US3413072A - Dyeing human hair with an oxidation dye and 1-phenyl-3-methyl-5-pyrazolone - Google Patents

Dyeing human hair with an oxidation dye and 1-phenyl-3-methyl-5-pyrazolone Download PDF

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Publication number
US3413072A
US3413072A US428701A US42870165A US3413072A US 3413072 A US3413072 A US 3413072A US 428701 A US428701 A US 428701A US 42870165 A US42870165 A US 42870165A US 3413072 A US3413072 A US 3413072A
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US
United States
Prior art keywords
pyrazolone
dye
oxidation
phenyl
methyl
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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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US428701A
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English (en)
Inventor
Ghilardi Giuliana
Lemonnier Jacqueline Raymonde
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LOreal SA
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LOreal SA
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom

Definitions

  • ABSTRACT OF THE DISCLOSURE A process for dyeing human hair with an oxidation dye, which comprises dyeing the hair with a composition containing an effective amount of the dye, an oxidation retarding amount of 1-phenyl-3-methyl-5-pyrazolone and an effective amount of an effective oxidizing agent.
  • This invention relates to the dyeing of hair using oxidation dyes, and in particular the use of 5-pyrazolones as oxidation retarders.
  • oxidation dyes that is, dyes which must be brought into contact with an oxidising agent before they can have a dyeing effect
  • the oxidising agent for instance hydrogen peroxide, causing components of the oxidation dye to couple together.
  • the oxidising agent can also serve, where necessary, to decolorise the hair partially so as to obtain at the end of the dyeing process a coloration which is lighter than the initial coloration.
  • oxidation dyes are extremely sensitive to oxidising agents, it is generally necessary to protect the dyes against accidental oxidation during storage and to control their oxidation during the hair dyeing.
  • the oxidative coupling of the dye should be delayed to a suflicient extent that it takes place after the product has been applied to the hair and not in the vessel in which the mixing has taken place.
  • This requirement is of great importance in practice, because when oxidation takes place in the mixing vessel the dyeing power of the mixture gradually decreases, and it becomes impossible to obtain levelness, ie the same coloration of all the locks of one head of hair if, between the time when the dyeing composition has been applied to the first lock and the time when it has been applied to the lock last treated, the mixture being applied to the hair has become substantially oxidised.
  • the present invention consists in one aspect of compositions suitable for use in dyeing hair, especially human hair, comprising an oxidation dye and a 5-pyrazolone as an oxidation retarder for the dye.
  • the present invention also consists in a process for dyeing human hair with an oxidation dye, which comprises mixing the dye with a S-pyrazolone and with an oxidising agent, the S-pyrazolone being mixed with the dye not substantially later than the mixing together of the dye and the oxidising agent, applying the mixture to the hair, allowing suflicient time to elapse for the dye to exert its dyeing effect and then removing any unwanted excess of the mixture or its components from the hair.
  • oxidative dye is used to refer to either the dyestuff used to dye the hair or to its precursor prior to admixture with the oxidising agent, and the appropriate meaning is to be understood in accordance with the context,
  • the amount of S-pyrazolone in the compositions and process of this invention is preferably 1 to 50 moles of S-pyrazolone per moles of oxidation dye.
  • they can contain a preservative, for instance ammonium thioglycollate, sodium sulphite or ascorbic acid.
  • a composition of the invention is prepared by mixing the following:
  • This composition is mixed just before use with an equal volume of hydrogen peroxide (20 vol.), the mixture thus obtained forming a transparent red gel which can be kept for about 30 minutes without undergoing any appreciable change.
  • hydrogen peroxide 20 vol.
  • a composition according to the invention is prepared by mixing:
  • Oleic acid g Condensate of 1 mol of synthetic oxo alcohol and 3 molecules of ethylene oxide g 250 Butyl Cellosolve g 50 Ethyl alcohol g 150 Ammonia (22 B.) cc 100 p-Toluylenediamine g 13 .5 m-Diarninoanisole -g-.. 0.5 Resorcinol g 5 3 p-Aminophenol g 2.3 1-phenyl-3-methyl-5-pyrazolone g 7 Diethylenetriaminepentacetic acid (sodium salt) g 2.
  • This composition is mixed just before use with an equal volume of hydrogen peroxide (20 vol.), the mixture thus obtained forming a transparent red gel which can be kept for about 30 minutes without undergoing any appreciable change.
  • hydrogen peroxide 20 vol.
  • the 1-phenyl-3-methyl-5-pyrazolone shows substantially no increase in optical density.
  • a process for dyeing human hair with an oxidation dye which comprises dyeing the hair with a composition containing an effective amount of the dye, an oxidation retarding amount of 1-phenyl-3-methyl-5-pyrazolone and an effective amount of an oxidizing agent.
  • composition also contains a preservative selected from the group consisting of ammonium thioglycollate, sodium sulphite and ascorbic acid.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)
US428701A 1964-02-04 1965-01-28 Dyeing human hair with an oxidation dye and 1-phenyl-3-methyl-5-pyrazolone Expired - Lifetime US3413072A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR962624A FR1422838A (fr) 1964-02-04 1964-02-04 Composition nouvelle pour la teinture des cheveux à l'aide de colorants d'oxydation

