CH651023A5 - Alpha-diazoacetylderivate von aromatischen stickstoffhaltigen heterocyclen und ein daraus gebildetes lichtempfindliches material. - Google Patents
Alpha-diazoacetylderivate von aromatischen stickstoffhaltigen heterocyclen und ein daraus gebildetes lichtempfindliches material. Download PDFInfo
- Publication number
- CH651023A5 CH651023A5 CH501882A CH501882A CH651023A5 CH 651023 A5 CH651023 A5 CH 651023A5 CH 501882 A CH501882 A CH 501882A CH 501882 A CH501882 A CH 501882A CH 651023 A5 CH651023 A5 CH 651023A5
- Authority
- CH
- Switzerland
- Prior art keywords
- group
- formula
- photosensitive
- diazoacetyl
- derivatives
- Prior art date
Links
- 239000000463 material Substances 0.000 title claims abstract description 71
- -1 derivatives of aromatic heterocyclic nitrides Chemical class 0.000 claims abstract description 34
- 150000001875 compounds Chemical class 0.000 claims description 48
- 239000000126 substance Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 17
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 238000004042 decolorization Methods 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- ZSTBZBURMWJKSQ-UHFFFAOYSA-N 2-diazonio-1-phenylethenolate Chemical class N#[N+]C=C([O-])C1=CC=CC=C1 ZSTBZBURMWJKSQ-UHFFFAOYSA-N 0.000 claims description 3
- 150000008049 diazo compounds Chemical class 0.000 claims description 3
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 230000009257 reactivity Effects 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 230000005855 radiation Effects 0.000 description 27
- 239000000243 solution Substances 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000004458 analytical method Methods 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 230000003287 optical effect Effects 0.000 description 16
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000002244 precipitate Substances 0.000 description 15
- 239000010453 quartz Substances 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 230000003595 spectral effect Effects 0.000 description 15
- 238000011161 development Methods 0.000 description 13
- NAGRQZLSRVOXLI-UHFFFAOYSA-N 2-diazo-1-(2,6-dichloropyrimidin-4-yl)ethanone Chemical compound ClC1=NC(=CC(=N1)Cl)C(C=[N+]=[N-])=O NAGRQZLSRVOXLI-UHFFFAOYSA-N 0.000 description 10
- 206010034972 Photosensitivity reaction Diseases 0.000 description 10
- 238000000354 decomposition reaction Methods 0.000 description 10
- 230000036211 photosensitivity Effects 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- YGPKEGAGPNUVNG-UHFFFAOYSA-N 2-diazonio-1-pyridin-2-ylethenolate Chemical class [N-]=[N+]=CC(=O)C1=CC=CC=N1 YGPKEGAGPNUVNG-UHFFFAOYSA-N 0.000 description 9
- PJKKWVLFVBSFBO-UHFFFAOYSA-N 2-diazonio-1-quinolin-2-ylethenolate Chemical class C1=CC=CC2=NC(C(=C[N+]#N)[O-])=CC=C21 PJKKWVLFVBSFBO-UHFFFAOYSA-N 0.000 description 9
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 9
- 229910052753 mercury Inorganic materials 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- 230000035945 sensitivity Effects 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 102100026109 F-box only protein 43 Human genes 0.000 description 7
- 101100333307 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) EMI2 gene Proteins 0.000 description 7
- 101150037264 fbxo43 gene Proteins 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 102100028284 Collagen alpha-1(XXVI) chain Human genes 0.000 description 6
- 101000860862 Homo sapiens Collagen alpha-1(XXVI) chain Proteins 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- ZRKWMRDKSOPRRS-UHFFFAOYSA-N N-Methyl-N-nitrosourea Chemical compound O=NN(C)C(N)=O ZRKWMRDKSOPRRS-UHFFFAOYSA-N 0.000 description 5
