarding plate, if necessary. In the case of a waste original plate, the operations of exposure and development are not always necessary.
  • the waste plate is a lithographic printing plate precursor to be attached to a plate cylinder that is not used, for example, when printing a part of the paper surface in monochrome or two colors in color newspaper printing.
  • “*” in the chemical structural formula represents a bonding position with another structure.
  • the lithographic printing plate precursor according to the present disclosure has an image recording layer on a support, and the image recording layer is an infrared absorbing agent represented by the following formula 1-1 (hereinafter, also referred to as “specific infrared absorbing agent”). .), A polymerization initiator, and a polymerizable compound.
  • the lithographic printing plate precursor according to the present disclosure is preferably an on-press development type lithographic printing plate precursor.
  • R 1 represents a group represented by Formula 2, and R 11 to R 18 each independently represent a hydrogen atom, a halogen atom, —Ra, —OR b , —SR c or —NR d R. represents e, Ra ⁇ Re each independently represent a hydrocarbon group, a 1, a 2 and a plurality of R 11 ⁇ R 18 may form a monocyclic or polycyclic linked is, a 1 and A 2 each independently represents an oxygen atom, a sulfur atom or a nitrogen atom, and n 11 and n 12 each independently represent an integer of 0 to 5, provided that the total of n 11 and n 12 is 2 or more.
  • N 13 and n 14 each independently represent 0 or 1
  • L represents an oxygen atom, a sulfur atom or —NR 10 —
  • R 10 represents a hydrogen atom, an alkyl group or an aryl group
  • Za represents a charge. Represents a counterion that neutralizes.
  • R Z represents an alkyl group
  • the wavy line represents a bonding site with the group represented by L in Formula 1-1.
  • UV printing durability printing durability
  • UV curing type ink UV curing type ink
  • the lithographic printing plate precursor according to the present disclosure contains an infrared absorbent having a specific structure in the image recording layer, and the infrared absorbent having the specific structure is considered to be easily decomposed because it has the specific structure. Further, the lithographic printing plate precursor according to the present disclosure, in the image recording layer, by using an infrared absorber having a specific structure, a polymerization initiator, and a polymerizable compound in combination, during the polymerization of the polymerizable compound, the infrared ray Since the absorbent or its decomposition product accelerates the polymerization, the polymerization efficiency is increased and a highly polar film can be obtained. Therefore, the printing durability (UV printing durability) is excellent even when the UV ink is used. I guess.
  • the planographic printing plate precursor according to the present disclosure is more likely to obtain excellent color developability with time. ..
  • details of each constituent element in the planographic printing plate precursor according to the present disclosure will be described.
  • the lithographic printing plate precursor according to the present disclosure has a support.
  • a support having a hydrophilic surface also referred to as “hydrophilic support”
  • the hydrophilic surface preferably has a contact angle with water of less than 10 °, more preferably less than 5 °.
  • the water contact angle in the present disclosure is measured by DM-501 manufactured by Kyowa Interface Science Co., Ltd. as the contact angle of a water drop on the surface at 25 ° C. (after 0.2 seconds).
  • the support of the lithographic printing plate precursor according to the present disclosure can be appropriately selected and used from known lithographic printing plate precursor supports.
  • the support an aluminum plate which has been roughened by a known method and subjected to anodization is preferable.
  • the aluminum plate may further include an enlargement treatment and a sealing treatment of micropores of an anodized film described in JP 2001-253181 A and JP 2001-322365 A, and US Pat. No. 2,714,14. No. 066, No. 3,181,461, No. 3,280,734, and No. 3,902,734, surface hydrophilization treatment with an alkali metal silicate, US A surface hydrophilization treatment using polyvinylphosphonic acid or the like as described in the respective specifications of Japanese Patent Nos. 3,276,868, 4,153,461 and 4,689,272 is appropriately selected. You may go.
  • the center line average roughness of the support is preferably 0.10 ⁇ m to 1.2 ⁇ m.
  • the support may have an organic polymer compound described in JP-A-5-45885 or a silicon alkoxy compound described in JP-A-6-35174 on the surface opposite to the image recording layer. It may have a back coat layer containing.
  • the aluminum support according to one embodiment of the present disclosure is also referred to as “support (1)”) is shown below. That is, the support (1) has an aluminum plate and an anodized film of aluminum arranged on the aluminum plate, and the anodized film is located closer to the image recording layer than the aluminum plate.
  • the anodized film has micropores extending from the surface on the image recording layer side in the depth direction, and the average diameter of the micropores on the surface of the anodized film is more than 10 nm and 100 nm or less.
  • the value of the lightness L * in the L * a * b * color system of the surface of the film on the image recording layer side is preferably 70 to 100.
  • FIG. 1 is a schematic cross-sectional view of one embodiment of the aluminum support 12a.
  • the aluminum support 12a has a laminated structure in which an aluminum plate 18 and an anodized film 20a of aluminum (hereinafter also simply referred to as "anodized film 20a") are laminated in this order.
  • the anodized film 20a in the aluminum support 12a is located closer to the image recording layer than the aluminum plate 18. That is, the lithographic printing plate precursor according to the present disclosure preferably has at least the anodized film, the image recording layer, and the water-soluble resin layer in this order on the aluminum plate.
  • the anodized film 20a is a film formed on the surface of the aluminum plate 18 by anodizing treatment, and this film is substantially perpendicular to the film surface, and each micropore 22a is extremely fine and uniformly distributed. Have.
  • the micropores 22a extend from the surface of the anodized film 20a on the image recording layer side (the surface of the anodized film 20a opposite to the aluminum plate 18 side) in the thickness direction (on the aluminum plate 18 side).
  • the average diameter (average opening diameter) of the micropores 22a in the anodized film 20a on the anodized film surface is preferably more than 10 nm and not more than 100 nm. Among them, 15 nm to 60 nm is more preferable, 20 nm to 50 nm is further preferable, and 25 to 40 nm is particularly preferable, from the viewpoint of balance between printing durability, stain resistance and image visibility.
  • the inner diameter of the pore may be wider or narrower than the surface layer. When the average diameter exceeds 10 nm, printing durability and image visibility are further excellent. Further, when the average diameter is 100 nm or less, printing durability is further excellent.
  • the diameter (diameter) of the micropores existing in the range is measured at 50 points and calculated as an arithmetic mean value.
  • the equivalent circle diameter is used.
  • the “equivalent circle diameter” is the diameter of a circle when the shape of the opening is assumed to be a circle having the same projected area as the projected area of the opening.
  • the depth of the micropores 22a is not particularly limited, but is preferably 10 nm to 3000 nm, more preferably 50 nm to 2000 nm, further preferably 300 nm to 1600 nm.
  • the depth is a value obtained by taking a photograph (150,000 times) of the cross section of the anodic oxide film 20a, measuring the depths of 25 or more micropores 22a, and averaging the depths.
  • the shape of the micropore 22a is not particularly limited, and is a substantially straight tube shape (substantially cylindrical shape) in FIG. 2, but may be a conical shape whose diameter decreases in the depth direction (thickness direction).
  • the shape of the bottom of the micropore 22a is not particularly limited, and may be curved (convex) or flat.
  • the micropores communicate with a large-diameter hole portion extending from the surface of the anodized film to a depth of 10 nm to 1,000 nm, and a bottom portion of the large-diameter hole portion.
  • a small diameter hole portion extending to a position of 20 nm to 2,000 nm, the average diameter of the large diameter hole portion on the surface of the anodized film is 15 nm to 150 nm, and the average diameter of the small diameter hole portion at the communicating position. Is preferably 13 nm or less (hereinafter, the support according to the above embodiment is also referred to as “support (2)”).
  • FIG. 2 is a schematic cross-sectional view of an embodiment of the aluminum support 12a different from that shown in FIG.
  • the support B is one mode of the aluminum support 12a shown in FIG.
  • the aluminum support 12b includes an aluminum plate 18 and an anodized film 20b having micropores 22b composed of large-diameter holes 24 and small-diameter holes 26.
  • the micropores 22b in the anodic oxide coating 20b communicate with the large-diameter holes 24 extending from the surface of the anodic oxide coating to a depth of 10 nm to 1000 nm (depth D: see FIG. 2) and the bottom of the large-diameter holes 24.
  • the small-diameter hole portion 26 extends from the communicating position to a position having a depth of 20 nm to 2000 nm.
  • the large diameter hole portion 24 and the small diameter hole portion 26 will be described in detail below.
  • the average diameter of the large-diameter holes 24 on the surface of the anodic oxide coating 20b is the same as the average diameter on the surface of the anodic oxide coating of the micropores 22a in the anodic oxide coating 20a described above, which is more than 10 nm and 100 nm or less, and the preferred range is also the same. Is.
  • the method of measuring the average diameter of the large-diameter holes 24 on the surface of the anodic oxide coating 20b is the same as the method of measuring the average diameter of the micropores 22a in the anodic oxide coating 20a on the surface of the anodic oxide coating.
  • the bottom of the large-diameter hole portion 24 is located at a depth of 10 nm to 1,000 nm (hereinafter, also referred to as depth D) from the surface of the anodized film. That is, the large-diameter hole 24 is a hole extending from the surface of the anodic oxide film to a position of 10 nm to 1,000 nm in the depth direction (thickness direction).
  • the depth is preferably 10 nm to 200 nm.
  • the depth is a value obtained by taking a photograph (150,000 times) of the cross section of the anodized film 20b, measuring the depths of 25 or more large-diameter hole portions 24, and averaging the depths.
  • the shape of the large-diameter hole portion 24 is not particularly limited, and examples thereof include a substantially straight tubular shape (substantially columnar shape) and a conical shape whose diameter decreases in the depth direction (thickness direction). preferable.
  • the small diameter hole portion 26 is a hole portion that communicates with the bottom portion of the large diameter hole portion 24 and extends further in the depth direction (thickness direction) from the communicating position.
  • the average diameter of the small-diameter holes 26 at the communicating position is preferably 13 nm or less. Especially, 11 nm or less is preferable and 10 nm or less is more preferable.
  • the lower limit is not particularly limited, but is often 5 nm or more.
  • the diameter (diameter) of (small-diameter hole portion) is measured and obtained as an arithmetic mean value. If the large-diameter holes are deep, the upper part of the anodized film 20b (the region where the large-diameter holes are located) is cut (for example, cut with argon gas), if necessary, and then the anodized film 20b.
  • the surface may be observed with the FE-SEM to determine the average diameter of the small diameter holes.
  • a circle equivalent diameter is used.
  • the “equivalent circle diameter” is the diameter of a circle when the shape of the opening is assumed to be a circle having the same projected area as the projected area of the opening.
  • the bottom portion of the small diameter hole portion 26 is located at a position extending 20 nm to 2000 nm further in the depth direction from the communication position with the large diameter hole portion 24.
  • the small diameter hole portion 26 is a hole portion that extends further in the depth direction (thickness direction) from the communication position with the large diameter hole portion 24, and the depth of the small diameter hole portion 26 is 20 nm to 2000 nm.
  • the depth is preferably 500 nm to 1500 nm.
  • the depth is a value obtained by taking a photograph (50,000 times) of the cross section of the anodic oxide film 20b, measuring the depths of 25 or more small diameter holes, and averaging the depths.
  • the shape of the small-diameter hole portion 26 is not particularly limited, and examples thereof include a substantially straight tubular shape (substantially cylindrical shape) and a conical shape whose diameter decreases in the depth direction, and the substantially straight tubular shape is preferable.
  • the lithographic printing plate precursor according to the present disclosure has an image recording layer formed on a support.
  • the image recording layer used in the present disclosure contains a specific infrared absorber, a polymerization initiator, and a polymerizable compound.
  • the image recording layer used in the present disclosure may further contain an acid color developing agent in order to confirm the exposed area before development.
  • the unexposed portion of the image recording layer can be removed by at least one selected from the group consisting of fountain solution and printing ink. .. The details of each component contained in the image recording layer will be described below.
  • the image recording layer contains the infrared absorbing agent represented by Formula 1-1 (specific infrared absorbing agent).
  • the infrared absorbent having a specific structure is likely to be decomposed because it has a specific structure, and it is considered that the infrared absorbent or its decomposed product accelerates the polymerization during the polymerization of the polymerizable compound. Therefore, in the image recording layer, the infrared absorbent having a specific structure, a polymerization initiator, and a polymerizable compound are used together to increase the polymerization efficiency, and a highly polar film can be obtained.
  • the printing plate precursor has excellent UV printing durability.
  • the specific infrared absorbing agent has a property of decomposing by heat or infrared exposure to generate a highly visible colored body.
  • “coloring” means that there is almost no absorption in the visible light region (400 or more and less than 750 nm) before heating or infrared exposure, and there is strong coloring after heating or infrared exposure, or the absorption has a short wavelength. It shows that it comes to have absorption in the visible light region. That is, the specific infrared absorber of the present disclosure is decomposed by heat or infrared exposure, and absorption is increased in the visible light region, or absorption is shortened and has absorption in the visible light region as compared with before heating or infrared exposure.
  • the specific infrared absorbing agent may be one that absorbs and decomposes at least a part of light in the infrared wavelength range (wavelength 750 nm to 1 mm, preferably 750 nm to 1,400 nm), but has a wavelength of 750 nm to 1,400 nm.
  • An infrared absorber having a maximum absorption in the region is preferable.
  • the specific infrared absorbing agent is preferably a compound which decomposes by heat or infrared exposure to form a compound having a maximum absorption wavelength in the range of 500 nm to 600 nm.
  • the above-mentioned specific infrared absorbing agent is preferably an infrared absorbing dye which is decomposed by electron transfer caused by infrared exposure.
  • decomposes by electron transfer means that an electron excited from a HOMO (highest occupied molecular orbital) of a specific infrared absorbent to a LUMO (lowest unoccupied molecular orbital) by infrared exposure is an electron accepting group (LUMO It means that intramolecular electron transfer to a group (having a near electric potential) occurs, which causes decomposition.
  • the coloring mechanism of the specific infrared absorbing agent is the R 1 -L bond in Formula 1-1, that is, the R 1 in Formula 2 upon exposure to heat or infrared rays. It is considered that the Z 1 —O bond is cleaved and L in Formula 1-1 becomes ⁇ O, ⁇ S, or NR 10 to produce a chromophore. Further, it is considered that R 1 in Formula 1-1, that is, R Z in Formula 2, is eliminated to contribute to the polymerizable compound contained in the image recording layer and enhance the polymerization efficiency. The present inventors presume that the color is developed by changing the electronic structure in the electron-conjugated system of the mother nucleus structure of the specific infrared absorbent.
  • R 1 represents a group represented by Formula 2, and R 11 to R 18 each independently represent a hydrogen atom, a halogen atom, —Ra, —OR b , —SR c or —NR d R. represents e, Ra ⁇ Re each independently represent a hydrocarbon group, a 1, a 2 and a plurality of R 11 ⁇ R 18 may form a monocyclic or polycyclic linked is, a 1 and A 2 each independently represents an oxygen atom, a sulfur atom or a nitrogen atom, and n 11 and n 12 each independently represent an integer of 0 to 5, provided that the total of n 11 and n 12 is 2 or more.
  • N 13 and n 14 each independently represent 0 or 1
  • L represents an oxygen atom, a sulfur atom or —NR 10 —
  • R 10 represents a hydrogen atom, an alkyl group or an aryl group
  • Za represents a charge. Represents a counterion that neutralizes.
  • R 11 to R 18 are preferably each independently a hydrogen atom, —R a , —OR b , —SR c or —NR d R e .
  • the hydrocarbon group for R a to R e is preferably a hydrocarbon group having 1 to 30 carbon atoms, more preferably a hydrocarbon group having 1 to 15 carbon atoms, and still more preferably a hydrocarbon group having 1 to 10 carbon atoms.
  • the hydrocarbon group may have a straight chain structure, a branched structure, or a ring structure.
