US2944869A - Process for dyeing keratinous material with ortho-diphenols - Google Patents

Process for dyeing keratinous material with ortho-diphenols Download PDF

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Publication number
US2944869A
US2944869A US709602A US70960258A US2944869A US 2944869 A US2944869 A US 2944869A US 709602 A US709602 A US 709602A US 70960258 A US70960258 A US 70960258A US 2944869 A US2944869 A US 2944869A
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Prior art keywords
solution
hair
grams
shade
rinsed
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US709602A
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English (en)
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Kalopissis Gregoire
Ghilardi Giuliana
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LOreal SA
Monsavon LOreal SA
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LOreal SA
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    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/347—Phenols
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic rings
    • 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
    • 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
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • 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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/30—Material containing basic nitrogen containing amide groups furs feathers, dead hair, furskins, pelts
    • D06P3/305—Material containing basic nitrogen containing amide groups furs feathers, dead hair, furskins, pelts with oxidation dyes

Definitions

  • This invention relates to the dyeing of hair and other keratinous substances.
  • oxidation dyes that is to say, compounds which give coloured derivatives only on oxidation. by means of a reactant such as hydrogen peroxide.
  • aromatic polyamines aminophenols and certain polyphenols, including triphenols, such as pyrogallol, hydroxyhydroquinone and. its nuclear substitution derivatives.
  • triphenols such as pyrogallol, hydroxyhydroquinone and. its nuclear substitution derivatives.
  • the shade in the dyeing by means of these oxidation dyes isgenerally effected: in alkaline medium and that the shade obtained is: generally not the final shade, but that it changes slowly and reaches this final shade only after 24 hours or evenmore.
  • the present invention provides a process for dyeing live hair and other keratinous substances by means of solutions of o-diphenols.
  • the process is readily performed, at room temperature, avoids the aforesaid disadvantages and achieves the final desired shade very rapidly, the coloration being fast to light, rubbing and shampooing.
  • a process of dyeing hair or other keratinous substance comprises applying thereto an aqueous or aqueous alcoholic solution of at least one ortho-diphenol having the following general formula:
  • R represents a hydrogen orhalogen atom or an aldehyde, alkyl, .cycloalkyl, aralkyl, carboxy, carboxyalkyl, alkoxy, nitroalkyl or nitrohydroxyalkyl. group or an amino acid residue, and developing. the shade by means of one or more inorganic oxidizing agents selected from ammonium or alkali metal iodates, periodates and persulphates.
  • the position of the nuclear carbon atom to which the group R is attached may differ in accordance with the isomers which can be actually obtained, but this carbon atom is preferably that in 4-position.
  • Ortho-diphenols of the above-defined type include notably, in addition to pyrocatechol (l), the following compounds: homopyrocat'e'chol (2), protocat'ec'huic acid (3),
  • the choice of the o-diphenol, or of the respective proportions of the various o-diphenols of the mixture which may be employed, depends principally, though not exclusively, upon the final shade desired.
  • the combined concentration of the o-diphenol or o-diphenols in the aqueous or aqueous alcoholic solution may be comprised Within a fairly wide range depending upon the desired shade. It will preferably be between about 0.01 mole and 1 mole of o-di'pheno'l per litre of solution.
  • the pH-value of the solutions which may be employed for. carrying out the process according to the invention may vary within a very wide range, e.g. between about 1 and 11. Together with the choice of the particular 0- diphenol or o-dip'henols used, the pH-value permits to control the final shade. Since the invention is not limited to the production of any particular shade, the pH-value at which the process is carried out is not a feature of the invention. Nevertheless it will be understood that, so far as hair-dyeing is concerned. the pH-value should not be such that the solution employed will irritate the scalp or impair the essential properties of the hair, such as its chemical structure, its elasticity and its mechanical strength. In. the case (referred to later herein) where the solution to be applied to hair contains any of the aforesaid oxidizing agents, the optimum choice of the pH-value is also dependent on the nature of this oxidizing agent.
  • the invention further includes the products of the process of the invention, such as human hair (not on the head) or other forms offhair, felts, furs, feathers and keratinous products generally.
  • an aqueous or aqueousalcoholic solution of the o-diphenol or o-diphenols is prepared, to which solution the inorganic oxidizing agent or agents specified are added at the time of application to the hair.
  • the pH of this solution may be adjusted to a neutral, acid or alkaline value by the addition of suitable reactants or the solution may be used as such, that is to say, without any component other than the o-diphenols and the oxidizing agents, the pH-value of the solution depending only on the respective proportions of each of these two types of components.
  • the solution is left in contact with the hair e.g. for five to 60 minutes, thoroughly rinsed with water, shampooed, rinsed again and dried.
  • the inorganic oxidizing agent or agents may be introduced into the o-di'phenol solution, either in the form of powder or in aqueous solution.
  • the operation is performed in two steps by first applying the solution of the o-diphenol or o-diphenols, free from any oxidizing agent, leaving this solution in contact with the hair e.g. for 5 to 60 minutes, in order to complete the impregnation, gently blotting oh the excess of liquid, optionally after rinsing with water, and then applying to the hair an aqueous solution of the oxidizing agent, and leaving it in contact with the hair for theperiod necessary for the development of the shade, generally from 5 to 20 minutes, the hair then being rinsed, shampooed', rinsed again and dried.
  • the oxidizing solution may be acidified by means of an organic or inorganic acid or by means of any suitable acid buffer.
