DE900781C - Diffusionsfeste Gelbfarbbildner der Benzimidazolklasse - Google Patents
Diffusionsfeste Gelbfarbbildner der BenzimidazolklasseInfo
- Publication number
- DE900781C DE900781C DEG186A DEG0000186A DE900781C DE 900781 C DE900781 C DE 900781C DE G186 A DEG186 A DE G186A DE G0000186 A DEG0000186 A DE G0000186A DE 900781 C DE900781 C DE 900781C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- octadecylbenzimidazole
- sulfonic acid
- diffusion
- yellow color
- 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
- 238000009792 diffusion process Methods 0.000 title claims 3
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title 1
- 239000000839 emulsion Substances 0.000 claims description 16
- -1 silver halide Chemical class 0.000 claims description 11
- 239000004332 silver Substances 0.000 claims description 8
- 229910052709 silver Inorganic materials 0.000 claims description 8
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000003435 aroyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- MAASTUUGNAGUER-UHFFFAOYSA-N 2-(2-acetamido-3-benzoylphenyl)-1-octadecylbenzimidazole-5-sulfonic acid Chemical compound C(C1=CC=CC=C1)(=O)C=1C(=C(C=CC1)C1=NC2=C(N1CCCCCCCCCCCCCCCCCC)C=CC(=C2)S(=O)(=O)O)NC(=O)C MAASTUUGNAGUER-UHFFFAOYSA-N 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 229940125782 compound 2 Drugs 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- 239000000975 dye Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- JHHVDPLPBJASDF-UHFFFAOYSA-N 2-(4-aminophenyl)-1-octadecylbenzimidazole-5-sulfonic acid Chemical compound N=1C2=CC(S(O)(=O)=O)=CC=C2N(CCCCCCCCCCCCCCCCCC)C=1C1=CC=C(N)C=C1 JHHVDPLPBJASDF-UHFFFAOYSA-N 0.000 description 5
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- 239000001043 yellow dye Substances 0.000 description 3
- BWWHTIHDQBHTHP-UHFFFAOYSA-N 2-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1C(Cl)=O BWWHTIHDQBHTHP-UHFFFAOYSA-N 0.000 description 2
- DWYHDSLIWMUSOO-UHFFFAOYSA-N 2-phenyl-1h-benzimidazole Chemical class C1=CC=CC=C1C1=NC2=CC=CC=C2N1 DWYHDSLIWMUSOO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 150000003142 primary aromatic amines Chemical class 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-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
- 239000000243 solution Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- UAORZSGYNWRBJP-UHFFFAOYSA-N 2-(2-acetamido-4-benzoylphenyl)-1-octadecylbenzimidazole-5-sulfonic acid Chemical compound C(C1=CC=CC=C1)(=O)C1=CC(=C(C=C1)C1=NC2=C(N1CCCCCCCCCCCCCCCCCC)C=CC(=C2)S(=O)(=O)O)NC(=O)C UAORZSGYNWRBJP-UHFFFAOYSA-N 0.000 description 1
- IKHMWULQCYUZFW-UHFFFAOYSA-N 3,5-dioxo-n,5-diphenylpentanamide Chemical compound C=1C=CC=CC=1C(=O)CC(=O)CC(=O)NC1=CC=CC=C1 IKHMWULQCYUZFW-UHFFFAOYSA-N 0.000 description 1
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
- HXUIDZOMTRMIOE-UHFFFAOYSA-M 3-oxo-3-phenylpropionate Chemical compound [O-]C(=O)CC(=O)C1=CC=CC=C1 HXUIDZOMTRMIOE-UHFFFAOYSA-M 0.000 description 1
- 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
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- QTDMLGZSPQGELY-UHFFFAOYSA-N CCCCCCCCCCCCCCCCCCN1C(C(C=CC(C#N)=C2)=C2NC(C)=O)=NC2=C1C=CC(S(O)(=O)=O)=C2 Chemical compound CCCCCCCCCCCCCCCCCCN1C(C(C=CC(C#N)=C2)=C2NC(C)=O)=NC2=C1C=CC(S(O)(=O)=O)=C2 QTDMLGZSPQGELY-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- SZQSTETUIRSWNO-UHFFFAOYSA-N NC=1C=C(C=CC1)C1=NC2=C(N1CCCCCCCCCCCCCCCCCC)C=CC(=C2)S(=O)(=O)O Chemical compound NC=1C=C(C=CC1)C1=NC2=C(N1CCCCCCCCCCCCCCCCCC)C=CC(=C2)S(=O)(=O)O SZQSTETUIRSWNO-UHFFFAOYSA-N 0.000 description 1
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- G03C7/32—Colour coupling substances
- G03C7/36—Couplers containing compounds with active methylene groups
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59203A US2500487A (en) | 1948-11-09 | 1948-11-09 | Yellow diffusion-fast color formers of the benzimidazole class |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE900781C true DE900781C (de) | 1954-01-04 |
Family
ID=22021460
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEG186A Expired DE900781C (de) | 1948-11-09 | 1949-10-28 | Diffusionsfeste Gelbfarbbildner der Benzimidazolklasse |
Country Status (5)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1107188C (zh) * | 1998-06-22 | 2003-04-30 | 开利公司 | 风机安装组件 |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE565656A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1957-03-15 | |||
| JP2805414B2 (ja) * | 1992-05-11 | 1998-09-30 | 富士写真フイルム株式会社 | ハロゲン化銀カラー写真感光材料 |
| PL366799A1 (en) * | 2001-07-27 | 2005-02-07 | Curis, Inc. | Mediators of hedgehog signaling pathways, compositions and uses related thereto |
| GB0400781D0 (en) * | 2004-01-14 | 2004-02-18 | Novartis Ag | Organic compounds |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2179239A (en) * | 1935-04-10 | 1939-11-07 | Agfa Ansco Corp | Color photography |
| NL49334C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1935-08-07 | |||
| FR881899A (fr) * | 1940-10-19 | 1943-05-11 | Ig Farbenindustrie Ag | Procédé de production d'images photographiques en couleurs |
-
0
- BE BE492063D patent/BE492063A/xx unknown
- FR FR998985D patent/FR998985A/fr not_active Expired
-
1948
- 1948-11-09 US US59203A patent/US2500487A/en not_active Expired - Lifetime
-
1949
- 1949-10-18 GB GB26687/49A patent/GB659479A/en not_active Expired
- 1949-10-28 DE DEG186A patent/DE900781C/de not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1107188C (zh) * | 1998-06-22 | 2003-04-30 | 开利公司 | 风机安装组件 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB659479A (en) | 1951-10-24 |
| FR998985A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1952-01-24 |
| BE492063A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | |
| US2500487A (en) | 1950-03-14 |
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