US3558319A - Color photographic silver halide emulsion containing magenta couplers - Google Patents

Color photographic silver halide emulsion containing magenta couplers Download PDF

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US3558319A
US3558319A US652891A US3558319DA US3558319A US 3558319 A US3558319 A US 3558319A US 652891 A US652891 A US 652891A US 3558319D A US3558319D A US 3558319DA US 3558319 A US3558319 A US 3558319A
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compound
coupler
mixture
silver halide
color
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Tsutomu Hamaoka
Kazuya Sano
Makoto Yoshida
Yasushi Oishi
Takeshi Hirose
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Fujifilm Holdings Corp
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Fuji Photo Film Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/48—Two nitrogen atoms
    • C07D251/52—Two nitrogen atoms with an oxygen or sulfur atom attached to the third ring carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • 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

  • the present invention relates to color photography, and particularly to color photographic materials containing -pyrazolone couplers that carry ortho-substituted phenyl groups at position 1 and m-acylaminophenyl-ureido groups at position 3 of the pyraziolone nuclei.
  • magenta-colored image is produced by the oxidative coupling of a 5-pyrazolone and a p-phenylenediamine, in particular an N,Ndalkylp-phenylene (ortolylene-l-diamine.
  • the magneta image contributes greenlight absorption on the spectral region of 500 to 600 mp.. It is desired thatthe extinction be large in this region and small outside of this region, that is, in the blue and red regions.
  • the azomethine dye derived from a pyrazolone coupler has a second A.absorption maximum around 440 ma, together with the main absorption maximum near 550
  • the former is a serious obstruction to desirable color production of the blue color. This has led to many attempts to sol-ve the problem, and U.S. Pat. No. 2,369,489, which relates to ya 3-acylamino-5-pyrazolone, has brought about a considerable but by uo means quite satisfactory improvement.
  • the coupler must have a sufficient coupling activity toward p-phenylenediamine developers in order that the exposed photographic emulsion show high sensitively and high gradation and rapid development. It has hitherto been known that 1-aryl-3-acylamino-S-pyrazolone couplers provide fairly good absorption characteristics, while their coupling activities are usually low and hardly yield enough color density. On the contrary, the use of a coupler with excessively high coupling activity leads to color images of poor quality and increased fog. Thus, it is another object of this invention to provide color couplers that have enough, but not excessive, coupling activity.
  • a third requirement of the couplers relates to the fastness of the dye derived therefrom.
  • the magenta color image produced through conventional color development has a tendency to fade or discolor when exposed to light, heat or humidity.
  • the coupler that has survived the development process is apt to form yellow stains during storage.
  • a coupler is dissolved in an organic solvent and the solution is dispersed in an aqueous medium to form ne colloidal particles, before being added into the photographic emulsion, and
  • a coupler melt is directly dispersed into a photographic emulsion or is dispersed in an aqueous medium before being added to the emulsion.
  • the second process has been known to give better absorption characteristics and faster image dyes.
  • the coupler is dissolved in the smallest possible amount of solvent to secure a high level of photographic properties in the emulsion, high quality of the dye image, and good mechanical properties of the emulsion layers. This necessarily requires a high solubility of the coupler in the solvent in question.
