EP0978375A3 - Radiation-sensitive mixture comprising IR-absorbing, anionic cyanine dyes and recording material prepared therewith - Google Patents

Radiation-sensitive mixture comprising IR-absorbing, anionic cyanine dyes and recording material prepared therewith Download PDF

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Publication number
EP0978375A3
EP0978375A3 EP99114553A EP99114553A EP0978375A3 EP 0978375 A3 EP0978375 A3 EP 0978375A3 EP 99114553 A EP99114553 A EP 99114553A EP 99114553 A EP99114553 A EP 99114553A EP 0978375 A3 EP0978375 A3 EP 0978375A3
Authority
EP
European Patent Office
Prior art keywords
oder
und
alkylamino
eine
nitro
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP99114553A
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German (de)
French (fr)
Other versions
EP0978375B1 (en
EP0978375A2 (en
Inventor
Otfried Dipl.-Ing. Gaschler
Andreas Dr. Elsässer
Fritz-Feo Dr. Grabley
Jörg Dr. Jung
Engelbert Dr. Pliefke
Hans-Joachim Dr. Schlosser
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Agfa Gevaert NV
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Agfa Gevaert AG
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Filing date
Publication date
Application filed by Agfa Gevaert AG filed Critical Agfa Gevaert AG
Publication of EP0978375A2 publication Critical patent/EP0978375A2/en
Publication of EP0978375A3 publication Critical patent/EP0978375A3/en
Application granted granted Critical
Publication of EP0978375B1 publication Critical patent/EP0978375B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • 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
    • 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
    • B41C1/1016—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 characterised by structural details, e.g. protective layers, backcoat layers or several imaging layers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41C—PROCESSES FOR THE MANUFACTURE OR REPRODUCTION OF PRINTING SURFACES
    • B41C2201/00—Location, type or constituents of the non-imaging layers in lithographic printing formes
    • B41C2201/02—Cover layers; Protective layers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41C—PROCESSES FOR THE MANUFACTURE OR REPRODUCTION OF PRINTING SURFACES
    • B41C2201/00—Location, type or constituents of the non-imaging layers in lithographic printing formes
    • B41C2201/14—Location, type or constituents of the non-imaging layers in lithographic printing formes characterised by macromolecular organic compounds, e.g. binder, adhesives
    • 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
    • B41C2210/02—Positive working, i.e. the exposed (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
    • B41C2210/06—Developable by an alkaline 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
    • B41C2210/20—Preparation or type or constituents of the imaging layers, in relation to lithographic printing forme preparation characterised by inorganic additives, e.g. pigments, salts
    • 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
    • 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
    • B41C2210/24—Preparation or type or constituents of the imaging layers, in relation to lithographic printing forme preparation characterised by a macromolecular compound or binder obtained by reactions involving carbon-to-carbon unsaturated bonds, e.g. acrylics, vinyl polymers
    • 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
    • B41C2210/26—Preparation or type or constituents of the imaging layers, in relation to lithographic printing forme preparation characterised by a macromolecular compound or binder obtained by reactions not involving carbon-to-carbon unsaturated bonds
    • B41C2210/262—Phenolic condensation polymers, e.g. novolacs, resols

Landscapes

  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Thermal Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Materials For Photolithography (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)
  • Printing Plates And Materials Therefor (AREA)
  • Thermal Transfer Or Thermal Recording In General (AREA)

Abstract

Beschrieben ist ein positiv arbeitendes, strahlungsempfindliches Gemisch, das ein in Wasser unlösliches, in wäßrig-alkalischer Lösung dagegen lösliches oder zumindest quellbares, organisches, polymeres Bindemittel und mindestens einen IR-absorbierenden Farbstoff enthält, dadurch gekennzeichnet, daß der IR-absorbierende Farbstoff ein anionischer Cyaninfarbstoff der Formel I ist

