WO1991019227A1 - Materiaux photosensibles pour plaques lithographiques - Google Patents

Materiaux photosensibles pour plaques lithographiques Download PDF

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Publication number
WO1991019227A1
WO1991019227A1 PCT/GB1991/000858 GB9100858W WO9119227A1 WO 1991019227 A1 WO1991019227 A1 WO 1991019227A1 GB 9100858 W GB9100858 W GB 9100858W WO 9119227 A1 WO9119227 A1 WO 9119227A1
Authority
WO
WIPO (PCT)
Prior art keywords
dye
light sensitive
phenol
functionality
reaction
Prior art date
Application number
PCT/GB1991/000858
Other languages
English (en)
Inventor
Adelaide Titilayo Adebayo
Gerald Auguotine Power
Barry Jolliffe
Original Assignee
Horsell Plc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Horsell Plc filed Critical Horsell Plc
Publication of WO1991019227A1 publication Critical patent/WO1991019227A1/fr

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Classifications

    • 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
    • G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
    • 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
    • G03F7/022—Quinonediazides
    • G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
    • 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
    • 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
    • B41C2210/26—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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/36—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using a polymeric layer, which may be particulate and which is deformed or structurally changed with modification of its' properties, e.g. of its' optical hydrophobic-hydrophilic, solubility or permeability properties
    • B41M5/368—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using a polymeric layer, which may be particulate and which is deformed or structurally changed with modification of its' properties, e.g. of its' optical hydrophobic-hydrophilic, solubility or permeability properties involving the creation of a soluble/insoluble or hydrophilic/hydrophobic permeability pattern; Peel development

