EP0978376B1 - Produit d'enregistrement sensible aux rayons actiniques contenant des colorants cyanines absorbant des rayons infrarouges et ayant une structure bétaine ou ayant une structure bétaine et contenant un anion, et matériau pour l'enregistrement préparé à partir de ce produit - Google Patents

Produit d'enregistrement sensible aux rayons actiniques contenant des colorants cyanines absorbant des rayons infrarouges et ayant une structure bétaine ou ayant une structure bétaine et contenant un anion, et matériau pour l'enregistrement préparé à partir de ce produit Download PDF

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Publication number
EP0978376B1
EP0978376B1 EP99114554A EP99114554A EP0978376B1 EP 0978376 B1 EP0978376 B1 EP 0978376B1 EP 99114554 A EP99114554 A EP 99114554A EP 99114554 A EP99114554 A EP 99114554A EP 0978376 B1 EP0978376 B1 EP 0978376B1
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Prior art keywords
recording material
radiation
sensitive recording
material according
betaine structure
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EP99114554A
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German (de)
English (en)
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EP0978376A3 (fr
EP0978376A2 (fr
Inventor
Otfried Dipl.-Ing. Gaschler
Andreas Dr. Elsässer
Jörg Dr. Jung
Hans-Joachim Dr. Schlosser
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Agfa Gevaert NV
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Agfa Gevaert NV
Agfa Gevaert AG
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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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
    • Y10S430/1055—Radiation sensitive composition or product or process of making
    • Y10S430/106—Binder containing
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
    • Y10S430/1055—Radiation sensitive composition or product or process of making
    • Y10S430/127—Spectral sensitizer containing
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/145—Infrared

Definitions

  • the invention relates to a positive-working, radiation-sensitive The recording material Mixture, wherein the mixture is a water-insoluble, in aqueous alkaline solution against it soluble, organic, polymeric binder and an IR-absorbing Contains dye or pigment.
  • the mixture concerns a procedure for the production of lithographic printing plates using a recording material with a Carrier and a layer of this mixture.
  • the layer has a high Photosensitivity in the IR range, so that the recording material for direct imaging using the computer-to-plate (CTP) method is.
  • the recording material according to WO 96/20429 comprises a layer with IR-absorbing carbon black pigments, 1,2-naphthoquinone-2-diazide-sulfonic acid ester or -carboxylic acid ester and a phenolic resin.
  • the 1,2-naphthoquinone-2-diazide-sulfonic acid or carboxylic acid may also be directly linked to the hydroxy groups be esterified of phenolic resin.
  • the layer is initially full surface exposed with UV rays and then imagewise with IR laser beams. Due to the influence of the IR rays, certain areas of the the UV radiation solubilized layer again insoluble. It is about So a negative working system. The processing of the material is thus relatively expensive.
  • EP-A 0 784 233 likewise describes a negative-working mixture, a) novolac and / or polyvinylphenol, b) amino compounds for Hardening of component a), c) a cyanine and / or polymethine dye, the absorbed in the near IR region, and d) photochemical acid generator contains.
  • EP-A 908 307 a process for the preparation of a described positive lithographic printing plate, after which a picture generating element is imagewise exposed to IR rays, wherein the image forming element comprises a lithographic support a hydrophilic surface comprises and the support with a a polymer-containing first layer and a second IR-sensitive Cover layer is provided.
  • WO 97/39894 describes layers which are solution-inhibiting Supplements included. Such additives reduce the solubility of the unexposed areas of the layer during development in aqueous-alkaline Solutions.
  • the additives are next to various pigments in particular cationic compounds, especially dyes and cationic IR absorbers such as quinoline cyanine dyes, benzothiazole cyanine dyes or merocyanines.
  • these layers become 5 to 20 seconds long heated to 50 to 100 ° C, the additives lose their inhibiting again Effect.
