GB898706A - Azo dyes derived from dihydroxyphenyl ketones and their use in photography - Google Patents
Azo dyes derived from dihydroxyphenyl ketones and their use in photographyInfo
- Publication number
- GB898706A GB898706A GB28756/58A GB2875658A GB898706A GB 898706 A GB898706 A GB 898706A GB 28756/58 A GB28756/58 A GB 28756/58A GB 2875658 A GB2875658 A GB 2875658A GB 898706 A GB898706 A GB 898706A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dyes
- indicated
- propionyl
- methoxy
- coupling
- 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
- 239000000987 azo dye Substances 0.000 title 1
- JHUWODOJJBBFNF-UHFFFAOYSA-N bis(2,3-dihydroxyphenyl)methanone Chemical class OC1=CC=CC(C(=O)C=2C(=C(O)C=CC=2)O)=C1O JHUWODOJJBBFNF-UHFFFAOYSA-N 0.000 title 1
- 238000010168 coupling process Methods 0.000 abstract 6
- 230000008878 coupling Effects 0.000 abstract 5
- 238000005859 coupling reaction Methods 0.000 abstract 5
- 239000000975 dye Substances 0.000 abstract 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- -1 p-dihydroxyphenyl Chemical group 0.000 abstract 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 abstract 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 abstract 2
- UHKAJLSKXBADFT-UHFFFAOYSA-N 1,3-indandione Chemical compound C1=CC=C2C(=O)CC(=O)C2=C1 UHKAJLSKXBADFT-UHFFFAOYSA-N 0.000 abstract 1
- MUVQKFGNPGZBII-UHFFFAOYSA-N 1-anthrol Chemical compound C1=CC=C2C=C3C(O)=CC=CC3=CC2=C1 MUVQKFGNPGZBII-UHFFFAOYSA-N 0.000 abstract 1
- MRBHUTYSDDTIIF-UHFFFAOYSA-N 1-hydroxy-n-phenylnaphthalene-2-carboxamide Chemical compound C1=CC2=CC=CC=C2C(O)=C1C(=O)NC1=CC=CC=C1 MRBHUTYSDDTIIF-UHFFFAOYSA-N 0.000 abstract 1
- NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 abstract 1
- CZTSOXCSVFEFIK-UHFFFAOYSA-N 2-benzylnaphthalen-1-ol Chemical class C1=CC2=CC=CC=C2C(O)=C1CC1=CC=CC=C1 CZTSOXCSVFEFIK-UHFFFAOYSA-N 0.000 abstract 1
- JXPDNDHCMMOJPC-UHFFFAOYSA-N 2-hydroxybutanedinitrile Chemical compound N#CC(O)CC#N JXPDNDHCMMOJPC-UHFFFAOYSA-N 0.000 abstract 1
- 229930194542 Keto Natural products 0.000 abstract 1
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 abstract 1
- 150000001448 anilines Chemical class 0.000 abstract 1
- 125000001769 aryl amino group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000005518 carboxamido group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 1
- 238000006193 diazotization reaction Methods 0.000 abstract 1
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 abstract 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 229910052736 halogen Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000000468 ketone group Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- FZZQNEVOYIYFPF-UHFFFAOYSA-N naphthalene-1,6-diol Chemical compound OC1=CC=CC2=CC(O)=CC=C21 FZZQNEVOYIYFPF-UHFFFAOYSA-N 0.000 abstract 1
- 150000004780 naphthols Chemical class 0.000 abstract 1
- 150000005002 naphthylamines Chemical class 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 abstract 1
- 150000003233 pyrroles Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B39/00—Other azo dyes prepared by diazotising and coupling
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
-
- 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
- G03C8/00—Diffusion transfer processes or agents therefor; Photosensitive materials for such processes
- G03C8/02—Photosensitive materials characterised by the image-forming section
- G03C8/08—Photosensitive materials characterised by the image-forming section the substances transferred by diffusion consisting of organic compounds
- G03C8/10—Photosensitive materials characterised by the image-forming section the substances transferred by diffusion consisting of organic compounds of dyes or their precursors
- G03C8/12—Photosensitive materials characterised by the image-forming section the substances transferred by diffusion consisting of organic compounds of dyes or their precursors characterised by the releasing mechanism
- G03C8/14—Oxidation of the chromogenic substances
- G03C8/16—Oxidation of the chromogenic substances initially diffusible in alkaline environment
- G03C8/18—Dye developers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Coloring (AREA)
Abstract
