EP0113484A1 - Coupleurs à deux équivalents formateurs de cyan et éléments photographiques les contenant - Google Patents

Coupleurs à deux équivalents formateurs de cyan et éléments photographiques les contenant Download PDF

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Publication number
EP0113484A1
EP0113484A1 EP83200020A EP83200020A EP0113484A1 EP 0113484 A1 EP0113484 A1 EP 0113484A1 EP 83200020 A EP83200020 A EP 83200020A EP 83200020 A EP83200020 A EP 83200020A EP 0113484 A1 EP0113484 A1 EP 0113484A1
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EP
European Patent Office
Prior art keywords
group
couplers
cyan
coupler
silver halide
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.)
Withdrawn
Application number
EP83200020A
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German (de)
English (en)
Inventor
Marcel Jacob Monbaliu
Paul Louis Van Meerbeeck
Raphael Karel Van Poucke
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Agfa Gevaert NV
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Agfa Gevaert NV
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Application filed by Agfa Gevaert NV filed Critical Agfa Gevaert NV
Priority to EP83200020A priority Critical patent/EP0113484A1/fr
Publication of EP0113484A1 publication Critical patent/EP0113484A1/fr
Withdrawn legal-status Critical Current

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    • 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
    • G03C7/34—Couplers containing phenols

Definitions

  • the present invention relates to novel 2-equivalent cyan-forming couplers, to the use thereof in the production of photographic colour images, and to photographic elements containing such couplers.
  • a light-sensitive photographic colour element comprising a support, red-sensitized, green-sensitized, and blue-sensitive silver halide emulsion layers, wherein upon colour development using appropriate couplers, cyan, magenta, and yellow dye images are formed in said layers, respectively.
  • the red-sensitized silver halide emulsion layers usually contains cyan-forming couplers of the phenol or naphthol type.
  • Couplers having a hydrogen atom at the active site are 4-equivalent couplers, which need 4 mol of exposed silver halide to form but 1 mol of dye. Couplers, however, which at their active site have a group that can be eliminated, are called 2-equivalent couplers.
  • the eliminable group is generally known as coupling off group.
  • the latter couplers require only 2 mol of exposed silver halide to form 1 mol of dye. This offers the great advantage that the amount of silver halide in the light-sensitive layer can be reduced, which may result in thinner light-sensitive layers and films. As a consequence of this reduction in thickness the processing time of these layers and films is shortened.
  • Dispersions of water-insoluble couplers after having been prepared in bulk for economic reasons, need to be stored for a given time and are used later on batch-wise in the production of colour elements.
  • most of the customarily used dispersions of couplers are prepared with the aid of a wetting agent and an oil-former in an aqueous colloid medium e.g. a gelatin solution and thus need to be stored in cooling chambers, which results in chilling. As a consequence, the chilled dispersions have to be remelted before addition to the silver halide emulsion.
  • Another object is to provide photographic elements containing said novel 2-equivalent cyan-forming couplers.
  • a further object is to provide photographic multilayer colour elements containing said novel 2-equivalent cyan-forming couplers.
  • Another object-of the invention is to produce a photographic colour image by development of a photographic multilayer colour element containing said novel 2-equivalent cyan-forming couplers.
  • novel phenol- or naphthol-type couplers capable of forming a cyan indoaniline dye by reaction with an oxidized aromatic primary amino developing agent, said couplers containing an ⁇ , ⁇ -fluorinated alkoxy coupling off group.
  • novel 2-equivalent cyan-forming couplers corresponding to one of the following general formulae I and II : wherein :
  • the present invention also provides a photographic element, and in particular a photographic multilayer colour element comprising at least three silver halide emulsion layers, which have been differently optically sensitized and wherein a novel coupler as set forth above is present in the red-sensitized silver halide emulsion layer or in a non-light-sensitive colloid layer in water-permeable relationship therewith.
  • R can represent a straight chain or branched chain alkyl group or a cyclic alkyl group, preferably an alkyl group having from 1 to 18 carbon atoms (e.g. methyl, ethyl, n-propyl, isopropyl, butyl, tert-butyl, pentyl, tert-pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, pentadecyl, heptadecyl, octadecyl, cyclohexyl), an aryl group (e.g.
