WO1999013849A1 - Compositions de soin pour les cheveux comprenant des agents optiques de brillance et des composes a point de fusion eleve - Google Patents

Compositions de soin pour les cheveux comprenant des agents optiques de brillance et des composes a point de fusion eleve Download PDF

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Publication number
WO1999013849A1
WO1999013849A1 PCT/US1997/016618 US9716618W WO9913849A1 WO 1999013849 A1 WO1999013849 A1 WO 1999013849A1 US 9716618 W US9716618 W US 9716618W WO 9913849 A1 WO9913849 A1 WO 9913849A1
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Prior art keywords
alkyl
carbon atoms
hair
compounds
silicone
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PCT/US1997/016618
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English (en)
Inventor
Xiaochun Luo
Arata Mitsumatsu
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The Procter & Gamble Company
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Publication date
Application filed by The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to PCT/US1997/016618 priority Critical patent/WO1999013849A1/fr
Priority to AU44864/97A priority patent/AU4486497A/en
Priority to JP2000511451A priority patent/JP2001516701A/ja
Priority to CN98811097A priority patent/CN1278717A/zh
Priority to BR9812818-3A priority patent/BR9812818A/pt
Priority to PCT/IB1998/001381 priority patent/WO1999013823A2/fr
Priority to EP98939798A priority patent/EP1028697A2/fr
Priority to AU88190/98A priority patent/AU8819098A/en
Priority to CO98053352A priority patent/CO4970697A1/es
Priority to PE1998000888A priority patent/PE116600A1/es
Publication of WO1999013849A1 publication Critical patent/WO1999013849A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/342—Alcohols having more than seven atoms in an unbroken chain
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4966—Triazines or their condensed 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/42—Colour properties
    • A61K2800/43—Pigments; Dyes
    • A61K2800/434—Luminescent, Fluorescent; Optical brighteners; Photosensitizers

Definitions

  • the present invention relates to a hair care composition comprising optical brighteners which alter the color of the hair, while enhancing the shininess of the hair, and protecting the hair from further damage. More specifically, the present invention relates to a hair care composition comprising optical brighteners and high melting point compounds.
  • Damaged hair is perceived by the consumer as unfavorable appearances and less manageability of the hair.
  • Such unfavorable appearances include alteration and fading of original color, less shine, and less luster.
  • a common way for alleviating the unfavorable appearances of damaged hair and to achieve appealing hair color is to dye the hair to the color desired.
  • Dying the hair would provide the consumer with a stable color of hair for a relatively long period.
  • dying the hair is generally time-consuming, cumbersome, and messy.
  • Dyestuff may also be chemically harsh to the hair, scalp, and skin.
  • the hair can be further damaged by dying.
  • hair dye products are not suitable for daily use.
  • dying can leave the hair with a dull appearance, making the hair look less shiny.
  • optical brighteners or compounds otherwise described by names such as fluorescent whitening agents, fluorescent brighteners, or fluorescent dyes, in the hair care field has been known in the art, such as in United States
  • a hair care composition comprising: (a) an effective amount of an optical brightener; (b) a high melting point compound; and (c) a carrier suitable for application to hair.
  • optical brighteners are compounds which absorb ultraviolet light and re- emit the energy in the form of visible light.
  • the optical brighteners useful herein have an absorption, preferably a major absorption peak, between a wavelength of about 1 nm and about 420nm, and an emission, preferably a major emission peak, between a wavelength of about 360nm and about 830nm; wherein the major absorption peak has a shorter wavelength than the major emission peak.
  • the optical brighteners useful herein have a major absorption peak between a wavelength of about 200nm and about 420nm, and a major emission peak between a wavelength of about 400nm and about 780nm.
  • Optical brighteners may or may not have minor absorption peaks in the visible range between a wavelength of about 360nm and about 830nm.
  • Optical brighteners can be described by other names in the art and in other industries, such as fluorescent whitening agents, fluorescent brighteners, and fluorescent dyes.
