GB1089095A - Cross-linkable light-sensitive polymeric materials - Google Patents

Cross-linkable light-sensitive polymeric materials

Info

Publication number
GB1089095A
GB1089095A GB2476064A GB2476064A GB1089095A GB 1089095 A GB1089095 A GB 1089095A GB 2476064 A GB2476064 A GB 2476064A GB 2476064 A GB2476064 A GB 2476064A GB 1089095 A GB1089095 A GB 1089095A
Authority
GB
United Kingdom
Prior art keywords
azidosulphonyl
chloride
products
reacted
isophthalyl
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
GB2476064A
Inventor
Urbain Leopold Laridon
Gerard Albert Delzenne
Helmut Mader
Hans Ulrich
Bernhard Seidel
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.)
Agfa Gevaert NV
Original Assignee
Agfa Gevaert NV
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 Agfa Gevaert NV filed Critical Agfa Gevaert NV
Priority to DE19651472765 priority Critical patent/DE1472765B2/en
Priority to SE7795/65A priority patent/SE344247B/xx
Priority to CH825165A priority patent/CH474089A/en
Priority to FR20910A priority patent/FR1455154A/en
Priority to NL6507630A priority patent/NL149608B/en
Priority to BE665428D priority patent/BE665428A/nl
Publication of GB1089095A publication Critical patent/GB1089095A/en
Priority to US05/558,622 priority patent/US4065524A/en
Expired legal-status Critical Current

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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
    • C08B15/05—Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur
    • C08B15/06—Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur containing nitrogen, e.g. carbamates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/34—Introducing sulfur atoms or sulfur-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/71—Monoisocyanates or monoisothiocyanates
    • C08G18/715—Monoisocyanates or monoisothiocyanates containing sulfur in addition to isothiocyanate sulfur
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/14—Polycondensates modified by chemical after-treatment
    • C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
    • C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
    • C08G59/1455—Monocarboxylic acids, anhydrides, halides, or low-molecular-weight esters thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
    • C08G59/4064—Curing agents not provided for by the groups C08G59/42 - C08G59/66 sulfur containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
    • C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
    • C08G63/6854—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen derived from polycarboxylic acids and polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
    • C08G63/688—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur
    • C08G63/6884—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur derived from polycarboxylic acids and polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G85/00—General processes for preparing compounds provided for in this subclass
    • C08G85/004—Modification of polymers by chemical after-treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such 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
    • G03F7/008—Azides
    • 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
    • G03F7/008—Azides
    • G03F7/012—Macromolecular azides; Macromolecular additives, e.g. binders