  • phenyl, naphthyl or a 5- or 6- membered heterocyclic group
  • thiazolyl, furyl, thienyl, pyrrolyl imidazolyl, pyrazolinyl, pyrazolyl, pyridyl, pyridinyl, quinolyl, pyrimidinyl, oxazolyl, oxathienyl, thiazolinyl, triazinyl, pyranyl, pyrazolidinyl, pyrazinyl, isothiazolyl, isoxazolyl, imidazolinyl, imidazolidinyl, pyrrolinyl, piperidyl, piperazinyl, morpholinyl).
  • These groups may be substituted with one or more substituents selected from an alkyl group (e.g. methyl, ethyl, propyl, butyl, pentyl, etc.), a halogen atom (e.g. chloro, fluoro, etc.), a nitro group, a cyano'group, an aryl group (e.g. phenyl, naphthyl, etc.), an alkoxy group (e.g. methoxy, ethoxy, methoxyethoxy, 2-ethylhexyloxy, etc.), an aryloxy group (e.g.
  • an alkyl group e.g. methyl, ethyl, propyl, butyl, pentyl, etc.
  • a halogen atom e.g. chloro, fluoro, etc.
  • a nitro group e.g. chloro, fluoro, etc.
  • a cyano'group e.g
  • phenoxy 4-hydroxyphenoxy, 2,4-di-tert-pentyl- phenoxy, naphthoxy, etc.
  • a carboxy group an alkylcarbonyl group (e.g. acetyl, tetradecanoyl, etc.) an arylcarbonyl group (e.g. benzoyl, etc.), an alkoxycarbonyl group (e.g. methoxycarbonyl, benzyloxycarbonyl, etc.), an aryloxycarbonyl group (e.g. phenoxycarbonyl, p-tolyloxycarbonyl, etc.), an acyloxy group (e.g.
  • acetyl- oxy, benzoyloxy, etc. a sulphamoyl group (e.g. N-ethylsulphamoyl, 5-N-octadecyl-sulphamoyl, etc.), a carbamoyl group (e.g. N-ethylcarbamoyl, N-methyl-N-dodecylcarbamoyl, etc.), an acylamido group (e.g. acetamido, benzamido, etc.), a diacylamido group (e.g. succinimido, hydantoinyl, etc.) a ureido group (e.g.
  • alkylsulphonamido group e.g. methylsul- phonamido, dodecylsulphonamido, methoxyethylsulphonamido, etc.
  • R substituents are methyl, perfluoropropyl, and 2,4-di(2-chloro-1,1,2-trifluoro-ethoxy)phenyl.
  • the ballasting group R 3 can represent an aliphatic hydrocarbon group, which may be saturated or unsaturated and may have an unbranched chain, a branched chain, or a cyclic structure, preferably an alkyl group (e.g.
  • Preferred examples of a substituted ballasting group R 3 are 1-(3-pentadecylphenoxy)propyl, 1-[2,4-(di-tert-pentyl-)phenoxy]- propyl, 1-(4-dodecyloxyphenoxy)propyl, 3-[2,4-(di-tert-pentyl)-phenoxy]-propyl, 4-[2,4-(di-tert-pentyl)phenoxy]-butyl, 1,3-(dioctyloxy)-isopropoxy-2-chloro-5-hexadecyloxycarbonyl-phenyl, 5-(p-hexadecyloxyphenyl)-1,3-thiazole-2-yl.
  • Novel cyan-forming 2,5-diacylamino-phenol couplers that correspond to the general formula I wherein Y represents -CO- and that carry at the 4-position a 1,1,2,3,3,3-hexafluoropropoxy substituent or a 2-chloro-1,1,2-trifluoroethoxy substituent as coupling off group can be prepared according to the following reaction scheme, wherein R and R 3 have the significance as defined above :
  • Couplers corresponding to general formula I ( Y representing
  • novel cyan-forming 2-sulphonamido-5-acylamino-phenol couplers that correspond to the general formula I wherein Y represents -S0 2 -and that carry at the 4-position a 1,1,2,3,3,3-hexafluoropropoxy substituent or a 2-chloro-1,1,2-trifluoroethoxy substituent as coupling off group can be prepared as described hereinafter in detail: 2.1. 2,5-dibenzyloxy-methylsulphonylaminobenzene.
