US3012884A - Production of colored photographic images - Google Patents

Production of colored photographic images Download PDF

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Publication number
US3012884A
US3012884A US705508A US70550857A US3012884A US 3012884 A US3012884 A US 3012884A US 705508 A US705508 A US 705508A US 70550857 A US70550857 A US 70550857A US 3012884 A US3012884 A US 3012884A
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United States
Prior art keywords
phenyl
pyrazolone
color
solution
methyl
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
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US705508A
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English (en)
Inventor
Ramaix Maurice Antoine De
Jaeken Jan
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Gevaert Photo Producten NV
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Gevaert Photo Producten NV
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Priority claimed from GB3960856A external-priority patent/GB880862A/en
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Classifications

    • 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
    • C07D231/46—Oxygen atom in position 3 or 5 and nitrogen atom in position 4
    • C07D231/50—Acylated on said nitrogen atom
    • 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
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
    • 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
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
    • C07D231/26—1-Phenyl-3-methyl-5- pyrazolones, unsubstituted or substituted on the phenyl ring
    • 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
    • C07D231/46—Oxygen atom in position 3 or 5 and nitrogen atom in position 4
    • 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
    • C07D231/46—Oxygen atom in position 3 or 5 and nitrogen atom in position 4
    • C07D231/48—Oxygen atom in position 3 or 5 and nitrogen atom in position 4 with hydrocarbon radicals attached to said nitrogen atom
    • 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
    • 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
    • G03C7/18—Processes for the correction of the colour image in subtractive colour photography
    • 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
    • G03C7/344—Naphtholic couplers

Definitions

  • the present invention relates to a method of producing colored photographic images, more particularly such images which are free from unwanted secondary images due to undesired absorptions of the dyestuffs.
  • Another means to obtain the desired mask image consists in converting, after color development, the residue of the color coupler into a colored compound with adequate absorption. This often requires supplementary baths and has in no case given satisfactory results.
  • the oxidizing substance can be present in a special bath or in one of the baths normally used.
  • the oxidizing substance normally present in the bleaching bath is used.
  • the mask-forming compound can be present in a bath between the color developer and the bleaching bath, or in one of the sensitive or non-sensitive layers of the photographic material. It may be advantageous that it be fast to difiusion and preferably it corresponds to the following general formula:
  • R hydrogen or any substituent, e.g. alkyl including aralkyl, aryl, carboxyl including esterified carboxyl or amino including acyl amino;
  • R alky1 including aralkyl, aryl, or a heterocyclic residue
  • Mask-forming compounds are for instance:
  • EXAIVIPLE 1 A strip of negative multilayer material, the underlying red-sensitive layer of which contains l-hydroxy-Z- naphthoic acid hexadecylarnide-4-sulphonic acid as color coupler is exposed to a wedge through a red-filter. This exposed film is successively: color developed in a devel- I oper containing N:N diethyl para phenylenediamine, fixed, rinsed, treated for 2 minutes in a bath composed of:
  • EXAMPLE 2 A film support is coated with an emulsion layer which besides theusual red sensitizer and l-hydroxy-Z-naphthoic acid-hexadecylamide-4-sulphonic acid as color coupler also contains 2-(p-alpha-hexadecenyl-succinyl-imidophenyl) -3-1nethyl-4-aminopyrazolone-5.
  • a strip or" this film is exposed through a wedge and after color development, fixed, rinsed, bleached in the same bath as in Example 1, fixed, rinsed and dried. On measurement, a decrease of the greenand blue-filter densities is observed for an increase of the red-filter densities, not observed in a test strip containing no pyrazolone derivative.
  • EXAMPLE 3 A film support is coated with an emulsion layer which besides a green sensitizer and 4-hexadecenyl-succinylimido-indazolone as color coupler also contains 2-(p-hexadecenylsuccinylimidophenyl) -3-methyl-4-amino pyrazolone-5. After exposure of a strip as in Example 1, color development, fixing, rinsing, bleaching for instance in a bath mentioned in Example 1, again fixing, rinsing and drying, at strong yellow-brown color is observed all over the surface. On measurement of the wedge, a much greater proportion of green to blue-filter density than in a comparable material coated without the pyrazolone derivative is observed.
  • Photographic element having superposed silver halide emulsion layers sensitive to different regions of the visible spectrum, at least one of said layers containing a color coupler for color development, which is reactive with the oxidation product of an aromatic amino developing agent to form by color development a primary dye image which absorbs a major proportion of light in one region of the visible spectrum, and undesirably absorbs a minor proportion of light in at least one other region of the visible spectrum, at least said one layer also containing a 4-amino-5-pyrazolone derivative of the formula l Ra wherein R is a member selected from the group consisting of alkyl, phenyl, and benzoylamido, R is a member selected from the group consisting of alkyl, phenyl, and p-(a-hexadecenyl-succinyl-amido)-phenyl, R is a member selected from the group consisting of hydrogen, phenyl, and p-(succinyl-amido-methylest

