US2350109A - Photographic developers containing acylamino groups - Google Patents
Photographic developers containing acylamino groups Download PDFInfo
- Publication number
- US2350109A US2350109A US410422A US41042241A US2350109A US 2350109 A US2350109 A US 2350109A US 410422 A US410422 A US 410422A US 41042241 A US41042241 A US 41042241A US 2350109 A US2350109 A US 2350109A
- Authority
- US
- United States
- Prior art keywords
- photographic
- acylamino groups
- developers containing
- photographic developers
- developing agent
- 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
- 125000004442 acylamino group Chemical group 0.000 title description 3
- 239000003795 chemical substances by application Substances 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 10
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- -1 propionylamino groups Chemical group 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- 125000003118 aryl group Chemical group 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- PEIVHTCIMKJVJF-UHFFFAOYSA-N n-[2-amino-5-(dimethylamino)phenyl]acetamide Chemical compound CN(C)C1=CC=C(N)C(NC(C)=O)=C1 PEIVHTCIMKJVJF-UHFFFAOYSA-N 0.000 description 2
- 150000004989 p-phenylenediamines Chemical class 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- 230000007096 poisonous effect 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
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- QNGVNLMMEQUVQK-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C=C1 QNGVNLMMEQUVQK-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- BZORFPDSXLZWJF-UHFFFAOYSA-N N,N-dimethyl-1,4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000000397 acetylating effect Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000000839 emulsion 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
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- CJDICMLSLYHRPT-UHFFFAOYSA-N n,n-dimethyl-3-nitroaniline Chemical compound CN(C)C1=CC=CC([N+]([O-])=O)=C1 CJDICMLSLYHRPT-UHFFFAOYSA-N 0.000 description 1
- HXOYSVJNHDLHIE-UHFFFAOYSA-N n-[2-(dimethylamino)phenyl]acetamide Chemical compound CN(C)C1=CC=CC=C1NC(C)=O HXOYSVJNHDLHIE-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 239000000123 paper 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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 p-phenylenediamine developers containing acylaminogroups.
- photographic developers of 'the p-phenylenediamine type are valuable com-, pounds for producing fine grain black and white photographic images and also that these compounds, especially when they contain alkyl substituents on one of the nitrogen atoms, are useful as developers in producing colored photo-
- a serious disadvantage of the p-phenylenediamine developers is that they are highly allergenic, that is, are poisonous to the human skin and, therefore, are somewhat dangerous to use.
- the p-phenylenedia'mines are used in color development processes, it has also been found that they do not always produce the desired color in the final image.
- the principal object of the present 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 less allergenic, that is, less poisonous to the human skin, than the p-phenylenediamines.
- 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.
- Dialkyl-p-phenylenediamines having acylamino substituents such as acetylamino or propionylamino groups on the ring are suitablefor introduction of the acylamino group.
- One of the specific compounds which I have found suitable for use'according to our invention is 3-acetylamino-4-aminodimethylaniline. This compound is prepared by reducing m-nitrodimethylaniline to the amine and acetylating it with acetic anhydride and glacial acetic acid.
- the acetylaminodimethylaniline is nitrosated by treatment with sodium nitrite in 2-N-hydrochloric 'acid and the nitroso derivative reduced at room temperature with hydrogen by using a Raney nickel catalyst.
- the compounds which I propose to use may be further substituted in the aromatic ring with other groups including halide, amino, substituted amino, azo, alkyl and aryl groups. These groups Peterson U. S. Patents tend to alter the color of the color of way.
- the developers of my invention may be used in conjunction with any well known coupler compounds such as those described in Fischer U. S. Patent 1,102,028, granted June 30, 1914; Mannes 8r Godowsky U. S. Patent 2,108,602. granted February 15, 1938; Mannes, Godowsky 8: 2,115,394, granted April 26, 1938 and 2,126,337, granted August 9, 1938.
