US3642429A - Cosmetic composition for treating hair - Google Patents

Cosmetic composition for treating hair Download PDF

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Publication number
US3642429A
US3642429A US770089A US3642429DA US3642429A US 3642429 A US3642429 A US 3642429A US 770089 A US770089 A US 770089A US 3642429D A US3642429D A US 3642429DA US 3642429 A US3642429 A US 3642429A
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US
United States
Prior art keywords
hair
formula
compound
composition
acid
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
US770089A
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English (en)
Inventor
Gregoire Kalopissis
Jean-Louis Abegg
Guiliana Ghilardi
Henri Philippe De Beaulieu
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LOreal SA
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LOreal SA
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Publication of US3642429A publication Critical patent/US3642429A/en
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/25—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • 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
    • A61K8/42—Amides
    • 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
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • 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
    • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
    • 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
    • A61Q5/04—Preparations for permanent waving or straightening the hair
    • 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
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
    • C07C275/06—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
    • C07C275/14—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C305/00—Esters of sulfuric acids
    • C07C305/02—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
    • C07C305/04—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated
    • C07C305/06—Hydrogenosulfates

Definitions

  • a cosmetic composition for treating hair comprising an electrophile methylol amine and a urein compound, one or both of which contain a chemical group-which has cosmetic properties; and a method of treating hair with this composition.
  • Y(NH(l'TNHz)n .s .a.A Y-. X in which n 1 or 2, X is O, S or NH and Y is a disulfide, carboxylic acid, tertiary or quaternary amine or SH group which has cosmetic properties.
  • This invention relates to a cosmetic composition which ,makes it possible to improve the condition of human hairand to impart thereto certain properties which are useful when it is to be subjected to a subsequent cosmetic treatment.
  • compositions comprising methylol products which are more stable than dimethylolurea and dimethylolthiourea be used, which products yield excellent results due to polymerization in'the keratin chain and condensation of these compounds on the reactive groups of the keratin, thereby in practice imparting to the treated hair greater strength, an improved appearance and, in general, attractive cosmetic properties.
  • This phenomenon is particularly valuable when the compound of the urein type contains a cosmetic component attached to the nitrogen which is finally embedded inside the hair when the methylol compounds are polymerized in the keratin in the presence of these particular urein compounds.
  • R represents either hydrogen, or a lower alkyl radical
  • E represents a radical which is sufficiently electrophile to assure that the entire g'rou molecule
  • E is selected from among the following groups:
  • urein-type compounds which may be used in the cosmetic compositions according to the invention are:
  • the number of urea groups carried by the urein-type compound lies between 0.2 and 3 times and preferably from 0.5 to 1.0 times the number of hydroxyrnethyl or alkoxy methyl groups carried by the methylol compound.
  • the composition also contains an acid catalyst, which may bea rnineralor organic acid used in the cosmetic fieldor a salthaving anacid reaction.
  • an acid catalyst which may be a rnineralor organic acid used in the cosmetic fieldor a salthaving anacid reaction.
  • composition according to the invention may take the form of an aqueous or hydroalcoholic solution and serve as a setting lotion which may comprise any additives conventionallyincluded in such lotions
  • the composition according to the'invention may also .take the form of a gel or cream, or be packaged in aerosolf'orm.
  • composition according to the invention may also contain any ingredients conventionally used incosmetics, such as dyes, perfumes, surface-active agents, swelling agents, resins, etc.
  • the composition may be packaged in two phases, a solid phase containing the methylol compounds, and the urein-type compounds, and a liquid phase which is an aqueous or hydroalcoholic solution, which may contain conventional cosmetic additives and/or an acid catalyst.
  • the solid phase contains only the methylol compounds, and the urein-type compounds are in aqueous or hydroalcoholic solution.
  • the cosmetic composition according to the invention is prepared at the moment of use by dissolving the solid phase in the liquid phase. This rnethod of packaging makes it possible to avoid the premature polycondensations which may take place during prolonged storage of the composition.
  • the solid phase or the aqueous phase of the cosmetic composition packaged in this manner may also contain a salt of sulfurous acid, such as sodium metabisultite.