The invention comprises dyes of formula <FORM:0898706/IV (c)/1> where Ar is an aryl nucleus, Z is OH, Hlg, Alk or AlkO, m 0 or 1, n 0 or 1-4, q 1 or 2, R alkylene, Y o- or p-dihydroxyphenyl or an alkyl or halogen substituted derivative thereof and Xa and Xb are coupling component residues. The dyes are made by conventional diazotization and coupling processes and the hydroxy groups in Y may be protected during these processes by using, e.g. in the form of o-acetyl derivatives. Benzene and naphthalene nuclei are indicated for Ar. Preferred alkyl and alkoxy groups for Z are those containing 1-5 carbon atoms. Preferred dyes are those in which Ar is a benzene residue and where R is an ethylene group. Representative of indicated coupling components are phenol, anilines, naphthols, anthrols, naphthylamines, pyrazolones, pyrroles, 1,3-diketones and beta-ketonic acid arylamides. The coupling components may contain substituents such as alkyl, sulpho, alkoxy, aryl, aryloxy, amino, keto, alkylamino, arylamino, hydroxy, cyano, alkylamido, arylamido, carbalkoxy, carboxamido and sulphonamido groups. Preferred diazo components are 2 - [gamma - (21, 51 - dimethoxy - 31 - aminophenyl) - propionyl and beta - methyl - propionyl - ] - and 2 - (gamma - [21, 51 - di - methoxy - 31 - (211, 511 - dimethoxy 311 - amino - phenylazo) - phenyl] - propionyl) - hydroquinones. Amongst coupling components indicated or specified are 4-methyl, methoxy- and benzyl-1-naphthols, 4-methoxy- and -aectamido-a -naphthylamines, 1,5-naphtholenediamine, 1-hydroxy-2-naphthanilide, phenol, p-cresol, aniline, 2,5-dimethoxyaniline, 1-hydroxyanthracene, diketohydrindene, malonitrile, acetoacetanilide and 1-phenyl - 3 - methyl - 5 - pyrazolone. Indicated coupling components for use in compounds where p is Z are 1,6-dihydroxynaphthalene and 1-naphthol. A further indicated value for R is isopropylene. The dyes are developers and are of particular use in colour photography. Examples are provided of the preparation of the dyes and thie use in photographic processes and compositions. Specifications 804,971, 804,972, 811,579, 853,478, 853,479 and 898,707 are referred to.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68508157A | 1957-09-20 | 1957-09-20 | |
| US68506657A | 1957-09-20 | 1957-09-20 | |
| US222702A US3208991A (en) | 1957-09-20 | 1962-09-10 | Azo dye developers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB898706A true GB898706A (en) | 1962-06-14 |
Family
ID=27397130
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB19820/61A Expired GB898707A (en) | 1957-09-20 | 1958-09-08 | Dihydroxyphenylketonic compounds and their use in photography |
| GB28756/58A Expired GB898706A (en) | 1957-09-20 | 1958-09-08 | Azo dyes derived from dihydroxyphenyl ketones and their use in photography |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB19820/61A Expired GB898707A (en) | 1957-09-20 | 1958-09-08 | Dihydroxyphenylketonic compounds and their use in photography |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3208991A (en) |
| BE (1) | BE571336A (en) |
| DE (2) | DE1419866A1 (en) |
| FR (1) | FR1215651A (en) |
| GB (2) | GB898707A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4247455A (en) * | 1978-08-02 | 1981-01-27 | Polaroid Corporation | Yellow 2:1 azo-azo or azo-azomethine chrome complexed dye developers |
| WO2005118551A2 (en) * | 2004-05-28 | 2005-12-15 | Ligand Pharmaceuticals Inc. | Thrombopoietin activity modulating compounds and methods |
| CA2583764C (en) * | 2004-10-25 | 2009-06-09 | Ligand Pharmaceuticals, Inc. | Thrombopoietin activity modulating compounds and methods |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL105918C (en) * | 1956-02-13 | 1900-01-01 | ||
| US2997390A (en) * | 1956-09-04 | 1961-08-22 | Polaroid Corp | Novel color processes and products |
| US3009958A (en) * | 1957-06-06 | 1961-11-21 | Polaroid Corp | Hydroquinonyl derivatives and their synthesis |
-
1958
- 1958-09-08 GB GB19820/61A patent/GB898707A/en not_active Expired
- 1958-09-08 GB GB28756/58A patent/GB898706A/en not_active Expired
- 1958-09-10 DE DE19581419866 patent/DE1419866A1/en active Pending
- 1958-09-10 DE DEI15383A patent/DE1129371B/en active Pending
- 1958-09-19 BE BE571336A patent/BE571336A/xx unknown
- 1958-09-19 FR FR774891A patent/FR1215651A/en not_active Expired
-
1962
- 1962-09-10 US US222702A patent/US3208991A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE1419866A1 (en) | 1968-11-21 |
| GB898707A (en) | 1962-06-14 |
| US3208991A (en) | 1965-09-28 |
| BE571336A (en) | 1959-03-19 |
| DE1129371B (en) | 1962-05-10 |
| FR1215651A (en) | 1960-04-20 |
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