  • R 11 to R 14 in Formula 1-1 are each independently preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom. Further, R 11 and R 13 bonded to the carbon atom bonded to L and the carbon atom bonded to L are preferably an alkyl group, and more preferably linked to each other to form a ring.
  • the formed ring is preferably a 5-membered ring or a 6-membered ring, more preferably a 5-membered ring.
  • R 12 bound to the carbon atom to which A 1 + is bound and R 14 bound to the carbon atom to which A 2 is bound are preferably linked to R 15 and R 17 , respectively, to form a ring.
  • R 15 in Formula 1-1 is preferably a hydrocarbon group. Further, it is preferable that R 15 and R 12 bonded to the carbon atom to which A 1 + is bonded are linked to form a ring.
  • the ring formed is preferably an indolium ring, a pyrylium ring, a thiopyrylium ring, a benzoxazoline ring or a benzimidazoline ring, and more preferably an indolium ring from the viewpoint of color development.
  • R 17 in Formula 1-1 is preferably a hydrocarbon group. Further, it is preferable that R 17 and R 14 bonded to the carbon atom to which A 2 is bonded are linked to form a ring.
  • the ring formed is preferably an indole ring, a pyran ring, a thiopyran ring, a benzoxazole ring, or a benzimidazole ring, and more preferably an indole ring from the viewpoint of color development.
  • R 15 and R 17 in Formula 1-1 are preferably the same group, and when they form a ring, they preferably form the same ring.
  • R 16 and R 18 in Formula 1-1 are preferably the same group. Further, from the viewpoint of improving the water solubility of the compound represented by Formula 1-1, R 16 and R 18 are each independently preferably a alkyl group having a (poly) oxyalkylene group or an alkyl group having an anion structure, An alkyl group having an alkoxyalkyl group, a carboxylate group or a sulfonate group is more preferable, and an alkyl group having a sulfonate group at the terminal is further preferable. As the alkyl group, an alkyl group having 1 to 10 carbon atoms is preferable, and an alkyl group having 1 to 4 carbon atoms is more preferable.
  • the counter cation of the above anion structure may be a cation or A 1 + that may be contained in R 1 -L in formula 1-1, or may be an alkali metal cation or an alkaline earth metal cation.
  • the counter cation of the sulfonate group may be a cation or A 1 + which may be contained in R 1 -L in formula 1-1, or may be an alkali metal cation or an alkaline earth metal cation.
  • R 16 and R 18 are respectively Independently, an alkyl group or an alkyl group having an aromatic ring is preferable.
  • the alkyl group is preferably an alkyl group having 1 to 10 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms, and further preferably a methyl group or an ethyl group.
  • the alkyl group having an aromatic ring is preferably an alkyl group having an aromatic ring at the terminal, more preferably a 2-phenylethyl group, a 2-naphthalenylethyl group or a 2- (9-anthracenyl) ethyl group.
  • n 11 and n 12 are preferably the same integer of 0 to 5, more preferably 1 to 3, further preferably 1 or 2, and particularly preferably 2.
  • a 1 and A 2 in Formula 1-1 each independently represent an oxygen atom, a sulfur atom or a nitrogen atom, and a nitrogen atom is preferable.
  • a 1 and A 2 in Formula 1-1 are preferably the same atom.
  • Za in Formula 1-1 represents a counter ion that neutralizes charge.
  • anion species include sulfonate ion, carboxylate ion, tetrafluoroborate ion, hexafluorophosphate ion, p-toluenesulfonate ion, perchlorate ion, and hexafluoroantimonate ion.
  • Hexafluorophosphate ion Is preferred.
  • alkali metal ions alkaline earth metal ions, ammonium ions, pyridinium ions, sulfonium ions and the like can be mentioned, sodium ions, potassium ions, ammonium ions, pyridinium ions or sulfonium ions are preferred, sodium ions, More preferred is potassium ion or ammonium ion.
  • R 11 to R 18 and R 1 -L may have an anion structure or a cation structure, and if all of R 11 to R 18 and R 1 -L are charge neutral groups, Za Is a monovalent counter anion, but Za can also be a counter cation when, for example, R 11 to R 18 and R 1 -L have two or more anionic structures. Further, if the compound represented by Formula 1-1 (specific infrared absorber) has a charge-neutral structure as a whole of the compound, Za does not exist.
  • the specific infrared absorbing agent is preferably a cyanine dye that decomposes by infrared exposure from the viewpoint of color developability and UV printing durability of the lithographic printing plate obtained.
  • the cyanine dye that decomposes by infrared exposure is more preferably the cyanine dye represented by Formula 1 above from the viewpoints of color developability and UV printing durability of the resulting lithographic printing plate.
  • the cyanine dye represented is more preferred.
  • R 1 represents a group represented by Formula 2
  • R 2 and R 3 each independently represent a hydrogen atom or an alkyl group
  • R 2 and R 3 are linked to each other to form a ring.
  • Ar 1 and Ar 2 each independently represent a group forming a benzene ring or a naphthalene ring
  • Y 1 and Y 2 are each independently oxygen atom, sulfur atom, —NR 0 — or dialkylmethylene.
  • R 0 represents a hydrogen atom, an alkyl group or an aryl group
  • R 4 and R 5 each independently represent an alkyl group, a —CO 2 M group or a —PO 3 M 2 group
  • M is a hydrogen atom.
  • a sodium atom, a potassium atom or an onium group, R 6 to R 9 each independently represent a hydrogen atom or an alkyl group
  • L represents an oxygen atom, a sulfur atom or —NR 10 —
  • R 10 represents a hydrogen atom.
  • An alkyl group or It represents an aryl group
  • Za represents a counter ion that neutralizes charge.
  • the alkyl group for R 2 to R 9 and R 0 is preferably an alkyl group having 1 to 30 carbon atoms, more preferably an alkyl group having 1 to 15 carbon atoms, and an alkyl group having 1 to 10 carbon atoms. Is more preferable.
  • the alkyl group may have a straight chain structure, a branched structure, or a ring structure.
  • eicosyl group isopropyl group, isobutyl group, s-butyl group, tert-butyl group, isopentyl group, neopentyl group, 1-methylbutyl group, isohexyl group, 2-ethylhexyl group, 2-methylhexyl group, cyclohexyl group, cyclopentyl group And a 2-norbornyl group.
  • alkyl groups a methyl group, an ethyl group, a propyl group or a butyl group is preferable.
  • the above alkyl group may have a substituent.
  • substituents include an alkoxy group, aryloxy group, amino group, alkylthio group, arylthio group, halogen atom, carboxy group, carboxylate group, sulfo group, sulfonate group, alkyloxycarbonyl group, aryloxycarbonyl group, and The group etc. which combined these are mentioned.
  • the aryl group for R 0 is preferably an aryl group having 6 to 30 carbon atoms, more preferably an aryl group having 6 to 20 carbon atoms, and further preferably an aryl group having 6 to 12 carbon atoms.
  • the aryl group may have a substituent. Examples of the substituent include an alkyl group, an alkoxy group, an aryloxy group, an amino group, an alkylthio group, an arylthio group, a halogen atom, a carboxy group, a carboxylate group, a sulfo group, a sulfonate group, an alkyloxycarbonyl group and an aryloxycarbonyl group. , And groups combining these.
  • aryl groups a phenyl group, a p-methoxyphenyl group, a p-dimethylaminophenyl group or a naphthyl group is preferable.
  • R 2 and R 3 are preferably linked to each other to form a ring.
  • R 2 and R 3 are linked to form a ring, a 5-membered ring or a 6-membered ring is preferable, and a 5-membered ring is particularly preferable.
  • Y 1 and Y 2 each independently represent an oxygen atom, a sulfur atom, —NR 0 — or a dialkylmethylene group, preferably —NR 0 — or a dialkylmethylene group, and more preferably a dialkylmethylene group.
  • R 0 represents a hydrogen atom, an alkyl group or an aryl group, and an alkyl group is preferable.
  • the alkyl group represented by R 4 or R 5 may be substituted alkyl.
  • Examples of the substituted alkyl group represented by R 4 or R 5 include groups represented by any of the following formulas (a1) to (a4).
  • R W0 represents an alkylene group having 2 to 6 carbon atoms
  • W represents a single bond or an oxygen atom
  • n W1 represents an integer of 1 to 45
  • R W1 represents carbon.
  • R W5 represents an alkyl group having 1 to 12 carbon atoms
  • R W2 to R W4 each independently represent a single bond or 1 carbon atom
  • M represents a hydrogen atom, a sodium atom, a potassium atom or an onium group.
  • alkylene group represented by R W0 in the formula (a1) examples include an ethylene group, an n-propylene group, an isopropylene group, an n-butylene group, an isobutylene group, an n-pentylene group, an isopentylene group, and an n- Examples thereof include a hexyl group and an isohexyl group, with an ethylene group, an n-propylene group, an isopropylene group and an n-butylene group being preferred, and an n-propylene group being particularly preferred.
  • n W1 is preferably 1 to 10, more preferably 1 to 5, and particularly preferably 1 to 3.
  • alkyl group represented by R W1 examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group.
  • the alkyl group represented by R W5 is the same as the alkyl group represented by R W1 and the preferred embodiments are also the same as the preferred embodiments of the alkyl group represented by R W1 .
  • alkylene group represented by R W2 to R W4 examples include methylene group, ethylene group, n-propylene group, isopropylene group, n-butylene group, isobutylene group. , N-pentylene group, isopentylene group, n-hexyl group, isohexyl group, n-octylene group, n-dodecylene group and the like, ethylene group, n-propylene group, isopropylene group, n-butylene group are preferable, An ethylene group and an n-propylene group are particularly preferable.
  • two existing Ms may be the same or different.
  • examples of the onium group represented by M include an ammonium group, an iodonium group, a phosphonium group and a sulfonium group.
  • the substituted alkyl group represented by R 4 or R 5 is , from the viewpoint of color developability and UV printing durability of the lithographic printing plate obtained,
  • the group represented by the formula (a1) or the formula (a4) (-R w4 SO 3 M group) is preferable, and the group represented by the formula (a4) is more preferable.
  • each of R 4 and R 5 is preferably an unsubstituted alkyl group.
  • R 4 and R 5 are preferably the same group.
  • R 6 to R 9 each independently represent a hydrogen atom or an alkyl group, and preferably a hydrogen atom.
  • Ar 1 and Ar 2 each independently represent a group forming a benzene ring or a naphthalene ring. The benzene ring and naphthalene ring may have a substituent.
  • substituent examples thereof include groups, phosphonic acid groups, and groups in which these are combined.
  • the substituent is preferably an alkyl group.
  • Ar 1 and Ar 2 are each independently, A naphthalene ring, or a group forming a benzene ring having an alkyl group or an alkoxy group as a substituent is preferable, a naphthalene ring, or a group forming a benzene ring having an alkoxy group as a substituent is more preferable, a naphthalene ring, or A group forming a benzene ring having a methoxy group as a substituent is particularly preferable.
  • Ar 1 or Ar 2 is preferably a group forming a group represented by the following formula (b1).
  • R 19 represents an alkyl group having 1 to 12 carbon atoms.
  • n3 represents an integer of 1 to 4. * Represents a binding site.
  • Za represents a counter ion for neutralizing the electric charge.
  • Za represents an anionic species, examples thereof include a sulfonate ion, a carboxylate ion, a tetrafluoroborate ion, a hexafluorophosphate ion, a p-toluenesulfonate ion, a perchlorate ion, and a hexafluoroantimonate ion.
  • Phosphate ions are preferred.
  • Za represents a cationic species
  • examples thereof include an alkali metal ion, an alkaline earth metal ion, an ammonium ion, a pyridinium ion or a sulfonium ion, and a sodium ion
  • a potassium ion, an ammonium ion, a pyridinium ion or a sulfonium ion is preferable, and sodium is used.
  • Ions, potassium ions or ammonium ions are more preferred.
  • R 1 to R 9 , R 0 , Ar 1 , Ar 2 , Y 1 and Y 2 may have an anion structure or a cation structure, and R 1 to R 9 , R 0 , Ar 1 , Ar 2 and When Y 1 and Y 2 are all charge-neutral groups, Za is a monovalent counter anion, and for example, R 1 to R 9 , R 0 , Ar 1 , Ar 2 , Y 1 and When Y 2 has two or more anionic structures, Za can also be a counter cation.
  • Group represented by Formula 2 represented by R 1 In Formula 1-1 and Formula 1-2, the group represented by Formula 2 and represented by R 1 will be described below.
  • the group represented by Formula 2 represented by R 1 is preferably a group in which the R Z —O bond in Formula 2 is cleaved by heat or infrared exposure.
  • R Z represents an alkyl group
  • the wavy line represents a binding site with the group represented by L in Formula 1-1 or Formula 1-2.
  • the alkyl group represented by R Z is the same as the preferred embodiments of the alkyl group for R 2 to R 9 and R 0 described above. From the viewpoints of color developability and UV printing durability of the lithographic printing plate obtained, the alkyl group is preferably a secondary alkyl group or a tertiary alkyl group, and is a tertiary alkyl group. Is preferred.
  • the alkyl group is preferably an alkyl group having 1 to 8 carbon atoms, more preferably a branched alkyl group having 3 to 10 carbon atoms, and 3 to 6 carbon atoms. Is more preferably a branched chain alkyl group, particularly preferably an isopropyl group or a tert-butyl group, and most preferably a t-butyl group.
  • L in Formula 1-1 or Formula 1-2 is preferably an oxygen atom from the viewpoint of UV printing durability.
  • Specific examples of the group represented by R 1 in formula 1-1 or formula 1-2 are shown below, but the present disclosure is not limited thereto.
  • ⁇ represents a binding site with L in formula 1-1 or formula 1-2.
  • L represents a sulfur atom or —NR 10 — and R 10 represents a hydrogen atom, an alkyl group or an aryl group, from the viewpoint of improving UV printing durability.
  • the compound represented by Formula 1-1 or Formula 1-2 can be synthesized by applying a known method.
  • the compound represented by the formula 1-1 is a compound according to the following scheme 2 when L is —NR 10 — in the formula 1-1 and R 1 bonded to N is a group represented by the above formula 2.
  • L is —NR 10 — in the formula 1-1
  • R 1 bonded to N is a group represented by the above formula 2.
  • Scheme 2 below, the respective symbols are the same as those in Formula 1-1, Formula 1-2 and Formula 2.
  • a synthetic scheme represented by the following Formula (S1) is preferable.
  • DMAP represents N, N-dimethylamino-4-pyridine
  • AcONa represents sodium acetate
  • Me represents a methyl group.
  • R Z represents a group corresponding to each moiety in Formula 2.
  • the specific infrared absorbing agents may be used alone or in combination of two or more.
  • the content of the specific infrared absorbing agent in the image recording layer is preferably 0.1% by mass to 95% by mass, more preferably 1% by mass to 50% by mass, based on the total mass of the image recording layer. 40% by mass is more preferable.
  • the specific infrared absorbing agent itself has excellent infrared absorbing performance, and therefore functions well as an infrared absorbing agent. Therefore, when the specific infrared absorbing agent is used in the image recording layer of the planographic printing plate precursor, it is actually necessary to use an infrared absorbing agent other than the specific infrared absorbing agent (hereinafter, also referred to as "other infrared absorbing agent"). However, the image recording layer may contain other infrared absorbing agent.
  • the image recording layer may contain an infrared absorbing agent other than the specific infrared absorbing agent.
  • Other infrared absorbers include pigments and dyes.
  • dyes to be used as the infrared absorber commercially available dyes and known dyes described in documents such as "Handbook of Dyes” (edited by the Society of Synthetic Organic Chemistry, published in 1970) can be used.
