DE2237760C3 - Photographisches Aufzeichnungsmaterial mit einer ein Organoazid enthaltenden Schicht sowie Verfahren zur Herstellung photographischer Bilder - Google Patents
Photographisches Aufzeichnungsmaterial mit einer ein Organoazid enthaltenden Schicht sowie Verfahren zur Herstellung photographischer BilderInfo
- Publication number
- DE2237760C3 DE2237760C3 DE2237760A DE2237760A DE2237760C3 DE 2237760 C3 DE2237760 C3 DE 2237760C3 DE 2237760 A DE2237760 A DE 2237760A DE 2237760 A DE2237760 A DE 2237760A DE 2237760 C3 DE2237760 C3 DE 2237760C3
- Authority
- DE
- Germany
- Prior art keywords
- recording material
- image
- azide
- complex
- phosphine
- 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 claims description 114
- 238000000034 method Methods 0.000 title claims description 23
- -1 substituted alkyl radical Chemical class 0.000 claims description 98
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 44
- 150000001540 azides Chemical class 0.000 claims description 41
- 230000005855 radiation Effects 0.000 claims description 29
- 238000004519 manufacturing process Methods 0.000 claims description 26
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 23
- 150000003254 radicals Chemical class 0.000 claims description 20
- 150000005840 aryl radicals Chemical class 0.000 claims description 13
- 150000004714 phosphonium salts Chemical class 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 11
- 150000001450 anions Chemical class 0.000 claims description 10
- 239000011230 binding agent Substances 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 9
- 230000003213 activating effect Effects 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000007983 Tris buffer Substances 0.000 claims description 7
- 229910052723 transition metal Inorganic materials 0.000 claims description 7
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 7
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 6
- 150000003003 phosphines Chemical class 0.000 claims description 6
- JRNGUTKWMSBIBF-UHFFFAOYSA-N naphthalene-2,3-diol Chemical compound C1=CC=C2C=C(O)C(O)=CC2=C1 JRNGUTKWMSBIBF-UHFFFAOYSA-N 0.000 claims description 5
- 150000003624 transition metals Chemical class 0.000 claims description 5
- DOXPTTBJQKIAQV-UHFFFAOYSA-N 4-(4-azidophenyl)morpholine Chemical compound C1=CC(N=[N+]=[N-])=CC=C1N1CCOCC1 DOXPTTBJQKIAQV-UHFFFAOYSA-N 0.000 claims description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 4
- RLLBDYRUEHTODT-UHFFFAOYSA-N 3-azidobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(N=[N+]=[N-])=C1 RLLBDYRUEHTODT-UHFFFAOYSA-N 0.000 claims description 3
- UZEFHQIOSJWWSB-UHFFFAOYSA-N 4-azidobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(N=[N+]=[N-])C=C1 UZEFHQIOSJWWSB-UHFFFAOYSA-N 0.000 claims description 3
- YURUKVUJGYBZDU-UHFFFAOYSA-N 4-azidobenzonitrile Chemical compound [N-]=[N+]=NC1=CC=C(C#N)C=C1 YURUKVUJGYBZDU-UHFFFAOYSA-N 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 230000005670 electromagnetic radiation Effects 0.000 claims description 3
- PIJRLNIZKMOPGM-UHFFFAOYSA-N phenyl 4-azidobenzoate Chemical compound N(=[N+]=[N-])C1=CC=C(C(=O)OC2=CC=CC=C2)C=C1 PIJRLNIZKMOPGM-UHFFFAOYSA-N 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- FQCIVXJPSZVUCI-UHFFFAOYSA-N (1-hydroxynaphthalen-2-yl)-piperidin-1-ylmethanone Chemical compound C1=CC2=CC=CC=C2C(O)=C1C(=O)N1CCCCC1 FQCIVXJPSZVUCI-UHFFFAOYSA-N 0.000 claims description 2
- UOVVGTYACLGOIL-UHFFFAOYSA-N 1-azido-4-bromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=C(N=[N+]=[N-])C2=C1 UOVVGTYACLGOIL-UHFFFAOYSA-N 0.000 claims description 2
