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GB1463816A - Photosensitive lithographic materials and polymers useful therein - Google Patents

Photosensitive lithographic materials and polymers useful therein

Info

Publication number
GB1463816A
GB1463816A GB5194173A GB5194173A GB1463816A GB 1463816 A GB1463816 A GB 1463816A GB 5194173 A GB5194173 A GB 5194173A GB 5194173 A GB5194173 A GB 5194173A GB 1463816 A GB1463816 A GB 1463816A
Authority
GB
United Kingdom
Prior art keywords
methylmethacrylate
hydroxyethylmethacrylate
polymers
acryloyl
hydroxypropylmethacrylamide
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.)
Expired
Application number
GB5194173A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kodak Ltd
Original Assignee
Kodak Ltd
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 Kodak Ltd filed Critical Kodak Ltd
Priority to GB5194173A priority Critical patent/GB1463816A/en
Priority to CA212,535A priority patent/CA1041698A/en
Priority to FR7436756A priority patent/FR2251031B1/fr
Priority to IT2917474A priority patent/IT1025479B/en
Priority to BE150315A priority patent/BE821970A/en
Priority to NL7414518A priority patent/NL7414518A/en
Priority to DE19742452761 priority patent/DE2452761A1/en
Priority to JP12885074A priority patent/JPS5078402A/ja
Priority to AU75175/74A priority patent/AU488264B2/en
Publication of GB1463816A publication Critical patent/GB1463816A/en
Expired legal-status Critical Current

Links

Classifications

    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/038Macromolecular compounds which are rendered insoluble or differentially wettable
    • G03F7/0388Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/027Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/027Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/033Non-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
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/038Macromolecular compounds which are rendered insoluble or differentially wettable

Landscapes

  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

1463816 Ethylenically unsaturated polymers comprising halogen atoms KODAK Ltd 7 Nov 1974 [8 Nov 1973] 51941/73 Heading C3P [Also in Divisions C2 and G2] A polymer comprises repeating units containing a group having two or three halogen atoms attached to the same carbon atom and repeating units containing an olefinically unsaturated group. The preferred halogens are chlorine and bromine, and the preferred repeating units are trichloroacetyl or tribromoacetyl and acryloyl or methacryloyl groups. Preferred polymers are represented by the formula wherein R<SP>0</SP>, R<SP>2</SP>, R<SP>4</SP>, R<SP>6</SP>, R<SP>8</SP> is H or CH 3 ; R<SP>1</SP> is alkyl of 1-4 carbon atoms; R<SP>3</SP> is CO.OH or CO.NH.R a wherein R a is H or optionally substituted alkyl of 1-4 carbon atoms; R<SP>5</SP> is CN, CO.O-R b -OH or CO.NH-R b -OH wherein R b is an alkylene group of 1 to 4 carbon atoms; R<SP>7</SP> is wherein R b is as above and R c is H or CH 3 ; R<SP>9</SP> is O-R b -O.OC.CX 3 or NH-R b -O.CO.CX 3 wherein Rb is as above and X is Cl or Br and wherein the value of Z is such that the polystyrene equivalent molecular weight of the polymer, as measured by gel permeation chromatography, is 10<SP>4</SP>-10<SP>6</SP> and the values represented by n<SP>1</SP>, m, o, p and q are expressed by n<SP>1</SP> is 5-10, m is 0À5-3, o is 0-1, p is 0À5-3 and q is 0À25-2. The polymers are preferably obtained by reacting a polymer derived from a C 1-4 alkyl(meth)acrylate and a C 1-4 hydroxyalkyl(meth)acrylate with a mixture of (1) a carboxylic acid or carboxylic acid halide having a carbon atom to which two or three chlorine or bromine atoms are attached and (2) an olefinically unsaturated carboxylic acid halide. In the Preparations, the starting polymers prepared are copolymers of methylmethacrylate- /2 - hydroxyethylmethacrylate; methylmethacrylate / butylmethacrylate / 2 - hydroxyethylmethacrylate; methylmethacrylate / ethyl - N- acryloyl glycine/2-hydroxyethylmethacrylate; acrylic acid / methylmethacrylate / 2- hydroxyethylmethacrylate; methylmethacrylate / N - 2- hydroxypropylmethacrylamide; methylmethacrylate / N - isopropylacrylamide / 2 - hydroxyethylmethacrylate; methylmethacrylate/metliacrylamide / 2 - hydroxyethylmethacrylate; methylmethacrylate/n - butylmethacrylate/N- 2 - hydroxypropylmethacrylamide; acrylonitrile/methylmethacrylate/N - 2 - hydroxypropylmethacrylamide which are reacted with trichloroacetyl chloride and acryloyl chloride; tribromoacetyl bromide and acryloyl chloride; tribromoacetyl bromide and methacryloyl chloride. The polymers may be mixed with a metal carbonyl or derivative thereof for use as a photosensitive material (see Division G2).
GB5194173A 1973-11-08 1973-11-08 Photosensitive lithographic materials and polymers useful therein Expired GB1463816A (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
GB5194173A GB1463816A (en) 1973-11-08 1973-11-08 Photosensitive lithographic materials and polymers useful therein
CA212,535A CA1041698A (en) 1973-11-08 1974-10-29 Photosensitive materials
FR7436756A FR2251031B1 (en) 1973-11-08 1974-11-06
IT2917474A IT1025479B (en) 1973-11-08 1974-11-06 PHOTOSENSITIVE MATERIALS
BE150315A BE821970A (en) 1973-11-08 1974-11-07 NON-ARGENTIC PHOTOSENSITIVE PRODUCT CONTAINING NEW POLYMERS AND PROCESS FOR FORMING A LITHOGRAPHIC PRINTING BOARD BY MEANS OF THIS PRODUCT
NL7414518A NL7414518A (en) 1973-11-08 1974-11-07 METHOD FOR PREPARING PHOTOSENSITIVE MATERIALS.
DE19742452761 DE2452761A1 (en) 1973-11-08 1974-11-07 PHOTOGRAPHIC RECORDING MATERIAL
JP12885074A JPS5078402A (en) 1973-11-08 1974-11-08
AU75175/74A AU488264B2 (en) 1973-11-08 1974-11-08 Photo crosslinkable materials and compositions

