WO1998004233A1 - Compositions de shampooing traitant avec polyalkylene amine polyalkoxylee - Google Patents

Compositions de shampooing traitant avec polyalkylene amine polyalkoxylee Download PDF

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WO1998004233A1
WO1998004233A1 PCT/US1996/012518 US9612518W WO9804233A1 WO 1998004233 A1 WO1998004233 A1 WO 1998004233A1 US 9612518 W US9612518 W US 9612518W WO 9804233 A1 WO9804233 A1 WO 9804233A1
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alkyl
silicone
conditioning
carbon atoms
hair
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PCT/US1996/012518
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English (en)
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Jeffrey Scheibel
Hirotaka Uchiyama
Junichi Yokogi
Mikiko Nakata
Takashi Sako
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The Procter & Gamble Company
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Priority to PCT/US1996/012518 priority Critical patent/WO1998004233A1/fr
Priority to GB9715395A priority patent/GB2315770A/en
Publication of WO1998004233A1 publication Critical patent/WO1998004233A1/fr

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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
    • A61Q5/12—Preparations containing hair conditioners
    • 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
    • A61K8/416—Quaternary ammonium compounds
    • 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
    • A61K8/45—Derivatives containing from 2 to 10 oxyalkylene groups
    • 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
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • A61K8/65—Collagen; Gelatin; Keratin; Derivatives or degradation products thereof
    • 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
    • A61K8/73—Polysaccharides
    • A61K8/731—Cellulose; Quaternized cellulose derivatives
    • 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
    • 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
    • A61K8/86—Polyethers
    • 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
    • A61K8/89—Polysiloxanes
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • 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
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0084—Antioxidants; Free-radical scavengers

Definitions

  • the present invention relates to conditioning shampoo compositions comprising polyalkoxylated polyalkyleneamine.
  • shampooing cleans the hair by removing excess soil and sebum.
  • shampooing can leave the hair in a wet, tangled, and generally unmanageable state. Once the hair dries, it is often left in a dry, rough, lusterless, or frizzy condition due to removal of the hair's natural oils and other natural conditioning and moisturizing components. The hair can further be left with increased levels of static upon drying, which can interfere with combing and result in a condition commonly referred to as "flyaway hair.”
  • silicone conditioning agents Materials which can provide improved overall conditioning benefits while maintaining cleaning performance with the use of anionic detersive surfactants are silicone conditioning agents.
  • conditioning shampoos comprising silicone conditioning agents have a tendency of leaving the hair feeling coated, heavy, or soiled after the hair is dried.
  • a silicone suspending agent such as acyl derivatives or long chain amine oxide is required.
  • the combination of silicone conditioning agents and its suspending agents often provide a formulation which is relatively viscous and milky in appearance.
  • shampoos of less viscosity or transparent appearance are also desired. It would be desirable to provide a conditioning shampoo composition that would provide improved overall conditioning benefits with or without silicone conditioning agents.
  • GB Patent specification 1,524,966 discloses a clear, homogeneous shampoo composition which comprises a polyethylene imine polymer as cationic conditioner, amine base detergent, and zinc 2- pyridinethiol- 1 -oxide.
  • conditioning agents polyalkoxylated polyalkyleneamines
  • polyalkoxylated polyalkyleneamines have been developed which are water soluble and compatible with a wide variety of components commonly formulated in conditioning shampoos, particularly with detersive surfactants which provide good cleaning properties.
  • the polyalkoxylated polyalkyleneamines of the present invention provide improved overall conditioning benefits with or without silicone conditioning agents.
  • conditioning benefits such as; wet and dry hair conditioning benefits recognized by the consumer as soft and smooth feel of the hair and easy dry combing; and absence of coated, heavy, or soiled hair feel, are improved.
  • the present invention relates to conditioning shampoo compositions comprising a polyalkoxylated polyalkyleneamine, a detersive surfactant, and water.
  • the present invention further relates to a conditioning shampoo composition comprising by weight, from about 0.01% to about 10% of polyalkoxylated polyalkyleneamine, from about 0.01% to about 20% of a cationic surfactant conditioning agent, from about 5% to about 50% of a detersive surfactant, and from about 20% to about 90% of water.
  • compositions satisfy the need for a conditioning shampoo composition with improved overall conditioning benefits with or without silicone conditioning agents, and/or a conditioning shampoo composition with good cleaning properties.
  • the invention hereof can comprise, consist of, or consist essentially of the essential elements described herein as well as any of the preferred or optional ingredients also described herein.
  • polyalkoxylated polyalkyleneamine of the present invention can be described by the following formula:
  • A is a polyalkoxy of the formula (R-*0) H wherein R-* is a C2 to C4 alkylene and y is an integer from 1 to about 40; and x is an integer from 0 to
  • A is preferably a polyethoxy or polypropoxy, most preferably a polyethoxy, and y is preferably from about 5 to about 30, most preferably from about 10 to about 20.
  • R 1 and R 2 are preferably independently C2 to C4, most preferably both are C2; and x is preferably from 1 to about 10, most preferably from 1 to about 5.
  • These polyalkoxylated polyalkyleneamines are water soluble and compatible with any detersive surfactant including anionic detersive surfactants, and also provide excellent conditioning benefits to the hair. Without being bound by theory, at most wash pH's, it is believed that the nitrogen atoms of these compounds are partially protonated.
  • the resulting positively charged centers are believed to aid in the adsorption of the compound onto the negatively charged layers of the hair. Such adsorption is believed to provide conditioning benefits similar to that obtained by cationic conditioning agents. It is also believed that, when the hydrophilic alkoxy units of the compound meet an abundant amount of water in the rinsing process, it loses its cohesive character so that excess polyalkoxylated polyalkyleneamine is removed from the hair, thus not leaving the hair feel coated, heavy, or soiled.
  • the pH of the present compositions generally will be about 2 to about 9, preferably about 5 to about 7.
  • Exemplary polyalkoxylated polyalkyleneamines are ethoxylated and propoxylated; ethylenediamine, propylenediamine, n-butylenediamine, pentamethylenediamine, hexamethylenediamine, diethylenetriamine, triethylenetetramine, and tetraethylenepentamine.
  • a highly preferred compound is polyethoxylated tetraethylenepentamine as shown below wherein y is an integer of from about 10 to about
  • polyalkoxylated polyalkyleneamines can be synthesized by standard methods for alkoxylating amines.
  • This initial step can be omitted by starting with a 2-hydroxyalkylamine such as triethanolamine or polyalkyleneamine.
  • the appropriate amount of alkylene oxide is then condensed with these 2-hydroxyalkyleneamines or polyalkyleneamines using an alkali metal such as sodium or potassium; hydride or hydroxide as the catalyst to provide the respective alkoxylated amines.
  • the polyalkoxylated polyalkyleneamine of the present invention is incorporated in conditioning shampoo compositions at a level of from about 0.01% to about 10%, preferably from about 0.1% to about
  • compositions of the present invention comprise a detersive surfactant selected from the group consisting of one or more anionic, nonionic, amphotenc, or zwitterionic surfactants, or mixtures thereof.
  • the purpose of the detersive surfactant is to provide cleansing performance to the composition.
  • detersive surfactant is intended to distinguish these surfactants from surfactants which are primarily emulsifying surfactants, i.e. surfactants which provide an emulsifying benefit and which have low cleansing performance. It is recognized that most surfactants have both detersive and emulsifying properties. It is not intended to exclude emulsifying surfactants from the present invention, provided the surfactant also possesses sufficient detersive properties to be useful herein.
  • the detersive surfactants will generally comprise from about 5% to about 50%, preferably from about 8% to about 30%, and more preferably from about 10% to about 25%, by weight of the composition.
  • Anionic Surfactants Anionic surfactants useful herein include alkyl and alkyl ether sulfates.
  • ROSO3M and RO(C2H4 ⁇ ) x S ⁇ 3M wherein R is alkyl or alkenyl of from about 8 to about 30 carbon atoms, x is 1 to about 10, and M is hydrogen or a cation such as ammonium, al anolammonium (e.g., triethanolammoniu ), a monovalent metal cation (e.g., sodium and potassium), or a polyvalent metal cation (e.g., magnesium and calcium).
  • M should be chosen such that the anionic surfactant component is water soluble.
  • the anionic surfactant should be chosen such that the Krafft temperature is about 15°C or less, preferably about 10°C or less, and more preferably about 0°C or less. It is also preferred that the anionic surfactant be soluble in the composition hereof.