- KYYBIHHJZBKCGA-UHFFFAOYSA-N 2-methylquinoline;hydroiodide Chemical group I.C1=CC=CC2=NC(C)=CC=C21 KYYBIHHJZBKCGA-UHFFFAOYSA-N 0.000 claims description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 2
- 229950011260 betanaphthol Drugs 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- HTVPAACTHAQQAS-UHFFFAOYSA-N n-(2-hydroxy-4-methylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(C)C=C1O HTVPAACTHAQQAS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- CTRLRINCMYICJO-UHFFFAOYSA-N phenyl azide Chemical compound [N-]=[N+]=NC1=CC=CC=C1 CTRLRINCMYICJO-UHFFFAOYSA-N 0.000 claims description 2
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 claims description 2
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 claims description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims 2
- 229910052742 iron Inorganic materials 0.000 claims 2
- XPCUBQRMSPSPFN-UHFFFAOYSA-M (2-methyl-3-oxocyclohexyl)-tris(4-methylphenyl)phosphanium perchlorate Chemical compound Cl(=O)(=O)(=O)[O-].CC1C(CCCC1[P+](C1=CC=C(C=C1)C)(C1=CC=C(C=C1)C)C1=CC=C(C=C1)C)=O XPCUBQRMSPSPFN-UHFFFAOYSA-M 0.000 claims 1
- VMJAMBRVERLXRZ-UHFFFAOYSA-M (3-oxo-1-phenylbutyl)-triphenylphosphanium perchlorate Chemical compound Cl(=O)(=O)(=O)[O-].O=C(CC(C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C VMJAMBRVERLXRZ-UHFFFAOYSA-M 0.000 claims 1
- VIAJRIXODOQXIC-UHFFFAOYSA-N 4-(azidomethyl)benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(CN=[N+]=[N-])C=C1 VIAJRIXODOQXIC-UHFFFAOYSA-N 0.000 claims 1
- QGSWHVLSSSEOSN-UHFFFAOYSA-N 5-azidoisoquinoline Chemical compound N1=CC=C2C(N=[N+]=[N-])=CC=CC2=C1 QGSWHVLSSSEOSN-UHFFFAOYSA-N 0.000 claims 1
- AFQQNBLNHLSKBR-UHFFFAOYSA-M [Br-].O=C(CC(C)[P+](C1=CC=C(C=C1)C)(C1=CC=C(C=C1)C)C1=CC=C(C=C1)C)C Chemical compound [Br-].O=C(CC(C)[P+](C1=CC=C(C=C1)C)(C1=CC=C(C=C1)C)C1=CC=C(C=C1)C)C AFQQNBLNHLSKBR-UHFFFAOYSA-M 0.000 claims 1
- OAVMBZWGYHMOSC-UHFFFAOYSA-M [Cl-].O=C(CC(C)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C Chemical compound [Cl-].O=C(CC(C)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C OAVMBZWGYHMOSC-UHFFFAOYSA-M 0.000 claims 1
- WLNIECNLFRHWOI-UHFFFAOYSA-N [[4-(4-diazonioimino-3-methoxycyclohexa-2,5-dien-1-ylidene)-2-methoxycyclohexa-2,5-dien-1-ylidene]hydrazinylidene]azanide Chemical group C1=C(N=[N+]=[N-])C(OC)=CC(C=2C=C(OC)C(N=[N+]=[N-])=CC=2)=C1 WLNIECNLFRHWOI-UHFFFAOYSA-N 0.000 claims 1
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 claims 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims 1
- GGOZGYRTNQBSSA-UHFFFAOYSA-N pyridine-2,3-diol Chemical compound OC1=CC=CN=C1O GGOZGYRTNQBSSA-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 35
- 239000002585 base Substances 0.000 description 25
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 20
- SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 description 18
- 239000000975 dye Substances 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
- 229910021529 ammonia Inorganic materials 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- BWCCVIRGUMYIHE-UHFFFAOYSA-N phosphane;azide Chemical compound P.[N-]=[N+]=[N-] BWCCVIRGUMYIHE-UHFFFAOYSA-N 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 9
- 230000006641 stabilisation Effects 0.000 description 9
- 238000011105 stabilization Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 230000004913 activation Effects 0.000 description 5
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- 239000012190 activator Substances 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 239000012670 alkaline solution Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 3
