US3558259A - Human hair dyeing with aminophenols - Google Patents

Human hair dyeing with aminophenols Download PDF

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Publication number
US3558259A
US3558259A US645520A US3558259DA US3558259A US 3558259 A US3558259 A US 3558259A US 645520 A US645520 A US 645520A US 3558259D A US3558259D A US 3558259DA US 3558259 A US3558259 A US 3558259A
Authority
US
United States
Prior art keywords
hair
aminophenol
hydroxy
methoxy
solution
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
US645520A
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English (en)
Inventor
Gregoire Kalopissis
Andree Bugaut
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.)
LOreal SA
Original Assignee
LOreal SA
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
Priority claimed from FR903703A external-priority patent/FR1374983A/fr
Priority claimed from FR940212A external-priority patent/FR84324E/fr
Application filed by LOreal SA filed Critical LOreal SA
Application granted granted Critical
Publication of US3558259A publication Critical patent/US3558259A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/415—Aminophenols
    • 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
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/32—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using oxidation dyes

Definitions

  • R is selected from the group consisting of hydrogen and alkyl
  • R is selected from the group consisting of hydroxy and alkyl
  • R, which can be in position or 6 on the ring is selected from the group consisting of hydrogen, halogen, hydroxy and alkyl.
  • This invention relates to improvements in processes for the dyeing of hair and to new compositions suitable for one step keratin fiber and hair dyeing.
  • a number of processes for dyeing keratinic fibers and notably hair are at present known, among the most commonly employed of these processes are those which are oxidation dyes whose coloration results from polymerization under oxidizing conditions.
  • the oxidation dyes employed are almost exclusively mixtures of aromatic diamines and aromatic aminophenols, generally known as bases, in combination with substances, generally called modifiers, such as substituted or unsubstituted monoand polyphenols. It is thus possible, by using a relatively limited number of aromatic bases and phenols, to obtain a fairly wide range of colorations, the proportions of the various constituents which enter into the composition of the dye bath being emperically varied.
  • the formation of haircoloring pigments from these mixtures results from a series of very complex chemical reactions which necessitate either the use of an oxidizing substance, hydrogen peroxide, or the presence of a substance having an alkaline reaction, which is generally ammonia. It is also known that by increasing the hydrogen peroxide and ammonia content there is obtained what is known as a decolorizing dye, there being simultaneously produced a decoloration of the hair to be dyed and a hair coloration in the desired shade.
  • each of the selected bases employed develops its own shade. Consequently, an extensive range of commercially necessary shades may be made available merely by employing a number of these products, the final shade obtained being the component of the individual shades of the starting materials.
  • the dyeing solution comprises no oxidizing agent and no modifier and its pH value is equal to or higher than 7, viz from 7 to 11, the necessary oxidation being induced by atmospheric oxygen.
  • EXAMPLE 8 Preparation of 6-methy1-4-hydroxy-2-aminophenol 6-methyl-4-methoxy-2-aminophenol is refluxed with a concentrated hydrobromic acid solution. After cooling, the hydrobromide of 6-methyl-4-hydroxy-2-aminophenol is filtered and separated. M.P. 225-228 C. (dec.).
  • a dyeing solution according to the invention is prepared by mixing:
  • a human hair dye composition comprising water and an effective amount of 6-brom0-4-methoxy-2-aminophenol having a pH of about 7 to 11.
  • a human hair dye composition comprising water and an efiective amount of 4-methyl-5-hydroxy-2-aminophenol having a pH of about 7 to 11.
  • a human hair dye composition comprising water and an effective amount of 4-methyl-S-hydroxy-2-methylaminophenol having a pH of about 7 to 11.
  • a human hair dye composition comprising water and an effective amount of 5-chloro-4-hydroxy-2-aminophenol having a pH of about 7 to 11.
  • a human hair dye composition comprising water and an effective amount of 5-methyl-4-hydroxy-2-aminophenol having a pH of about 7 to 11.
  • a human hair dye composition comprising water and an effective amount of 5-methoxy-4-hydroxy-2-aminophenol having a pH of about 7 to 11.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US645520A 1962-07-11 1967-06-12 Human hair dyeing with aminophenols Expired - Lifetime US3558259A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR903703A FR1374983A (fr) 1962-07-11 1962-07-11 Nouveau procédé de teinture des cheveux et nouvelles solutions tinctoriales utilisables à cet effet
FR940212A FR84324E (fr) 1963-07-03 1963-07-03 Nouveau procédé de teinture des cheveux et nouvelles solutions tinctoriales utilisables à cet effet
US6848870A 1970-08-31 1970-08-31