  • the positive working mixture disclosed in EP-A 0 823 327 contains as IR absorbers cyanine, polymethine, squarylium, croconium, pyrylium or Thiopyrylium dyes. Most of these dyes are cationic and show an inhibiting effect. In addition, many of them are halogen-containing. Under unfavorable conditions it can cause environmentally harmful decomposition products arise. Also disclosed are some betaine dyes and an anionic dye (Compound S-9 on page 7). After However, layer drying causes this anionic dye due to its high number of sulfonate groups usually crystallize or Failures of coating components, resulting in significantly worse properties the IR-sensitive layer leads and a lack of layer cosmetics causes.
  • the disadvantage of the layer compositions known from the prior art is that the increase in solubility caused by reheating is reached, is reversible after storage at room temperature. Will one Pressure plate not immediately after heating (e.g. further processed, so the development characteristics, what to change Reproduction problems in the processing of the recording materials can lead. As already mentioned, can be at unfavorable Conditions even by halogen-containing cationic additives environmentally harmful decomposition products arise.
  • the object of the invention was a radiation-sensitive recording material of the above to provide the type described which contains neither diazonium compounds, still heat or acid curing amino compounds, but also no Contains silver halide compounds and in addition to an imagewise exposure and development no additional work such as reheating or Burning required.
  • the chain with the conjugated double bonds is generally 3 to 15 carbon atoms long.
  • a delocalized ⁇ -electron system extends usually also between the two bicyclic ring systems.
  • Preferred are dyes of symmetrical construction, i. those in which substituted the (partially) aromatic radicals in the formula (I) in the same way and where n m. They are synthetically also more accessible.
  • the said (C 1 -C 4 ) alkoxy group is preferably a methoxy or ethoxy group, while the (C 7 -C 16 ) aralkyl group is preferably a benzyl group.
  • the halogen atoms are generally chlorine, bromine or iodine atoms.
  • R 11 and R 12 are preferably methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec- butyl, tert- butyl, phenyl or naphthalene-1 or 2-yl groups, where the two radicals are particularly preferably identical and likewise particularly preferably methyl groups.
  • betainic refers to the compounds of the formula (I) because, in addition to the quaternary nitrogen atom of the 3H-indolium, quinolinium or benzothiazolium ring, they contain the pyrimidine-2,4,6-trione enolate group represented in the formula.
  • carboxylate, sulfonate and / or phosphonate groups may be present, so that the compounds may be anionic-betainic as a whole. The number of these anionic groups should generally not exceed 5.
  • the counterions of these anionic groups are generally alkali or alkaline earth cations, especially sodium or potassium ions, but also ammonium ions or mono-, di-, tri- or tetraalkylammonium ions.
  • the number thereof is less than or at most as great as that of the carboxylate, sulfonate and / or phosphonate groups, so that the dye remains betainic-anionic or betainic.
  • the ring formed to include Q is preferably a (C 4 -C 7 ) cycloalkene, more preferably cyclopentene.
  • the said 4- to 7-membered ring may also be substituted, especially with halogen atoms, hydroxy groups, alkoxy groups, nitro groups, amino groups, alkylamino groups, dialkylamino groups, carboxy groups, sulfo groups, phosphonic acid groups.
  • the heteroatoms are in particular nitrogen, oxygen and / or sulfur atoms. There may also be several heteroatoms in the ring.
  • IR-absorbing betainic or betainic-anionic cyanine dyes F1 to F3 listed below the cationic dye F4 * was used for comparison purposes and is therefore marked with *.
  • the anionic betainic IR-absorbing Additions no solubility-inhibiting effect on the layer exercise, but usually the dissolution or swelling rate in aqueous-alkaline Promote developers.
  • Betaine IR-absorbing additives can have an inhibitory effect, but behave after a short-term Reheating almost inert, i. they do not experience any increase in solubility in aqueous-alkaline developers.
  • the proportion of the IR absorbing dye is generally 0.2 to 30 wt .-%, preferably 0.5 to 20 wt .-%, particularly preferably 0.6 to 10 Wt .-%, each based on the total weight of the solids Mixture.
