US3133815A - Color photographic materials and processes - Google Patents
Color photographic materials and processes Download PDFInfo
- Publication number
- US3133815A US3133815A US52354A US5235460A US3133815A US 3133815 A US3133815 A US 3133815A US 52354 A US52354 A US 52354A US 5235460 A US5235460 A US 5235460A US 3133815 A US3133815 A US 3133815A
- Authority
- US
- United States
- Prior art keywords
- group
- color
- carboxypropionylamino
- amino
- phenyl
- 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
- 238000000034 method Methods 0.000 title claims description 25
- 239000000463 material Substances 0.000 title description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 5
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 claims description 4
- -1 ethylene, phenylene Chemical group 0.000 description 66
- 239000000839 emulsion Substances 0.000 description 21
- 125000003277 amino group Chemical group 0.000 description 19
- 150000008064 anhydrides Chemical class 0.000 description 16
- 125000000217 alkyl group Chemical group 0.000 description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 13
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 239000001257 hydrogen Substances 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 7
- ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical compound O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 6
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 6
- 125000003710 aryl alkyl group Chemical group 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 108010010803 Gelatin Proteins 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 229920000159 gelatin Polymers 0.000 description 5
- 239000008273 gelatin Substances 0.000 description 5
- 235000019322 gelatine Nutrition 0.000 description 5
- 235000011852 gelatine desserts Nutrition 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- 239000004332 silver Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical group 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- XCTQPMCULSZKLT-UHFFFAOYSA-N 2-cyano-n-phenylacetamide Chemical compound N#CCC(=O)NC1=CC=CC=C1 XCTQPMCULSZKLT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 125000005137 alkenylsulfonyl group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 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 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- UUCOGWNZGQHFFT-UHFFFAOYSA-N C(CCCCCCCCCCCCCCCCC)(=O)NC1C(=O)OC(C1)=O Chemical compound C(CCCCCCCCCCCCCCCCC)(=O)NC1C(=O)OC(C1)=O UUCOGWNZGQHFFT-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 150000003931 anilides Chemical class 0.000 description 2
- 150000003974 aralkylamines Chemical class 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 239000002585 base Substances 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
- 239000012024 dehydrating agents Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- NUTWJPPMTMHFGI-UHFFFAOYSA-N 3,4-dihydropyrazol-2-amine Chemical compound NN1CCC=N1 NUTWJPPMTMHFGI-UHFFFAOYSA-N 0.000 description 1
- CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000000732 arylene group Chemical group 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
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000002270 dispersing agent Substances 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
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- NXPHCVPFHOVZBC-UHFFFAOYSA-N hydroxylamine;sulfuric acid Chemical compound ON.OS(O)(=O)=O NXPHCVPFHOVZBC-UHFFFAOYSA-N 0.000 description 1
- RSAZYXZUJROYKR-UHFFFAOYSA-N indophenol Chemical compound C1=CC(O)=CC=C1N=C1C=CC(=O)C=C1 RSAZYXZUJROYKR-UHFFFAOYSA-N 0.000 description 1
- CBEQRNSPHCCXSH-UHFFFAOYSA-N iodine monobromide Chemical compound IBr CBEQRNSPHCCXSH-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000400 lauroyl group Chemical group O=C([*])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
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- JMQITILRHSGUCB-UHFFFAOYSA-N n-(2,5-dioxooxolan-3-yl)acetamide Chemical compound CC(=O)NC1CC(=O)OC1=O JMQITILRHSGUCB-UHFFFAOYSA-N 0.000 description 1
- YSVIOFKUOBVJII-UHFFFAOYSA-N n-(2,5-dioxooxolan-3-yl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NC1CC(=O)OC1=O YSVIOFKUOBVJII-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 150000004989 p-phenylenediamines Chemical class 0.000 description 1
- 125000000913 palmityl 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])[H] 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 230000001376 precipitating effect Effects 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
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical group O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])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
- 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
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 239000001043 yellow dye 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
- G03C7/3212—Couplers characterised by a group not in coupling site, e.g. ballast group, as far as the coupling rest is not specific
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
- C07D231/52—Oxygen atom in position 3 and nitrogen atom in position 5, or vice versa
Definitions
- color photography dye images are produced by the reaction of the oxidation products of primary amino photographic developing agents, formed by the use of such developing agents in developing silver salt images, with certain classes of organic compounds which, as the result of such action, form azomethine, indophenol or related dyes.