  • Krafft temperature refers to the point at which solubility of an ionic surfactant becomes determined by crystal lattice energy and heat of hydration, and corresponds to a point at which solubility undergoes a sharp, discontinuous increase with increasing temperature.
  • Each type of surfactant will have its own characteristic Krafft temperature.
  • Krafft temperature for ionic surfactants is, in general, well known and understood in the art. See, for example. Myers. Drew. Surfactant Science and Technoloev. DP. 82-85, VCH Publishers, Inc. (New York, New York, USA), 1988 (ISBN 0-89573-399-0), which is incorporated by reference herein in its entirety.
  • R has from about 12 to about 18 carbon atoms in both the alkyl and alkyl ether sulfates.
  • the alkyl ether sulfates are typically made as condensation products of ethylene oxide and monohydric alcohols having from about 8 to about 24 carbon atoms.
  • the alcohols can be derived from fats, e.g., coconut oil, palm oil, tallow, or the like, or the alcohols can be synthetic. Lauryl alcohol and straight chain alcohols derived from coconut oil and palm oil are preferred herein.
  • Such alcohols are reacted with 1 to about 10, and especially about 3, molar proportions of ethylene oxide and the resulting mixture of molecular species having, for example, an average of 3 moles of ethylene oxide per mole of alcohol, is sulfated and neutralized.
  • alkyl ether sulfates which can be used in the present invention are sodium and ammonium salts of coconut alkyl triethylene glycol ether sulfate; tallow alkyl triethylene glycol ether sulfate, and tallow alkyl hexaoxyethylene sulfate.
  • Highly preferred alkyl ether sulfates are those comprising a mixture of individual compounds, said mixture having an average alkyl chain length of from about 12 to about 16 carbon atoms and an average degree of ethoxylation of from 1 to about 4 moles of ethylene oxide.
  • Such a mixture also comprises from 0% to about 20% by weight C 12.13 compounds; from about 60% to about 100% by weight compounds, from 0% to about 20% by weight of .17- 18- 19 compounds; from about 3% to about 30% by weight of compounds having a degree of ethoxylation of 0; from about 45% to about 90% by weight of compounds having a degree of ethoxylation of from 1 to about 4; from about 10% to about 25% by weight of compounds having a degree of ethoxylation of from about 4 to about 8; and from about 0.1% to about 15% by weight of compounds having a degree of ethoxylation greater than about 8.
  • Suitable anionic surfactants are the water-soluble salts of organic, sulfuric acid reaction products of the general formula [Ri-SC- ⁇ -M] where K is selected from the group consisting of a straight or branched chain, saturated aliphatic hydrocarbon radical having from about 8 to about 24, preferably about 10 to about 18, carbon atoms; and M is as previously described above in this section.
  • surfactants are the salts of an organic sulfuric acid reaction product of a hydrocarbon of the methane series, including iso-, neo-, and n-paraff ⁇ ns, having about 8 to about 24 carbon atoms, preferably about 12 to about 18 carbon atoms and a sulfonating agent, e.g., SO3, H2SO4, obtained according to known sul- fonation methods, including bleaching and hydrolysis.
  • a sulfonating agent e.g., SO3, H2SO4
  • alkali metal and ammonium sulfonated CIQ-IS n-paraffins are preferred.
  • anionic surfactants are the reaction products of fatty acids esterified with isethionic acid and neutralized with sodium hydroxide where, for example, the fatty acids are derived from coconut or palm oil; or sodium or potassium salts of fatty acid amides of methyl tauride in which the fatty acids, for example, are derived from coconut oil.
  • Other similar anionic surfactants are described in U.S. Patents 2,486,921, 2,486,922, and 2,396,278, which are incorporated by reference herein in their entirety.
  • anionic surfactants suitable herein are the succinates, examples of which include disodium N-octadecylsulfosuccinate; disodium lauryl sulfosuccinate; diammonium lauryl sulfosuccinate; tetra sodium N-(l,2-dicarboxyethyl)-N-octadecyl- sulfosuccinate; the diamyl ester of sodium sulfosuccinic acid; the dihexyl ester of sodium sulfosuccinic acid; and the dioctyl ester of sodium sulfosuccinic acid.
  • anionic surfactants suitable herein are those that are derived from amino acids.
  • Nonlimiting examples of such surfactants include N-acyl-L-glutamate, N-acyl-N-methyl-alanate, N- acylsarcosinate, and their salts.
  • Still other useful surfactants are those that are derived from taurine, which is also known as 2- aminoethanesulfonic acid.
  • An example of such an acid is N-acyl-N-methyl taurate.
  • Suitable anionic surfactants include olefin sulfonates having about 10 to about 24 carbon atoms.
  • olefin sulfonates 1 ' is used herein to mean compounds which can be produced by the sulfonation of alpha-olef ⁇ ns by means of uncomplexed sulfur trioxide, followed by neutralization of the acid reaction mixture in conditions such that any suifones which have been formed in the reaction are hydroiyzed to give the corresponding hydroxy-alkanesulfonates.
  • the sulfur trioxide can be liquid or gaseous, and is usually, but not necessarily, diluted by inert diluents, for example by liquid S0 2 , chlorinated hydrocarbons, etc., when used in the liquid form, or by air, nitrogen, gaseous SO2, etc., when used in the gaseous form.
  • the alpha-olefins from which the olefin sulfonates are derived are mono-olefins having about 12 to about 24 carbon atoms, preferably about 14 to about 16 carbon atoms. Preferably, they are straight chain olefins.
  • the olefin sulfonates can contain minor amounts of other materials, such as alkene disulfonates depending upon the reaction conditions, proportion of reactants, the nature of the starting olefins and impurities in the olefin stock and side reactions during the sulfonation process.
  • alkene disulfonates depending upon the reaction conditions, proportion of reactants, the nature of the starting olefins and impurities in the olefin stock and side reactions during the sulfonation process.
  • a specific alpha -olefin sulfonate mixture of the above type is described more fully in U.S. Patent 3,332,880, to Pflaumer and Kessler, issued July 25, 1967, which is incorporated by reference herein in its entirety.
  • Another class of anionic surfactants suitable for use in the present invention are the betaalkyloxy alkane sulfonates. These compounds have the following formula:
  • R* is a straight chain alkyl group having from about 6 to about 20 carbon atoms
  • R 2 is a lower alkyl group having from about 1, preferred, to about 3 carbon atoms
  • M is as hereinbefore described.
  • anionic surfactants suitable for use are described in McCutcheon's. Emulsifiers and Detergents. 1989 Annual, published by M. C. Publishing Co., and in U.S. Patent 3,929,678, which descriptions are incorporated herein by reference in their entirety.
  • Preferred anionic surfactants for use include ammonium lauryl sulfate, ammonium laureth sulfate, triethylamine lauryl sulfate, triethylamine laureth sulfate, triethanolamine lauryl sulfate, triethanolamine laureth sulfate, monoethanolamine lauryl sulfate, monoethanolamine laureth sulfate, diethanolamine lauryl sulfate, diethanolamine laureth sulfate, lauric monoglyceride sodium sulfate, sodium lauryl sulfate, sodium laureth sulfate, potassium lauryl sulfate, potassium laureth sulfate, sodium lauryl sarcosinate, sodium lauroyl sarcosinate, lauryl sarcosine, cocoyl sarcosine, ammonium cocoyl sulfate, ammonium lauroyl
  • the shampoo compositions can comprise amphoteric and/or zwitterionic surfactants.
  • Amphoteric surfactants for use in the shampoo compositions include the derivatives of aliphatic secondary and tertiary amines in which the aliphatic radical is straight or branched and one of the O 98/04233
  • aliphatic substituents contains from about 8 to about 18 carbon atoms and one contains an anionic water solubilizing group, e.g., carboxy, sulfonate, sulfate, phosphate, or phosphonate.
  • Zwitterionic surfactants for use in the shampoo compositions include the derivatives of aliphatic quaternary ammonium, phosphonium, and sulfonium compounds, in which the aliphatic radicals are straight or branched, and wherein one of the aliphatic substituents contains from about 8 to about 18 carbon atoms and one contains an anionic group, e.g., carboxy, sulfonate, sulfate, phosphate, or phosphonate.
