DE2118585A1 - Photosensitive Azidoverbindungen, photosensitive Zusammensetzungen und Bilderzeugungsverfahren - Google Patents
Photosensitive Azidoverbindungen, photosensitive Zusammensetzungen und BilderzeugungsverfahrenInfo
- Publication number
- DE2118585A1 DE2118585A1 DE19712118585 DE2118585A DE2118585A1 DE 2118585 A1 DE2118585 A1 DE 2118585A1 DE 19712118585 DE19712118585 DE 19712118585 DE 2118585 A DE2118585 A DE 2118585A DE 2118585 A1 DE2118585 A1 DE 2118585A1
- Authority
- DE
- Germany
- Prior art keywords
- image
- composition according
- azido
- photosensitive
- light
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims description 42
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 title claims description 11
- 238000003384 imaging method Methods 0.000 title description 14
- 238000000034 method Methods 0.000 claims description 32
- 238000010438 heat treatment Methods 0.000 claims description 22
- -1 trifluoroacetamido group Chemical group 0.000 claims description 19
- 239000004800 polyvinyl chloride Substances 0.000 claims description 14
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 13
- JVNYVLROXHWCQN-UHFFFAOYSA-N 1,8-diazidonaphthalene Chemical compound C1=CC(N=[N+]=[N-])=C2C(N=[N+]=[N-])=CC=CC2=C1 JVNYVLROXHWCQN-UHFFFAOYSA-N 0.000 claims description 11
- 230000007935 neutral effect Effects 0.000 claims description 10
- 230000005855 radiation Effects 0.000 claims description 9
- 238000000576 coating method Methods 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 239000011248 coating agent Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 4
- HUKPVYBUJRAUAG-UHFFFAOYSA-N 7-benzo[a]phenalenone Chemical compound C1=CC(C(=O)C=2C3=CC=CC=2)=C2C3=CC=CC2=C1 HUKPVYBUJRAUAG-UHFFFAOYSA-N 0.000 claims description 3
- 230000003213 activating effect Effects 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 claims description 3
- 239000004033 plastic Substances 0.000 claims description 3
- CJSDHUZPFFYHDW-UHFFFAOYSA-N 8-azidonaphthalen-1-amine Chemical compound C1=CC(N=[N+]=[N-])=C2C(N)=CC=CC2=C1 CJSDHUZPFFYHDW-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 230000004913 activation Effects 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229920003023 plastic Polymers 0.000 claims description 2
- 230000001678 irradiating effect Effects 0.000 claims 1
- LUYMTCKYBLJLHS-UHFFFAOYSA-N n-(8-azidonaphthalen-1-yl)-2,2,2-trifluoroacetamide Chemical compound C1=CC(N=[N+]=[N-])=C2C(NC(=O)C(F)(F)F)=CC=CC2=C1 LUYMTCKYBLJLHS-UHFFFAOYSA-N 0.000 claims 1
- 230000000007 visual effect Effects 0.000 claims 1
- 239000011230 binding agent Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
- 230000004048 modification Effects 0.000 description 8
- 238000012986 modification Methods 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 238000011161 development Methods 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- QNSQTJHTVQSWFR-UHFFFAOYSA-N [(4-diazonioiminocyclohexa-2,5-dien-1-ylidene)hydrazinylidene]azanide Chemical compound [N-]=[N+]=NC1=CC=C(N=[N+]=[N-])C=C1 QNSQTJHTVQSWFR-UHFFFAOYSA-N 0.000 description 6
- 239000011550 stock solution Substances 0.000 description 6
- 101150091111 ACAN gene Proteins 0.000 description 5
- 229920006385 Geon Polymers 0.000 description 5
- 239000000123 paper Substances 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 230000005284 excitation Effects 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- QKOCMCGGUNAXOY-UHFFFAOYSA-N 8-azidonaphthalen-1-ol Chemical compound C1=CC(N=[N+]=[N-])=C2C(O)=CC=CC2=C1 QKOCMCGGUNAXOY-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000008199 coating composition Substances 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 229920002799 BoPET Polymers 0.000 description 2