  • azo dyes metal complex salt azo dyes, pyrazolone azo dyes, naphthoquinone dyes, anthraquinone dyes, phthalocyanine dyes, carbonium dyes, quinone imine dyes, methine dyes, cyanine dyes, squarylium dyes, pyrylium salts, metal thiolate complex dyes, etc. Is mentioned.
  • dyes particularly preferable are cyanine dyes, squarylium dyes, pyrylium salts, nickel thiolate complexes, and indolenine cyanine dyes.
  • cyanine dyes and indolenine cyanine dyes can be mentioned. Of these, cyanine dyes are particularly preferable.
  • cyanine dye examples include compounds described in paragraphs 0017 to 0019 of JP 2001-133969 A, paragraphs 0016 to 0021 of JP 2002-023360 A, and paragraphs 0012 to 0037 of JP 2002-040638 A.
  • the compounds described in paragraphs 0008 to 0009 of JP-A-5-5005 and paragraphs 0022 to 0025 of JP-A 2001-222101 can also be preferably used.
  • the compounds described in paragraphs 0072 to 0076 of JP 2008-195018 are preferable.
  • infrared absorbers may be used alone or in combination of two or more. Further, a pigment and a dye may be used together as an infrared absorber.
  • the content of the other infrared absorbing agent in the image recording layer is preferably less than the content of the specific infrared absorbing agent from the viewpoint of color developability and UV printing durability of the lithographic printing plate obtained, It is more preferable that the image recording layer does not contain any other infrared absorbing agent.
  • the image recording layer used in the present disclosure preferably further contains a binder polymer, and more preferably contains a binder polymer having a constitutional unit formed of an aromatic vinyl compound (hereinafter, also referred to as “specific binder polymer”). preferable.
  • the binder polymer is a binder resin that is not in the form of particles, and the polymer particles described below are not included in the binder polymer in the present disclosure.
  • the specific binder polymer preferably further has a structural unit formed of an acrylonitrile compound.
  • the aromatic vinyl compound contained in the specific binder polymer may be a compound having a structure in which a vinyl group is bonded to an aromatic ring, but examples thereof include a styrene compound and a vinylnaphthalene compound, and a styrene compound is preferable, and styrene is more preferable. preferable.
  • styrene compound examples include styrene, p-methylstyrene, p-methoxystyrene, ⁇ -methylstyrene, p-methyl- ⁇ -methylstyrene, ⁇ -methylstyrene and p-methoxy- ⁇ -methylstyrene.
  • Styrene is preferred.
  • vinylnaphthalene compound examples include 1-vinylnaphthalene, methyl-1-vinylnaphthalene, ⁇ -methyl-1-vinylnaphthalene, 4-methyl-1-vinylnaphthalene and 4-methoxy-1-vinylnaphthalene. -Vinylnaphthalene is preferred.
  • constitutional unit formed by the aromatic vinyl compound is preferably a constitutional unit represented by the following formula A1.
  • R A1 and R A2 each independently represent a hydrogen atom or an alkyl group
  • Ar represents an aromatic ring group
  • R A3 represents a substituent
  • n represents an integer not greater than the maximum number of substituents of Ar. ..
  • R A1 and R A2 are each independently preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom or a methyl group, and both are hydrogen atoms. Is more preferable.
  • Ar is preferably a benzene ring or a naphthalene ring, more preferably a benzene ring.
  • R A3 is preferably an alkyl group or an alkoxy group, more preferably an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and a methyl group or a methoxy group. Is more preferable. In the formula A1, when the R A3 there are a plurality, plural of R A3 may be the same or may be different. In formula A1, n is preferably an integer of 0 to 2, more preferably 0 or 1, and even more preferably 0.
  • the content of the constituent unit formed by the aromatic vinyl compound in the specific binder polymer is preferably 15% by mass to 85% by mass, and 30% by mass to 70% by mass, based on the total mass of the specific binder polymer. More preferably.
  • the specific binder polymer preferably further has a structural unit formed of an acrylonitrile compound, from the viewpoints of developability, color developability, and UV printing durability of the lithographic printing plate obtained.
  • the acrylonitrile compound include (meth) acrylonitrile, and acrylonitrile is preferable.
  • constitutional unit formed by the acrylonitrile compound a constitutional unit represented by the following formula B1 is preferably exemplified.
  • R B1 represents a hydrogen atom or an alkyl group.
  • R B1 is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom or a methyl group, and further preferably a hydrogen atom.
  • the content of the structural unit formed by the acrylonitrile compound in the specific binder polymer is preferably 5% by mass to 85% by mass, and 8% by mass to 70% by mass with respect to the total mass of the specific binder polymer. Is more preferable.
  • the specific binder polymer preferably further has a structural unit formed of an N-vinyl heterocyclic compound.
  • N-vinyl heterocyclic compounds include N-vinylpyrrolidone, N-vinylcarbazole, N-vinylpyrrole, N-vinylphenothiazine, N-vinylsuccinimide, N-vinylphthalimide, N-vinylcaprolactam, and N- Examples thereof include vinylimidazole, and N-vinylpyrrolidone is preferable.
  • a structural unit formed by the N-vinyl heterocyclic compound a structural unit represented by the following formula C1 is preferably exemplified.
  • Ar N represents a heterocyclic structure containing a nitrogen atom, a nitrogen atom in Ar N is bonded to the carbon atoms indicated by *.
  • the heterocyclic structure represented by Ar N is preferably a pyrrolidone ring, a carbazole ring, a pyrrole ring, a phenothiazine ring, a succinimide ring, a phthalimide ring, a caprolactam ring, or an imidazole ring, and a pyrrolidone ring. Is more preferable.
  • the heterocyclic structure represented by Ar N may have a known substituent.
  • the content of the structural unit formed by the N-vinyl heterocyclic compound in the specific binder polymer is preferably 5% by mass to 70% by mass, and 10% by mass to 60% by mass, based on the total mass of the specific binder polymer. % Is more preferable.
  • the specific binder polymer may further have a structural unit having an ethylenically unsaturated group.
  • the ethylenically unsaturated group is not particularly limited, and examples thereof include a vinyl group, an allyl group, a vinylphenyl group, a (meth) acrylamide group, a (meth) acryloyloxy group, and the like. ) It is preferably an acryloyloxy group.
  • the constitutional unit having an ethylenically unsaturated group can be introduced into the specific binder polymer by polymer reaction or copolymerization.
  • a method of reacting a polymer having a structural unit having a carboxy group such as methacrylic acid with a compound having an epoxy group and an ethylenically unsaturated group (eg, glycidyl methacrylate), a hydroxy group It can be introduced by a method of reacting a compound having an isocyanate group and an ethylenically unsaturated group (such as 2-isocyanatoethylmethacrylate) with a polymer having a constitutional unit having a group having active hydrogen such as ..
  • the constitutional unit having an ethylenically unsaturated group may be obtained by reacting a compound having a constitutional unit having an epoxy group such as glycidyl (meth) acrylate with a compound having a carboxy group and an ethylenically unsaturated group. It may be incorporated into the specific binder polymer by a method. Furthermore, the constitutional unit having an ethylenically unsaturated group may be introduced into the specific binder polymer by using, for example, a monomer containing a partial structure represented by the following formula d1 or the following formula d2.
  • an ethylenically unsaturated group is formed by a elimination reaction using a basic compound with respect to the partial structure represented by the following formula d1 or the following formula d2.
  • a basic compound with respect to the partial structure represented by the following formula d1 or the following formula d2.
  • R d represents a hydrogen atom or an alkyl group
  • a d represents a halogen atom
  • X d represents —O— or —NR N —
  • R N represents a hydrogen atom or an alkyl group.
  • R d is preferably a hydrogen atom or a methyl group.
  • a d is preferably a chlorine atom, a bromine atom, or an iodine atom.
  • X d is preferably —O—.
  • R N is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and more preferably a hydrogen atom.
  • constitutional unit having an ethylenically unsaturated group examples include constitutional units represented by the following formula D1.
  • L D1 represents a single bond or a divalent linking group
  • L D2 represents a m + 1 valent linking group
  • X D1 and X D2 each independently represent —O— or —NR N —
  • R N represents a hydrogen atom or an alkyl group
  • R D1 and R D2 each independently represent a hydrogen atom or a methyl group
  • m represents an integer of 1 or more.
  • L D1 is preferably a single bond.
  • L D1 represents a divalent linking group, an alkylene group, an arylene group or a divalent group in which two or more of these are bonded is preferable, and an alkylene group having 2 to 10 carbon atoms or a phenylene group is more preferable.
  • L D2 is preferably a group represented by any one of Formula D2 to Formula D6 below.
  • both X D1 and X D2 are preferably —O—.
  • R N is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and more preferably a hydrogen atom.
  • R D1 is preferably a methyl group.
  • at least one of m R D2 is preferably a methyl group.
  • m is preferably an integer of 1 to 4, more preferably 1 or 2, and even more preferably 1.
  • L D3 to L D7 represent a divalent linking group
  • L D5 and L D6 may be different from each other
  • * represents a binding site with X D1 in formula D1
  • a wavy line portion Represents a binding site with X D2 in formula D1.
  • L D3 is preferably an alkylene group, an arylene group, or a group in which two or more thereof are bonded, and an alkylene group having 1 to 10 carbon atoms, a phenylene group, or a group in which two or more of these are bonded. More preferable.
  • L D4 is preferably an alkylene group, an arylene group, or a group in which two or more thereof are bonded, and an alkylene group having 1 to 10 carbon atoms, a phenylene group, or a group in which two or more thereof are bonded. More preferable.
  • L D5 is preferably an alkylene group, an arylene group, or a group in which two or more thereof are bonded, and is an alkylene group having 1 to 10 carbon atoms, a phenylene group, or a group in which two or more of these are bonded. More preferable.
  • L D6 is preferably an alkylene group, an arylene group, or a group in which these are bonded two or more, and is an alkylene group having 1 to 10 carbon atoms, a phenylene group, or a group in which two or more of these are bonded. More preferable.
  • L D7 is preferably an alkylene group, an arylene group, or a group in which two or more thereof are bonded, and is an alkylene group having 1 to 10 carbon atoms, a phenylene group, or a group in which two or more of these are bonded. More preferable.
  • constitutional unit having an ethylenically unsaturated group examples include a hydrogen atom or a methyl group.
  • the content of the constituent unit having an ethylenically unsaturated group in the specific binder polymer is preferably 5% by mass to 60% by mass, and preferably 10% by mass to 30% by mass, based on the total mass of the specific binder polymer. Is more preferable.
  • the specific binder polymer may contain a structural unit having an acidic group, but from the viewpoint of on-press developability and ink receptivity, it is preferable that the specific binder polymer does not contain a structural unit having an acidic group.
  • the content of the structural unit having an acidic group in the specific binder polymer is preferably 20% by mass or less, more preferably 10% by mass or less, and further preferably 5% by mass or less. preferable.
  • the lower limit of the content is not particularly limited and may be 0% by mass.
  • the acid value of the specific binder polymer is preferably 160 mgKOH / g or less, more preferably 80 mgKOH / g or less, and further preferably 40 mgKOH / g or less.
  • the lower limit of the acid value is not particularly limited and may be 0 mgKOH / g. In the present disclosure, the acid value is determined by the measuring method according to JIS K0070: 1992.
  • the specific binder polymer may contain a structural unit containing a hydrophobic group from the viewpoint of ink receptivity.
  • the hydrophobic group include an alkyl group, an aryl group and an aralkyl group.
  • the structural unit containing a hydrophobic group a structural unit formed by an alkyl (meth) acrylate compound, an aryl (meth) acrylate compound or an aralkyl (meth) acrylate compound is preferable, and a structural unit formed by an alkyl (meth) acrylate compound is preferable. Are more preferred.
  • the alkyl group in the above alkyl (meth) acrylate compound preferably has 1 to 10 carbon atoms.
  • the alkyl group may be linear or branched, and may have a cyclic structure.
  • Examples of the alkyl (meth) acrylate compound include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate and dicyclopentanyl (meth) acrylate. Is mentioned.
  • the aryl group in the aryl (meth) acrylate compound preferably has 6 to 20 carbon atoms, and more preferably a phenyl group. Further, the aryl group may have a known substituent.
  • Preferable examples of the aryl (meth) acrylate compound include phenyl (meth) acrylate.
  • the carbon number of the alkyl group in the aralkyl (meth) acrylate compound is preferably 1-10.
  • the alkyl group may be linear or branched, and may have a cyclic structure.
  • the aryl group in the aralkyl (meth) acrylate compound preferably has 6 to 20 carbon atoms, and more preferably a phenyl group.
  • Preferred examples of the aralkyl (meth) acrylate compound include benzyl (meth) acrylate.
  • the content of the structural unit having a hydrophobic group in the specific binder polymer is preferably 5% by mass to 50% by mass, and preferably 10% by mass to 30% by mass, based on the total mass of the specific binder polymer. More preferable.
  • the specific binder polymer may include a structural unit having a hydrophilic group from the viewpoint of improving UV printing durability, chemical resistance, and on-press development property.
  • a hydrophilic group —OH, —CN, —CONR 1 R 2 , —NR 2 COR 1 (R 1 and R 2 each independently represent a hydrogen atom, an alkyl group, an alkenyl group or an aryl group. R 1 and R 2 may combine with each other to form a ring.) —NR 3 R 4 , —N + R 3 R 4 R 5 X ⁇ (R 3 to R 5 each independently have a carbon number.
  • X ⁇ represents a counter anion
  • groups represented by the following formula PO and the like.
  • hydrophilic groups a group represented by —OH, —CONR 1 R 2 or formula PO is preferable, a group represented by —OH or formula PO is more preferable, and —OH is further preferable.
  • L P each independently represents an alkylene group
  • R P represents a hydrogen atom or an alkyl group
  • n represents an integer of 1 to 100.
  • L P is preferably each independently an ethylene group, a 1-methylethylene group or a 2-methylethylene group, and more preferably an ethylene group.
  • R P is preferably a hydrogen atom or an alkyl group having 1 to 18 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and a hydrogen atom or 1 to 4 carbon atoms. Is more preferable, and a hydrogen atom or a methyl group is particularly preferable.
  • n is preferably an integer of 1 to 10, more preferably an integer of 1 to 4.
  • constitutional unit having a hydrophilic group a constitutional unit formed by a hydroxyalkyl (meth) acrylate compound is preferable, and a constitutional unit formed by a hydroxyethyl (meth) acrylate compound is more preferable.
  • the content of the structural unit having a hydrophilic group in the specific binder polymer is preferably 5% by mass to 60% by mass, and more preferably 10% by mass to 30% by mass, based on the total mass of the specific binder polymer. More preferable.
  • the specific binder polymer may further contain other structural units.
  • a structural unit other than the above structural units can be contained without particular limitation, and examples thereof include structural units formed of an acrylamide compound, a vinyl ether compound, and the like.
  • the acrylamide compound include (meth) acrylamide, N-methyl (meth) acrylamide, N-ethyl (meth) acrylamide, N-propyl (meth) acrylamide, N-butyl (meth) acrylamide, N, N′-dimethyl.
  • Examples thereof include (meth) acrylamide, N, N′-diethyl (meth) acrylamide, N-hydroxyethyl (meth) acrylamide, N-hydroxypropyl (meth) acrylamide, N-hydroxybutyl (meth) acrylamide and the like.
  • the vinyl ether compound include methyl vinyl ether, ethyl vinyl ether, propyl vinyl ether, n-butyl vinyl ether, tert-butyl vinyl ether, 2-ethylhexyl vinyl ether, n-nonyl vinyl ether, lauryl vinyl ether, cyclohexyl vinyl ether, cyclohexyl methyl vinyl ether, 4-methylcyclohexyl vinyl ether.
  • the content of the other constitutional units in the specific binder polymer is preferably 5% by mass to 50% by mass, more preferably 10% by mass to 30% by mass, based on the total mass of the specific binder polymer.
  • the method for producing the specific binder polymer is not particularly limited, and the specific binder polymer can be produced by a known method.
