US2449919A - 3-methylsulfonamido-4-amino dimethyl aniline photographic developer - Google Patents
3-methylsulfonamido-4-amino dimethyl aniline photographic developer Download PDFInfo
- Publication number
- US2449919A US2449919A US759302A US75930247A US2449919A US 2449919 A US2449919 A US 2449919A US 759302 A US759302 A US 759302A US 75930247 A US75930247 A US 75930247A US 2449919 A US2449919 A US 2449919A
- Authority
- US
- United States
- Prior art keywords
- methylsulfonamido
- photographic
- amino
- dimethyl aniline
- photographic developer
- 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
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- DEZPIHNXRYWXQK-UHFFFAOYSA-N n-[2-amino-5-(dimethylamino)phenyl]methanesulfonamide Chemical compound CN(C)C1=CC=C(N)C(NS(C)(=O)=O)=C1 DEZPIHNXRYWXQK-UHFFFAOYSA-N 0.000 title description 2
- 239000003795 chemical substances by application Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- -1 methylsulfonamido Chemical group 0.000 description 5
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-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
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 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
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 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
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin 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
- 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 de- CH velopers and more particularly to photographic developers for color photography.
- Developing agents of the p-phenylene diamine type having a lower fatty acid acyl amino group such as an acetylamino group on the phenylene ring are described in Hanson U. S. Patent 2,350,109, granted May 30, 1944. While these developing agents are suitable for producing colored images by coupling with color-forming compounds, they are of rather low solubility in the developing solution.
- a further object is to provide developing agents of the p-phenylene diamine type which are of suflicient solubility in the developing solution to enable the production of dye images upon color development, having the required density.
- Developing agents which may be used according to my invention are 3-methy1sulfonam1do-4- amino-dimethylaniline, 3-methylsulfonamido-4- 'amino-diethylaniline, etc.
- a typical compound, 3 methylsulfonamido-4-amino-dimethylaniline has the following structure:
- the corresponding diethyl compound may be prepared by treating the diethylaminonitroso compound in a similar manner.
- the developers of my invention may be used in conjunction with any well-known coupler compounds such as those described in Fischer U. 8. Patent 1,102,028, granted June 30, 1914, Mannes and Godowsky U. 8. Patent 2,108,602, granted February 15, 1938, or Mannes,
- the developers of my invention produce magneta to red dyes with phenolic hydroxyl coupiers, such as 2,4-dichloro-a-naphthol. These dyes are of the azine class.
- the following example illustrates a developing solution which may be used according to my invention 3 methylsulfonamido 4-amino-dimethylaniline "grams" 1 Sodium suliite do 0.5 Sodium carbonate do 20 Potassium bromide do 1 Water to 1 liter (1:) Coupler (2,4-dichloro-a-naphtho1) --do 2 Sodium hydroxide (10% solution) cc 10 For use, b is added to a.
- 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 coll-odion, water-permeable cellulose ester or water-permeable synthetic resins.
- a developing solution for producing a colored photographic image comprising 3-methylsulfonamido-4-amino-dimethyl aniline and a compound which couples with the development of said developing agent to form a colored image upon photographic development.
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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Description
Patented Sept. 21 1948 2,449,919 I v3-METHYLsunrolvniun'io-4-AMmo m 'ME'mYn'ANmmn PHOTOGRAPHIC DEVELOPER Arnold Weissberger, Rochester, N. -Y.,,assignor to vj.
Eastman Kodak Company, Rochester, N.; Y.,. a 1
corporation of New Jersey No Drawing. Application July 5, 194
Serial No. 759,302 2 Claims. (01. 95-88) 2 This invention relates to photographic de- CH velopers and more particularly to photographic developers for color photography.
It is known that photographic developers of H: on. the p-phenylene diamine type are valuable Oil;- 5 2Hr-' pounds for producing fine grain black-and-w e photographic images and also that these compounds, especially when they contain alkyl sub- N0 NHI stituents on one of the nitrogen atoms are useful m as developers in producing colored photographic The troso compound (7 ms) was susimages.
Developing agents of the p-phenylene diamine type having a lower fatty acid acyl amino group such as an acetylamino group on the phenylene ring are described in Hanson U. S. Patent 2,350,109, granted May 30, 1944. While these developing agents are suitable for producing colored images by coupling with color-forming compounds, they are of rather low solubility in the developing solution.
It is therefore an object of the present invention to provide a new class of photographic developing agents of the p-phenylene diamine type. A further object is to provide developing agents of the p-phenylene diamine type which are of suflicient solubility in the developing solution to enable the production of dye images upon color development, having the required density.
These objects are accomplished by the present invention by the use as developing agents of 3 methylsulfonamido i-amino-dialkylaniline compounds.
Developing agents which may be used according to my invention are 3-methy1sulfonam1do-4- amino-dimethylaniline, 3-methylsulfonamido-4- 'amino-diethylaniline, etc. A typical compound, 3 methylsulfonamido-4-amino-dimethylaniline has the following structure:
C HI
NHSOlC HI This compound was prepared by reduction of the nitroso compound according to the following reaction:
pended in alcohol and reduced with Raney nickel catalyst and hydrogen at room temperature. The filtered solution was treated with 2.8 grams of sulfuric acid in 2 cc. of water, stirred and cooled in ice. The crystalline sulfate was filtered from the deep purple solution, washed with alcohol, ether and dried. The yield was 5.5 grains (69%). It was a grayish powder, readily soluble in water.
The corresponding diethyl compound may be prepared by treating the diethylaminonitroso compound in a similar manner.