- the developing agents used are usually N.N-dialkyl p-phenylene diamines or simple derivatives thereof, and the organic compounds which couple with the oxidation products of those developers, formed during development, are known as color couplers. These latter may contain amino groups and fall into several classes as follows:
- a process for the production of a color photographic image which comprises subjecting a developable silver salt image to development by means of an aromatic primary amino color developing agent in the presence of a color coupler which in the form of its free acid is represented by the general formula:
- RNH-- represents the residue of a color coupler containing an amino group and either one of R and R is a hydrogen atom and the other is a group of the formula:
- RNH is the residue of a color coupler containing an amino group selected from the class consisting of (a) color couplers which contain, in addition to the amino group, a -CO-CH -CO group, (b) color couplers which contain, in addition to the amino group, a cyanacetyl group, (0) color couplers which contain in addition to the amino group a pyrazolone ring, and (d) colour couplers which contain the amino group and are phenols and l-naphthols, and either one of R and R is a hydrogen atom and the other is a group of a structure selected from the group consisting of CO N-aeyl and N/ ⁇ Z 1 13 00/ where R is selected from the class consisting of a hydrogen atom, alkyl groups containing 1 to 18 carbon atoms, cycloalkyl groups containing 5 to 10 carbon atoms, aralkyl groups of which the alkyl moiety contains 1 to 3 carbon atoms, and
- acyl groups there may be mentioned acetyl, propionyl, benzoyl, lauroyl, stearoyl, isobutyryl, caproyl, isovaleryl, ethylsulphonyl, hexadecylsulphonyl, and p-toluenesulphonyl.
- alkyl groups represented by R there may be mentioned methyl, ethyl, butyl, heptyl, dodecyl, cetyl, octadecyl, iso-butyl, iso-amyl and tert.-octyl.
- cycloalkyl groups represented by R there may be mentioned cyclopentyl, cyclohexyl, hexahydrobenzyl and cyclodecyl.
- aralkyl groups represented by R there may be mentioned benzyl, p-dodecylbenzyl, 5 benzylisopropyl, naphthyl methyl, phenyl ethyl and phenyl propyl, and as examples of aryl groups represented by R there may be mentioned phenyl, tolyl, chlorophenyl, sulphophenyl, methoxyphenyl cyanophenyl, naphthyl and dodecylphenyl.
- RNH may represent the residue of any of the specific amino color couplers which are listed above (i.e. the residue obtained by removing a hydrogen atom from the amino group), or the residue of any other amino color coupler witln'n the generic groupings specified above. It is particularly to be noted that the nature of the amino color coupler residue is not critical. Any of the types known in this art may be used. The critical feature in the applicants products is the chain referred to above which characterises the products and leads to the advantages referred to above. Nevertheless, from the standpoint of color photography in natural colors it is obviously desirable to select the amino color coupler used as starting material so that the color coupler according to the present invention is of satisfactory hue, i.e. in one of the subtractive colors, yellow, magenta and cyan.
- the aforesaid color couplers wherein R or R stands for -N.R .acyl may be prepared by reacting a color coupler containing an amino group with an anhydride of the formula:
- the reaction between the color coupler containing an amino group and the anhydride may be conveniently carried out by heating the reactants together in a suitable organic solvent, for example glacial acetic acid.
- the new color couplers may be conveniently isolated by adding Water and/or an aliphatic alcohol, for example methanol and ethanol to the solution of the color coupler in the organic solvent and filtering off the solid which is precipitated.
- an aliphatic alcohol for example methanol and ethanol
- the color coupler so obtained consists of either or both of the two isomeric compounds which are obtain-.