  • suitable IR absorbing dyes Not only narrow IR areas can be used, but the whole Wavelength range of the near IR spectrum. To cover the IR range from 700 to 1200 nm, in particular from 800 to 1100 nm, are in usually requires at least two IR-absorbing dyes.
  • the organic polymeric binder is preferably a binder having acidic groups whose pK s is less than 13. This ensures that the layer is soluble or at least swellable in aqueous-alkaline developers.
  • the binder is a polymer or polycondensate, for example a polyester, polyamide, polyurethane or polyurea. Also particularly suitable are polycondensates and polymers having free phenolic hydroxyl groups, as obtained, for example, by reacting phenol, resorcinol, a cresol, a xylenol or a trimethylphenol with aldehydes - especially formaldehyde - or ketones.
  • condensation products of sulfamoyl or carbamoyl-substituted aromatics and aldehydes or ketones are also suitable.
  • Polymers of bis-methylol-substituted ureas, vinyl ethers, vinyl alcohols, vinyl acetals or vinyl amides and polymers of phenyl acrylates and copolymers of hydroxyphenyl maleimides are also suitable.
  • polymers having vinyl aromatic units, N-aryl (meth) acrylamides or aryl (meth) acrylates may be mentioned, where these units may each have one or more carboxy groups, phenolic hydroxyl groups, sulfamoyl or carbamoyl groups.
  • the polymers may additionally contain units of other monomers which do not have acidic units.
  • Such units are vinylaromatics, methyl (meth) acrylate, phenyl (meth) acrylate, benzyl (meth) acrylate, methacrylamide or acrylonitrile.
  • the proportion of the binder is generally 40 to 99.8 wt .-%, preferably 70 to 99.4% by weight, particularly preferably 80 to 99% by weight, each based on the total weight of the nonvolatile constituents of the Mixture.
  • the polycondensation product is a Novolak, preferably a cresol / formaldehyde or a cresol / xylenol / formaldehyde novolak, the proportion of novolak being at least 50% by weight, preferably at least 80 wt .-%, is, in each case based on the Total weight of all binders.
  • Recording material can finally also by soluble or finely divided, non-inhibiting, soluble or dispersible dyes, which practically do not absorb in the IR range, be influenced or controlled. Suitable for this purpose are in particular Triarylmethane, azine, oxazine, thiazine and xanthene dyes.
  • the share of optionally additionally present in the mixture of dyes generally 0.01 to 30 wt .-%, preferably 0.05 to 10 wt .-%, respectively based on the total weight of the nonvolatile constituents of the Mixture.
  • the mixture may contain other additives, the not layer-inhibiting, contain, e.g. Carbon black pigments as additional IR absorbers, surfactants (preferably fluorine-containing surfactants or silicone surfactants), Polyalkylene oxides for controlling the acidity of acidic units and Low molecular weight compounds with acidic units to increase the Development speed.
  • the mixture contains no ingredients when exposed to radiation in the ultraviolet or visible region of the Spectrum could have an influence on the daylight sensitivity.
  • Binders and IR-absorbing, betainic or betainic-anionic Cyanine dye are present as a mixture.
  • the recording material with a support and a positive-working, IR-sensitive layer is characterized in that the layer of the described Mixture exists.
  • the mixture can also be used for other purposes, e.g. as a photoresist.
  • a solvent mixture containing the components of Mixture does not react irreversibly.
  • the solvent is on the intended Coating method, the layer thickness, the composition of the layer, and to adjust the drying conditions.
  • chlorinated Hydrocarbons such as trichlorethylene or 1,1,1-trichloroethane
  • alcohols such as
  • the support in the recording material according to the invention is preferably an aluminum foil or a composite of an aluminum and a polyester film.
  • the aluminum surface is preferably roughened, anodized and hydrophilized with a compound containing at least one Phosphonic acid or phosphonate unit contains. Before the roughening can a degreasing and pickling with lyes and a mechanical and / or chemical pre-roughening done.