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Plural Heterocyclic Compounds (AREA)
US705508A 1956-12-31 1957-12-27 Production of colored photographic images Expired - Lifetime US3012884A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB3960856A GB880862A (en) 1960-09-27 1956-12-31 Improvements in or relating to the production of coloured photographic images
DEG30580A DE1119666B (de) 1960-09-27 1960-09-27 Verfahren zur Herstellung von farbmaskierten photographischen Farbenbildern durch Farbentwicklung

Publications (1)

Publication Number Publication Date
US3012884A true US3012884A (en) 1961-12-12

Family

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Family Applications (2)

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US705508A Expired - Lifetime US3012884A (en) 1956-12-31 1957-12-27 Production of colored photographic images
US70914A Expired - Lifetime US3013879A (en) 1956-12-31 1960-11-22 Production of color photographic images

Family Applications After (1)

Application Number Title Priority Date Filing Date
US70914A Expired - Lifetime US3013879A (en) 1956-12-31 1960-11-22 Production of color photographic images

Country Status (5)

Country Link
US (2) US3012884A (fr)
BE (1) BE563474A (fr)
DE (1) DE1063900B (fr)
FR (2) FR1207422A (fr)
GB (1) GB975930A (fr)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3245787A (en) * 1959-11-13 1966-04-12 Gevaert Photo Prod Nv Production of color photographic images
US3249431A (en) * 1960-03-29 1966-05-03 Gevaert Photo Prod Nv Production of color photographic images
US4061498A (en) * 1975-05-30 1977-12-06 Agfa-Gevaert, N.V. Photographic material containing 2-acyl-2-pyrazolin-5-on-couplers
US4128425A (en) * 1977-05-06 1978-12-05 Polaroid Corporation Photographic developers
EP1550656A1 (fr) * 2003-12-01 2005-07-06 L'oreal Dérivés de 4-5-diamino-N,N-dihydro-pyrazol-3-one utilisés pour la teinture des fibres keratiniques
FR2866338A1 (fr) * 2004-02-18 2005-08-19 Oreal Composition pour la teinture des fibres keratiniques comprenant au moins un derive de diamino-n,n-dihydro-pyrazolone
US20080005853A1 (en) * 2006-06-20 2008-01-10 Francois Cottard Process for the predictable dyeing of keratinous fibers comprising applying at least one composition comprising at least one diamino-N, N-dihydropyrazolone derivative and at least one composition chosen from fundamental and/or golden-highlights compositions
US20080016627A1 (en) * 2006-06-20 2008-01-24 Francois Cottard Composition for dyeing of keratin fibers, comprising 2,3-diamino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one, at least one oxidation base chosen from para-phenylenediamine and para-tolylenediamine, and a substituted meta-aminophenol
US20080016628A1 (en) * 2006-06-20 2008-01-24 Francois Cottard Composition for dyeing keratin fibers, comprising 2,3-diamino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one, 6-chloro-2-methyl-5-aminophenol and a substituted meta-aminophenol
US20080163883A1 (en) * 2006-11-30 2008-07-10 Francois Cottard Dye composition of acidic pH comprising 2,3-diamino-6, 7-dihydro-1H, 5H-pyrazolo[1,2-a]pyrazol-1-one, a coupler, a particular surfactant and an oxidizing agent and processes and kits using said composition
US20090007347A1 (en) * 2006-11-30 2009-01-08 Francois Cottard Dye composition of acidic pH comprising 2,3-diamino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one, a para-phenylenediamine, a meta-aminophenol and an oxidizing agent, and processes for dyeing keratin fibers using the composition

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE587525A (fr) * 1960-02-12
BE631903A (fr) * 1962-05-04

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2163781A (en) * 1935-06-07 1939-06-27 Agfa Ansco Corp Photographic developing process
GB685061A (en) * 1949-12-13 1952-12-31 Gevaert Photo Prod Nv Improvements in or relating to the manufacture of photographic multi-colour images
GB765286A (en) * 1954-03-15 1957-01-09 Agfa Ag Photographic developers

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE476358A (fr) * 1944-05-03
US2428054A (en) * 1945-08-30 1947-09-30 Eastman Kodak Co Photographic color correction using colored couplers
GB652953A (en) * 1948-08-20 1951-05-02 Karl Otto Ganguin Colour photography
NL80125C (fr) * 1948-09-15
GB661211A (en) * 1949-02-09 1951-11-21 Ilford Ltd Improvements in or relating to colour photography

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2163781A (en) * 1935-06-07 1939-06-27 Agfa Ansco Corp Photographic developing process
GB685061A (en) * 1949-12-13 1952-12-31 Gevaert Photo Prod Nv Improvements in or relating to the manufacture of photographic multi-colour images
GB765286A (en) * 1954-03-15 1957-01-09 Agfa Ag Photographic developers

