US2196739A - Photographic developer for color photography - Google Patents
Photographic developer for color photography Download PDFInfo
- Publication number
- US2196739A US2196739A US231382A US23138238A US2196739A US 2196739 A US2196739 A US 2196739A US 231382 A US231382 A US 231382A US 23138238 A US23138238 A US 23138238A US 2196739 A US2196739 A US 2196739A
- Authority
- US
- United States
- Prior art keywords
- photographic
- amino
- tetrahydroquinoline
- developing
- developers
- 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
- 150000001875 compounds Chemical class 0.000 description 21
- 239000003795 chemical substances by application Substances 0.000 description 14
- LBUJPTNKIBCYBY-UHFFFAOYSA-N tetrahydroquinoline Natural products C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000000975 dye Substances 0.000 description 6
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical class NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- 239000004332 silver Substances 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- SSEWGJUYSOIDMK-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinolin-6-amine Chemical compound N1CCCC2=CC(N)=CC=C21 SSEWGJUYSOIDMK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- -1 cetyl compounds Chemical class 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 239000007822 coupling agent Substances 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical class CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- GTEKTBPHQPYBPS-UHFFFAOYSA-N 3-naphthalen-2-yl-3-oxopropanenitrile Chemical compound C1=CC=CC2=CC(C(CC#N)=O)=CC=C21 GTEKTBPHQPYBPS-UHFFFAOYSA-N 0.000 description 1
- DSQWWSVOIGUHAE-UHFFFAOYSA-N 4-chloro-2-phenylphenol Chemical compound OC1=CC=C(Cl)C=C1C1=CC=CC=C1 DSQWWSVOIGUHAE-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 239000005844 Thymol Substances 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical class NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000001046 green dye Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000009935 nitrosation Effects 0.000 description 1
- 238000007034 nitrosation reaction Methods 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 239000001048 orange dye Substances 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 150000004989 p-phenylenediamines Chemical class 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
- G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
- G03C7/407—Development processes or agents therefor
- G03C7/413—Developers
- G03C7/4136—Developers p-Phenylenediamine or derivatives thereof
Definitions
- This invention relates to photographic developers and particularly to a new class of developers containing heterocyclic ring systems and adapted for use in various processes of color photography.
- V In the processes of color photography in which a colored image is formed in a photographic layer by a color-forming development in which the development product of the photographic developer combines with a coupler compound, special types of developing agents must be used.
- the developing agents suitable for this purpose must contain a primary amino group and such developers are usually chosen from the classes of p-phenylene diamines and p-amino phenols or their various substitution products. described in the U. S. 1,l02,028,"June 30, 1914.
- Photographic dea (01. ss- -ss) in which R. represents the atoms necessary to complete a heterocyclic ring system, and X is an alkyl ⁇ : hydroxyalkyl, or an allyl group.
- R may be one of the following groups:
- a gelatino-silver halide emulsion layer after exposure, is developed in'a solution containing as the developing agents one of the compounds described above.
- the solution may contain in addition a coupler compound, or the coupler compound may be present in the sensitive layer prior to exposure.
- the layer may be developed to a colored negative image directly or may be developed first to a black and white negative by development in the ordinary way and then developed in the coupler developer to produce a positive colored image. The silver is then removed from the film leaving a pure dye image.
- a gelatino-silver halide emulsion layer was exposed behind a steptablet, developed in a metolhydroquinone developer, washed, exposed to white light, and then developed for ten minutes at 70 F. in the following developer solutioni Developer grams 1.5 Sodium sulfite do 2.0 Sodium carbonate do 50. Potassium bromide do 2. Coupler do 2. Sodium hydroxide do 1. Water to c.c 100 -U. S. Patent 1,969,479, the hydroxydiphenyls Of Mannes and,Godowsky U. S. Patent No. 2,039,730, the aceto-or cyano-acetamides of Mannes and Godowsky U. S. Patent No.
- thymol o-phenylphenol.
- the compounds described above may be used to produce a colored photographic image in a single photographic layer or may be used to produce a natural colored image in a multi-color layer or may be used for any of the dye images produced in a multi-layer film by coupler development.
- N(p-hydroxyethyl) 6-amino-1,2,3,4-tetrahydroquinoline and 1- (p-hydroxypropyl) -6-amino-phenmorpholine are made as follows:
- N (5-hydroxyethyl) 1,2,3,4 tetrahydroquinoline is prepared by the action of 1 part by weight of ethylene oxide upon 2 parts of 1,2,3,4-tetrahydroquinoline in a bomb (100-'160 C.) for four to nine hours.
- the resulting N(fi-hydroxyethyl)- 1,2,3,4-tetrahydroquinoline is purified by rectification and boils at 190-195 C./15 mm.
- the N(fl-hydroxyethyl) -6-amino-1,2,3,'4-tetrahydroquinoline is prepared by nitrosating the foregoing product by adding dropwise the calculated quantity of an aqueous solution of sodium nitrite to an excess of chilled-17% hydrochloric acid solution of the product.