  • the thickness of the IR-sensitive layer is generally 1.0 to 5.0 microns, preferably 1.5 to 3.0 microns.
  • a cover layer In order to protect the surface of the recording material, in particular before mechanical action, can also applied a cover layer become. It generally consists of at least one water-soluble polymeric binders such as polyvinyl alcohol, polyvinylpyrrolidone, partially hydrolyzed Polyvinyl acetates, gelatin, carbohydrates or hydroxyethyl cellulose and is prepared from an aqueous solution or dispersion, optionally small amounts, i. less than 5 wt .-%, based on the Total weight of coating solvent for the topcoat may contain organic solvents.
  • the thickness of the cover layer is up to 5.0 microns, preferably 0.1 to 3.0 microns, more preferably 0.15 to 1.0 microns.
  • the subject matter of the present invention is a process for Production of a planographic printing plate in which the recording material according to the invention irradiated imagewise with infrared radiation and then in a conventional aqueous-alkaline developer at a temperature of 20 to 40 ° C is developed.
  • aqueous-alkaline developer at a temperature of 20 to 40 ° C is developed.
  • general-purpose developers can be used for positive plates.
  • Preferred alkali oxides are Na 2 O and K 2 O, as well as mixtures thereof.
  • the developer may contain other components, such as buffer substances, complexing agents, defoamers, organic solvents in small amounts, corrosion inhibitors, dyes, surfactants and / or hydrotropes.
  • the development is preferred at temperatures of 20 to 40 ° C in mechanical processing equipment.
  • Alkali silicate solutions used with alkali contents of 0.6 to 2.0 mol / l. These Solutions can have the same silica / alkali oxide ratio as the Developers own (but usually it is lower) and also others Supplements included.
  • the required amounts of regenerate must be on the used development devices, daily plate throughputs, image parts etc. are tuned and are generally from 1 to 50 ml per Square meters of recording material.
  • a scheme of addition can For example, via the Leitwerttul done, as in EP-A 0 556 690 described.
  • the recording material of the present invention may be subsequently added, if necessary with a suitable correction agent or preservative be treated.
  • the coating solutions thus prepared were roughened in hydrochloric acid, anodized in sulfuric acid and hydrophilized with polyvinylphosphonic acid Applied aluminum foils. After 2 min drying at 100 ° C was the Layer thickness at 1.9 +/- 0.1 microns.
  • Table 1a shows that Examples 1b to 1e in some embodiments have a solubility-inhibiting effect on the layer, in each case Comparison to a layer without IR dyes (1a *).
  • Tables 1b and 1c clearly show that only the comparative example 1b *, which contains a cationic IR-absorbing dye, after reheating a solubility increase in an aqueous-alkaline solution experiences.
  • Coating solutions were prepared from 0.87 gt meta- / para- cresol / formaldehyde novolac, 0.10 Gt polyhydroxystyrene 4.50 gt tetrahydrofuran, 1,80 Gt ethylene glycol monoalkyl, 2,70 Gt Methanol and 0.03 Gt IR absorber (see Table 2).
  • the development was carried out in a conventional processor at a flow rate of 0.8 m / min and a temperature of 23 ° C with a potassium silicate developer, the K 2 SiO 3 (normality 0.8 mol / l in water) and 0.2% O , O'-bis-carboxymethyl-polyethylene glycol-1000 and 0.4% pelargonic acid.
  • Table 3 shows the image reproduction of halftone dots of a test wedge. example Reproduction of the percent center points) Playback of the open grid depths 2a * no development no development 2 B* 4 97 2c 3 98 2d 3 99 2e 2 98
  • the development was carried out in a conventional processor at a flow rate of 0.8 m / min and a temperature of 23 ° C with a potassium silicate developer, the K 2 SiO 3 (normality 0.8 mol / l in water) and 0.2% O , O'-bis-carboxymethyl-polyethylene glycol-1000 and 0.4% pelargonic acid.
