GB1453681A - Photopolymerisable films having high resolution - Google Patents
Photopolymerisable films having high resolutionInfo
- Publication number
- GB1453681A GB1453681A GB246074A GB246074A GB1453681A GB 1453681 A GB1453681 A GB 1453681A GB 246074 A GB246074 A GB 246074A GB 246074 A GB246074 A GB 246074A GB 1453681 A GB1453681 A GB 1453681A
- Authority
- GB
- United Kingdom
- Prior art keywords
- nitroso
- methylene chloride
- dimer
- methyl
- compositions
- 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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 9
- 239000000203 mixture Substances 0.000 abstract 7
- 239000000178 monomer Substances 0.000 abstract 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 3
- OVOUKWFJRHALDD-UHFFFAOYSA-N 2-[2-(2-acetyloxyethoxy)ethoxy]ethyl acetate Chemical compound CC(=O)OCCOCCOCCOC(C)=O OVOUKWFJRHALDD-UHFFFAOYSA-N 0.000 abstract 2
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 abstract 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 abstract 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract 2
- 239000011230 binding agent Substances 0.000 abstract 2
- 239000000539 dimer Substances 0.000 abstract 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract 2
- 239000003112 inhibitor Substances 0.000 abstract 2
- 150000002832 nitroso derivatives Chemical class 0.000 abstract 2
- 125000000018 nitroso group Chemical group N(=O)* 0.000 abstract 2
- 239000004014 plasticizer Substances 0.000 abstract 2
- 239000000758 substrate Substances 0.000 abstract 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 abstract 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 abstract 1
- VOCDJQSAMZARGX-UHFFFAOYSA-N 1-ethenylpyrrolidine-2,5-dione Chemical compound C=CN1C(=O)CCC1=O VOCDJQSAMZARGX-UHFFFAOYSA-N 0.000 abstract 1
- LIVMKAMCUSERAR-UHFFFAOYSA-N 1-nitrosododecane Chemical compound CCCCCCCCCCCCN=O LIVMKAMCUSERAR-UHFFFAOYSA-N 0.000 abstract 1
- BTLOBJKRPAQWCD-UHFFFAOYSA-N 1-nitrosooctadecane Chemical compound CCCCCCCCCCCCCCCCCCN=O BTLOBJKRPAQWCD-UHFFFAOYSA-N 0.000 abstract 1
- HGVVUEKCGDPRHM-UHFFFAOYSA-N 2,3-dimethyl-2,3-dinitrosobutane Chemical compound O=NC(C)(C)C(C)(C)N=O HGVVUEKCGDPRHM-UHFFFAOYSA-N 0.000 abstract 1
- HWEBNHLROASIBS-UHFFFAOYSA-N 2,4-dimethyl-2-nitrosopentan-3-one Chemical compound CC(C)C(=O)C(C)(C)N=O HWEBNHLROASIBS-UHFFFAOYSA-N 0.000 abstract 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 abstract 1
- 229940093475 2-ethoxyethanol Drugs 0.000 abstract 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 abstract 1
- XCSGHNKDXGYELG-UHFFFAOYSA-N 2-phenoxyethoxybenzene Chemical compound C=1C=CC=CC=1OCCOC1=CC=CC=C1 XCSGHNKDXGYELG-UHFFFAOYSA-N 0.000 abstract 1
- KEIJOMQEKJEXFW-UHFFFAOYSA-N 3-methyl-3-nitrosocyclobutane-1-carbonitrile Chemical compound CC1(CC(C1)C#N)N=O KEIJOMQEKJEXFW-UHFFFAOYSA-N 0.000 abstract 1
- MDKBMQUAHQEWOH-UHFFFAOYSA-N 6-nitrosohexan-1-ol Chemical compound OCCCCCCN=O MDKBMQUAHQEWOH-UHFFFAOYSA-N 0.000 abstract 1
- YYVYAPXYZVYDHN-UHFFFAOYSA-N 9,10-phenanthroquinone Chemical compound C1=CC=C2C(=O)C(=O)C3=CC=CC=C3C2=C1 YYVYAPXYZVYDHN-UHFFFAOYSA-N 0.000 abstract 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- 239000004372 Polyvinyl alcohol Substances 0.000 abstract 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 abstract 1
- UJTHMGMWSSOKMD-UHFFFAOYSA-N [4-(prop-2-enoyloxymethyl)phenyl]methyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=C(COC(=O)C=C)C=C1 UJTHMGMWSSOKMD-UHFFFAOYSA-N 0.000 abstract 1
- 239000002318 adhesion promoter Substances 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- -1 amine compound Chemical class 0.000 abstract 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 abstract 1