  • Known compound at least one compound selected from the group consisting of the compound used for forming the structural unit having the hydrophobic group, and the compound used for forming the other structural unit. It is obtained by polymerizing.
  • the weight average molecular weight of the specific binder polymer is preferably 3,000 to 300,000, and more preferably 5,000 to 100,000.
  • the content ratio of each structural unit can be appropriately changed according to the preferable range of the content of each structural unit described above.
  • the weight average molecular weight of each compound shown in the above specific examples can be appropriately changed according to the preferable range of the weight average molecular weight of the above-mentioned specific binder polymer.
  • the image recording layer may contain one specific binder polymer alone, or may use two or more specific binder polymers in combination.
  • the content of the specific binder polymer with respect to the total mass of the image recording layer is preferably 5% by mass or more and 95% by mass or less, more preferably 7% by mass or more and 80% by mass or less, and 10% by mass or more and 60% by mass or less. More preferable.
  • the polymerization initiator is a compound that initiates and accelerates the polymerization of the polymerizable compound.
  • a known thermal polymerization initiator a compound having a bond having a small bond dissociation energy, a photopolymerization initiator, an electron-accepting polymerization initiator described below, an electron-donating polymerization initiator described below, etc. may be used.
  • the radical polymerization initiators described in paragraphs 0092 to 0106 of JP-A-2014-104631 can be used.
  • a preferable compound is an onium salt compound. Among them, iodonium salts and sulfonium salts are particularly preferable. Preferred specific compounds of the respective salts are the same as the compounds described in paragraphs 0104 to 0106 of JP-A-2014-104631.
  • the content of the polymerization initiator is preferably 0.1% by mass to 50% by mass, more preferably 0.5% by mass to 30% by mass, and 0.8% by mass to 20% with respect to the total mass of the image recording layer. Mass% is particularly preferred. Within this range, better sensitivity and better stain resistance of the non-image area during printing can be obtained.
  • the polymerization initiator may be used singly or in combination of two or more, but the polymerization initiator in the image recording layer is not limited to color forming properties, color formation after exposure with time, developability, and From the viewpoint of UV printing durability of the resulting lithographic printing plate precursor, it is preferable that the lithographic printing plate precursor contains at least one polymerization initiator selected from the group consisting of an electron-donating polymerization initiator and an electron-accepting polymerization initiator. It is more preferable to include a donor type polymerization initiator and an electron accepting type polymerization initiator.
  • the above-mentioned polymerization initiator is an electron-donating polymerization initiator and an electron-accepting polymerization initiator from the viewpoints of color developability, color developability after exposure, developability, and UV printing durability in the lithographic printing plate precursor obtained. It is preferred that and include a compound formed by forming a counter salt.
  • the image recording layer contains an electron-donating polymerization initiator as the polymerization initiator from the viewpoints of color developability, color developability after exposure with time, developability, and UV printing durability of the resulting lithographic printing plate precursor. Is preferred.
  • the electron-donating polymerization initiator is considered to contribute to the improvement of chemical resistance and printing durability of the lithographic printing plate. Examples of the electron-donating polymerization initiator include the following 5 types.
  • (I) Alkyl or arylate complex An active radical is considered to be generated by the oxidative cleavage of a carbon-hetero bond. Specific examples include borate compounds.
  • (Ii) Aminoacetic acid compound It is considered that the C—X bond on the carbon adjacent to the nitrogen is cleaved by oxidation to generate an active radical.
  • X is preferably a hydrogen atom, a carboxy group, a trimethylsilyl group or a benzyl group. Specific examples thereof include N-phenylglycines (which may have a substituent on the phenyl group), N-phenyliminodiacetic acid (which may have a substituent on the phenyl group), and the like. Be done.
  • Sulfur-containing compound A compound in which the nitrogen atom of the above-mentioned aminoacetic acid compound is replaced by a sulfur atom can generate an active radical by the same action.
  • Tin-containing compound A compound in which the nitrogen atom of the above-mentioned aminoacetic acid compound is replaced with a tin atom can generate an active radical by the same action.
  • Sulfinates An active radical can be generated by oxidation. Specific examples include sodium arylsulfinate and the like.
  • the image recording layer preferably contains a borate compound.
  • a borate compound a tetraarylborate compound or a monoalkyltriarylborate compound is preferable, a tetraarylborate compound is more preferable, and a tetraphenylborate compound is particularly preferable, from the viewpoint of the stability of the compound.
  • the counter cation contained in the borate compound is not particularly limited, but is preferably an alkali metal ion or a tetraalkylammonium ion, and more preferably a sodium ion, a potassium ion or a tetrabutylammonium ion.
  • sodium tetraphenylborate is preferably mentioned as a borate compound.
  • the highest occupied molecular orbital (HOMO) of the electron-donating polymerization initiator used in the present disclosure is preferably ⁇ 6.00 eV or more from the viewpoint of chemical resistance and UV printing durability, and ⁇ 5.95 eV. More preferably, it is more preferably ⁇ 5.93 eV or more. Further, the upper limit is preferably ⁇ 5.00 eV or less, and more preferably ⁇ 5.40 eV or less.
  • the highest occupied orbit (HOMO) and the lowest unoccupied orbit (LUMO) are calculated by the following method.
  • structural optimization is performed by DFT (B3L YP / 6-31G (d)).
  • the MO energy Ebare (unit: hartree) obtained by the MO energy calculation is converted into Escaled (unit: eV) used as the values of HOMO and LUMO in the present disclosure by the following formula.
  • Escaled 0.823168 ⁇ 27.2114 ⁇ Ebare ⁇ 1.07634 Note that 27.2114 is a coefficient for simply converting heartree into eV, 0.823168 and -1.07634 are adjustment coefficients, and HOMO and LUMO of the compound to be calculated are calculated values. To suit.
  • Bu represents an n-butyl group and Z represents a counter cation.
  • Examples of the counter cation represented by Z include Na + , K + , N + (Bu) 4, and the like.
  • Bu represents an n-butyl group.
  • an onium ion in the electron-accepting type polymerization initiator described later is also preferable.
  • Only one type of electron-donating polymerization initiator may be added, or two or more types may be used in combination.
  • the content of the electron-donating polymerization initiator is 0 with respect to the total mass of the image recording layer, from the viewpoint of color developability, color developability after exposure, developability, and UV printing durability of the lithographic printing plate precursor obtained. 0.01% by mass to 30% by mass is preferable, 0.05% by mass to 25% by mass is more preferable, and 0.1% by mass to 20% by mass is further preferable.
  • the image recording layer preferably contains an electron-accepting polymerization initiator from the viewpoints of color developability, color developability after exposure, developability, and UV printing durability of the resulting lithographic printing plate precursor.
  • the electron-accepting polymerization initiator used in the present disclosure is a compound that generates a polymerization initiation species such as a radical or a cation by the energy of light, heat or both, and is a known thermal polymerization initiator and has a small bond dissociation energy.
  • a compound having a bond, a photopolymerization initiator and the like can be appropriately selected and used.
  • the electron-accepting polymerization initiator is preferably a radical polymerization initiator, more preferably an onium salt compound. Further, the electron-accepting polymerization initiator is preferably an infrared-sensitive polymerization initiator.
  • the electron-accepting polymerization initiator may be used alone or in combination of two or more.
  • the radical polymerization initiator for example, (a) organic halide, (b) carbonyl compound, (c) azo compound, (d) organic peroxide, (e) metallocene compound, (f) azide compound, (g) ) Hexaarylbiimidazole compounds, (i) disulfone compounds, (j) oxime ester compounds, and (k) onium compounds.
  • organic halide (a) for example, compounds described in paragraphs 0022 to 0023 of JP-A-2008-195018 are preferable.
  • (b) carbonyl compound for example, compounds described in paragraph [0024] of JP-A-2008-195018 are preferable.
  • the azo compound (c) for example, the azo compounds described in JP-A-8-108621 can be used.
  • the organic peroxide (d) for example, compounds described in paragraph [0025] of JP-A-2008-195018 are preferable.
  • (e) metallocene compound for example, the compounds described in JP-A-2008-195018, paragraph 0026 are preferable.
  • Examples of the (f) azide compound include compounds such as 2,6-bis (4-azidobenzylidene) -4-methylcyclohexanone.
  • Examples of the (g) hexaarylbiimidazole compound for example, the compounds described in paragraph 0027 of JP-A-2008-195018 are preferable.
  • Examples of the (i) disulfone compound include compounds described in JP-A Nos. 61-166544 and 2002-328465.
  • As the oxime ester compound (j) for example, compounds described in paragraphs 0028 to 0030 of JP-A-2008-195018 are preferable.
  • oxime ester compounds and onium salt compounds are preferable from the viewpoint of curability.
  • an iodonium salt compound, a sulfonium salt compound or an azinium salt compound is preferable, an iodonium salt compound or a sulfonium salt compound is more preferable, and an iodonium salt compound is still more preferable.
  • Specific examples of these compounds are shown below, but the present disclosure is not limited thereto.
  • a diaryliodonium salt compound is preferable, and a diphenyliodonium salt compound substituted with an electron-donating group, for example, an alkyl group or an alkoxyl group is more preferable, and an asymmetric diphenyliodonium salt compound is preferable. ..
  • diphenyliodonium hexafluorophosphate
  • 4-methoxyphenyl-4- (2-methylpropyl) phenyliodonium hexafluorophosphate
  • 4- (2-methylpropyl) phenyl-p-tolyliodonium hexa Fluorophosphate
  • 4-hexyloxyphenyl-2,4,6-trimethoxyphenyliodonium hexafluorophosphate
  • 4-hexyloxyphenyl-2,4-diethoxyphenyliodonium tetrafluoroborate
  • 4-octyloxy Phenyl-2,4,6-trimethoxyphenyliodonium 1-perfluorobutanesulfonate
  • 4-octyloxyphenyl-2,4,6-trimethoxyphenyliodonium hexafluorophosphate, bis ( -t- butylphenyl) iodon
  • a triarylsulfonium salt compound is preferable, and an electron-withdrawing group, for example, a triarylsulfonium salt compound in which at least a part of the group on the aromatic ring is substituted with a halogen atom is preferable, and A triarylsulfonium salt compound in which the total number of halogen atoms on the ring is 4 or more is more preferable.
  • triphenylsulfonium hexafluorophosphate
  • triphenylsulfonium benzoyl formate
  • bis (4-chlorophenyl) phenylsulfonium benzoyl formate
  • bis (4-chlorophenyl) -4-methylphenylsulfonium tetrafluoro Borate
  • tris (4-chlorophenyl) sulfonium 3,5-bis (methoxycarbonyl) benzenesulfonate
  • tris (4-chlorophenyl) sulfonium hexafluorophosphate
  • a sulfonamide anion or a sulfonimide anion is preferable, and a sulfonimide anion is more preferable.
  • the sulfonamide anion is preferably an aryl sulfonamide anion.
  • a bisarylsulfonimide anion is preferable. Specific examples of the sulfonamide anion or sulfonimide anion are shown below, but the present disclosure is not limited thereto. In the following specific examples, Ph represents a phenyl group, Me represents a methyl group, and Et represents an ethyl group.
  • one of the preferable embodiments in the present disclosure is an embodiment in which the electron-accepting polymerization initiator and the electron-donating polymerization initiator form a salt.
  • the onium salt compound is a salt of an onium ion and an anion (for example, tetraphenylborate anion) in the electron-donating polymerization initiator described above can be mentioned.
  • an iodonium borate compound in which an iodonium cation (for example, di-p-tolyl iodonium cation) in the iodonium salt compound described later and a borate anion in the above-mentioned electron-donating polymerization initiator form a salt. Be done.
  • the electron-accepting polymerization initiator is a compound represented by the following formula (I) from the viewpoints of color developability, color developability after exposure, developability, and UV printing durability of the resulting lithographic printing plate precursor. Can be preferably used.
  • X represents a halogen atom, and specific examples thereof include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. Of these, a chlorine atom or a bromine atom is preferable because of its excellent sensitivity, and a bromine atom is particularly preferable.
  • A represents a divalent linking group selected from the group consisting of —CO—, —SO—, —SO 2 —, —PO— and —PO 2 —. Of these, —CO—, —SO— and —SO 2 — are more preferred, and —CO— and —SO 2 — are particularly preferred.
  • R X1 and R X2 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms.
  • Examples of the hydrocarbon that constitutes the hydrocarbon group include the hydrocarbons described in paragraphs 0013 to 0014 of JP-A-2002-162741, and specifically, the hydrocarbons include methane and ethane.
  • substituents examples include a monovalent non-metal atomic group other than hydrogen, a halogen atom (-F, -Br, -Cl, -I), a hydroxyl group, an alkoxy group, an aryloxy group, a mercapto group, an alkylthio group.
  • arylthio group alkyldithio group, aryldithio group, amino group, N-alkylamino group, N, N-dialkylamino group, N-arylamino group, N, N-diarylamino group, N-alkyl-N- Arylamino group, acyloxy group, carbamoyloxy group, N-alkylcarbamoyloxy group, N-arylcarbamoyloxy group, N, N-dialkylcarbamoyloxy group, N, N-diarylcarbamoyloxy group, N-alkyl-N-aryl Lucarbamoyloxy group, alkylsulfoxy group, arylsulfoxy group, acyl O group, acylamino group, N-alkylacylamino group, N-arylacylamino group, ureido group, N'-alkylureido group, N ', N acy
  • substituents may combine with each other or with the hydrocarbon group which is substituting to form a ring, and the substituent may be further substituted.
  • Preferred substituents include a halogen atom, an alkoxy group, an aryloxy group, an alkyl group, an alkenyl group, an alkynyl group and an aryl group.
  • the compounds represented by the following formulas (II) and (III) are preferable because they are excellent in visibility.
  • X has the same meaning as in formula (I), and R 3 , R 4 and R 5 are each independently a monovalent hydrocarbon having 1 to 20 carbon atoms. Represents a group.
  • R 3 , R 4 and R 5 are preferably aryl groups, and those in which the aryl group is substituted with an amide group are more preferable because of excellent balance between sensitivity and storage stability.
  • the compound represented by the formula (IV) is particularly preferable.
  • R 4 and R 5 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms.
  • p and q represent an integer of 1 to 5.
  • p + q 2 to 6.
  • Specific examples of the electron-accepting polymerization initiator represented by the above formula (I) include compounds represented by the following formulas, but the present disclosure is not limited thereto.
  • the image recording layer when the image recording layer contains an onium ion and the anion in the above-mentioned electron donating polymerization initiator, the image recording layer shall contain an electron accepting polymerization initiator and an electron donating polymerization initiator.
  • the lowest unoccupied molecular orbit (LUMO) of the electron-accepting polymerization initiator is preferably ⁇ 3.00 eV or less, and more preferably ⁇ 3.02 eV or less, from the viewpoint of chemical resistance and UV printing durability. Further, the lower limit is preferably ⁇ 3.80 eV or more, and more preferably ⁇ 3.60 eV or more.
  • the electron-accepting polymerization initiator may be added alone or in combination of two or more.
  • the content of the electron-accepting polymerization initiator is from 0.1% by mass to 50% by mass with respect to the total mass of the image recording layer from the viewpoint of color developability and UV printing durability of the lithographic printing plate precursor obtained. Is more preferable, 0.5% by mass to 30% by mass is more preferable, and 0.8% by mass to 20% by mass is particularly preferable.
  • an electron-donating polymerization initiator and an electron-accepting polymerization initiator form a counter salt
  • an electron donating polymerization initiator and an electron accepting polymerization initiator are used. It is preferable to include a compound formed by forming a counter salt. From the viewpoints of color forming property and UV printing durability of the lithographic printing plate obtained, the electron donating type initiator and the electron accepting type polymerization initiator form a counter salt.
