US3917817A - Hair treating cosmetic compositions containing piperazine based cationic polymer - Google Patents

Hair treating cosmetic compositions containing piperazine based cationic polymer Download PDF

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US3917817A
US3917817A US310088A US31008872A US3917817A US 3917817 A US3917817 A US 3917817A US 310088 A US310088 A US 310088A US 31008872 A US31008872 A US 31008872A US 3917817 A US3917817 A US 3917817A
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hair
piperazine
cationic polymer
water
composition
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Guy Vanlerberghe
Henri Sebag
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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
    • A61Q5/02—Preparations for cleaning 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
    • A61K8/88—Polyamides
    • 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
    • A61Q5/12—Preparations containing hair conditioners
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/02—Polyamines
    • C08G73/0273—Polyamines containing heterocyclic moieties in the main chain
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
    • C08G73/0633—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only two nitrogen atoms in the ring
    • 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
    • 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
    • Y10S424/04—Dandruff

Definitions

  • ABSTRACT Piperazine-based low molecular weight film-forming cationic polymer is employed in a cosmetic hairconditioner composition comprising a solution of the polymer in amounts of about 0.1-5 weight percent of the composition in a solvent such as water, acidified water, or aqueous alcohol solution.
  • the present invention relates to compositions fo r treatingand conditioning the hair. More particularly, the prese n t invention i'elates to cosmetic compositions for the hair, containing a low m'olecu lar weight, filmforming cationic polymer. l i A Many people's hair because of itsgerieral state orlits sensitivity due tov relatively frequent periodic treatments such asbleaching, dyeingor permanent waving, often is difficultto comb out and to arrange e specially in the case of abundanthair.
  • the present invention now makesit possible to substantially limit or avoid these, disadyantagesby applying to the hair as a conditioner therefor-a low molecular weight, film-forming cationic polymer that imparts to the .hair an appearance of vigorand radiance.
  • This polymer can be used alone-o'r as. the maincomponent in ahair-dressing lotion, cream, gel, hairsetting lotion hair-setting 'reinforcer, or alternatively, as an adjuvant in a composition for shampooing, setting, in permanent waving the hair, in a hair dyeing composition, in a cream for treating-dry or greasy hair, in an antidandruff lotion or in similarcompositi'ons forapplication to the hair.
  • the application of the hair conditioner cosmetic composition of this invention results in improving the facility and ease of combing out wet hair and imparts thereto brilliancy, softness and manageability of dry hair. Hair treated with the,composition of this invention feels lighten while at the "same 'time appears thickerand more alive.
  • the conditioner according to the 'inven'tion which acts as a softener and emollient, producesafter application of the same to the hair in. a shampoo, for example, a more brilliant, more voluminous and more aerated hair without the appearance of static electricity.
  • the cationic polymer of the present invention provides the additional advantage of avoiding a powdering phenomenon which is frequently observed with numerous conventionally employed polymers.
  • comositions also include other components or hair treating agents, does not entail any appreciable -re- 'duction of the properties or effectiveness of theseother components.
  • the cationic polymer of the present invention is i characterized by the fact that the cationic groups are part of the main polymer chain and that they are essentially derivedfrorn. bisecondary heterocyclic amines, preferably, piperazine. Structu rally', the 'low molecular weight, filmforming, cationic polymer of the present invention can be represented by the pattern 2 wherein A represents a radicalderived from a heterocycle containing two secondary amine functions and, preferably, the radical and. Z.
  • polymers of the present invention are those in which A has the meaning given above and B and B each independently represent a branched or straight chain radical selected from the group consisting of hydroxyalkyl 'ene having and, preferably, 3 carbon atoms, lower" alkyl-carbonamide lower alkyl-carbonamide-lower alkyl having 5 to 8 'and, preferably 6 m7 carbon atoms, hydroxypropyl-Oxyhydroxypropyl,"hydroxypropyl-alkylaminohydroxypropyl wherein the alkyl moiety has 12 to 16 carbon atoms, hydroxypropyl-alkenylamino-hydroxypropyl wherein the alk enyl moiety has 18 carbon atoms,hydroxypropylpiperazinylhydroxypropyl, propiOnyl-piperazinyl-propionyl and hydroxypropyl-benzylamino-hydroxypropyl.