  • optical brighteners herein When applied to hair via suitable vehicles, optical brighteners herein provide benefits to the hair in three areas. First, optical brighteners herein alter the color of the hair by emitting light in the visible range. Second, optical brighteners herein enhance the shine of the hair by emitting light in the visible range. Third, optical brighteners herein protect the hair from ultraviolet light by absorbing ultraviolet light.
  • optical brighteners in general are based on the structures of aromatic and heteroaromatic systems which provide these unique characteristics.
  • the optical brighteners useful in the present invention can be classified according to their base structures, as described hereafter.
  • Preferable optical brighteners herein include polystyrylstilbenes, triazinstilbenes, hydroxycoumarins, aminocoumarins, triazoles, pyrazolines, oxazoles, pyrenes, porphyrins, and imidazoles.
  • optical brighteners herein are included in the hair care composition of the present invention at a level by weight of from about 0.001% to about 20%, more preferably from about 0.01 % to about 10%.
  • Polystyrylstilbenes are included in the hair care composition of the present invention at a level by weight of from about 0.001% to about 20%, more preferably from about 0.01 % to about 10%.
  • Polystyrylstilbenes are a class of compounds having two or more of the following base structure:
  • Polystyrylstilbenes useful in the present invention include those having formulae (1), (2) and (3):
  • R 101 is H, OH, SO 3 M, COOM, OSO3M, OPO(OH)OM, wherein M is H, Na, K, Ca, Mg, ammonium, mono-, di-, tri- or tetra-C ⁇ -C3o-alkylammonium, mono-, di- or tri-C-
  • R 104 and R105 independently, are CN, COO(C ⁇
  • each R 1 ⁇ independently, is H, or alkyl of 1 to 30 carbons; and wherein the compound has a trans-coplanar orientation or cis-coplanar orientation, preferably a trans-coplanar orientation.
  • Suitable polystyrylstilbenes include disodium-1 , 4'-bis(2-sulfostyryl) bisphenyl (C.I. Fluorescent Brightener 351) with tradename Tinopal CBS-X available from Ciba Specialty Chemicals, 1 ,4-bis(2-cyanostyryl)benzene (C.I. Fluorescent Brightener 199) with tradename Ultraphor RN available from BASF. Triazinstilbenes
  • Triazinstilbenes are a class of compounds having both triazin and stilbene structures in the same molecule.
  • Triazinstilbenes useful in the present invention include those having formulae (4):
  • RIO 7 and R108 independently, are phenylamino, mono- or disulfonated phenylamino, morpholino, N(CH2CH 2 OH) 2 , N(CH 3 )(CH2CH2 ⁇ H), NH 2 , N(C «
  • An" is an anion of a carboxylate, sulfate, sulfonate, or phosphate, and M is as previously defined, wherein the compound has a trans-coplanar orientation or cis-coplanar orientation; preferably R10?
  • each R108 is 2, 5-disulfophenylamino and each R108 is morpholino; or each R ⁇ O j S 2, 5-disulfophenylamino and each R108 J S N(C2H 5 ) 2 ; or each R107 is 3-sulfophenyl and each R 1 °8 is NH(CH2CH 2 OH) or N(CH2CH2OH)2; or each R 07 is 4-sulfophenyl and each R 08 is N(CH2CH2OH)2; and in each case, the sulfo group is SO3M in which M is sodium; wherein the compound has a trans-coplanar orientation.
  • Suitable triazinstilbenes include 4,4'-bis-[(4-anilino-6-bis(2- hydroxyethyl)amino-1 ,3,5-triazin-2-yl)amino]stilbene-2,2'-disulfonic acid with tradename Tinopal UNPA-GX available from Ciba Specialty Chemicals, 4,4'-bis- [(4-anilino-6-morpholine-1 ,3,5-triazin-2-yl)amino]stilbene-2,2'-disodium sulfonate with tradename Tinopal AMS-GX available from Ciba Specialty Chemicals, 4,4'- bis-[(4-anilino-6-(2-hydroxyethyl)methyl amino-1 ,3,5-triazin-2-yl)amino]stilbene- 2,2'-disodium sulfonate with tradename Tinopal 5BM-GX available from Ciba Specialty Chemicals, 4'4-
  • Hydroxycoumahns are a class of compounds having the following base coumarin structure and having at least one hydroxy moiety:
  • Hydroxycoumahns useful in the present invention include those having formulae (5):
  • R201 j s H, OH, Cl, CH 3 , CH2COOH, CH2SO3H, CH2OSO3H, or CH2 ⁇ PO(OH)OH
  • R205 anc j R206 are independently, phenylamino, mono- or disulfonated phenylamino, morpholino, N(CH 2 CH 2 OH)2, N(CH 3 )(CH 2 CH 2 OH), NH2, N(C ⁇
  • Suitable hydroxycoumarins include 6,7-dihydroxycoumarin available from Wako Chemicals, 4-methyl-7-hydroxycoumarin available from Wako Chemicals, 4-methyl-6,7-dihydroxycoumarin available from Wako Chemicals, esculin available from Wako Chemicals, and umbelliferone (4-hydroxycoumarin) available from Wako Chemicals.