  • Phenol couplers comprising instead of the 1,1,2,3,3,3-hexafluoropropoxy coupling off group a 2-chloro-1,1,2-trifluoroethoxy coupling off group can be prepared analogously to the 2,5-diacylamino-phenol couplers comprising such a 2-chloro-1,1,2-trifluoroethoxy group, as described hereinbefore.
  • Coupler 6 55.2 g (0.070 mol) of coupler 6 was dissolved in 500 ml of acetonitrile and 15 ml of hydrazine hydrate. The resulting mixture was stirred for 2 h, left standing for 2 days, and then diluted with 1 1 of water. The precipitate was filtered off, dried, and recrystallized from ethanol.
  • novel cyan-forming 2-N-substituted carbamoyl-4-,x,a-fluorinated alkoxy-naphthols corresponding to the general formula II can be prepared according to the following reaction scheme, wherein R 3 has the significance as defined above :
  • Naphthol couplers according to the invention comprising instead of the 1,1,2,3,3,3-hexaftuoropropoxy coupling off group a 2-chioro-1,1,2-trifluoroethoxy coupling off group can be prepared as follows :
  • This product was synthesized in an analogous was as described under 3.2 hereinbefore but starting from 32 g of intermediate product (5.1.), 13,2 g of phenol, and 14 ml of phosphoryl chloride in a mixture of 300 ml of acetonitrile and 10 ml of dry dimethylformamide.
  • This product was synthesized in an analogous way as described under (3.3.), but starting from 11.5 g (0.029 mol) of intermediate product (5.2.) and 11.5 g (0.029 mol) of 3-amino-4-chlorobenzoic acid-n-hexadecyl ester.
  • the crude product was purified by recrystallization from ethanol. Yield : 14.2 g (70%) of 4-(2-chloro-1,1,2-trifluoroethoxy)-1-hydroxy-2-N-(-chloro-5-n-hexadecyloxycarbonyl- phenyl)-carbamoyl-naphthol melting at 85°C.
  • Naphthol couplers according to the invention comprising instead of a 1,1,2,3,3,3-hexafluoropropoxy or 2-chloro-1,1,2-trifluoroethoxy coupling off group a difluoromethoxy coupling off group can be prepared as follows :
  • This product was synthesized in an analogous way as described under (4.2.), but starting from 12.7 g (0.05 mol) of intermediate product (6.1.), 15.9 g (0.051 mol) of 2,4-di-tert-pentyl-aminobutyl- oxybenzene, 11 g (0.052 mol) of dicyclohexyl carbodiimide, and 150 ml of ethyl acetate.
  • the « ,d -fluorinated alkoxy coupling off group can be built in in the coupler molecule in but one step by an addition reaction. This contributes greatly to the economical accessability of the novel couplers. Moreover, the reaction sequence leading to the couplers of the present invention offers high yields.
  • the novel 2-equivalent couplers of the present invention can be dispersed successfully in water.
  • Aqueous dispersions of the couplers of the invention can be stored for long periods in normal conditions, which means that they have not to be kept in special cooling rooms.
  • the stability of the aqueous dispersions of couplers according to he present invention has proven to be excellent.
  • the afore-mentioned advantages of the aqueous dispersions of the couplers of the present invention permit the coating of layers containing small amounts of hydrophilic colloid, preferably gelatin. As a consequence of the reduced amount of colloid in the light-sensitive layers, the sharpness of the dye images formed therein is improved.
  • non-diffusing used herein with respect to couplers has the meaning commonly applied to the term in photography and means that in any practical application migration or wandering of such non-diffusing coupler compound through organic colloid layers such as gelatin layers in an alkaline medium, in the photographic elements of the invention is substantially unexisting.
  • the dispersions of the couplers for each of the colour separation images are usually incorporated into the coating composition of the differently sensitized silver halide emulsion layers.
  • the couplers can also be added to the coating composition of non-light-sensitive colloid layers that are in water-permeable relationship with the light-sensitive silver halide emulsion layers.
  • the non-diffusing cyan-forming couplers corresponding to the above general formulae can be incorporated into the coating composition of the silver halide emulsion 1ayer ° or other colloid layers in water-permeable relationship therewith according to any technique known by those skilled in the art for incorporating photographic ingredients, more particularly colour couplers, into colloid compositions.