  • the polymers of the present invention are more generally strictly alternated, -i.e. of the type wherein A and B have the meanings give n aboveQj
  • These rigorously'alternated polymers, which can be used in the present invention can be prepared byconventional processes such as by polyaddition or polycon- .densation of (a) piperazine or a derivative thereof such as, for example, N,Nbis(hydroxyethyl)piperazine,,on (b) abifunctional compound such as c I 1.; alkyl or'alkyl-aryl dihalides, such as ethylene chlo- -ride ethylene bromide or his chloromethyl, 1,4-benzene wherein the alkyl moiety has 1-4 carbon atoms, the aryl moiety is phenyl and the halide moiety is chloride or bromide;
  • bis halohydrins such as,bis 3-chloro 2-hydroxy propylether, or otherbis chlorohydrins which can be obtained by'conventional procedures such as by the condensation of epichlorohydrin. on (i) a primary amine, optionally hydroxylated, (ii) on a bisecondary diamine such as'piperazine, 4,4'- dipiperidyl, bis 4,4 (N-methylaminophenyl) methane, N,N 'dimethylethy- 'lene; diamine Orpropylene diamine, (iii) on.
  • a primary amine optionally hydroxylated
  • a bisecondary diamine such as'piperazine, 4,4'- dipiperidyl, bis 4,4 (N-methylaminophenyl) methane, N,N 'dimethylethy- 'lene; diamine Orpropylene diamine, (iii) on.
  • a,w-dimercaptoalkane (iv) on a diol such as ethylene glycol or (v) Ona bis phenol such as hydroquinone or his .phenOlA;' v 1' 4. bis epoxide such as diglycidyl ether or N,Nbis (epoxy-2,3 propyl)piperazine, eventually obtained from the corresponding bis halohydrin;
  • epihalohydrins such as epichlorohydrin or epibromohydrin
  • bisecondary bis unsaturated derivatives such as divinyl sulfone, bis maleimide derived from ethylene diamine, or bis acrylamide such as methylene bis acrylamide or piperazine bis acrylamide derived from 'biprimary or bissecondary diamines;
  • unsaturated acids such as acrylic or methacrylic acid or their methyl or ethyl esters
  • diacids such as succinic, adipic, 2,2,4-trimethyl or 2,4,4-trimethyl adipic or terephthalic acids, acid chlorides or the corresponding methyl or ethyl esters; and 9. diisocyanates, such as toluene diisocyanate or 2,2,4- or 2,4,4-trimethyl hexamethylene isocyanate.
  • the polyaddition or polycondensation reaction can be carried out at ambient pressure and at a temperature ranging fromabout to 100C, the molar ratio of (a) to (b), defined above being 0.85 l to 1.15 1.
  • the polymers of the present invention can in certain cases advantageously be prepared in essentially the same way by polycondensation or polyaddition of (a N,Nbis(3-chloro 2-hydroxy propyl) piperazine or N,N'bis (2,3-epoxy propyl) piperazine on (b') a bifunctional compound such as a bisecondary diamine, a dimercaptan, a diol, a diphenol, a diacid, and
  • a primary amine such as an alkylamine, alkenylamine,
  • aralkylamine of which the two hydrogen atoms can be substituted and which behaves as a bifunctional compound,'the molar ratio of (a') to(b') ranging from 0.85
  • the cationic polymers of the present inventi'oncan also, in certain cases, be of the pattern iLe. be made up of polymer chains in which A, representing a bisecondary heterocyclic amine group, for example, the piperazine group, is distributed regularly, the two B and B groups designated by Z in formula (I) beingdistributed statistically.
  • A representing a bisecondary heterocyclic amine group, for example, the piperazine group
  • Z Z in formula (I) beingdistributed statistically.
  • This type of polymer is 1 obtained'when piperazine or one of its derivatives is condensed with a mixture of two bifunctional derivatives.
  • polycondensates of type I, II or [II can then, in
  • the oxidation reaction of the polycondensate of type i I, [1 or [II can be performed with the amount of oxidizing agent being present in amounts from 0 to 100 percent relative to the oxidizable groups, while the quaternization reaction of the polycondensate of type I, II or .111 can be performed with the amount of quaternization 7 agent being present in amounts of 0 to 50 percent.