  • Aminocoumarins are a class of compounds having the base coumarin structure and having at least one amino moiety.
  • Aminocoumarins useful in the present inventions include those having formulae (8):
  • R210 are independently H, NH2, N(C ⁇ -C3oalkyl)2, NHC-
  • Suitable aminocoumarins include 4-methyl-7,7'-diethylamino coumarin with tradename Calcofluor-RWP available from BASF, 4-methy 1-7,7'- dimethylamino coumarin with tradename Calcofluor-LD available from BASF.
  • Triazoles are a class of compounds having the following base structure:
  • Triazoles useful in the present inventions include those having formulae (9) through (12) and (15) through (20):
  • R 301 and R 3 ⁇ 2 independently, are H, C ⁇
  • An- and M are as previously defined, wherein the compound has a trans-coplanar orientation or cis-coplanar orientation; preferably R301 JS phenyl, R 3 ⁇ 2 js H and M is sodium; wherein the compound has a trans- coplanar orientation;
  • R 303 is H or Cl;
  • R 304 is SO3M, S ⁇ 2N(C ⁇
  • R 305 is H, SO3M, COOM, OSO3M, or OPO(OH)OM; and M is as previously defined, wherein the compound has a trans-coplanar orientation or cis-coplanar orientation; preferably R 3 03 anc
  • each of R 3 06 an( j R 3 12 independently represents H, a sulfonic acid group or the salts, esters or amides thereof, a carboxylic acid group or the salts, esters or amides thereof, a cyano group, a halogen atom, an unsubstituted or substituted alkylsulfonyl, arylsulfonyl, alkyl, alkoxy, aralkyl, aryl, aryloxy, aralkoxy or cycloalkyl radical, an unsubstituted or substituted 5-membered heterocyclic ring containing 2 to 3 nitrogen atoms or one oxygen atom and 1 or 2 nitrogen atoms, or together with R 3 ⁇ 7 and R ⁇ 3 they represent a methylenedioxy, ethylenedioxy, methylenoxymethylenoxy, trimethylene, tetramethylene, propenylene, butenylene or butadienylene radical, each of R 3 ⁇
  • Q1 denotes one of the ring systems (13) or (14);
  • R 3 ⁇ 7 denotes H, alkyl with 1 to 30 carbon atoms, cyclohexyl, phenylalkyl with C1-C30 carbon atoms in the alkyl part, phenyl, alkoxy with 1 to 30 carbon atoms, or Cl, or, conjointly with R 3 18_ denotes alkylene with 3 to 30 carbon atoms
  • R 3 ⁇ 8 denotes H or alkyl with 1 to 30 carbon atoms or, conjointly with R 3 17, denotes alkylene with 3 to 30 carbon atoms
  • R 3 ⁇ denotes H or methyl
  • R 3 20 denotes H, alkyl with 1 to 30 carbon atoms, phenyl, alkoxy with 1 to 30 carbon atoms, or Cl, or, conjointly with R 3 21 , denotes a fused benzene ring
  • R821 denotes H or Cl or conjointly with R 3 20 ⁇ denotes a fused benzene ring
  • R 32 2 denotes H, Cl, methyl, phenyl, benzyl, cyclohexyl or methoxy
  • R323 denotes H or methyl
  • Z denotes O or S
  • the compound has a trans-coplanar orientation or cis-coplanar orientation, preferably a trans-coplanar orientation
  • R 3 24 denotes H, Cl, alkyl with 1 to 30 carbon atoms, phenylalkyl with 1 to 30 carbon atoms, phenyl or alkoxy with 1 to 30 carbon atoms, or R 3 24 conjointly with R 3 25 denotes a fused benzene radical
  • R 3 25 denotes H or methyl or R 3 25 conjointly with R 3 24 denotes a fused benzene radical
  • R326 denotes H, alkyl with 1 to 30 carbon atoms, alkoxy with 1 to 30 carbon atoms, Cl, carbalkoxy with 1 to 30 carbon atoms or alkylsulfonyl with 1 to 30 carbon atoms
  • R 3 27 denotes H, Cl, methyl or methoxy; wherein the compound has a trans-coplanar orientation or cis-coplanar orientation, preferably a trans-coplanar orientation.
