US2865751A - 1-alkyl-3-acylamido-5-pyrazolone couplers for color photography - Google Patents
1-alkyl-3-acylamido-5-pyrazolone couplers for color photography Download PDFInfo
- Publication number
- US2865751A US2865751A US610639A US61063956A US2865751A US 2865751 A US2865751 A US 2865751A US 610639 A US610639 A US 610639A US 61063956 A US61063956 A US 61063956A US 2865751 A US2865751 A US 2865751A
- Authority
- US
- United States
- Prior art keywords
- pyrazolone
- couplers
- coupler
- alkyl
- color
- 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
- -1 SILVER HALIDE Chemical class 0.000 claims description 28
- 239000000839 emulsion Substances 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 14
- 229910052709 silver Inorganic materials 0.000 claims description 11
- 239000004332 silver Substances 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 239000010410 layer Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical compound O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 description 10
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical group O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 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 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- NEPWWHQLHRGVQL-UHFFFAOYSA-N 1-n,4-n-dimethylbenzene-1,4-diamine;hydron;chloride Chemical compound Cl.CNC1=CC=C(NC)C=C1 NEPWWHQLHRGVQL-UHFFFAOYSA-N 0.000 description 1
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical class NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 1
- QNGVNLMMEQUVQK-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C=C1 QNGVNLMMEQUVQK-UHFFFAOYSA-N 0.000 description 1
- IJJSFSXLZYFTKV-UHFFFAOYSA-N 4-n-methylbenzene-1,4-diamine;hydrochloride Chemical compound Cl.CNC1=CC=C(N)C=C1 IJJSFSXLZYFTKV-UHFFFAOYSA-N 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- YGVFIVSNVVUSCS-UHFFFAOYSA-N 5-amino-2-methyl-1h-pyrazol-3-one Chemical compound CN1NC(N)=CC1=O YGVFIVSNVVUSCS-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 101100494773 Caenorhabditis elegans ctl-2 gene Proteins 0.000 description 1
- 101100112369 Fasciola hepatica Cat-1 gene Proteins 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 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 description 1
- 235000012093 Myrtus ugni Nutrition 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- FGOFNVXHDGQVBG-UHFFFAOYSA-N N-(2-methoxyphenyl)acetamide Chemical compound COC1=CC=CC=C1NC(C)=O FGOFNVXHDGQVBG-UHFFFAOYSA-N 0.000 description 1
- 101100005271 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) cat-1 gene Proteins 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 244000061461 Tema Species 0.000 description 1
- MPLZNPZPPXERDA-UHFFFAOYSA-N [4-(diethylamino)-2-methylphenyl]azanium;chloride Chemical compound [Cl-].CC[NH+](CC)C1=CC=C(N)C(C)=C1 MPLZNPZPPXERDA-UHFFFAOYSA-N 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QFFVPLLCYGOFPU-UHFFFAOYSA-N barium chromate Chemical compound [Ba+2].[O-][Cr]([O-])(=O)=O QFFVPLLCYGOFPU-UHFFFAOYSA-N 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000001808 coupling effect Effects 0.000 description 1
- OKMQERWDFNIGLL-UHFFFAOYSA-N dodecylhydrazine Chemical compound CCCCCCCCCCCCNN OKMQERWDFNIGLL-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 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
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229960000443 hydrochloric acid Drugs 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002950 monocyclic group Chemical group 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
- 239000000025 natural resin Substances 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000005691 oxidative coupling reaction Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 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
- G03C7/36—Couplers containing compounds with active methylene groups
- G03C7/38—Couplers containing compounds with active methylene groups in rings
- G03C7/384—Couplers containing compounds with active methylene groups in rings in pyrazolone rings
Definitions
- This invention relates to 1-alkyl-3-acylamido 5-pyrazolone couplers for color photography and more particularly to such couplers in which the 3-acylamido gronp is a 3-phenoxyacylamido group and which substituents in the 1 and 3-positions of the pyrazolone nucleus confer special properties upon the coupler compounds.
- S-acyIamidQ-S-pyra-Zolone couplers for color photography have previously been described includingalimited number of 1-alkyl-3-acylamido-5-pyrazolones.
- the pyrazolone coupler compounds of the present invention are distinguished in containing a particular combination of alkyl and acylamido radicals in the 1 and 3.-po.sitions of the pyrazolone nucleus with the result that-dyes obtained from the couplers in the color development proc- C Ha-N 2 Clix-P g 2,865,751 Patented p p!
- R represents an alkyl group of from 1 to 12 carbon a om Rire e e ts a pn s a l p the benzene series such as phenyl and substituted phenyl, for example, 2,4-di-tert.-amylphenyl, 2,4-di-n-amylphenyl, n represents a positive integer of from Ito. 2, and n' represents a positive integer of from 1 to 3, R represents a hydrogen atom or lower alkyl group and m represents a positive integer from 1 to 2.
- Couplers of the invention having the above generalstructure are as follows: i
- the A max. values indicated represent the wavelength of maximum light absorption of dyes made by oxidative coupling of each coupler with the developing agent 2- amino-S-diethylamino toluene hydrochloride.