- 239000012965 benzophenone Substances 0.000 abstract 1
- 229920006217 cellulose acetate butyrate Polymers 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 239000000945 filler Substances 0.000 abstract 1
- 150000002460 imidazoles Chemical class 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 229920003145 methacrylic acid copolymer Polymers 0.000 abstract 1
- 229940117841 methacrylic acid copolymer Drugs 0.000 abstract 1
- AFLQDEOAJRGCOW-UHFFFAOYSA-N nitrosocyclohexane Chemical compound O=NC1CCCCC1 AFLQDEOAJRGCOW-UHFFFAOYSA-N 0.000 abstract 1
- 150000002894 organic compounds Chemical class 0.000 abstract 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 abstract 1
- 229920006267 polyester film Polymers 0.000 abstract 1
- 239000004926 polymethyl methacrylate Substances 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
- 235000019260 propionic acid Nutrition 0.000 abstract 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 abstract 1
- 230000001235 sensitizing effect Effects 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 238000012719 thermal polymerization Methods 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polymerisation Methods In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Paints Or Removers (AREA)
Abstract
1453681 Photopolymerizable compositions E I DU PONT DE NEMOURS & CO 18 Jan 1974 [18 Jan 1973 (2) 12 Dec 1973] 02460/74 Heading C3P [Also in Division G2] Photopolymerizable compositions, suitable for making photographic elements by application to a substrate followed by exposure and development, comprise (i) at least one non- gaseous ethylenically unsaturated monomer, (ii) an organic light-sensitive free-radical generating system, and (iii) a dimer of a nitroso compound. The nitroso compound is a thermal polymerization inhibitor in monomeric form but not in dimeric form. The dimer dissociates with temperature increase to provide additional inhibitor, but at normal temperatures only a small amount of monomer is present. Suitable nitroso dimers are those of, for example, 1- nitrosododecane, 1 - nitrosooctadecane, nitrosocyclohexane, 2,3 - dimethyl - 2,3 - dinitrosobutane, 2 - nitroso - 2,4 - dimethyl - 3 - pentanone, 3 - methyl - 3 - nitrosocyclobutane carbonitrile and 6 - hydroxy - 1 - nitrosohexane, numerous others being also listed. Numerous monomers and sensitizing systems are listed, and the compositions may also contain polymeric binders, plasticizers, fillers, and liquid and crystalline organic compounds, all of which are exemplified. In examples, the following components are used in addition to the nitroso dimer: monomers: triethylene glycol diacrylate, trimethylolpropane triacrylate, 3-(3<SP>1</SP>-acryloxypropyl)propionic acid, 1,4 - benzenedimethanol diacrylate, p - α,α - dimethylbenzylphenyl acrylate and N-vinyl succinimide; sensitizers: phenanthraquinone, benzophenone, benzoin methyl ether, and mixtures of dimeric imidazole compounds with Michler's ketone and a benzoxazole or amine compound; binders: polymethyl methacrylate, cellulose acetate butyrate, methyl methacrylate/methacrylic acid copolymer, methyl methacrylate/acrylonitrile/butadiene/styrene copolymer and a polyurethane; solvents: methylene chloride, methylene chloride/1,2 - dichloroethane mixture, methylene chloride/2 - ethoxyethanol mixture and methyl ethyl ketone; other materials: 1,2 - diphenoxyethane, ethylene bis- (2 - oxyethyl acetate), triethylene glycol diacetate, a commercial plasticizer and a commercial adhesion promoter. The above compositions are applied to substrates, e.g. polyester film, grained aluminium strip or copper-clad circuit board, optionally the coatings are top-coated with polyvinyl alcohol solution, and the products exposed and developed by conventional methods.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32487773A | 1973-01-18 | 1973-01-18 | |