  • Suitable triazoles include 2-(4-styryl-3-sulfophenyl)-2H-naptho[1 ,2-d] triazole (C.I. Fluorescent Brightener 46) with tradename Tinopal RBS available from Ciba Specialty Chemicals. Pyrazolines
  • Pyrazolines are a class of compounds having the following base structure:
  • R 401 is H, Cl or N(C ⁇
  • R 402 is H, Cl, S0 3 M, S0 2 NH 2 , S ⁇ 2NH-(C ⁇ -C3oalkyl), COO-C ⁇
  • An-, R 4 03 an d R 404 are the same or different and each is H, C ⁇ -C3 ⁇ alkyl or phenyl and R405 j s H or Cl; and
  • An" and M are as previously defined, preferably R 4 01 is Cl, R402 js SO2CH2 CH2N + H(C ⁇ -C -alkyl)2An- in which An" is phosphite and R 403 , R
  • Suitable pyrazolines include 1-(4-amidosulfonylphenyl)-3-(4-chlorophenyl)- 2-pyrazoline (Cl. Fluorescent Brightener 121) with tradename Blankophor DCB available from Bayer, 1-[4-(2-sulfoethylsulfonyl)phenyl]-3-(4-chlorophenyl)-2- pyrazoline, 1-[4-(2-sulfoethylsulfonyl)phenyl]-3-(3,4-dichloro-6-methylphenyl)-2- pyrazoline, 1- ⁇ 4- ⁇ N-[3-(N,N,N-trimethylammonio)propyl]-amidosulfonyl ⁇ phenyl>- 3-(4-chlorophenyl)-2-pyrazoline methylsulfate, and 1- ⁇ 4- ⁇ 2-[1-methyl-2-(N,N- dimethylamino)ethoxy]ethyls
  • Oxazoles are a class of compounds having the following base structure:
  • Oxazoles useful in the present inventions include those having formulae (24), (25), (26) and (27):
  • R 501 and R 50 independently, are H, Cl, C ⁇ -C3oalkyl or SO2-C1-C30- alkyl, wherein the compound has a trans-coplanar orientation or cis-coplanar orientation; preferably R 5 ⁇ is 4-CH3 and R 5 °2 j S 2-CH3 wherein the compound has a trans-coplanar orientation;
  • R 505 and R 506 are the atoms required to form a fused benzene ring or R506 an d R508 independently, are H or C ⁇
  • R ⁇ 07 is H, C ⁇ -C3oalkyl or phenyl; wherein the compound has a trans-coplanar orientation or cis-coplanar orientation; preferably R504 JS a 4-phenyl group and each of R505 to R508 J S H; wherein the compound has a trans-coplanar orientation; and
  • R509 denotes H, Cl, alkyl with 1 to 30 carbon atoms, cyclohexyl, phenylalkyl with 1 to 3 carbon atoms in the alkyl part, phenyl or alkoxy with 1 to 30 carbon atoms
  • R 5 10 denotes H or alkyl with 1 to 30 carbon atoms
  • Q 5 denotes a radical
  • R ⁇ H represents H, alkyl with 1 to 30 carbon atoms, alkoxy with 1 to 30 carbon atoms, Cl, carbalkoxy with 1 to 30 carbon atoms, unsubstituted sulfamoyl or sulfamoyl which is monosubstituted or disubstituted by alkyl or hydroxyalkyl with 1 to 30 carbon atoms or represents alkylsulfonyl with 1 to 30 carbon atoms; wherein the compound has a trans-coplanar orientation or cis-coplanar orientation, preferably a trans-coplanar orientation.