Figure 80000001
worin

n
2 oder 3 ist
R1 bis R8
unabhängig voneinander ein Wasserstoff- oder Halogenatom, eine Sulfonat-, Carboxylat-, Phosphonat-, Hydroxy-, (C1-C4)Alkoxy-, Nitro-, Amino-, (C1-C4)Alkylamino-, Di(C1-C4)alkylaminogruppe oder eine (C6-C10)Arylgruppe, die gegebenenfalls ihrerseits mit einem oder mehreren Halogenatomen und/oder einer oder mehreren Sulfonat-, Carboxylat-, Phosphonat-, Hydroxy-, (C1-C4)Alkoxy-, Nitro-, Amino-, (C1-C4)Alkylamino- und/oder Di(C1-C4)alkylaminogruppen substituiert ist, darstellen,
R9 und R10
unabhängig voneinander eine geradkettige oder verzweigte (C1-C6)Alkyl-, eine (C7-C16)Aralkyl- oder eine (C6-C10)Arylgruppe, die jeweils gegebenenfalls ihrerseits mit einem oder mehreren Halogenatomen und/oder einer oder mehreren Sulfonat-, Carboxylat-, Phosphonat-, Hydroxy-, (C1-C4)Alkoxy-, Nitro-, Amino-, (C1-C4)Alkylamino- und/oder Di(C1-C4)alkylaminogruppen substituiert sind, darstellen,
Z1 und Z2
unabhängig voneinander ein Schwefelatom, eine Di(C1-C4)alkyl-methylengruppe oder eine Ethen-1,2-diylgruppe darstellen und
X-
ein Kation darstellt,
mit der Maßgabe, daß der Farbstoff 2 bis 4 Sulfonat-, Carboxylat- und/oder Phosphonatgruppen, insgesamt jedoch nicht mehr als zwei Sulfonatgruppen enthält. Offenbart ist daneben ein tageslichtunempfändliches, IR-bebilderbares Aufzeichnungsmaterial mit einem Träger und einer Schicht aus dem Gemisch. Nach bildmäßigem Bestrahlen, insbesondere mit IR-Laserstrahlen, und Entwickeln mit einer wäßrig-alkalischen Lösung entsteht daraus eine Offsetdruckplatte.A positive-working, radiation-sensitive mixture is described which contains an organic polymeric binder which is insoluble in water but soluble or at least swellable in aqueous alkaline solution and at least one IR-absorbing dye, characterized in that the IR-absorbing dye is an anionic Is cyanine dye of formula I.
Figure 80000001
wherein
n
Is 2 or 3
R 1 to R 8
independently of one another a hydrogen or halogen atom, a sulfonate, carboxylate, phosphonate, hydroxy, (C 1 -C 4 ) alkoxy, nitro, amino, (C 1 -C 4 ) alkylamino, di (C 1 -C 4 ) alkylamino group or a (C 6 -C 10 ) aryl group, which in turn may optionally have one or more halogen atoms and / or one or more sulfonate, carboxylate, phosphonate, hydroxy, (C 1 -C 4 ) Alkoxy, nitro, amino, (C 1 -C 4 ) alkylamino and / or di (C 1 -C 4 ) alkylamino groups are substituted,
R 9 and R 10
independently of one another are a straight-chain or branched (C 1 -C 6 ) alkyl, a (C 7 -C 16 ) aralkyl or a (C 6 -C 10 ) aryl group, each of which in turn optionally has one or more halogen atoms and / or one or more sulfonate, carboxylate, phosphonate, hydroxy, (C 1 -C 4 ) alkoxy, nitro, amino, (C 1 -C 4 ) alkylamino and / or di (C 1 -C 4 ) alkylamino groups are substituted,
Z 1 and Z 2
independently represent a sulfur atom, a di (C 1 -C 4 ) alkyl-methylene group or an ethene-1,2-diyl group and
X -
represents a cation
with the proviso that the dye contains 2 to 4 sulfonate, carboxylate and / or phosphonate groups, but in total not more than two sulfonate groups. In addition, a daylight-insensitive, IR-imageable recording material with a support and a layer of the mixture is disclosed. After imagewise irradiation, in particular with IR laser beams, and development with an aqueous alkaline solution, an offset printing plate is obtained.

EP99114553A 1998-08-01 1999-07-24 Radiation-sensitive mixture comprising IR-absorbing, anionic cyanine dyes and recording material prepared therewith Expired - Lifetime EP0978375B1 (en)

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DE19834745A DE19834745A1 (en) 1998-08-01 1998-08-01 Radiation-sensitive mixture with IR-absorbing, anionic cyanine dyes and recording material produced therewith
DE19834745 1998-08-01

Publications (3)

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EP0978375A2 EP0978375A2 (en) 2000-02-09
EP0978375A3 true EP0978375A3 (en) 2001-09-12
EP0978375B1 EP0978375B1 (en) 2004-10-20

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US (1) US6238838B1 (en)
EP (1) EP0978375B1 (en)
JP (1) JP2000206695A (en)
DE (2) DE19834745A1 (en)

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US6824879B2 (en) 1999-06-10 2004-11-30 Honeywell International Inc. Spin-on-glass anti-reflective coatings for photolithography
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US7129021B2 (en) * 1999-12-17 2006-10-31 Creo Srl Polymer system with switchable physical properties and its use in direct exposure printing plates
JP4098483B2 (en) * 2001-03-12 2008-06-11 富士フイルム株式会社 Planographic printing plate precursor
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US9085698B2 (en) 2011-09-23 2015-07-21 Illumina Cambridge Limited Dyes for labelling molecular ligands
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EP3194502A4 (en) 2015-04-13 2018-05-16 Honeywell International Inc. Polysiloxane formulations and coatings for optoelectronic applications
GB201508858D0 (en) 2015-05-22 2015-07-01 Illumina Cambridge Ltd Polymethine compounds with long stokes shifts and their use as fluorescent labels
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Also Published As

Publication number Publication date
DE59910884D1 (en) 2004-11-25
US6238838B1 (en) 2001-05-29
JP2000206695A (en) 2000-07-28
EP0978375B1 (en) 2004-10-20
DE19834745A1 (en) 2000-02-03
EP0978375A2 (en) 2000-02-09

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