  • the cationic polymers of the present invention are also characterized by the fact that they are all filmforming and are generally of relatively low molecular weight, i.e. less than 15,000 and generally about LOCO-15,000. They are water soluble in acid medium and a number of them are also soluble as such in water without addition of acid or in dilute alcohol medium such as ethanol or isopropanol.
  • the alcohol i.e. lower alkanol, can be present in amounts of about 0 to 50 percent by weight of said composition.
  • the acid employed can be hydrochloric, acetic, lactic, or tartaric acid in amounts sufficient to solubilize the said poly mer.
  • the acid will be present in amounts of about 0 to 5 percent by weight of the composition.
  • These polymers are particularly effective for hair which has become sensitives as a result of such treatments as bleaching, permanent waving, or dyeing. They can, however, also advantageously be used for normal hair.
  • an object of the present invention is the provision of a cosmetic composition for conditioning the hair comprising a solution in a solvent selected from the group consisting of water and an aqueous solution of a lower alkanol, of a member selected from the group consisting of (l) a low molecular weight, film-forming cationic polymer of the formula in which A represents a radical derived from a heterocycle carrying two secondary amine functions and preferably the radical and Z represents the symbol B or B; B and B each independently representing a bivalent radical selected from the group consisting of (i) hydroxypropylene, (ii) alkylene having up to 5 carbon atoms inclusive and interrupted by l-2member selected from the group consisting of CONH and CON.
  • NCO a bivalent radical selected from the group consisting of (i) hydroxypropylene, (ii) alkylene having up to 5 carbon atoms inclusive and interrupted by l-2member selected from the group consisting of CONH and CON.
  • alkylene moiety has up to 6 carbon atoms inclusive and interrupted by a member selected from the group consisting of alkylamine wherein the alkyl moiety has 12-16 carbon atoms, benzylamine, oleylamine and oxygen, or (2) quaternary ammonium salt of the cationic polymer in (l) or (3) the oxidation product of the cationic polymer in (1).
  • a and B and B each independently represent a branched or straight chain radical selected from the group consisting of hydroxyackylene having l-6 carbon atoms, preferably 3 carbon atoms, lower alkyl-carbonamidelower alkyl-carbonamide-lower alkyl having 5-8 and preferably 6-7 carbon atoms, hydroxypropyl-oxyhydroxypropyl, hydroxypropyl-alkylamino-hydroxypropyl wherein the alkyl moiety has 12-16 carbon atoms, hydroxypropyl-alkenylamino-hydroxypropyl wherein the alkenyl moiety has 18 carbon atoms, hydroxypropyl-piperizinyl-hydroxypropyl, propionylpiperizinylpropionyl and hydroxypropyl-benzylamino-hydroxypropyl.
  • the polymer can be present in amounts of about 0.1 to 5 percent and preferably 0.2 to 3 percent by weight in the various cosmetic compositions of the present invention.
  • These compositions include hair-dressing lotions, creams or gels as the main constituent, shampoos, hair-setting compositions, permanent wave composition or hair dye compositions, etc.
  • the polymers can also be employed as an adjuvant in the presence of other components such as anionic, cationic, non-ionic, amphoteric or zwitterionic surfactants, oxidizing agents, foam stabilizers or synergists, sequestrants, superfatting agents, thickeners, softeners, antiseptics, preservatives, dyes, perfumes, germicides or other anionic, cationic, amphoteric or non-ionic polymers.
  • other components such as anionic, cationic, non-ionic, amphoteric or zwitterionic surfactants, oxidizing agents, foam stabilizers or synergists, sequestrants, superfatting agents, thickeners, softeners, antiseptics, preservatives, dyes, perfumes, germicides or other anionic, cationic, amphoteric or non-ionic polymers.
  • the polymers can be used in different compositions whose pI-l varies from 3 to 11, or in the form of inorganic or organic acid salts, or in the form of free base or, alternatively, the quaternary ammonium salt thereof.
  • the cosmetic compositions for hair according to the present invention can be in the form of an aqueous solution, a dilute alcohol solution, a cream, a paste, a gel, or a powder. They can also contain a conventional aerosol propellant such as dichlorodifluoromethane, monochlorotrifluoromethane, mixtures thereof or other conventional aerosol propellants, and can be packaged in a conventional aerosol bomb under pressure.