Publications (1)

Publication Number Publication Date
US3413072A true US3413072A (en) 1968-11-26

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Family Applications (1)

Application Number Title Priority Date Filing Date
US428701A Expired - Lifetime US3413072A (en) 1964-02-04 1965-01-28 Dyeing human hair with an oxidation dye and 1-phenyl-3-methyl-5-pyrazolone

Country Status (8)

Country Link
US (1) US3413072A (ko)
AT (1) AT257841B (ko)
BE (1) BE658983A (ko)
CH (1) CH433602A (ko)
DE (1) DE1492072A1 (ko)
FR (1) FR1422838A (ko)
GB (1) GB1065223A (ko)
NL (1) NL6501296A (ko)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6074438A (en) * 1998-03-03 2000-06-13 Bristol-Myers Squibb Co. Hair dyeing compositions containing 2-chloro- and 2,6-dichloro-4-aminophenol and phenylpyrazolones
EP1314418A1 (en) * 2001-11-27 2003-05-28 Dong Sung pharmaceuticals Co., Ltd. Hairdye composition including 1-phenyl-3-methyl-5-pyrazolone and method for obtaining the same
WO2010123863A2 (en) * 2009-04-20 2010-10-28 The Procter & Gamble Company Keratin dyeing compositions comprising a radical scavenger and use thereof
US20110035886A1 (en) * 2009-04-20 2011-02-17 Guiru Zhang Keratin Dyeing Compositions Comprising a Radical Scavenger and a Chelant and Use Thereof
WO2020259216A1 (en) * 2019-06-28 2020-12-30 L'oreal Composition for dyeing keratin fibres and use thereof
FR3128376A1 (fr) * 2021-09-29 2023-04-28 L'oreal Composition DE retardatEUR et nécessaire de teinture la coMPRenant

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117651546A (zh) * 2021-06-30 2024-03-05 莱雅公司 氧化的阻滞剂组合物

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1019576A (en) * 1910-05-17 1912-03-05 Agfa Ag Hair-dye.
US2186849A (en) * 1935-08-07 1940-01-09 Agfa Ansco Corp Manufacture of photographic silver halide emulsions
US2294909A (en) * 1939-02-13 1942-09-08 Du Pont Chemical process and composition
US2311082A (en) * 1941-11-14 1943-02-16 Eastman Kodak Co Pyrazolone coupler for color photography
US2610941A (en) * 1946-12-14 1952-09-16 L Oreal Soc Hair-dye compositions
US3062650A (en) * 1960-05-05 1962-11-06 Eastman Kodak Co Photographic printout system comprising an organic azide

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1019576A (en) * 1910-05-17 1912-03-05 Agfa Ag Hair-dye.
US2186849A (en) * 1935-08-07 1940-01-09 Agfa Ansco Corp Manufacture of photographic silver halide emulsions
US2294909A (en) * 1939-02-13 1942-09-08 Du Pont Chemical process and composition
US2311082A (en) * 1941-11-14 1943-02-16 Eastman Kodak Co Pyrazolone coupler for color photography
US2610941A (en) * 1946-12-14 1952-09-16 L Oreal Soc Hair-dye compositions
US3062650A (en) * 1960-05-05 1962-11-06 Eastman Kodak Co Photographic printout system comprising an organic azide