  • Developmental behavior after exposure to daylight example 0 min exposure 1 h exposure 1 week exposure 3a By default By default By default By default 3b * By default total layer removal ----
  • the table shows that the diazo-containing layer is completely removed during development was, if previously 1 hour (or less) of daylight on the Recording material had acted.
  • the recording material according to the invention was insensitive to daylight and settled even if it is a week or more Daylight was exposed.
  • This example demonstrates the advantage of IR dyes with and without indicator dyes in comparison to soot-sensitized recording materials in Reference to mechanical surface attack.
  • Coating solutions were prepared from 0.72% meta / para- cresol / formaldehyde novolac, 0.10 Gt Copolymer of (2-hydroxy-phenyl) -methacrylate and methyl methacrylate (M w : 4,000) and 0.05 gt 2,4-dihydroxy-benzophenone as well 0.02% Flexoblue 630 from BASF (only in layers 4b and 4d *) or 0.08 Gt F 3 (only in layers 4a and 4b) or 0.04 Gt Carbon black pigment type HCC from Grolman (only in layers 4c * and 4d *).
  • the recording materials were then placed in an external drum imagesetter exposed to infrared radiation. It was also in the previous Examples used Nd-YAG lasers with a power of 7.0 W, one Write speed of 120 rpm and a beam width of 10 ⁇ m used.
  • the recording materials were in a hardness tester pretreated. This rolled a rubber wheel with a diameter of about 1 to 2 cm and a tread width of about 1 mm beyond that testing material. With the help of weights, the contact pressure was like from the Table visible.
  • the development was carried out in a conventional processor at a flow rate of 0.8 m / min and a temperature of 23 ° C with a potassium silicate developer, the K 2 SiO 3 (normality 0.8 mol / l in water) and 0.2% O , O'-bis-carboxymethyl-polyethylene glycol-1000 and 0.4% pelargonic acid.
  • Table 5 shows the results after treatment of the recording materials with the hardness tester. Corresponding to the mechanical sensitivity of the coating surface, imprint marks (referred to in the table as "traces") appear on the material. example Applying mass to an impeller [N] 0.5 1 2 5 4a - traces traces traces 4b - - - traces 4c * traces traces traces traces 4d * - - traces traces
  • Recording materials with additional indicator dye are less sensitive to mechanical effects.
  • the table also shows that IR-sensitized recording materials are less sensitive to footprints as soot-pigmented.
  • Example 5 shows the influence of IR absorber mixtures on recording materials.
  • a coating solution was prepared 0.85 Gt meta- / para- cresol / formaldehyde novolac, 0.06 Gt Styrene / acrylate copolymer (M w 6500, acid number 205), 4.50 gt tetrahydrofuran, 1,80 Gt ethylene glycol monoalkyl, 2,70 Gt Methanol.
  • the respective coating solutions were applied to aluminum foils, previously roughened in hydrochloric acid, anodized in sulfuric acid and had been hydrophilized with polyvinylphosphonic acid. After drying for 2 min at 100 ° C, the layer thickness was 2 microns.
  • the development was carried out in a conventional processor at a flow rate of 1.0 m / min and a temperature of 23 ° C with a potassium silicate developer, the K 2 SiO 3 (normality 0.8 mol / l in water) and 0.2% O , O'-bis-carboxymethyl-polyethylene glycol-1000 and 0.4% pelargonic acid.
  • K 2 SiO 3 normality 0.8 mol / l in water
  • O O'-bis-carboxymethyl-polyethylene glycol-1000 and 0.4% pelargonic acid.
  • the table shows that by suitable mixing of IR absorbers a Sensitization in the entire range of 830 nm to 1064 nm is possible.