| US32488073A | 1973-01-18 | 1973-01-18 | |
| US42398973A | 1973-12-12 | 1973-12-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1453681A true GB1453681A (en) | 1976-10-27 |
Family
ID=27406364
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB246074A Expired GB1453681A (en) | 1973-01-18 | 1974-01-18 | Photopolymerisable films having high resolution |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS579056B2 (en) |
| DE (1) | DE2402179C2 (en) |
| FR (1) | FR2214703B1 (en) |
| GB (1) | GB1453681A (en) |
| NL (1) | NL173527C (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4268667A (en) | 1980-04-21 | 1981-05-19 | E. I. Du Pont De Nemours And Company | Derivatives of aryl ketones based on 9,10-dihydro-9,10-ethanoanthracene and p-dialkyl-aminoaryl aldehydes as visible sensitizers for photopolymerizable compositions |
| US7608388B2 (en) | 2004-10-12 | 2009-10-27 | Presstek, Inc. | Inkjet-imageable lithographic printing members and methods of preparing and imaging them |
| EP1621337B1 (en) * | 2004-06-18 | 2017-03-22 | FUJIFILM Corporation | Image recording material and lithographic printing plate precursor |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2542151C2 (en) * | 1975-01-20 | 1984-06-20 | E.I. Du Pont De Nemours And Co., Wilmington, Del. | Process for the production of positive images |
| IL60116A (en) * | 1979-06-25 | 1984-04-30 | University Patents Inc | Coating process and articles coated thereby |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1099166B (en) * | 1959-12-01 | 1961-02-09 | Basf Ag | Sensitizers for the photopolymerization of unsaturated organic compounds |
| DE1522444B2 (en) * | 1967-03-10 | 1977-07-07 | Basf Ag, 6700 Ludwigshafen | POLYMERIZATION INHIBITOR CONTAINING LIGHT-NETWORKABLE MIXTURE |
| GB1248569A (en) * | 1967-12-04 | 1971-10-06 | Agfa Gevaert | Photopolymerisation of ethylenically unsaturated organic compounds |
| DE1949010C3 (en) * | 1969-09-27 | 1979-11-29 | Bayer Ag, 5090 Leverkusen | Use of halogen methylated benzophenones as photopolymerization initiators |
-
1974
- 1974-01-17 DE DE19742402179 patent/DE2402179C2/en not_active Expired
- 1974-01-18 JP JP797574A patent/JPS579056B2/ja not_active Expired
- 1974-01-18 GB GB246074A patent/GB1453681A/en not_active Expired
- 1974-01-18 NL NL7400712A patent/NL173527C/en not_active IP Right Cessation
- 1974-01-18 FR FR7401778A patent/FR2214703B1/fr not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4268667A (en) | 1980-04-21 | 1981-05-19 | E. I. Du Pont De Nemours And Company | Derivatives of aryl ketones based on 9,10-dihydro-9,10-ethanoanthracene and p-dialkyl-aminoaryl aldehydes as visible sensitizers for photopolymerizable compositions |
| EP1621337B1 (en) * | 2004-06-18 | 2017-03-22 | FUJIFILM Corporation | Image recording material and lithographic printing plate precursor |
| US7608388B2 (en) | 2004-10-12 | 2009-10-27 | Presstek, Inc. | Inkjet-imageable lithographic printing members and methods of preparing and imaging them |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7400712A (en) | 1974-07-22 |
| DE2402179C2 (en) | 1983-03-31 |
| NL173527C (en) | 1984-02-01 |
| NL173527B (en) | 1983-09-01 |
| JPS49106319A (en) | 1974-10-08 |
| FR2214703A1 (en) | 1974-08-19 |
| FR2214703B1 (en) | 1977-09-23 |
| JPS579056B2 (en) | 1982-02-19 |
| DE2402179A1 (en) | 1974-07-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 19940117 |