Abstract

Light-sensitive polymeric materials comprise cross-linkable polymers containing azidosulphonyl groups attached to carbon atoms therein and groups, e.g. hydroxyl, pyridine, phenyl, lactam and ethylenically unsaturated groups, reactive with the photo-chemical decomposition products of the azidosulphonyl groups, either in the azidosulphonyl containing polymer or in a further polymer admixed therewith. The polymers may be modified natural or synthetic polymers, e.g. reaction products of sodium azide with chlorosulphonated styrene polymers and copolymers, reaction products of azidosulphonyl benzoyl chlorides with polyvinyl alcohol, vinyl alcohol/vinyl butyral copolymers and bisphenol A/epichlorohydrin condensates, and polycondensation products such as polyamides, polyureas, polyurethanes, polyesters, polysulphonamides and polysulphonates containing azidosulphonyl substituents. Cross-linking may be enhanced by the presence of sensitizing compounds or substituent sensitizing groups in the polymer. The condensation products may be prepared by interfacial condensation between an aqueous phase containing diamine or diol and alkali and an organic solvent phase, e.g. of chlorinated aliphatic hydrocarbons, hexane or aromatic hydrocarbons, containing diacid halides, diisocyanates, dihalocarbonylamino or dihalocarbonyloxy compounds. The products may be cast into films or coated on metals, paper, glass or plastics, and selectively exposed to form resists. In examples bisphenol A/epichlorohydrin condensates are reacted with (1-11 and 14-32) m-azidosulphonyl benzoyl chloride and (13) p-azido sulphonyl benzoyl chloride, sensitized with various sensitizers, and reacted with (42) l - p - chlorocarbonylphenyl - 3 - phenyl - 2-pyrazoline and m-azidosulphonyl benzoyl chloride; (12) a vinyl butyral/vinyl alcohol copolymer is reacted with m-azidosulphonyl benzoyl chloride; (33) p-chlorosulphonated polystyrene is reacted with sodium azide, and (34) admixed with poly-N-vinyl pyrrolidone; (35) polychloromethyl styrene is reacted with 2-chloro-5-azidosulphonyl benzoic acid, and admixed with (36) poly-N-vinyl pyrrolidone and (37) polystyrene; and interfacial polycondensation products are prepared from bisphenol A and (38) isophthalyl chloride and 5-azidosulphonyl isophthalyl chloride, (39) isophthalyl chloride, 5-azidosulphonyl isophthalyl chloride and pyridine-2,6-dicarboxylic acid chloride, (40) 5-azidosulphonyl isophthalyl chloride and (41) terephthalyl chloride, isophthalyl chloride and 5-azidosulphonyl isophthalyl chloride.ALSO:Azidosulphonyl benzoic acids may be prepared by reacting the chlorosulphonyl benzoic acids with sodium azide. The products may be converted to the corresponding acid chlorides by refluxing with thionyl chloride. In examples the (1) m- and (13) p-azidosulphonyl benzoic acids and benzoyl chlorides are prepared. In Example (35) 2-chloro-5-azido-sulphonyl benzoic acid is prepared by reacting 2-chloro-5-chlorosulphonyl benzoic acid with sodium azide.
GB2476064A 1964-06-15 1964-06-15 Cross-linkable light-sensitive polymeric materials Expired GB1089095A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
DE19651472765 DE1472765B2 (en) 1964-06-15 1965-06-12 LIGHT-NETWORKABLE LAYER
SE7795/65A SE344247B (en) 1964-06-15 1965-06-14
CH825165A CH474089A (en) 1964-06-15 1965-06-14 Photosensitive material
FR20910A FR1455154A (en) 1964-06-15 1965-06-15 Photochemical crosslinking of polymers
NL6507630A NL149608B (en) 1964-06-15 1965-06-15 PHOTOGRAPHIC REGISTRATION MATERIAL AND METHOD FOR PREPARING A LIGHT-SENSITIVE POLYMER TO BE USED THEREIN.
BE665428D BE665428A (en) 1964-06-15 1965-06-15
US05/558,622 US4065524A (en) 1964-06-15 1975-03-17 Film-forming light-sensitive polymeric material carrying azidosulfonyl groups

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB1581165 1965-04-13
GB1581065 1965-04-13

Publications (1)

Publication Number Publication Date
GB1089095A true GB1089095A (en) 1967-11-01

Family

ID=26251555

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2476064A Expired GB1089095A (en) 1964-06-15 1964-06-15 Cross-linkable light-sensitive polymeric materials

Country Status (1)

Country Link
GB (1) GB1089095A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3617271A (en) * 1968-06-10 1971-11-02 Agfa Gevaert Nv Sensitizers having one or more electron-withdrawing groups for organic photoconductors
US3652285A (en) * 1968-07-01 1972-03-28 Agfa Gevaert Nv Photochromic-photopolymerization compositions
CN116396733A (en) * 2023-04-13 2023-07-07 中国石油天然气股份有限公司长庆油田分公司第十二采油厂 Plugging agent and construction method thereof

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3617271A (en) * 1968-06-10 1971-11-02 Agfa Gevaert Nv Sensitizers having one or more electron-withdrawing groups for organic photoconductors
US3652285A (en) * 1968-07-01 1972-03-28 Agfa Gevaert Nv Photochromic-photopolymerization compositions
CN116396733A (en) * 2023-04-13 2023-07-07 中国石油天然气股份有限公司长庆油田分公司第十二采油厂 Plugging agent and construction method thereof
CN116396733B (en) * 2023-04-13 2024-04-05 中国石油天然气股份有限公司长庆油田分公司第十二采油厂 Plugging agent and construction method thereof

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