  • 1aryl3arylureido S-pyrazolone is not very easily soluble in such non-polar solvents as are conventionally used, lalthough it has excellent absorption characteristics. Therefore, it is a fourth object of this invention to provide easily soluble l-phenyl- 3-aryl-ureido-S-pyrazolones.
  • RCO represents an acyl group having 18 to 25 carbon atoms and Ar represents a phenyl group having at least one substituent lat the ortho position, the suhstituent being chosen from the class consisting of halogens, lower alkyl groups and lower alkoxy groups.
  • the RCO group contributes the solubility of the coupler as well as its resistance to ditusion. If the RCO group carries less than 18 carbon atoms, the coupler wanders out of the layer because of the low solubility in the organic solvent and low diffusion-resistance, resulting in a worsened color reproduction. On the other hand, an excessively large RCO group, having more than 25 carbon atoms, brings about an excessively large molecular weight and thus too small an extinction per volume. Moreover the dispersion force due to this part of the molecule reduces the solubility of the coupler.
  • the RCO group is most suitably located meta to the ureido group since the compound of this location provides a higher solubility than its isomers. For example, the para isomer gives the dye of the absorption characteristics as excellent as the meta isomer but cannot be employed owing to its low solubility. This feature is well illustrated in Table 1.
  • the RCO group is preferably a substituted or an unsubstituted aliphatic acyl group or one of the following:
  • R1 represents a hydrogen atom or an alkyl group having not more than 3 carbon atoms
  • R2 represents an alkyl group having not more than carbon atoms
  • R3 represents an alkyl group having from 5 to 16 carbon atoms
  • n is an integer from 1 to 5.
  • the ortho substituent of the Ar group is quite important because the lack of the substituent gives rise to too low a solubility, and an excessive coupling activity, which leads to fogging, and thus, to worsening of the image quality.
  • the elfect of the ortho substituent is believed to be due to loss of the co-planarity of the pyrazolone and the aryl nuclei, which are affected by many kinds of substituents, such as halogens, alkyl groups and alkoxyl groups. These substituents are also effective in preventing the yellowing of the couplers by light. In particular, those that carry two substituents at the ortho positions are remarkably resistant to the action of light.
  • FIGS. 1, 2 and 3 show the spectral absorption curves of dye images obtained by processing couplers I, IV and 1X with 2-amino-5-diethylaminotoluene compared with those from the corresponding reference couplers.
  • Curves a and b of FIG. 1, c and d of FIG. 2 and e and f of FIG. 3 correspond to couplers I, A, 1V, B, IX and H, respectively.
  • magenta color image obtained from the color photographic material containing the coupler of this invention fades only reluctantly by the action of light, heat and environmental humidity, as is shown in Example 4, and the remaining coupler scarcely yellows when exposed to strong radiation. This makes this invention especially valuable from the viewpoint of image preservation.
  • the coupler of this invention gives high sensitivity and desirable gradation to the photographic emulsion, while giving rise to little fogging owing to its moderate couplng activity.
  • the present coupler shows a high rate of conversion to azomethine dyes and thus increases the sensitivity even more. This results in a smaller amount of coupler needed, and thus, in a thinner emulsion layer, which improves the image quality and the rate of development.
