US2304953A - Photographic developer - Google Patents
Photographic developer Download PDFInfo
- Publication number
- US2304953A US2304953A US406025A US40602541A US2304953A US 2304953 A US2304953 A US 2304953A US 406025 A US406025 A US 406025A US 40602541 A US40602541 A US 40602541A US 2304953 A US2304953 A US 2304953A
- Authority
- US
- United States
- Prior art keywords
- photographic
- developing
- compounds
- image
- 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
- 239000003795 chemical substances by application Substances 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 6
- -1 tetrahydrofurfuryl Chemical group 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 230000003381 solubilizing effect Effects 0.000 description 4
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- AZFCIBBXCZMSTG-UHFFFAOYSA-N 3-[2-amino-5-(diethylamino)phenoxy]propan-1-ol Chemical compound CCN(CC)C1=CC=C(N)C(OCCCO)=C1 AZFCIBBXCZMSTG-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
- 230000002009 allergenic effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000004989 p-phenylenediamines Chemical class 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- YNAKESQZGPZDDZ-UHFFFAOYSA-N 2-n,2-n-diethylbenzene-1,2-diamine Chemical compound CCN(CC)C1=CC=CC=C1N YNAKESQZGPZDDZ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- GWBWGPRZOYDADH-UHFFFAOYSA-N [C].[Na] Chemical compound [C].[Na] GWBWGPRZOYDADH-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000012467 final product 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
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010265 sodium sulphite 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
- 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 more particularly to photographic developers in which a solubilizing group is attached to the aromatic ring system of the developer through an ether linkage.
- photographic developers of the p-phenylene diamine type are valuable compounds for producing fine grain black and white photographic images and also that these compounds, especially when they contain alkyl substituents, are useful as developers in the process for producing colored photographic images.
- the p-phenylenediamine developers have several defects.
- One disadvantage of these developers is that they are'not highly soluble in the developing solutions.
- Another disadvantage is that they are highly allergenic, that is, they are poisonous to the human skin and are, therefore, somewhat dangerous to use.
- the p-phenylenediamines are used in the color development process, it has also been found that they do not always produce the desired color in the final image.
- the principal object of my pres-- ent invention to provide a new class of photographic developing agents of the p-phenylenediamine type.
- a further object is to provide photographic developing agents which are more soluble in the developing solutions than compounds previously used.
- a still further object is to provide developing agents which are less allergenic, that is, less poisonousto the human skin than compounds hitherto known.
- a still further object is to provide photographic developing agents of the substituted p-phenylenediamine type which are useful in photographic color processes for the purpose of producing images of the desired color.
- R1 and R2 are alkyl radicals, heterocyclic substituted alkyl radicals such as tetrahydrofurfuryl, or' aryl substituted alkyl radicals such as benzyl, or R1 and R2 together represent the atoms necessary to conetmplate a hetero-- cyclic system, and R3 represents an alkylene radical having attached thereto a water solubilizing group such as hydroxyl, carboxyl, sulfonic acid, amino or acid amide.
- Compound 3 was prepared by a similar procedure starting with 3-( s-hydroxyethoxy) diethylaniline. It boiled at 156-160 C. at two millimeters pressure.
- These compounds may be further substituted in the aromatic ring with other groups including halide, amino, substituted amino, azo, alkyl and aryl groups. These groups have a tendency to alter the color of the final dye image and the color of the image may be controlled in this way.
- the developers of my invention may be used in conjunction with any well knowncoupler compounds such as those described in Fischer U. S. Patent- 1,102,028, June 30, 1914; Mannes and Godowsky U. S. Patent 2,108,602, February15, 1938; Mannes, Godowsky and Peterson U. S. Patent 2,115,394, April 26, 1938; and 4 Mannes, Godowsky and Peterson U. S. Patent 2,125,337, August 9, 1938.
- Example 1 3-( -hydroxyl propoxy)-4-amino diethylaniline grams 2 Sodium sulphitedo Sodium carbonate do 30 Water in .1000
- the coupler used to form a colored image may be incorporated in the emulsion-layer prior to exposure and a colored image formed by development in the following solution:
- the developing agents described in the present application may be used to form photographic images by development of exposed silver halide contained in the usual gelatin carrier or in carriers such as collodion, water permeable cellulose esters, or water permeable synthetic resins.
- the sensitive layers may be carried on any suitable support such as glass, paper, cellulose esters I or synthetic resins. They may be used with multi-layer films where two or more layers are coated on the same side of a support or where the layers are coated on the opposite sides of a support.
- a photographic developing agent having the following general formula:
- R1 and R2 are substituents selected from the group consisting of alkyl, heterocyclic substituted alkyl, aryl substituted alkyl, and the atoms necessary to complete a heterocyclic system;
- Ra an alkylene radical having attached thereto a hydroxyl solubilizing group.
- a photographic developing agent comprising 3- (y-hydroxypropoxy) -4 -aminodiethylaniline.
- a photographic developing agent comprising 3- (p-hydroxyethoxy) -4-aminodiethylaniline.
- a photographic developing solution for producing a colored image comprising 3-( -hydroxypropoxy) -4-aminodiethylaniline as the developing agent, and a compound which couples with the developing agent on photographic development to form a colored image.
- a photographic developing solution for producing a colored image comprising Z-(p-hydroxyethoxy). -4-aminodiethylaniline.