- 206010034960 Photophobia Diseases 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000084 colloidal system Substances 0.000 description 5
- 208000013469 light sensitivity Diseases 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- GDJZKZHFJIVCPI-UHFFFAOYSA-N 1-[2,6-bis(2-diazoacetyl)pyridin-4-yl]-2-diazoethanone Chemical compound [N+](=[N-])=CC(=O)C1=NC(=CC(=C1)C(C=[N+]=[N-])=O)C(C=[N+]=[N-])=O GDJZKZHFJIVCPI-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 102100032066 EMI domain-containing protein 1 Human genes 0.000 description 4
- 101000921258 Homo sapiens EMI domain-containing protein 1 Proteins 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- 229910052601 baryte Inorganic materials 0.000 description 4
- 239000010428 baryte Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 238000004020 luminiscence type Methods 0.000 description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- PXQPEWDEAKTCGB-UHFFFAOYSA-N orotic acid Chemical compound OC(=O)C1=CC(=O)NC(=O)N1 PXQPEWDEAKTCGB-UHFFFAOYSA-N 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- WJTDWCQXAVZSPO-UHFFFAOYSA-N 2-diazo-1-[6-(2-diazoacetyl)-5-nitropyridin-2-yl]ethanone Chemical compound [N+](=[N-])=CC(=O)C1=NC(=CC=C1[N+](=O)[O-])C(C=[N+]=[N-])=O WJTDWCQXAVZSPO-UHFFFAOYSA-N 0.000 description 3
- YEONCZYIBIRMQW-UHFFFAOYSA-N 2-diazonio-1-[2-(2-diazonio-1-oxidoethenyl)pyridin-4-yl]ethenolate Chemical compound N#[N+]C=C([O-])C1=CC=NC(C([O-])=C[N+]#N)=C1 YEONCZYIBIRMQW-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 3
- BKKKZBZTBBNXRY-UHFFFAOYSA-N [N+](=[N-])=CC(=O)C1=CC=NC=N1 Chemical class [N+](=[N-])=CC(=O)C1=CC=NC=N1 BKKKZBZTBBNXRY-UHFFFAOYSA-N 0.000 description 3
- 230000004907 flux Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- JHWJJKGOJXOOBI-UHFFFAOYSA-N 1-(2,6-diaminopyrimidin-4-yl)-2-diazoethanone Chemical compound NC1=NC(=CC(=N1)N)C(C=[N+]=[N-])=O JHWJJKGOJXOOBI-UHFFFAOYSA-N 0.000 description 2
- TWYYQQBGGSOKSN-UHFFFAOYSA-N 1-(2-chloro-6-methoxypyrimidin-4-yl)-2-diazoethanone Chemical compound ClC1=NC(=CC(=N1)OC)C(C=[N+]=[N-])=O TWYYQQBGGSOKSN-UHFFFAOYSA-N 0.000 description 2
- GOXLWVFOHPWMTN-UHFFFAOYSA-N 1-(2-chloro-6-piperidin-1-ylpyrimidin-4-yl)-2-diazoethanone Chemical compound ClC1=NC(=CC(=N1)N1CCCCC1)C(C=[N+]=[N-])=O GOXLWVFOHPWMTN-UHFFFAOYSA-N 0.000 description 2
- ZQCJGBAXYRMIRK-UHFFFAOYSA-N 2-diazo-1-(4-methylquinolin-2-yl)ethanone Chemical compound CC1=CC(=NC2=CC=CC=C12)C(C=[N+]=[N-])=O ZQCJGBAXYRMIRK-UHFFFAOYSA-N 0.000 description 2
- QQSZLLLUUZMVAR-UHFFFAOYSA-N 2-diazo-1-(5-nitroquinolin-2-yl)ethanone Chemical compound [N+](=O)([O-])C1=C2C=CC(=NC2=CC=C1)C(C=[N+]=[N-])=O QQSZLLLUUZMVAR-UHFFFAOYSA-N 0.000 description 2
- JGOBQPMRVAOMPF-UHFFFAOYSA-N 2-diazo-1-(8-nitroquinolin-2-yl)ethanone Chemical compound [N+](=O)([O-])C=1C=CC=C2C=CC(=NC=12)C(C=[N+]=[N-])=O JGOBQPMRVAOMPF-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- XXTZHYXQVWRADW-UHFFFAOYSA-N diazomethanone Chemical compound [N]N=C=O XXTZHYXQVWRADW-UHFFFAOYSA-N 0.000 description 2
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012434 nucleophilic reagent Substances 0.000 description 2
- 229960005010 orotic acid Drugs 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 238000005375 photometry Methods 0.000 description 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- GWHOGODUVLQCEB-UHFFFAOYSA-N pyridine-2,6-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=N1 GWHOGODUVLQCEB-UHFFFAOYSA-N 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 230000004304 visual acuity Effects 0.000 description 2
- QTICGDDDDQNBPF-UHFFFAOYSA-N 1-(2-chloro-6-phenyldiazenylpyrimidin-4-yl)-2-diazoethanone Chemical compound ClC1=NC(=CC(=N1)N=NC1=CC=CC=C1)C(C=[N+]=[N-])=O QTICGDDDDQNBPF-UHFFFAOYSA-N 0.000 description 1