  • an alkali metal or ammonium iodate or periodate it is preferable not to reduce the pH below 3 and not to use strong inorganic acids for obtaining the lowpH values.
  • the oxidizing solution may be made alkaline bymeans of any suitable alkaline reagent, for example by means of ammonia, an amine, or an ammonium or alkali metal carbonate or phosphate.
  • the concentration of the oxidizing agent in the solution containing it may be varied between wide limits depending. upon the shade to be obtained and do pending upon the solubility of the oxidizing agents used.
  • the quantity of oxidizing agent to be employed corresponds to about 0.5 to 10 grams per 100 cc. of the o-diphenol solution employed, whether this solution contains or does not contain the oxidizing agent, the volumes of o-diphenol solution and/ or of oxidizing agent to be employed being determined by the bulk of hair or by the quantity of other keratinous product to be dyed.
  • the reactants may be applied in the form of creams, pastes or jellies, the adjustment to the required consistency being effected by any means usual in hair dyeing.
  • Example I A solution having the following composition is prepared:
  • Example I A solution having the following composition is prepared:
  • the hair is dyed a beautiful grey-black.
  • Example X 1 gram of sodium iodate is introduced into a solution having the following composition:
  • Example XII A solution having the following composition is prepared:
  • Example XIII A. solution having the following composition is prepared:
  • Example XIV A solution having the following composition is applied to nearly white live hair:
  • Example X V The following solution is prepared:
  • Example X VI Naturally white live hair is impregnated with the following solution:
  • Example VII A solution having the following composition is prepared:
  • the pH-value of this solution is 3.1. 7.2 grams of sodium persulphate'are added to this solution, which is immediately applied to naturally white live hair. After 5 minutes, the pH-value of the solution close to the cortex of the hair is 2.8. After a total impregnation time of 25 minutes, the hair is briefly rinsed, shampooed,
  • the pH-value of the solution. is 2.8.
  • 2 grams of sodium iodate are added.
  • the solution is left in contact with the hair for 15 minutes, during which it is observed that the pH-value of the part of the solution close to the hair does not vary.
  • the hair is then briefly rinsed, shampooed, rinsed again and dried.
  • the shade thus obtained is ash-chestnut.
  • Example XIX The following composition is prepared:
  • the pH-value of this mixture is 4. 4 grams of sodium iodate are added to this composition which is immediately applied to naturally white live hair. After contact for 15 minutes, during which it is observed that the pH of the solution close to the hair does not vary, the hair is rinsed with tapwater and dried. An ash-chestnut shade is obtained.
  • a process for dyeing hair and other keratinous ma terials which comprises applying thereto an aqueous solution consisting of at least one orthodiphenol of the general formula:
  • R is selected from the class consisting of the hydrogen atom, the halogen atom, aldehyde, alkyl, carboxy, alkoxy, nitro-hydroxyalkyl and alpha amino propanoic groups, and an oxidizing agent selected from the class consisting of ammonium and alkali metal iodates, periodates and persulphates.
  • a process for dyeing hair and other keratinous materials which comprises applying thereto an aqueous solution consisting, in the global proportion of 0.1 to 1.0 mole per litre, of at least one orthodiphenol of the general formula:
  • R is selected from the class consisting of the hydrogen atom, the halogen atom, aldehyde, alkyl, carboxy, alkoxy, nitro-hydroxyalkyl and alpha amino propanoic groups, said solution also containing a freshly added oxidizing agent selected from the class consisting of ammonium and alkali metal iodates, periodates and persulphates, the quantity of oxidizing agent being 0.5 to grams per litre of said orthodiphenol solution.
  • a process for dyeing hair'- and other keratinous materials which comprises applying thereto an aqueous solution consisting, in the global proportion of 0.1 to 1.0 mole per litre, of at least one orthodiphenol of the general formula:
  • R is selected from the class consisting of the hydrogen atom, the halogen atom, aldehyde, alkyl, carboxy, alkoxy, nitro-hydroxyalkyl and alpha amino propanoic groups and thereafter applying thereto an oxidizing agent selected from the class consisting of ammonium and alkali metal iodates, periodates and persulphates, the quantity of oxidizing agent being 0.5 to 10 grams per litre of said orthodiphenol solution.
  • a process for dyeing hair and other keratinous materials which comprises applying thereto an aqueous solution consisting, in the global proportion of 0.1 to 1.0
  • R is selected from the class consisting of the hydrogen atom, the halogen atom, aldehyde, alkyl, carboxy, alkoxy, nitro-hydroxyalkyl and alpha amino propanoic groupsand thereafter applying thereto a solution of an oxidizing agent selected from the class consisting of ammonium and alkali metal iodates, periodates and persulphates, the quantity of oxidizing agent being 0.5 to 10 grams per litre of said orthodiphenol solution, and allowing said oxidizing solution to remain in contact with the hair for 5.20 minutes.
  • a process for dyeing hair and other keratinous materials which comprises applying thereto an aqueous solution of pH 3 to 11 consisting, in the global proportion of 0.1 to 1.0 mole per litre, of at least one orthodiphenol of the general formula:
  • R is selected from the class consisting of the hydrogen atom, the halogen atom, aldehyde, alkyl, carboxy, alkoxy, nitro-hydroxyalkyl and alpha amino propanoic groups, said solution also containing a freshly added oxidizing agent selected from the class consisting of ammonium and alkali metal iodates, periodates and persulphates, the quantity of oxidizing agent being 0.5 to 10 grams per litre of said orthodiphenol solution.
  • a process for dyeing hair and other keratinous materials which comprises aplying thereto an aqueous solution of pH 3 to 11 consisting, in the global proportion of 0.1 to 1.0 mole per litre, of at least one orthodiphenol of the general formula:
  • R is selected from the class consisting of the hydrogen atom, the halogen atom, aldehyde, alkyl, carboxy, alkoxy, nitro-hydroxyalkyl and alpha amino propanoic groups and thereafter applying thereto an aqueous References Cited in the file of this patent UNITED STATES PATENTS 2,539,202 Peck Ian. 23, 1951 FOREIGN PATENTS 745,144 Great Britain Feb. 22, 1956 OTHER REFERENCES Kass: Am. Perf. and Aromatics, August 1956, pp. 34-37.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Cosmetics (AREA)
US709602A 1957-01-21 1958-01-17 Process for dyeing keratinous material with ortho-diphenols Expired - Lifetime US2944869A (en)

