GB733119A - Photographic colour couplers - Google Patents
Photographic colour couplersInfo
- Publication number
- GB733119A GB733119A GB20981/53A GB2098153A GB733119A GB 733119 A GB733119 A GB 733119A GB 20981/53 A GB20981/53 A GB 20981/53A GB 2098153 A GB2098153 A GB 2098153A GB 733119 A GB733119 A GB 733119A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tert
- amylphenoxy
- chloride
- reacting
- methyl
- 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
- -1 n is 0 or 1 Chemical class 0.000 abstract 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 9
- FZERHIULMFGESH-UHFFFAOYSA-N methylenecarboxanilide Natural products CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 abstract 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 6
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-L isophthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC(C([O-])=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-L 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 5
- 229960001413 acetanilide Drugs 0.000 abstract 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 229910052742 iron Inorganic materials 0.000 abstract 3
- FLUYDOVOMDZUEV-UHFFFAOYSA-N 2-(4-nitrophenoxy)acetyl chloride Chemical compound [O-][N+](=O)C1=CC=C(OCC(Cl)=O)C=C1 FLUYDOVOMDZUEV-UHFFFAOYSA-N 0.000 abstract 2
- NXTNASSYJUXJDV-UHFFFAOYSA-N 3-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(C(Cl)=O)=C1 NXTNASSYJUXJDV-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 2
- PFYHAAAQPNMZHO-UHFFFAOYSA-N Methyl 2-methoxybenzoate Chemical compound COC(=O)C1=CC=CC=C1OC PFYHAAAQPNMZHO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 abstract 2
- 150000002828 nitro derivatives Chemical class 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- 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 1
- SMLRWMFUJLCTFI-UHFFFAOYSA-N 3-(2-methoxyphenyl)-3-oxopropanoic acid Chemical compound COC1=CC=CC=C1C(=O)CC(O)=O SMLRWMFUJLCTFI-UHFFFAOYSA-N 0.000 abstract 1
- ORIBWNWUGUWUKV-UHFFFAOYSA-N 3-(3-nitrophenyl)prop-2-enoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(C=CC(Cl)=O)=C1 ORIBWNWUGUWUKV-UHFFFAOYSA-N 0.000 abstract 1
- QGGKQIDRZUUHAR-UHFFFAOYSA-N 3-amino-5-methoxycarbonylbenzoic acid Chemical compound COC(=O)C1=CC(N)=CC(C(O)=O)=C1 QGGKQIDRZUUHAR-UHFFFAOYSA-N 0.000 abstract 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 abstract 1
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003368 amide group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- KROPYAVVJDXRPH-UHFFFAOYSA-N ethyl 3-(2-methoxyphenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1OC KROPYAVVJDXRPH-UHFFFAOYSA-N 0.000 abstract 1
- KRAHENMBSVAAHD-UHFFFAOYSA-N ethyl 3-(4-methoxyphenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=C(OC)C=C1 KRAHENMBSVAAHD-UHFFFAOYSA-N 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 125000001424 substituent 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
- G03C7/36—Couplers containing compounds with active methylene groups
- G03C7/362—Benzoyl-acetanilide couplers
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Amides of the general formula <FORM:0733119/IV (b)/1> are described, wherein X represents -NHCO-, -(CH2)pCONH- where p is 0 to 4, -OCH2 CONH-, -O(CH2)3CONH- or -CH = CH CONH-, Z represents an alkyl group or an alkali metal, n is 0 or 1, radical I is connected to X in meta or para position and radical II carries the substituents shown in positions other than para to X. (4-Methoxybenzoyl)-4-{a -[2-(2 : 4 - di-tert. - amylphenoxy) - 5 - (3 : 5 - dicarbomethoxyphenyl carbamyl) phenyl carbamyl] methoxy} - acetanilide is prepared by reacting ethyl p-methoxy benzoylacetate with methyl 5 - [4 - (2 : 4 - di-tert. - amyl phenoxy)-3 - (4 - amino phenoxyacetamido) benzamido] isophthalate. Other compounds of the formula above are produced in a similar manner by reacting the appropriate intermediates (see below) with ethyl o-methoxybenzoyl acetate. (2 - Methoxybenzoyl) - 4 - [3 - (3 : 5 - dicarbomethoxy phenyl carbamylvaleramido)-6-(2 : 