- R1 wherein R1 and R2 are substituents selected from 7 10 the group consisting of alkyl, heterocyclic substituted alkyl, aryl substituted alkyl, and the atoms necessary to complete a heterocyclic system;
- Ra an alkylene radical having attached thereto a water solubilizing group; in the .presence of a phenolic coupler compound.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR956696D FR956696A (en, 2012) | 1941-08-08 | ||
| US406025A US2304953A (en) | 1941-08-08 | 1941-08-08 | Photographic developer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US406025A US2304953A (en) | 1941-08-08 | 1941-08-08 | Photographic developer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2304953A true US2304953A (en) | 1942-12-15 |
Family
ID=23606235
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US406025A Expired - Lifetime US2304953A (en) | 1941-08-08 | 1941-08-08 | Photographic developer |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US2304953A (en, 2012) |
| FR (1) | FR956696A (en, 2012) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2486440A (en) * | 1946-01-10 | 1949-11-01 | Gen Aniline & Film Corp | Production of phenazonium dyestuff images |
| US2548574A (en) * | 1947-02-27 | 1951-04-10 | Eastman Kodak Co | Sulfonamide substituted p-phenylenediamines containing o-alkoxy groups as silver halide photographic developers |
| US2552242A (en) * | 1948-03-06 | 1951-05-08 | Eastman Kodak Co | p-phenylenediamines containing n-alkylacetamido ethyl substituent |
| US2552241A (en) * | 1947-05-23 | 1951-05-08 | Eastman Kodak Co | p-phenylenediamines containing alkylacylamidoethyl or alkylacylamidoethoxy ring substituents |
| US2592364A (en) * | 1947-05-23 | 1952-04-08 | Eastman Kodak Co | p-phenylenediamine developer containing alkylacylamidoethyl or alkylacylamidoethoxyring substituents |
| US2604399A (en) * | 1949-07-07 | 1952-07-22 | Eastman Kodak Co | Photographic developers comprising bis-(di-hydroxyalkyl aminomethyl)-hydroquinones |
| US3656950A (en) * | 1970-12-03 | 1972-04-18 | Eastman Kodak Co | Color photographic processes |
| US3658525A (en) * | 1970-12-03 | 1972-04-25 | Eastman Kodak Co | Reversal color photographic processes |
| US4137080A (en) * | 1975-11-07 | 1979-01-30 | Konishiroku Photo Industry Co., Ltd. | Process for dye image production on a light-sensitive silver halide photographic material |
| US5614356A (en) * | 1994-06-08 | 1997-03-25 | Fuji Photo Film Co., Ltd. | Color developing agent, processing composition and color image-forming method |
| US5721093A (en) * | 1995-03-15 | 1998-02-24 | Fuji Photo Film Co., Ltd. | Color developing agent, processing composition and color image-forming method |
-
0
- FR FR956696D patent/FR956696A/fr not_active Expired
-
1941
- 1941-08-08 US US406025A patent/US2304953A/en not_active Expired - Lifetime
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2570116A (en) * | 1946-01-10 | 1951-10-02 | Gen Aniline & Film Corp | Color developers for the production of azine dye images |
| US2486440A (en) * | 1946-01-10 | 1949-11-01 | Gen Aniline & Film Corp | Production of phenazonium dyestuff images |
| US2548574A (en) * | 1947-02-27 | 1951-04-10 | Eastman Kodak Co | Sulfonamide substituted p-phenylenediamines containing o-alkoxy groups as silver halide photographic developers |
| US2552240A (en) * | 1947-02-27 | 1951-05-08 | Eastman Kodak Co | N-beta-methylsulfonamidoethyl-p-phenylenediamines |
| US2592364A (en) * | 1947-05-23 | 1952-04-08 | Eastman Kodak Co | p-phenylenediamine developer containing alkylacylamidoethyl or alkylacylamidoethoxyring substituents |
| US2552241A (en) * | 1947-05-23 | 1951-05-08 | Eastman Kodak Co | p-phenylenediamines containing alkylacylamidoethyl or alkylacylamidoethoxy ring substituents |
| US2552242A (en) * | 1948-03-06 | 1951-05-08 | Eastman Kodak Co | p-phenylenediamines containing n-alkylacetamido ethyl substituent |
| US2604399A (en) * | 1949-07-07 | 1952-07-22 | Eastman Kodak Co | Photographic developers comprising bis-(di-hydroxyalkyl aminomethyl)-hydroquinones |
| US3656950A (en) * | 1970-12-03 | 1972-04-18 | Eastman Kodak Co | Color photographic processes |
| US3658525A (en) * | 1970-12-03 | 1972-04-25 | Eastman Kodak Co | Reversal color photographic processes |
| JPS5121582B1 (en, 2012) * | 1970-12-03 | 1976-07-03 | ||
| US4137080A (en) * | 1975-11-07 | 1979-01-30 | Konishiroku Photo Industry Co., Ltd. | Process for dye image production on a light-sensitive silver halide photographic material |
| US5614356A (en) * | 1994-06-08 | 1997-03-25 | Fuji Photo Film Co., Ltd. | Color developing agent, processing composition and color image-forming method |
| US5721093A (en) * | 1995-03-15 | 1998-02-24 | Fuji Photo Film Co., Ltd. | Color developing agent, processing composition and color image-forming method |
Also Published As
| Publication number | Publication date |
|---|---|
| FR956696A (en, 2012) | 1950-02-02 |
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