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3245787A (en) * 1959-11-13 1966-04-12 Gevaert Photo Prod Nv Production of color photographic images
US3245788A (en) * 1959-11-13 1966-04-12 Gevaert Photo Prod Nv Production of color photographic images
US3249431A (en) * 1960-03-29 1966-05-03 Gevaert Photo Prod Nv Production of color photographic images
US4061498A (en) * 1975-05-30 1977-12-06 Agfa-Gevaert, N.V. Photographic material containing 2-acyl-2-pyrazolin-5-on-couplers
US4128425A (en) * 1977-05-06 1978-12-05 Polaroid Corporation Photographic developers
US20050166335A1 (en) * 2003-12-01 2005-08-04 Laurent Vidal Composition for dyeing keratinous fibers comprising at least one diamino-N,N-dihydropyrazolone derivative
US20080071092A1 (en) * 2003-12-01 2008-03-20 L'oreal S.A. Composition for dyeing keratinous fibers comprising at least one diamino-N,N-dihydropyrazolone derivative
EP1764082A3 (fr) * 2003-12-01 2007-05-23 L'oreal Dérivés de 4-5-diamino-N,N-dihydro-pyrazol-3-one utilisés pour la teinture des fibres keratiniques
US7285137B2 (en) 2003-12-01 2007-10-23 L'oreal, S.A. Composition for dyeing keratinous fibers comprising at least one diamino-N,N-dihydropyrazolone derivative
EP1550656A1 (fr) * 2003-12-01 2005-07-06 L'oreal Dérivés de 4-5-diamino-N,N-dihydro-pyrazol-3-one utilisés pour la teinture des fibres keratiniques
CN1660033B (zh) * 2003-12-01 2013-07-17 莱雅公司 含有至少一种二氨基-n,n-二氢吡唑啉酮衍生物的角蛋白纤维染色组合物
US7642360B2 (en) 2003-12-01 2010-01-05 L'oreal S.A. Composition for dyeing keratinous fibers comprising at least one diamino-N,N-dihydropyrazolone derivative
FR2866338A1 (fr) * 2004-02-18 2005-08-19 Oreal Composition pour la teinture des fibres keratiniques comprenant au moins un derive de diamino-n,n-dihydro-pyrazolone
US20080005853A1 (en) * 2006-06-20 2008-01-10 Francois Cottard Process for the predictable dyeing of keratinous fibers comprising applying at least one composition comprising at least one diamino-N, N-dihydropyrazolone derivative and at least one composition chosen from fundamental and/or golden-highlights compositions
US20080016628A1 (en) * 2006-06-20 2008-01-24 Francois Cottard Composition for dyeing keratin fibers, comprising 2,3-diamino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one, 6-chloro-2-methyl-5-aminophenol and a substituted meta-aminophenol
US7651537B2 (en) 2006-06-20 2010-01-26 L'oreal S.A. Composition for dyeing keratin fibers, comprising 2,3-diamino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one, 6-chloro-2-methyl-5-aminophenol and a substituted meta-aminophenol
US7651536B2 (en) 2006-06-20 2010-01-26 L'oreal S.A. Composition for dyeing of keratin fibers, comprising 2,3-diamino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one, at least one oxidation base chosen from para-phenylenediamine and para-tolylenediamine, and a substituted meta-aminophenol
US7918900B2 (en) 2006-06-20 2011-04-05 L'oreal S.A. Process for the predictable dyeing of keratinous fibers comprising applying at least one composition comprising at least one diamino-N, N-dihydropyrazolone derivative and at least one composition chosen from fundamental and/or golden-highlights compositions
US20080016627A1 (en) * 2006-06-20 2008-01-24 Francois Cottard Composition for dyeing of keratin fibers, comprising 2,3-diamino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one, at least one oxidation base chosen from para-phenylenediamine and para-tolylenediamine, and a substituted meta-aminophenol
US20080163883A1 (en) * 2006-11-30 2008-07-10 Francois Cottard Dye composition of acidic pH comprising 2,3-diamino-6, 7-dihydro-1H, 5H-pyrazolo[1,2-a]pyrazol-1-one, a coupler, a particular surfactant and an oxidizing agent and processes and kits using said composition
US20090007347A1 (en) * 2006-11-30 2009-01-08 Francois Cottard Dye composition of acidic pH comprising 2,3-diamino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one, a para-phenylenediamine, a meta-aminophenol and an oxidizing agent, and processes for dyeing keratin fibers using the composition
US7651539B2 (en) 2006-11-30 2010-01-26 L'oreal S.A. Dye composition of acidic pH comprising 2,3-diamino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one, a coupler, a particular surfactant and an oxidizing agent and processes and kits using said composition
US7766977B2 (en) 2006-11-30 2010-08-03 L'oreal S.A. Dye composition of acidic pH comprising 2,3-diamino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one, a para-phenylenediamine, a meta-aminophenol and an oxidizing agent, and processes for dyeing keratin fibers using the composition

Also Published As

Publication number Publication date
US3013879A (en) 1961-12-19
DE1063900B (de) 1959-08-20
FR1207422A (fr) 1960-02-16
FR81106E (fr) 1967-08-09
BE563474A (fr) 1960-06-17
GB975930A (en) 1964-11-25

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