- the anhydrides of the above formula may be obtained by heating an amino acid of the formula:
- R has the meaning stated above with an acid chloride or an acid anhydride.
- amino acids of the above formula may themselves be obtained by treating maleic acid with ammonia, or an alkylamine or a cycloalkylamine or an aralkylamine or an arylamine.
- anhydride of the above formula may be obtained by reacting an ester of maleic acid with ammonia, or an alkylamine, or a cycloalkylamine, or an aralkylamine or an arylamine, subsequently treating with an acid chloride or an acid anhydride, hydrolysing off the ester groups and subsequently treating with a dehydrating agent, for example acetic anhydride.
- a dehydrating agent for example acetic anhydride.
- suitable anhydrides which may be used in this process of the invention there may be mentioned stearoylaminosuccinic anhydride, acetylaminosuccinic anhydride, lauroylarninosuccinic anhydride, benzoylaminosuccinic anhydride, N-benzylacetylaminosuccinic anhydride, phenylacetylarninosuccinic anhydride, butyl-isobutyrylaminosuccinic anhydride, N-cetylacetylaminosuccinic anhydride, N-n-octadecylacetylaminosuccinic anhydride, N-n-octadecylpropionylaminosuccinic anhydride, N-n-octadecyl-iso-butyrylaminosuccinic anhydride, N-noctadecyl-isovalerylammosuccinic anhydride, N-n-hexadecylbenz
- the reaction between the color coupler containing the amino group and the compound of the above formula may be conveniently carried out by heating the reactants together in a suitable organic solvent, for example glacial acetic acid, and subsequently precipitating the new color coupler by the addition of water and/or methanol and ethanol.
- a suitable organic solvent for example glacial acetic acid
- the color coupler so obtained consists of either or both of the two isomeric compounds which are obtainable by reacting the color coupler containing an amino group with a compound of the above formula.
- the compounds of the above formula may themselves be obtained by reacting aminosuccinic acid with an anhydride of an ethylene, phenylene or tetrahydrophenylene dicarboxylic acid, and subsequently treating with a dehydrating agent, for example acetic anhydride.
- a dehydrating agent for example acetic anhydride.
- Suitable compounds of the above formula which may be used in this process of the invention there may be mentioned phthalimidosuccinic anhydride.
- the color couplers containing an amino group which may be used in the production of the color couplers for use in the present invention are, for example, those listed above.
- the aforesaid color couplers may be used in the photographic developing solution used for developing a photographic emulsion, or they may be included in the photographic material, in a light-sensitive layer or in a nonlight-sensitive layer adjacent to a sensitive layer or separated therefrom by a water-permeable colloid layer.
- a light-sensitive gelatinoor gelatino-substitute silver halide emulsion layer which forms part of a multi-layer film or paper of the kind used for color photography.
- those new color couplers which contain a substituent rendering them fast to diffusion, for example an alkyl chain containing at least 12 carbon atoms.
- the new color couplers may be used in the form of their salts with an alkali metal or an organic amine.
- the multilayer color photographic material may be a natural order material in which the images are to be formed in colors complementary to those of the original object or one in which an unnatural order is used, for example one in which in the top layer there is formed a yellow image of the blue parts of the object, in one of the two lower layers there is formed a cyan image of the green parts of the object and in the other a magenta image of the red parts of the object.
- the color couplers used in the present invention have important advantages over the color couplers from which they are derived.
- a light-sensitive gelatinoor gelatino-substitute silver halide emulsion layer containing an aforesaid color coupler is exposed to light, developed in a color-forming developer, bleached and fixed, and the photographic record so formed is exposed to light, there is litle or no staining of the record due to degradation by light of unreacted color coupler residual in the layer containing the dyestufi' image.
- the invention is illustarted, but not limited, by the following examples in which the parts and percentages are by weight:
- the color formers are obtained by the reaction of A-NH with either COOH-N acyl or 0 where A, R and Z have the meanings given above.
- the color couplers are formulated in a photographic emulsion layer according to one of the following methods.