  • the anion in the polymerization initiator and the cation in the electron-accepting polymerization initiator form a counter salt
  • the onium cation and the borate anion form a counter salt
  • a compound in which an iodonium cation or sulfonium cation and a borate anion form a counter salt, and a diaryl iodonium cation or triaryl sulfonium cation and a tetraaryl borate anion form a counter salt. Is particularly preferable.
  • Preferred embodiments of the anion in the electron donating polymerization initiator and the cation in the electron accepting polymerization initiator include a preferred embodiment of the anion in the electron donating polymerization initiator and the cation in the electron accepting polymerization initiator. It is the same.
  • the compound in which the electron-donating polymerization initiator and the electron-accepting polymerization initiator form a counter salt may be used alone or in combination of two or more kinds. Further, it may be used in combination with the electron-donating polymerization initiator or in combination with the electron-accepting polymerization initiator.
  • the content of the compound in which the electron-donating polymerization initiator and the electron-accepting polymerization initiator form a counter salt is determined from the viewpoint of color development and UV printing durability of the lithographic printing plate obtained. 0.1 wt% to 50 wt% is preferable, 0.5 wt% to 30 wt% is more preferable, and 0.8 wt% to 20 wt% is particularly preferable, with respect to the total weight of the layer.
  • the image-recording layer comprises the electron-donating polymerization initiator, the electron-accepting polymerization initiator, and the specific infrared absorbing agent from the viewpoints of color developability and UV printing durability of the lithographic printing plate obtained. It is preferable that the electron donating polymerization initiator has a HOMO of ⁇ 6.0 eV or more and the electron accepting polymerization initiator has a LUMO of ⁇ 3.0 eV or less. More preferable embodiments of the HOMO of the electron donating polymerization initiator and the LUMO of the electron accepting polymerization initiator are as described above.
  • the electron donating polymerization initiator, the infrared absorbing agent, and the electron accepting polymerization initiator for example, transfer energy as described in the following chemical formula. Guessed. Therefore, when the HOMO of the electron donating polymerization initiator is ⁇ 6.0 eV or more and the LUMO of the electron accepting polymerization initiator is ⁇ 3.0 eV or less, the radical generation efficiency is improved, It is considered that it is more likely to have excellent chemical resistance and UV printing durability. In addition, it is presumed that a part of the specific infrared absorbing agent may promote decomposition by infrared exposure by donating one electron from the electron donating polymerization initiator.
  • the difference between the HOMO of the electron-donating polymerization initiator and the HOMO of the infrared absorber is preferably 1.00 eV to ⁇ 0.200 eV, More preferably, it is 700 eV to ⁇ 0.100 eV.
  • a negative value means that the HOMO of the electron-donating polymerization initiator is higher than the HOMO of the infrared absorber.
  • the difference between the LUMO of the infrared absorber and the LUMO of the electron-accepting polymerization initiator is preferably 1.00 eV to ⁇ 0.200 eV, More preferably, it is 0.700 eV to ⁇ 0.100 eV.
  • a negative value means that the LUMO of the infrared absorber is higher than the LUMO of the electron-accepting polymerization initiator.
  • the image recording layer in the present disclosure contains a polymerizable compound.
  • a polymerizable compound even if it is a compound having a polymerizability, the above-mentioned specific binder polymer, the polymer particles described below, and the compounds corresponding to the binder polymer other than the specific binder polymer described below do not correspond to the polymerizable compounds.
  • the molecular weight (weight average molecular weight in the case of having a molecular weight distribution) of the polymerizable compound is 50 or more and less than 2,500. Is preferable, and more preferably 50 or more and 2,000 or less.
  • the mass per 1 mol of ethylenically unsaturated bond in the above polymerizable compound is 200 g / mol or less from the viewpoint of UV printing durability of the lithographic printing plate obtained. Is preferred, 50 g / mol or more and 200 g / mol or less is more preferred, 80 g / mol or more and 180 g / mol or less is more preferred, and 100 g / mol or more and 150 g / mol or less is particularly preferred.
  • the ethylenically unsaturated bond equivalent of the polymerizable compound can be specifically calculated as follows, for example.
  • the ClogP value of the polymerizable compound is preferably 6 or less, more preferably 2 or more and 6 or less, from the viewpoint of on-press developability and UV printing durability of the resulting lithographic printing plate. It is more preferably 3 or more and 6 or less, and particularly preferably 5 or more and 6 or less.
  • the value of ClogP in the present disclosure is a value obtained by calculating the common logarithm logP of the partition coefficient P between 1-octanol and water, and is the value obtained by Chem Draw Ultra ver. It is a value calculated by 12.0.2.1076 (Cambridge corporation).
  • the polymerizable compound used in the present disclosure may be, for example, a radically polymerizable compound or a cationically polymerizable compound.
  • the polymerizable group contained in the polymerizable compound include a group having an ethylenically unsaturated bond, an epoxy group, a methylol group, and an alkoxymethyl group.
  • the polymerizable compound is preferably an addition polymerizable compound containing at least one group having an ethylenically unsaturated bond (ethylenically unsaturated bond compound).
  • the ethylenically unsaturated compound is preferably a compound having at least one terminal ethylenically unsaturated bond, and more preferably a compound having two or more terminal ethylenically unsaturated bonds.
  • the group having an ethylenically unsaturated bond include a vinyl group, a (meth) allyl group, and a (meth) acryloyl group. From the viewpoint of UV printing durability in the lithographic printing plate obtained, a vinyl group or (meth ) It is preferably an acryloyl group.
  • the polymerizable compound has a chemical form such as a monomer, a prepolymer, that is, a dimer, a trimer or an oligomer, or a mixture thereof.
  • the polymerizable compound preferably contains a trifunctional or higher-functional polymerizable compound, more preferably a 7-functional or higher functional group, from the viewpoint of UV printing durability of the resulting lithographic printing plate. It is more preferable to include a functional or higher polymerizable group.
  • the polymerizable compound preferably contains a trifunctional or higher functional ethylenically unsaturated compound (preferably 7 or higher functional, more preferably 10 or higher functional) from the viewpoint of UV printing durability in the lithographic printing plate obtained. It is further preferable to include a (meth) acrylate compound having a functionality of 3 or more (preferably 7 or more, more preferably 10 or more).
  • Examples of the monomer include unsaturated carboxylic acids (for example, acrylic acid, methacrylic acid, itaconic acid, crotonic acid, isocrotonic acid, maleic acid, etc.), and their esters and amides, preferably unsaturated carboxylic acids. Esters of acids and polyhydric alcohol compounds and amides of unsaturated carboxylic acids and polyhydric amine compounds are used.
  • unsaturated carboxylic acids for example, acrylic acid, methacrylic acid, itaconic acid, crotonic acid, isocrotonic acid, maleic acid, etc.
  • esters of acids and polyhydric alcohol compounds and amides of unsaturated carboxylic acids and polyhydric amine compounds are used.
  • addition reaction products of unsaturated carboxylic acid esters or amides having a nucleophilic substituent such as a hydroxy group, an amino group and a mercapto group with monofunctional or polyfunctional isocyanates or epoxies, and monofunctional or polyfunctional is also preferably used.
  • a substitution reaction product of an unsaturated carboxylic acid ester or amide having a leaving substituent such as a tosyloxy group and a monofunctional or polyfunctional alcohol, amine, or thiol is also suitable.
  • JP-A-2006-508380 JP-A-2002-287344, JP-A-2008-256850, JP-A-2001-342222, JP-A-9-179296, and JP-A-9-179297.
  • JP-A-9-179298 JP-A-2004-294935, JP-A-2006-243493, JP-A-2002-275129, JP-A-2003-64130, JP-A-2003-280187, and It is described in, for example, Kaihei 10-333321.
  • the monomer of the ester of a polyhydric alcohol compound and an unsaturated carboxylic acid include acrylic acid esters such as ethylene glycol diacrylate, 1,3-butanediol diacrylate, tetramethylene glycol diacrylate, propylene glycol diacrylate, Examples thereof include trimethylolpropane triacrylate, hexanediol diacrylate, tetraethylene glycol diacrylate, pentaerythritol tetraacrylate, sorbitol triacrylate, isocyanuric acid ethylene oxide (EO) modified triacrylate, and polyester acrylate oligomer.
  • acrylic acid esters such as ethylene glycol diacrylate, 1,3-butanediol diacrylate, tetramethylene glycol diacrylate, propylene glycol diacrylate
  • examples thereof include trimethylolpropane triacrylate, hexanediol diacrylate, tetraethylene glycol diacrylate,
  • methacrylic acid ester As methacrylic acid ester, tetramethylene glycol dimethacrylate, neopentyl glycol dimethacrylate, trimethylolpropane trimethacrylate, ethylene glycol dimethacrylate, pentaerythritol trimethacrylate, bis [p- (3-methacryloxy-2-hydroxypropoxy) phenyl] Examples thereof include dimethyl methane and bis [p- (methacryloxyethoxy) phenyl] dimethyl methane.
  • amide monomer of a polyvalent amine compound and an unsaturated carboxylic acid examples include methylenebisacrylamide, methylenebismethacrylamide, 1,6-hexamethylenebisacrylamide, 1,6-hexamethylenebismethacrylamide, Diethylenetriamine tris acrylamide, xylylene bis acrylamide, xylylene bis methacrylamide, etc. are mentioned.
  • a urethane-based addition-polymerizable compound produced by addition reaction of isocyanate and hydroxy group is also suitable, and specific examples thereof include, for example, 2 molecules per molecule described in JP-B-48-41708.
  • Vinyl urethane compound containing two or more polymerizable vinyl groups in one molecule obtained by adding a vinyl monomer containing a hydroxy group represented by the following formula (M) to a polyisocyanate compound having two or more isocyanate groups Etc.
  • CH 2 C (R M4 ) COOCH 2 CH (R M5 ) OH (M)
  • R M4 and R M5 each independently represent a hydrogen atom or a methyl group.
  • the details of the structure of the polymerizable compound, whether it is used alone or in combination, the amount to be added, and the like can be arbitrarily set.
  • the content of the polymerizable compound is preferably 5% by mass to 75% by mass, more preferably 10% by mass to 70% by mass, and further preferably 15% by mass to 60% by mass based on the total mass of the image recording layer. More preferably, it is mass%.
  • the content of the specific binder polymer with respect to the total mass of the polymerizable compound in the image recording layer is preferably more than 0 mass% and 400 mass% or less, and preferably 25 mass% to 300 mass%. More preferably, it is more preferably 50% by mass to 200% by mass.
  • the specific binder polymer and the polymerizable compound preferably have a sea-island structure.
  • a structure in which the above-mentioned polymerizable compound is dispersed in an island shape (discontinuous layer) in the sea (continuous phase) of the specific binder polymer can be adopted. It is considered that the sea-island structure is easily formed by setting the content of the specific binder polymer with respect to the total mass of the polymerizable compound within the above range.
  • the image recording layer preferably further contains polymer particles.
  • the polymer particles preferably contain polymer particles having a hydrophilic group from the viewpoint of UV printing durability and on-press development property.
  • the hydrophilic group is not particularly limited as long as it has a hydrophilic structure, and examples thereof include an acid group such as a carboxy group, a hydroxy group, an amino group, a cyano group, and a polyalkylene oxide structure.
  • the hydrophilic group is preferably a group having a polyalkylene oxide structure, a group having a polyester structure, or a sulfonic acid group, and has a polyalkylene oxide structure. It is more preferable that it is a group having or a sulfonic acid group, and it is further preferable that it is a group having a polyalkylene oxide structure.
  • the polyalkylene oxide structure is preferably a polyethylene oxide structure, a polypropylene oxide structure, or a poly (ethylene oxide / propylene oxide) structure from the viewpoint of on-press developability.
  • the hydrophilic group preferably has a polypropylene oxide structure as a polyalkylene oxide structure, and more preferably has a polyethylene oxide structure and a polypropylene oxide structure.
  • the number of alkylene oxide structures in the polyalkylene oxide structure is preferably 2 or more, more preferably 5 or more, further preferably 5 to 200, and 8 to 8 from the viewpoint of on-press developability. Particularly preferred is 150.
  • the polymer particles may be selected from the group consisting of thermoplastic polymer particles, thermoreactive polymer particles, polymer particles having a polymerizable group, microcapsules containing a hydrophobic compound, and microgel (crosslinked polymer particles). preferable. Of these, polymer particles or microgels having a polymerizable group are preferable. In a particularly preferred embodiment, the polymer particles contain at least one ethylenically unsaturated polymerizable group. The presence of such polymer particles has the effect of enhancing the UV printing durability of the exposed area and the on-press developability of the unexposed area. Further, the polymer particles are preferably thermoplastic polymer particles.
  • thermoplastic polymer particles Research Disclosure No. of January 1992 is used.
  • the thermoplastic polymer particles described in 33303, JP-A-9-123387, JP-A-9-131850, JP-A-9-171249, JP-A-9-171250 and European Patent No. 931647 are preferred.
  • Specific examples of the polymer constituting the thermoplastic polymer particles include ethylene, styrene, vinyl chloride, methyl acrylate, ethyl acrylate, methyl methacrylate, ethyl methacrylate, vinylidene chloride, acrylonitrile, vinylcarbazole, and a polyalkylene structure.
  • thermoplastic polymer particles is preferably 0.01 ⁇ m to 3.0 ⁇ m.
  • the heat-reactive polymer particles include polymer particles having a heat-reactive group.
  • the heat-reactive polymer particles form a hydrophobized region due to cross-linking due to heat reaction and a change in functional group at that time.
  • the heat-reactive group in the polymer particles having a heat-reactive group may be a functional group that carries out any reaction as long as a chemical bond is formed, but it is preferably a polymerizable group.
  • Ethylenically unsaturated group eg, acryloyl group, methacryloyl group, vinyl group, allyl group, etc.
  • cationically polymerizable group eg, vinyl group, vinyloxy group, epoxy group, oxetanyl group, etc.
  • the microcapsule for example, as described in JP 2001-277740 A and JP 2001-277742 A, at least a part of the components of the image recording layer is encapsulated in a microcapsule.
  • the constituent components of the image recording layer may be contained outside the microcapsules.
  • a preferred embodiment of the image recording layer containing microcapsules has a structure in which a hydrophobic constituent component is encapsulated in the microcapsule and a hydrophilic constituent component is contained outside the microcapsule.
  • the microgel (crosslinked polymer particles) can contain a part of the components of the image recording layer on at least one of the surface and the inside thereof.
  • a reactive microgel having a radically polymerizable group on its surface is preferable from the viewpoint of image forming sensitivity and UV printing durability.
  • a publicly known method can be applied to microencapsulate or microgel the constituent components of the image recording layer.
  • a polyvalent isocyanate which is an adduct of a polyvalent phenol compound having two or more hydroxy groups in the molecule and isophorone diisocyanate. Those obtained by the reaction of the compound and the compound having active hydrogen are preferable.
  • the polyphenol compound a compound having a plurality of benzene rings having a phenolic hydroxy group is preferable.
  • the compound having active hydrogen is preferably a polyol compound or a polyamine compound, more preferably a polyol compound, and further preferably at least one compound selected from the group consisting of propylene glycol, glycerin and trimethylolpropane.
  • JP 2012 Polymer particles described in paragraphs 0032 to 0095 of JP-A-206495 are preferable.
  • the polymer particles have a hydrophobic main chain from the viewpoint of UV printing durability and solvent resistance, and i) a structural unit having a pendant cyano group directly bonded to the hydrophobic main chain, and , Ii) It is preferable to include both of the constituent units having a pendant group containing a hydrophilic polyalkylene oxide segment.
  • Preferred examples of the hydrophobic main chain include acrylic resin chains.
  • Preferred examples of the pendant cyano group include-[CH 2 CH (C ⁇ N)-] or-[CH 2 C (CH 3 ) (C ⁇ N)-].
