CA1078659A - Cyclopropenone vesicular imaging composition, element and process - Google Patents
Cyclopropenone vesicular imaging composition, element and processInfo
- Publication number
- CA1078659A CA1078659A CA270,840A CA270840A CA1078659A CA 1078659 A CA1078659 A CA 1078659A CA 270840 A CA270840 A CA 270840A CA 1078659 A CA1078659 A CA 1078659A
- Authority
- CA
- Canada
- Prior art keywords
- carbon atoms
- cyclopropenone
- composition
- binder
- polymer
- 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
- GGRQLKPIJPFWEZ-UHFFFAOYSA-N cycloprop-2-en-1-one Chemical compound O=C1C=C1 GGRQLKPIJPFWEZ-UHFFFAOYSA-N 0.000 title claims abstract description 66
- 239000000203 mixture Substances 0.000 title claims abstract description 31
- 238000003384 imaging method Methods 0.000 title claims abstract description 22
- 238000000034 method Methods 0.000 title claims abstract description 16
- 230000008569 process Effects 0.000 title claims abstract description 11
- 239000011230 binding agent Substances 0.000 claims abstract description 45
- 230000003595 spectral effect Effects 0.000 claims abstract description 44
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 42
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 230000001235 sensitizing effect Effects 0.000 claims abstract description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
- 229920000642 polymer Polymers 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 230000035945 sensitivity Effects 0.000 claims description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 150000003254 radicals Chemical class 0.000 claims description 9
- 150000005840 aryl radicals Chemical class 0.000 claims description 7
- 230000005855 radiation Effects 0.000 claims description 7
- 230000004044 response Effects 0.000 claims description 6
- HCIBTBXNLVOFER-UHFFFAOYSA-N diphenylcyclopropenone Chemical group O=C1C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 HCIBTBXNLVOFER-UHFFFAOYSA-N 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 230000001419 dependent effect Effects 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 230000003213 activating effect Effects 0.000 claims description 3
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 claims description 3
- QWIIPRYMQRDLQI-UHFFFAOYSA-N 2-(4-methoxyphenyl)-3-phenylcycloprop-2-en-1-one Chemical group C1=CC(OC)=CC=C1C(C1=O)=C1C1=CC=CC=C1 QWIIPRYMQRDLQI-UHFFFAOYSA-N 0.000 claims description 2
- 238000006303 photolysis reaction Methods 0.000 claims description 2
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 claims description 2
- 229940124530 sulfonamide Drugs 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 125000004104 aryloxy group Chemical group 0.000 claims 3
- 231100000202 sensitizing Toxicity 0.000 claims 3
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims 1
- 229920001169 thermoplastic Polymers 0.000 claims 1
- 239000004416 thermosoftening plastic Substances 0.000 claims 1
- -1 silver halide Chemical class 0.000 description 30
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- 238000000576 coating method Methods 0.000 description 20
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- 231100000489 sensitizer Toxicity 0.000 description 18
- 239000007789 gas Substances 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 10
- 229920000139 polyethylene terephthalate Polymers 0.000 description 9
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- 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 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
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- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
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- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 5
- 230000035699 permeability Effects 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 4
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- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000013557 residual solvent Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- BLZOHTXDDOAASQ-UHFFFAOYSA-N 1,2,3,3-tetrachlorocyclopropene Chemical compound ClC1=C(Cl)C1(Cl)Cl BLZOHTXDDOAASQ-UHFFFAOYSA-N 0.000 description 2
- KTGDICHJNYXCPS-UHFFFAOYSA-N 2-(2-methoxynaphthalen-1-yl)-3-phenylcycloprop-2-en-1-one Chemical compound COC1=CC=C2C=CC=CC2=C1C(C1=O)=C1C1=CC=CC=C1 KTGDICHJNYXCPS-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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- 229920001519 homopolymer Polymers 0.000 description 2
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- 229920001897 terpolymer Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- SGMODQNVAQABMZ-UHFFFAOYSA-N 1,3-bis(furan-2-yl)-2-(1-methylbenzo[e][1,3]benzothiazol-2-ylidene)propane-1,3-dione Chemical compound S1C2=CC=C3C=CC=CC3=C2N(C)C1=C(C(=O)C=1OC=CC=1)C(=O)C1=CC=CO1 SGMODQNVAQABMZ-UHFFFAOYSA-N 0.000 description 1
- ALRLPDGCPYIVHP-UHFFFAOYSA-N 1-nitropyrene Chemical class C1=C2C([N+](=O)[O-])=CC=C(C=C3)C2=C2C3=CC=CC2=C1 ALRLPDGCPYIVHP-UHFFFAOYSA-N 0.000 description 1