  • a general formula for these compounds is:
  • R contains an alkyl, alkenyl, or hydroxy alkyl radical of from about 8 to about 18 carbon atoms, from 0 to about 10 ethylene oxide moieties and from 0 to about 1 glyceryl moiety;
  • Y is selected from the group consisting of nitrogen, phosphorus, and sulfur atoms;
  • R is an alkyl or monohydroxyalkyl group containing 1 to about 3 carbon atoms;
  • X is 1 when Y is a sulfur atom, and 2 when Y is a nitrogen or 4 phosphorus atom;
  • R is an alkylene or hydroxyalkylene of from 1 to about 4 carbon atoms and Z is a radical selected from the group consisting of carboxylate, sulfonate, sulfate, phosphonate, and phosphate groups.
  • amphoteric and zwitterionic surfactants also include sultaines and amidosultaines.
  • Suitaines including amidosultaines, include for example, cocodimethylpropylsultaine, stearyldimethylpropylsultaine, lauryl-bis-(2-hydroxyethyl) propylsultaine and the like; and the amidosultaines such as cocamidodimethyipropylsultaine, stearylamidododimethylpropylsultaine, laurylamidobis-(2-hydroxyethyl) propylsultaine, and the like.
  • amidohydroxysultaines such as the C12-C18 hydrocarbyl amidopropyl hydroxy sultaines, especially C12-C14 hydrocarbyl amido propyl hydroxysultaines, e.g., laurylamidopropyl hydroxysultaine and cocamidopropyl hydroxysultaine.
  • C12-C18 hydrocarbyl amidopropyl hydroxy sultaines especially C12-C14 hydrocarbyl amido propyl hydroxysultaines, e.g., laurylamidopropyl hydroxysultaine and cocamidopropyl hydroxysultaine.
  • Other sultaines are described in U.S. Patent 3,950,417, which is incorporated herein by reference in its entirety.
  • amphoteric surfactants are the aminoalkanoates of the formula R-NH(CH 2 ) n COOM, the iminodialkanoates of the formula R-N[(CH2) rn COOMl 2 and mixtures thereof; wherein n and m are numbers from 1 to about 4, R is Cg - C22 alkyl or alkenyl, and M is hydrogen, alkali metal, alkaline earth metal, ammonium or alkanolammonium.
  • Suitable aminoalkanoates include n-alkylamino-propionates and n-alkyliminodipropionates, specific examples of which include N-lauryl-beta-amino propionic acid or salts thereof, and N-lauryl-beta-imino-dipropionic acid or salts thereof, and mixtures thereof.
  • amphoteric surfactants include those represented by the formula :
  • R 1 is Cg - C22 alkyl or alkenyl, preferably C ⁇ -Cj ⁇ .
  • R ⁇ and R 3 is independently selected from the group consisting of hydrogen, CH 2 C0 2 M, CH 2 CH 2 OH, CH2CH2OCH2CH2COOM, or (CH2CH2 ⁇ ) m H wherein m is an integer from 1 to about 25, and R 4 is hydrogen, Q-2CH2OH, or CH2CH2OCH2CH2COOM, Z is C0 2 M or CH 2 C0 2 M, n is 2 or 3, preferably 2, M is hydrogen or a cation, such as alkali metal (e.g., lithium, sodium, potassium), alkaline earth metal (beryllium, magnesium, calcium, strontium, barium), or ammonium.
  • alkali metal e.g., lithium, sodium, potassium
  • alkaline earth metal beryllium, magnesium, calcium, strontium, barium
  • This type of surfactant is sometimes classified as an imidazoline-type amphoteric surfactant, although it should be recognized that it does not necessarily have to be derived, directly or indirectly, through an imidazoline intermediate.
  • Suitable materials of this type are marketed under the tradename MTRANOL and are understood to comprise a complex mixture of species, and can exist in protonated and non-protonated species depending upon pH with respect to species that can have a hydrogen at R 2 . All such variations and species are meant to be encompassed by the above formula.
  • surfactants of the above formula are monocarboxylates and dicarboxylates.
  • examples of these materials include cocoamphocarboxypropionate, cocoamphocarboxypropionic acid, cocoa phocarboxyglycinate (alternately referred to as cocoamphodiacetate), and cocoamphoacetate.
  • MIRANOL C2M CONC. N.P. MIRANOL C2M CONC. O P.
  • MIRANOL C2M SF MIRANOL CM SPECIAL
  • ALKATERIC 2CIB Alkaril Chemicals
  • AMPHOTERGE W-2 Liranol, Inc.
  • MONATERIC CDX-38 MONATERIC CSH-32 (Mona Industries)
  • REWOTERIC AM-2C Rewo Chemical Group
  • SCHERCOTERIC MS-2 Scher Chemicals.
  • Betaine surfactants i.e. zwitterionic surfactants, suitable for use in the shampoo compositions are those represented by the formula:
  • R* is a member selected from the group consisting of
  • R 2 is lower alkyl or hydroxyalkyl;
  • R ⁇ is lower alkyl or hydroxyalkyl;
  • R 4 is a member selected from the group consisting of hydrogen and lower alkyl;
  • R ⁇ is higher alkyl or alkenyl;
  • Y is lower alkyl, preferably methyl;
  • m is an integer from 2 to 7, preferably from 2 to 3;
  • n is the integer 1 or 0;
  • M is hydrogen or a cation, as previously described, such as an alkali metal, alkaline earth metal, or ammonium.
  • lower alkyl or "hydroxyalkyl” means straight or branch chained, saturated, aliphatic hydrocarbon radicals and substituted hydrocarbon radicals having from one to about three carbon atoms such as, for example, methyl, ethyl, propyl, isopropyl, hydroxypropyl, hydroxyethyl, and the like.
  • higher alkyl or alkenyl means straight or branch chained saturated (i.e., “higher alkyl") and unsaturated (i.e., “higher alkenyl”) aliphatic hydrocarbon radicals having from about eight to about 20 carbon atoms such as, for example, lauryl, cetyl, stearyl, oleyl, and the like. It should be understood that the term “higher alkyl or alkenyl” includes mixtures of radicals which may contain one or more intermediate linkages such as ether or polyether linkages or non-functional substitutents such as hydroxyl or halogen radicals wherein the radical remains of hydrophobic character.
  • surfactant betaines of the above formula wherein n is zero which are useful herein include the alkylbetaines such as cocodimethylcarboxymethylbetaine, lauryldimethylcarboxymethyl- betaine, lauryl dimethyl-alpha- arboxyethylbetaine, cetyldimethylcarboxymethylbetaine, lauryl-bis-(2-hydroxyethyl)carboxymethylbetaine, stearyl-bis-(2-hydroxypropyl)carboxymethylbetaine, oleyldimethyl-gamma-carboxypropylbetaine, lauryl-bix-(2-hydroxypropyl)a!pha-carboxyethylbetaine, etc.
  • alkylbetaines such as cocodimethylcarboxymethylbetaine, lauryldimethylcarboxymethyl- betaine, lauryl dimethyl-alpha- arboxyethylbetaine, cetyldimethylcarboxymethylbetaine, lauryl-bis-
  • the sulfobetaines may be represented by cocodimethylsulfopropylbetaine, stearyldimethylsulfo- propylbetaine, lauryl-bis-(2-hydroxyethyl)sulfopropylbetaine, and the like.
  • amido betaines and amidosulfo betaines useful in the shampoo compositions include the amidocarboxybetaines, such as cocamidodimethylcarboxymethylbetaine, laurylamidodi- methylcarboxymethylbetaine, cetylamidodimethylcarboxymethylbetaine, laurylamido-bis-(2-hydroxyethyl)-carboxymethylbetaine, cocamido-bis-(2-hydroxyethyl)-carboxymethylbetaine, etc.
  • amidocarboxybetaines such as cocamidodimethylcarboxymethylbetaine, laurylamidodi- methylcarboxymethylbetaine, cetylamidodimethylcarboxymethylbetaine, laurylamido-bis-(2-hydroxyethyl)-carboxymethylbetaine, cocamido-bis-(2-hydroxyethyl)-carboxymethylbetaine, etc.
  • amido sulfobetaines may be represented by cocamidodimethylsulfopropylbetaine, stearylamidodimethylsulfopropylbetaine, lauryl- amido-bis-(2-hydroxyethyl)-sulfopropylbetaine, and the like.
  • the shampoo compostions of the present invention can comprise a nonionic surfactant.
  • Nonionic surfactants include those compounds produced by condensation of alkylene oxide groups, hydrophilic in nature, with an organic hydrophobic compound, which may be aliphatic or alkyl aromatic in nature.