  • the constituent unit having the pendant cyano group can be easily derived from an ethylenically unsaturated monomer such as acrylonitrile or methacrylonitrile, or a combination thereof.
  • an ethylenically unsaturated monomer such as acrylonitrile or methacrylonitrile, or a combination thereof.
  • the alkylene oxide in the hydrophilic polyalkylene oxide segment ethylene oxide or propylene oxide is preferable, and ethylene oxide is more preferable.
  • the number of repeating alkylene oxide structures in the hydrophilic polyalkylene oxide segment is preferably 10 to 100, more preferably 25 to 75, and even more preferably 40 to 50.
  • the resin-containing particles include those described in paragraphs 0039 to 0068 of JP-A-2008-503365.
  • the average particle size of the polymer particles is preferably 0.01 ⁇ m to 3.0 ⁇ m, more preferably 0.03 ⁇ m to 2.0 ⁇ m, still more preferably 0.10 ⁇ m to 1.0 ⁇ m. In this range, good resolution and stability over time can be obtained.
  • the average primary particle size of each particle in the present disclosure is measured by a light scattering method, or an electron micrograph of the particle is taken, and the particle size of the particles is measured in total of 5,000 particles, and the average The value shall be calculated.
  • the particle size value of spherical particles having the same particle area as the particle area on the photograph is defined as the particle size.
  • the average particle diameter in the present disclosure is a volume average particle diameter unless otherwise specified.
  • the content of the polymer particles is preferably 5% by mass to 90% by mass with respect to the total mass of the image recording layer.
  • the image recording layer preferably contains an acid color former.
  • the “acid color former” used in the present disclosure means a compound having a property of developing a color by heating while receiving an electron-accepting compound (for example, a proton of an acid or the like).
  • the acid color former has a partial skeleton such as lactone, lactam, sultone, spiropyran, ester, amide, etc., and when contacting with an electron-accepting compound, these partial skeletons are rapidly ring-opened or cleaved. Compounds are preferred.
  • Examples of such an acid color former include 3,3-bis (4-dimethylaminophenyl) -6-dimethylaminophthalide (referred to as "crystal violet lactone") and 3,3-bis (4- Dimethylaminophenyl) phthalide, 3- (4-dimethylaminophenyl) -3- (4-diethylamino-2-methylphenyl) -6-dimethylaminophthalide, 3- (4-dimethylaminophenyl) -3- (1 , 2-Dimethylindol-3-yl) phthalide, 3- (4-dimethylaminophenyl) -3- (2-methylindol-3-yl) phthalide, 3,3-bis (1,2-dimethylindole-3) -Yl) -5-dimethylaminophthalide, 3,3-bis (1,2-dimethylindol-3-yl) -6-dimethylaminophthalide, 3,3-bi (9-Ethylc
  • the acid color former used in the present disclosure may be at least one compound selected from the group consisting of spiropyran compounds, spirooxazine compounds, spirolactone compounds, and spirolactam compounds, from the viewpoint of color developability.
  • the hue of the dye after coloring is preferably green, blue or black from the viewpoint of visibility.
  • the acid color developing agent such as ETAC, RED500, RED520, CVL, S-205, BLACK305, BLACK400, BLACK100, BLACK500, H-7001, GREEN300, NIRBLACK78, BLUE220, H. -3035, BLUE203, ATP, H-1046, H-2114 (all manufactured by Fukui Yamada Chemical Co., Ltd.), ORANGE-DCF, Vermilion-DCF, PINK-DCF, RED-DCF, BLMB, CVL, GREEN-DCF.
  • ETAC RED500, RED520, CVL
  • S-205 BLACK305, BLACK400, BLACK100, BLACK500, H-7001, GREEN300, NIRBLACK78, BLUE220, H. -3035, BLUE203, ATP, H-1046, H-2114 (all manufactured by Fukui Yamada Chemical Co., Ltd.)
  • ORANGE-DCF Vermilion-DCF
  • PINK-DCF PINK-D
  • the acid color formers may be used alone or in combination of two or more kinds.
  • the content of the acid color former is preferably 0.5% by mass to 10% by mass, more preferably 1% by mass to 5% by mass, based on the total mass of the image recording layer.
  • the image recording layer may contain a binder polymer other than the specific binder polymer (hereinafter, also referred to as “other binder polymer”).
  • the specific binder polymer and the polymer corresponding to the polymer particles do not correspond to the other binder polymers. That is, the other binder polymer is a polymer having no constitutional unit formed of a styrene compound and having a non-particle shape.
  • the other binder polymer a (meth) acrylic resin, a polyvinyl acetal resin, or a polyurethane resin is preferable.
  • the other binder polymer a known binder polymer used in the image recording layer of the lithographic printing plate precursor can be preferably used.
  • the binder polymer used in the on-press development type lithographic printing plate precursor hereinafter, also referred to as "on-press development binder polymer" will be described in detail.
  • the binder polymer for on-press development is preferably a binder polymer having an alkylene oxide chain.
  • the binder polymer having an alkylene oxide chain may have a poly (alkylene oxide) moiety in the main chain or in a side chain.
  • it may be a graft polymer having a poly (alkylene oxide) in the side chain, or a block copolymer of a block composed of a poly (alkylene oxide) -containing repeating unit and a block composed of a (alkylene oxide) -free repeating unit.
  • a polyurethane resin is preferred when it has a poly (alkylene oxide) moiety in the main chain.
  • (meth) acrylic resin, polyvinyl acetal resin, polyurethane resin, polyurea resin, polyimide resin, polyamide resin, epoxy resin, polystyrene resin, novolac type Phenolic resins, polyester resins, synthetic rubbers and natural rubbers are mentioned, and (meth) acrylic resins are particularly preferable.
  • a polyfunctional thiol having a functionality of 6 or more and a functionality of 10 or less is used as a nucleus, and the nucleus has a polymer chain bonded to the nucleus by a sulfide bond, and the polymer chain has a polymerizable group.
  • examples thereof include a polymer compound (hereinafter, also referred to as a star polymer compound).
  • a star polymer compound for example, the compounds described in JP 2012-148555 A can be preferably used.
  • the star-shaped polymer compound has a polymerizable group such as an ethylenically unsaturated bond for improving the film strength of the image portion as described in JP-A-2008-195018, which is a main chain or a side chain, preferably a side chain. Those that are included in the chain are mentioned.
  • the polymerizable groups form crosslinks between polymer molecules and accelerate curing.
  • the polymerizable group is preferably an ethylenically unsaturated group such as a (meth) acrylic group, a vinyl group, an allyl group, a vinylphenyl group (styryl group) or an epoxy group, and a (meth) acrylic group, a vinyl group or a vinylphenyl group.
  • a group (styryl group) is more preferable from the viewpoint of polymerization reactivity, and a (meth) acrylic group is particularly preferable.
  • These groups can be introduced into the polymer by polymer reaction or copolymerization. For example, a reaction between a polymer having a carboxy group in its side chain and glycidyl methacrylate, or a reaction between a polymer having an epoxy group and an ethylenically unsaturated group-containing carboxylic acid such as methacrylic acid can be used. You may use these groups together.
  • the weight average molecular weight (Mw) as a polystyrene-converted value by the GPC method is preferably 2,000 or more, more preferably 5,000 or more, and 10,000 to 300, It is more preferably 000.
  • hydrophilic polymers such as polyacrylic acid and polyvinyl alcohol described in JP-A-2008-195018 can be used in combination. Also, a lipophilic polymer and a hydrophilic polymer can be used in combination.
  • other binder polymers may be used alone or in combination of two or more.
  • the other binder polymer can be contained in the image recording layer in an arbitrary amount, but the content of the binder polymer is 1% by mass to 90% by mass based on the total mass of the image recording layer. It is more preferably 5% by mass to 80% by mass.
  • the content of the other binder polymer with respect to the total weight of the specific binder polymer and the other binder polymer is more than 0% by mass and 99% by mass or less. Is preferred, 20% by mass to 95% by mass is more preferred, and 40% by mass to 90% by mass is even more preferred.
  • the content of the other binder polymer in the image recording layer is preferably lower than the content of the specific binder polymer.
  • the image recording layer may contain a chain transfer agent.
  • the chain transfer agent contributes to the improvement of UV printing durability in the planographic printing plate.
  • the chain transfer agent is preferably a thiol compound, more preferably a thiol compound having 7 or more carbon atoms from the viewpoint of boiling point (difficult to volatilize), and further preferably a compound having a mercapto group on the aromatic ring (aromatic thiol compound).
  • the thiol compound is preferably a monofunctional thiol compound.
  • chain transfer agents include the following compounds.
  • the chain transfer agent may be added alone or in combination of two or more kinds.
  • the content of the chain transfer agent is preferably 0.01% by mass to 50% by mass, more preferably 0.05% by mass to 40% by mass, and 0.1% by mass to 30% by mass based on the total mass of the image recording layer. % Is more preferable.
  • the image recording layer may contain a sensitizing agent such as a phosphonium compound, a nitrogen-containing low molecular weight compound, or an ammonium group-containing polymer in order to improve the inking property.
  • a sensitizing agent such as a phosphonium compound, a nitrogen-containing low molecular weight compound, or an ammonium group-containing polymer in order to improve the inking property.
  • these compounds function as a surface coating agent for the inorganic layered compound, and can suppress a decrease in ink receptivity during printing due to the inorganic layered compound.
  • oil sensitizer it is preferable to use a phosphonium compound, a nitrogen-containing low molecular weight compound, and an ammonium group-containing polymer in combination, and to use a phosphonium compound, a quaternary ammonium salt, and an ammonium group-containing polymer in combination. Is more preferable.
  • nitrogen-containing low molecular weight compound examples include amine salts and quaternary ammonium salts. Further, imidazolinium salts, benzimidazolinium salts, pyridinium salts, and quinolinium salts are also included. Of these, quaternary ammonium salts and pyridinium salts are preferable.
  • tetramethylammonium hexafluorophosphate
  • tetrabutylammonium hexafluorophosphate
  • dodecyltrimethylammonium p-toluenesulfonate
  • benzyltriethylammonium hexafluorophosphate
  • benzyldimethyloctylammonium hexafluorophosphate.
  • Felt, benzyldimethyldodecyl ammonium hexafluorophosphate, compounds described in paragraphs 0021 to 0037 of JP 2008-284858 A, compounds described in paragraphs 0030 to 0057 of JP 2009-90645 A, and the like.
  • the ammonium group-containing polymer may have an ammonium group in its structure, and a polymer containing 5 mol% to 80 mol% of a (meth) acrylate having an ammonium group in its side chain as a copolymerization component is preferable. Specific examples thereof include the polymers described in paragraphs 0089 to 0105 of JP2009-208458A.
  • the ammonium salt-containing polymer preferably has a reduced specific viscosity (unit: ml / g) in the range of 5 to 120, which is determined by the measuring method described in JP-A-2009-208458, and preferably in the range of 10 to 110. Those having a range of 15 to 100 are particularly preferable.
  • Mw weight average molecular weight
  • the oil sensitizer may be added alone or in combination of two or more.
  • the content of the oil sensitizer is preferably 1% by mass to 40.0% by mass, more preferably 2% by mass to 25.0% by mass, and further preferably 3% by mass to 20% by mass based on the total mass of the image recording layer. % Is more preferable.
  • the image recording layer used in the present disclosure may contain a development accelerator.
  • a hydrophilic polymer compound or a hydrophilic low molecular weight compound is preferable.
  • the hydrophilic high molecular weight compound means a compound having a molecular weight (weight average molecular weight when having a molecular weight distribution) of 3,000 or more
  • the hydrophilic low molecular weight compound means a molecular weight (weight average when having a molecular weight distribution).
  • the hydrophilic polymer compound examples include cellulose compounds and polyvinyl alcohol, with cellulose compounds being preferred.
  • examples of the cellulose compound include cellulose or a compound in which at least a part of cellulose is modified (modified cellulose compound), and a modified cellulose compound is preferable.
  • the modified cellulose compound is preferably a compound in which at least a part of the hydroxy group of cellulose is substituted with at least one selected from the group consisting of an alkyl group and a hydroxyalkyl group.
  • an alkyl cellulose compound or a hydroxyalkyl cellulose compound is preferable, and a hydroxyalkyl cellulose compound is more preferable.
  • Preferred examples of the alkyl cellulose compound include methyl cellulose.
  • Preferred examples of the hydroxyalkyl cellulose compound include hydroxypropyl cellulose.
  • the molecular weight (weight average molecular weight in the case of having a molecular weight distribution) of the hydrophilic polymer compound is preferably 3,000 to 300,000, and more preferably 10,000 to 150,000.
  • hydrophilic low molecular weight compound examples include glycol compounds, polyol compounds, organic amine compounds, organic sulfonic acid compounds, organic sulfamine compounds, organic sulfuric acid compounds, organic phosphonic acid compounds, organic carboxylic acid compounds, betaine compounds, and the like, and polyol compounds. Preferred are organic sulfonic acid compounds and betaine compounds.
  • glycol compound examples include glycols such as ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol and tripropylene glycol, and ether or ester derivatives of these compounds.
  • examples of the polyol compound include glycerin, pentaerythritol, tris (2-hydroxyethyl) isocyanurate and the like.
  • examples of the organic amine compound include triethanolamine, diethanolamine, monoethanolamine and the like and salts thereof.
  • Examples of the organic sulfonic acid compound include alkyl sulfonic acid, toluene sulfonic acid, benzene sulfonic acid and the like, and salts thereof, and alkyl sulfonic acid having an alkyl group having 8 to 20 carbon atoms is preferable.
  • Examples of the organic sulfamine compound include alkylsulfamic acid and salts thereof.
  • Examples of the organic sulfuric acid compound include alkyl sulfuric acid, alkyl ether sulfuric acid and the like and salts thereof.
  • Examples of the organic phosphonic acid compound include phenylphosphonic acid and the like and salts thereof.
  • organic carboxylic acid compound examples include tartaric acid, oxalic acid, citric acid, malic acid, lactic acid, gluconic acid and the salts thereof.
  • betaine compounds include phosphobetaine compounds, sulfobetaine compounds, and carboxybetaine compounds, with trimethylglycine being preferred.
  • the molecular weight (weight average molecular weight in the case of having a molecular weight distribution) of the hydrophilic low molecular weight compound is preferably 50 or more and less than 3,000, and more preferably 100 to 1,000.
  • the development accelerator may be added alone or in combination of two or more kinds.
  • the content of the development accelerator relative to the total mass of the image recording layer is preferably 0.1% by mass or more and 20% by mass or less, more preferably 0.5% by mass or more and 15% by mass or less, and 1% by mass or more and 10% by mass or more. It is more preferably not more than mass%.
  • the image recording layer may contain, as other components, a surfactant, a polymerization inhibitor, a higher fatty acid derivative, a plasticizer, inorganic particles, an inorganic layered compound and the like. Specifically, the description in paragraphs 0114 to 0159 of JP 2008-284817 A can be referred to.
  • the image recording layer in the lithographic printing plate precursor according to the present disclosure is applied by dispersing or dissolving each of the necessary components described above in a known solvent, as described in paragraphs 0142 to 0143 of JP 2008-195018 A. It can be formed by preparing a liquid, applying the coating liquid on a support by a known method such as bar coater coating, and drying.
  • the coating amount (solid content) of the image recording layer after coating and drying varies depending on the use, but is preferably 0.3 g / m 2 to 3.0 g / m 2 . Within this range, good sensitivity and good film properties of the image recording layer can be obtained.
  • a known solvent can be used as the solvent.
  • the solvent may be used alone or in combination of two or more.
  • the solid content concentration in the coating liquid is preferably 1% by mass to 50% by mass.
  • the coating amount (solid content) of the image recording layer after coating and drying varies depending on the application, but is 0.3 g / m 2 to 3.0 g / m 2 from the viewpoint of obtaining good sensitivity and good film characteristics of the image recording layer. m 2 is preferred.
