GB1008177A - N-alkyl-n-acylaminoproprionamides and their use as photographic couplers - Google Patents
N-alkyl-n-acylaminoproprionamides and their use as photographic couplersInfo
- Publication number
- GB1008177A GB1008177A GB6822/64A GB682264A GB1008177A GB 1008177 A GB1008177 A GB 1008177A GB 6822/64 A GB6822/64 A GB 6822/64A GB 682264 A GB682264 A GB 682264A GB 1008177 A GB1008177 A GB 1008177A
- Authority
- GB
- United Kingdom
- Prior art keywords
- propionate
- methyl
- converted
- chloride
- reacted
- 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
- 150000001875 compounds Chemical class 0.000 abstract 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 abstract 2
- 230000008878 coupling Effects 0.000 abstract 2
- 238000010168 coupling process Methods 0.000 abstract 2
- 238000005859 coupling reaction Methods 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 abstract 1
- BTKUVAFAEJMOIG-UHFFFAOYSA-N 3-(butylazaniumyl)propanoate Chemical compound CCCCNCCC(O)=O BTKUVAFAEJMOIG-UHFFFAOYSA-N 0.000 abstract 1
- LQPJTCDHUDFCAK-UHFFFAOYSA-N 3-[butyl(tetradecanoyl)amino]propanoic acid Chemical compound C(CCC)N(C(CCCCCCCCCCCCC)=O)CCC(=O)O LQPJTCDHUDFCAK-UHFFFAOYSA-N 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical group CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 abstract 1
- IPIVAXLHTVNRBS-UHFFFAOYSA-N decanoyl chloride Chemical compound CCCCCCCCCC(Cl)=O IPIVAXLHTVNRBS-UHFFFAOYSA-N 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- JUXSDNMTSOPPRW-UHFFFAOYSA-N methyl 3-(butylamino)propanoate Chemical compound CCCCNCCC(=O)OC JUXSDNMTSOPPRW-UHFFFAOYSA-N 0.000 abstract 1
- XUGHCXKKLJWPFH-UHFFFAOYSA-N methyl 3-[butyl(decanoyl)amino]propanoate Chemical compound C(CCC)N(C(CCCCCCCCC)=O)CCC(=O)OC XUGHCXKKLJWPFH-UHFFFAOYSA-N 0.000 abstract 1
- NLWBXCDIGQPPCJ-UHFFFAOYSA-N methyl 3-[butyl(dodecanoyl)amino]propanoate Chemical compound C(CCC)N(C(CCCCCCCCCCC)=O)CCC(=O)OC NLWBXCDIGQPPCJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
- CSMRVRGWMFCCFP-UHFFFAOYSA-N n-(2-aminoethyl)-1-hydroxynaphthalene-2-carboxamide Chemical compound C1=CC=CC2=C(O)C(C(=O)NCCN)=CC=C21 CSMRVRGWMFCCFP-UHFFFAOYSA-N 0.000 abstract 1
- 125000000962 organic group Chemical group 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 abstract 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 abstract 1
- LPWCRLGKYWVLHQ-UHFFFAOYSA-N tetradecanoyl chloride Chemical compound CCCCCCCCCCCCCC(Cl)=O LPWCRLGKYWVLHQ-UHFFFAOYSA-N 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)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Abstract
The invention comprises a compound suitable for use as a photographic coupler represented by the general formula <FORM:1008177/C2/1> wherein A is a coupling component, i.e. an organic group capable of reacting with the oxidation product of a coupling developer of the p-phenylenediamine type to form a dye, having at least one active methylene group, pyrazolone nucleus or phenolic hydroxyl group, and n is an integer in the range of from 6 to 12. The compounds can be made by reacting a 3-(N-butyl-alkylamido) propionic acid chloride with an amine A-NH2. The following novel compounds are prepared in examples <FORM:1008177/C2/2> In Examples (1), methyl acrylate and butylamine form 3-butylamino-propionate which is reacted with myristic chloride to give methyl 3 - (N - butyltetradecanamido) propionate; the latter is hydrolysed to the acid and converted to the acid chloride which is reacted with N-(2-aminoethyl) - 1 - hydroxy - 2 - naphthamide to form (I); (2) methyl 3-(N-butyldecanamido)-propionate is made from methyl 3-(butylamino)-propionate and capric chloride and its acid chloride reacted with 4-aminobenzoylaceto-2-methoxyanilide to give (II): (3) methyl 3-(N-butyldodecanamido) - propionate is made in a similar manner and converted to (III); (4) similarly methyl 3-(N-butyloctanamido) propionate is made and converted to (IV); (5) 3 - (N - butyltetradecanamido) propionic acid is converted to (V).
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB6822/64A GB1008177A (en) | 1964-02-08 | 1964-02-08 | N-alkyl-n-acylaminoproprionamides and their use as photographic couplers |
| US345120A US3337344A (en) | 1964-02-08 | 1964-02-17 | Color photographic silver halide emulsion |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB6822/64A GB1008177A (en) | 1964-02-08 | 1964-02-08 | N-alkyl-n-acylaminoproprionamides and their use as photographic couplers |
| US345120A US3337344A (en) | 1964-02-08 | 1964-02-17 | Color photographic silver halide emulsion |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1008177A true GB1008177A (en) | 1965-10-27 |
Family
ID=26240965
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB6822/64A Expired GB1008177A (en) | 1964-02-08 | 1964-02-08 | N-alkyl-n-acylaminoproprionamides and their use as photographic couplers |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US3337344A (en) |
| GB (1) | GB1008177A (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3418129A (en) * | 1963-12-27 | 1968-12-24 | Fuji Shoshin Film Kabushiki Ka | Color photographic silver halide emulsion |
| US3711546A (en) * | 1966-12-02 | 1973-01-16 | M Simon | N-(ortho-substituted benzene or naphthalene carboxamidoethyle)para-phenylene diamines as coupler-developers |
| FR1587138A (en) * | 1967-11-18 | 1970-03-13 | ||
| US4361589A (en) * | 1980-09-30 | 1982-11-30 | General Foods Corporation | Infused dried celery |
| JP2597908B2 (en) | 1989-04-25 | 1997-04-09 | 富士写真フイルム株式会社 | Silver halide color photographic materials |
| DE69530198T2 (en) * | 1995-09-18 | 2004-01-29 | Ferrania Spa | Process for the preparation of 4-arylthio-5-pyrazolone 2-equivalent magnetic couplers |
| EP0921435B1 (en) * | 1997-12-02 | 2002-07-24 | Tulalip Consultoria Comercial Sociedade Unipessoal S.A. | Light-sensitive silver halide photographic elements containing yellow filter dyes |
| JP4887201B2 (en) | 2007-04-13 | 2012-02-29 | 富士フイルム株式会社 | Silver halide photographic light-sensitive material and image forming method using the same |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3135609A (en) * | 1960-06-29 | 1964-06-02 | Gen Aniline & Film Corp | 1-hydroxy-2-naphthamide couplers for color photography |
-
1964
- 1964-02-08 GB GB6822/64A patent/GB1008177A/en not_active Expired
- 1964-02-17 US US345120A patent/US3337344A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US3337344A (en) | 1967-08-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1513537A (en) | Malonic acid diamides containing a triazole ring and photographic light-sensitive materials containing them | |
| SE7506292L (en) | N-SUBSTITUTED-14-HYDROXY-3-SUBSTITUTED-MORPHINE DERIVATIVES AND PROCEDURES FOR THE MANUFACTURE | |
| GB1008177A (en) | N-alkyl-n-acylaminoproprionamides and their use as photographic couplers | |
| GB1042632A (en) | New indane derivatives and processes for the preparation thereof | |
| GB1043505A (en) | Water-soluble disazo-dyestuffs and process for preparing them | |
| GB1065172A (en) | Bluensidine and its derivatives | |
| GB1042480A (en) | Substituted pyridyl coumarins | |
| GB949944A (en) | Amide colour couplers | |
| GB708065A (en) | Improvements in the production of photographic images | |
| GB1018810A (en) | N-alkyl-n-acylaminoproprionamides and their use as photographic couplers | |
| GB1093113A (en) | 6-substituted penicillanyl alcohols | |
| GB1095359A (en) | ||
| GB944838A (en) | Improvements in or relating to colour couplers and to their production and use in colour photography | |
| GB1149514A (en) | Colour couplers soluble in organic solvents and having an oil-solubilizing group | |
| GB955353A (en) | Improvements in or relating to novel pyridine derivatives | |
| GB1228041A (en) | ||
| GB1031545A (en) | Derivatives of trifluoromethylphthalic acid | |
| GB1063364A (en) | Oxazine compounds and the preparation thereof | |
| GB1036079A (en) | Water-insoluble styryl dyestuffs and processes for their manufacture | |
| GB975773A (en) | Improvements in or relating to the manufacture of photographic colour images | |
| GB855022A (en) | Improvements in and relating to carbostyril derivatives | |
| GB1124198A (en) | S-acylthiamine-o-acylates and process for preparing the same | |
| GB874205A (en) | Improvements in or relating to triazaindolizine derivatives | |
| GB1078164A (en) | Pyrazolone colour couplers and process for obtaining colour photographic images therewith | |
| GB1081636A (en) | Novel oximes and a process for the preparation thereof |