Definitions

  • the invention relates to positive working light sensitive materials which can be used in the production of lithographic printing plates.
  • Light sensitive lithographic plates are produced by applying a light sensitive coating to a suitable support for example a plate of anodised aluminium. When the plate is exposed by light reaction in the coating results in the image areas having a different solubility from the non-image areas. Development with a suitable solvent can then selectively dissolve away the more soluble of the areas.
  • a positive working plate is one in which the exposed, light-struck, areas are more soluble than the unexposed areas.
  • One system which is frequently used to provide a positive working light-sensitive material is a mixture of a quinone diazide with a novolak resin. On exposure light converts the quinone diazide to an indene carboxylic acid which is soluble in and developable by an alkaline aqueous developer of about pH 11.
  • Dyes are often included in the light sensitive materials so that the image can be visibly inspected.
  • the dyes used are of two kinds, those which retain the same colour throughout the exposure and development process and those which change colour when exposed. In the case of the former the image is distinguished from the non-image when dye is selectively removed during development. In the latter case a change in colour occurs on irradiation so that the non-image area is distinguished from the image area.
  • the colour change results from the use of a pH-indicating dye which, in the case where a quinone diazide is used as the light sensitive material, changes colour due to increased acidity caused as the diazide converts to carboxylic acid groups.
  • GB 1347759 describes a positive working material which exhibits a colour change upon exposure to light and which comprises in admixture a diazonium salt, a novolak resin and a hydroxy substituted aryl azo compound which undergoes a colour change in the presence of the acid produced by the diazonium salt on exposure to light.
  • the coating on a positive working lithoplate will be formulated to contain both a permanent dye and a pH indicating dye. In this way there is ' both a constant colour to the coating and a colour change on exposure.
  • Dye containing systems suffer from the drawback that they are not generally suitable for use directly on a freshly sulphuric acid anodised substrate.
  • the dye is absorbed by the substrate and can not be washed off during development. It is necessary for the plate to undergo a post anodic treatment before the coating of light sensitive material and dye is applied so as to pacify the substrate and prevent absorption of the dye on it.
  • Various different post anodic treatments are commonly employed in the industry to achieve this, for example silicating, phosphating and treatment with polycarboxylic acid. These treatments have the effect of sealing the surface of the plate to prevent absorption of dye.
  • a post anodic treatment has the effect of reducing the press durability (run length) of a plate and also involves additional cost because of the extra manufacturing step involved.
  • a method of producing a dye-containing positive working light sensitive material comprising reacting a novolak resin with a dye capable of reacting with phenolic -OH groups on the novolak and a quinone-diazide.
  • a method of producing a dye-containing positive working light sensitive material comprising reacting together a phenol or substituted phenol, a reactive dye and formaldehyde and then reacting the product with a quinone diazide.
  • the present invention thus provides two methods of producing light sensitive materials in which a dye is incorporated directly in the molecule of light sensitive novolak rather than being present as a separate component in a light sensitive composition.
  • light sensitive materials produced according to either of these methods are used as coatings directly on freshly sulphuric acid anodised lithographic plates and subsequently irradiated and developed the background (non-image) areas are not dye stained. It is thought that the extra bulk and large molecular weight of the dye which is bound to the novolak prevents it from being absorbed.
  • the dye-containing novolak is prepared by reacting a pre-prepared novolak resin with both a dye and a quinone diazide.
  • the dye must be one which is capable of reacting with phenolic -OH groups on the novolak.
  • the quinone diazide reacts with other phenolic -OH groups on the novolak.
  • the dye may be a permanent dye or a pH-indicating dye provided it can undergo the necessary reaction. Examples of dyes which have been found to work particularly well in this first method are permanent dyes such as those which contain a cyanuric chloride or ⁇ ulphonyl chloride group. Specific examples are the commercially available Procion dyes such as Procion blue MX-G available from ICI.
  • Novolak resins which may be employed in this embodiment include those commonly used to prepare positive working light sensitive materials. Such novolaks are formed by condensing phenol or substituted phenol with formaldehyde. Specific examples of such novolaks include those based on cresol formaldehyde, such as Bakelite.
  • the dye-containing light sensitive material is prepared by reacting a dye into the polymer chain at the same time as the novolak is formed by reaction of a phenol or substituted phenol with formaldehyde.
  • the dye reacts into the molecule in a different way by co-condensing with the formaldehyde and phenol or substituted phenol.
  • the co-condensed polymer is then reacted with a quinone diazide which reacts with phenolic -OHs of the polymer.
  • This embodiment may be used to produce light sensitive materials containing either permanent or pH indicating dyes.
  • the permanent dyes mentioned above may be used. It is, however, particularly suitable for use with pH indicating dyes, for example phthaleins or sulphophthaleins.
  • a particular example of a sulphophthalein dye which may be employed in this embodiment is Phenol Red.
  • Phenol or substituted phenol compounds which may be employed in this embodiment include those commonly used to produce novolak resins.
  • the quinone diazide used as the light sensitive component of the material includes those conventionally employed in light sensitive coatings for lithoplates, for example a napthaquinone diazide ⁇ ulphonyl chloride. Specific examples include 2-diazo-l-naphthol-4-sulphonyl chloride and 2-diazo-l-naphthol-5-sulphonyl chloride.
  • the present invention includes positive working light sensitive material produced by the methods of the first and second embodiments of the invention.
  • the invention consists of positive working light sensitive material comprising a novolak resin which is functionalised with both a dye and a quinone diazide.
  • This reaction mixture was stirred for two hours at 20°C during which the Procion blue dye reacted with some of the phenolic -OH groups of the novolak while the DNSC reacted with some of the other available phenolic -OH groups, to produce a resin functionalised with both dye and the photosensitising napthoquinone diazide.
  • the mildly alkali sodium hydrogen carbonate was present to counter the acid HCl produced during the reaction.
  • Product was recovered by precipitation into acidified water, followed by filtration, washing and drying.
  • the light sensitive product obtained was then used to produce a positive working lithographic plate.
  • the product was dissolved in 2-methoxy ethanol at a concentration of 20% w/w and then coated onto an aluminium sheet which had been freshly anodised with sulphuric acid. After drying the coated sheet was exposed with UV radiation. This caused a reaction in the light sensitive napthoquinone diazide functional groups of the exposed background areas which rendered them more soluble than the image areas.
  • subsequent development in aqueous alkaline solution selectively dissolved away the background to reveal a coloured image. There was no dye staining of the background (non-image areas) .
  • the Procion blue provides a permanent dye colour which does not change exposure.
  • a coatable composition was prepared from the following ingredients:
  • 2-methoxy ethanol 80% w/v
  • the composition was bar coated onto a freshly sulphuric acid anodised sheet of aluminium and imagewise exposed to active radiation.
  • the composition showed a distinct colour change from blue to yellow.
  • the plate was then developed in an aqueous alkaline solution which removed the yellow exposed non-image areas of the coating to reveal the anodic film which showed no staining.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Architecture (AREA)
  • Structural Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)
  • Phenolic Resins Or Amino Resins (AREA)
  • Materials For Photolithography (AREA)

Abstract

Procédé de préparation d'un matériau photosensible à action positive et contenant un colorant, consistant à faire réagir ensemble un phénol ou un phénol substitué, du formaldéhyde et un colorant pouvant se co-condenser avec le formaldéhyde et le phénol ou le phénol substitué, puis à faire réagir le produit avec un diazide de quinone. Le matériau peut être utilisé comme un revêtement pour une plaque d'impression lithographique, et peut être appliqué directement à des plaques qui ont été anodisées avec de l'acide sulfurique, sans que le colorant ne soit absorbé par la plaque.
PCT/GB1991/000858 1990-05-30 1991-05-30 Materiaux photosensibles pour plaques lithographiques WO1991019227A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9012021.3 1990-05-30
GB9012021A GB9012021D0 (en) 1990-05-30 1990-05-30 Light sensitive materials for lithographic plates

Publications (1)

Publication Number Publication Date
WO1991019227A1 true WO1991019227A1 (fr) 1991-12-12

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ID=10676754

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1991/000858 WO1991019227A1 (fr) 1990-05-30 1991-05-30 Materiaux photosensibles pour plaques lithographiques

