Classifications

• • 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
  • 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
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
• • 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
  • C07C323/39—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 at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
  • C07C323/43—Y being a hetero atom
  • C07C323/44—X or Y being nitrogen atoms
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
  • A61K2800/95—Involves in-situ formation or cross-linking of polymers
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S424/00—Drug, bio-affecting and body treating compositions
  • Y10S424/01—Aerosol hair preparation
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S424/00—Drug, bio-affecting and body treating compositions
  • Y10S424/02—Resin hair settings

Definitions

• aryl chains such as benzene
• NR chains in which 2 represents a substituted or unsubstituted, straight or branched chain hydrocarbon having one to six carbon atoms, such as alkyl, alkenyl, etc., R represents a hydrogen atom or hydrocarbon group, which may be substituted. (These substitutions may be of very different types, such as carboxyl, amine, etc.)
• Y, and Y which may or may not be identical, represent a hydrogen atom or a hydroxyl group (in the case of free methylols), which may, in certain cases, be etherified, or converted by the Mannich reaction with a secondary amine, but only one of Y, and Y, may represent ahydrogen atom.
• R represents an alkyl radical having up to six carbon atoms.
• the bivalent metal may be selected from the group consisting of tin ll, chromium ll, nickel, manganese ll, cadmium, zinc, antimony ll, barium, strontium, calcium, magnesium, cobalt 11, iron ll, etc.
• the thiolate of I the thiol which can be transformed into N-methylol is precipitated by adding said thiol little by little to a solution of a bivalent metallic salt such as Zu,Cu,Cd,Ba,Sr,Ca salts.
• N-methylol group of said thiolate is esterified or subjected to a Mannich reaction.
• the new compounds which have just been described have a bifunctional structure which imparts thereto properties which are particularly valuable in the cosmetic field.
• compositions have both a thiolate group and at least one methylol group, each of these groups having a reactivity with keratinic fiber which imparts particularly advantageous properties to the composition.
• the invention relates to various methods of treating the hair, characterized by the fact that the hair is impregnated with compositions containing compounds according to formula l in proportions varying between 0.1 and percent by weight.
• the neutralization step of a pennanent wave or a two-step permanent set is carried out by impregnating the hair, while it is rolled up on curlers, with a composition comprising at least one compound according to formula l at a concentration between 0.05 moles and 0.4 moles per liter, the pH of the composition being preferably alkaline and between 8 and 10.
• the process according to the invention is particularly useful in fixing permanent sets.
• the hair is wound up on setting rollers of average diameter, after having been impregnated with a reducing solution, such as a solution of thiol utilized in permanent waving.
• a reducing solution such as a solution of thiol utilized in permanent waving.
• the method of fixing the permanent set according to the invention is particularly advantageous in the present case because in order to fix the set it sufiices to apply a solution of the compound of formula to hair which has first been reduced and rinsed, and to dry the hair under a dryer without rinsing it. This results in excellent chemical fixation and an addition of polymers which results from the polymerization of the compounds according to formula 1.
• a permanent hair set may be produced by following a new technique made possible by using thiolates according to the invention. This consists in treating the hair with a reducing solution without putting it up on curlers, rinsing it, impregnating it with a thiolate solution according to the invention, then winding the hair up on setting rollers, and finally drying the hair.
• the compounds of formula I also make it possible to recondition hair which has been degraded as the result of bleaching, for example.
• the first step of a permanent waving process consists in applying to a head of hair which has been strongly bleached an aqueous solution, which is prepared at the moment of use, and contains a mixture of at least one compound according to formula l and ethylene diamine tetracetic acid, the pH of the solution being brought to between 8 and 10.