Publications (1)

Publication Number Publication Date
US3558259A true US3558259A (en) 1971-01-26

Family

ID=27246678

Family Applications (4)

Application Number Title Priority Date Filing Date
US645519A Expired - Lifetime US3666812A (en) 1962-07-11 1967-06-12 Diamino phenol hair dyeing compounds
US645520A Expired - Lifetime US3558259A (en) 1962-07-11 1967-06-12 Human hair dyeing with aminophenols
US645522A Expired - Lifetime US3546293A (en) 1962-07-11 1967-06-12 Amino phenols
US00068488A Expired - Lifetime US3738799A (en) 1962-07-11 1970-08-31 Dyeing human hair with 2-aminophenols

Family Applications Before (1)

Application Number Title Priority Date Filing Date
US645519A Expired - Lifetime US3666812A (en) 1962-07-11 1967-06-12 Diamino phenol hair dyeing compounds

Family Applications After (2)

Application Number Title Priority Date Filing Date
US645522A Expired - Lifetime US3546293A (en) 1962-07-11 1967-06-12 Amino phenols
US00068488A Expired - Lifetime US3738799A (en) 1962-07-11 1970-08-31 Dyeing human hair with 2-aminophenols

Country Status (6)

Country Link
US (4) US3666812A (ja)
BE (1) BE634643A (ja)
CH (1) CH415965A (ja)
DE (1) DE1492064A1 (ja)
GB (1) GB987342A (ja)
NL (1) NL295194A (ja)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3899288A (en) * 1971-12-02 1975-08-12 Jean Galerne Keratinic fibres oxidation dyeing compositions containing a carbonate of an alkali metal amino acid
JPS5176377A (en) * 1974-09-18 1976-07-01 Goodrich Co B F Jugotaifuchakuno haijohoho
US4031160A (en) * 1965-05-06 1977-06-21 Societe Anonyme Dite: L'oreal 2-Amino-4-hydroxy-5-chloro toluene and the hydrochloride thereof
US4035422A (en) * 1968-08-14 1977-07-12 L'oreal 2,6-Dimethyl-4-substituted amino phenol couplers
US4129414A (en) * 1975-03-03 1978-12-12 Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) Oxidation hair colorants containing water-soluble polyhalogen 3-aminophenols as couplers
US4212645A (en) * 1974-01-18 1980-07-15 Lever Brothers Company Hair dyeing composition containing an aryldiamine and a substituted catechol