  • the coupler of this invention has a high solubility in such organic solvents as di-n-butyl phthalate and ethyl acetate. In other words, only a small amount of solvent is needed to disperse this kind of coupler. This necessarily simplifies the production of the photographic material. ⁇ It also excludes the need for a thick layer, guaranteeing higher quality of the image, a higher development' rate, and better mechanical properties of the emulsion layer.
  • Table 1 shows the solubilities and melting points of couplers I, V, IX and X, together with those of reference couplers C.1D.F. and B, which have structures similar to couplers I, V, IX and X, respectively.
  • the solubility has been designated as the amount of ethyl acetate needed to dissolve 1 part of the coupler at 60 C. It should be noted that a smaller value corresponds to a higher solubility.
  • dyes from the couplers of this invention give absorption characteristics suited for the subtractive color process.
  • Table 2 illustrates the absorption characteristics of ethyl acetate of dyes obtained by the oxidative coupling of the couplers of this invention with 2amino5-N,Ndi ethylaminotoluene along with those from the corresponding reference couplers.
  • Couplers of the invention Reference couplers I V A B E G J K Primary absorption max. wave length (mit) 534 541 525 535 537 519 541 539 Secondary absorption max. wave length (mp 433 431 441 438 435 445 431 438 B-value 0. 14 0. 13 0. 21 0. 17 0. l6 0. 46 0. 17 0. 17 W-value (mit) 74 76 79 78 75 78 79 80 S-value 0. 2l 0. 19 0. 26 0. 22 0 29 0. 35 0. 24 0. 24
  • couplers of the present invention are especially suited for color photography because of unusually small B- (second absorption) and S-(red absorption) values while maintaining moderate W-values.
  • step (d) 'Synthesis of Compound I.-A mixture of 15 g. of the amine obtained in step (c), 4.5 g. of sodium acetate and 2160 ml. of glacial acetic acid was warmed to 50-60 C., while stirring and into the solution was gradually added a solution of 14.5 g. of 2,4-di-t-amylphenoxyacetyl chloride in 75 ml. of glacial acetic acid. The mixture'was allowed to react for 2 hours at this temperature.
  • a sodium methylate solution prepared from 42 g. of sodium metal and 600 m1. of methanol maintained at 10 C. -Was added to the system. The solution was stirred for 90 more minutes at room temperature. Then, the reaction mixture was poured into 3 liters of cold Water. After neutralization with acetic acid, the product was extracted with ethyl acetate and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the remaining syrup was washed with hexane and digested with ether until it crystallized. It was recrystallized from ethyl acetate to give 64 g. of the pyrazolone melting at 166 C.
  • step (c) Reduction of the nitro group-The whole amount of the nitro compound prepared by step (b) was re- 1 1 Jerusalem as in step (c) of the preparation of Compound I.
  • the product thus obtained was recrystallized from a solvent mixture of acetonitrile and ethanol (1:1) containing a small amount of methyl Cellosolve to give 7.2 g. of the amine melting at 190 C.
  • the aminopyrazolone used here had been prepared by the reaction of 2,6-dichloro-4-methylphenylhydrazine with ethyl -amino--ethoxy-propionate in a similar way as step (a) of the preparation of Compound VI followed by recrystallization of the product from acetonitrile.
  • step (b) Reduction of the nitro compound-In the mixture of 500 ml. of methanol, 500 ml. of glacial acetic acid and 50 ml. of water were suspended 50 g. of the nitro compound obtained in step (a) and reduced with iron powder according to step (c) of the preparation of Compound I.
  • the product was recrystallized from the mixture of 2 parts of lmethanol and 1 part of acetonitrile to give 23 g. of the amino compound melting at 225 C.
  • This invention can be satisfactorily applied to many types of light-sensitive materials, for example, color-printing papers, positive color films, negative color films,
  • this invention is expected to be applicable not only to so-called multilayer color photographic materials, but also to so-called mixed grain type ones.
