GB1089095A - Cross-linkable light-sensitive polymeric materials - Google Patents
Cross-linkable light-sensitive polymeric materialsInfo
- 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
Links
- 239000000463 material Substances 0.000 title abstract 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 abstract 8
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 abstract 7
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 abstract 6
- 229920000642 polymer Polymers 0.000 abstract 6
- 239000000047 product Substances 0.000 abstract 5
- -1 azidosulphonyl groups Chemical group 0.000 abstract 4
- VIMBXOWNDHBZNG-UHFFFAOYSA-N 3-azidosulfonylbenzoyl chloride Chemical compound ClC(=O)C1=CC=CC(S(=O)(=O)N=[N+]=[N-])=C1 VIMBXOWNDHBZNG-UHFFFAOYSA-N 0.000 abstract 3
- 229920001577 copolymer Polymers 0.000 abstract 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract 3
- OIPUSVMMOSOYAU-UHFFFAOYSA-N 5-azidosulfonyl-2-chlorobenzoic acid Chemical compound OC(=O)C1=CC(S(=O)(=O)N=[N+]=[N-])=CC=C1Cl OIPUSVMMOSOYAU-UHFFFAOYSA-N 0.000 abstract 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 2
- 239000004793 Polystyrene Substances 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- 239000007795 chemical reaction product Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- JTHNLKXLWOXOQK-UHFFFAOYSA-N n-propyl vinyl ketone Natural products CCCC(=O)C=C JTHNLKXLWOXOQK-UHFFFAOYSA-N 0.000 abstract 2
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 abstract 2
- 229920002223 polystyrene Polymers 0.000 abstract 2
- 230000001235 sensitizing effect Effects 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- UXWZZMXHLVNJDQ-UHFFFAOYSA-N 2-azidosulfonylbenzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1S(=O)(=O)N=[N+]=[N-] UXWZZMXHLVNJDQ-UHFFFAOYSA-N 0.000 abstract 1
- CLHNTBSDCJLCKV-UHFFFAOYSA-N 2-chloro-5-chlorosulfonylbenzoic acid Chemical compound OC(=O)C1=CC(S(Cl)(=O)=O)=CC=C1Cl CLHNTBSDCJLCKV-UHFFFAOYSA-N 0.000 abstract 1
- ZRWICZHXYMHBDP-UHFFFAOYSA-N 2-chlorosulfonylbenzoic acid Chemical class OC(=O)C1=CC=CC=C1S(Cl)(=O)=O ZRWICZHXYMHBDP-UHFFFAOYSA-N 0.000 abstract 1
- CBECDWUDYQOTSW-UHFFFAOYSA-N 2-ethylbut-3-enal Chemical compound CCC(C=C)C=O CBECDWUDYQOTSW-UHFFFAOYSA-N 0.000 abstract 1
- OWULJVXJAZBQLL-UHFFFAOYSA-N 4-azidosulfonylbenzoic acid Chemical class OC(=O)C1=CC=C(S(=O)(=O)N=[N+]=[N-])C=C1 OWULJVXJAZBQLL-UHFFFAOYSA-N 0.000 abstract 1
- MZCCLQIPLSOSDF-UHFFFAOYSA-N 4-azidosulfonylbenzoyl chloride Chemical compound ClC(=O)C1=CC=C(S(=O)(=O)N=[N+]=[N-])C=C1 MZCCLQIPLSOSDF-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 abstract 1
- 238000012696 Interfacial polycondensation Methods 0.000 abstract 1
- 239000004952 Polyamide Substances 0.000 abstract 1
- 229920002396 Polyurea Polymers 0.000 abstract 1
- 239000004372 Polyvinyl alcohol Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 239000008346 aqueous phase Substances 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- 235000010233 benzoic acid Nutrition 0.000 abstract 1
- 150000001559 benzoic acids Chemical class 0.000 abstract 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000002144 chemical decomposition reaction Methods 0.000 abstract 1
- 150000001805 chlorine compounds Chemical class 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 239000007859 condensation product Substances 0.000 abstract 1
- 238000004132 cross linking Methods 0.000 abstract 1
- 150000004985 diamines Chemical class 0.000 abstract 1
- 125000005442 diisocyanate group Chemical group 0.000 abstract 1
- 150000002009 diols Chemical class 0.000 abstract 1
- 239000011521 glass Substances 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 150000003951 lactams Chemical class 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- 229920005615 natural polymer Polymers 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000000123 paper Substances 0.000 abstract 1
- 239000012071 phase Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 229920003023 plastic Polymers 0.000 abstract 1
- 239000004033 plastic Substances 0.000 abstract 1
- 229920002647 polyamide Polymers 0.000 abstract 1
- 238000006068 polycondensation reaction Methods 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- 229920002635 polyurethane Polymers 0.000 abstract 1
- 239000004814 polyurethane Substances 0.000 abstract 1
- 229920002451 polyvinyl alcohol Polymers 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- GWHOGODUVLQCEB-UHFFFAOYSA-N pyridine-2,6-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=N1 GWHOGODUVLQCEB-UHFFFAOYSA-N 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 150000003440 styrenes Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 229920001059 synthetic polymer Polymers 0.000 abstract 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Chemical & Material Sciences (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Emergency Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
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.
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19651472765 DE1472765B2 (en) | 1964-06-15 | 1965-06-12 | LIGHT-NETWORKABLE LAYER |
| CH825165A CH474089A (en) | 1964-06-15 | 1965-06-14 | Photosensitive material |
| SE7795/65A SE344247B (en) | 1964-06-15 | 1965-06-14 | |
| BE665428D BE665428A (en) | 1964-06-15 | 1965-06-15 | |
| 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. |
| 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)
| 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 |
-
1964
- 1964-06-15 GB GB2476064A patent/GB1089095A/en not_active Expired
Cited By (4)
| 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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