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB5194173A GB1463816A (en) 1973-11-08 1973-11-08 Photosensitive lithographic materials and polymers useful therein

Publications (1)

Publication Number Publication Date
GB1463816A true GB1463816A (en) 1977-02-09

Family

ID=10462052

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5194173A Expired GB1463816A (en) 1973-11-08 1973-11-08 Photosensitive lithographic materials and polymers useful therein

Country Status (8)

Country Link
JP (1) JPS5078402A (en)
BE (1) BE821970A (en)
CA (1) CA1041698A (en)
DE (1) DE2452761A1 (en)
FR (1) FR2251031B1 (en)
GB (1) GB1463816A (en)
IT (1) IT1025479B (en)
NL (1) NL7414518A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4097281A (en) * 1977-10-17 1978-06-27 Eastman Kodak Company Heat developable photographic material and process comprising transition metal carbonyl compounds
FR2427635A1 (en) * 1978-05-31 1979-12-28 Eastman Kodak Co COMPOSITION OF PHOTOSENSITIVE POLYMER AND ITS APPLICATION IN LITHOGRAPHY
US4503140A (en) * 1982-05-18 1985-03-05 Minnesota Mining And Manufacturing Company Radiation-sensitive compositions of polymers containing a π-metal carbonyl complex of conjugated polyolefin
GB2287707A (en) * 1994-03-25 1995-09-27 Erba Carlo Spa Production of N-(2-hydroxypropyl) methacrylamide
US6132860A (en) * 1992-05-21 2000-10-17 3M Innovative Properties Company Abrasive article comprising organometallic coupling agent
US6217984B1 (en) 1992-05-21 2001-04-17 3M Innovative Properties Company Organometallic monomers and polymers with improved adhesion

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0767868B2 (en) * 1984-10-23 1995-07-26 三菱化学株式会社 Photosensitive lithographic printing plate
JPS62290705A (en) * 1986-06-10 1987-12-17 Mitsubishi Chem Ind Ltd Photopolymerizable composition

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4097281A (en) * 1977-10-17 1978-06-27 Eastman Kodak Company Heat developable photographic material and process comprising transition metal carbonyl compounds
FR2427635A1 (en) * 1978-05-31 1979-12-28 Eastman Kodak Co COMPOSITION OF PHOTOSENSITIVE POLYMER AND ITS APPLICATION IN LITHOGRAPHY
US4229519A (en) 1978-05-31 1980-10-21 Eastman Kodak Company Photo-polymerizable water-developable composition and elements
US4503140A (en) * 1982-05-18 1985-03-05 Minnesota Mining And Manufacturing Company Radiation-sensitive compositions of polymers containing a π-metal carbonyl complex of conjugated polyolefin
US6132860A (en) * 1992-05-21 2000-10-17 3M Innovative Properties Company Abrasive article comprising organometallic coupling agent
US6217984B1 (en) 1992-05-21 2001-04-17 3M Innovative Properties Company Organometallic monomers and polymers with improved adhesion
GB2287707A (en) * 1994-03-25 1995-09-27 Erba Carlo Spa Production of N-(2-hydroxypropyl) methacrylamide
GB2287707B (en) * 1994-03-25 1998-02-25 Erba Carlo Spa Intermediates for biologically active products

Also Published As

Publication number Publication date
IT1025479B (en) 1978-08-10
JPS5078402A (en) 1975-06-26
FR2251031B1 (en) 1976-10-22
NL7414518A (en) 1975-05-12
DE2452761A1 (en) 1975-05-15
FR2251031A1 (en) 1975-06-06
CA1041698A (en) 1978-10-31
AU7517574A (en) 1976-05-13
BE821970A (en) 1975-05-07

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee