US2439098A - Alkoxy pyrazolone couplers - Google Patents

Alkoxy pyrazolone couplers Download PDF

Info

Publication number
US2439098A
US2439098A US599742A US59974245A US2439098A US 2439098 A US2439098 A US 2439098A US 599742 A US599742 A US 599742A US 59974245 A US59974245 A US 59974245A US 2439098 A US2439098 A US 2439098A
Authority
US
United States
Prior art keywords
pyrazolone
couplers
alkoxy
ethoxy
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
Application number
US599742A
Inventor
Henry D Porter
Weissberger Arnold
Walter A Gregory
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eastman Kodak Co
Original Assignee
Eastman Kodak Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Priority to US599742A priority Critical patent/US2439098A/en
Application granted granted Critical
Publication of US2439098A publication Critical patent/US2439098A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • 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
    • C07D231/28—Two oxygen or sulfur atoms
    • C07D231/30—Two oxygen or sulfur atoms attached in positions 3 and 5
    • C07D231/32—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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 photographic colorforming compounds and'particularly to coupler compounds which are derivatives of pyrazolones for color-forming processes of color photography.
  • Pyrazolone couplers have been described in Seymour U. S. Patent 1,969,479. Acylamino pyrazolone couplers and phenylamino pyrazolone couplers have been described respectively in Porter and Weissberger U. S. Patents 2,343,702 and 2,311,081. 3-amino pyrazolone couplers have been described in Porterand -Weissberger U. S. Reissue Patent 22,329 and s-acylamino 'pyrazolone couplers in Porter and Weissberger U. S. patent application Serial No. 457,276, now U. S. Patent 2,369,489,
  • Couplers which possess valuable properties when used in color photography. These couplers have an alkoiiy group in the 3-position of the pyrazolone ring and are represented by the following gen-- eral formula:
  • R is hydrogen, alkyl, aryl, heterocycllc, or thiocarbamyl, and R is alkyl.
  • the alkyl group may be methyl, ethyl, propyl, or butyl
  • the aryl group may be unsubstituted phenyl or substituted aryl group, such as nitrophenyl, sulfamyl phenyl, or chlorophenyl
  • the heterocyclic groups may be radicals, such as benzothiazolyl orbenzoxazolyl.
  • the alkyl groups are lower alkyl groups, that is alkyl groups containing less than about five carbon atoms.
  • the couplers of our invention are made by a' method which we believe to be novel.
  • Thedesired coupler separates as the sodiumsalt and thisis dissolved in water and the compound precipitated with acid.
  • the general method of preparation is represented by the following equation:
  • N COCgH5 CaHs-N M. P. 116 l-phe11yl-3-cthoxy-5-pyrazolone M.P. 197 1 (p-sulfamylphenyl)-3-ethoxy-5-pyrazolone p-sulfamylphenylhydrazine is prepared following Crippa and MafiehGa-zz. chim. Ital., 72, 97 (1942).
  • M. P. 177 3-ethoxy-5-pyrazolone ' may include ethyl c,c-diethoxyacrylate, ethyl 13,;3-dipropoxyacrylate and ethyl pp-dibutoxyacrylate.
  • Example 1 Equal molecular weights of phenylhydrazine and ethyl flfi-diethoxyacrylate are heated together on the'steam bath for /2 to 1 hour with or without solvent. A solution of sodium ethylate (one equivalent of sodium dissolved in 17 cc. per gram of absolute ethyl alcohol) is added and the mixture heated for another quarter to halflhour. A clear solution is then formed by the addition of water and the product precipitated by acidification and is then filtered and recrystallized from a suitable solvent. The melting point is 116 C.
  • Ethyl afi-diethoxyacrylate is prepared according to the method of Reitler and Weindel, Berichte 40, 3359 (1907).
  • the corresponding flfi-dipropoxy and pfi-dibutoxy esters are prepared analogously using n-propanol or n-butanol instead of ethanol.
  • the boiling point of the dibutoxy ester is -160 at 7 mm. pressure.
  • the couplers of our invention may be incorporated in the developed solution or in the sensitive emulsion layer.
  • the couplers When incorporated in the developed solution, the couplers may be used in processes such as those described in Mannes and Godowsky U. S. Patent 2,113,329 or Mannes, Godowsky and Wilder U. S. Patent 2,252,718.
  • the couplers When incorporated in the sensitive emulsion layer, the couplers may be used in processes, such as those described in Fisher U. S. Patent 1,055,- 155, Mannes and Godowsky U. S. Patent 2,304,- 940 or J elley and Vittum U. S. Patent 2,322,027.
  • Example 2 A. 2 amino-S-diethyl aminotoluenehydrochloride grams..- 2 Sodium sulfite anhydrous do 2 Sodium carbonate anhydrous do 20 Potassium bromide do 1 Water to liter- 1 B. 1-Phenyl-3-ethoxy-5-pyrazolone grams 2 Sodium hydroxide (10% solution) cc 10 For use B is added to A.
  • Example 3 Dimethyl p phenylenedlaminesulfate grams 3 Sodium sulfite anhydrous do 5 Sodium carbonate anhydrous do.. 20 Potassium bromide do-.. 2 Water to liter 1 l3. 1-(2-benzothiazolyl) -3- ethoxy-fi-pyrazolone grams.-- 3 Isopropyl alcohol cc 100 For use B is added to A.
  • coupler compounds of our invention such as compound No. '7 are themselves nondifiusing and may be incorporated in the photographic layer without the use of additional compounds to prevent difiusion.
  • Other couplers may be rendered non-diflusing in the emulsion layer by the use of special means as by causing the couplers to be absorbed or adsorbed to the sensitive silver salt.
  • any color-forming developer containing a primary amino group may be used.
  • substituents in the rin such as alkylphenylenediamines and alkyltoluenediamines.
  • These compounds are usually used in the salt form such as the hydrochloride or the sulfate which are more stable than the amines themselves.
  • Suitable compounds are diethyl-p-phenylenediamine hydrochloride, monomethyl-p-phenyienediamine hydrochloride, dimethyl-p-phenylenediamine hydrochlori'de and 2-amino-5-diethylaminotoluene hydrochloride.
  • the p-aminophenols 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 compound to form a dye image.
  • Our development process may be employed for the production of colored photographic images in layers of gelatin or other water-permeable colloidal carrier, such as collodion, organic esters oi cellulose, or synthetic resins.
  • the carrier may be supported by a transparent medium such as glass, a cellulose ester 01' non-transparent refleeting medium, such as paper or an opaque cellulose ester.
  • the emulsion may be coated as a single layer on the support or as superposed layers on one or both sides of the support.
  • the superposed layers may be differentially sensitized so that difierent colors may be recorded in the layers and differently colored images formed therein.
  • the method of producing a 3-alkoxy-5- pyrazolone which comprises heating a monosubstituted hydrazine in which the substituent is selected from the class consisting of hydrogen, alkyl, aryl, benzothiazolyl, benzoxazolyl and thiocarbamyl groups, and an ethyl flJl-dialkoxyacrylate in which the alkoxy is a lower alkoxy group on a steam bath until reaction is complete adding sodium ethylate and heating for a further period, precipitating the resulting product from solution and removing it from the solution.
  • N G-OP.
  • R represents a member selected from the class consisting of hydrogen, alkyl, aryl, benzothiazolyl, benzoxazolyl and thiocarbamyl groups, and R represents a. lower alkyl group.
  • R represents a lower alkyl group.

Description

Patented Apr. 6, 1948 UNITED STATES PATENT OFFICE ALKOXY PYRAZOLONE COUPLERS No Drawing. Original application December 22,
1944,,Serial No. 569,428. Divided and this application June 15, 1945, Serial No. 599,742
This invention relates to photographic colorforming compounds and'particularly to coupler compounds which are derivatives of pyrazolones for color-forming processes of color photography.
This application is a division of our application, Serial No. 569,428, filed December 22, 1944,;now abandoned.
The formation of colored photographic images by coupling thedevelopment product of aromatic amino developing agents with color-forming or coupling compounds is well known. In these processes, the color formation is ordinarily accomplished by the subtractive process and the image dyes are of the subtractive primary colors, cyan or blue-green, ma enta, and yellow, The magenta dyes are. frequently produced from pyrazolone or cyano acetyl couplers and the present invention relates to couplers of the former type.
Pyrazolone couplers have been described in Seymour U. S. Patent 1,969,479. Acylamino pyrazolone couplers and phenylamino pyrazolone couplers have been described respectively in Porter and Weissberger U. S. Patents 2,343,702 and 2,311,081. 3-amino pyrazolone couplers have been described in Porterand -Weissberger U. S. Reissue Patent 22,329 and s-acylamino 'pyrazolone couplers in Porter and Weissberger U. S. patent application Serial No. 457,276, now U. S. Patent 2,369,489,
Wehave discovered a class of pyrazolone couplers which possess valuable properties when used in color photography. These couplers have an alkoiiy group in the 3-position of the pyrazolone ring and are represented by the following gen-- eral formula:
in which R is hydrogen, alkyl, aryl, heterocycllc, or thiocarbamyl, and R is alkyl.
In the general formula, the alkyl group may be methyl, ethyl, propyl, or butyl, the aryl group may be unsubstituted phenyl or substituted aryl group, such as nitrophenyl, sulfamyl phenyl, or chlorophenyl, and the heterocyclic groups may be radicals, such as benzothiazolyl orbenzoxazolyl. The alkyl groups are lower alkyl groups, that is alkyl groups containing less than about five carbon atoms.
The couplers of our invention .are made by a' method which we believe to be novel. According to this method, hydrazine or a hydrazine dc- 5 Claims. (01. 2607-3101) rivative is heated with an ethyl aB-dialkoxyacrylate until the reaction is complete, as indicated by the evolution of alcohol or the solution of the hydrazine, and sodium ethylate in alcohol is then added and the mixture heated for a further shortper-iod. Thedesired coupler separates as the sodiumsalt and thisis dissolved in water and the compound precipitated with acid. The general method of preparation is represented by the following equation:
N C2115 C=CHCO 0 CzHs In the equation, R and B have the same meaning as ,in the general formula above.
The following examples illustrate compounds which aresuitable for use according to our invention:
N=COCgH5 CaHs-N M. P. 116 l-phe11yl-3-cthoxy-5-pyrazolone M.P. 197 1 (p-sulfamylphenyl)-3-ethoxy-5-pyrazolone p-sulfamylphenylhydrazine is prepared following Crippa and MafiehGa-zz. chim. Ital., 72, 97 (1942).
- 1(2benzothiazolyl)-3-ethoxy-5-pyrazolone 2-benzothiazolylhydrazine prepared following German Patent 614,327 (1935).
59 1(2-1)enzothiazolyl)-3-butoxy-5-pyrazolone l-[6(p-tert. butylphenoxy)-2-benzothiazolyl]-3-butoxy-5-pyrazolone 6(p-tert. butylphenoxy)-2-benzothiazolyl hydrazine was prepared by the following series of reactions:
0. W O... 0.0a...
M. P. 71 (free base) mm-Qo-O-rrm-nm NaOH This preparation follows closely that given in J. Am. Chem. Soc., 53, 1891 (1931).
PCls
M. P. 152 (heating rapidly) 1-(2-benzoxazolyl)-3-ethoxy-5-pyrazolone 2-benzoxazolylhydrazine prepared following German Patent 614,327 (1935).
HzNOSN M. 1. 171 l-thiocarbamyl-3-ethoxy-5-pyrazolone (III?- E: 0
M. P. 177 3-ethoxy-5-pyrazolone 'may include ethyl c,c-diethoxyacrylate, ethyl 13,;3-dipropoxyacrylate and ethyl pp-dibutoxyacrylate.
The following example illustrates the preparation of 1-phenyl-3-ethoxy-5-pyrazolone, compound No. 1.
Example 1 Equal molecular weights of phenylhydrazine and ethyl flfi-diethoxyacrylate are heated together on the'steam bath for /2 to 1 hour with or without solvent. A solution of sodium ethylate (one equivalent of sodium dissolved in 17 cc. per gram of absolute ethyl alcohol) is added and the mixture heated for another quarter to halflhour. A clear solution is then formed by the addition of water and the product precipitated by acidification and is then filtered and recrystallized from a suitable solvent. The melting point is 116 C.
Ethyl afi-diethoxyacrylate is prepared according to the method of Reitler and Weindel, Berichte 40, 3359 (1907). The corresponding flfi-dipropoxy and pfi-dibutoxy esters are prepared analogously using n-propanol or n-butanol instead of ethanol. The boiling point of the dibutoxy ester is -160 at 7 mm. pressure.
The couplers of our invention may be incorporated in the developed solution or in the sensitive emulsion layer. When incorporated in the developed solution, the couplers may be used in processes such as those described in Mannes and Godowsky U. S. Patent 2,113,329 or Mannes, Godowsky and Wilder U. S. Patent 2,252,718. When incorporated in the sensitive emulsion layer, the couplers may be used in processes, such as those described in Fisher U. S. Patent 1,055,- 155, Mannes and Godowsky U. S. Patent 2,304,- 940 or J elley and Vittum U. S. Patent 2,322,027.
The following examples illustrate developing solutions containing the couplers used according to our invention:
Example 2 A. 2 amino-S-diethyl aminotoluenehydrochloride grams..- 2 Sodium sulfite anhydrous do 2 Sodium carbonate anhydrous do 20 Potassium bromide do 1 Water to liter- 1 B. 1-Phenyl-3-ethoxy-5-pyrazolone grams 2 Sodium hydroxide (10% solution) cc 10 For use B is added to A.
Example 3 A. Dimethyl p phenylenedlaminesulfate grams 3 Sodium sulfite anhydrous do 5 Sodium carbonate anhydrous do.. 20 Potassium bromide do-.. 2 Water to liter 1 l3. 1-(2-benzothiazolyl) -3- ethoxy-fi-pyrazolone grams.-- 3 Isopropyl alcohol cc 100 For use B is added to A.
Certain of the coupler compounds of our invention, such as compound No. '7 are themselves nondifiusing and may be incorporated in the photographic layer without the use of additional compounds to prevent difiusion. Other couplers may be rendered non-diflusing in the emulsion layer by the use of special means as by causing the couplers to be absorbed or adsorbed to the sensitive silver salt.
In the development of exposed photographic silver halide emulsion layers using the couplers of our invention, any color-forming developer containing a primary amino group may be used. These include developers having two primary amino groups as well as those having one of the amino groups substituted, or having substituents in the rin such as alkylphenylenediamines and alkyltoluenediamines. These compounds are usually used in the salt form such as the hydrochloride or the sulfate which are more stable than the amines themselves. Suitable compounds are diethyl-p-phenylenediamine hydrochloride, monomethyl-p-phenyienediamine hydrochloride, dimethyl-p-phenylenediamine hydrochlori'de and 2-amino-5-diethylaminotoluene hydrochloride. The p-aminophenols 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 compound to form a dye image.
Our development process may be employed for the production of colored photographic images in layers of gelatin or other water-permeable colloidal carrier, such as collodion, organic esters oi cellulose, or synthetic resins. The carrier may be supported by a transparent medium such as glass, a cellulose ester 01' non-transparent refleeting medium, such as paper or an opaque cellulose ester. The emulsion may be coated as a single layer on the support or as superposed layers on one or both sides of the support. The superposed layers may be differentially sensitized so that difierent colors may be recorded in the layers and differently colored images formed therein.
The examples and compounds set forth in the present specification are illustrative only and it is to be understood that our invention is limited only by the scope of the appended claims.
We claim:
1. The method of producing a 3-alkoxy-5- pyrazolone, which comprises heating a monosubstituted hydrazine in which the substituent is selected from the class consisting of hydrogen, alkyl, aryl, benzothiazolyl, benzoxazolyl and thiocarbamyl groups, and an ethyl flJl-dialkoxyacrylate in which the alkoxy is a lower alkoxy group on a steam bath until reaction is complete adding sodium ethylate and heating for a further period, precipitating the resulting product from solution and removing it from the solution.
2. The method of producing 1-phenyl-3- ethoxy-S-pyrazolone, which comprises heating equal molecular weights of phenyl hydrazine and ethyl 5,;8-diethoxyacrylate on a steam bath. for V to one hour, adding sodium ethylate and heating for a further period of A to /g hour, precipitating the resulting 1-phenyl-3-ethoxy-5-pyrazolone from solution and removing it from the solution.
3. A 3-alkoxy-5-pyrazolone selected from the group of 3-alkoxy-5-pyrazolones represented by the following general formula:
N=G-OP.
wherein R represents a member selected from the class consisting of hydrogen, alkyl, aryl, benzothiazolyl, benzoxazolyl and thiocarbamyl groups, and R represents a. lower alkyl group.
4. A 1-phenyl-3-alkoxy-5-pyrazolone selected from the group of 1-phenyl-3-alkoxy-5-p:vrazolones represented by the following general formula:
N=CQR' Colin-N CO-GH:
wherein R represents a lower alkyl group.
5. 1 phenyl-3-ethoxy-5-pyrazolone.
HENRY D. PORTER. ARNOLD WEISSBERGER. WALTER A. GREGORY.
REFERENCES CITED The following references are of record in the file of this patent:
J. Am. Chem. Soc., vol. 65, pages 52-54, January 1943.
US599742A 1944-12-22 1945-06-15 Alkoxy pyrazolone couplers Expired - Lifetime US2439098A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US599742A US2439098A (en) 1944-12-22 1945-06-15 Alkoxy pyrazolone couplers

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US56942844A 1944-12-22 1944-12-22
US599742A US2439098A (en) 1944-12-22 1945-06-15 Alkoxy pyrazolone couplers

Publications (1)

Publication Number Publication Date
US2439098A true US2439098A (en) 1948-04-06

Family

ID=27075053

Family Applications (1)

Application Number Title Priority Date Filing Date
US599742A Expired - Lifetime US2439098A (en) 1944-12-22 1945-06-15 Alkoxy pyrazolone couplers

Country Status (1)

Country Link
US (1) US2439098A (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2630437A (en) * 1947-11-19 1953-03-03 Mallinckrodt Chemical Works Method for preparing beta keto esters of thiophenes
US2715120A (en) * 1950-07-20 1955-08-09 Ciba Ltd Monoazo-dyestuffs
US4256902A (en) * 1977-12-23 1981-03-17 Montedison S.P.A. Process for the preparation of 3-chloro-5-hydroxypyrazoles
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
EP0665271A1 (en) * 1994-01-31 1995-08-02 Fuji Photo Film Co., Ltd. Pyrazolonoxonol compound and silver halide photographic material comprising same
EP0782044A1 (en) 1995-12-27 1997-07-02 Konica Corporation Silver halide light-sensitive color photographic material
US6210447B1 (en) * 1996-03-22 2001-04-03 L'oreal Compositions containing pyrazolin-3,5-dione couplers for use in keratin fiber dyeing methods and kits

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2630437A (en) * 1947-11-19 1953-03-03 Mallinckrodt Chemical Works Method for preparing beta keto esters of thiophenes
US2715120A (en) * 1950-07-20 1955-08-09 Ciba Ltd Monoazo-dyestuffs
US4256902A (en) * 1977-12-23 1981-03-17 Montedison S.P.A. Process for the preparation of 3-chloro-5-hydroxypyrazoles
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
EP0665271A1 (en) * 1994-01-31 1995-08-02 Fuji Photo Film Co., Ltd. Pyrazolonoxonol compound and silver halide photographic material comprising same
US5556985A (en) * 1994-01-31 1996-09-17 Fuji Photo Film Co., Ltd. Pyrazolonoxonol compounds
EP0782044A1 (en) 1995-12-27 1997-07-02 Konica Corporation Silver halide light-sensitive color photographic material
US6210447B1 (en) * 1996-03-22 2001-04-03 L'oreal Compositions containing pyrazolin-3,5-dione couplers for use in keratin fiber dyeing methods and kits
US6551360B2 (en) 1996-03-22 2003-04-22 Laurent Vidal Pyrazoline-3,5-dione-containing compositions for dyeing keratin fibres; their use in dyeing as couplers; dyeing process

Similar Documents

Publication Publication Date Title
US2343703A (en) Pyrazolone coupler for color photography
US2369929A (en) Acylamino phenol couplers
US3615506A (en) Silver halide emulsions containing 3-cyclicamino-5-pyrazolone color couplers
US2369489A (en) Acylated amino pyrazolone couplers
US3432300A (en) 6-hydroxy chromans used as stabilizing agents in a color photographic element
US3034892A (en) Magenta-colored cyan-forming couplers
US3311476A (en) Two-equivalent couplers for color photography
US3926631A (en) Silver halide photographic light-sensitive material
US2808329A (en) Photographic color correction using colored and uncolored couplers
US2311082A (en) Pyrazolone coupler for color photography
JPS5912169B2 (en) Silver halide color photosensitive material
US4404274A (en) Photographic light sensitive element containing yellow color coupler and method for forming yellow photographic images
JPS6145247A (en) Color graphic recording material having yellow-dir coupler
US3891445A (en) Color photographic light-sensitive materials
US3573050A (en) Color photographic layers comprising non-diffusible 5-hydroxycoumarans as stabilizing compounds
US3935016A (en) Silver halide color photographic materials containing 3-anilino-5-pyrazolone couplers
US3615505A (en) Silver halide emulsion containing 2-pyrazolin-5-one color coupler
US2439098A (en) Alkoxy pyrazolone couplers
US2453661A (en) Colored couplers
US2933391A (en) Photographic emulsions containing 5-pyrazolone coupler compounds
US2436130A (en) Acyl substituted reactive methylene color couplers
JPH01554A (en) Silver halide color photographic material containing pyrazoloazole cyan coupler
US3684514A (en) Light-sensitive silver halide color photographic emulsions
US2435173A (en) Acetyl n-heterocyclic couplers for color photography
US2455170A (en) Colored couplers