  • Preferred nonlimiting examples of nonionic surfactants for use in the shampoo compositions include the following:
  • polyethylene oxide condensates of alkyl phenols e.g., the condensation products of alkyl phenols having an alkyl group containing from about 6 to about 20 carbon atoms in either a straight chain or branched chain configuration, with ethylene oxide, the said ethylene oxide being present in amounts equal to from about 10 to about 60 moles of ethylene oxide per mole of alkyl phenol;
  • R contains an alkyl, alkenyl or monohydroxyalkyl radical ranging from about 8 to about 18 carbon atoms in chain length, from 0 to about 10 ethylene oxide moieties and from 0 to 1 glyceryl moieties and R' and R" are each alkyl or monohydroxyalkyl groups containing from about 1 to about 3 carbon atoms;
  • R long chain dialkyl sulfoxides containing one short chain alkyl or hydroxy alkyl radical of from 1 to about 3 carbon atoms (usually methyl) and one long hydrophobic chain which include alkyl, alkenyl, hydroxy alkyl, or keto alkyl radicals containing from about 8 to about 20 carbon atoms, from 0 to about 10 ethylene oxide moieties and from 0 to 1 glyceryl moieties;
  • alkyl polysaccharide (APS) surfactants e.g. alkyl polyglycosides
  • alkyl polysaccharide (APS) surfactants e.g. alkyl polyglycosides
  • APS surfactants having a hydrophobic group with about 6 to about 30 carbon atoms and a polysaccharide (e.g., polyglycoside) as the hydrophilic group; optionally, there can be a polyalkylene-oxide group joining the hydrophobic and hydrophilic moieties; and the alkyl group (i.e., the hydrophobic moiety) can be saturated or unsaturated, branched or unbranched, and unsubstituted or substituted (e.g., with hydroxy or cyclic rings); a preferred material is alkyl polyglucoside which is commercially available from Henkel, ICI Americas, and Seppic; and
  • polyoxyethylene alkyl ethers such as those of the formula RO(CI--2CH2) n H and polyethylene glycol (PEG) glyceryl fatty esters, such as those of the formula R(0)OCH 2 CH(OH)CH2(OCH 2 CH2) n OH, wherein n is from 1 to about 200, preferably from about 20 to about 100, and R is an alkyl having from about 8 to about 22 carbon atoms.
  • PEG polyethylene glycol
  • compositions of the present invention preferably further comprise from about 0.1% to about 20% by weight, preferably from about 0.25% to about 5%, more preferably from about 0.5% to about 2% of a cationic surfactant conditioning agent.
  • cationic surfactant conditioning agents typically contain quaternary nitrogen moieties.
  • the cationic surfactant will preferably, though not necessarily, be insoluble in the compositions hereof.
  • cationic surfactants useful herein are those corresponding to the general formula (I): Rl
  • R*, R- R 3 , and R 4 are independently selected from an aliphatic group of from 1 to about 22 carbon atoms or an aromatic, alkoxy, polyoxyalkylene, alkylamido, hydroxyalkyl, aryl or alkylaryl group having up to about 22 carbon atoms, and X is a salt-forming anion such as those selected from halogen, (e g chloride, bromide), acetate, citrate, lactate, glycolate, phosphate, nitrate, sulfonate, sulfate, alkylsulfate, and alkyl sulfonate radicals
  • the aliphatic groups can contain, in addition to carbon and hydrogen atoms, ether linkages, and other groups such as amino groups
  • the longer chain aliphatic groups, e g , those of about 12 carbons, or higher, can be saturated or unsaturated Preferred is when R 1 , R 2
  • hydrophihcally substituted catio c surfactants in which at least one of the substituents contain one or more aromatic, ether, ester, amido, or ammo moieties present as substituents or as linkages in the radical chain, wherein at least one of the R 1 - R 4 radicals contain one or more hydrophilic moieUes selected from alkoxy (preferably C j - C3 alkoxy), polyoxyalkylene (preferably Ci - C3 polyoxyalkylene), alkylamido, hydroxyalkyl, alkylester, and combinauons thereof
  • the hydrophilically substituted cationic conditioning surfactant contains from 2 to about 10 nonionic hydrophile moieues located within the above stated ranges
  • Preferred hydrophihcally substituted catiomc surfactants include those of the formula (II) through (VII) below zi (ii) I
  • R7 R!O wherein m is 1 to 5, one or more of R ⁇ , R 6 , and R 7 are independently an C ⁇ - C30 alkyl, the remainder are CH 2 CH 2 OH, one or two of R 8 , R 9 , and R t0 are independently an C j - C30 alkyl, and remainder are CH 2 CH 2 OH, and X is a salt forming anion as mentioned above, o z 2 o
  • Z 2 is an alkyl, preferably a C j - C3 alkyl, more preferably methyl, and Z 3 is a short chain hydroxyalkyl, preferably hydroxymethyl or hydroxyethyl, p and q independently are integers from 2 to 4, inclusive, preferably from 2 to 3, inclusive, more preferably 2, R 1 1 and R 2 , independently, are substituted or unsubstituted hydrocarbyls, preferably C j2 - C 2Q alkyl or alkenyl, and X is a salt forming anion as defined above;
  • R ⁇ 3 is a hydrocarbyl, preferably a CI - C3 alkyl, more preferably methyl
  • Z 4 and Z ⁇ are, independently, short chain hydrocarbyls, preferably C2 - C4 alkyl or alkenyl, more preferably ethyl, a is from 2 to about 40, preferably from about 7 to about 30, and
  • X is a salt forming anion as defined above;
  • R 15 OH wherein R 14 and R ⁇ , independently, are C ⁇ . j alkyl, preferably methyl, Z 6 is a C ⁇ 2 to C 22 hydrocarbyl, alkyl carboxy or alkylamido, and A is a protein, preferably a collagen, keratin, milk protein, silk, soy protein, wheat protein, or hydroiyzed forms thereof; and X is a salt forming anion as defined above;
  • Nonlimiting examples of hydrophilically substituted cationic surfactants useful in the present invention include the materials having the following CTFA designations: quatemium-16, quatemium-61, quaternium-71, quatemium-79 hydroiyzed collagen, quaternium-79 hydroiyzed keratin, quatemium-79 hydroiyzed milk protein, quatemium-79 hydroiyzed silk, quaternium- 79 hydroiyzed soy protein, and quatemium-79 hydroiyzed wheat protein.
  • Highly preferred compounds include commercially available materials; VARIQUAT K1215 and 638 from Witco Chemical, MACKPRO KLP, MACKPRO WLW, MACKPRO MLP, MACKPRO NSP, MACKPRO NLW, MACKPRO WWP, MACKPRO NLP, MACKPRO SLP from Mclntyre, ETHOQUAD 18/25, ETHOQUAD 0/12PG, ETHOQUAD C/25, ETHOQUAD S/25 and ETHODUOQUAD from Akzo, DEHYQUAT SP from Henkel, and ATLAS G265 from IC1 Americas
  • Salts of primary, secondary and tertiary fatty amines are also suitable cationic surfactant conditioning agent
  • the alkyl groups of such amines preferably have from about 12 to about 22 carbon atoms, and can be substituted or unsubstituted
  • Such amines, useful herein, include steararrudo propyl dimethyl amine, diethyl amino ethyl stearamide, dimethyl stearamine, dimethyl soyamine, soyamine, mynstyl amine, tndecyl amine, ethyl stearylamine, N-tallowpropane diamine, ethoxylated (with 5 moles of ethylene oxide) stearylamine, dihydroxy ethyl stearylamine, and arachidylbehenylamine
  • Suitable amine salts include the halogen, acetate, phosphate, nitrate, citrate, lactate, and alkyl sulfate salts
  • the catiomc surfactant conditioning agents for use herein may also include a plurality of ammonium quaternary moieties or ammo moieties, or a mixture thereof OTHER CONDITIONING AGENTS
  • conditioning agents include water soluble catiomc polymers, fatty compounds, nonvolatile dispersed sihcones, hydrocarbons, proteins, and mixtures thereof These conditioning agents are compnsed at a level of from about 001% to about 20% of the conditioning shampoo composition of the present invenUon
  • Water Soluble Cationic Polymers are useful herein by “water soluble” is meant a polymer which is sufficiently soluble in water to form a substantially clear solution to the naked eye at a concentration of 0 1% in water, i e. distilled or equivalent, at 25°C Preferably, the polymer will be sufficiently soluble to form a substantially clear solution at a 0 5% concentration, more preferably at a 1 0% concentration
  • the water soluble cationic polymers hereof will generally have a weight average molecular weight which is at least about 5,000, typically at least about 10,000, and is less than about 10 million Preferably, the molecular weight is from about 100,000 to about 2 million
  • the cationic polymers will generally have catiomc nitrogen-containing moieties such as quaternary ammonium or cationic amino moieties, and mixtures thereof
  • the catiomc charge density is preferably at least about 0 1 meq/gram, more preferably at least about 0.2 meq/gram, and preferably less than about 3 0 meq/gram, more preferably less than about 2 75 meq/gram
  • the cationic charge density of the cationic polymer can be determined according to the Kjeldahl Method, which is well-known to those skilled in the art. Those skilled in the art will recognize that the charge density of amino-containing polymers can vary depending upon pH and the isoelectric point of the amino groups. The charge density should be within the above limits at the pH of intended use.