  • a conventional aerosol propellant such as dichlorodifluoromethane, monochlorotrifluoromethane, mixtures thereof or other conventional aerosol propellants
  • the hair shampoo compositions according to the invention are characterized by the fact that they contain, in addition to an anionic, cationic, non-ionic, amphoteric and/or switterionic surfactant, one or more compounds of formula I and optionally foam stabilizers or synergists, sequestrants, superfatting agents, thickeners, one or more other cosmetic resins, softeners, dyes, perfumes, antiseptics, preservatives and any other adjuvant usually used in cosmetic compositions.
  • an anionic, cationic, non-ionic, amphoteric and/or switterionic surfactant one or more compounds of formula I and optionally foam stabilizers or synergists, sequestrants, superfatting agents, thickeners, one or more other cosmetic resins, softeners, dyes, perfumes, antiseptics, preservatives and any other adjuvant usually used in cosmetic compositions.
  • the polymers of formula I also make it possible to prepare hair-setting lotions, hair-setting reinforcers,
  • treatment creams, hair conditioners, anti-dandruff lotions and other similar compositions characterized by the fact that they contain one or more polymers of formula I having a molecular weight, determined by lowering of the vapor tension, between 1,000 and 15,000, or the quaternary ammonium salt or amine oxide of these polymers, possibly mixed with other cosmetic resins.
  • a limpid and almost colorless solution is thus obtained, having a viscosity of 2.5 poises, measured at 25C.
  • a polymer similar to that of Example 1, but free of sodium chloride, is prepared by olycondensation of piperazine and N,N' bis(2,3-epoxy propyl) piperazine in an aqueous medium and in stoichiometric proportions.
  • the N,Nbis-(2,3-epoxy propyl) piperazine can be prepared in the following way:
  • the resulting dichlorohydrin derived from piperazine, is filtered and dried. It is a white crystallized product having a melting point of l08l 10C.
  • Example 4 mole) of 200 volume hydrogen peroxide The tempera- 1O ture is maintained at this level for hours.
  • the polymer solution obtained is perfectly limpid and yields, on evaporation, films comparable to those of Example 1.
  • the compound thus obtained is soluble in water in an acid medium and in a dilute alcohol medium. It yields beautiful, hard and very brilliant films, after evaporation of its dilute alcohol solvent.
  • Example 7 Quaternization of the product obtained in Example To 68 g of the above isopropanol solution (0.23 equivalent in base nitrogen) there are added, drop by drop at 30C, 14.6 (0.11 mole) of dimethyl sulfate. Stirring is continued for 2 hours. The solvent is then eliminated under partial vacuum, with water being added to produce a final aqueous solution that is 10 percent by weight.
  • the film obtained by evaporation of the dilute solution is rather hard and not sticky.
  • the molecular weight of this resin measured in absolute ethanol, is 2900.
  • Example 1 Polycondensation of N,N-bis(2,3-epoxy propyl) piperazine, oleyamine and piperazine.
  • Films obtained by evaporation of the dilute solution are transparent, not sticky and slightly hard.
  • Films obtained by evaporation of the dilute solution are opalescent, hard and not sticky.
  • the diglycidyl ether is prepared by reacting at 1520C a stoichiometric amount of sodium hydroxide on bis(3-chloro 2-hydroxy propyl) ether.
  • the diglycidyl ether is isolated by distillation under reduced pres- 9 sure. The boiling point is 8085C/0.05 mm Hg,
  • methylene bisacrylamide provided in paste form with-23.1 g of water there are added with agitation at a temperature between 0 and 5C under a nitrogen atmosphere, 152.5 g of a standardized aqueous solution containing 22.8 g (0.1 mole) of 1,3-bis piperazine-2-propanol. The mixture is left standing for 30 hours at C.
  • the polymer is precipitated in accordance with the procedure outlined in Example 14.
  • the l,3-bis-piperazine-2-propanol, utilized above, can be prepared as follows:
  • reaction mixture is stirred again for a period of 1 hour at a temperature of 20C. Then there are added at this temperature over a 1 hour period, 30 g (0.3 mole) of a 40 percent NaOH solution.
