US2151532A - Light-sensitive layers - Google Patents
Light-sensitive layers Download PDFInfo
- Publication number
- US2151532A US2151532A US109550A US10955036A US2151532A US 2151532 A US2151532 A US 2151532A US 109550 A US109550 A US 109550A US 10955036 A US10955036 A US 10955036A US 2151532 A US2151532 A US 2151532A
- Authority
- US
- United States
- Prior art keywords
- diam
- compound
- diazo
- light
- compounds
- 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 - Lifetime
Links
- 150000008049 diazo compounds Chemical class 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 150000001555 benzenes Chemical class 0.000 description 9
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 125000001302 tertiary amino group Chemical group 0.000 description 4
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 3
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 3
- 239000001166 ammonium sulphate Substances 0.000 description 3
- 235000011130 ammonium sulphate Nutrition 0.000 description 3
- 150000001716 carbazoles Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 150000002475 indoles Chemical class 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- -1 N-benzoyl-tetrahydroaminoquinoline Chemical compound 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000001164 aluminium sulphate Substances 0.000 description 2
- 235000011128 aluminium sulphate Nutrition 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000005010 aminoquinolines Chemical class 0.000 description 2
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- BUACSMWVFUNQET-UHFFFAOYSA-H dialuminum;trisulfate;hydrate Chemical compound O.[Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O BUACSMWVFUNQET-UHFFFAOYSA-H 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000000802 nitrating effect Effects 0.000 description 2
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 2
- 150000003248 quinolines Chemical class 0.000 description 2
- 229950000244 sulfanilic acid Drugs 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- AIPJZPPOFWCJRC-UHFFFAOYSA-N 1,2-dichloro-3-(chloromethyl)benzene Chemical compound ClCC1=CC=CC(Cl)=C1Cl AIPJZPPOFWCJRC-UHFFFAOYSA-N 0.000 description 1
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- QCKVUTCVXGLZQC-UHFFFAOYSA-N 3-hydroxy-1,2-dimethyl-1,2,3,9-tetrahydrocarbazol-4-one Chemical class N1C2=CC=CC=C2C2=C1C(C)C(C)C(O)C2=O QCKVUTCVXGLZQC-UHFFFAOYSA-N 0.000 description 1
- WREVVZMUNPAPOV-UHFFFAOYSA-N 8-aminoquinoline Chemical compound C1=CN=C2C(N)=CC=CC2=C1 WREVVZMUNPAPOV-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010034960 Photophobia Diseases 0.000 description 1
- 239000004133 Sodium thiosulphate Substances 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229940058934 aminoquinoline antimalarials Drugs 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- WCTXJBYIXVVFCF-UHFFFAOYSA-M chlorotin Chemical compound [Sn]Cl WCTXJBYIXVVFCF-UHFFFAOYSA-M 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 description 1
- 208000013469 light sensitivity Diseases 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
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- RJSRSRITMWVIQT-UHFFFAOYSA-N quinolin-6-amine Chemical compound N1=CC=CC2=CC(N)=CC=C21 RJSRSRITMWVIQT-UHFFFAOYSA-N 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 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
- G03C1/52—Compositions containing diazo compounds as photosensitive substances
- G03C1/54—Diazonium salts or diazo anhydrides
Definitions
- the present invention relates to improved light-sensitive layers.
- diazocompounds are employed for the production of light-sensitive layers which diazo compounds have a hydro:
- the said hydrogenated ring fused with the benzene nucleus containing the diazo group wherein the said hydrogenated ring consists of at least tour carbon atoms and one tertiary amino group having its nitrogen atom in the said hydrogenated ring.
- diazo compounds of hydrogenated quinolines which have a substituent attached to the nitrogen of the hydrogenated ring, highly sensitive strongly colored layers are produced which, in combination with the usual azo components, give pictures in dark lines.
- the non-hydrogenated aminoquinolines yield diazo compounds which are un- 45 suitable for the diazo-type process, because they are decomposable, notcapable of being completely bleached and of disadvantageous shade.
- the diazo compounds of. hydrogenated indoles and carbazoles which have a substituent attached to the nitrogen of the hydrogenated ring for instance, alkyl or aralkyl, behave similarly to the hydrogenated diam-quinolines.
- the compounds which are employed accord- 55 ing to the invention have a substituent attached to the nitrogen of the hydrogenized ring, for instance, alkyl or aralkyl.
- a substituent attached to the nitrogen of the hydrogenized ring for instance, alkyl or aralkyl.
- compounds are used in which the diazo-group is in paraposition to the nitrogen of the hydrogenized ring.
- the nucleus containing the diazo-group may also contain substituents, for instance halogen, alkoxy-groups or the like.
- the amines which serve asparent materials for the new diamocompounds may be made by known methods. Advantageously they are produced by coupling the hydrogenized quinoline, indole or carbazole with a diam-compound, for example diazotized sulphanilic acid, and then reducing the dyestufi produced. The hydrogenized amines obtained in this manner are then further diatotized by any known process.
- the diazo-compound may be applied alone or together with an azo-component. There'may be added to the layers and pictures metal salts,
- thiourea and other additions which have hitherto been used in the diam-type process.
- the picture is developed in known manner by a vapor, for example ammonia or steam or by a developing solution, depending upon whether the diazocompound exists in the layer alone or together with an azo-component, and if desired in presence of alkali or a substance of alkaline action.
- Example 2 81 grams of the tin chloride double salt of the diam-compound from N-bensyl-1z2z3z4-tet- I'lhldm-S-m-B-aminoquinollne are dissolved in 1 liter of water and tosether with the additions named in Example 1 and prints obtained-as usual. By developing with the developer prescribed in Example 1 black-blue lines are obtained.
- the diam-compounds named in this Example may be made by coupling the corresponding 1:2:3z4-tetrahvdro-3-oxyquinoline with dialotined sulphanilic acid and reducing the arcdyeatufl to the corresponding tetrahydro-S-oxymaythenbedi zotised' intheusualmanner.
- a solution 01' 31 grams of the tin chloride double salt of thediaso-compound from N-benaoyl-1:2:8:4-tetrahydro-8 aminoquinoline are dissolved in 1 liter of 'water together with the additions named in Example 1 and the solution is applied to paper. velopment are in deep brown lines.
- the amino-compound may be dinoticed in the usual manner.- Instead of the diam-compound from N-benzoyl-tetrahydroaminoquinoline that from N-bensoyl-1:2:3:4-tetra-. hydro-:8diethoxy-6-aminoquinoline may be used.
- the prints obtained on de- H. Km 8 Ha I The print may be developed with the developer named in Example 1, whereby black-brown lines are obtained.
- Example 7 instead of the diasommpound used in Example 6 34.8 grams of the tin chloride double salt of the diam-compound from 5-amino-2 :8- dimethyl-N-benzyl-2:3-dihydroindole are used; with the same developer as is prescribed in Example 1 more black-brown tones are obtained.
- Chloro-tin double salt of the diam-compound .irom G-amino-Q-ethylhelahydrocarbamle 3g ries and hydrocarbazole series are obtainable from the hydroindoles or hydrocarbazoles, respectively, which can be made in the known manner by suitable reduction, (for example, with tin and hydrochloric acid) of the indoles or carbazoles, respectively.
- the obtained compounds are alkylated or aralkylated and then further converted, as described in Example 2.
- a light sensitive layer comprising as the light sensitive substance a diam compound of a substance selected from the group consisting of tertiary hydrogenized quinolines, tertiary hydrogenized indoles and tertiary hydrogenized carbazoles.
- a light sensitive layer comprising as light sensitive substance the dlazo-compound from 2' :6'-dichloro-N-benzyl-1:2:3:4- tetrahydro 6 alminoquinoline.
- a light sensitive layer comprising as light sensitive substance the diazo-compound from N-benzyl-l:2:3:-i-tetrahydro-3 oxy 6 aminoquinoline.
- a light sensitive layer comprising as the light sensitive substance a diam-compound which has a hydrogenated ring fused with the benzene nucleus containing the diazo-group wherein the said hydrogenated ring consists of at least four carbon atoms and one tertiary amino group having its nitrogen atom in the ring.
- a light sensitive layer comprising as the light sensitive substance a diam-compound which has a hydrogenated ring fused with the benzene nucleus containing the diam-group wherein the said hydrogenated ring consists t at least four carbon atoms and one tertiary amino group having its nitrogen atom in the ring and attached to the said benzene nucleus in para-position to the said diam-group.
- a light sensitive layer comprising as the light sensitive substance a diazo-compound which has a hydrogenated ring fused with the benzene nucleus containing the diazo-group wherein the said hydrogenated ring consists of at least four carbon atoms and one nitrogen atom which latter carries a benzyl residue as substituent and is attached to the said benzene nucleus in para-position to the said diazo-group.
- a light sensitive layer comprising as the light sensitive substance a diam-compound which has a hydrogenated ring fused with the benzene nucleus containing the diazo-group, the said hydrogenated ring consisting of at least four carbon atoms and one tertiary amino group having its nitrogen atom in the ring and attached to the said benzene nucleus in para-position to the said diazo-group wherein the said benzene nucleus carries two alkoxy groups in 5- and 8- positions as substituents.
- a light sensitive layer according to claim 1, wherein the diazo-group of the said diazo-compound stands in para-position to the nitrogen atom or the hydrogenated ring.
- a light sensitive layer comprising as light sensitive substance the diam-compound from N-benzoyl-l :2 :3z4-tetrahydro-5z8- cliethoxy 6 aminoquinoline.
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Color Printing (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Paper (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK140012D DE676394C (de) | 1935-11-14 | 1935-11-14 | Verfahren zur Herstellung von lichtempfindlichen Schichten fuer die Diazotypie |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2151532A true US2151532A (en) | 1939-03-21 |
Family
ID=7249558
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US109550A Expired - Lifetime US2151532A (en) | 1935-11-14 | 1936-11-06 | Light-sensitive layers |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US2151532A (enrdf_load_stackoverflow) |
| BE (1) | BE418328A (enrdf_load_stackoverflow) |
| DE (1) | DE676394C (enrdf_load_stackoverflow) |
| FR (1) | FR813263A (enrdf_load_stackoverflow) |
| GB (1) | GB467145A (enrdf_load_stackoverflow) |
| NL (1) | NL45511C (enrdf_load_stackoverflow) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2439901A (en) * | 1941-12-27 | 1948-04-20 | Henry T Neumann | Method for producing colored photographs |
| US2500099A (en) * | 1945-12-20 | 1950-03-07 | Gen Aniline & Film Corp | Diazo sulfonate light-sensitive element containing a diketone azo component |
| US2613149A (en) * | 1947-10-29 | 1952-10-07 | Gen Aniline & Film Corp | Diazotype photoprinting material |
| US2657141A (en) * | 1947-07-14 | 1953-10-27 | Grinten Chem L V D | Diazotype developer composition containing a potassium borate and process of using same |
| US3297443A (en) * | 1963-03-19 | 1967-01-10 | Universal Oil Prod Co | Light sensitive quinoline diazo compounds |
| US3452026A (en) * | 1966-03-15 | 1969-06-24 | Bristol Myers Co | Substituted 1,2,3,4-tetrahydroquinolines |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB772517A (en) * | 1954-02-06 | 1957-04-17 | Kalle & Co Ag | Improvements in or relating to photo-mechanical reproduction |
-
0
- NL NL45511D patent/NL45511C/xx active
- BE BE418328D patent/BE418328A/xx unknown
-
1935
- 1935-11-14 DE DEK140012D patent/DE676394C/de not_active Expired
-
1936
- 1936-10-28 GB GB29304/36A patent/GB467145A/en not_active Expired
- 1936-11-06 US US109550A patent/US2151532A/en not_active Expired - Lifetime
- 1936-11-12 FR FR813263D patent/FR813263A/fr not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2439901A (en) * | 1941-12-27 | 1948-04-20 | Henry T Neumann | Method for producing colored photographs |
| US2500099A (en) * | 1945-12-20 | 1950-03-07 | Gen Aniline & Film Corp | Diazo sulfonate light-sensitive element containing a diketone azo component |
| US2657141A (en) * | 1947-07-14 | 1953-10-27 | Grinten Chem L V D | Diazotype developer composition containing a potassium borate and process of using same |
| US2613149A (en) * | 1947-10-29 | 1952-10-07 | Gen Aniline & Film Corp | Diazotype photoprinting material |
| US3297443A (en) * | 1963-03-19 | 1967-01-10 | Universal Oil Prod Co | Light sensitive quinoline diazo compounds |
| US3452026A (en) * | 1966-03-15 | 1969-06-24 | Bristol Myers Co | Substituted 1,2,3,4-tetrahydroquinolines |
Also Published As
| Publication number | Publication date |
|---|---|
| BE418328A (enrdf_load_stackoverflow) | |
| DE676394C (de) | 1939-06-05 |
| GB467145A (en) | 1937-06-11 |
| NL45511C (enrdf_load_stackoverflow) | |
| FR813263A (fr) | 1937-05-29 |
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