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  • 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)

Claims (15)

  1. Matériau d'enregistrement sensible au rayonnement, qui présente un substrat comportant une surface hydrophile et une couche sensible au rayonnement disposée sur cette surface, cette couche contenant un mélange qui contient un liant polymère organique insoluble dans l'eau, mais soluble ou au moins apte à gonfler dans une solution alcaline aqueuse, et au moins un colorant absorbant l'infrarouge, caractérise en ce que le colorant absorbant l'infrarouge est un colorant de cyanine bétaïnique ou bétaïnique-anionique répondant à la formule (I)
    Figure 00370001
    dans laquelle
    R1 à R8
    représentent indépendamment l'un de l'autre, un atome d'hydrogène ou un atome d'halogène, un groupe sulfonate, un groupe carboxylate, un groupe phosphonate, un groupe hydroxyle, un groupe alcoxy en C1-C4, un groupe nitro, un groupe amino, un groupe alkyl(en C1-C4)amino, un groupe dialkyl(en C1-C4) amino ou un groupe aryle en C6-C10, les groupes en question pouvant, le cas échéant, quant à eux, porter un ou plusieurs substituants halogéno et/ou un ou plusieurs substituants sulfonate, carboxylate, phosphonate, hydroxyle, alcoxy en C1-C4, nitro, amino, alkyl(en C1-C4)amino et/ou dialkyl(en C1-C4)amino,
    R9 et R10
    représentent indépendamment l'un de l'autre, un groupe alkyle en C1-C6 à chaíne droite ou ramifiée, un groupe aralkyle en C7-C16 ou un groupe aryle en C6-C10, les groupes en question pouvant, le cas échéant, quant à eux, porter un ou plusieurs substituants halogèno et/ou un ou plusieurs substituants sulfonate, carboxylate, phosphonate, hydroxyle, alcoxy en C1-C4, nitro, amino, alkyl(en C1-C4)amino et/ou dialkyl(en C1-C4) amino,
    R11 et R12
    représentent indépendamment l'un de l'autre, un groupe alkyle en C1-C4 ou un groupe aryle en C6-C10, les groupes en question pouvant, le cas échéant, quant à eux, être substitués,
    Z1 et Z2
    représentent indépendamment l'un de l'autre, un atome de soufre, un groupe dialkyl(en C1-C4)méthylène ou un groupe éthène-1,2-diyle, et
    A
    représente un atome de carbone ou une chaíne contenant des liaisons doubles conjuguées, qui donne lieu à la formation d'un système délocalisé à électrons π entre un atome d'azote quaternaire du radical 3H-indolium, du radical quinolinium ou du radical benzothiazolium et l'atome d'oxygène de l'énolate du radical de pyrimidine-2,4,6-trione.
  2. Matériau d'enregistrement sensible au rayonnement selon la revendication 1, caractérisé en ce que le colorant absorbant l'infrarouge est un colorant de cyanine bétaïnique ou bétaïnique-anionique répondant à une des formules (II) à (IV) indiquées ci-après :
    Figure 00390001
    Figure 00390002
    Figure 00390003
    dans lesquelles
    n et m
    représentent des nombres entiers de 1 à 8, à condition que n + m = 2 ou plus, et
    Q
    représente les membres requis pour la formation d'un noyau isocyclique ou hétérocyclique, carré à heptagonal.
  3. Matériau d'enregistrement sensible au rayonnement selon la revendication 2, caractérisé en ce que le noyau formé par l'inclusion de Q représente un cycloalcène en C4-C7 de préférence le cyclopentène.
  4. Matériau d'enregistrement sensible au rayonnement selon une ou plusieurs des revendications 1 à 3, caractérisé en ce que le liant contient des groupes acides dont la valeur pKs est inférieure à 13.
  5. Matériau d'enregistrement sensible au rayonnement selon la revendication 4, caractérisé en ce que le liant est un produit de polycondensation de phénols ou de composés aromatiques portant un ou plusieurs substituants sulfamoyle ou carbamoyle avec des aldéhydes ou des cétones, un produit réactionnel de diisocyanates avec des diols ou des diamines ou encore un polymère comprenant des unités de composés vinylaromatiques, de N-aryl(méth)acrylamides ou d'aryl(méth)acrylates, ces unités contenant en outre respectivement un ou plusieurs groupes carboxyle, un ou plusieurs groupes hydroxyle phénoliques, un ou plusieurs groupes sulfamoyle ou carbamoyle.