- a color developer solution containing a color developing agent which for example may be 4-amino-3-methyl-N-diethylaniline (B), 4-amino-3-methyl-N-ethyl-N-w-hydroxybutyl aniline (C) or 4amino-N-ethyl-N-hydroxyphenyl aniline (D), bleached and fixed, a magenta dye image is obtained.
- a color developing agent which for example may be 4-amino-3-methyl-N-diethylaniline (B), 4-amino-3-methyl-N-ethyl-N-w-hydroxybutyl aniline (C) or 4amino-N-ethyl-N-hydroxyphenyl aniline (D)
- color coupler does not contain a long aliphatic chain it may be incorporated in a color developer solution, for example:
- solution A parts of trisodium phosphate and 1.2 parts of hydroxylamine sulphate are dissolved in 400 parts of water
- solution B 2 parts of the color coupler are dissolved (or suspended) in parts of ethanol (B).
- B is added to solution A, solution C then being added with stirring and the volume made up to 1000 parts with water.
- No. Process Agent R R1 or R2 Where one is H 31 NH O O C H III ⁇ B 668 C 673 32 NH 0 C 1H3 III C 644 I 11C18H37 33 N ⁇ III C 644 C O CH(CH CH3 34 NHCOCnH3 III B 645 CH3O
- Y is selected from the group consisting of hydro- To 200 parts of a gelatino-silver bromide emulsion there are added 50 parts of a 5% aqueous solution of the sodium salt of 4-stearoylaminobenzoylacet-3:S-dicarboxyanilide. The blue sensitive emulsion so obtained is coated on a paper base and the coated layer dried.
- a 3% aqueous solution of gelatin is then coated on top of the blue sensitive layer to form a gelatin separation layer.
- a green sensitive emulsion obtained as described in Example 1 is then coated on top of the gelatin separation layer.
- a gelatin separation layer is then coated on top of the green sensitive emulsion layer.
- a red sensitive emulsion comprising 200 parts of a red sensitive gelatinosilver chlorobromide emulsion and 50 parts of a 5% aqueous solution of the sodium salt of l-hydroxy-4-sulpho-2-naphtho-N-octadecylamide is then coated on top of the gelatin separation layer.
- the multilayer color photographic paper so obtained is exposed to the light from a color negative, developed in a color developer containing 4-amino-3-methyl-N-diethylaniline, bleached and fixed. A color print is obtained.
- Example 36 In place of the green sensitive emulsion used in Example 35 there is used a green sensitive emulsion obtained by adding 50 parts of a 5% aqueous solution of the potassium salt of the coupler of Example 9 to 200 parts of a green sensitive gel-atino-silver chlorobnomide emulsion.
- a process for the production of a color photograph image which comprises subjecting reducible silver salt image to development by means of an aromatic primary amino-color developing agent in the presence of a color coupler of the formula gen, an alkali metal and an amine group, where R is selected from the group consisting of (a) a benzyl aceto acetanilide having the structural formula:
- color coupler is l-phenyl-3- 3- (N-n-octadecylisobutyrylamino B-carb oxypropionylamino] -pyrazolone.
- color coupler is 1-phenyl-3-[ut-(N-n-octadecylisobutyrylamino)- ,B-carboxypropionylamino]5-pyrazolone.
- color coupler is 1-phenyl-3-(5-[N-(4'-n-dodecylphenyl)acetylamino] B-carb oxypropionyl amino) 5-pyrazolone.
- color coupler is 1-phenyl-3-(ct-[N-(4'-n-dodecylphenyl)acetylamino] -,8-carboxypropionylamino 5-pyrazolone.
- a process according to claim 1 wherein the coupler is 4 methoxybenzoylacet 5 [a (N n octadecylacetylamino) [3 carboxypropionylamino] 2 methoxyanilide.
- a process according to claim 1 wherein the coupler is 4' methoxybenzoylacet 5 ⁇ u-[N-(4-n-dodecylphenyl) acetylamino] fi carhoxypropionylamino ⁇ 2 methoxyanilide.
