GB807899A - New photographic developers - Google Patents
New photographic developersInfo
- Publication number
- GB807899A GB807899A GB1793656A GB1793656A GB807899A GB 807899 A GB807899 A GB 807899A GB 1793656 A GB1793656 A GB 1793656A GB 1793656 A GB1793656 A GB 1793656A GB 807899 A GB807899 A GB 807899A
- Authority
- GB
- United Kingdom
- Prior art keywords
- aniline
- ethyl
- amino
- methyl
- disubstituted
- 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
Links
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
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises compounds of the general formula <FORM:0807899/IV (b)/1> where R is C1-C4 alkyl or hydroxyalkyl, R1 is C1-C6 alkyl substituted in the omega position by an hydroxyl group, X is hydrogen or C1-C4 alkyl or alkoxy group, and n = 0 or 1, R may be e.g. methyl, ethyl, propyl, butyl, or the corresponding hydroxy radical, R1 may be hydroxymethyl, beta-hydroxyethyl, or delta hydroxybutyl, X may be e.g. methyl, methoxy, ethoxy or butoxy. The compounds of the invention may be prepared by reducing the corresponding 4 - nitroso - N:N - disubstituted aniline or 4-nitroso - N:N - disubstituted 3 - substituted aniline which in turn may be prepared by the action of nitrous acid on the corresponding N:N-disubstituted aniline or N:N-disubstituted 3-substituted aniline. The N:N-disubstituted aniline or N:N-disubstituted 3-substituted aniline is prepared from the corresponding 3-substituted aniline or aniline itself and the corresponding o -bromoalkyl acetate, or in the case of N-ethyl-N-(omega hydroxyhexy)-m-toluidine, from 6-bromohexan-1-ol and N-ethyl-m-toludine. The compounds of the invention may be isolated in the form of their salts, e.g. with sulphuric or naphthalene 1:5 disulphonic acid, or in the form of their substituted anils, e.g. by condensing with benzaldehyde-2-carboxylic acid, or 4-chlorobenzaldehyde-2-sulphonic acid and isolating the sodium salts therefrom. The invention further comprises a composition of the compounds of the invention in an aqueous alkaline solution. Examples are given of the preparation of the following compounds and their corresponding substituted aniline starting materials: (1) 4-amino-3-methyl - N - ethyl - N - (gamma - hydroxypropyl) aniline and the sodium salt of 3-methyl-4-(41-chloro - 21 - sulphobenzylidene - amino) - N-ethyl-N-(gamma-hydroxypropyl) aniline, and of the starting materials, viz. N-ethyl-N-(gamma-hydroxypropyl) m-toluidine and the corresponding nitroso compound; (2) 4-amino-3-methyl-N - ethyl - N - (delta - hydroxybutyl) aniline and the sodium salt of 3-methyl-4-(41-chloro-21-sulphobenzylideneamino) - N - ethyl - N - (delta-hydroxybutyl) aniline; (3) 4-amino-3-methyl-N-ethyl N-(omega-hydroxyl-hexyl) aniline and the corresponding sodium salt of its anil with 4-chlorobenzaldehyde-2-sulphonic acid; (4) 4-amino - 3 - methyl - N1N1 - di - (delta - hydroxybutyl) aniline; (5) 4 - amino - N1N1 - di-(gamma - hydroxypropyl) aniline; (6) 4-amino - N:N - di - (delta - hydroxybutyl) aniline; (7) 4 - amino - N:N - di - (epsilon-hydroxypentyl) aniline; (8) 4 - amino - 3-methoxy - N:N - di - (epsilon - hydroxypentyl) aniline. The preparation of the 1:5 naphthalenedisulphonate of the latter five compounds is also described. The epsilon-bromopentyl acetate used in the preparation of compound (7) above is prepared by reacting acetyl bromide and tetrahydropyran in the presence of anhydrous zinc chloride.
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BE558251D BE558251A (en) | 1956-06-11 | ||
GB1793656A GB807899A (en) | 1956-06-11 | 1956-06-11 | New photographic developers |
FR1176645D FR1176645A (en) | 1956-06-11 | 1957-06-11 | New photographic developers |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1793656A GB807899A (en) | 1956-06-11 | 1956-06-11 | New photographic developers |
Publications (1)
Publication Number | Publication Date |
---|---|
GB807899A true GB807899A (en) | 1959-01-21 |
Family
ID=10103844
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1793656A Expired GB807899A (en) | 1956-06-11 | 1956-06-11 | New photographic developers |
Country Status (3)
Country | Link |
---|---|
BE (1) | BE558251A (en) |
FR (1) | FR1176645A (en) |
GB (1) | GB807899A (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5380625A (en) * | 1992-02-05 | 1995-01-10 | Fuji Photo Film Co., Ltd. | Method for processing silver halide color photographic materials comprising particular dye couplers using particular developers |
US5478704A (en) * | 1991-11-22 | 1995-12-26 | Fuji Photo Film Co., Ltd. | Method for forming color images |
WO2004105765A1 (en) * | 2003-05-27 | 2004-12-09 | Janssen Pharmaceutica N.V. | Macrocyclic quinazoline derivatives as antiproliferative agents |