  • Any anionic counterions can be utilized for the water soluble cationic polymers so long as the water solubility criteria is met. Suitable counterions include halides (e.g., CI, Br, I, or F, preferably CI, Br, or I), sulfate, and methylsulfate. Others can also be used, as this list is not exclusive.
  • the cationic nitrogen-containing moiety will be present generally as a substituent, on a fraction of the total monomer units of the cationic hair conditioning polymers.
  • the water soluble cationic polymer can comprise copolymers, te ⁇ olymers, etc. of quaternar ammonium or cationic amine-substituted monomer units and other non-cationic units referred to herein as spacer monomer units.
  • Such polymers are known in the art, and a variety can be found in International Cosmetic Ingredient Dicitonary, Fifth Edition, 1993, which is incorporated by reference herein in its entirety.
  • Suitable water soluble cationic polymers include, for example, copolymers of vinyl monomers having cationic amine or quaternary ammonium functionalities with water soluble spacer monomers such as acrylamide, methacrylamide, alkyl and dialkyl acryiamides, alkyl and dialkyl methacrylamides, alkyl acrylate, alkyl methacrylate, vinyl caprolactone, and vinyl pyrrolidone.
  • the alkyl and dialkyl substituted monomers preferably have C1-C7 alkyl groups, more preferably C1-C3 alkyl groups.
  • Other suitable spacer monomers include vinyl esters, vinyl alcohol (made by hydrolysis of polyvinyl acetate), maleic anhydride, propylene glycol, and ethylene glycol.
  • the cationic amines can be primary, secondary, or tertiary amines, depending upon the particular species and the pH of the composition. In general, secondary and tertiary amines, especially tertiary amines, are preferred.
  • Amine-substituted vinyl monomers can be polymerized in the amine form, and then optionally can be converted to ammonium by a quatemization reaction.
  • Amines can also be similarly quaternized subsequent to formation of the polymer.
  • tertiary amine functionalities can be quaternized by reaction with a salt of the formula 'X wherein R' is a short chain alkyl, preferably a C1-C alkyl, more preferably a C 1 -C3 alkyl, and X is an anion which forms a water soluble salt with the quaternized ammonium.
  • Suitable cationic amino and quaternary ammonium monomers include, for example, vinyl compounds substituted with dialkylaminoalkyl acrylate, dialkylaminoalkyl methacrylate, monoalkyl- aminoalkyl acrylate, monoalkylaminoalkyl methacrylate, trialkyl methacryloxyalkyl ammonium salts, trialkyl acryloxyalkyl ammonium salts, diallyl quaternary ammonium salts, and vinyl quaternary ammonium monomers having cyclic cationic nitrogen-containing rings such as pyridinium, imidazolium, and quaternized pyrrolidone, e.g., alkyl vinyl imidazolium, alkyl vinyl pyridinium, alkyl vinyl pyrrolidone salts.
  • the alkyl portions of these monomers are preferably lower alkyls such as the C1-C3 alkyls, more preferably CI and C2 alkyls
  • Suitable amine-substituted vinyl monomers for use herein include dialkylaminoalkyl acrylate, dialkylaminoalkyl methacrylate, dialkylaminoalkyl acrylamide, and dialkylaminoalkyl methacrylamide, wherein the alkyl groups are preferably C j -C ⁇ alkyl and more preferably C1-C3, alkyl
  • the water soluble catiomc polymers hereof can comprise mixtures of monomer units de ⁇ ved from amine- and/or quaternary ammonium-substituted monomer and/or compatible spacer monomers
  • Suitable water soluble catiomc polymers include, for example copolymers of l-v ⁇ nyl-2 -pyrrolidone and l-v ⁇ nyl-3-methyl ⁇ m ⁇ dazol ⁇ um salt (e g , chlonde salt), referred to in the industry by the CTFA designation as polyquatern ⁇ um-16, which is commercially available from BASF Co ⁇ oration under the LUVIQUAT tradena e (e g , LUVIQUAT FC 370), copolymers of l-vmyl-2- -pyrrolidone and dimethylaminoethyl methacrylate, referred to as polyquatern ⁇ um-11, which is commercially available from Gaf Co ⁇ oration (Wayne, NJ, USA) under the GAFQUAT tradename (e g , GAFQUAT 755N), ca ⁇ omc diallyl quaternary ammonium-containing polymers, including, for example, dimethyldiallylammonium chlon
  • water soluble catiomc polymers that can be used include polysaccharide polymers, such as catiomc cellulose derivatives and cationic starch denvatives
  • Catiomc polysacchande polymer matenals suitable for use herein include those of the formula *
  • A is an anhydroglucose residual group, such as a starch or cellulose anhydroglucose residual
  • R is an alkylene oxyalkylene, polyoxyalkylene, or hydroxyalkylene group, or combination thereof
  • R j , R2, and R3 independently are alkyl, aryl, alkylaryl, arylaikyl, alkoxyalkyl, or alkoxyaryl groups, each group contaimng up to about 18 carbon atoms, and the total number of carbon atoms for each catio c moiety (1 e , the sum of carbon atoms in R j , R2 and R3) preferably being about 20 or less
  • X is an aiuoiuc counte ⁇ on, e g., halide, sulfate, nitrate, and the like
  • Cationic cellulose is available from Amerchol Co ⁇ (Edison, NJ, USA) in their Polymer JR®,
  • LR® and SR® se ⁇ es of polymers, as salts of hydroxyethyl cellulose reacted with t ⁇ methyl ammonium subsUtuted epoxide, refened to by the CTFA designation polyquatern ⁇ um-10
  • Another type of catiomc cellulose includes the polyme ⁇ c quaternary ammonium salts of hydroxyethyl cellulose reacted with lauryl 17
  • dimethyl ammonium-substituted epoxide referred to by the CTFA as polyquatemium-24, and which is available from Amerchol Corp. (Edison, NJ, USA) under the tradename Polymer LM-200®.
  • water soluble cationic polymers that can be used include cationic guar gum derivatives, such as guar hydroxypropyltrimonium chloride (commercially available from Celanese Corp. in their Jaguar R series).
  • cationic guar gum derivatives such as guar hydroxypropyltrimonium chloride (commercially available from Celanese Corp. in their Jaguar R series).
  • Other materials include quaternary nitrogen-containing cellulose ethers (e.g., as described in U.S. Patent 3,962,418, which is incorporated by reference herein in its entirety), and copolymers of etherified cellulose and starch (e.g., as described in U.S. Patent 3,958,581, which is incorporated herein by reference in its entirety).
  • water soluble cationic polymers selected from the group consisting of polyquaternium-7, polyquaternium-10, polyquaternium-11, and mixtures thereof.
  • Fatty compounds including fatty alcohols, fatty acids, fatty alcohol derivatives, fatty acid derivatives, and mixtures thereof are preferred conditioning agents. It is recognized that the compounds disclosed in this section of the specification can in some instances fall into more than one classification, e.g., some fatty alcohol derivatives can also be classified as fatty acid derivatives. Also, it is recognized that some of these compounds can have properties as nonionic surfactants and can alternatively be classified as such. However, a given classification is not intendend to be a limitation on that particular compound, but is done so for convenience of classification and nomenclature.
  • Nonlimiting examples of the fatty alcohols, fatty acids, fatty alcohol derivatives, and fatty acid derivatives are found in International Cosmetic Ingredient Dictionary, Fifth Edition, 1993, and CTFA Cosmetic Ingredient Handbook, Second Edition, 1992, both of which are incorporated by reference herein in their entirety.