  • the thickness of the image recording layer in the lithographic printing plate precursor according to the present disclosure is preferably 0.1 ⁇ m to 3.0 ⁇ m, and more preferably 0.3 ⁇ m to 2.0 ⁇ m.
  • a section cut in a direction perpendicular to the surface of the lithographic printing plate precursor is prepared, and the cross section of the section is observed with a scanning microscope (SEM). Confirmed by.
  • the lithographic printing plate precursor according to the present disclosure preferably has an overcoat layer (also referred to as “protective layer”) on the surface of the image recording layer opposite to the support side.
  • the thickness of the overcoat layer is preferably larger than that of the image recording layer.
  • the overcoat layer has a function of suppressing an image formation inhibiting reaction by blocking oxygen, a function of preventing scratches in the image recording layer, and a function of preventing ablation during exposure to a high illuminance laser.
  • the overcoat layer having such characteristics is described, for example, in US Pat. No. 3,458,311 and JP-B-55-49729.
  • a water-soluble polymer or a water-insoluble polymer can be appropriately selected and used, and two or more types can be mixed and used as necessary.
  • the water-soluble polymer means that a solution of 1 g or more dissolved in 100 g of pure water at 70 ° C. and 1 g of polymer dissolved in 100 g of pure water at 70 ° C. is cooled to 25 ° C.
  • the water-soluble polymer used in the overcoat layer include polyvinyl alcohol, modified polyvinyl alcohol, polyvinylpyrrolidone, water-soluble cellulose derivative, polyethylene glycol, poly (meth) acrylonitrile and the like.
  • modified polyvinyl alcohol acid modified polyvinyl alcohol having a carboxy group or a sulfo group is preferably used. Specific examples thereof include the modified polyvinyl alcohols described in JP-A-2005-250216 and JP-A-2006-259137.
  • the above water-soluble polymers it is preferable to include polyvinyl alcohol, and it is more preferable to include polyvinyl alcohol having a saponification degree of 50% or more.
  • the saponification degree is preferably 60% or more, more preferably 70% or more, and further preferably 85% or more.
  • the upper limit of the degree of saponification is not particularly limited and may be 100% or less.
  • the saponification degree is measured according to the method described in JIS K 6726: 1994. Further, as one aspect of the overcoat layer, an aspect including polyvinyl alcohol and polyethylene glycol is also preferably cited.
  • the content of the water-soluble polymer with respect to the total weight of the overcoat layer is preferably 1% by mass to 99% by mass, and 3% by mass to 97% by mass. It is more preferable that the amount is 5% by mass to 95% by mass.
  • the overcoat layer may contain an inorganic layered compound in order to enhance the oxygen barrier property.
  • the inorganic layered compound is a particle having a thin tabular shape, and includes, for example, mica groups such as natural mica and synthetic mica, talc represented by the formula: 3MgO.4SiO.H 2 O, teniolite, montmorillonite, saponite, and hector. Examples include light and zirconium phosphate.
  • the inorganic layered compound preferably used is a mica compound.
  • mica compound examples include compounds represented by the formula: A (B, C) 2-5 D 4 O 10 (OH, F, O) 2 [where A is K, Na or Ca, and B and C are It is any one of Fe (II), Fe (III), Mn, Al, Mg, and V, and D is Si or Al. ]
  • Mica groups such as natural mica and synthetic mica represented by
  • examples of natural mica include muscovite, soda mica, phlogopite, biotite, and ledocite.
  • Synthetic mica includes non-swelling mica such as fluorophlogopite KMg 3 (AlSi 3 O 10 ) F 2 and potassium tetrasilicon mica KMg 2.5 Si 4 O 10 ) F 2 ; and Na tetrasilylic mica NaMg 2.
  • the lattice layer is deficient in positive charge, and cations such as Li + , Na + , Ca 2+ , and Mg 2+ are adsorbed between the layers to compensate for it.
  • the cations existing between these layers are called exchangeable cations and can exchange with various cations.
  • the ionic radius is small, so that the bond between the layered crystal lattices is weak and the layer swells greatly with water.
  • shear is applied in that state, it is easily cleaved to form a stable sol in water.
  • Swelling synthetic mica has such a strong tendency that it is particularly preferably used.
  • the aspect ratio is preferably 20 or more, more preferably 100 or more, and particularly preferably 200 or more.
  • the aspect ratio is the ratio of the major axis to the thickness of the particle, and can be measured, for example, from a projection view of the particle with a micrograph. The larger the aspect ratio, the greater the effect obtained.
  • the particle diameter of the mica compound is preferably 0.3 ⁇ m to 20 ⁇ m, more preferably 0.5 ⁇ m to 10 ⁇ m, and particularly preferably 1 ⁇ m to 5 ⁇ m.
  • the average thickness of the particles is preferably 0.1 ⁇ m or less, more preferably 0.05 ⁇ m or less, and particularly preferably 0.01 ⁇ m or less.
  • a preferable embodiment has a thickness of about 1 nm to 50 nm and a surface size (major axis) of about 1 ⁇ m to 20 ⁇ m.
  • the content of the inorganic layered compound is preferably 1% by mass to 60% by mass, more preferably 3% by mass to 50% by mass, based on the total solid content of the overcoat layer. Even when a plurality of types of inorganic layered compounds are used in combination, the total amount of the inorganic layered compounds is preferably the above content. Within the above range, the oxygen barrier property is improved and good sensitivity is obtained. In addition, it is possible to prevent a decrease in inking property.
  • the overcoat layer may contain known additives such as a plasticizer for imparting flexibility, a surfactant for improving coating properties, and inorganic particles for controlling the slipperiness of the surface. Further, the overcoat layer may contain the oil-sensitizing agent described in the image recording layer.
  • the overcoat layer is applied by a known method.
  • the coating amount of the overcoat layer (solid content) is preferably from 0.01g / m 2 ⁇ 10g / m 2, more preferably 0.02g / m 2 ⁇ 3g / m 2, 0.02g / m 2 ⁇ 1g / m 2 is particularly preferred.
  • the film thickness of the overcoat layer in the lithographic printing plate precursor according to the present disclosure is preferably 0.1 ⁇ m to 5.0 ⁇ m, and more preferably 0.3 ⁇ m to 4.0 ⁇ m.
  • the film thickness of the overcoat layer in the lithographic printing plate precursor according to the present disclosure is preferably 1.1 to 5.0 times, and preferably 1.5 to 3.0 times the film thickness of the image recording layer. It is more preferable that the number is twice.
  • the lithographic printing plate precursor according to the present disclosure preferably has an undercoat layer (also referred to as an intermediate layer) between the image recording layer and the support.
  • the undercoat layer strengthens the adhesion between the support and the image recording layer in the exposed area and facilitates the peeling of the image recording layer from the support in the unexposed area, thus suppressing the deterioration of UV printing durability. However, it contributes to improving the developability. Further, in the case of infrared laser exposure, the undercoat layer functions as a heat insulating layer, so that it also has an effect of preventing the heat generated by the exposure from diffusing into the support and lowering the sensitivity.
  • the compound used in the undercoat layer includes a polymer having an adsorptive group and a hydrophilic group capable of being adsorbed on the surface of the support.
  • a polymer having an adsorptive group and a hydrophilic group and further having a crosslinkable group in order to improve the adhesion to the image recording layer is preferable.
  • the compound used in the undercoat layer may be a low molecular weight compound or a polymer.
  • the compounds used in the undercoat layer may be used as a mixture of two or more, if necessary.
  • the compound used for the undercoat layer is a polymer
  • a copolymer of a monomer having an adsorptive group, a monomer having a hydrophilic group and a monomer having a crosslinkable group is preferable.
  • the adsorptive group that can be adsorbed on the surface of the support include a phenolic hydroxy group, a carboxy group, —PO 3 H 2 , —OPO 3 H 2 , —CONHSO 2 —, —SO 2 NHSO 2 —, and —COCH 2 COCH 3 Is preferred.
  • a hydrophilic group a sulfo group or a salt thereof, or a salt of a carboxy group is preferable.
  • the polymer may have a crosslinkable group introduced by salt formation with a polar substituent of the polymer and a substituent having a countercharge to the polar substituent and a compound having an ethylenically unsaturated bond, and Other monomers, preferably hydrophilic monomers, may be further copolymerized.
  • Preferable examples are phosphorus compounds having a heavy bond reactive group.
  • Crosslinkable groups preferably ethylenically unsaturated bond groups
  • a low molecular weight or high molecular weight compound having a functional group that interacts with the surface and a hydrophilic group is also preferably used.
  • high molecular polymers having an adsorptive group, a hydrophilic group and a crosslinkable group capable of being adsorbed on the surface of the support described in JP-A-2005-125749 and JP-A-2006-188038.
  • the content of the ethylenically unsaturated bond group in the polymer used for the undercoat layer is preferably 0.1 mmol to 10.0 mmol, and more preferably 0.2 mmol to 5.5 mmol per 1 g of the polymer.
  • the weight average molecular weight (Mw) of the polymer used in the undercoat layer is preferably 5,000 or more, more preferably 10,000 to 300,000.
  • the undercoat layer is, in addition to the above-mentioned undercoat layer compound, a chelating agent, a secondary or tertiary amine, a polymerization inhibitor, an amino group or a functional group having a polymerization inhibition ability and a support surface in order to prevent stains with time.
  • a compound having a group that interacts with for example, 1,4-diazabicyclo [2.2.2] octane (DABCO), 2,3,5,6-tetrahydroxy-p-quinone, chloranil, sulfophthalic acid, hydroxy
  • DABCO 1,4-diazabicyclo [2.2.2] octane
  • 2,3,5,6-tetrahydroxy-p-quinone chloranil, sulfophthalic acid, hydroxy
  • Ethylethylenediaminetriacetic acid, dihydroxyethylethylenediaminediacetic acid, hydroxyethyliminodiacetic acid, etc. may be contained.
  • the undercoat layer is applied by a known method.
  • the coating amount (solid content) of the undercoat layer is preferably 0.1 mg / m 2 to 100 mg / m 2, and more preferably 1 mg / m 2 to 30 mg / m 2 .
  • a lithographic printing plate can be prepared by subjecting the lithographic printing plate precursor according to the present disclosure to imagewise exposure and development.
  • a method of producing a lithographic printing plate according to the present disclosure includes a step of exposing a lithographic printing plate precursor according to the present disclosure to an image (hereinafter, also referred to as “exposure step”), a printing ink and a dampening solution on a printing machine. It is preferable to include a step of supplying at least one selected from the group consisting of water to remove the image recording layer in the non-image area (hereinafter, also referred to as “on-press development step”).
  • a lithographic printing method includes a step of exposing a lithographic printing plate precursor according to the present disclosure in an imagewise manner (exposure step), and printing by supplying at least one selected from the group consisting of printing ink and fountain solution. It is preferable to include a step (on-press development step) of removing the image recording layer in the non-image area on the machine to produce a lithographic printing plate and a step of printing with the obtained lithographic printing plate (printing step).
  • the exposure step and the on-press development step in the method for producing a lithographic printing plate will be described.
  • the exposure step in the method for producing a lithographic printing plate according to the present disclosure and the exposure step in the lithographic printing method according to the present disclosure are the same.
  • the steps are the same as the on-press development step in the method for producing a lithographic printing plate according to the present disclosure and the on-press development step in the lithographic printing method according to the present disclosure.
  • the method for producing a lithographic printing plate according to the present disclosure preferably includes an exposure step of imagewise exposing the lithographic printing plate precursor according to the present disclosure to form an exposed portion and an unexposed portion.
  • the lithographic printing plate precursor according to the present disclosure is preferably subjected to laser exposure through a transparent original image having a line image, a halftone image or the like, or imagewise by laser light scanning using digital data.
  • the wavelength of the light source is preferably 750 nm to 1,400 nm.
  • solid-state lasers and semiconductor lasers that emit infrared rays are suitable.
  • the output is preferably 100 mW or more, the exposure time per pixel is preferably 20 microseconds or less, and the irradiation energy amount is 10 mJ / cm 2 to 300 mJ / cm 2. preferable. Further, it is preferable to use a multi-beam laser device in order to shorten the exposure time.
  • the exposure mechanism may be any of an inner drum system, an outer drum system, a flat bed system, and the like. Image exposure can be performed by a conventional method using a platesetter or the like. In the case of on-press development, the lithographic printing plate precursor may be mounted on the printing machine and then imagewise exposed on the printing machine.
  • the method for producing a lithographic printing plate according to the present disclosure comprises an on-press development step of removing at least one selected from the group consisting of printing ink and fountain solution on the printing machine to remove the image recording layer in the non-image area. It is preferable to include.
  • the on-press development method will be described below.
  • the image-exposed lithographic printing plate precursor is supplied with an oil-based ink and an aqueous component on the printing machine, and the image recording layer in the non-image area is removed to prepare a lithographic printing plate. Is preferred.
  • the uncured image-recording layer is formed in the non-image area at the initial stage of printing by one or both of the supplied oil-based ink and the water-based component. It is dissolved or dispersed and removed, and the hydrophilic surface is exposed at that portion.
  • the image recording layer cured by exposure forms an oil-based ink receiving portion having a lipophilic surface.
  • the oil-based ink or the aqueous component may be first supplied to the plate surface
  • the oil-based ink is first supplied in order to prevent the aqueous component from being contaminated by the removed components of the image recording layer.
  • the lithographic printing plate precursor is on-press developed on the printing machine and used as it is for printing a large number of sheets.
  • a printing ink and a fountain solution for ordinary lithographic printing are preferably used.
  • the wavelength of the light source is preferably 300 nm to 450 nm or 750 nm to 1,400 nm.
  • a lithographic printing plate precursor containing a sensitizing dye having an absorption maximum in this wavelength region in the image recording layer is preferably used, and the light source of 750 nm to 1,400 nm is preferably the above-mentioned one. Be done.
  • a semiconductor laser is suitable as a light source of 300 nm to 450 nm.
  • a method of producing a lithographic printing plate according to the present disclosure includes a step of imagewise exposing a lithographic printing plate precursor according to the present disclosure, and a step of producing a lithographic printing plate by removing an image recording layer in a non-image area with a developer ( "Also referred to as a developing solution developing step"). Further, the lithographic printing method according to the present disclosure, a step of imagewise exposing the lithographic printing plate precursor according to the present disclosure, a step of producing a lithographic printing plate by removing the image recording layer of the non-image area with a developer, And a step of printing with the obtained planographic printing plate.
  • the developing solution a known developing solution can be used.
  • the pH of the developer is not particularly limited and may be a strong alkaline developer, but a developer having a pH of 2 to 11 is preferable.
  • a developer having a pH of 2 to 11 include a developer containing at least one of a surfactant and a water-soluble polymer compound.
  • the protective layer is removed by the pre-water washing step, then the alkali developing is performed, the alkali is washed away by the post-rinsing step, the gum solution treatment is performed, and the drying step is performed. Is mentioned. Further, when the above developer containing a surfactant or a water-soluble polymer compound is used, development-gum solution treatment can be carried out simultaneously.
  • the post-water washing step is not particularly required, and the development step and the gum solution treatment with one solution can be followed by the drying step. Further, since the protective layer can be removed at the same time as the development and the gum solution treatment, the pre-water washing step is not particularly necessary. After the development treatment, it is preferable to remove excess developer using a squeeze roller or the like and then dry.
  • a lithographic printing method includes a printing step of supplying a printing ink to a lithographic printing plate to print a recording medium.
  • the printing ink is not particularly limited, and various known inks can be used as desired.
  • oil-based ink or ultraviolet curable ink (UV ink) is preferably mentioned.
  • dampening water may be supplied as needed.
  • the printing process may be performed continuously with the on-press development process or the developing solution development process without stopping the printing press.
  • the recording medium is not particularly limited, and a known recording medium can be used as desired.