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
LU56491A1 (ja) * 1968-07-15 1970-01-15
US3953462A (en) * 1973-10-29 1976-04-27 Xeerox Corporation Imaging process
FR2362116A1 (fr) * 1976-08-20 1978-03-17 Oreal Metaphenylenediamines et compositions tinctoriales les contenant
DE3027128A1 (de) * 1979-07-18 1981-02-12 Fuji Photo Film Co Ltd O-aminophenolverbindungen
DE3038284C2 (de) * 1980-10-10 1985-08-22 Wella Ag, 6100 Darmstadt Mittel und Verfahren zur oxidativen Färbung von Haaren
US4566876A (en) * 1983-03-10 1986-01-28 Clairol Incorporated Meta-phenylenediamine coupler compounds and oxidative hair dye compositions and methods using same
FR2637282B1 (fr) * 1988-09-13 1990-12-07 Oreal Para-aminophenols 2-substitues et leur utilisation pour la teinture des fibres keratiniques
US5202487A (en) * 1988-09-13 1993-04-13 L'oreal 2-substituted para-aminophenols and their use for dyeing keratinous fibres
FR2638453B1 (fr) * 1988-10-28 1991-06-07 Oreal Ortho-aminophenols 5-substitues, procede pour les preparer et leur utilisation pour la teinture d'oxydation des fibres keratiniques
US5409503A (en) * 1990-05-31 1995-04-25 Wella Aktiengesellschaft Oxidation hair dye with a content of 5-aminophenyl derivatives, process for oxidative dyeing of hair and new 5-aminophenol derivatives
US5041674A (en) * 1990-06-14 1991-08-20 Dowelanco Process and intermediates for the preparation of 2,6-difluoroaniline
DE4438129A1 (de) * 1994-10-27 1996-05-02 Schwarzkopf Gmbh Hans Neue substituierte 2,4-Diaminophenole, Verfahren zu ihrer Herstellung und Haarfärbemittel
DE19826456A1 (de) * 1998-06-13 1999-12-16 Schwarzkopf Gmbh Hans Neue 3,4-Diaminophenolderivate und deren Verwendung
MX2007001890A (es) * 2004-08-16 2009-02-12 Procter & Gamble Compuestos de fenol 2-(amino sustituido)-5, 6-sustituido, composiciones de teñido que las comprenden y su uso.
ATE463229T1 (de) * 2004-08-16 2010-04-15 Procter & Gamble Haarfärbemittel enthaltend 2-amino-3,5- substituierte phenolverbindungen und deren verwendung
WO2016051799A1 (ja) * 2014-10-01 2016-04-07 学校法人同志社 ２－アミノヒドロキノン誘導体及びタウ凝集阻害剤

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB479865A (en) * 1936-08-13 1938-02-14 Wilfred William Groves Manufacture of ortho-aminophenols
FR1137922A (fr) * 1955-11-25 1957-06-05 Oreal Procédé et composition pour teindre les cheveux vivants et fibres analogues
US3184387A (en) * 1955-11-25 1965-05-18 Oreal Process for dyeing hair with substituted 2, 4-diaminophenols
DE1096552B (de) * 1955-11-25 1961-01-05 Monsavon L Oreal Soc Mittel zum Faerben von lebenden Haaren
NL102837C (ja) * 1958-04-15

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4031160A (en) * 1965-05-06 1977-06-21 Societe Anonyme Dite: L'oreal 2-Amino-4-hydroxy-5-chloro toluene and the hydrochloride thereof
US4035422A (en) * 1968-08-14 1977-07-12 L'oreal 2,6-Dimethyl-4-substituted amino phenol couplers
US3899288A (en) * 1971-12-02 1975-08-12 Jean Galerne Keratinic fibres oxidation dyeing compositions containing a carbonate of an alkali metal amino acid
US4212645A (en) * 1974-01-18 1980-07-15 Lever Brothers Company Hair dyeing composition containing an aryldiamine and a substituted catechol
JPS5176377A (en) * 1974-09-18 1976-07-01 Goodrich Co B F Jugotaifuchakuno haijohoho
JPS5916561B2 (ja) * 1974-09-18 1984-04-16 ザ ビ− エフ グツドリツチ カムパニ− 重合体付着の排除方法
US4129414A (en) * 1975-03-03 1978-12-12 Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) Oxidation hair colorants containing water-soluble polyhalogen 3-aminophenols as couplers

Also Published As

Publication number Publication date
US3738799A (en) 1973-06-12
US3546293A (en) 1970-12-08
NL295194A (ja)
BE634643A (ja)
CH415965A (fr) 1966-06-30
GB987342A (en) 1965-03-24
DE1492064A1 (de) 1969-12-11
US3666812A (en) 1972-05-30

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