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- QNCXQCFMEZPKDW-UHFFFAOYSA-N 2-(4-azidophenyl)-1H-benzimidazole Chemical compound [N-]=[N+]=NC1=CC=C(C=C1)C1=NC2=CC=CC=C2N1 QNCXQCFMEZPKDW-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000009471 action Effects 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
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- XVDBWWRIXBMVJV-UHFFFAOYSA-N n-[bis(dimethylamino)phosphanyl]-n-methylmethanamine Chemical compound CN(C)P(N(C)C)N(C)C XVDBWWRIXBMVJV-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- JVXXKQIRGQDWOJ-UHFFFAOYSA-N naphthalene-2-carboxamide Chemical compound C1=CC=CC2=CC(C(=O)N)=CC=C21 JVXXKQIRGQDWOJ-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- GURKTTIRZFPBBT-UHFFFAOYSA-N (3-ethoxy-3-oxopropyl)-triphenylphosphanium Chemical compound C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCC(=O)OCC)C1=CC=CC=C1 GURKTTIRZFPBBT-UHFFFAOYSA-N 0.000 description 1
- BCNMNYUNSFNSSG-UHFFFAOYSA-N (4-azidophenyl)-phenylmethanone Chemical compound C1=CC(N=[N+]=[N-])=CC=C1C(=O)C1=CC=CC=C1 BCNMNYUNSFNSSG-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- CWHFCSKEIGMGLP-UHFFFAOYSA-N 1-(4-azidophenyl)sulfonylpyrrolidine-2,5-dione Chemical compound N(=[N+]=[N-])C1=CC=C(C=C1)S(=O)(=O)N1C(CCC1=O)=O CWHFCSKEIGMGLP-UHFFFAOYSA-N 0.000 description 1
- BVKCTCWYHGXELK-UHFFFAOYSA-N 1-azido-4-(4-azidophenoxy)benzene Chemical compound C1=CC(N=[N+]=[N-])=CC=C1OC1=CC=C(N=[N+]=[N-])C=C1 BVKCTCWYHGXELK-UHFFFAOYSA-N 0.000 description 1
- DWBCXGZVCAKDGO-UHFFFAOYSA-N 1-azido-4-[(4-azidophenyl)disulfanyl]benzene Chemical compound C1=CC(N=[N+]=[N-])=CC=C1SSC1=CC=C(N=[N+]=[N-])C=C1 DWBCXGZVCAKDGO-UHFFFAOYSA-N 0.000 description 1
- BIPJTJYGWKQWDU-UHFFFAOYSA-N 1-azido-5-methoxynaphthalene Chemical compound N(=[N+]=[N-])C1=CC=CC2=C(C=CC=C12)OC BIPJTJYGWKQWDU-UHFFFAOYSA-N 0.000 description 1
- XHHBSJZGQKEUGJ-UHFFFAOYSA-N 1-azido-9H-carbazole Chemical compound C12=CC=CC=C2NC2=C1C=CC=C2N=[N+]=[N-] XHHBSJZGQKEUGJ-UHFFFAOYSA-N 0.000 description 1
- HYISGPFBRUIUNB-UHFFFAOYSA-N 1-azidonaphthalene Chemical compound C1=CC=C2C(N=[N+]=[N-])=CC=CC2=C1 HYISGPFBRUIUNB-UHFFFAOYSA-N 0.000 description 1
- KUXZUKHDEHMISS-UHFFFAOYSA-N 1-hydroxy-n-[3-[(1-hydroxynaphthalene-2-carbonyl)amino]phenyl]naphthalene-2-carboxamide Chemical compound C1=CC=CC2=C(O)C(C(=O)NC=3C=CC=C(C=3)NC(=O)C3=C(C4=CC=CC=C4C=C3)O)=CC=C21 KUXZUKHDEHMISS-UHFFFAOYSA-N 0.000 description 1
- YEOGSEYGVSFBHS-UHFFFAOYSA-N 1-hydroxy-n-methylnaphthalene-2-carboxamide Chemical compound C1=CC=CC2=C(O)C(C(=O)NC)=CC=C21 YEOGSEYGVSFBHS-UHFFFAOYSA-N 0.000 description 1
- MRBHUTYSDDTIIF-UHFFFAOYSA-N 1-hydroxy-n-phenylnaphthalene-2-carboxamide Chemical compound C1=CC2=CC=CC=C2C(O)=C1C(=O)NC1=CC=CC=C1 MRBHUTYSDDTIIF-UHFFFAOYSA-N 0.000 description 1
- DHWLQJPHSAMUCH-UHFFFAOYSA-N 1h-benzo[a]carbazole Chemical compound C1=CC=CC2=NC3=C4CC=CC=C4C=CC3=C21 DHWLQJPHSAMUCH-UHFFFAOYSA-N 0.000 description 1
- QWWLQHYCSMVQFN-UHFFFAOYSA-N 2,3-dihydroxypropyl 4-azidobenzoate Chemical compound N(=[N+]=[N-])C1=CC=C(C(=O)OCC(O)CO)C=C1 QWWLQHYCSMVQFN-UHFFFAOYSA-N 0.000 description 1
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- PLBXFYFBJMNSHS-UHFFFAOYSA-N 2-azidoaniline Chemical class NC1=CC=CC=C1N=[N+]=[N-] PLBXFYFBJMNSHS-UHFFFAOYSA-N 0.000 description 1
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- 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
- G03F7/0085—Azides characterised by the non-macromolecular additives
-
- 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
- G03C1/52—Compositions containing diazo compounds as photosensitive substances
-
- 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
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16839271A | 1971-08-02 | 1971-08-02 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2237760A1 DE2237760A1 (de) | 1973-02-15 |