- a photographic color developing composition which comprises an aromatic primary amino photographic developing agent and a color coupler of the formula where Y is selected from the group consisting of hydrogen, an alkali metal and an amine group, where R is se- 18 lected from the group consisting of (a) a benzyl aceto acetanilide having the structural formula;
- R is selected from the group consisting of phenyl and alkoxy phenyl and R is selected from the group consisting of phenyl, alkoxy phenyl and alkyl amino phenyl;
- R is selected from the group consisting of and R i sa phenyl group
- R is selected from the group consisting of hydrogen, halogen, alkyl and alkoxy
- R is an acyl radical selected from the group consisting of alkanyl having 1 to 18 carbon atoms, phenoyl, alkylsultonyl, alkenylsulfonyl and alkylphenylsulfonyl
- R is selected from the group consisting of hydrogen, an alkyl group, a cycloalkyl group, an aralkyl group and an aryl group
- Z is selected from the group consisting of ethylene, phenylene and tetrahydrophenylene.
- a photographic element comprising a support and 19 at least one layer of a light sensitive silver halide emulsion, containing disbursed therein a color coupler of the formula where Y is selected from the group consisting of hydrogen, an alkali metal and an amine group, where R is selected from the group consisting of (a) a benzyl aceto acetanilide having the structural formula:
- R is selected from the group consisting of NH and CONH-R NH, wherein R is selected from the group consisting of alkylene and arylene, and R is selected from the group consisting of hydrogen and halogen, and where either one of R and R is a hydrogen atom and the other is a radical selected from the group consisting of wherein R is an acyl radical selected from the group consisting of alkanyl having 1 to 18 carbon atoms, phenoyl, alkylsulfonyl, alkenylsulfonyl and alkylphenylsulfonyl, R is selected from the group consisting of hydrogen, an alkyl group, a cycloalkyl group, an aralkyl group and an aryl group and Z is selected from the group consisting of ethylene, phenylene and tetrahydrophenylene.
- R is an alkyl having at least 12 carbon atoms.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9113/57A GB830797A (en) | 1957-03-20 | 1957-03-20 | New colour couplers for use in colour photography |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3133815A true US3133815A (en) | 1964-05-19 |
Family
ID=9865609
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US52354A Expired - Lifetime US3133815A (en) | 1957-03-20 | 1960-08-29 | Color photographic materials and processes |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3133815A (en16) |
| BE (1) | BE565852A (en16) |
| DE (1) | DE1115129B (en16) |
| FR (1) | FR1202940A (en16) |
| GB (1) | GB830797A (en16) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0827021A1 (en) * | 1996-08-26 | 1998-03-04 | Konica Corporation | Silver halide color photographic light-sensitive material |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3515557A (en) * | 1965-04-12 | 1970-06-02 | Du Pont | Photographic color film and process of making same |
| WO2003106445A1 (en) * | 2002-06-12 | 2003-12-24 | Qsi Pharma A/S | Compounds and methods for controlling bacterial virulence |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2964402A (en) * | 1951-10-03 | 1960-12-13 | Gevaert Photo Prod Nv | Mono-acetyl indazolone color couplers |
-
0
- BE BE565852D patent/BE565852A/xx unknown
-
1957
- 1957-03-20 GB GB9113/57A patent/GB830797A/en not_active Expired
-
1958
- 1958-03-19 FR FR1202940D patent/FR1202940A/fr not_active Expired
- 1958-03-20 DE DEJ19128A patent/DE1115129B/de active Pending
-
1960
- 1960-08-29 US US52354A patent/US3133815A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2964402A (en) * | 1951-10-03 | 1960-12-13 | Gevaert Photo Prod Nv | Mono-acetyl indazolone color couplers |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0827021A1 (en) * | 1996-08-26 | 1998-03-04 | Konica Corporation | Silver halide color photographic light-sensitive material |
| US5945268A (en) * | 1996-08-26 | 1999-08-31 | Konica Corporation | Silver halide color photographic light-sensitive material |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1115129B (de) | 1961-10-12 |
| FR1202940A (fr) | 1960-01-14 |
| GB830797A (en) | 1960-03-23 |
| BE565852A (en16) |
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