US8318731B2 (en) | 2007-07-27 | 2012-11-27 | Janssen Pharmaceutica Nv | Pyrrolopyrimidines |
US8492377B2 (en) | 2006-07-13 | 2013-07-23 | Janssen Pharmaceutica Nv | MTKI quinazoline derivatives |
US8772272B2 (en) | 2003-12-18 | 2014-07-08 | Janssen Pharmaceutica Nv | Pyrido-and pyrimidopyrimidine derivatives as anti-proliferative agents |
US9688691B2 (en) | 2004-12-08 | 2017-06-27 | Janssen Pharmaceutica Nv | Macrocyclic quinazole derivatives and their use as MTKI |
-
0
- BE BE558251D patent/BE558251A/xx unknown
-
1956
- 1956-06-11 GB GB1793656A patent/GB807899A/en not_active Expired
-
1957
- 1957-06-11 FR FR1176645D patent/FR1176645A/en not_active Expired
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5478704A (en) * | 1991-11-22 | 1995-12-26 | Fuji Photo Film Co., Ltd. | Method for forming color images |
US5380625A (en) * | 1992-02-05 | 1995-01-10 | Fuji Photo Film Co., Ltd. | Method for processing silver halide color photographic materials comprising particular dye couplers using particular developers |
KR101143878B1 (en) * | 2003-05-27 | 2012-05-24 | 얀센 파마슈티카 엔.브이. | Macrocyclic quinazoline derivatives as antiproliferative agents |
EA009064B1 (en) * | 2003-05-27 | 2007-10-26 | Янссен Фармацевтика Н. В. | Macrocyclic quinazoline derivatives as antiproliferative agents |
US7648975B2 (en) | 2003-05-27 | 2010-01-19 | Janssen Pharmaceutica N.V. | Macrocyclic quinazoline derivatives as antiproliferative agents |
EP2305687A1 (en) * | 2003-05-27 | 2011-04-06 | Janssen Pharmaceutica NV | Quinazoline derivatives |
WO2004105765A1 (en) * | 2003-05-27 | 2004-12-09 | Janssen Pharmaceutica N.V. | Macrocyclic quinazoline derivatives as antiproliferative agents |
US8394786B2 (en) | 2003-05-27 | 2013-03-12 | Janssen Pharmaceutica N.V. | Quinazoline derivatives |
US9273013B2 (en) | 2003-05-27 | 2016-03-01 | Janssen Pharmaceutica Nv | Quinazoline derivatives |
US8772272B2 (en) | 2003-12-18 | 2014-07-08 | Janssen Pharmaceutica Nv | Pyrido-and pyrimidopyrimidine derivatives as anti-proliferative agents |
US8933067B2 (en) | 2003-12-18 | 2015-01-13 | Janssen Pharmaceutica Nv | Pyrido and pyrimidopyrimidine derivatives as anti-profilerative agents |
US9688691B2 (en) | 2004-12-08 | 2017-06-27 | Janssen Pharmaceutica Nv | Macrocyclic quinazole derivatives and their use as MTKI |
US10208062B2 (en) | 2004-12-08 | 2019-02-19 | Janssen Pharmaceutica Nv | Macrocyclic quinazole derivatives and their use as MTKI |
US8492377B2 (en) | 2006-07-13 | 2013-07-23 | Janssen Pharmaceutica Nv | MTKI quinazoline derivatives |
US8318731B2 (en) | 2007-07-27 | 2012-11-27 | Janssen Pharmaceutica Nv | Pyrrolopyrimidines |
Also Published As
Publication number | Publication date |
---|---|
FR1176645A (en) | 1959-04-14 |
BE558251A (en) |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
ES8104233A1 (en) | Quinoline carboxylic acid derivatives | |
IE36797L (en) | 1,5-benzodiazepin-2-one derivatives. | |
GB807899A (en) | New photographic developers | |
ES264960A1 (en) | Photographic developers | |
ES463783A1 (en) | Cis-4a-phenyl-2,3,4,4a,5,6,7,7a-octahydro-1h-2-pyrindines and pharmaceutical compositions containing them | |
GB822846A (en) | Preparation and use of diaryl thienyl methane compounds | |
ATE20468T1 (en) | PROCESS FOR THE PREPARATION OF 4-HYDROXY-3(HETEROCYCLOCARBAMOYL)-2H-1,2-BENZOTHIAZINE-1,1DIOXIDES. | |
GB823001A (en) | Acaricidal compositions | |
GB857213A (en) | Color couplers containing long chain alkylamino-isophthalic-ester groups | |
US2707681A (en) | 8-aminolilolidines and 9-aminojulolidines and their addition salts and developer compositions containing the same | |
GB811632A (en) | Improvements in or relating to the preparation of steroid compounds | |
GB1011849A (en) | The manufacture of 3-amino-isoxazole compounds | |
GB951026A (en) | The manufacture of sulphonamides | |
JPS5592696A (en) | Reagent for detection of peroxidase | |
GB855022A (en) | Improvements in and relating to carbostyril derivatives | |
ES8307233A1 (en) | Derivatives of 1,4-thiazane-carboxylic acid, preparation and utilization thereof and compositions containing same | |
JPS5655383A (en) | Amizine derivative and its preparation | |
GB668659A (en) | Improvements in and relating to basic derivatives of imino dibenzyl compounds | |
ES251967A1 (en) | Phenothiazine derivatives, and their preparation | |
GB895422A (en) | New photographic developers | |
GB986644A (en) | Novel derivatives of salicylic acid and preparations thereof | |
GB872683A (en) | Improvements in or relating to colour photography | |
GB858432A (en) | Substituted para-aminophenols and their use as photographic developers | |
GB1081637A (en) | Novel ketones and the preparation thereof | |
GB840108A (en) | Diazotype materials sensitized with n-hetero-ú-aminobenzene-diazonium salts |