  • lithographic printing is performed before exposure, during exposure, and between exposure and development, if necessary.
  • the entire surface of the plate precursor may be heated.
  • the heating before development is preferably performed under mild conditions of 150 ° C. or lower.
  • the temperature is in the range of 100 ° C to 500 ° C. Within the above range, a sufficient image strengthening effect can be obtained, and problems such as deterioration of the support and thermal decomposition of the image area can be suppressed.
  • the molecular weight is a weight average molecular weight (Mw) and the ratio of the constitutional repeating units is a molar percentage, except for those specifically specified.
  • Mw weight average molecular weight
  • the weight average molecular weight (Mw) is a value measured as a polystyrene conversion value by a gel permeation chromatography (GPC) method.
  • the aluminum plate was etched by immersing it in a 25 mass% sodium hydroxide aqueous solution at 45 ° C for 9 seconds, washed with water, further immersed in a 20 mass% nitric acid aqueous solution at 60 ° C for 20 seconds, and washed with water.
  • the amount of etching on the grained surface was about 3 g / m 2 .
  • an electrochemical roughening treatment was continuously performed using an alternating voltage of 60 Hz.
  • the electrolytic solution was a 1% by mass nitric acid aqueous solution (containing 0.5% by mass of aluminum ion), and the solution temperature was 50 ° C.
  • a time TP from when the current value reaches a peak to zero is 0.8 ms
  • a duty ratio of 1: 1 and a trapezoidal rectangular wave AC are used, and an electrochemical roughening treatment is performed with a carbon electrode as a counter electrode. I went. Ferrite was used for the auxiliary anode.
  • the current density was 30 A / dm 2 at the peak value of the current, and 5% of the current flowing from the power supply was shunted to the auxiliary anode.
  • the quantity of electricity in nitric acid electrolysis was 175 C / dm 2 when the aluminum plate was the anode. Then, washing with water was performed by spraying.
  • a nitric acid electrolysis was carried out using a 0.5% by mass hydrochloric acid aqueous solution (containing 0.5% by mass of aluminum ions) and an electrolytic solution at a liquid temperature of 50 ° C. under the condition that the aluminum plate was an anode at an electric quantity of 50 C / dm 2.
  • An electrochemical surface-roughening treatment was carried out in the same manner as in (1), followed by washing with water by spraying.
  • the surface was observed at a magnification of 150,000 times without performing the vapor deposition treatment and the like, and 50 pores were randomly extracted to obtain an average value.
  • the standard deviation was ⁇ 10% or less of the average value.
  • the obtained supports were used as the supports of Examples 1-1 to 1-18, 2-1 to 2-18 and Comparative Examples 1 to 3.
  • Electrochemical surface roughening treatment in hydrochloric acid aqueous solution electrolysis was performed using an alternating current using an electrolytic solution having a hydrochloric acid concentration of 14 g / L, an aluminum ion concentration of 13 g / L, and a sulfuric acid concentration of 3 g / L. Roughening treatment was performed. The liquid temperature of the electrolytic solution was 30 ° C. The aluminum ion concentration was adjusted by adding aluminum chloride.
  • the waveform of the alternating current is a sine wave with positive and negative waveforms symmetrical, the frequency is 50 Hz, the anode reaction time and the cathode reaction time in one cycle of the alternating current are 1: 1, and the current density is the peak current value of the alternating current waveform. It was 75 A / dm 2 .
  • the amount of electricity was 450 C / dm 2 in terms of the total amount of electricity deposited by the aluminum plate in the anode reaction, and the electrolytic treatment was carried out every 125 C / dm 2 in four times with a conduction interval of 4 seconds.
  • a carbon electrode was used as the counter electrode of the aluminum plate. Then, a water washing process was performed.
  • Alkaline etching treatment The aluminum plate after the electrochemical surface roughening treatment is etched by spraying an aqueous caustic soda solution having a caustic soda concentration of 5 mass% and an aluminum ion concentration of 0.5 mass% with a spray tube at a temperature of 45 ° C. Processed. The amount of aluminum dissolved on the surface subjected to the electrochemical graining treatment was 0.2 g / m 2 . Then, a water washing process was performed.
  • Desmutting treatment in acidic aqueous solution Desmutting treatment was performed in an acidic aqueous solution.
  • a waste liquid generated in the anodizing treatment step (aluminum ion 5.0 g / L dissolved in 170 g / L sulfuric acid aqueous solution) was used.
  • the liquid temperature was 30 ° C.
  • the desmutting liquid was sprayed onto the spray and desmutted for 3 seconds.
  • (Af) First-stage anodizing treatment The first-stage anodizing treatment was performed using the anodizing apparatus by DC electrolysis having the structure shown in FIG. Anodizing treatment was performed under the conditions shown in Table 1 to form an anodized film having a predetermined film thickness.
  • the aluminum plate 616 is transported as shown by the arrow in FIG. The aluminum plate 616 is charged (+) by the power supply electrode 620 in the power supply tank 612 in which the electrolytic solution 618 is stored.
  • the aluminum plate 616 is conveyed upward by the roller 622 in the power supply tank 612, is turned downward by the nip roller 624, is conveyed toward the electrolytic treatment tank 614 in which the electrolytic solution 626 is stored, and is conveyed by the roller 628. Turned horizontally.
  • the aluminum plate 616 is negatively charged by the electrolytic electrode 630 to form an anodized film on the surface thereof, and the aluminum plate 616 exiting the electrolytic treatment tank 614 is conveyed to the subsequent step.
  • the roller 622, the nip roller 624, and the roller 628 form a direction changing means. By 628, it is conveyed in a mountain shape and an inverted U shape.
  • the power feeding electrode 620 and the electrolytic electrode 630 are connected to a DC power source 634.
  • Second-stage anodizing treatment A second-stage anodizing treatment was performed using the anodizing apparatus for direct current electrolysis having the structure shown in FIG. Anodizing treatment was performed under the conditions shown in Table 1 to form an anodized film having a predetermined film thickness. A support S1 of the example was obtained from the above surface treatment A.
  • the average diameter (nm) of the large-diameter pores in the anodic oxide coating having micropores after the second anodizing step obtained above on the surface of the anodic-oxidation coating the average diameter (nm) at the communicating position of the small-diameter pores.
  • Depth of large diameter hole and small diameter hole (nm) pit density (micropore density, unit: pieces / ⁇ m 2 ), and thickness of anodic oxide film from bottom of small diameter hole to aluminum plate surface (Nm) is summarized in Table 2.
  • the cross section of the support was observed by FE-SEM (large-diameter hole depth observation: 150,000 times, small diameter). Observation of hole depth: 50,000 times), and is a value obtained by measuring the depth of 25 arbitrary micropores in the obtained image and averaging them.
  • the film amount (AD) amount in the first anodizing column and the film amount (AD) in the second anodizing column represent the film amounts obtained in each treatment.
  • the electrolytic solution used is an aqueous solution containing the components shown in Table 1.
  • the waveform of the alternating current is a sine wave in which the positive and negative waveforms are symmetrical, the frequency is 50 Hz, the anode reaction time and the cathode reaction time in one cycle of the alternating current are 1: 1, and the current density is the peak current value of the alternating current waveform. It was 75 A / dm 2 .
  • the amount of electricity was 450 C / dm 2 as the total amount of electricity deposited by the aluminum plate in the anode reaction, and the electrolytic treatment was performed at 125 C / dm 2 in four times with a 4-second conduction interval. A carbon electrode was used as the counter electrode of the aluminum plate. Then, a water washing process was performed.
  • (Bd) Alkaline etching treatment The aluminum plate after the electrochemical surface roughening treatment is etched by spraying an aqueous caustic soda solution having a caustic soda concentration of 5 mass% and an aluminum ion concentration of 0.5 mass% at a temperature of 45 ° C with a spray tube. Processed. The amount of aluminum dissolved on the surface subjected to the electrochemical graining treatment was 0.2 g / m 2 . Then, a water washing process was performed.
  • a first-stage anodizing treatment was performed by using the anodizing apparatus for direct current electrolysis having the structure shown in FIG.
  • Anodizing treatment was performed under the conditions shown in Table 1 to form an anodized film having a predetermined film thickness.
  • the waveform of the alternating current is a sine wave in which the positive and negative waveforms are symmetrical, the frequency is 50 Hz, the anode reaction time and the cathode reaction time in one cycle of the alternating current are 1: 1, and the current density is the peak current value of the alternating current waveform. It was 75 A / dm 2 .
  • the amount of electricity was 450 C / dm 2 as the total amount of electricity deposited by the aluminum plate in the anode reaction, and the electrolytic treatment was performed at 125 C / dm 2 in four times with a 4-second conduction interval. A carbon electrode was used as the counter electrode of the aluminum plate. Then, a water washing process was performed.
  • (Cg) First Anodizing Treatment A second-stage anodizing treatment was performed by using the anodizing apparatus for direct current electrolysis having the structure shown in FIG. Anodizing treatment was performed under the conditions shown in Table 1 to form an anodized film having a predetermined film thickness.
  • An undercoat liquid (1) having the following composition was applied on the above support so that the dry coating amount was 20 mg / m 2 , and dried in an oven at 100 ° C. for 30 seconds to prepare a support having an undercoat layer.
  • An overcoat layer (including a hydrophobic part) of 1) was formed to obtain a lithographic printing plate precursor.
  • ⁇ Overcoat layer coating liquid> -Poval PVA105 (manufactured by Kuraray Co., Ltd., saponification degree of 80% or more): 0.6 parts by mass-PEG4000 (manufactured by Tokyo Chemical Industry Co., Ltd.): 0.39 parts by mass-Surfactant (rapizole A-80, Japanese) Oil Co., Ltd .: 0.01 parts by mass Water: 10 parts by mass
  • the measurement was performed by a SCE (regular reflection light removal) method using a spectrophotometer CM2600d manufactured by Konica Minolta Co., Ltd. and operation software CM-S100W. Chromogenic uses the L * a * b * color system of L * value (lightness) was evaluated by the difference ⁇ L between the L * values of the L * value and the unexposed portions of the exposed portion.
  • Table 1 shows the numerical value of ⁇ L. The larger the value of ⁇ L, the better the color developability. The larger the value of ⁇ L after 2 hours of exposure (the numerical value described in the column of "Color developability (after 2 hours)" in the table), the more excellent the color developability with exposure. Further, it can be said that the larger the value of ⁇ L, the better the plate inspection property.
  • the lithographic printing plate precursor thus obtained was exposed with a Luxel PLATESETTER T-6000III manufactured by FUJIFILM Corporation equipped with an infrared semiconductor laser under the conditions of an outer drum rotation speed of 1,000 rpm, a laser output of 70% and a resolution of 2,400 dpi.
  • the exposed image contained a solid image, a 50% halftone dot chart of a 20 ⁇ m dot FM screen, and a non-image portion.
  • the obtained exposed lithographic printing plate precursor was mounted on the plate cylinder of a printing machine LITHRONE 26 manufactured by Komori Corporation without developing.
  • the image recording layer was gradually worn away and the ink acceptability was lowered, so that the ink density on the printing paper was lowered.
  • the number of copies printed when the value measured by x-lite (manufactured by x-lite) of the halftone dot area ratio of the 3% halftone dot of the FM screen in the printed matter is 5% lower than the measured value of the 100th printed sheet As a result, the UV printing durability was evaluated.
  • the lithographic printing plate precursor thus obtained was exposed with a Luxel PLATESETTER T-6000III manufactured by FUJIFILM Corporation equipped with an infrared semiconductor laser under conditions of an outer drum rotation speed of 1,000 rpm, a laser output of 70% and a resolution of 2,400 dpi.
  • the exposed image contained a solid image, a 50% halftone dot chart of a 20 ⁇ m dot FM screen, and a non-image portion.
  • the obtained exposed original plate was mounted on the plate cylinder of a printing machine LITHRONE 26 manufactured by Komori Corporation without developing.
  • the number of printing sheets required until the on-press development of the unexposed area of the image recording layer on the printing machine was completed and ink was not transferred to the non-image area was measured as the on-press developability. It can be said that the smaller the number of sheets, the better the on-press developability.
  • Tables 2 to 4 The unit of the addition amount of each component in Tables 2 to 4 is parts by mass.
  • “ ⁇ ” means that the corresponding component is not included.
  • the details of the compounds shown in Tables 2 to 4 are as follows.
  • IR-1 to IR-9 Infrared absorbing agent represented by the above formula 1-1 (specific infrared absorbing agent)
  • IR-11 An infrared absorbing agent which is not decomposed by heat or infrared exposure shown below.
  • TsO ⁇ in the following compound represents a tosylate anion
  • Ph represents a phenyl group.
  • M-1 Compound below, molecular weight 423.58, ethylenically unsaturated bond equivalent 141.13, ClogP value 2.59
  • M-2 compound below, molecular weight 1,217.23, ethylenically unsaturated bond equivalent 121.72, ClogP value 5.92
  • M-3 compound below, molecular weight 578.57, ethylenically unsaturated bond equivalent weight 96.43, ClogP value 5.08
  • P-1 to P-10 Specific binder polymers shown below. In the following structural units, subscripts a to d in parentheses represent the content (mass ratio) of each structural unit.
  • Acrylic resin polymethylmethacrylate (PMMA), manufactured by Aldrich, Mw: about 120,000 The weight average molecular weights (Mw) of P-1 to P-10 were all 3,000 to 300,000.
  • the conversion to graft copolymer was> 98% based on determination of percent non-volatiles.
  • the PEGMA / styrene / acrylonitrile weight ratio was 10: 9: 81 and the n-propanol / water ratio was 80:20.
  • the number average particle diameter of the polymer particles was 200 nm.
  • the number average particle diameter is an average value obtained by taking an electron microscope photograph of polymer particles and measuring 5,000 equivalent circle diameters of the particles in total on the photograph.
  • the equivalent circle diameter means the diameter of a circle having the same area as the projected area of a particle on a photograph.
  • D-1 to D-6 Compounds shown below Bu in the compounds below represents an n-butyl group. Further, the HOMO of D-6 is ⁇ 5.905 eV and the LUMO is ⁇ 3.250 eV.
  • the lithographic printing plate precursors of Examples 1-1 to 1-18 and 2-1 to 2-18, which are lithographic printing plate precursors according to the present disclosure, contain UV ink more than the lithographic printing plate precursors of Comparative Examples 1 to 3. It can be seen that a lithographic printing plate excellent in printing durability can be obtained even when used. Further, it can be seen that the lithographic printing plate precursors of Examples 2-1 to 2-18, which are lithographic printing plate precursors according to the present disclosure, are excellent in color developability, color developability after exposure, and on-press developability.
  • 12a, 12b Aluminum support
  • 14 Undercoat layer
  • 16 Image recording layer
  • 20a, 20b Anodized film
  • 22a, 22b Micropore
  • 24 Large diameter hole portion
  • 26 Small diameter hole portion
  • D Large Depth of diameter hole part
  • 614 electrolytic treatment tank
  • 616 aluminum plate
  • 618, 26 electrolytic solution
  • 620 power supply electrode
  • 622, 628 roller
  • 624 Nip roller
  • 630 electrolytic electrode
  • 632 tank wall
  • 634 DC power supply

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Abstract

L'invention concerne une plaque originale de plaque d'impression lithographique ayant une couche d'enregistrement d'image sur un corps de support, la couche d'enregistrement d'image contenant un absorbant infrarouge représenté par la formule 1-1, un initiateur de polymérisation et un composé polymérisable. La description spécifie les détails de R1, R11-R18, n11-n14, L, Za, A1 et A2 dans les formules 1-1 et 2.
PCT/JP2019/042872 2018-10-31 2019-10-31 Plaque originale de plaque d'impression lithographique, procédé de production de plaque d'impression lithographique et procédé d'impression lithographique WO2020090996A1 (fr)

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