• the second step of this permanent waving process may be carried out in a conventional manner.
• This process has, moreover, a particular advantage in that it makes it possible to prepare a permanent waving powder in a simple manner, since the thiolatei according to the invention keep much better when exposed to the air then conventional thiols do.
• such hair may be protected from the adverse effects of permanent waving liquids by applying thereto a solution containing at least one compound according to formula I, and then drying the hair before permanently waving it in a conventional manner.
• bleached hair may be permanently set by impregnating it with a composition comprising at least one compound of formula I, and having a pH value and 10, after which the hair is rinsed and set in a conventional manner.
• composition adapted to be used in carrying out the above described processes, which composition is characterized by the fact that it comprises at least one compound according to formula I in a concentration between 0.1 and 20 percent and has a pH value between 7 and 10 and preferably between 8 and 10.
• compositions according to the invention may take the form of an aqueous solution, a cream, a gel or an aerosol, depending on which method of application is most appropriate to the end desired. They may also take the form'of a powder which is dissolved at the moment of use.
• compositions according to the invention may also contain' various active ingredients conventionally included in cosmefics such as swelling agents, surface-active agents, dyes, and perfumes. These various agents may be selected to suit the particular treatment which is to be carried out by means of the composition.
• a further object of the present invention is to provide a method of coating metals characterized by the fact that a film of a solution containing at least one thiolate according to for mula l is applied to a metallic surface which has first been washed and degreased. The metallic surface is then left at the ambient temperature for a moment, after which it is put in an oven for from 1 to 48 hours until it sets to form a varnish type coating.
• metals and alloys which may be most advantageously coated in accordance with the invention are copper, brass and steel.
• the starting reactant used in this preparation is thioacetamide, which may be obtained by aminolysis of ethyl thioglycolate.
• the reaction producing the thiolate is the following:
• the resulting product is washed with 3 liters of acetone in small fractions, the precipitate is malaxated and dried after each washing.
• the resulting product is dried by spreading it out in thin layers and being left to stand for 3 to 4 days while exposed to the air.
• the yield of the reaction is 95 percent.
• cysteamine cadmium thiolate is prepared by carrying out the following reaction:
• the yield of the reaction is 83 percent.
• composition is prepared by the following process:
• the resulting mixture is heated while being agitated for 2 hours at 80 C.
• the cadmium thiolate dissolves.
• the mixture is left to cool at room temperature and then poured drop by drop into a liter of acetone at 0 C.
• the resulting precipitate is left to stand for about 2 hours at room temperature.
• This precipitate is then filtered on fritted No. 2 glass and washed copiously with acetone, using 100 ml of acetone at a time. The product is then vacuum dried until the traces of acetone disappear.
• This compound is prepared by the following process:
• 35 g ofureide is suspended in 100 ml ofwater. 15 g of40 percent formol and 17.4 g of morpholine are added while The water of the solution, which is quite viscous, is evaporated under vaeuum,in the presence of P,O,.
• a solid white product is obtained after two days of vacuum drying. The yield is 93 percent.
• This varnish may be very easily removed by means of dilute acid or a solution of ethylenediamine tetracetic acid.
• EXAMPLE 2 A female head of leave human hair was sharnpooed, dried, rolled up on setting rollers of normal diameter while each lock is successively impregnated with a conventional permanent waving solution.
• the hair is again saturated and left for 10 to 20 minutes under a hood.
• the hair is then rinsed again, and a 5 percent solution of a compound having the following formula, which is prepared at the moment of use, is applied to the hair, after being brought to Ph 9.5 by the addition of ammonia.