  • reaction mixture After an additional 1 hour period of stirring the reaction mixture at 20C, the reaction mixture is heated for 1 hour at C. There is thus obtained a 20 percent solution of the polymer exhibiting a very light opalescence and being nearly'colorless. By evaporating the dilute aqueous solution there is obtained a very hard, transparent and non-sticky film.
  • Example 20 Anionic shampoo R(OCH,CH,),OSO;Na wherein R alkyl C -C in proportions of 70/30 10 g Diethanolamide of copra fatty acids 3 g Water, q.s.p. I00 g pH 7
  • Example 21 Anionic shampoo Compound prepared according to Example 1 0.75 g Triethanolamine alkyl sulfate wherein alkyl C /C 70/30 15 g Monoethanolamide of copra fatty acid 4 g Sodium N-lauryl sarcosinate 3 g Acetylated lanolin 3 g Water, q.slp. 100 g pH 7.5
  • Example 22 Non-ionic shampoo Compound prepared according to Example I 2.5 g
  • R- OCH,iH OH wherein R alkyl C I-[, 15 g H OH Alkoxylated anhydrous lanolin sold under the trademark Lantrol AWS" by Malstrom Chemical Corporation, New Jersey 1.5 Hydroxypropyl methyl cellulose 0.3
  • Example 17 Setting lotion for very dry hair Compound prepared according to Example I
  • Example 23 Cationic shampoo Compound prepared according to Example 8 Bromide of dodecyl, tetradecyl and hexadecyl trimethylammonium sold under the tradename Cetavlon" Lauryl alcohol oxyethylenated with 12 moles of ethylene oxide Lauryl diethanolamide Ethyl cellulose Lactic acid, q.s.p. pH 4 Water, q.s.p.
  • Example 24 Amphoteric shampoo Compound prepared according to Example I CH sold under the name Miranol "CZM" by Miranol Chemical Corporation, lrvington. New Jersey Dimethyl alkylamine oxide prepared from copra fatty acids Lauryl diethanolamide Lauryl alcohol, oxyethylenated with 12 moles of ethylene oxide Lactic acid, q.s.p. pH 6 Water, q.s.p.
  • Example 25 Amphoteric shampoo Compound prepared according to Example l Sodium salt of N,N(diethylamino propyl)N'- dodecyl asparagin R OCH,il-l OH wherein R alkyl, C I-l H OH 4 Lactic acid, q.s.p.
  • Example 26 Anionic shampoo Compound prepared according to Example 9 Sodium alkyl sulfate (alkyl C C Sodium N-lauryl sarcosinate Lauryl monoethanolamide Glycol distearate Water, q.s.p. pH 7
  • Example 27 Anionic shampoo Compound prepared according to Example 9 RO(CHCH2)2OSO3N3 wherein R C ll Sodium salt of N,N(diethylamino propyl)-N- dodecyl asparagin Diethylanolamide of copra fatty acids Hydroxypropyl cellulose Water, q.s.p. pH 6.5
  • Example 28 Cream for treating dry hair Compound prepared according to Example 1, q.s.p. Cetyl alcohol Stearyl alcohol Cetyl-stearyl alcohol oxyethylenated with 15 moles of ethylene oxide Hydroxyethylcellulose Perfume Water, q.s.p.
  • Example 29 Conditioner for dry hair Compound prepared according to Example I, q.s.p. Polyvinylpyrrolidone/vinyl acetate copolymer 70/30 (M.W. 40,000) Perfume Water, q.s.p.
  • This conditioner is to be used after shampooing and before setting, without intermediate rinsing.
  • Example 17 Setting lotion for very dry hair Anionic shampoo in the form of a clear solution
  • Ammonium alkylsulfate (alkyl derived from copra)
  • Sodium alkyl ether sulfate'iavherein the alkyl moiety is derived from copra fatty acids and oxyethylenated with 2 moles of ethylene oxide i
  • Example 32 Anionic shampoo Sodium alkyl ether sulfate wherein the alkyl moiety is derived from copra fatty acids and oxyethylenated with 2 moles of ethylene oxide Copra diethanolamide Compound prepared according to Example 13 Sodium monolauryl sulfosuccinate Lactic acid, q.s.p. pH 7.5
  • Example 33 Anionic shampoo The composition of Example 32 is repeated except that the compound prepared according to Example 13 is replaced with an essentially equivalent amount of the compound prepared according to Example 14. Essentially similar effective and advantageous results are achieved with this composition.