- the resulting nitroso compound is reduced by the slow addition of zinc dust, the end of the reduction being determined by the decolorization of the solution.
- the zinc sludge is filtered, the filtrate made strongly basic and the amino derivative extracted with amyl alcohol.
- the i-(p-hydroxyethyl) -6-amino- 1,2,3,4-tetrahydroquinoline is obtained by rectification and boils at 208-215 D./4 mm.
- Phenmorpholine is readily prepared by the ac-' tion of ethylene-chlorohydrin on ortho-aminophenol according to the equations:
- a photographic developer comprising a com pound of the general formula.
- X is selected from the class consisting of alkyl, hydroxyalkyl, and allyl groups, and R represents the atoms necessary to complete-a heterocyclic ring.
- a photographic developer comprising a 6- amino- 1,2,3,4-tetrahydroquinoline having on the heterocyclic nitrogen atom a substituent selected from the class consisting of alkyl, hydroxyalkyl, and allyl groups.
- a photographic developing solution comprising a developing agent of the general formula l I I f' X l in which X is selected from the class consisting of alkyl, hydroxyalkyl, and allyl groups, and R represents the atoms necessary to complete a heterocyclic ring, and a coupling. compound which combines with the oxidation product of the developing agent on'photographic development to produce a colored image.
- a photographic developing solution comprising as a developing agent a 6-amino-1,2,3,4- tetrahydroquinoline having on the heterocyclic nitrogen atom a substituent selected from the class of alkyl, hydroxyalkyl, and allyl groups,
- a photographic developing solution comprising as a developing agent a 6-amino-l,2,3,4- tetrahydroquinoline having as allyl substituent on the heterocyclic nitrogen atom, and as a coupling agent, a compound which combines with 1 the oxidation product of the developing agent on photographic development to produce a colored image.
- the method of producing a colored photo-- graphic image in a gelatino-silver halide emulsion layer which comprises coupling the devel-' opment product of a B-amino-1,2,3,4-tetrahydroquinoline having on the heterocyclic nitrogen atom a substituent selected from the class consisting of alkyl, hydroxyalkyl, and allyl groups,
- the method of producing a colored photographic image in a gelatino-silver halide emulsion layer which comprises coupling the development product of a G-amino-l,2,3,4-tetrahydroquinoline having on the heterocyclic nitrogen atom a substituent selected from the class consisting of alkyl, hydroxyalkyl', and allylgroups,
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US231382A US2196739A (en) | 1938-09-23 | 1938-09-23 | Photographic developer for color photography |
| GB27972/38A GB519695A (en) | 1938-09-23 | 1938-09-26 | Improvements in colour photographic development |
| FR860363D FR860363A (fr) | 1938-09-23 | 1939-09-23 | Perfectionnements dans le développement photographique en couleurs |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US231382A US2196739A (en) | 1938-09-23 | 1938-09-23 | Photographic developer for color photography |
| GB27972/38A GB519695A (en) | 1938-09-23 | 1938-09-26 | Improvements in colour photographic development |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2196739A true US2196739A (en) | 1940-04-09 |
Family
ID=26259103
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US231382A Expired - Lifetime US2196739A (en) | 1938-09-23 | 1938-09-23 | Photographic developer for color photography |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US2196739A (fr) |
| FR (1) | FR860363A (fr) |
| GB (1) | GB519695A (fr) |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2417514A (en) * | 1940-09-23 | 1947-03-18 | Spectrum Products Company Inc | Method and means for producing colored photographic images |
| US2486440A (en) * | 1946-01-10 | 1949-11-01 | Gen Aniline & Film Corp | Production of phenazonium dyestuff images |
| US2550617A (en) * | 1946-06-06 | 1951-04-24 | Fr Corp | Fine grain photographic developer containing morpholine |
| US2566259A (en) * | 1948-09-25 | 1951-08-28 | Eastman Kodak Co | 8-alkyl sulfonamidoethyl-n-substituted saturated heterocyclic developers |
| US3630655A (en) * | 1967-11-06 | 1971-12-28 | Therachemie Chem Therapeut | Dyeing human hair with oxidation dyes comprising heterocyclic amino compounds |
| US3649160A (en) * | 1968-05-17 | 1972-03-14 | Oreal | Dyeing human hair with oxidation bases and an indoline coupler |
