GB577387A - Improvements in or relating to dyestuff intermediates and their use in colour photography - Google Patents
Improvements in or relating to dyestuff intermediates and their use in colour photographyInfo
- Publication number
- GB577387A GB577387A GB6791/44A GB679144A GB577387A GB 577387 A GB577387 A GB 577387A GB 6791/44 A GB6791/44 A GB 6791/44A GB 679144 A GB679144 A GB 679144A GB 577387 A GB577387 A GB 577387A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- ether
- sulphonic
- benzene
- aqueous
- 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
- 239000000975 dye Substances 0.000 title 1
- 239000000543 intermediate Substances 0.000 title 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- -1 nitro, hydroxy, amino Chemical group 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 2
- 125000004423 acyloxy group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 238000005859 coupling reaction Methods 0.000 abstract 2
- 150000004985 diamines Chemical class 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- NHTWIOHQAQDWOM-UHFFFAOYSA-N naphthalene;sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O.C1=CC=CC2=CC=CC=C21 NHTWIOHQAQDWOM-UHFFFAOYSA-N 0.000 abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- HGVJHAMFCVPSRK-UHFFFAOYSA-N 1-hydroxy-2h-naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(O)(S(O)(=O)=O)CC=CC2=C1 HGVJHAMFCVPSRK-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 abstract 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 1
- 239000012736 aqueous medium Substances 0.000 abstract 1
- 150000004984 aromatic diamines Chemical class 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000002843 carboxylic acid group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 239000012457 nonaqueous media Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000001632 sodium acetate Substances 0.000 abstract 1
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000001174 sulfone group Chemical class 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- 150000003568 thioethers Chemical group 0.000 abstract 1
- 125000005270 trialkylamine group Chemical group 0.000 abstract 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
- G03C7/32—Colour coupling substances
- G03C7/34—Couplers containing phenols
- G03C7/344—Naphtholic couplers
-
- 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
- G03C7/32—Colour coupling substances
- G03C7/34—Couplers containing phenols
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)
Abstract
Disulphonamides of the general formula <FORM:0577387/IV/1> wherein positions ortho or para to the hydroxyl groups are reactive and A represents a divalent radicle of at least 8 carbon atoms and includes at least one benzene ring, are made by condensing an appropriate naphthalene sulphonyl chloride containing an acyloxy or oxycarbalkoxy (i.e. -O-COO Alkyl) group in the 1-position with an appropriate aromatic diamine and hydrolysing the acyloxy or oxycarbalkoxy group. The positions ortho or para to the hydroxyl groups may be unsubstituted or they may contain an atom or group, e.g. a chlorine or bromine atom or a sulphonic or carboxylic acid group, which does not inhibit dye-coupling reactions, and which is generally split off during such reactions. Condensation may be effected in aqueous or non-aqueous media, e.g. in ether, acetone, acetic acid or dioxane, and a basic agent such as pyridine, a trialkylamine, triethanolamine or sodium carbonate, hydroxide or acetate, may be present. In an example, 1 - oxycarbethoxynaphthalene - 2 - sulphonyl chloride is condensed with 4 : 41-diaminodiphenyl ether, 1 : 4-bis-(aminomethyl)-benzene, 1 : 5 - naphthylenediamine, 4 : 41 - diaminodi - phenylmethane, 4 : 41-diaminodiphenylmethane-3 : 31-dicarboxylic acid or p-bis-(b -aminoethyl)-benzene, and the product hydrolysed with an aqueous-alcoholic solution of potassium hydroxide. Additional diamines specified are 2 : 21-, 2 : 41-and 4 : 41-diaminostilbenes and benzidine. The nuclei of such diamines may be substituted by groups which do not enter into dye-coupling reactions, e.g. by hydrocarbon radicles (e.g. alkyl, aryl or aralkyl), halogen atoms or ether, nitro, hydroxy, amino, hydrocarbon-substituted amino, carboxy, nitrile, sulphonic, sulphone, sulphinic or sulphide groups. Specifications 497,698, 544,189, 545,433, [Group XX], 554,302 and 556,858, [Group XX], are referred to. Naphthalene sulphonyl chlorides used as starting materials above are prepared by treating 1-hydroxynaphthalene sulphonic acids, such as the 1 : 2- and 1 : 5-isomers, with a chloroformic ester or with an acylating agent, such as acetic anhydride or acetyl p chloride, and treating the products with phosphorus pentachloride.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US483333A US2395484A (en) | 1943-04-16 | 1943-04-16 | Bis sulphonamides of naphthol sulphonyl chlorides with aromatic diamines |
| US593090A US2435629A (en) | 1943-04-16 | 1945-05-10 | Processes of color photography and compositions and elements therefor for utilizing sulfonamide color formers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB577387A true GB577387A (en) | 1946-05-16 |
Family
ID=27047607
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB6791/44A Expired GB577387A (en) | 1943-04-16 | 1944-04-13 | Improvements in or relating to dyestuff intermediates and their use in colour photography |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US2435629A (en) |
| GB (1) | GB577387A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2635535A (en) * | 1946-01-31 | 1953-04-21 | Du Pont | Mordanting |
| NL92883C (en) * | 1953-07-01 | |||
| DE2448063C2 (en) * | 1974-10-09 | 1984-06-07 | Agfa-Gevaert Ag, 5090 Leverkusen | Color photographic recording material |
| CA2680139A1 (en) * | 2007-03-05 | 2008-09-12 | Biolipox Ab | New methylenebisphenyl compounds useful in the treatment of inflammation |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE414965A (en) * | 1935-04-12 | |||
| US2168183A (en) * | 1935-10-30 | 1939-08-01 | Agfa Ansco Corp | Stereophotography |
| GB503814A (en) * | 1936-07-07 | 1939-04-11 | Kodak Ltd | Improvements in three-colour photographic materials |
| US2356475A (en) * | 1936-07-07 | 1944-08-22 | Eastman Kodak Co | Phenolic and naphtholic couplers containing sulphonamide groups |
| GB531312A (en) * | 1939-03-31 | 1941-01-01 | Eastman Kodak Co | Improvements in and relating to colour forming developers and processes of colour development |
| US2271238A (en) * | 1939-03-31 | 1942-01-27 | Eastman Kodak Co | Color forming compounds containing sulphonamide groups |
| BE442478A (en) * | 1940-07-12 | |||
| CH227990A (en) * | 1940-07-17 | 1943-07-31 | Ig Farbenindustrie Ag | Process for the preparation of color photographic images. |
| US2363764A (en) * | 1940-08-01 | 1944-11-28 | Du Pont | Color photography |
-
1944
- 1944-04-13 GB GB6791/44A patent/GB577387A/en not_active Expired
-
1945
- 1945-05-10 US US593090A patent/US2435629A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US2435629A (en) | 1948-02-10 |
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