- NUYJCMGJLNVOML-UHFFFAOYSA-N 2,6-dichloropyrimidine-4-carbonyl chloride Chemical compound ClC(=O)C1=CC(Cl)=NC(Cl)=N1 NUYJCMGJLNVOML-UHFFFAOYSA-N 0.000 description 1
- MOXUTXQEKYPKKS-UHFFFAOYSA-N 2,6-dichloropyrimidine-4-carboxylic acid Chemical compound OC(=O)C1=CC(Cl)=NC(Cl)=N1 MOXUTXQEKYPKKS-UHFFFAOYSA-N 0.000 description 1
- AETHUDGJSSKZKT-UHFFFAOYSA-N 2,6-dimethyl-3-nitropyridine Chemical compound CC1=CC=C([N+]([O-])=O)C(C)=N1 AETHUDGJSSKZKT-UHFFFAOYSA-N 0.000 description 1
- QGOKNOLJKOHLCT-UHFFFAOYSA-N 2-diazo-1-(4-nitroquinolin-2-yl)ethanone Chemical compound [N+](=O)([O-])C1=CC(=NC2=CC=CC=C12)C(C=[N+]=[N-])=O QGOKNOLJKOHLCT-UHFFFAOYSA-N 0.000 description 1
- NLNDOAYOEOMKRU-UHFFFAOYSA-N 2-diazo-1-[6-(2-diazoacetyl)pyridin-2-yl]ethanone Chemical compound [N+](=[N-])=CC(=O)C1=NC(=CC=C1)C(C=[N+]=[N-])=O NLNDOAYOEOMKRU-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- PQVWSOJILKYXCV-UHFFFAOYSA-N 2-quinolin-2-ylacetyl chloride Chemical compound C1=CC=CC2=NC(CC(=O)Cl)=CC=C21 PQVWSOJILKYXCV-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 238000006218 Arndt-Eistert homologation reaction Methods 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- VEBPXNDNZWPPOJ-UHFFFAOYSA-N [N+](=[N-])=CC(=O)C1=NC=CC=N1 Chemical compound [N+](=[N-])=CC(=O)C1=NC=CC=N1 VEBPXNDNZWPPOJ-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- 229910001864 baryta Inorganic materials 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 239000002023 wood Substances 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
- G03C1/00—Photosensitive materials
- G03C1/695—Compositions containing azides as the photosensitive substances
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU3217544 | 1980-12-26 | ||
| SU803217545A SU1232666A1 (ru) | 1980-12-26 | 1980-12-26 | 3-Фенил-4-диазоацетилсиднон в качестве светочувствительного компонента в актинометрах УФ-излучени |
| SU3217543 | 1980-12-26 | ||
| SU3217542 | 1980-12-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH651023A5 true CH651023A5 (de) | 1985-08-30 |
Family
ID=27484904
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH501882A CH651023A5 (de) | 1980-12-26 | 1981-12-25 | Alpha-diazoacetylderivate von aromatischen stickstoffhaltigen heterocyclen und ein daraus gebildetes lichtempfindliches material. |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS57502259A (en:Method) |
| CH (1) | CH651023A5 (en:Method) |
| DE (1) | DE3152651T (en:Method) |
| NL (1) | NL8120511A (en:Method) |
| SE (1) | SE8204755D0 (en:Method) |
| WO (1) | WO1982002258A1 (en:Method) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3486899A (en) * | 1965-12-13 | 1969-12-30 | Minnesota Mining & Mfg | Imagewise photochromic responsive element and process |
| JPS5646141B2 (en:Method) * | 1974-02-05 | 1981-10-31 | ||
| US4220708A (en) * | 1977-07-22 | 1980-09-02 | Heller Harold G | Photochromic compounds |
-
1981
- 1981-12-25 CH CH501882A patent/CH651023A5/de not_active IP Right Cessation
- 1981-12-25 JP JP82500892A patent/JPS57502259A/ja active Pending
- 1981-12-25 WO PCT/SU1981/000079 patent/WO1982002258A1/ru active Application Filing
- 1981-12-25 DE DE19813152651 patent/DE3152651T/de not_active Withdrawn
- 1981-12-26 NL NL8120511A patent/NL8120511A/nl not_active Application Discontinuation
-
1982
- 1982-08-18 SE SE8204755A patent/SE8204755D0/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO1982002258A1 (fr) | 1982-07-08 |
| JPS57502259A (en:Method) | 1982-12-23 |
| SE8204755L (sv) | 1982-08-18 |
| SE8204755D0 (sv) | 1982-08-18 |
| NL8120511A (nl) | 1982-11-01 |
| DE3152651T (de) | 1983-02-10 |
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