| DE2237760B2 DE2237760B2 (de) | 1974-03-14 |
| DE2237760C3 true DE2237760C3 (de) | 1974-10-31 |
Family
ID=22611323
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2237760A Expired DE2237760C3 (de) | 1971-08-02 | 1972-08-01 | Photographisches Aufzeichnungsmaterial mit einer ein Organoazid enthaltenden Schicht sowie Verfahren zur Herstellung photographischer Bilder |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3767409A (enExample) |
| JP (1) | JPS5038929B2 (enExample) |
| AU (1) | AU4519072A (enExample) |
| BE (1) | BE787019A (enExample) |
| CA (1) | CA986775A (enExample) |
| DE (1) | DE2237760C3 (enExample) |
| FR (1) | FR2148135B1 (enExample) |
| IT (1) | IT963593B (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2948324C2 (de) * | 1978-12-01 | 1993-01-14 | Hitachi, Ltd., Tokio/Tokyo | Lichtempfindliches Gemisch, enthaltend eine Bisazidverbindung, und Verfahren zur Bildung von Mustern |
| JPS5937540A (ja) * | 1982-08-26 | 1984-03-01 | Kimoto & Co Ltd | 感光性組成物及びその現像方法 |
| US4622284A (en) * | 1984-03-01 | 1986-11-11 | Digital Recording Corporation | Process of using metal azide recording media with laser |
| DE3615613A1 (de) * | 1986-05-09 | 1987-11-12 | Hoechst Ag | Lichtempfindliches gemisch und daraus hergestelltes lichtempfindliches aufzeichnungsmaterial |
| DE3615612A1 (de) * | 1986-05-09 | 1987-11-12 | Hoechst Ag | Lichtempfindliches gemisch und daraus hergestelltes lichtempfindliches aufzeichnungsmaterial |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1258265B (de) * | 1960-02-05 | 1968-01-04 | Eastman Kodak Co | Lichtempfindliche photographische Schicht |
| US3062650A (en) * | 1960-05-05 | 1962-11-06 | Eastman Kodak Co | Photographic printout system comprising an organic azide |
| US3275443A (en) * | 1963-08-14 | 1966-09-27 | Horizons Inc | Anti-fogging agents for an n-vinyl, organic halogen, dye former system |
| GB1054533A (enExample) * | 1964-06-25 | |||
| US3374094A (en) * | 1965-07-19 | 1968-03-19 | Horizons Inc | Lithographic plate made from an n-vinyl-amine and an organic halogen compound dispersed in an hydrophilic colloid |
| US3475176A (en) * | 1966-09-06 | 1969-10-28 | Eastman Kodak Co | Azide sensitized photosensitive prepolymer compositions |
| US3598585A (en) * | 1967-07-26 | 1971-08-10 | Bela Gaspar | Azido photohardenable colloid containing an immobile dye and process of using |
| DE1772813A1 (de) * | 1968-07-08 | 1971-06-09 | Agfa Gevaert Ag | Trockenkopierverfahren |
| US3594170A (en) * | 1968-10-03 | 1971-07-20 | Western Electric Co | Additives to negative photoresists which increase the sensitivity thereof |
-
1971
- 1971-08-02 US US00168392A patent/US3767409A/en not_active Expired - Lifetime
-
1972
- 1972-07-31 BE BE787019A patent/BE787019A/xx not_active IP Right Cessation
- 1972-07-31 IT IT27701/72A patent/IT963593B/it active
- 1972-08-01 FR FR727227639A patent/FR2148135B1/fr not_active Expired
- 1972-08-01 DE DE2237760A patent/DE2237760C3/de not_active Expired
- 1972-08-01 CA CA148,412A patent/CA986775A/en not_active Expired
- 1972-08-01 AU AU45190/72A patent/AU4519072A/en not_active Expired
- 1972-08-02 JP JP47077004A patent/JPS5038929B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2237760B2 (de) | 1974-03-14 |
| US3767409A (en) | 1973-10-23 |
| BE787019A (fr) | 1972-11-16 |
| FR2148135A1 (enExample) | 1973-03-11 |
| AU4519072A (en) | 1974-02-07 |
| DE2237760A1 (de) | 1973-02-15 |
| FR2148135B1 (enExample) | 1974-07-26 |
| JPS5038929B2 (enExample) | 1975-12-13 |
| JPS4825518A (enExample) | 1973-04-03 |
| CA986775A (en) | 1976-04-06 |
| IT963593B (it) | 1974-01-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |