DE1172386B - Verfahren zur Herstellung von Farbstoff-entwicklersubstanzen - Google Patents
Verfahren zur Herstellung von Farbstoff-entwicklersubstanzenInfo
- Publication number
- DE1172386B DE1172386B DEJ11460A DEJ0011460A DE1172386B DE 1172386 B DE1172386 B DE 1172386B DE J11460 A DEJ11460 A DE J11460A DE J0011460 A DEJ0011460 A DE J0011460A DE 1172386 B DE1172386 B DE 1172386B
- Authority
- DE
- Germany
- Prior art keywords
- amino
- group
- anthraquinone
- general formula
- groups
- 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
- 238000000034 method Methods 0.000 title claims description 14
- 239000000126 substance Substances 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- -1 silver halide Chemical class 0.000 claims description 18
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 10
- 239000000047 product Substances 0.000 claims description 10
- 229910052709 silver Inorganic materials 0.000 claims description 10
- 239000004332 silver Substances 0.000 claims description 10
- 150000004056 anthraquinones Chemical class 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000005518 carboxamido group Chemical group 0.000 claims description 2
- 125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- 230000010933 acylation Effects 0.000 description 6
- 238000005917 acylation reaction Methods 0.000 description 6
- CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- BKNBVEKCHVXGPH-UHFFFAOYSA-N anthracene-1,4,9,10-tetrol Chemical compound C1=CC=C2C(O)=C3C(O)=CC=C(O)C3=C(O)C2=C1 BKNBVEKCHVXGPH-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- HOPTXGLZQCTTFG-UHFFFAOYSA-N 2-(2-aminopropyl)benzene-1,4-diol;hydrobromide Chemical compound Br.CC(N)CC1=CC(O)=CC=C1O HOPTXGLZQCTTFG-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JCBPETKZIGVZRE-UHFFFAOYSA-N 2-aminobutan-1-ol Chemical compound CCC(N)CO JCBPETKZIGVZRE-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- GWFVWUQOSJGENT-UHFFFAOYSA-N 6,7-dichloro-1,4-dihydroxyanthracene-9,10-dione Chemical compound O=C1C2=CC(Cl)=C(Cl)C=C2C(=O)C2=C1C(O)=CC=C2O GWFVWUQOSJGENT-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- MLKVIHYWQNWIPA-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)O.NC1=C(O)C=CC(=C1)O Chemical compound C(C1=CC=CC=C1)(=O)O.NC1=C(O)C=CC(=C1)O MLKVIHYWQNWIPA-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- VGHIUSVUNHGNBH-UHFFFAOYSA-N benzene-1,2-diol hydrobromide Chemical compound Br.C=1(C(=CC=CC1)O)O VGHIUSVUNHGNBH-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229960004926 chlorobutanol Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 1
- 229960005215 dichloroacetic acid Drugs 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229960001156 mitoxantrone Drugs 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000003643 water by type 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
- G03C8/00—Diffusion transfer processes or agents therefor; Photosensitive materials for such processes
- G03C8/02—Photosensitive materials characterised by the image-forming section
- G03C8/08—Photosensitive materials characterised by the image-forming section the substances transferred by diffusion consisting of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B43/00—Preparation of azo dyes from other azo compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
- C09B43/124—Preparation of azo dyes from other azo compounds by acylation of amino groups with monocarboxylic acids, carbamic esters or halides, mono- isocyanates, or haloformic acid esters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B6/00—Anthracene dyes not provided for above
-
- 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
- G03C8/00—Diffusion transfer processes or agents therefor; Photosensitive materials for such processes
- G03C8/02—Photosensitive materials characterised by the image-forming section
- G03C8/08—Photosensitive materials characterised by the image-forming section the substances transferred by diffusion consisting of organic compounds
- G03C8/10—Photosensitive materials characterised by the image-forming section the substances transferred by diffusion consisting of organic compounds of dyes or their precursors
- G03C8/12—Photosensitive materials characterised by the image-forming section the substances transferred by diffusion consisting of organic compounds of dyes or their precursors characterised by the releasing mechanism
- G03C8/14—Oxidation of the chromogenic substances
- G03C8/16—Oxidation of the chromogenic substances initially diffusible in alkaline environment
- G03C8/18—Dye developers
-
- 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
- G03C8/00—Diffusion transfer processes or agents therefor; Photosensitive materials for such processes
- G03C8/42—Structural details
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Structural Engineering (AREA)
- Architecture (AREA)
- Engineering & Computer Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Color Printing (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
- Developing Agents For Electrophotography (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41507354A | 1954-03-09 | 1954-03-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1172386B true DE1172386B (de) | 1964-06-18 |
Family
ID=23644267
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1066092D Pending DE1066092B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1954-03-09 | ||
| DEJ11460A Pending DE1172386B (de) | 1954-03-09 | 1955-03-09 | Verfahren zur Herstellung von Farbstoff-entwicklersubstanzen |
| DE19551419842 Pending DE1419842A1 (de) | 1954-03-09 | 1955-03-09 | Verfahren zur Herstellung von als Farbstoffentwicklersubstanzen geeigneten Farbstoffen der Azo- oder Anthrachinonreihe |
| DEI9925A Pending DE1196075B (de) | 1954-03-09 | 1955-03-09 | Verfahren zur Herstellung von Bildern nach dem Diffusionsuebertragungsverfahren |
| DEI11459A Pending DE1035660B (de) | 1954-03-09 | 1955-03-09 | Verfahren zur Herstellung von Farbentwicklersubstanzen |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1066092D Pending DE1066092B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1954-03-09 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19551419842 Pending DE1419842A1 (de) | 1954-03-09 | 1955-03-09 | Verfahren zur Herstellung von als Farbstoffentwicklersubstanzen geeigneten Farbstoffen der Azo- oder Anthrachinonreihe |
| DEI9925A Pending DE1196075B (de) | 1954-03-09 | 1955-03-09 | Verfahren zur Herstellung von Bildern nach dem Diffusionsuebertragungsverfahren |
| DEI11459A Pending DE1035660B (de) | 1954-03-09 | 1955-03-09 | Verfahren zur Herstellung von Farbentwicklersubstanzen |
Country Status (6)
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3053656A (en) * | 1954-07-01 | 1962-09-11 | Polaroid Corp | Photographic silver halide developers containing triazine rings |
| DE1299222B (de) * | 1958-10-16 | 1969-07-10 | Polaroid Corp | Photographisches Diffusionsverfahren |
| NL247650A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1959-01-26 | |||
| CA728646A (en) * | 1959-01-26 | 1966-02-22 | Green Milton | Photographic processes, compositions and products |
| US3230083A (en) * | 1959-04-02 | 1966-01-18 | Polaroid Corp | Photographic processes and products |
| NL126854C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1960-08-22 | |||
| DE1422849B1 (de) * | 1960-08-22 | 1970-07-09 | Eastman Kodak Co | Photographisches,mehrschichtiges Aufzeichnungsmaterial fuer das Farbstoffentwickler-Diffusionsverfahren |
| DE1422850B1 (de) * | 1960-08-22 | 1970-06-04 | Eastman Kodak Co | Farbstoffentwickler-Diffusionsverfahren zur Herstellung von mehrfarbigen Bildern |
| NL268156A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1960-08-22 | |||
| DE1168768B (de) * | 1960-08-22 | 1964-04-23 | Eastman Kodak Co | Photographisches Material und Verfahren fuer die Herstellung von mehrfarbigen Bildern nach einem Farbstoffentwicklersubstanzen verwendenden Diffusionsuebertragungsverfahren |
| BE610705A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1960-11-23 | |||
| BE607371A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1960-11-25 | |||
| US3255002A (en) * | 1961-03-09 | 1966-06-07 | Polaroid Corp | Color photographic process and product |
| BE614794A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1961-03-09 | |||