  6. Matériau d'enregistrement sensible au rayonnement selon la revendication 5, caractérisé en ce que le produit de polycondensation est une novolaque, de préférence une novolaque de crésol/formaldéhyde ou une novolaque de crésol/xylénol/formaldéhyde, la fraction des novolaque représentant de préférence au moins 50 % en poids, de manière particulièrement préférée au moins 80 % en poids, rapportés au poids total de tous les liants.
  7. Matériau d'enregistrement sensible au rayonnement selon une ou plusieurs des revendications 1 à 6, caractérisé en ce que la fraction du liant représente de 40 à 99,8 % en poids, de préférence de 70 à 99,4 % en poids, de manière particulièrement préférée de 80 à 99 % en poids, chaque fois rapportés au poids total des constituants non volatils du mélange.
  8. Matériau d'enregistrement sensible au rayonnement selon la revendication 1, caractérisé en ce que le colorant absorbant l'infrarouge ne subit pas une augmentation de la solubilité après un réchauffement ultérieur de courte durée.
  9. Matériau d'enregistrement sensible au rayonnement selon une ou plusieurs des revendications 1 à 8, caractérisé en ce que la fraction du colorant de cyanine bétaïnique ou bétaïnique-anionique absorbant l'infrarouge, répondant à la formule (I) représente de 0,2 à 30 % en poids, de préférence de 0,5 à 20 % en poids, de manière particulièrement préférée de 0,610 % en poids, chaque fois rapportés au poids total des produits solides du mélange.
  10. Matériau d'enregistrement sensible au rayonnement selon une ou plusieurs des revendications 1 à 9, caractérisé en ce qu'il contient, pour couvrir la région de l'infrarouge proche, c'est-à-dire que la région infrarouge de 700 à 1100 nm, en particulier de 800 à 1100 nm, deux colorants bétaïniques ou bétaïniques-anioniques différents ou plus répondant à la formule I.
  11. Matériau d'enregistrement sensible au rayonnement selon une ou plusieurs des revendications 1 à 10, caractérisé en ce qu'il contient un pigment de noir de carbone qui, de préférence, a été soumis à une dispersion préalable, l'agent de mise en dispersion contenant des groupes hydroxyle phénoliques.
  12. Matériau d'enregistrement sensible au rayonnement selon une ou plusieurs des revendications 1 à 11, caractérisé en ce qu'une couche de recouvrement constituée par au moins un liant polymère soluble dans l'eau est disposée sur la couche sensible au rayonnement, respectivement sur la couche contenant le colorant.
  13. Matériau d'enregistrement sensible au rayonnement selon la revendication 12, caractérisé en ce que le liant polymère soluble dans l'eau est l'alcool polyvinylique, la polyvinylpyrrolidone, de l'acétate de polyvinyle partiellement saponifié, de la gélatine, un hydrate de carbone ou encore de l'hydroxyéthylcellulose.
  14. Matériau d'enregistrement sensible au rayonnement selon une ou plusieurs des revendications 1 à 13, caractérisé en ce que le support est constitué d'une feuille mince en aluminium.
  15. Procédé pour la préparation d'un cliché d'impression, dans lequel un matériau d'enregistrement sensible au rayonnement est exposé en forme d'image à un rayonnement infrarouge, avant d'être développé avec une solution alcaline aqueuse, caractérisé en ce que le matériau d'enregistrement correspond à une ou plusieurs des revendications 1 à 14.
EP99114554A 1998-08-01 1999-07-24 Produit d'enregistrement sensible aux rayons actiniques contenant des colorants cyanines absorbant des rayons infrarouges et ayant une structure bétaine ou ayant une structure bétaine et contenant un anion, et matériau pour l'enregistrement préparé à partir de ce produit Expired - Lifetime EP0978376B1 (fr)

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JP4259685B2 (ja) 2009-04-30
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