  • the invention will further be explained by the following examples.
  • EXAMPLE 1 A solution prepared by warming to 70 C. a mixture of l5 g. of Compound I, 30 g. of di-n-butyl phthalate and 20 ml. of butyl acetate was added to 300 ml. of an aqueous solution of 1.0 g. of sodium dodecylbenzenesulfonate and 25 g. of gelatin. The mixture was stirred for 30 minutes in a homogenizer, and the whole amount of the mixture was mixed with 500 g. of a green-sensitive photographic emulsion.
  • the coating contained 5.8% X 10-3 mole of silver iodobromide and 7.2)(10-4 mole of the coupler per square meter.
  • the lm was exposed and subjected to the following processing steps to yield a clear magenta image with an absorption maximum at 551 mit.
  • the spectral absorption curve has been shown in FIG. 1 by curve a.
  • EXAMPLE 2 A solution prepared by warming to 70 C. a mixture of l g. of Compound X, 30 g. of tricresyl phosphate, and 10 ml. of ethyl acetate was added to 100 ml. of an aqueous Solution containing 0.5 g. of sodium dodecyl sulfate and 7 g. of gelatin at 60 C., and the resulting mixture was stirred vigorously by means of an homogenizer to disperse the coupler nely together with the solvent.
  • the Whole amount of the emulsion thus obtained was added to 540 g. of a green-sensitive photographic emulsion. After addition of 30 ml. of 3% acetone solution of triethylenephosphoramide as a hardening agent and 7 g. of polyvinyl pyrrolidone, the resulting composition was applied to baryta paper as the middle layer to a dry-thickness of 4 104 cm. Its bottom layer was a ⁇ blue-sensitive photographic emulsion layer containing an emulsifed dispersion of coupler (L) having the following structure. On the middle layer thus formed was coated as the top layer a red-sensitive emulsion containing an emulsied dispersion of coupler (M) shown below.
  • the whole amount of the coupler-containing emulsied dispersion was mixed with 200 g. of a photographic emulsion. After addition of ml. of a 3% acetone solution of triethylene phosphoramide as a hardening agent, the mixture was applied to a cellulose triacetate film to a dry-thickness of 6 10f4 cm. and dried. In this case, the coating contained 7.2X104 mol coupler and 5.8X10f3 mol silver iodobromide per square meter. The film was exposed to graduated intensities of light with aid of a sensitometer and developed for 6 minutes at 24 C. in a developer of the following composition and then washed with water for l5 minutes at the same temperature; then it was exposed uniformly to white light and colordeveloped as described in Example 1.
  • the reversal magenta color image thus obtained had an absorption maximum at 554 mp..
  • the spectral absorption curve has been shown in FIG. 3 of the attached drawing as curve e.
  • the coating contained 7.2 10*4 mol coupler and 5.8)(10-3 mol silver iodobromide per square meter.
  • the films were exposed to graduated intensities of light by means of a sensitometer and processed in the same manner as Example 1. Their photographic properties are as follows:
  • Film (P), (Coupler IV) according to the present invention gives a high sensitivity, a high gamma and a high maximum density compared with those of Film Q containing the conventional coupler (B), and that the color image 0btained is markedly fast to light, heat and humidity. Moreover, even intense radiation did not cause yellowing due to the remaining coupler.
  • a color photographic silver halide emulsion as 13 A color photographic silver halide emulsion as defined in claim 1 where the compound is: defined in claim 1 where the compound is:
  • JH2 defined in claim 1 where the compound is: N /C 0 nernoHuQ-oomooNH-Q C1 terLCsHu llIHooNH-C--CH C
  • 0 30 ⁇ N/ References Cited l UNITED STATES PATENTS C1' CH 3,393,071 7/1968 Monbaliu et a1. 96-100 3,462,270 8/1969 Eynde et al 96-100 H J. TRAVIS BROWN, Primary Examiner U.S. Cl. X.R. 96-74; 260-310