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CH (1) CH345629A (US06168776-20010102-C00041.png)
DE (1) DE1106925B (US06168776-20010102-C00041.png)
GB (1) GB831851A (US06168776-20010102-C00041.png)
NL (1) NL224239A (US06168776-20010102-C00041.png)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3617167A (en) * 1965-08-05 1971-11-02 Therachemie Chem Therapeut Methods and compositions containing 4-aminopyrazolones for the dyeing of human hair
US4391603A (en) * 1980-04-17 1983-07-05 L'oreal Hydroxyl derivatives of benzaldehyde for coloring keratin fibres in the absence of oxidizing agent
US4479803A (en) * 1979-09-28 1984-10-30 Wella Aktiengesellschaft Agent for oxidative dyeing of hair
US4708865A (en) * 1986-08-21 1987-11-24 Turner Janet N Method and composition for artificially tanning the human epidermis
US5441542A (en) * 1991-09-26 1995-08-15 Clairol Incorporated Process and kit for post-oxidative treatment of permanently dyed hair
US5584889A (en) * 1993-12-27 1996-12-17 Clairol Incorporated Oxidative hair dyeing process with dihydroxybenzenes and aminoethanethiols
EP1743620A1 (en) * 2004-04-27 2007-01-17 Takasago International Corporation Cosmetic hair prepartion composition
CN109846742A (zh) * 2019-02-12 2019-06-07 西南医科大学 一种多色无毒染发剂及其制备方法和染发方法