  • the fatty alcohols useful herein are those having from about 10 to about 30 carbon atoms, preferably from about 12 to about 22 carbon atoms, and more preferably from about 16 to about 22 carbon atoms. These fatty alcohols can be straight or branched chain alcohols and can be saturated or unsaturated.
  • Nonlimiting examples of fatty alcohols include decyl alcohol, undecyl alcohol, dodecyl, myristyl, cetyl alcohol, stearyl alcohol, isostearyl alcohol, isocetyl alcohol, behenyl alcohol, Iinalool, oleyl alcohol, cholesterol, c/ ' .s--4-f-butylcyclohexanol, myricy alcohol and mixtures thereof.
  • Especially preferred fatty alcohols are those selected from the group consisting of cetyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, and mixtures thereof.
  • the fatty acids useful herein are those having from about 10 to about 30 carbon atoms, preferably from about 12 to about 22 carbon atoms, and more preferably from about 16 to about 22 carbon atoms. These fatty acids can be straight or branched chain acids and can be saturated or unsaturated. Also included are diacids, triacids, and other multiple acids which meet the carbon number requirement herein. Also included herein are salts of these fatty acids.
  • Nonlimiting examples of fatty acids include lauric acid, palmitic acid, stearic acid, behenic acid, arichidonic acid, oleic acid, isosteanc acid, sebacic acid, and mixtures thereof.
  • fatty acids selected from the group consisting of palmitic acid, stearic acid, and mixtures thereof.
  • the fatty alcohol derivatives are defined herein to include alkyl ethers of fatty alcohols, alkoxylated fatty alcohols, alkyl ethers of alkoxylated fatty alcohols, esters of fatty alcohols and mixtures thereof.
  • Nonlimiting examples of fatty alcohol derivatives include materials such as methyl stearyl ether; 2-ethylhexyl dodecyl ether; stearyl acetate; cetyl propionate; the ceteth series of compounds such as ceteth-1 through ceteth-45, which are ethylene glycol ethers of cetyl alcohol, wherein the numeric designation indicates the number of ethylene glycol moieties present; the steareth series of compounds such as steareth- 1 through 100, which are ethylene glycol ethers of steareth alcohol, wherein the numeric designation indicates the number of ethylene glycol moieties present; ceteareth 1 through ceteareth-50, which are the ethylene glycol ethers of ceteareth
  • Preferred for use herein are steareth-2, steareth-4, ceteth-2, and mixtures thereof.
  • the fatty acid derivatives are defined herein to include fatty acid esters of the fatty alcohols as defined above in this section, fatty acid esters of the fatty alcohol derivatives as defined above in this section when such fatty alcohol derivatives have an esterifiable hydroxyl group, fatty acid esters of alcohols other than the fatty alcohols and the fatty alcohol derivatives described above in this section, hydroxy-substitued fatty acids, and mixtures thereof.
  • conditioning agents useful herein include nonvolatile, dispersed silicones.
  • nonvolatile is meant that the silicones exhibit very low or no significant vapor pressure at ambient conditions, e.g., 1 atmosphere at 25°C.
  • the nonvolatile dispersed silicone conditioning agent preferably has a boiling point at ambient pressure of about 250°C or higher, preferably of about 260°C, and more preferably of about 19
  • dispersed is meant that the silicones form a separate, discontinuous phase from the aqueous carrier such as in the form of an emulsion or a suspension of droplets.
  • the droplets have an average particle diameter from about 0.1 microns to about 25 microns, preferably from about 5 microns to about 20 microns.
  • the nonvolatile dispersed silicones for use herein will preferably have a viscosity of from about
  • Suitable silicone fluids include polyalkyl siloxanes, polyaryl siloxanes, polyalkylaryl siloxanes, polyether siloxane copolymers, and mixtures thereof. Other nonvolatile silicones having hair conditioning properties can also be used.
  • nonvolatile dispsersed silicones herein also include polyalkyl or polyaryl siloxanes with the following structure:
  • R R R R wherein R is alkyl or aryl, and x is an integer from about 7 to about 8,000.
  • "A" represents groups which block the ends of the silicone chains.
  • the alkyl or aryl groups substituted on the siloxane chain (R) or at the ends of the siloxane chains (A) can have any structure as long as the resulting silicone remains fluid at room temperature, is dispersible, is neither irritating, toxic nor otherwise harmful when applied to the hair, is compatible with the other components of the composition, is chemically stable under normal use and storage conditions, and is capable of being deposited on and conditions the hair.
  • Suitable A groups include hydroxy, methyl, methoxy, ethoxy, propoxy, and aryloxy.
  • the two R groups on the silicon atom may represent the same group or different groups. Preferably, the two R groups represent the same group.
  • Suitable R groups include methyl, ethyl, propyl, phenyl, methylphenyl and phenylmethyl.
  • the preferred silicones are polydimethyl siloxane, polydiethylsiloxane, and polymethylphenylsiloxane.
  • Poiydimethylsiloxane which is also known as dimethicone, is especially preferred.
  • the polyalkylsiloxanes that can be used include, for example, polydimethylsiloxanes. These silicones are available, for example, from the General Electric Company in their ViscasilR and SF 96 series, and from
  • Polyalkylaryl siloxane fluids can also be used and include, for example, polymethylphenylsiloxanes. These siloxanes are available, for example, from the General Electric Company as SF 1075 methyl phenyl fluid or from Dow Corning as 556 Cosmetic Grade Fluid.
  • highly arylated silicones such as highly phenylated polyethyl silicone having refractive indices of about 1.46 or higher, especially about 1.52 or higher.
  • a spreading agent such as a surfactant or a silicone resin, as described below to decrease the surface tension and enhance the film forming ability of the material.
  • the nonvolatile dispersed silicones that can be used include, for example, a polypropylene oxide modified poiydimethylsiloxane although ethylene oxide or mixtures of ethylene oxide and propylene oxide can also be used.
  • the ethylene oxide and polypropylene oxide level should be sufficiently low so as not to interfere with the dispersibility characteristics of the silicone. These material are also known as dimethicone copolyols.
  • nonvolatile dispersed silicones include amino substituted materials.
  • Suitable alkylamino substituted silicones include those represented by the following structure (II)
  • Suitable cationic silicone fluids include those represented by the formula (III) (R 1 ) a G3.
  • G is chosen from the group consisting of hydrogen, phenyl, OH, C j -Cg alkyl and preferably methyl; a denotes 0 or an integer from 1 to 3, and preferably equals 0; b denotes 0 or 1 and preferably equals 1; the sum n+m is a number from 1 to 2,000 and preferably from 50 to 150, n being able to denote a number from 0 to 1,999 and preferably from 49 to 149 and m being able to denote an integer from 1 to 2,000 and preferably from 1 to 10; R j is a monovalent radical of formula CqH 2 qL in which q is an integer from 2 to 8 and L is chosen from the groups
  • R 2 is chosen from the group consisting of hydrogen, phenyl, benzyl, a saturated hydrocarbon radical, preferably an alkyl radical containing from 1 to 20 carbon atoms, and A denotes a halide ion.
  • n and m are selected depending on the exact molecular weight of the compound desired.
  • silicone cationic polymers which can be used are represented by the formula (V): R4CH2— CHOH— CH 2 — N + (R3)3Q-
  • R 3 denotes a monovalent hydrocarbon radical having from 1 to 18 carbon atoms, preferably an alkyl or alkenyl radical such as methyl;
  • R4 denotes a hydrocarbon radical, preferably a C Cig alkylene radical or a C j -C j g. and more preferably C j -Cg, alkyleneoxy radical;
  • Q is a alide ion, preferably chloride;
  • r denotes an average statistical value from 2 to 20, preferably from 2 to 8;
  • s denotes an average statistical value from 20 to 200, and preferably from 20 to 50.
  • a preferred polymer of this class is available from Union Carbide under the name "UCAR SILICONE ALE 56.”
  • references disclosing suitable nonvolatile dispersed silicones include U.S. Patent No. 2,826,551, to Geen; U.S. Patent No. 3,964,500, to Drakoff, issued June 22, 1976; U.S. Patent No. 4,364,837, to Pader, and British Patent No. 849,433, to Woolston, all of which are incorporated herein by reference in their entirety. Also incorporated herein by reference in its entirety is "Silicon Compounds" distributed by Petrarch Systems, Inc., 1984. This reference provides an extensive, though not exclusive, listing of suitable silicones.