- MQXNNWDXHFBFEB-UHFFFAOYSA-N 2,2-bis(2-hydroxyphenyl)propane Chemical compound C=1C=CC=C(O)C=1C(C)(C)C1=CC=CC=C1O MQXNNWDXHFBFEB-UHFFFAOYSA-N 0.000 description 1
- ILMMSAVBFQSGBD-UHFFFAOYSA-N 2,3-bis(2,2-diphenylethenyl)cycloprop-2-en-1-one Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=1C(=O)C=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 ILMMSAVBFQSGBD-UHFFFAOYSA-N 0.000 description 1
- BKLVSSYBPNMGQX-UHFFFAOYSA-N 2,3-bis(2,4-dimethoxyphenyl)cycloprop-2-en-1-one Chemical compound COC1=CC(OC)=CC=C1C(C1=O)=C1C1=CC=C(OC)C=C1OC BKLVSSYBPNMGQX-UHFFFAOYSA-N 0.000 description 1
- ZCGQKIMKRDUVQF-UHFFFAOYSA-N 2,3-bis(2,5-dimethylphenyl)cycloprop-2-en-1-one Chemical compound CC1=CC=C(C)C(C=2C(C=2C=2C(=CC=C(C)C=2)C)=O)=C1 ZCGQKIMKRDUVQF-UHFFFAOYSA-N 0.000 description 1
- OCUMPRIKLTWIJG-UHFFFAOYSA-N 2,3-bis(3-nitrophenyl)cycloprop-2-en-1-one Chemical compound [O-][N+](=O)C1=CC=CC(C=2C(C=2C=2C=C(C=CC=2)[N+]([O-])=O)=O)=C1 OCUMPRIKLTWIJG-UHFFFAOYSA-N 0.000 description 1
- NPOLTJNFAQNEAA-UHFFFAOYSA-N 2,3-bis(4-methoxyphenyl)cycloprop-2-en-1-one Chemical compound C1=CC(OC)=CC=C1C(C1=O)=C1C1=CC=C(OC)C=C1 NPOLTJNFAQNEAA-UHFFFAOYSA-N 0.000 description 1
- XYDCYWOOZUVWCD-UHFFFAOYSA-N 2,3-bis(4-phenoxyphenyl)cycloprop-2-en-1-one Chemical compound O=C1C(C=2C=CC(OC=3C=CC=CC=3)=CC=2)=C1C(C=C1)=CC=C1OC1=CC=CC=C1 XYDCYWOOZUVWCD-UHFFFAOYSA-N 0.000 description 1
- PTOFMDJCTXBGLQ-UHFFFAOYSA-N 2-(2,5-dimethoxyphenyl)-3-phenylcycloprop-2-en-1-one Chemical compound COC1=CC=C(OC)C(C=2C(C=2C=2C=CC=CC=2)=O)=C1 PTOFMDJCTXBGLQ-UHFFFAOYSA-N 0.000 description 1
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- FTQSQHVSNRXMTR-UHFFFAOYSA-N 2-[(6-methoxy-1-phenylcyclohexa-2,4-dien-1-yl)methyl]cycloprop-2-en-1-one Chemical compound COC1C=CC=CC1(C=1C=CC=CC=1)CC1=CC1=O FTQSQHVSNRXMTR-UHFFFAOYSA-N 0.000 description 1
- WNBQNPLPWYPVCU-UHFFFAOYSA-N 4-methylbenzene-1,3-disulfonamide Chemical group CC1=CC=C(S(N)(=O)=O)C=C1S(N)(=O)=O WNBQNPLPWYPVCU-UHFFFAOYSA-N 0.000 description 1
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- 238000001429 visible spectrum Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
- G03C5/60—Processes for obtaining vesicular images
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/72—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705
- G03C1/73—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705 containing organic compounds
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/739,774 US4128422A (en) | 1976-11-08 | 1976-11-08 | Cyclopropenone vesicular imaging composition, element and process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1078659A true CA1078659A (en) | 1980-06-03 |
Family
ID=24973734
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA270,840A Expired CA1078659A (en) | 1976-11-08 | 1977-02-01 | Cyclopropenone vesicular imaging composition, element and process |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4128422A (enExample) |
| CA (1) | CA1078659A (enExample) |
| FR (1) | FR2370304A1 (enExample) |
| GB (1) | GB1593522A (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2965081D1 (en) * | 1978-12-11 | 1983-04-28 | Bexford Ltd | Vesicular recording materials and process for their production |
| US4368247A (en) * | 1981-06-29 | 1983-01-11 | Eastman Kodak Company | Photographic materials and processes comprising oxoindolizine and oxoindolizinium compounds |
| US4450093A (en) * | 1981-06-29 | 1984-05-22 | Eastman Kodak Company | Indolizinone dyes and compositions, elements and methods using same |
| US4373021A (en) * | 1981-06-29 | 1983-02-08 | Eastman Kodak Company | Indolizinone dyes and compositions, elements and methods using same |
| US4577024A (en) * | 1981-06-29 | 1986-03-18 | Eastman Kodak Company | Oxoindolizine and oxoindolizinium compounds useful as dyes |
| US6794107B2 (en) | 2002-10-28 | 2004-09-21 | Kodak Polychrome Graphics Llc | Thermal generation of a mask for flexography |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1952787A (en) * | 1930-06-09 | 1934-03-27 | Photo Cast Inc | Method of printing |
| US3091532A (en) * | 1960-12-30 | 1963-05-28 | Ibm | Vesicular image photography process with polyketone photographic films |
| US3355295A (en) * | 1964-02-11 | 1967-11-28 | Eastman Kodak Co | Nucleated vesicular film |
| US3657348A (en) * | 1968-05-03 | 1972-04-18 | Dow Chemical Co | Disubstituted cyclopropenones and method of production |
| DE2121014A1 (de) * | 1971-04-29 | 1972-11-02 | Agfa-Gevaert Ag, 5090 Leverkusen | Sensibilisierte elektrophotographische Schichten |
-
1976
- 1976-11-08 US US05/739,774 patent/US4128422A/en not_active Expired - Lifetime
-
1977
- 1977-02-01 CA CA270,840A patent/CA1078659A/en not_active Expired
- 1977-11-07 GB GB46260/77A patent/GB1593522A/en not_active Expired
- 1977-11-08 FR FR7733517A patent/FR2370304A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2370304A1 (fr) | 1978-06-02 |
| FR2370304B1 (enExample) | 1981-01-02 |
| GB1593522A (en) | 1981-07-15 |
| US4128422A (en) | 1978-12-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |