US3733335A - Indazolone magenta couplers - Google Patents
Indazolone magenta couplers Download PDFInfo
- Publication number
- US3733335A US3733335A US00104510A US3733335DA US3733335A US 3733335 A US3733335 A US 3733335A US 00104510 A US00104510 A US 00104510A US 3733335D A US3733335D A US 3733335DA US 3733335 A US3733335 A US 3733335A
- Authority
- US
- United States
- Prior art keywords
- parts
- group
- indazolone
- acetyl
- compound
- 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 - Lifetime
Links
- LOCAIGRSOJUCTB-UHFFFAOYSA-N indazol-3-one Chemical compound C1=CC=C2C(=O)N=NC2=C1 LOCAIGRSOJUCTB-UHFFFAOYSA-N 0.000 title abstract description 13
- -1 PHENYL GROUP Chemical group 0.000 abstract description 35
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 16
- 150000001732 carboxylic acid derivatives Chemical group 0.000 abstract description 3
- 150000003949 imides Chemical class 0.000 abstract description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- 150000001875 compounds Chemical class 0.000 description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 14
- 229910052799 carbon Inorganic materials 0.000 description 14
- 229910052739 hydrogen Inorganic materials 0.000 description 14
- 239000001257 hydrogen Substances 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
- 229960000583 acetic acid Drugs 0.000 description 10
- 229910052709 silver Inorganic materials 0.000 description 10
- 239000004332 silver Substances 0.000 description 10
- 125000002843 carboxylic acid group Chemical group 0.000 description 9
- 239000012362 glacial acetic acid Substances 0.000 description 9
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 125000005544 phthalimido group Chemical group 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- SWEICGMKXPNXNU-UHFFFAOYSA-N 1,2-dihydroindazol-3-one Chemical compound C1=CC=C2C(O)=NNC2=C1 SWEICGMKXPNXNU-UHFFFAOYSA-N 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- OHUPFRGAUGZKCY-UHFFFAOYSA-N n-(2,5-dioxooxolan-3-yl)-2-methyl-n-octadecylpropanamide Chemical compound CCCCCCCCCCCCCCCCCCN(C(=O)C(C)C)C1CC(=O)OC1=O OHUPFRGAUGZKCY-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229940014800 succinic anhydride Drugs 0.000 description 2
- WZBIGCKKKRUVFU-UHFFFAOYSA-N 1-acetyl-6-amino-2h-indazol-3-one Chemical compound C1=C(N)C=C2N(C(=O)C)NC(=O)C2=C1 WZBIGCKKKRUVFU-UHFFFAOYSA-N 0.000 description 1
- QGDRTRXGXSQRLW-UHFFFAOYSA-N 2-[2-methylpropanoyl(octadecyl)amino]-4-oxo-4-[(3-oxoindazol-6-yl)amino]butanoic acid Chemical compound C(=O)(O)C(CC(=O)NC1=CC=C2C(N=NC2=C1)=O)N(C(C(C)C)=O)CCCCCCCCCCCCCCCCCC QGDRTRXGXSQRLW-UHFFFAOYSA-N 0.000 description 1
- HCXJFMDOHDNDCC-UHFFFAOYSA-N 5-$l^{1}-oxidanyl-3,4-dihydropyrrol-2-one Chemical group O=C1CCC(=O)[N]1 HCXJFMDOHDNDCC-UHFFFAOYSA-N 0.000 description 1
- RBLUNHLISNCJEE-UHFFFAOYSA-N 6-nitroindazol-3-one Chemical compound [O-][N+](=O)C1=CC=C2C(=O)N=NC2=C1 RBLUNHLISNCJEE-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- AFKHIUMDWUPZTP-UHFFFAOYSA-N N-(4-dodecylphenyl)-1,3-dioxo-2-benzofuran-5-carboxamide Chemical compound C(CCCCCCCCCCC)C1=CC=C(C=C1)NC(=O)C=1C=C2C(C(=O)OC2=O)=CC1 AFKHIUMDWUPZTP-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 239000000080 wetting agent Substances 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
-
- 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
- G03C7/3231—Couplers containing an indazolone ring
Definitions
- Q is either a group -NH--R wherein R is an acyl group containing a nitrogen atom to which there is attached either directly or via a phenyl group an alkyl residue of at least carbon atoms, together with a free carboxylic acid group or a group which can liberate a free carboxylic acid group or Q is a group -N (T) wherein T is an acyl group which is attached to the nitrogen atom by a cyclic imide linkage, the group T containing an alkyl residue of at least 10 carbon atoms, the ring to which Q is attached optionally containing other substituents.
- This invention relates to new indazolone magenta colour couplers Olf use in colour photographic material.
- Indazolone magenta colour couplers have been known for a number of years but have not in fact been used to any great extent in colour photographic material because most of the known indazolone colour couplers are converted in part into a yellow product when they come into contact with an oxidising medium such as the bleach bath for the removal of the silver image during the processing of colour photographic material.
- an oxidising medium such as the bleach bath for the removal of the silver image during the processing of colour photographic material.
- a yellow product is also formed in the non image areas. It is possible to prevent the occurrence of this yellow reversal image by treating the colour developed layer with a bath containing formaldehyde before the silver is removed by bleaching. This however adds another step to the processing sequence and, further, sometimes causes unwanted side effects.
- Q is either a group --NH-R wherein R is an acyl group containing a nitrogen atom to which there is attached either directly or via a phenyl group, an alkyl residue of at least 10 carbon atoms, and containing a free carboxylic acid group or a group which can liberate a free carboxylic acid group, or Q is a group -N (T) wherein T is an acyl group which is attached to the nitrogen atom by a cyclic imide linkage, the group T con- 3,733,335 Patented May 15,, 1973 "ice taining an alkyl residue of at least 10 carbon atoms, the ring to which Q is attached optionally containing other substituents.
- acyl groups containing an alkyl residue of at least 10 carbon atoms and at least one carboxylic acid or a group which can liberate a free carboxylic acid group are those derived from the acylating agents described in British Pats. Nos. 830,482, 858,564, 944,838, 997,500, 1,004,075, 1,039,452 and in British patent application No. 20,003/ 69 and which contain an alkyl group of at least 10 carbon atoms.
- the compounds of Examples 5, 6 and -8 which follow each contain a five membered cyclic inside ring and the colour couplers of Examples 2, 4, 7 and 9 which follow contain two such rings.
- These imide rings may be converted to the amic acid having a free carboxylic acid group by treatment with aqueous alkali'in the presence Olf a solvent such as a lower alcohol, for example n-propanol followed by acidification.
- the colour couplers of this invention are usually incorporated in a colloid silver halide emuslion by means of their alkali solubilising groups, i.e. as the salts of the amic acid.
- the behaviour of the imide rings may be shown thus:
- a compound of Formula I may be prepared by the reaction of a compound of the Formula II:
- the ring-numbering of the indazolone colour couplers of the present invention is as follows:
- indazolones are readily acylated in the l, 2 or 3 position and because of the different coupling behaviour of these derivatives it is necessary in the preparation of the acylamino indazolones of the present invention to minimise acylation occurring in the heterocyclic ring.
- the compound of Formula II is treated with an equimolar quantity of acylating agent at a temperature preferably not greater than 65 C.
- a readily hydrolysable group for example, an acetyl group, may be employed to protect the coupling ring of the indazolone compound before treatment with a long chain acylating agent. Subsequently the protecting group is removed by a short alkaline hydrolysis, e.g.
- the colour coupler which comprises the l-acetyl group i.e. the compound formed after acylation and before the final alkaline hydrolysis may be isolated and stored as such.
- the final hydrolysis may be conducted during the preparation of the colour coupler solution for coating because the initial step prior to coating is to dissolve the colour coupler in aqueous alkali.
- the colour couplers of Formula I are incorporated in a silver halide photographic emulsion by dissolving them in aqueous alkali and most preferably in the presence of a water miscible alcohol as well, and adding this solution to the silver halide photographic emulsion.
- the invention includes not only the new indazolone colour couplers and the methods for their preparation but also colour photographic material having a silver halide photographic emulsion layer which comprises a compound of Formula I.
- Method 2 A mixture of 9.0 parts of l-acetyl-6-[3- carboxy 3 (N n-octadecylisobutylramido)-propionamido]-3-indazolone, 22 parts of 2 N potassium hydroxide solution, 50 parts n-propanol and 20 ml. water was heated to the boil, held at the reflux for 1 minute and acidified with acetic acid to obtain a colourless precipitate. The solid was collected by filtration, washed with water and dried at 60 C. The product was boiled with 250 parts of methanol, cooled and filtered.
- the l-acetyl-6-aminoinrlazolone used here was prepared from 6-nitro indazolone by acetylation to 1:3-diacetyl-6-nitroindazolone, followed by partial hydrolysis to 1-acetyl-6-nitroindazolone and finally reduction by hydrogenation.
- a photographic layer containing the colour coupler just prepared was obtained in the following manner:
- EXAMPLE III l-acetyl-S- [3-carboxy-3- (N-n-octadecylisobutyramido) propionarnido]-3-indazoline is a'l til) (CHshCHCON-CHCHzCONH -C ⁇ A mixture of 1.91 parts of 1-acetyl-S-aminoindazolone, and 50 parts of glacial acetic acid was heated to dissolve, cooled to 60 C. and 4.37 parts of N-n-octadecylisobutyrylamino succinic anhydride was added. The whole was stirred at 60 C. for 2 hours.
- a photographic layer containing the colour coupler derived from the above compound was prepared as follows:
- N-( 3 dodecyloxyphenyl)pyromellitic mono-imide mono-anhydride used in this example was made by the method described in Example I of British patent specification No. 1,004,075 for N-( l-dodecylphenyl)pyromellitic mono-imide mono-anhydride.
- a photographic layer containing the colour coupler derived from the above compound was prepared by the method of Example HI using 1.32 parts of compound and 4.0 parts of 2 N potassium hydroxide solution.
- a photographic layer containing the colour coupler derived from the above compound was prepared by the method of Example III using 1.28 parts of compound and 3.0 parts of 2 N potassium hydroxide solution.
- a photographic layer containing the colour coupler derived from the above compound was prepared by the method of Example III using 1.24 parts of compound and 3.0 parts of 2 N potassium hydroxide solution.
- a photographic layer containing the colour coupler derived from the above compound was prepared by the method of Example III using 1.28 parts of compound and 4.0 parts of 2 N potassium hydroxide solution.
- EXAMPLE VIII l-acetyl-S- [4- 3-dodecyloxyphenylcarbamoyl) phthalimido] -3-indazolone o 0N Q-NHO 0G0 N/ can boon
- the 3.4 parts of 1 acetyl-S-[4-(3-dodecyloxyphenylcarbamoyl)phthalimido] 3 indazolone were obtained as a solid melting at 272-274 C.
- a photographic layer containing the colour coupler derived from the above compound was prepared by the method of Example III using 1.28 parts of the compound and 3.0 parts of 2 N potassium hydroxide solution.
- N-n-octadecyl-isobutrylamino succinic anhydride (4.37 parts) was then added and the mixture stirred at 50-60 C. for 2 hours. The solution obtained was allowed to stand overnight to allow crystallisation to take place. The colourless precipitate was filtered off, washed with ethanol and dried at C. The 7 bromo-S-[3-carboxy-3-(N-n-octadecylisobutyramido) propionamide]-3-indazolone (2.3 parts) was obtained as a solid melting at 182 C.
- a photographic layer containing 1.33 parts of the above coupler, prepared by the method of Example I gave a bright magenta dye image.
- a photographic layer containing the above coupler was produced by the method of Example I.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB823/70A GB1285432A (en) | 1970-01-07 | 1970-01-07 | Indazole colour couplers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3733335A true US3733335A (en) | 1973-05-15 |
Family
ID=9711105
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00104510A Expired - Lifetime US3733335A (en) | 1970-01-07 | 1971-01-06 | Indazolone magenta couplers |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3733335A (fr) |
| BE (1) | BE761237A (fr) |
| CH (1) | CH557046A (fr) |
| DE (1) | DE2100538A1 (fr) |
| GB (1) | GB1285432A (fr) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4040835A (en) * | 1974-06-27 | 1977-08-09 | Fuji Photo Film Co., Ltd. | Two-equivalent magenta couplers with amido coupling-off groups |
| US4338393A (en) * | 1980-02-26 | 1982-07-06 | Eastman Kodak Company | Heterocyclic magenta dye-forming couplers |
| US4481268A (en) * | 1981-02-09 | 1984-11-06 | Eastman Kodak Company | Method of forming a photographic dye image |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3720932B2 (ja) * | 1996-09-18 | 2005-11-30 | 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 |
-
1970
- 1970-01-07 GB GB823/70A patent/GB1285432A/en not_active Expired
-
1971
- 1971-01-05 BE BE761237A patent/BE761237A/fr unknown
- 1971-01-06 US US00104510A patent/US3733335A/en not_active Expired - Lifetime
- 1971-01-06 CH CH12171A patent/CH557046A/xx not_active IP Right Cessation
- 1971-01-07 DE DE19712100538 patent/DE2100538A1/de active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4040835A (en) * | 1974-06-27 | 1977-08-09 | Fuji Photo Film Co., Ltd. | Two-equivalent magenta couplers with amido coupling-off groups |
| US4338393A (en) * | 1980-02-26 | 1982-07-06 | Eastman Kodak Company | Heterocyclic magenta dye-forming couplers |
| US4481268A (en) * | 1981-02-09 | 1984-11-06 | Eastman Kodak Company | Method of forming a photographic dye image |
Also Published As
| Publication number | Publication date |
|---|---|
| CH557046A (de) | 1974-12-13 |
| DE2100538A1 (de) | 1971-07-22 |
| GB1285432A (en) | 1972-08-16 |
| BE761237A (fr) | 1971-06-16 |
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