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3931912A (en) * 1971-08-12 1976-01-13 The Gillette Company Two-part hair dye or hair bleach package
CA1255232A (en) * 1984-04-09 1989-06-06 Walter C. Herlihy Hair dye composition and process for using the same
DE3628397C2 (de) * 1986-08-21 1994-06-09 Goldwell Ag Mittel zum oxidativen Färben von Haaren, Verfahren zu seiner Herstellung und Verwendung des Mittels

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2539202A (en) * 1947-12-11 1951-01-23 Samuel M Peck Method of dyeing animal fibers
GB745144A (en) * 1953-01-01 1956-02-22 Gillette Industries Ltd Improvements in or relating to the dyeing of hair and other keratinous materials

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE663781C (de) * 1936-05-08 1938-08-13 I G Farbenindustrie Akt Ges Haarfaerbemittel
AT179384B (de) * 1951-04-19 1954-08-25 Union Francaise Commerciale Et Industrielle Sa Verfahren zur Herstellung eines unschädlichen Haarfärbemittels
AT188027B (de) * 1951-11-19 1956-12-27 Union Francaise Commerciale Et Industrielle Sa Verfahren zur Herstellung eines unschädlichen Haarfärbemittels
GB745531A (en) * 1953-01-01 1956-02-29 Gillette Industries Ltd Improvements in or relating to the dyeing of hair and other keratinous material
GB745532A (en) * 1953-01-01 1956-02-29 Gillette Industries Ltd Improvements in or relating to the dyeing of hair and other keratinous material
FR1124393A (fr) * 1955-05-17 1956-10-09 Gillette Industries Ltd Perfectionnements aux procédés pour la teinture des cheveux

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2539202A (en) * 1947-12-11 1951-01-23 Samuel M Peck Method of dyeing animal fibers
GB745144A (en) * 1953-01-01 1956-02-22 Gillette Industries Ltd Improvements in or relating to the dyeing of hair and other keratinous materials

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3617167A (en) * 1965-08-05 1971-11-02 Therachemie Chem Therapeut Methods and compositions containing 4-aminopyrazolones for the dyeing of human hair
US4479803A (en) * 1979-09-28 1984-10-30 Wella Aktiengesellschaft Agent for oxidative dyeing of hair
US4391603A (en) * 1980-04-17 1983-07-05 L'oreal Hydroxyl derivatives of benzaldehyde for coloring keratin fibres in the absence of oxidizing agent
US4708865A (en) * 1986-08-21 1987-11-24 Turner Janet N Method and composition for artificially tanning the human epidermis
US5441542A (en) * 1991-09-26 1995-08-15 Clairol Incorporated Process and kit for post-oxidative treatment of permanently dyed hair
US5584889A (en) * 1993-12-27 1996-12-17 Clairol Incorporated Oxidative hair dyeing process with dihydroxybenzenes and aminoethanethiols
US5980586A (en) * 1993-12-27 1999-11-09 Bristol-Myers Squibb Company Oxidative hair dyeing process with dihydroxybenzenes and aminoethanethiols
EP1743620A1 (en) * 2004-04-27 2007-01-17 Takasago International Corporation Cosmetic hair prepartion composition
US20070166256A1 (en) * 2004-04-27 2007-07-19 Takasao International Corporation Hair cosmetic composition
EP1743620A4 (en) * 2004-04-27 2012-04-25 Takasago Perfumery Co Ltd COMPOSITION OF A HAIR COSMETIC PREPARATION
CN109846742A (zh) * 2019-02-12 2019-06-07 西南医科大学 一种多色无毒染发剂及其制备方法和染发方法

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NL224239A (US06168776-20010102-C00041.png)
CH345629A (fr) 1960-04-15
DE1106925B (de) 1961-05-18
GB831851A (en) 1960-04-06

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