  • silicone gum means a polyorganosiloxane material having a viscosity at 25°C of greater than or equal to 1,000,000 centistokes. It is recognized that the silicone gums described herein can also have some overlap with the above-disclosed silicones. This overlap is not intended as a limitation on any of these materials. Silicone gums are described by Petrarch, Id., and others including U.S. Patent No. 4,152,416, to Spitzer et al., issued May 1, 1979 and Noll, Walter, Chemistry and Technology of Silicones, New York; Academic Press 1968.
  • silicone gums will typically have a mass molecular weight in excess of about 200,000, generally between about 200,000 and about 1,000,000. Specific examples include poiydimethylsiloxane, (poiydimethylsiloxane) (methylvinylsiloxane) copolymer, poiydimethylsiloxane) (diphenyl siloxane)(methylvinylsiloxane) copolymer and mixtures thereof.
  • silicone resins which are highly crosslinked polymeric siloxane systems.
  • the crosslinking is introduced through the incorporation of trifunctional and tetrafunctional silanes with monofunctional or difunctional, or both, silanes during manufacture of the silicone resin.
  • the degree of crosslinking that is required in order to result in a silicone resin will vary according to the specific silane units incorporated into the silicone resin.
  • silicone materials which have a sufficient level of trifunctional and tetrafunctional siloxane monomer units, and hence, a sufficient level of crosslinking, such that they dry down to a rigid, or hard, film are considered to be silicone resins.
  • the ratio of oxygen atoms to silicon atoms is indicative of the level of crosslinking in a particular silicone material.
  • Silicone materials which have at least about 1.1 oxygen atoms per silicon atom will generally be silicone resins herein.
  • the ratio of oxygen:silicon atoms is at least about 1.2:1.0.
  • Silanes used in the manufacture of silicone resins include monomethyl-, dimethyl-, trimethyl-, monophenyl-, diphenyl-, methylphenyl-, monovinyl-, and methylvinyl-chlorosilanes, and tetra- chlorosilane, with the methyl-substituted silanes being most commonly utilized.
  • silicone resins are offered by General Electric as GE SS4230 and SS4267.
  • Commercially available silicone resins will generally be supplied in a dissolved form in a low viscosity volatile or nonvolatile silicone fluid.
  • the silicone resins for use herein should be supplied and incorporated into the present compositions in such dissolved form, as will be readily apparent to those skilled in the art. Without being bound by theory, it is believed that the silicone resins can enhance deposition of other silicones on the hair and can enhance the glossiness of hair with high refractive index volumes.
  • silicone resin powders such as the material given the CTFA designation polymethylsilsequioxane, which is commercially available as Tospearl ⁇ f rom Toshiba Silicones.
  • Silicone materials and silicone resins in particular can conveniently be identified according to a shorthand nomenclature system well known to those skilled in the art as the "MDTQ" nomenclature. Under this system, the silicone is described according to the presence of various siloxane monomer units which make up the silicone.
  • M denotes the monofunctional unit (Ct ⁇ SiO) 5
  • D denotes the difunctional unit (Cl ⁇ SiO
  • T denotes the trifunctional unit (Cl SiOi 5
  • Q denotes the quadri- or tetra-functional unit S-O2.
  • Primes of the unit symbols, e.g., M ⁇ D', T, and Q' denote substituents other than methyl, and must be specifically defined for each occurrence. Typical alternate substituents include groups such as vinyl, phenyl, amino, hydroxyl, etc.
  • the molar ratios of the various units either in terms of subscripts to the symbols indicating the total number of each type of unit in the silicone, or an average thereof, or as specifically indicated ratios in combination with molecular weight, complete the description of the silicone material under the MDTQ system.
  • Higher relative molar amounts of T, Q, T and or Q' to D, D ⁇ M and/or or M' in a silicone resin is indicative of higher levels of crosslinking.
  • the overall level of crosslinking can also be indicated by the oxygen to silicon ratio.
  • the silicone resins for use herein which are preferred are MQ, MT, MTQ, MQ and MDTQ resins.
  • the preferred silicone substituent is methyl.
  • MQ resins wherein the M:Q ratio is from about 0.5:1.0 to about 1.5:1.0 and the average molecular weight of the resin is from about 1000 to about 10,000.
  • Hydrocarbons
  • Hydrocarbons are useful herein as conditioning agents.
  • Useful hydrocarbons include straight chain, cyclic, and branched chain hydrocarbons which can be either saturated or unsaturated.
  • the hydrocarbons preferably will have from about 12 to about 40 carbon atoms, more preferably from about 12 to about 30 carbon atoms, and most preferably from about 12 to about 22 carbon atoms.
  • Also encompassed herein are polymeric hydrocarbons of alkenyl monomers, such as polymers of C2-C6 alkenyl monomers. These polymers can be straight or branched chain polymers.
  • the straight chain polymers will typically be relatively short in length, having a total number of carbon atoms as described above in this paragraph.
  • the branched chain polymers can have substantially higher chain lengths.
  • the number average molecular weight of such materials can vary widely, but will typically be up to about 500, preferably from about 200 to about 400, and more preferably from about 300 to about 350.
  • mineral oils are liquid mixtures of hydrocarbons that are obtained from petroleum. Specific examples of suitable hydrocarbon materials include paraffin oil, mineral oil, dodecane, isododecane, hexadecane, isohexadecane, eicosene, isoeicosene, tridecane, tetradecane, polybutene, polyisobutene, and mixtures thereof.
  • Isododecane, isohexadeance, and isoeicosene are commercially available as Permethyl 99 A, Permethyl 101 A, and Permethyl 1082, from Presperse, South Plainfield, NJ.
  • a copolymer of isobutene and normal butene is commercially available as Indopol H-100 from Amoco Chemicals.
  • hydrocarbon conditioning agents selected from the group consisting of mineral oil, isododecane, isohexadecane, polybutene, polyisobutene, and mixtures thereof.
  • compositions herein can contain a variety of other optional components suitable for rendering such compositions more cosmetically or aesthetically acceptable or to provide them with additional usage benefits.
  • optional components are well-known to those skilled in the art.
  • Optional components generally are used individually at levels from about 0.01% to about 5.0%, preferably from about 0.05% to about 3.0% by weight of the composition.
  • a preferred optional component of the present invention is a polyalkylene glycol.
  • the polyalkylene glycols are characterized by the general formula: H(OCH2CH) n — OH
  • R is selected from the group consisting of H, methyl, and mixtures thereof.
  • these materials are polymers of ethylene oxide, which are also known as polyethylene oxides, polyoxyethylenes, and polyethylene glycols.
  • R is methyl
  • these materials are polymers of propylene oxide, which are also known as polypropylene oxides, polyoxypropylenes, and polypropylene glycols.
  • R is methyl
  • various positional iso ers of the resulting polymers can exist.
  • n has an average value of from about 1500 to about 25,000, preferably from about 2500 to about 20,000, and more preferably from about 3500 to about 15,000.
  • Polyethylene glycol polymers useful herein are PEG-2M wherein R equals H and n has an average value of about 2,000 (PEG-2M is also known as Polyox WSR® N-10, which is available from Union Carbide and as PEG-2,000); PEG-5M wherein R equals H and n has an average value of about 5,000 (PEG-5M is also known as Polyox WSR® N- 5 and Polyox WSR® N-80, both available from Union Carbide and as PEG-5,000 and Polyethylene Glycol 300,000); PEG-7M wherein R equals H and n has an average value of about 7,000 (PEG-7M is also known as Polyox WSR® N-750 available from Union Carbide); PEG-9M wherein R equals H and n has an average value of about 9,000 (PEG 9-M is also
  • suspending agent which is highly preferred for suspending the silicone hair conditioning agent, when present in dispersed form, in the compositions of the present invention.
  • the suspending agent will generally comprise from about 0.1% to about 10%, and more typically from about 0.3% to about 5.0%, by weight, of the composition.
  • Preferred suspending agents include acyl derivatives, long chain amine oxides, and mixtures thereof. When used in the compositions, these preferred suspending agents are present in crystalline form. These suspending agents are described in U.S. Patent 4,741,855, which is incorporated herein by reference in its entirety. These preferred suspending agents include ethylene glycol esters of fatty acids preferably having from about 16 to about 22 carbon atoms.