  • the cyan-forming couplers according to the present invention can be dispersed, occasionally in the presence of a wetting or dispersing agent, in a hydrophilic composition constituting or forming part of the binding agent of the colloid layer.
  • Very suitable wetting agents that can be used to disperse the cyan-forming couplers of the invention are the fluorine-containing surface active agents of U.S. Patent Specification no. 4,292,402.
  • U.K. Patent Specifications 791,219 - 1,098,594 - 1,099,414 - 1,099,415 - 1,099,416 - 1,099,417 - 1,199,570 - 1,218,190 - 1,297,947 to the U.S. Patent Specifications 2,269,158 - 2,284,887 - 2,304,939 - 2,304,940 - 2,322,027, to the French Patent Specification 1,555,663, and to the Belgian Patent Specification 722,026.
  • the cyan-forming couplers according to the present invention can be used in conjunction with various kinds of photographic emulsions.
  • Various silver salts can be used as the light-sensitive salt.
  • silver bromide, silver iodide, silver chloride or mixed silver halides such as silver chlorobromide, silver bromoiodide, and silver chlorobromoiodide can be employed.
  • the couplers can be used in emulsions of the mixed packet type as described in the U.S. Patent Specification 2,698,794, or emulsions of the mixed grain type as described in the U.S. Patent Specification 2,592,243.
  • the colour couplers can be used with emulsions wherein latent images are formed predominantly at the surface of the silver halide crystal or with emulsions wherein latent images are formed predominantly inside the silver halide crystal.
  • the hydrophilic colloid used as the binder for the silver halide can be e.g. gelatin, colloidal albumin,, zein, casein, a cellulose derivative, a synthetic hydrophilic colloid such as polyvinyl alcohol or poly-N-vinyl pyrrolidone. If desired, compatible mixtures of two or more of these colloids can be employed for dispersing the silver halide.
  • the light-sensitive silver halide emulsions used in the manufacture of a photographic element according to the present invention can be sensitized chemically as well as optically. They can be sensitized chemically by carrying out the ripening in the presence of small amounts of sulphur-containing compounds such as allyl thiocyanate, allyl thiourea, or sodium thiosulphate.
  • the emulsions can also be sensitized by means of reducing agents e.g. tin compounds as described in the French Patent Specification 1,146,955 and in the Belgian Patent Specification 568,687, imino-aminomethane sulphinic acid compounds as described in U.K.
  • Patent Specification 789,823 and small amounts of noble metal compounds such as gold, platinum, palladium, iridium, ruthenium, and rhodium compounds. They can be sensitized optically by means of cyanine and merocyanine dyes.
  • the said emulsions can also comprise compounds that sensitize the emulsions by development acceleration e.g. compounds of the polyoxyalkylene type such as alkylene oxide condensation products as described i.a. in U.S. Patent Specifications 2,531,832, 2,533,990, and 4,292,400 in U.K. Patent Specifications 920,637 - 940,051 - 945,340 - 991,608 and 1,091,705 and onium derivatives of amino-N-oxides as described in U.K.Patent Specification 1,121,696.
  • development acceleration e.g. compounds of the polyoxyalkylene type such as alkylene oxide condensation products as described i.a. in U.S. Patent Specifications 2,531,832, 2,533,990, and 4,292,400 in U.K. Patent Specifications 920,637 - 940,051 - 945,340 - 991,608 and 1,091,705 and onium derivatives of amino-N-oxides as described
  • the emulsions may comprise stabilizers e.g. heterocyclic nitrogen-containing thioxo compounds such as benzothiazoline-2-thione and 1-pheny1-2-tetrazo1ine-5-thione and compounds of the hydroxytriazolopyrimidine type. They can also be stabilized with mercury compounds such as the mercury compounds described in Belgian Patent Specifications 524,121 - 677,337, and in the U.K. Patent Specification 1,173,609.
  • stabilizers e.g. heterocyclic nitrogen-containing thioxo compounds such as benzothiazoline-2-thione and 1-pheny1-2-tetrazo1ine-5-thione and compounds of the hydroxytriazolopyrimidine type.
  • mercury compounds such as the mercury compounds described in Belgian Patent Specifications 524,121 - 677,337, and in the U.K. Patent Specification 1,173,609.