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US652891A 1966-07-13 1967-07-12 Color photographic silver halide emulsion containing magenta couplers Expired - Lifetime US3558319A (en)

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JP4581466 1966-07-13
DED0050618 1966-07-19
DED0051843 1966-12-22

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AT (2) AT286998B (xx)
BE (2) BE701268A (xx)
CH (2) CH507263A (xx)
DE (2) DE1670529C3 (xx)
FR (1) FR7305M (xx)
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Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3844794A (en) * 1969-06-13 1974-10-29 Minnesota Mining & Mfg Magenta couplers
US3861923A (en) * 1972-05-31 1975-01-21 Fuji Photo Film Co Ltd Silver halide color photographic materials containing a 3-ureido-5-pyrazolone coupler and an aldehyde compound
US3939176A (en) * 1972-07-03 1976-02-17 Minnesota Mining And Manufacturing Company Magenta couplers
US3992404A (en) * 1973-04-17 1976-11-16 Bayer Aktiengesellschaft Pyrazol-5-ones
US4000294A (en) * 1973-04-17 1976-12-28 Bayer Aktiengesellschaft Pyrazol-5-ones
US4005215A (en) * 1973-04-17 1977-01-25 Bayer Aktiengesellschaft Pyrazol-5-ones
US4032646A (en) * 1973-04-17 1977-06-28 Bayer Aktiengesellschaft Pyrazol-5-ones
US4045571A (en) * 1973-04-17 1977-08-30 Bayer Aktiengesellschaft Pyrazol-5-ones
US4053621A (en) * 1974-06-06 1977-10-11 Bayer Aktiengesellschaft 1-[2-(βNaphthyloxy)ethyl]-3-methylpyrazolone-(5) and antithrombotic and antithrombolytic compositions and methods utilizing them
US4056533A (en) * 1973-04-17 1977-11-01 Bayer Aktiengesellschaft Pyrazol-5-ones
US4061653A (en) * 1972-06-23 1977-12-06 Bayer Aktiengesellschaft 1-Substituted-3-amino-pyrazol-5-ones
US4069334A (en) * 1973-12-20 1978-01-17 Bayer Aktiengesellschaft Pyrazole derivatives
US4081596A (en) * 1973-04-17 1978-03-28 Bayer Aktiengesellschaft Pyrazol-5-ones
USRE30420E (en) * 1973-04-17 1980-10-21 Bayer Aktiengesellschaft Pyrazol-5-ones
US4288446A (en) * 1973-04-17 1981-09-08 Bayer Aktiengesellschaft Pyrazol-5-ones
EP0112162A2 (en) 1982-12-13 1984-06-27 Konica Corporation Light-sensitive silver halide photographic material
EP0124795A2 (en) 1983-04-11 1984-11-14 Fuji Photo Film Co., Ltd. Silver halide photographic emulsion
EP0147854A2 (en) 1983-12-29 1985-07-10 Fuji Photo Film Co., Ltd. Silver halide photographic light-sensitive materials
EP0202616A2 (en) 1985-05-16 1986-11-26 Konica Corporation Method for color-developing a silver halide photographic light-sensitive material
EP0204530A2 (en) 1985-05-31 1986-12-10 Konica Corporation Method for forming direct positive color image
EP0228914A2 (en) 1985-12-28 1987-07-15 Konica Corporation Method of processing lightsensitive silver halide color photographic material
US5252446A (en) * 1991-09-25 1993-10-12 Konica Corporation Silver halide color photographic light-sensitive material comprising a 1-pentachlorinated phenyl-5-pyrazolone coupler and specific red sensitizing dyes
US5275926A (en) * 1991-09-25 1994-01-04 Konica Corporation Silver halide color photographic light-sensitive material
US5354646A (en) * 1986-03-26 1994-10-11 Konishiroku Photo Industry Co., Ltd. Method capable of rapidly processing a silver halide color photographic light-sensitive material
EP0711804A2 (de) 1994-11-14 1996-05-15 Ciba-Geigy Ag Kryptolichtschutzmittel
EP0782044A1 (en) 1995-12-27 1997-07-02 Konica Corporation Silver halide light-sensitive color photographic material

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IT1052501B (it) * 1975-12-04 1981-07-20 Chimosa Chimica Organica Spa Composti politriazinici utilizzabili per la stabilizzazione di polimeri sintetici e procedimento per la loro preparazione
US5216136A (en) * 1988-08-01 1993-06-01 Sandoz Ltd. Fiber-reactive disazo dyes containing piperazino linking radicals and processes of dyeing therewith
WO2004052862A1 (ja) 2002-12-10 2004-06-24 Ono Pharmaceutical Co., Ltd. 含窒素複素環化合物およびその医薬用途
WO2005112938A2 (en) * 2004-04-13 2005-12-01 Synta Pharmaceuticals Corp. Disalt inhibitors of il-12 production
HUE030368T2 (en) 2010-07-20 2017-05-29 Vestaron Corp Insecticide triazines and pyrimidines
WO2014159993A1 (en) * 2013-03-13 2014-10-02 The United States Of America, As Represented By The Secretary Of The Army, On Behalf Of The Walter Reed Army Institute Of Research Triazine compounds and compositions thereof and methods for treating malaria and chemoprophylaxis

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US3086855A (en) * 1958-11-05 1963-04-23 Geigy Ag J R Herbicidal compositions and method
CH448113A (de) * 1960-07-21 1967-12-15 Ciba Geigy Verfahren zur Herstellung neuer Triazine
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CH441351A (de) * 1964-06-02 1967-08-15 Geigy Ag J R Verfahren zur Herstellung N2-substituierter 2,4,6-Triamino-1,3,5-triazine

Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3844794A (en) * 1969-06-13 1974-10-29 Minnesota Mining & Mfg Magenta couplers
US3861923A (en) * 1972-05-31 1975-01-21 Fuji Photo Film Co Ltd Silver halide color photographic materials containing a 3-ureido-5-pyrazolone coupler and an aldehyde compound
US4061653A (en) * 1972-06-23 1977-12-06 Bayer Aktiengesellschaft 1-Substituted-3-amino-pyrazol-5-ones
US3939176A (en) * 1972-07-03 1976-02-17 Minnesota Mining And Manufacturing Company Magenta couplers
US4081596A (en) * 1973-04-17 1978-03-28 Bayer Aktiengesellschaft Pyrazol-5-ones
US4005215A (en) * 1973-04-17 1977-01-25 Bayer Aktiengesellschaft Pyrazol-5-ones
US4032646A (en) * 1973-04-17 1977-06-28 Bayer Aktiengesellschaft Pyrazol-5-ones
US4045571A (en) * 1973-04-17 1977-08-30 Bayer Aktiengesellschaft Pyrazol-5-ones
US4056533A (en) * 1973-04-17 1977-11-01 Bayer Aktiengesellschaft Pyrazol-5-ones
US4000294A (en) * 1973-04-17 1976-12-28 Bayer Aktiengesellschaft Pyrazol-5-ones
US3992404A (en) * 1973-04-17 1976-11-16 Bayer Aktiengesellschaft Pyrazol-5-ones
USRE30420E (en) * 1973-04-17 1980-10-21 Bayer Aktiengesellschaft Pyrazol-5-ones
US4288446A (en) * 1973-04-17 1981-09-08 Bayer Aktiengesellschaft Pyrazol-5-ones
US4069334A (en) * 1973-12-20 1978-01-17 Bayer Aktiengesellschaft Pyrazole derivatives
US4053621A (en) * 1974-06-06 1977-10-11 Bayer Aktiengesellschaft 1-[2-(βNaphthyloxy)ethyl]-3-methylpyrazolone-(5) and antithrombotic and antithrombolytic compositions and methods utilizing them
EP0112162A2 (en) 1982-12-13 1984-06-27 Konica Corporation Light-sensitive silver halide photographic material
EP0124795A2 (en) 1983-04-11 1984-11-14 Fuji Photo Film Co., Ltd. Silver halide photographic emulsion
EP0147854A2 (en) 1983-12-29 1985-07-10 Fuji Photo Film Co., Ltd. Silver halide photographic light-sensitive materials
EP0202616A2 (en) 1985-05-16 1986-11-26 Konica Corporation Method for color-developing a silver halide photographic light-sensitive material
EP0204530A2 (en) 1985-05-31 1986-12-10 Konica Corporation Method for forming direct positive color image
EP0228914A2 (en) 1985-12-28 1987-07-15 Konica Corporation Method of processing lightsensitive silver halide color photographic material
US5354646A (en) * 1986-03-26 1994-10-11 Konishiroku Photo Industry Co., Ltd. Method capable of rapidly processing a silver halide color photographic light-sensitive material
US5252446A (en) * 1991-09-25 1993-10-12 Konica Corporation Silver halide color photographic light-sensitive material comprising a 1-pentachlorinated phenyl-5-pyrazolone coupler and specific red sensitizing dyes
US5275926A (en) * 1991-09-25 1994-01-04 Konica Corporation Silver halide color photographic light-sensitive material
EP0711804A2 (de) 1994-11-14 1996-05-15 Ciba-Geigy Ag Kryptolichtschutzmittel
EP0782044A1 (en) 1995-12-27 1997-07-02 Konica Corporation Silver halide light-sensitive color photographic material

Also Published As

Publication number Publication date
DE1597572B2 (de) 1975-02-06
NL6710011A (xx) 1968-01-22
DE1670529B2 (de) 1973-06-07
GB1142553A (en) 1969-02-12
CH507263A (de) 1971-05-15
US3530121A (en) 1970-09-22
AT286998B (de) 1971-01-11
DE1597572A1 (de) 1970-05-06
DE1670529C3 (de) 1974-01-10
DE1670529A1 (de) 1972-03-02
DE1597572C3 (de) 1975-09-18
AT288410B (de) 1971-03-10
SE335859B (xx) 1971-06-14
FR7305M (xx) 1969-09-29
SE361477B (xx) 1973-11-05
CH508900A (de) 1971-06-15
SE361478B (xx) 1973-11-05
IL28200A (en) 1972-02-29
GB1142546A (en) 1969-02-12
BE701427A (xx) 1967-12-18
BE701268A (xx) 1967-12-18

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