When used for the formation of colored photographic images, the developers of my invention may be used in conjunction with any well-known coupler compounds such as those described in Fischer U. 8. Patent 1,102,028, granted June 30, 1914, Mannes and Godowsky U. 8. Patent 2,108,602, granted February 15, 1938, or Mannes,
'Godowsky and Peterson U. S. Patent 2,115,394,
granted April 26, 1938, and 2,126,337, granted August 9, 1938.v
The developers of my invention produce magneta to red dyes with phenolic hydroxyl coupiers, such as 2,4-dichloro-a-naphthol. These dyes are of the azine class.
The following example illustrates a developing solution which may be used according to my invention 3 methylsulfonamido 4-amino-dimethylaniline "grams" 1 Sodium suliite do 0.5 Sodium carbonate do 20 Potassium bromide do 1 Water to 1 liter (1:) Coupler (2,4-dichloro-a-naphtho1) --do 2 Sodium hydroxide (10% solution) cc 10 For use, b is added to a.
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 coll-odion, water-permeable cellulose ester or water-permeable synthetic resins. My developing agents may be used with photographic films containing the coupler in the emulsion layer as described in Mannes and Godowsky 'U.:.'"S .1Patent 2,304;94 0, granted December=15, .,1*942,1or .Jelley andWittum-KLUJ S." Batent 2,322,027, granted June 15, 1943.
It will be understood that the examples in-- 1. A photographic developing *solution com prising as the developing agent ii-methylsulfonamido-4-amino-dimethy1 aniline.
Tile of "this patent:
2. A developing solution for producing a colored photographic image comprising 3-methylsulfonamido-4-amino-dimethyl aniline and a compound which couples with the development of said developing agent to form a colored image upon photographic development.
ARNOLD WEISSBERGER.
REFERENCES CITED The followingi'referencesare of record in the UNITED STATES PATENTS
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US759302A US2449919A (en) | 1947-07-05 | 1947-07-05 | 3-methylsulfonamido-4-amino dimethyl aniline photographic developer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US759302A US2449919A (en) | 1947-07-05 | 1947-07-05 | 3-methylsulfonamido-4-amino dimethyl aniline photographic developer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2449919A true US2449919A (en) | 1948-09-21 |
Family
ID=25055151
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US759302A Expired - Lifetime US2449919A (en) | 1947-07-05 | 1947-07-05 | 3-methylsulfonamido-4-amino dimethyl aniline photographic developer |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2449919A (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2527379A (en) * | 1948-07-15 | 1950-10-24 | Gen Aniline & Film Corp | Silver halide developers for the production of azine dyestuff images |
| US2537460A (en) * | 1948-07-15 | 1951-01-09 | Gen Aniline & Film Corp | Production of azine dye images by means of a developer containing two n-substituted-diamino-meta-nilic acids |
| US2592364A (en) * | 1947-05-23 | 1952-04-08 | Eastman Kodak Co | p-phenylenediamine developer containing alkylacylamidoethyl or alkylacylamidoethoxyring substituents |
| 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 |
| EP0370348A1 (en) * | 1988-11-24 | 1990-05-30 | Agfa-Gevaert AG | Photographic-reversal method |
| EP0433812A1 (en) * | 1989-12-21 | 1991-06-26 | Agfa-Gevaert AG | Method for colour developing |
| EP0370351A3 (en) * | 1988-11-24 | 1991-09-18 | Agfa-Gevaert AG | Photographic reversal process |
| EP0364845A3 (en) * | 1988-10-20 | 1991-09-25 | Agfa-Gevaert AG | Photographic-reversal process |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2163166A (en) * | 1936-05-27 | 1939-06-20 | Agfa Ansco Corp | Photographic developer |
| US2350109A (en) * | 1941-09-11 | 1944-05-30 | Eastman Kodak Co | Photographic developers containing acylamino groups |
| US2414491A (en) * | 1945-01-27 | 1947-01-21 | Gen Aniline & Film Corp | Photographic developer |
-
1947
- 1947-07-05 US US759302A patent/US2449919A/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2163166A (en) * | 1936-05-27 | 1939-06-20 | Agfa Ansco Corp | Photographic developer |
| US2350109A (en) * | 1941-09-11 | 1944-05-30 | Eastman Kodak Co | Photographic developers containing acylamino groups |
| US2414491A (en) * | 1945-01-27 | 1947-01-21 | Gen Aniline & Film Corp | Photographic developer |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2592364A (en) * | 1947-05-23 | 1952-04-08 | Eastman Kodak Co | p-phenylenediamine developer containing alkylacylamidoethyl or alkylacylamidoethoxyring substituents |
| US2592363A (en) * | 1947-05-23 | 1952-04-08 | Eastman Kodak Co | P-phenylenediamine developer containing nu-alkylacetamido ethyl substituent |
| US2527379A (en) * | 1948-07-15 | 1950-10-24 | Gen Aniline & Film Corp | Silver halide developers for the production of azine dyestuff images |
| US2537460A (en) * | 1948-07-15 | 1951-01-09 | Gen Aniline & Film Corp | Production of azine dye images by means of a developer containing two n-substituted-diamino-meta-nilic acids |
| US2594917A (en) * | 1949-12-16 | 1952-04-29 | Gen Aniline & Film Corp | Suppression of proximity development with azine color developers |
| EP0364845A3 (en) * | 1988-10-20 | 1991-09-25 | Agfa-Gevaert AG | Photographic-reversal process |
| EP0370348A1 (en) * | 1988-11-24 | 1990-05-30 | Agfa-Gevaert AG | Photographic-reversal method |
| EP0370351A3 (en) * | 1988-11-24 | 1991-09-18 | Agfa-Gevaert AG | Photographic reversal process |
| EP0433812A1 (en) * | 1989-12-21 | 1991-06-26 | Agfa-Gevaert AG | Method for colour developing |
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