- the coupler compounds of the invention can be prepared in the following manner: 1
- the product was obtained from petroleum ether as a white powder. Yield 2.5 g. M. P. 78-80 C.
- the diacylatedzcomp'ound was hydrolyzed with 2 equivalents of sodium hydroxideirr aqueous :ethanol. at room temperature for 30 minutes.
- the reaction mixture was acidified with acetic acid, the solid product was filtered off, recrystallized from ethanol and then benzene (M. P. 78-80 C.).
- Coupler No; 7 Coupler-Twas. prepared.-in. the same manner as was coupler 4 except that 2,4-di-n-amylphenoxyacetyl chloride was used implace of.2,4-di tert.-amylphenoxyacetylchloride. It. melted at 59-61? 7 Anal. calcd. for C5 H N O C, 73.1; H, 10.2; N,..718. Found: 0.73.4; l-l,10.1;N,'7.7.
- R represents "an; alkyl' group of fr'om'l to. 30 carbonatoms. and one of the groups X and Y represents a hydrogen atom" and' the other represents an acylamido group.
- A'particular groupofth'ese benzoylacet-o-allroxyanilide couplers efiicacious for use with the above couplers ofthe' invention have the above general formula:.wherein R represents "an 'alkyl' group of from about :1 to .20 carbon. atoms andone of the" groups X' a1'1d' Y' represents a .hy, drogen'" atom" and 'the' other represents :the 'group wherein R represents .eith'era hydrogenatom or analkyl group. of vfromnabout 1 tot4 carbon atoms.
- the coupler compounds of the invention find usage in a wide variety of photographic color processes particularly wherein the couplers are dispersed in an emulsion layer such as a gelatino silver halide emulsion layer by'means of coupler solvents including cellulose esters, natural and synthetic resins and organic crystalloidal materials having a'hoiling point above .about170 C., as describedin the Mannes et al. U. S. Patent 2,304,940, granted December 15, 1942, and the Jelley et al. U. S. Patent 2,322,027, granted June 15, 1943.
- an emulsion layer such as a gelatino silver halide emulsion layer by'means of coupler solvents including cellulose esters, natural and synthetic resins and organic crystalloidal materials having a'hoiling point above .about170 C.
- the optimum quantity of coupler to use in the emulsion layer can be determined by simple experiment and will depend somewhat upon the coupling activity of the particular coupler, the silver halide content of the emulsion layer, the particular process in which I the emulsion is to be used and other factors well known in the art of emulsion making.
- the couplers are preferably present in a green-sensitive emulsion layer and the mentioned benzoylacet-o-alkoxyanilide couplers may be present in-the overlying blue-sensitive emulsion layer, a yellow filter layer intervening.
- a cyan coupler may then be present in the lower red-sensitive emulsion layer adjacent to the green-sensitive emulsion layer.
- a suitable color developing solution for this purpose is as follows:
- any color forming developer containing a primary amino group may be used.
- developers having two primary amino groups as well as those having one of the amino groups substituted or having substituents in the ring such as alkyl phenylenediamines and alkyl toluylene di-- amines.
- substituents in the ring such as alkyl phenylenediamines and alkyl toluylene di-- amines.
- These compounds are usualy used in the salt formsuch as the hydrochloride or the sulfate which are more stable than the amines themselves.
- Suitable compounds are diethyl-p phenylenediamine hydrochloride, monomethyl-p-phenylenediamine hydrochloride, dimethylp-phenylenediamine hydrochloride and Z-amino-S-diethylaminotoluene hydrochloride.
- the p-amino phenols and their substitution products may also be used where the amino group is unsubstituted. All of these developers have an unsubstituted amino group which enables the oxidation products of the developer to couple with the color forming compounds to form a dye image.
- the N- alkylsultonamido alkyl-p-phenylenediamines of U. S. Patent 2,193,015 are particularly useful as color-forming developing agents.
- the development process may be employed for the production of colored photographic images in layers of gelatin or other carriers, such as collodion, organic esters ofcellulose, or synthetic resins.
- the carrier may be supported by a transparent medium such as glass, a cellulose ester or a nontransparent reflecting medium such as paperor an opaque cellulose ester.
- the emulsion may be coatedas a single layer on the support or as superposed layers on one or both sides of the support.
- the silver halide component of the emulsion layers is not especially critical and may be, for example, silver bromoiodide, silver bromide or silver chloride, etc., depending upon the results desired.
- the emulsions which are developed in the presence of the novel couplers may consist of single-layer or differentially sensitized multilayer films.
- a multilayer color film comprising a support having thereon the silver halide emulsion layer of claim 1 sensitiveto green light and a silver halide emulsion layer sensitive to blue light containing a coupler compound having the general formula thereon the silver halide emulsion layer of claim 1 sensitive to green light and a silver halide emulsion sensitive to blue light containing a coupler compound having the general formula x Y 6-00 onto 01mg wherein R represents an alkyl group of from 1 to 20 carbon atoms and one of the groups X and Y represents a hydrogen atom and the other represents the group a hydrogen atom and an alk bon atoms.