  • Suitable oxazoles include 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene, and 2-(4-methoxycarbonylstyryl)benzoxazole.
  • Pyrenes Pyrenes useful in the present invention include those having formulae (28) and (29):
  • each R601 f independently, is C ⁇ -G3oalkoxy; preferably methoxy; and
  • each R802 independently, is H, OH, or SO3M, wherein M is as previously defined, sulfonated phenylamino, or anilino.
  • Suitable pyrenes include 2,4-dimethoxy-6-(1'-pyrenyl)-1 ,3,5-triazine (Cl. Fluorescent Brightener 179) with tradename Fluolite XMF, 8-hydroxy-1 ,3,6- pyrenetrisulfonic acid (D&C Green No.8), and 3-hydroxy-5,8,10-trisulphanilic pyrene. Porphyrins
  • Porphyrins useful in the present invention include those having formulae (30), (31), and (32):
  • R 701 is CH3 or CHO
  • R 702 is H or COOC1-C30 alkyl
  • R 703 is H or an alkyl group having 1 to 30 carbons
  • each R 70 independently, is H, SO3M, COOM, OSO3M, or OPO(OH)OM, wherein M is as previously defined, halide, or alkyl of 1 to 30 carbons; and Q8 is Cu, Mg, Fe, Cr, Co, or mixtures thereof with cationic charges.
  • Suitable porphyrins include porphyrin available from Wako Chemicals and Copper II phthalocyanine available from Wako Chemicals. Imidazoles
  • Imidazoles are a class of compounds having the following base structure:
  • Imidazoles useful in the present invention include those having formulae (33):
  • Suitable imidazoles include those with tradename of Cl. Fluorescence
  • compositions comprise a high melting point compound having a melting point of at least about 25°C selected from the group consisting of fatty alcohols, fatty acids, fatty alcohol derivatives, fatty acid derivatives, hydrocarbons, steroids, and mixtures thereof. Without being bound by theory, it is believed that these high melting point compounds cover the hair surface and reduce friction, thereby resulting in providing smooth feel on the hair and ease of combing. It is understood by the artisan 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.
  • a given classification is not intended to be a limitation on that particular compound, but is done so for convenience of classification and nomenclature. Further, it is understood by the artisan that, depending on the number and position of double bonds, and length and position of the branches, certain compounds having certain required carbon atoms may have a melting point of less than about 25°C Such compounds of low melting point are not intended to be included in this section. Nonlimiting examples of the high melting point compounds 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 14 to about
  • fatty alcohols can be straight or branched chain alcohols and can be saturated or unsaturated.
  • fatty alcohols include, cetyl alcohol, stearyl alcohol, behenyl 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 requirements herein. Also included herein are salts of these fatty acids.
  • Nonlimiting examples of fatty acids include lauric acid, palmitic acid, stearic acid, behenic acid, sebacic acid, and mixtures thereof.
  • the fatty alcohol derivatives and fatty acid derivatives useful herein include alkyl ethers of fatty alcohols, alkoxylated fatty alcohols, alkyl ethers of alkoxylated fatty alcohols, esters of fatty alcohols, fatty acid esters of compounds having esterifiable hydroxy groups, hydroxy-substitued fatty acids, and mixtures thereof.
  • Nonlimiting examples of fatty alcohol derivatives and fatty acid derivatives include materials such as methyl stearyl ether; 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 10, which are ethylene glycol ethers of steareth alcohol, wherein the numeric designation indicates the number of ethylene glycol moieties present; ceteareth 1 through ceteareth-10, which are the ethylene glycol ethers of ceteareth alcohol, i.e.
  • Steroids useful herein include compounds such as cholesterol.
  • High melting point compounds of a single compound of high purity are preferred.