Country Status (2)

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GB (1) GB9012021D0 (fr)
WO (1) WO1991019227A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999001795A2 (fr) * 1997-07-05 1999-01-14 Kodak Polychrome Graphics Company Ltd. Procedes de formation de motifs et des matieres sensibles aux rayonnements
WO2001094123A1 (fr) * 2000-06-07 2001-12-13 Kodak Polychrome Graphics Co. Ltd. Polymeres et leur utilisation dans des produits pouvant etre images, et procede de formation d'images
EP1297950A3 (fr) * 2001-09-27 2004-03-31 Agfa-Gevaert Précurseur de plaque d'impression lithographique sensible à la chaleur
EP1405141A1 (fr) * 2001-06-25 2004-04-07 Citiplate, Inc. Compositions de revetement thermosensibles contenant des novolaques diazo melangees, utiles dans des elements lithographiques
WO2004035687A1 (fr) * 2002-10-15 2004-04-29 Agfa-Gevaert Polymere destine a un precurseur de plaque d'impression lithographique thermosensible
US7041427B2 (en) 2001-09-27 2006-05-09 Agfa Gevaert Heat-sensitive lithographic printing plate precursor

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU289389A1 (ru) * Ю. С. Боков, Н. С. Малышева, В. Н. Егорова, В. П. Лаврищев, Н. В. Макаров, В. С. Корсаков , В. Г. Никольский Способ получения светочувствительных материалов
US3929488A (en) * 1971-06-17 1975-12-30 Howson Algraphy Ltd Light sensitive diazo composition with azo dye formed from a diazonium salt and a novolak resin
JPS646946A (en) * 1987-06-30 1989-01-11 Konishiroku Photo Ind Photosensitive composition and photosensitive plano-graphic printing plate

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU289389A1 (ru) * Ю. С. Боков, Н. С. Малышева, В. Н. Егорова, В. П. Лаврищев, Н. В. Макаров, В. С. Корсаков , В. Г. Никольский Способ получения светочувствительных материалов
US3929488A (en) * 1971-06-17 1975-12-30 Howson Algraphy Ltd Light sensitive diazo composition with azo dye formed from a diazonium salt and a novolak resin
JPS646946A (en) * 1987-06-30 1989-01-11 Konishiroku Photo Ind Photosensitive composition and photosensitive plano-graphic printing plate

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI, no. 71-70002s Derwent Publications Ltd, London, GB & SU-A-289389 (Bokov y. et al.) *
PATENT ABSTRACTS OF JAPAN vol. 13, no. 172 (P-862)(3520) 24 April 1989, & JP-A-01 006946 (KONIKA CORP) 11 January 1989, see the whole document *

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999001795A2 (fr) * 1997-07-05 1999-01-14 Kodak Polychrome Graphics Company Ltd. Procedes de formation de motifs et des matieres sensibles aux rayonnements
WO1999001795A3 (fr) * 1997-07-05 1999-04-15 Horsell Graphic Ind Ltd Procedes de formation de motifs et des matieres sensibles aux rayonnements
US6537735B1 (en) 1997-07-05 2003-03-25 Kodak Polychrome Graphics Llc Pattern-forming methods and radiation sensitive materials
WO2001094123A1 (fr) * 2000-06-07 2001-12-13 Kodak Polychrome Graphics Co. Ltd. Polymeres et leur utilisation dans des produits pouvant etre images, et procede de formation d'images
JP2003536095A (ja) * 2000-06-07 2003-12-02 コダック ポリクロム グラフィックス カンパニーリミテッド ポリマーならびにその画像形成可能な製品および画像形成方法における使用
US6667137B2 (en) 2000-06-07 2003-12-23 Kodak Polychrome Graphics Llc Polymers and their use in imageable products and image-forming methods
EP1405141A1 (fr) * 2001-06-25 2004-04-07 Citiplate, Inc. Compositions de revetement thermosensibles contenant des novolaques diazo melangees, utiles dans des elements lithographiques
EP1405141A4 (fr) * 2001-06-25 2006-09-20 Citiplate Inc Compositions de revetement thermosensibles contenant des novolaques diazo melangees, utiles dans des elements lithographiques
EP1297950A3 (fr) * 2001-09-27 2004-03-31 Agfa-Gevaert Précurseur de plaque d'impression lithographique sensible à la chaleur
US7041427B2 (en) 2001-09-27 2006-05-09 Agfa Gevaert Heat-sensitive lithographic printing plate precursor
WO2004035687A1 (fr) * 2002-10-15 2004-04-29 Agfa-Gevaert Polymere destine a un precurseur de plaque d'impression lithographique thermosensible
CN1320014C (zh) * 2002-10-15 2007-06-06 爱克发-格法特公司 用于热敏石印板前体的聚合物

Also Published As

Publication number Publication date
GB9012021D0 (en) 1990-07-18

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