- the developing agents described in the present application may be used to form photographic images by development of exposed silver halide contained inthe usual gelatin carrier or rip 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 ester or synthetic resins. They may be used with multi-layer films where two or more layers are coated on the same side ofa support or where the layers are coated on the opposite sides of a support.
- a photographic developing solution comprising as the developing agent a lower fatty acid acylamino-4-aminodialkylaniline.
- a photographic developing solution comprising as the developing agent a 4-aminodialkylaniline having a lower fatty acid acylamino group in the 3-position.
- a photographic developing solution comprising as the developing agent a 3-acetylamino- 4-aminodialkylaniline.
- a photographic developing solution comprising the final dye image and ing as the developing agent 3-acetylemino-4- aminodimethylaniline.
- a photographic developing solution for producing a, colored image comprising a lower fatty acid acylamino-4-aminodialkylaniline 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 3-aqetvlamino-4-aminodimethylaniline as the developing agent and a compound which couples with the developing agent on photographic development to form a colored image.
- the method of producing a colored photonewton graphic e in e geletino silver lide emulsion layer which comprises coupling the development product of a. lower fatty cold ncyl 4-eminodialkyleniline developing agent with a compound which couples with the developing agent on development.
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 |
|---|---|---|---|
| FR956698D FR956698A (enrdf_load_stackoverflow) | 1941-09-11 | ||
| US410422A US2350109A (en) | 1941-09-11 | 1941-09-11 | Photographic developers containing acylamino groups |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US410422A US2350109A (en) | 1941-09-11 | 1941-09-11 | Photographic developers containing acylamino groups |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2350109A true US2350109A (en) | 1944-05-30 |
Family
ID=23624655
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US410422A Expired - Lifetime US2350109A (en) | 1941-09-11 | 1941-09-11 | Photographic developers containing acylamino groups |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US2350109A (enrdf_load_stackoverflow) |
| FR (1) | FR956698A (enrdf_load_stackoverflow) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2449919A (en) * | 1947-07-05 | 1948-09-21 | Eastman Kodak Co | 3-methylsulfonamido-4-amino dimethyl aniline photographic developer |
| US2478400A (en) * | 1945-08-17 | 1949-08-09 | Eastman Kodak Co | Silver halide photographic emulsion with developer and color coupler dispersed therein |
| US2486440A (en) * | 1946-01-10 | 1949-11-01 | Gen Aniline & Film Corp | Production of phenazonium dyestuff images |
| US2592363A (en) * | 1947-05-23 | 1952-04-08 | Eastman Kodak Co | P-phenylenediamine developer containing nu-alkylacetamido ethyl substituent |
| US2594917A (en) * | 1949-12-16 | 1952-04-29 | Gen Aniline & Film Corp | Suppression of proximity development with azine color developers |
-
0
- FR FR956698D patent/FR956698A/fr not_active Expired
-
1941
- 1941-09-11 US US410422A patent/US2350109A/en not_active Expired - Lifetime
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2478400A (en) * | 1945-08-17 | 1949-08-09 | Eastman Kodak Co | Silver halide photographic emulsion with developer and color coupler dispersed therein |
| US2486440A (en) * | 1946-01-10 | 1949-11-01 | Gen Aniline & Film Corp | Production of phenazonium dyestuff images |
| US2592363A (en) * | 1947-05-23 | 1952-04-08 | Eastman Kodak Co | P-phenylenediamine developer containing nu-alkylacetamido ethyl substituent |
| US2449919A (en) * | 1947-07-05 | 1948-09-21 | Eastman Kodak Co | 3-methylsulfonamido-4-amino dimethyl aniline photographic developer |
| US2594917A (en) * | 1949-12-16 | 1952-04-29 | Gen Aniline & Film Corp | Suppression of proximity development with azine color developers |
Also Published As
| Publication number | Publication date |
|---|---|
| FR956698A (enrdf_load_stackoverflow) | 1950-02-02 |
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