• the hair is then immediately placed under a drier and dried in a conventional manner. It is removed from the rollers and combed.
• EXAMPLE 3 A mixture of cadmium-bis-IN-hydroxymethyl-carbamoylmethylthiolate] and E.D.T.A. is dissolved in an ammonia solution at the moment of use. After mixing, the composition contains:
• EXAMPLE 4 One side of a head of previously bleached hair is treated with a 2 percent solution of cadmium-bis-[( N-hydroxymethylcarbamoyl-methylthiolate] having a pH of 8.3. It is then placed under a hood for several moments to dry the hair and polymerize the compound.
• a shampoo is prepared at the moment of use by mixing 5 g of cadmium-bis-[N-hydroxymethyl-carbamoyl-methylthiolate] with a solution containing:
• a permanent waving liquid having an alkaline or neutral pH may, for example, be a commercial permanent waving solution.
• a liquid may, for example, be a commercial permanent waving solution.
• the hair is rinsed and an aqueous solufion prepared at the moment of use is applied. This contains 5 or 10 percent of cadmium-bis-l N-hydroxymethyl-carbamoyl-methylthiolate and has a pH of 9.5.
• the hair is wound up on setting rollers, dried, and combed.
• the detergents can be alkyl sulfates alkyl ether sulfates, alkyl polyether sulfates, alkyl sulfonates, in which the alkyl groups have eight to 18 carbon atoms, sulfated monoglycerides, sulfonated monoglycerides, sulfated alkanolarnides, sulfonated alkanolamides, soaps of fatty acids, monosulfosuccinates of fatty alcohols, the products of the condensation of fatty acids with methyl-taurine, the products of the condensation of fatty acids with sarcosine, the products of the condensation of fatty acids with a protein hydrolysate; cationic detergents such as long chain quaternary ammonium, esters of fatty acids and of amine alcohols, polyether amines; non-ionic detergents such as the esters of polyols and sugars, the products of the condensation
• Cosmetic carriers which can be utilized can be water-alcohol, gel, cream and aerosol.
• a permanent wave a the hairs are rolled on curlers of little diameter b. the hairs are rinsed with water after neutralization c. the hairs do not need to be dried on curlers after neutralization.
• the hairs are rolled on rollers of middle diameter b. the hairs are not rinsed after neutralization c. the hairs are dried on the rollers.
• a cosmetic composition for human hair comprising an aqueous solution of O. l-20 percent by weight of a compound having the formula wherein:
• Me is selected from the group consisting of zinc and cadmiurn
• X and X are selected from the group consisting of carboncarbon bond
• Y and Y are selected from the group consisting of said composition having a pH of 8-10.
• composition of claim 1 wherein said compound is selected from the group consisting of cadmium-bis-[N- hydroxymethyl-carbarnoyl-methylthiolate], zinc-bis-[N- hydroxymethyl-carbamoyl-methylthiolate cadmium-bis-[ N morpholinomethylureido-methylthiolate] cadmium-bis-[ 2- (N '-hydroxymethylureido)-ethylthiolate] cadmium-bis-l 2( N -morpholinomethylurdeido )-ethylthiolate] cadmium-bis-( N morpholinomethyl-carbamoyl-methylthiolate) and cadmiumbis-I 2-methoxycarbonyl-2-( N '-morpholinomethylureido thyl-thiolate].
• composition of claim 1 ethylenediamine tetracetic acid.
• a process for treating human hair comprising impregnating said hair with an eflective amount of a composition comprising an aqueous solution of 0.1-20 percent by weight of a compound having the formula also containing SCHzXzCONH-CH2Y:
• Me is selected from the group consisting of zinc and cadmiurn
• X and X are selected from the group consisting of carboncarbon bond

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• Health & Medical Sciences (AREA)
• Organic Chemistry (AREA)
• Life Sciences & Earth Sciences (AREA)
• Chemical & Material Sciences (AREA)
• Veterinary Medicine (AREA)
• Animal Behavior & Ethology (AREA)
• General Health & Medical Sciences (AREA)
• Public Health (AREA)
• Epidemiology (AREA)
• Birds (AREA)
• Cosmetics (AREA)
• Chemical Treatment Of Metals (AREA)
• Chemically Coating (AREA)

Applications Claiming Priority (1)

Publications (1)

Family

ID=19725506

Family Applications (1)

Country Status (4)

Cited By (1)

Citations (1)

• 1968
  • 1968-02-20 LU LU55515D patent/LU55515A1/xx unknown
• 1969
  • 1969-02-14 FR FR6903713A patent/FR2002220A1/fr not_active Withdrawn
  • 1969-02-19 US US800721A patent/US3674038A/en not_active Expired - Lifetime
  • 1969-02-20 GB GB1230494D patent/GB1230494A/en not_active Expired

Patent Citations (1)

Non-Patent Citations (1)

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