  • ethylene glycol stearates both mono and distearate, but particularly the distearate containing less than about 7% of the mono stearate.
  • suitable suspending agents include alkanol amides of fatty acids, preferably having from about 16 to about 22 carbon atoms, more 25
  • long chain acyl derivatives include long chain esters of long chain fatty acids (e.g., stearyl stearate, cetyl palmitate, etc.); glyceiyl esters (e.g., glyceryl distearate) and long chain esters of long chain alkanol amides (e.g., stearamide diethanolamide distearate, stearamide monoethanolamide stearate).
  • Long chain acyl derivatives ethylene glycol esters of long chain carboxylic acids, long chain amine oxides, and alkanol amides of long chain carboxylic acids in addition to the preferred materials listed above may be used as suspending agents.
  • suspending agents with long chain hydrocarbyls having C -C22 chains may be used.
  • Other long chain acyl derivatives suitable for use as suspending agents include
  • N,N-dihydrocarbyl amido benzoic acid and soluble salts thereof e.g., Na and K salts
  • soluble salts thereof e.g., Na and K salts
  • N.N-di(hydrogenated) Ci6 particularly N.N-di(hydrogenated) Ci6, Cj and tallow amido benzoic acid species of this family, which are commercially available from Stepan Company (Northfield, Illinois, USA).
  • Suitable long chain amine oxides for use as suspending agents include alkyl (C16-C22) dimethyl amine oxides, e.g., stearyl dimethyl amine oxide.
  • suspending agents include xanthan gum.
  • xanthan gum as a suspending agent in silicone containing shampoo compositions is described, for example, in U.S. Patent 4,788,006, which is incorporated herein by reference in its entirety.
  • Combinations of long chain acyl derivatives and xanthan gum may also be used as a suspending agent in the shampoo compositions. Such combinations are described in U.S. Patent 4,704,272, which is incorporated herein by reference in its entirety.
  • suspending agents include carboxyvinyl polymers.
  • Preferred among these polymers are the copolymers of acrylic acid crosslinked with polyallylsucrose as described in U.S. Patent 2,798,053, which is incorporated herein by reference in its entirety.
  • Examples of these polymers include the carbomers, which are hompolymers of acrylic acid crosslinked with an allyl ether of pentaerythrotol, an allyl ether of sucrose, or an allyl ether of propylene.
  • Preferred carboxyvinyl polymers have a molecular weight of at least about 750,000; more preferred are carboxyvinyl polymers having a molecular weight of at least about 1,250,000; most preferred are carboxyvinyl polymers having a molecular weight of at least about 3,000,000.
  • suspending agents include those that can impart a gel-like viscosity to the composition, such as water soluble or coiloidally water soluble polymers like cellulose ethers such as hydroxyethyl cellulose, and materials such as guar gum, polyvinyl alcohol, polyvinyl pyrrolidone, hydroxypropyl guar gum, starch and starch derivatives, and other thickeners, viscosity modifiers, gelling agents, etc. Mixtures of these materials can also be used.
  • water soluble or coiloidally water soluble polymers like cellulose ethers such as hydroxyethyl cellulose
  • materials such as guar gum, polyvinyl alcohol, polyvinyl pyrrolidone, hydroxypropyl guar gum, starch and starch derivatives, and other thickeners, viscosity modifiers, gelling agents, etc. Mixtures of these materials can also be used.
  • additional optional components can be formulated into the present composition. These include: hair-hold polymers; additional thickening agents; viscosity modifiers such as methanolamides of long chain fatty acids such as cocomonoethanol amide; crystalline suspending agents; pearlescent aids such as ethylene glycol distearate; preservatives such as benzyl alcohol, benzoic acid, methyl paraben, propyl paraben and imidazolidinyl urea, iodopropynyl butyl carbamate, methylisothiazolinone, methychloroisothiazolinone, polyvinyl alcohol, ethyl alcohol; salts and electrolytes such as sodium chloride, potassium chloride, sodium sulfate, and ammonium xylene sulfonate; pH adjusting agents, such as citric acid, sodium citrate, succinic acid, phosphoric acid, sodium hydroxide, sodium carbonate; fragrances and colorings to modify the aesthetic
  • compositions herein can also contain a wide variety of additional components.
  • additional components are disclosed in International Cosmetic Ingredient Dictionary, Fifth Edition, 1993, and CTFA Cosmetic Ingredient Handbook, Second Edition, 1992, both of which are incorporated by reference herein in their entirety.
  • compositions of the present invention can be prepared by using conventional mixing and formulating techniques.
  • the conditioning shampoo compositions illustrated hereinafter are prepared in the following manner.
  • compositions of the present invention in general, can be made by mixing the materials together at elevated temperature, e.g., about 75°C.
  • the nonvolatile dispersed silicones such as Dimethicone is first mixed before being mixed with the other ingredients. T e complete mixture is then mixed thoroughly at the elevated temperature and is then pumped through a high shear mill and then through a heat exchanger to cool it to ambient temperature, until the desired silicone particle size is achieved.
  • the nonvolatile dispersed silicones can be mixed with anionic surfactant and fatty compounds such as cetyl and stearyl alcohols, at elevated temperature, to form a premix.
  • the premix can then be added to and mixed with the remaining materials of the composition, pumped through a high shear mill, and cooled.
  • the composition illustrated, all of which are embodiments of the present invention, are useful for both cleansing and conditioning the hair from a single product. All percentages are based on weight.

Abstract

Compositions de shampooing traitant contenant une polyalkylène amine polyalkoxylée et un ou plusieurs tensioactifs détergents; et, dans d'autres modes de réalisation, compositions de shampooing traitant contenant, en poids, entre 0,01 % et 10 % environ de polyalkylène amine alkoxylée, entre 0,01 % et 20 % environ d'un agent traitant tensioactif cationique, et entre 5 % et 50 % environ d'un tensioactif détergent et entre 20 % et 90 % environ d'eau.
PCT/US1996/012518 1996-07-31 1996-07-31 Compositions de shampooing traitant avec polyalkylene amine polyalkoxylee WO1998004233A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/US1996/012518 WO1998004233A1 (fr) 1996-07-31 1996-07-31 Compositions de shampooing traitant avec polyalkylene amine polyalkoxylee
GB9715395A GB2315770A (en) 1996-07-31 1997-07-23 Conditioning shampoo compositions comprising polyalkoxylated polyalkyleneamine

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US1996/012518 WO1998004233A1 (fr) 1996-07-31 1996-07-31 Compositions de shampooing traitant avec polyalkylene amine polyalkoxylee

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EP2939659A4 (fr) * 2012-12-26 2016-10-05 Kao Corp Lavage capillaire
EP2939658A4 (fr) * 2012-12-26 2016-11-02 Kao Corp Produit cosmétique de gel capillaire

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EP1802267A1 (fr) * 2004-10-13 2007-07-04 The Procter and Gamble Company Composition de revitalisant capillaire comprenant un tensio-actif cationique de sel d'ammonium alkyle diquaternise
BRPI0516600A (pt) * 2004-10-13 2008-09-16 Procter & Gamble composição para condicionamento dos cabelos compreendendo um tensoativo catiÈnico à base de sal de amÈnio alquil diquaternizado
US20180000705A1 (en) 2016-06-30 2018-01-04 The Procter & Gamble Company Shampoo Compositions Comprising a Chelant
US11786447B2 (en) 2016-06-30 2023-10-17 The Procter & Gamble Company Conditioner composition comprising a chelant
US11246816B2 (en) 2016-06-30 2022-02-15 The Procter And Gamble Company Shampoo compositions comprising a chelant
US20180000706A1 (en) 2016-06-30 2018-01-04 The Procter & Gamble Company Conditioner Composition Comprising a Chelant
US20180000715A1 (en) 2016-06-30 2018-01-04 The Procter & Gamble Company Hair Care Compositions For Calcium Chelation

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EP2939659A4 (fr) * 2012-12-26 2016-10-05 Kao Corp Lavage capillaire
EP2939658A4 (fr) * 2012-12-26 2016-11-02 Kao Corp Produit cosmétique de gel capillaire
US9566217B2 (en) 2012-12-26 2017-02-14 Kao Corporation Hair cleansing composition
US9849075B2 (en) 2012-12-26 2017-12-26 Kao Corporation Gel hair cosmetic

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GB9715395D0 (en) 1997-09-24

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