  • This solution imparts to hair a lively and shiny appearance.
  • Example 17-22, 24, and 28-30 the compound prepared in accordance with Example 1 is replaced with the compound prepared in accordance with Example 15 and 16 in essentially equivalent amounts to provide equally effective hair treating compositions.
  • the weight of the polymer is expressed as the active material therein.
  • Cosmetic composition for conditioning the hair comprising a solution in a solvent selected from the group consisting of water and water-lower alkanol, of a member selected from the group consisting of l. a film-forming cationic polymer having a molecular weight of about 1,000 to 15,000 and having the formula wherein A represents and Z represents B andIB' wherein B and B each independently represent a bivalent radical selected from the group consisting of (i) hydroxypropylene, (ii) alkylene having up to 5 carbon atoms inclusive and interrupted by l-2 members selected from the group consisting of -CONH and (iii) hydroxy alkylene wherein the alkylene moiety has up to 6 carbon atoms inclusive and interrupted by a member selected from the group consisting of alkylamine wherein the alkyl moiety has 12-16 carbon atoms, benzylamine, oleylamine and oxygen, and (iv) hydroxy propyl-piperazinyl-hydroxypropyl,
  • composition according to claim 1 characterized by the fact that it is in the form of a cream.
  • A represents and Z represents B and B wherein B and B each independently represent a bivalent radical selected from the group consisting of (i) hydroxypropylene, (ii) alkylene having up to carbon atoms inclusive and interrupted by 1-2 members selected from the group consisting of -CONH and -CON NCO- (iii) hydroxy alkylene wherein the alkylene moiety has up to 6 carbon atoms inclusive and interrupted by a member selected from the group consisting of alkylamine wherein the alkyl moiety has 12-16 carbon atoms, benzylamine, oleylamine and oxygen and (iv) hydroxy propyl-piperazinyl-hydroxypropyl,
  • composition of claim 4 which also includes an anionic, cationic, non-ionic or amphoteric surfactant.
  • composition according toclaim 4 having a pH between 3 and 11.
  • composition according to claim 4 wherein said cationic polymer has a molecular weight less than 15,000.

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US310088A 1971-11-29 1972-11-28 Hair treating cosmetic compositions containing piperazine based cationic polymer Expired - Lifetime US3917817A (en)

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US (1) US3917817A (ja)
JP (1) JPS6025410B2 (ja)
AR (1) AR213060A1 (ja)
AT (1) AT331990B (ja)
BE (1) BE792004A (ja)
BR (1) BR7208360D0 (ja)
CA (1) CA1026039A (ja)
CH (1) CH559038A5 (ja)
DE (1) DE2258222C3 (ja)
DK (1) DK134141B (ja)
ES (2) ES409075A1 (ja)
FR (1) FR2162025B1 (ja)
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GB1416454A (en) 1975-12-03
FR2162025B1 (ja) 1976-01-30
ES409075A1 (es) 1976-03-01
JPS6025410B2 (ja) 1985-06-18
DE2258222C3 (de) 1982-09-23
DK134141C (ja) 1977-02-21
CH559038A5 (ja) 1975-02-28
DK134141B (da) 1976-09-20
DE2258222B2 (de) 1982-02-04
JPS4875732A (ja) 1973-10-12
DE2258222A1 (de) 1973-06-14
NL176223C (nl) 1985-03-18
BR7208360D0 (pt) 1973-08-30
IT1050457B (it) 1981-03-10
ES437446A1 (es) 1977-05-01
ATA1010472A (de) 1975-12-15
BE792004A (en) 1973-05-28
CA1026039A (en) 1978-02-07
AU4934972A (en) 1974-05-30
AR213060A1 (es) 1978-12-15
NL7216145A (ja) 1973-06-01
LU64371A1 (ja) 1973-06-21
FR2162025A1 (ja) 1973-07-13
AT331990B (de) 1976-09-10
NL176223B (nl) 1984-10-16

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