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)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE560859D BE560859A (en)van) | 1956-09-18 | ||
| US610639A US2865751A (en) | 1956-09-18 | 1956-09-18 | 1-alkyl-3-acylamido-5-pyrazolone couplers for color photography |
| GB24403/57A GB865720A (en) | 1956-09-18 | 1957-08-01 | Improvements in photographic colour couplers |
| FR1206640D FR1206640A (fr) | 1956-09-18 | 1957-09-17 | Procédé de photographie en couleurs et nouveaux produits pour sa mise en oeuvre |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US610639A US2865751A (en) | 1956-09-18 | 1956-09-18 | 1-alkyl-3-acylamido-5-pyrazolone couplers for color photography |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2865751A true US2865751A (en) | 1958-12-23 |
Family
ID=24445846
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US610639A Expired - Lifetime US2865751A (en) | 1956-09-18 | 1956-09-18 | 1-alkyl-3-acylamido-5-pyrazolone couplers for color photography |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2865751A (en)van) |
| BE (1) | BE560859A (en)van) |
| FR (1) | FR1206640A (en)van) |
| GB (1) | GB865720A (en)van) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1147483B (de) * | 1961-09-28 | 1963-04-18 | Ferrania Spa | Photographisches Mehrschichtenmaterial mit Farbkomponenten fuer die farbige Entwicklung und Verfahren zu dessen Herstellung |
| US3110717A (en) * | 1959-08-07 | 1963-11-12 | Ilford Ltd | Pyrazolone color couplers for color photography |
| US4138258A (en) * | 1974-08-28 | 1979-02-06 | Fuji Photo Film Co., Ltd. | Multi-layered color photographic materials |
| US7183431B1 (en) * | 2005-11-29 | 2007-02-27 | General Electric Company | Dihydroxy aromatic compounds and methods for preparation |
| US20070123683A1 (en) * | 2005-11-29 | 2007-05-31 | Nagarajan Arumugam | Polymers, polymer compositions and method of preparation |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2511231A (en) * | 1949-03-26 | 1950-06-13 | Eastman Kodak Co | 1-cyanophenyl-3-acylamino-5-pyrazolone couplers for color photography |
| US2600788A (en) * | 1949-06-07 | 1952-06-17 | Eastman Kodak Co | Halogen-substituted pyrazolone couplers for color photography |
| FR1070244A (fr) * | 1952-01-31 | 1954-07-20 | Kodak Pathe | Procédé de préparation de 4-arylazo-5-pyrazolones utilisables notamment comme coupleurs colorés pour la photographie en couleurs |
| US2721798A (en) * | 1953-09-02 | 1955-10-25 | Eastman Kodak Co | Compounds containing an isophthalate group useful in photography |
-
0
- BE BE560859D patent/BE560859A/xx unknown
-
1956
- 1956-09-18 US US610639A patent/US2865751A/en not_active Expired - Lifetime
-
1957
- 1957-08-01 GB GB24403/57A patent/GB865720A/en not_active Expired
- 1957-09-17 FR FR1206640D patent/FR1206640A/fr not_active Expired
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2511231A (en) * | 1949-03-26 | 1950-06-13 | Eastman Kodak Co | 1-cyanophenyl-3-acylamino-5-pyrazolone couplers for color photography |
| US2600788A (en) * | 1949-06-07 | 1952-06-17 | Eastman Kodak Co | Halogen-substituted pyrazolone couplers for color photography |
| FR1070244A (fr) * | 1952-01-31 | 1954-07-20 | Kodak Pathe | Procédé de préparation de 4-arylazo-5-pyrazolones utilisables notamment comme coupleurs colorés pour la photographie en couleurs |
| US2721798A (en) * | 1953-09-02 | 1955-10-25 | Eastman Kodak Co | Compounds containing an isophthalate group useful in photography |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3110717A (en) * | 1959-08-07 | 1963-11-12 | Ilford Ltd | Pyrazolone color couplers for color photography |
| DE1147483B (de) * | 1961-09-28 | 1963-04-18 | Ferrania Spa | Photographisches Mehrschichtenmaterial mit Farbkomponenten fuer die farbige Entwicklung und Verfahren zu dessen Herstellung |
| US4138258A (en) * | 1974-08-28 | 1979-02-06 | Fuji Photo Film Co., Ltd. | Multi-layered color photographic materials |
| US7183431B1 (en) * | 2005-11-29 | 2007-02-27 | General Electric Company | Dihydroxy aromatic compounds and methods for preparation |
| US20070123683A1 (en) * | 2005-11-29 | 2007-05-31 | Nagarajan Arumugam | Polymers, polymer compositions and method of preparation |
| US7375177B2 (en) | 2005-11-29 | 2008-05-20 | General Electric Company | Polymers, polymer compositions and method of preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| GB865720A (en) | 1961-04-19 |
| FR1206640A (fr) | 1960-02-10 |
| BE560859A (en)van) |
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