  • the light-sensitive emulsions containing the couplers of the present invention may also comprise any other kind of ingredient such as those described for such emulsions in Research Disclosure no. 17643 of December 1978, in particular development-inhibitor-releasing compounds and competing couplers. Such compounds and couplers can be incorporated in layers in water-permeable relationship with the emulsion layers containing the couplers of the present invention.
  • the non-diffusing cyan-forming couplers of the present invention are usually incorporated into a red-sensitized silver halide emulsion of the photographic multilayer colour element.
  • Such photographic multilayer colour element usually comprises the cyan-forming coupler in (a) red-sensitized silver halide emulsion layer(s), the magenta-forming coupler in (a) green-sensitized silver halide emulsion layer(s), and the yellow-forming coupler in (a) blue-sensitive silver halide emulsion layer(s).
  • emulsions can be coated on a wide variety of photographic emulsion supports.
  • Typical supports include cellulose ester film, e.g. cellulose triacetate film, polyvinylacetal film, polystyrene film, polyethylene terephthalate film and related films or resinous materials, as well as paper or coated paper e.g. polyethylene-coated paper, and glass.
  • an exposed silver halide emulsion layer is developed with an aromatic primary amino developing agent in the presence of a cyan-forming coupler according to the present invention.
  • All colour developing agents capable of forming a cyan indoaniline dye with the cyan-forming couplers according to the invention can be utilized as developers.
  • Suitable developing agents are aromatic compounds in particular p-phenylenediamine and derivatives thereof, e.g.
  • N,N-dialkyl-p-phenylenediamines N,N-dialkyl-N'-sulphomethyl-p-phenylenediamines, N,N-dialkyl-N'-carboxymethyl-p-phenylenediamines, the sulphonamido- substituted p-phenylenediamines disclosed in US P 2,548,574 and other substituted p-phenylenediamines disclosed in US P 2,566,271.
  • p-phenylenediamines are N,N-diethyl- p-phenylenediamine, 2-amino-5-diethylaminotoluene, N-butyl-N-sulpho- butyl-p-phenylenediamine, 2-amino-5-[-N-ethyl-N-(B-methylsulphonami- do)-ethyl]-aminotoluene, N-ethyl-N-B-hydroxyethyl-p-phenylenediamine, etc.
  • These developing agents are often used in their salt form e.g. as hydrochloride or sulphate.
  • the dispersability of the 2-equivalent cyan-forming couplers comprising an ⁇ , ⁇ -fluorinated alkoxy-coupling off group according to the present invention was compared with that of analogous cyan-forming couplers differing from the couplers of the present invention only in that they comprise known coupling off groups.
  • the average size of the dispersed coupler particles was determined with the COULTER (registered trade mark) NANO-SIZER marketed by Coulter Electronics Ltd., Coldharbour Lane, Harpenden, Hertfordshire, AL 54 UN, United Kingdom.
  • the measuring principles used in this instrument are those of Brownian Motion and autocorrelation spectroscopy of scattered laser light.
  • the frequency of this Brownian Motion is inversely related to particle size.
  • the instrument also computes a polydispersity index, which is a measure of the width of the size distribution. For instance an index of 0 or 1 would describe an essentially monosized distribution, whereas 8 or 9 would describe a wide range distribution.
  • the 5 tested phenol couplers all corresponded to the following structural formula : wherein X represents hydrogen, chloro, and methoxy (for the 3 comparison phenol couplers A, B, and C respectively) as well as 2-chloro-1,1,2- trifluoroethoxy and 1,1,2,3,3,3-hexafluoropropoxy (for the couplers 3 and 5 according to the invention respectively).
  • the 6 tested naphthol couplers listed in table 3 corresponded to the following structural formula : wherein Y represents hydrogen, chloro, 2-p-methylphenylsulphonyl- ethoxy, and N-methoxyethyl-carbamoylmethoxy (for the 4 comparison naphthol couplers D, E, F, and G respectively) as well 1,1,2,3,3,3,- hexafluoropropoxy and 2-chlaro-1,1,2-trifluoroethoxy (for the couplers 18 and 24 according to the invention).
  • Each of the resulting dispersions was added to a red-sensitized silver halide emulsion.