| US3970454A (en) * | 1974-01-10 | 1976-07-20 | Eastman Kodak Company | Photographic developing agents |
| US4066456A (en) * | 1974-12-10 | 1978-01-03 | Gaf Corporation | Incorporated carboxy substituted p-phenylenediamine color developer |
| US4066457A (en) * | 1974-12-10 | 1978-01-03 | Gaf Corporation | Color developer for diffusion transfer |
| EP0353531A1 (fr) * | 1988-07-25 | 1990-02-07 | Henkel Kommanditgesellschaft auf Aktien | Teinture capillaire |
| US5773203A (en) * | 1996-05-16 | 1998-06-30 | Fuji Photo Film Co., Ltd. | 4-(N,N-dialkylamino)aniline compounds, photographic processing composition containing the same and color image-forming method |
| US5962200A (en) * | 1994-02-25 | 1999-10-05 | Fuji Photo Film Co., Ltd. | Color developing agent, processing composition and color image-forming method |
| US5994546A (en) * | 1997-05-14 | 1999-11-30 | Fuji Photo Film Co., Ltd. | 4-(N,N-dialklylamino)aniline compounds, photographic processing composition containing the same and color image-forming method |
| US6005111A (en) * | 1994-02-25 | 1999-12-21 | Fuji Photo Film Co., Ltd. | Color developing agent, processing composition and color image-forming method |
| FR3024728A1 (fr) * | 2014-08-08 | 2016-02-12 | Oreal | Derives de benzoxazine et utilisation en coloration capillaire. |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2421693A (en) * | 1944-09-16 | 1947-06-03 | Gen Aniline & Film Corp | Imidazolone color formers |
| DE4206537A1 (de) * | 1992-03-02 | 1993-09-09 | Henkel Kgaa | Neue faerbemittel fuer fasern natuerlichen ursprungs und synthetische fasern |
-
1938
- 1938-09-23 US US231382A patent/US2196739A/en not_active Expired - Lifetime
- 1938-09-26 GB GB27972/38A patent/GB519695A/en not_active Expired
-
1939
- 1939-09-23 FR FR860363D patent/FR860363A/fr not_active Expired
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2417514A (en) * | 1940-09-23 | 1947-03-18 | Spectrum Products Company Inc | Method and means for producing colored photographic images |
| US2486440A (en) * | 1946-01-10 | 1949-11-01 | Gen Aniline & Film Corp | Production of phenazonium dyestuff images |
| US2550617A (en) * | 1946-06-06 | 1951-04-24 | Fr Corp | Fine grain photographic developer containing morpholine |
| US2566259A (en) * | 1948-09-25 | 1951-08-28 | Eastman Kodak Co | 8-alkyl sulfonamidoethyl-n-substituted saturated heterocyclic developers |
| US3630655A (en) * | 1967-11-06 | 1971-12-28 | Therachemie Chem Therapeut | Dyeing human hair with oxidation dyes comprising heterocyclic amino compounds |
| US3649160A (en) * | 1968-05-17 | 1972-03-14 | Oreal | Dyeing human hair with oxidation bases and an indoline coupler |
| US3970454A (en) * | 1974-01-10 | 1976-07-20 | Eastman Kodak Company | Photographic developing agents |
| US4066457A (en) * | 1974-12-10 | 1978-01-03 | Gaf Corporation | Color developer for diffusion transfer |
| US4066456A (en) * | 1974-12-10 | 1978-01-03 | Gaf Corporation | Incorporated carboxy substituted p-phenylenediamine color developer |
| EP0353531A1 (fr) * | 1988-07-25 | 1990-02-07 | Henkel Kommanditgesellschaft auf Aktien | Teinture capillaire |
| WO1990001050A1 (fr) * | 1988-07-25 | 1990-02-08 | Henkel Kommanditgesellschaft Auf Aktien | Teinture pour cheveux |
| US5089025A (en) * | 1988-07-25 | 1992-02-18 | Henkel Kommanditgesellschaft Auf Aktien | Hair dye compositions and certain 1,2,3,4-tetrahydronitroquinoxalines useful therein |
| JP2801716B2 (ja) | 1988-07-25 | 1998-09-21 | ヘンケル・コマンディットゲゼルシャフト・アウフ・アクチェン | 染髪製剤 |
| US5962200A (en) * | 1994-02-25 | 1999-10-05 | Fuji Photo Film Co., Ltd. | Color developing agent, processing composition and color image-forming method |
| US6005111A (en) * | 1994-02-25 | 1999-12-21 | Fuji Photo Film Co., Ltd. | Color developing agent, processing composition and color image-forming method |
| US5773203A (en) * | 1996-05-16 | 1998-06-30 | Fuji Photo Film Co., Ltd. | 4-(N,N-dialkylamino)aniline compounds, photographic processing composition containing the same and color image-forming method |
| US5994546A (en) * | 1997-05-14 | 1999-11-30 | Fuji Photo Film Co., Ltd. | 4-(N,N-dialklylamino)aniline compounds, photographic processing composition containing the same and color image-forming method |
| FR3024728A1 (fr) * | 2014-08-08 | 2016-02-12 | Oreal | Derives de benzoxazine et utilisation en coloration capillaire. |
Also Published As
| Publication number | Publication date |
|---|---|
| GB519695A (en) | 1940-04-03 |
| FR860363A (fr) | 1941-01-13 |
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