- 239000005041 Mylar™ Substances 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- FLCWLOFMVFESNI-UHFFFAOYSA-N acridine-9(10H)-thione Chemical compound C1=CC=C2C(=S)C3=CC=CC=C3NC2=C1 FLCWLOFMVFESNI-UHFFFAOYSA-N 0.000 description 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 229920006267 polyester film Polymers 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- JLAAZOCEPXLWOL-UHFFFAOYSA-N 1-azido-2-(2-azidophenyl)benzene Chemical group [N-]=[N+]=NC1=CC=CC=C1C1=CC=CC=C1N=[N+]=[N-] JLAAZOCEPXLWOL-UHFFFAOYSA-N 0.000 description 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- CBXFANAEPPIVEI-UHFFFAOYSA-N 2,7-diazidonaphthalene Chemical compound N(=[N+]=[N-])C1=CC2=CC(=CC=C2C=C1)N=[N+]=[N-] CBXFANAEPPIVEI-UHFFFAOYSA-N 0.000 description 1
- ZPQOMTOSHGDYGP-UHFFFAOYSA-N 4-azido-n,n-diethylaniline Chemical compound CCN(CC)C1=CC=C(N=[N+]=[N-])C=C1 ZPQOMTOSHGDYGP-UHFFFAOYSA-N 0.000 description 1
- KTXFVNGOXJWCOT-UHFFFAOYSA-N 4-azido-n-phenylaniline Chemical compound C1=CC(N=[N+]=[N-])=CC=C1NC1=CC=CC=C1 KTXFVNGOXJWCOT-UHFFFAOYSA-N 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- AMGGYDUPTVSWMV-UHFFFAOYSA-N N(=[N+]=[N-])C1=CC2=CC=C(C=C2C=C1)N=[N+]=[N-] Chemical compound N(=[N+]=[N-])C1=CC2=CC=C(C=C2C=C1)N=[N+]=[N-] AMGGYDUPTVSWMV-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- YCWHRQFZAWNQJE-UHFFFAOYSA-N [(5-diazonioiminonaphthalen-1-ylidene)hydrazinylidene]azanide Chemical compound C1=CC=C2C(N=[N+]=[N-])=CC=CC2=C1N=[N+]=[N-] YCWHRQFZAWNQJE-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- CIZVQWNPBGYCGK-UHFFFAOYSA-N benzenediazonium Chemical compound N#[N+]C1=CC=CC=C1 CIZVQWNPBGYCGK-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000005304 optical glass Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- CTRLRINCMYICJO-UHFFFAOYSA-N phenyl azide Chemical compound [N-]=[N+]=NC1=CC=CC=C1 CTRLRINCMYICJO-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920005596 polymer binder Polymers 0.000 description 1
- 239000002491 polymer binding agent Substances 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000001429 visible spectrum Methods 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2952770A | 1970-04-17 | 1970-04-17 | |
| US8212970A | 1970-10-19 | 1970-10-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2118585A1 true DE2118585A1 (de) | 1971-10-28 |
Family
ID=26705043
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712118585 Pending DE2118585A1 (de) | 1970-04-17 | 1971-04-16 | Photosensitive Azidoverbindungen, photosensitive Zusammensetzungen und Bilderzeugungsverfahren |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE765843A (enrdf_load_html_response) |
| DE (1) | DE2118585A1 (enrdf_load_html_response) |
| FR (1) | FR2089799A5 (enrdf_load_html_response) |
| GB (1) | GB1317852A (enrdf_load_html_response) |
-
1971
- 1971-04-16 FR FR7113588A patent/FR2089799A5/fr not_active Expired
- 1971-04-16 DE DE19712118585 patent/DE2118585A1/de active Pending
- 1971-04-16 BE BE765843A patent/BE765843A/xx unknown
- 1971-04-19 GB GB2613071A patent/GB1317852A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE765843A (enrdf_load_html_response) | 1971-10-18 |
| FR2089799A5 (enrdf_load_html_response) | 1972-01-07 |
| GB1317852A (en) | 1973-05-23 |
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