  • Each of the emulsions was coated on film support in a ratio of 150 g per sq.m. Each emulsion layer was dried and covered with a gelatin antistress layer. The dried light-sensitive elements were exposed in a Herrnfeld sensitometer for 1/20th second through a continuous wedge with a constant of 0.30. The exposed elements were colour-developed for 10 min at 24°C with a developer containing as developing agent 2-amino-5-diethylamino-toluene hydrochloride (CD-2), then bleached, fixed, and washed in the conventional way.
  • CD-2 2-amino-5-diethylamino-toluene hydrochloride
  • Table 4 shows the results of speed, gradation and maximum density (Dmax) obtained with both processed elements, the first of which comprising 2-perfluorobutyroylamino-4-chloro-5-di-n-octyloxyiso- propoxycarbonamido-phenol as comparison coupler H, the second element comprising the phenol coupler 7 according to the present invention.
  • the speed was measured at 0.2 above fog.
  • the values given for the speed are relative values, a value of 100 being given to the element containing the comparison coupler H, the value 200 corresponding to a doubling of the speed.
  • a dispersion of each of the cyan-forming couplers listed in table 5 hereinafter was prepared as described in example 1 hereinbefore.
  • Each of the resulting dispersions was added to a red-sensitized silver halide emulsion prepared as described in example 2 hereinbefore.
  • Table 5 shows the results of speed, gradation and maximum density obtained with the 6 processed elements, all of them comprising a different cyan-forming 2-N-di-tert-pentylphenoxybutyl-carbamoyl- naphthol coupler, the difference between these couplers residing only in their coupling off group. These different coupling off groups are indicated in table 5.
  • Example 2 For the understanding of the values there can be referred to the explanation given in Example 2.
  • a dispersion of each of the cyan-forming couplers listed in table 6 hereinafter was prepared as described in example 1 hereinbefore.
  • Each of the resulting dispersions was added to a red-sensitized silver halide emulsion prepared as described in example 2 hereinbefore.
  • Table 6 shows the results of speed, gradation and maximum density obtained with the 3 processed elements, all of them comprising a different cyan-forming N-hexadecylcarbamoyl-naphthol coupler, the difference between these couplers residing only in their coupling off group. These coupling off groups are indicated in table 6.

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  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
EP83200020A 1983-01-10 1983-01-10 Coupleurs à deux équivalents formateurs de cyan et éléments photographiques les contenant Withdrawn EP0113484A1 (fr)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0193051A3 (en) * 1985-03-01 1987-05-27 Minnesota Mining And Manufacturing Company 2-equivalent cyan dye-forming 5-hydroxy-6-acylamino-benzoxazole-2-one couplers, silver halide photographic elements and processes employing them
EP1951662A4 (fr) * 2005-11-24 2013-10-16 3M Innovative Properties Co Agents de surface fluores pour une utilisation dans la fabrication d'un fluoropolymere
CN114057591A (zh) * 2022-01-14 2022-02-18 苏州开元民生科技股份有限公司 一种高纯度3-氨基-4-氯苯甲酸十六酯的合成方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2626315A1 (de) * 1975-06-11 1976-12-23 Fuji Photo Film Co Ltd Photographischer blaugruen-farbkuppler und dessen verwendung in einem lichtempfindlichen photographischen material zur erzeugung von farbphotographischen bildern

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2626315A1 (de) * 1975-06-11 1976-12-23 Fuji Photo Film Co Ltd Photographischer blaugruen-farbkuppler und dessen verwendung in einem lichtempfindlichen photographischen material zur erzeugung von farbphotographischen bildern

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0193051A3 (en) * 1985-03-01 1987-05-27 Minnesota Mining And Manufacturing Company 2-equivalent cyan dye-forming 5-hydroxy-6-acylamino-benzoxazole-2-one couplers, silver halide photographic elements and processes employing them
EP1951662A4 (fr) * 2005-11-24 2013-10-16 3M Innovative Properties Co Agents de surface fluores pour une utilisation dans la fabrication d'un fluoropolymere
CN114057591A (zh) * 2022-01-14 2022-02-18 苏州开元民生科技股份有限公司 一种高纯度3-氨基-4-氯苯甲酸十六酯的合成方法
CN114057591B (zh) * 2022-01-14 2022-04-05 苏州开元民生科技股份有限公司 一种3-氨基-4-氯苯甲酸十六酯的合成方法

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