| US3239339A (en) * | 1961-05-05 | 1966-03-08 | Polaroid Corp | Novel photographic products, compositions and processes |
| US3135605A (en) * | 1962-02-15 | 1964-06-02 | Polaroid Corp | Novel photographic products, processes, and compositions employing novel anthraquinone dye developers |
| US3241963A (en) * | 1962-02-19 | 1966-03-22 | Polaroid Corp | Novel photographic products, processes and compositions |
| US3265505A (en) * | 1962-04-02 | 1966-08-09 | Eastman Kodak Co | Photographic products |
| US3077400A (en) * | 1962-04-26 | 1963-02-12 | Polaroid Corp | Color diffusion transfer using gelatinsilver halide emulsions containing cellulose ethers |
| US3287133A (en) * | 1963-03-01 | 1966-11-22 | Eastman Kodak Co | Photographic dye developer dispersions utilizing water-soluble sulfites |
| US3837852A (en) * | 1972-10-02 | 1974-09-24 | Gaf Corp | Color diffusion transfer process utilizing azo coupling to actuate diffusion of color providing species |
| JPS5421255B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1974-10-08 | 1979-07-28 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2543691A (en) * | 1946-06-07 | 1951-02-27 | Gen Aniline & Film Corp | Azo dyes as silver halide photographic developing agents |
| US2661293A (en) * | 1946-10-08 | 1953-12-01 | Polaroid Corp | Process of producing a colored photographic image by means of exhaustion of developer |
| US2559643A (en) * | 1948-02-19 | 1951-07-10 | Polaroid Corp | Photographic product and process |
| US2647649A (en) * | 1951-06-28 | 1953-08-04 | Onno L Maynard | Trash moving fork for tractors |
-
0
- DE DENDAT1066092D patent/DE1066092B/de active Pending
-
1955
- 1955-03-09 DE DEJ11460A patent/DE1172386B/de active Pending
- 1955-03-09 NL NL195421A patent/NL103503C/xx active
- 1955-03-09 GB GB2850557A patent/GB804974A/en not_active Expired
- 1955-03-09 CH CH358327D patent/CH358327A/de unknown
- 1955-03-09 GB GB690455A patent/GB804971A/en not_active Expired
- 1955-03-09 GB GB690555A patent/GB804972A/en not_active Expired
- 1955-03-09 CH CH580962A patent/CH404832A/de unknown
- 1955-03-09 CH CH580862A patent/CH386444A/de unknown
- 1955-03-09 DE DE19551419842 patent/DE1419842A1/de active Pending
- 1955-03-09 DE DEI9925A patent/DE1196075B/de active Pending
- 1955-03-09 DE DEI11459A patent/DE1035660B/de active Pending
- 1955-03-09 CH CH580662A patent/CH386245A/de unknown
- 1955-03-09 CH CH1709055A patent/CH363560A/de unknown
- 1955-03-09 GB GB3880457A patent/GB804976A/en not_active Expired
- 1955-03-09 GB GB2850657A patent/GB804975A/en not_active Expired
- 1955-03-09 CH CH580762A patent/CH391931A/de unknown
- 1955-03-09 NL NL195422A patent/NL103504C/xx active
- 1955-03-09 GB GB2850457A patent/GB804973A/en not_active Expired
- 1955-03-09 CH CH356356D patent/CH356356A/de unknown
-
1956
- 1956-12-29 FR FR1168292D patent/FR1168292A/fr not_active Expired
- 1956-12-29 FR FR1178429D patent/FR1178429A/fr not_active Expired
-
1957
- 1957-01-16 BE BE554213D patent/BE554213A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1419842A1 (de) | 1968-12-19 |
| GB804973A (en) | 1958-11-26 |
| CH391931A (de) | 1965-05-15 |
| CH356356A (de) | 1961-08-15 |
| GB804972A (en) | 1958-11-26 |
| DE1196075B (de) | 1965-07-01 |
| BE554213A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1957-07-16 |
| DE1035660B (de) | 1958-08-07 |
| CH363560A (de) | 1962-07-31 |
| GB804974A (en) | 1958-11-26 |
| GB804976A (en) | 1958-11-26 |
| CH386245A (de) | 1964-12-31 |
| FR1168292A (fr) | 1958-12-05 |
| NL195421A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1962-08-15 |
| NL103503C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1963-01-15 |
| CH404832A (de) | 1965-12-31 |
| CH358327A (de) | 1961-11-15 |
| GB804975A (en) | 1958-11-26 |
| GB804971A (en) | 1958-11-26 |
| CH386444A (de) | 1965-01-15 |
| NL103504C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1963-01-15 |
| NL195422A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1962-08-15 |
| FR1178429A (fr) | 1959-05-11 |
| DE1066092B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
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