GB1463816A - Photosensitive lithographic materials and polymers useful therein - Google Patents
Photosensitive lithographic materials and polymers useful thereinInfo
- 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
Links
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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
-
- 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
-
- 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
- G03F7/038—Macromolecular 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).
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)
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)
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 |
-
1973
- 1973-11-08 GB GB5194173A patent/GB1463816A/en not_active Expired
-
1974
- 1974-10-29 CA CA212,535A patent/CA1041698A/en not_active Expired
- 1974-11-06 IT IT2917474A patent/IT1025479B/en active
- 1974-11-06 FR FR7436756A patent/FR2251031B1/fr not_active Expired
- 1974-11-07 DE DE19742452761 patent/DE2452761A1/en active Pending
- 1974-11-07 NL NL7414518A patent/NL7414518A/en not_active Application Discontinuation
- 1974-11-07 BE BE150315A patent/BE821970A/en unknown
- 1974-11-08 JP JP12885074A patent/JPS5078402A/ja active Pending
Cited By (8)
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 |