4-di-tert. - amylphenoxy) benzamido] acetanilide is made by reacting (2 - methoxybenzoyl) - 4-[3 - amino - 6 - (2 : 4 - di - tert. - amylphenoxy) benzamido] acetanilide with 3 : 5-dicarbomethoxyphenylcarbamylvaleryl chloride. The alkali metal salts of the above compounds may be obtained by hydrolysing the esters with, for example, sodium hydroxide. Methyl - 5 - [4 - (2 : 4 - di - tert. - amylphenoxy)-3 - (4 - aminophenoxyacetamido)benzamido] isophthalate is prepared by reducing the corresponding 4-nitrophenoxyacetamido compound with hydrogen and Raney nickel. Methyl - 5 - [4 - (2 : 4 - di - tert. - amylphenoxy)-3 - (4 - nitrophenoxyacetamido) benzamido] isophthalate is prepared by reacting p - nitrophenoxyacetyl chloride with methyl-5-[4-(2 : 4-di-tert.-amylphenoxy) - 3 - aminobenzamido] isophthalate. Similar compounds are obtained by using, in place of the p-nitrophenoxyacetyl chloride, p-nitrobenzoyl chloride, m-nitrobenzoyl chloride, m-nitrocinnamoyl chloride or in general, a compound of the formula NO2. C6H4.Y where Y is the acid chloride corresponding to the amide groups specified above for X, and the nitro compounds produced are reduced to the corresponding amino compounds and reacted with o-methoxy benzoyl acetate to give the compounds of the general formula as described above. Methyl - 5 - [4 - (2 : 4 - di - tert. - amylphenoxy)-3-aminobenzamido] isophthalate is prepared by reducing the corresponding 3-nitrobenzamido compound with iron and acetic acid. Methyl - 5 - [4 - (2 : 4 - di - tert. - amylphenoxy)-3 - nitrobenzamido] isophthalate is prepared by reacting 4(2 : 4 - di - tert. - amylphenoxy) - 3-nitrobenzoyl chloride with methyl 5-amino-isophthalate. 3 : 5 - Dicarbomethoxyphenylcarbamylvaleryl chloride is obtained by adding thionyl chloride to the corresponding acid. (2 - Methoxybenzoyl) - 4 - [3 - nitro - 6 - (2 : 4-di - tert. - amylphenoxy) benzamido] acetanilide is obtained by reacting o-methoxybenzoylacet-4-amino anilide with 2-(2 : 4-di-tert.-amylphenoxy)5 - nitrobenzoyl chloride, and the nitro compound is reduced to the corresponding 3-amino compound with iron and acetic acid. o - Methoxybenzoylacet - 4 - nitroanilide is prepared by reacting p-nitroaniline with o-methoxybenzoylacetate. The nitro group is then reduced to amino with iron and acetic acid. Ethyl o - methoxybenzoylacetate is obtained by reacting methyl o-methoxybenzoate with ethyl acetate in the presence of sodium.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US301962A US2652329A (en) | 1952-07-31 | 1952-07-31 | Color couplers containing isophthalic acid radicals |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB733119A true GB733119A (en) | 1955-07-06 |
Family
ID=23165663
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB20981/53A Expired GB733119A (en) | 1952-07-31 | 1953-07-29 | Photographic colour couplers |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US2652329A (en) |
| GB (1) | GB733119A (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB784422A (en) * | 1955-01-29 | 1957-10-09 | Ilford Ltd | Improvements in or relating to colour photography |
| US2908573A (en) * | 1956-07-25 | 1959-10-13 | Eastman Kodak Co | Photographic color couplers containing mono-n-alkyl groups |
| US2870012A (en) * | 1955-12-23 | 1959-01-20 | Eastman Kodak Co | Microdispersions of photographic color couplers |
| BE559466A (en) * | 1956-07-27 | |||
| US2993791A (en) * | 1957-10-31 | 1961-07-25 | Gen Aniline & Film Corp | Color couplers containing long chain alkylaminoisophthalicester groups |
| US3265506A (en) * | 1964-05-04 | 1966-08-09 | Eastman Kodak Co | Yellow forming couplers |
| US3658544A (en) * | 1968-08-12 | 1972-04-25 | Konishiroku Photo Ind | Light-sensitive silver halide color-photographic emulsions |
-
1952
- 1952-07-31 US US301962A patent/US2652329A/en not_active Expired - Lifetime
-
1953
- 1953-07-29 GB GB20981/53A patent/GB733119A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US2652329A (en) | 1953-09-15 |
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