  • a further object of the present invention is to provide a method of treating hair characterized by the fact that the hair is impregnated with the above-described composition, and then dried by heating, after having first been rinsed.
  • the cosmetic composition does not itself contain the acid catalyst necessary to bring about polycondensation of the methylol compounds and the urein-type compounds in the keratinic fiber, and this acid catalyst is instead applied to the hair either before or after the composition according to the invention.
  • lt is a further object of the present invention to provide the new article of manufacture .which consists of a compound responding to the following formula:
  • X represents hydrogen, sulfur, or an NH radical
  • Y is a. radical comprising a chemical-functionwhich enables it to serve a cosmeticrpurpose such, for example, as a disulfide function, a carboxylic acid function, a tertiaryor .quatemary amine function, a .fatty chain, or an SH function.
  • the present invention has ,as its particular object the production of a new-article of manufactureconsisting of a compound selected from thegroup consisting of:
  • N-methyl-dipropylurea (dimethyl-copra-ethylurea)-ammonium-chloride, N,N-carbamyl cystamine, N-carbamyl-cystamine hydrochloride, N,N'-(dimethyl-ethylurea)- cystamine dichloride, (diethyl-methyl-ethylurea)-ammonium iodide, diethylamino ethylurea (dimethyl, .dipropylurea) ammonium methosulfate,and N-carbamyl cysteamine.
  • a further object of the present invention is to provide a new method of preparing urein-type compounds as described above, characterizedby the fact that a cyanate or an alkaline thiocyanate .is reacted with amine compounds having a Y- grouprepresenting the cosmetic additive in question attached to the nitrogen.
  • the amine which carries the cosmetic additive attached to its nitrogen atom is reacted .with urea, to produce the corresponding urein by elimination of ammonia.
  • a tertiary amine having a cosmetic additive attached to its nitrogen atom is reactedwith a halogenoalkylurea.
  • EXAMPLE 1 An aqueous solution of the following composition is applied to natural hair which has first been washed and dried:
  • the hair is then set in aconventional manner by winding it up on rollers and drying it under a hood at a temperature of 45 -50 C. This attaches to the keratin of the hair an acid compound having the following statistical formula:
  • This operation permits the attachment to the keratin of a compound of the disulfide typewhich is soluble in reducing media and has substantially the following composition:
  • n lies between 0.5 and l inclusive.
  • the hair is strengthened and the set holds well and is sprin- 8% Moreover, the presence of artificial disulfide bonds in the kcrutinic libcr makes it possible to subsequently permanently wave or bleach the hair under improved conditions.
  • the hair is then set in a conventional manner, keeping it for about 30 minutes at a temperature between 45 and 50 C.
  • monomethylolurea 8 g. (dimethyl-copra-ethylurea)-ammonium chloride 2 g. acetic acid q.s.p. pH 3 water q.s.p. I00 cc.
  • EXAMPLE 5 Preparation of (dimethyl-dipropylurea)-amrnonium methosulfate
  • the first step is to prepare N-methyl-dipropylurea by reacting potassium cyanate with N-methyl-dipropylamine dihydrochloride in stoichiometric proportions. The reaction is carried out in aqueous solution at a temperature of 90 C. for 2 hours.
  • the product is dried by evaporation and then extracted with hot absolute ethanol.
  • the result is a white powder titrating 95 a temperature between percent of the theoretical amount of total ry amines.
  • N-methyl-dipropylurea is suspended in l liter of absolute ethanol.
  • a stoichiometric quantity, or a slight excess, of methyl sulfate is added slowly, while stirring.
  • the resulting quaternary compound separates from the alcoholic layer, in the form of a thick oil which is vacuum dried and may be purified by washing with ether. The yield is practically quantitative'.
  • the resulting paste is washed with 450 cc. of chloroform, and again dried on phosphoric anhydride.
  • the final result is a 98 percent yield of a solid white product titrating about percent of the theoretical value of disulfide and ionized chloride.
  • a process for treating human hair which comprises applying to said hair a composition containing in a solvent selected from the group consisting of water and'hydroalcoholic solution:
  • X is selected from the group consisting of O, S and NH
  • n is l or 2 and when n is 1, Y is selected from the group conand when n is 2, Y is selected from the group consisting of *(CH2)al T( 2)a-, 2)2 H2)Z CH CH said composition containing said compound (I) in a concentration ranging from 0.5 to 12 percent by weight, polycondensing said compound and said urein compound on said hair in the presence of an acid catalyst in amounts sufficient to polycondense said compound and said urein compound, rinsing the hair and then drying the same.
  • said acid catalyst is selected from the group consisting of acetic acid, phosphoric acid and hydrochloric acid.
  • said urein compound is r a compound having the formula N-carbamyl N-carbamyl cysteamine, cystamine hydrochloride, N,N dimethyl-ethylurea )cystamine dichloride, (diethyl-methyl-ethylurea )-ammonium iodide, diethylamino ethylurea and (dimethyl-dipropylurea)-ammonium methosulfate.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • 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)
US770089A 1967-10-26 1968-10-23 Cosmetic composition for treating hair Expired - Lifetime US3642429A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
LU54741 1967-10-26

Publications (1)

Publication Number Publication Date
US3642429A true US3642429A (en) 1972-02-15

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ID=19725387

Family Applications (1)

Application Number Title Priority Date Filing Date
US770089A Expired - Lifetime US3642429A (en) 1967-10-26 1968-10-23 Cosmetic composition for treating hair

Country Status (10)

Country Link
US (1) US3642429A (it)
AT (1) AT295752B (it)
BE (1) BE722886A (it)
CA (1) CA933094A (it)
CH (1) CH520503A (it)
FR (1) FR1598172A (it)
GB (1) GB1253235A (it)
IT (1) IT1036013B (it)
LU (1) LU54741A1 (it)
NL (1) NL156598B (it)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001006994A1 (en) * 1999-07-23 2001-02-01 Unilever Plc Method of reducing colour loss from dyed hair using organic amino compounds
US20090056745A1 (en) * 2007-08-27 2009-03-05 Applied Materials, Inc. Wet clean process for recovery of anodized chamber parts

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU461954B2 (en) * 1970-11-16 1975-06-12 Colgate-Palmolive Company Cosmetic compositions
DE3122482A1 (de) * 1980-06-06 1982-04-08 L'Oreal, 75008 Paris Quarternaere bis-ammoniumderivate enthaltende mittel zur behandlung keratinischer materie und nicht-keratinischer, natuerlicher oder synthetischer textilstoffe, verfahren zur anwendung der genannten mittel sowie neue hierbei verwendete verbindungen

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3232933A (en) * 1960-04-30 1966-02-01 Dehydag Gmbh 1-thiocarbamyl-2-imidazolidinethiones and a process for their preparation
US3349000A (en) * 1963-01-24 1967-10-24 Joos Bernhard Process for treating human nails and hair with dimethylol thiourea compositions
US3534135A (en) * 1965-12-23 1970-10-13 Wella Ag Method for setting hair with dithiourea and derivatives thereof

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3232933A (en) * 1960-04-30 1966-02-01 Dehydag Gmbh 1-thiocarbamyl-2-imidazolidinethiones and a process for their preparation
US3349000A (en) * 1963-01-24 1967-10-24 Joos Bernhard Process for treating human nails and hair with dimethylol thiourea compositions
US3534135A (en) * 1965-12-23 1970-10-13 Wella Ag Method for setting hair with dithiourea and derivatives thereof

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001006994A1 (en) * 1999-07-23 2001-02-01 Unilever Plc Method of reducing colour loss from dyed hair using organic amino compounds
US6551361B1 (en) 1999-07-23 2003-04-22 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Method of hair treatment using organic amino compounds
US20090056745A1 (en) * 2007-08-27 2009-03-05 Applied Materials, Inc. Wet clean process for recovery of anodized chamber parts

Also Published As

Publication number Publication date
LU54741A1 (it) 1969-06-27
NL6815223A (it) 1969-04-29
NL156598B (nl) 1978-05-16
CA933094A (en) 1973-09-04
DE1803709B2 (de) 1977-07-07
GB1253235A (it) 1971-11-10
CH520503A (fr) 1972-03-31
IT1036013B (it) 1979-10-30
BE722886A (it) 1969-04-25
DE1803709A1 (de) 1969-06-04
AT295752B (de) 1972-01-25
FR1598172A (it) 1970-07-06

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