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6074438A (en) * 1998-03-03 2000-06-13 Bristol-Myers Squibb Co. Hair dyeing compositions containing 2-chloro- and 2,6-dichloro-4-aminophenol and phenylpyrazolones
EP1314418A1 (en) * 2001-11-27 2003-05-28 Dong Sung pharmaceuticals Co., Ltd. Hairdye composition including 1-phenyl-3-methyl-5-pyrazolone and method for obtaining the same
KR20030043210A (ko) * 2001-11-27 2003-06-02 동성제약주식회사 페닐메칠피라졸론을 함유하는 모발염모제 조성물 및 그제조방법
JP2003160453A (ja) * 2001-11-27 2003-06-03 Dongsung Pharm Co Ltd 毛髪染毛剤組成物及びその製造方法
WO2010123863A3 (en) * 2009-04-20 2011-08-25 The Procter & Gamble Company Keratin dyeing compositions comprising a radical scavenger and use thereof
JP2012524081A (ja) * 2009-04-20 2012-10-11 ザ プロクター アンド ギャンブル カンパニー ラジカルスカベンジャー及びキレート物質を含むケラチン染色組成物並びにその使用
US20110035886A1 (en) * 2009-04-20 2011-02-17 Guiru Zhang Keratin Dyeing Compositions Comprising a Radical Scavenger and a Chelant and Use Thereof
US7985266B2 (en) 2009-04-20 2011-07-26 The Procter & Gamble Company Keratin dyeing compositions comprising a radical scavenger and a chelant and use thereof
US7988740B2 (en) 2009-04-20 2011-08-02 The Procter & Gamble Company Keratin dyeing compositions comprising a radical scavenger and use thereof
WO2010123866A3 (en) * 2009-04-20 2011-08-18 The Procter & Gamble Company Keratin dyeing compositions comprising a radical scavenger and a chelant and use thereof
WO2010123863A2 (en) * 2009-04-20 2010-10-28 The Procter & Gamble Company Keratin dyeing compositions comprising a radical scavenger and use thereof
CN102405080A (zh) * 2009-04-20 2012-04-04 宝洁公司 包含自由基清除剂和螯合剂的角蛋白染色组合物及其用途
JP2012524080A (ja) * 2009-04-20 2012-10-11 ザ プロクター アンド ギャンブル カンパニー ラジカルスカベンジャーを含むケラチン染色組成物及びその使用
US20110035885A1 (en) * 2009-04-20 2011-02-17 Guiru Zhang Keratin Dyeing Compositions Comprising a Radical Scavenger and Use Thereof
WO2020259216A1 (en) * 2019-06-28 2020-12-30 L'oreal Composition for dyeing keratin fibres and use thereof
FR3110846A1 (fr) * 2019-06-28 2021-12-03 L'oreal Composition pour teindre des fibres de keratine et son utilisation
FR3110845A1 (fr) * 2019-06-28 2021-12-03 L'oreal Composition pour teindre des fibres de keratine et son utilisation
FR3111554A1 (fr) * 2019-06-28 2021-12-24 L'oreal Composition pour teindre des fibres de keratine et son utilisation
US11752082B2 (en) 2019-06-28 2023-09-12 L'oreal Cosmetic composition for the oxidative dyeing of keratin fibres
US11819562B2 (en) 2019-06-28 2023-11-21 L'oreal Composition for dyeing keratin fibres and use thereof
FR3128376A1 (fr) * 2021-09-29 2023-04-28 L'oreal Composition DE retardatEUR et nécessaire de teinture la coMPRenant

Also Published As

Publication number Publication date
FR1422838A (fr) 1966-01-03
CH433602A (fr) 1967-04-15
NL6501296A (ko) 1965-08-05
AT257841B (de) 1967-10-25
BE658983A (ko) 1965-07-28
DE1492072A1 (de) 1969-12-11
GB1065223A (en) 1967-04-12

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