GB595844A - Improvements in and relating to the production and processing of photographic materials - Google Patents
Improvements in and relating to the production and processing of photographic materialsInfo
- Publication number
- GB595844A GB595844A GB32545A GB32545A GB595844A GB 595844 A GB595844 A GB 595844A GB 32545 A GB32545 A GB 32545A GB 32545 A GB32545 A GB 32545A GB 595844 A GB595844 A GB 595844A
- Authority
- GB
- United Kingdom
- Prior art keywords
- prepared
- acid
- acetylthioglycollic
- anilide
- dichloro
- 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
- 150000003931 anilides Chemical class 0.000 abstract 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 4
- CWERGRDVMFNCDR-UHFFFAOYSA-N Thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 3
- 230000003301 hydrolyzing Effects 0.000 abstract 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- KHXPZWDHAWLSAW-UHFFFAOYSA-N 2-acetyl-5-aminobenzonitrile Chemical compound CC(=O)C1=CC=C(N)C=C1C#N KHXPZWDHAWLSAW-UHFFFAOYSA-N 0.000 abstract 2
- 229960000583 Acetic Acid Drugs 0.000 abstract 2
- 229940051881 Anilide analgesics and antipyretics Drugs 0.000 abstract 2
- PGXLULGZZOZXRW-UHFFFAOYSA-N N-(2-benzoyl-4-nitrophenyl)acetamide Chemical compound CC(=O)NC1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1 PGXLULGZZOZXRW-UHFFFAOYSA-N 0.000 abstract 2
- CSSYMJHFGPFVKH-UHFFFAOYSA-N N-[4-(2-cyanoacetyl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(C(=O)CC#N)C=C1 CSSYMJHFGPFVKH-UHFFFAOYSA-N 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 2
- 230000000397 acetylating Effects 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 238000009835 boiling Methods 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- QDGJHZNOQSIFAT-UHFFFAOYSA-N 2-amino-4-chloro-5-methylphenol Chemical compound CC1=CC(O)=C(N)C=C1Cl QDGJHZNOQSIFAT-UHFFFAOYSA-N 0.000 abstract 1
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-Nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 abstract 1
- VMMDOCYDNRLESP-UHFFFAOYSA-N 4'-(chloroacetyl)acetanilide Chemical compound CC(=O)NC1=CC=C(C(=O)CCl)C=C1 VMMDOCYDNRLESP-UHFFFAOYSA-N 0.000 abstract 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N Acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract 1
- 229940040526 Anhydrous Sodium Acetate Drugs 0.000 abstract 1
- LRODIXGKIWFZJX-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)C1=C(NC(C)=O)C=CC=C1[N+](=O)[O-] Chemical compound C(C1=CC=CC=C1)(=O)C1=C(NC(C)=O)C=CC=C1[N+](=O)[O-] LRODIXGKIWFZJX-UHFFFAOYSA-N 0.000 abstract 1
- KPMWCYGABYHUHO-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)N(C(=O)C)C=1C=C(N)C=CC1 Chemical compound C(C1=CC=CC=C1)(=O)N(C(=O)C)C=1C=C(N)C=CC1 KPMWCYGABYHUHO-UHFFFAOYSA-N 0.000 abstract 1
- FEHKXRPPYLWZSG-UHFFFAOYSA-N Cl.C(C1=CC=CC=C1)(=O)N(C(=O)C)C1=CC=C(N)C=C1 Chemical compound Cl.C(C1=CC=CC=C1)(=O)N(C(=O)C)C1=CC=C(N)C=C1 FEHKXRPPYLWZSG-UHFFFAOYSA-N 0.000 abstract 1
- MNWBNISUBARLIT-UHFFFAOYSA-N Sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 abstract 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N Sulfuryl chloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract 1
- 239000012346 acetyl chloride Substances 0.000 abstract 1
- 230000001476 alcoholic Effects 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000000875 corresponding Effects 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- GKKZMYDNDDMXSE-UHFFFAOYSA-N ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- AFNBMGLGYSGFEZ-UHFFFAOYSA-M potassium;ethanethioate Chemical compound [K+].CC([S-])=O AFNBMGLGYSGFEZ-UHFFFAOYSA-M 0.000 abstract 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
- 229910052725 zinc Inorganic materials 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
- G03C7/3212—Couplers characterised by a group not in coupling site, e.g. ballast group, as far as the coupling rest is not specific
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Thioglycollic and acetylthioglycollic amides are prepared by reacting thioglycollic acid or acetylthioglycollic chloride with the appropriate amine. 2-Hydroxy-3 : 5-dichloro-4-methylthioglycollic anilide is prepared by heating 2-amino-4 : 6 - dichloro - 5 - methylphenol hydrochloride with thioglycollic acid and quinoline. 2-Hydroxy-thioglycollic anilide, 2 - hydroxy - 4 - methylthio - glycollic anilide, 2-hydroxy-4-methoxythioglycollic anilide, 2 -hydroxy-4-methyl-5-chlorothioglycollic anilide, 5 - (thioglycollylamino) - 1 - naphthol, and 1-phenyl-3-(thioglycollylamino)-5-pyrazolone are similarly prepared. 2-Hydroxy-4-methyl-5-chloro-a -dimethylthioglycollic anilide is similarly prepared using the free base of the corresponding amine, no quinoline, and a -mercaptoisobutyric acid. p-Acetylthioglycollylamino-o -cyanacetophenone is prepared by adding quinoline and then acetylthioglycollic chloride to a solution of p-amino-o -cyanacetophenone in dioxane. o -Benzoylacetamino - p - acetylthio - glycollic and o -benzoylacetamino-m-thioglucollic anilides are similarly prepared, and o -benzoylacetamino - p - thioglycollic and o - benzoylacetamino-m-thioglycollic anilides are prepared by hydrolysing the last-mentioned compounds with aqueous sodium hydroxide. Acetoacetylamino-p-acetylthioglycollic anilide is prepared by condensing p-(acetacetamino)-aniline with acetylthioglycollylchloride. 2 - a - Acetylmercaptopropionamido)-4 : 6-dichloro-5-methylphenol is prepared by reacting 2-(a -bromopropionamido)-4 : 6-dichloro-5-methylphenol with potassium thioacetate. Acetylthioglycollic acid is prepared by acetylating thioglycollic acid with acetyl chloride. Acetylthioglycollic chloride is prepared by reacting acetylthioglycollic acid with thionyl chloride. 2 - (a - Bromopropionamido) - 4 : 6 - dichloro - 5 - methylphenol is prepared by adding a -bromopropionyl bromide to a suspension of 2-amino-4 : 6-dichloro-5-methylphenol hydrochloride and anhydrous sodium acetate in glacial acetic acid. 2-Amino-4 : 6-dichloro-5-methylphenol hydrochloride is prepared by acetylating 2-amino-4-chloro-5-methylphenol with acetic acid and acetic anhydride, chlorinating with sulphuryl chloride, and hydrolysing by boiling with hydrochloric acid. p-Amino-o -cyanoacetophenone is prepared by hydrolysing p - cyanoacetylacetanilide in alcoholic solution by boiling with hydrochloric acid. p-Cyanoacetyl-acetanilide is prepared by heating p-chloroacetyl-acetanilide with an aqueousethyl alcohol solution of sodium cyanide. m-(Benzoylacetamino)-aniline is prepared by reducing o - benzoyl - m - nitroacetanilide with hydrogen in the presence of "Raney" nickel. o -(Benzoyl-m-nitroacetanilide is prepared by reacting ethyl benzoylacetate with m-nitraniline. o -Benzoyl-p-nitroacetanilide is similarly prepared. p-(Benzoylacetamino)-aniline hydrochloride is prepared by reducing o -benzoyl-p-nitroacetanilide with zinc and acetic acid, and treating with HCl.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB595844A true GB595844A (en) | 1947-12-18 |
Family
ID=1593321
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB32545A Expired GB595844A (en) | 1945-01-04 | Improvements in and relating to the production and processing of photographic materials |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB595844A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112326664A (en) * | 2020-09-27 | 2021-02-05 | 浙江安胜科技股份有限公司 | Automatic quality control method for heat-insulating container |
-
1945
- 1945-01-04 GB GB32545A patent/GB595844A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112326664A (en) * | 2020-09-27 | 2021-02-05 | 浙江安胜科技股份有限公司 | Automatic quality control method for heat-insulating container |
| CN112326664B (en) * | 2020-09-27 | 2023-06-13 | 浙江安胜科技股份有限公司 | Automatic quality control method for thermal insulation container |
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