  • Single compounds of pure fatty alcohols selected from the group of pure cetyl alcohol, stearyl alcohol, and behenyl alcohol are highly preferred.
  • pure herein, what is meant is that the compound has a purity of at least about 90%, preferably at least about 95%.
  • high melting point compounds useful herein include: cetyl alchol, stearyl alcohol, and behenyl alcohol having tradenames KONOL series available from New Japan Chemical (Osaka, Japan), and NAA series available from NOF (Tokyo, Japan); pure behenyl alcohol having tradename 1-DOCOSANOL available from WAKO (Osaka, Japan), various fatty acids having tradenames NEO-FAT available from Akzo (Chicago Illinois, USA), HYSTRENE available from Witco Corp. (Dublin Ohio, USA), and DERMA available from Vevy (Genova, Italy); and cholesterol having tradename NIKKOL AGUASOME LA available from Nikko.
  • the high melting point compound is present in the hair care compositions herein at a level of about 0.01% to about 20%.
  • the hair care composition of the present invention comprises a carrier.
  • the level and species of the carrier are selected according to the compatibility with other components, and desired characteristic of the product. For example, a high percentage of volatile solvents of low boiling point and/or propellant are suitably used for product forms aimed to be left on the hair. On the other hand, water solutions of volatile and non-volatile solvents are suitably used for product forms aimed to be rinsed off the hair after washing or treating the hair with the product.
  • the carrier useful in the present invention include volatile solvents, nonvolatile solvents, propellants, and mixtures thereof.
  • Volatile solvents useful herein include water, lower alkyl alcohols having from 1 to 3 carbons, and hydrocarbons having from about 5 to about 8 carbons.
  • the preferred volatile solvents are water, ethanol, isopropanol, pentane, hexane, and heptane.
  • the water useful herein include deionized water and water from natural sources containing mineral cations. Deionized water is preferred.
  • Non-volatile solvents useful herein include alkyl alcohols having more than 3 carbons, and polyhydric alcohols.
  • the polyhydric alcohols useful herein include 1 ,2-propane diol or propylene glycol, 1 ,3-propane diol, hexylene glycol, glycerin, diethylene glycol, dipropylene glycol, 1 ,2-butylene glycol, and 1 ,4- butylene glycol.
  • Propellants may be used for mousse and hair spray product forms. Propellants, when used in the present invention, are selected depending on variables such as the remainder of components, the package, and whether the product is designed to be used standing or invert.
  • Propellants useful herein include fluorohydrocarbons such as difluoroethane 152a (supplied by DuPont), dimethylether, and hydrocarbons such as propane, isobutane, n-butane, mixtures of hydrocarbons such as LPG (liquefied petroleum gas), carbon dioxide, nitrous oxide, nitrogen, and compressed air.
  • fluorohydrocarbons such as difluoroethane 152a (supplied by DuPont), dimethylether, and hydrocarbons such as propane, isobutane, n-butane, mixtures of hydrocarbons such as LPG (liquefied petroleum gas), carbon dioxide, nitrous oxide, nitrogen, and compressed air.
  • the hair care compositions of the present invention may comprise a component which characterizes the form of the product.
  • Product forms useful herein include, but are not limited to, shampoo, conditioner, treatment, mousse, spray, lotion, gel, and cream products, all of which can be designed for rinse-off or leave-on convenience.
  • Product functions useful herein include, but are not limited to, cleansing, and conditioning products. For example, a detersive surfactant, a hair conditioning agent, and mixtures thereof may be comprised. The components and their levels are selected by one skilled in the art depending on the desired characteristic of the product.
  • compositions herein may include a detersive surfactant.
  • the detersive surfactants herein are those suitable for cleansing the hair.
  • Detersive surfactants useful herein include anionic surfactants, amphoteric and zwitterionic surfactants, and nonionic surfactants.
  • the detersive surfactants when present, are preferably included at a level of from about 0.01% to about 75% by weight of the composition. Two or more surfactants can be used.
  • Anionic surfactants useful herein include alkyl and alkyl ether sulfates. These materials have the respective formulae ROSOgM and RO(C 2 H 4 0) ⁇ S0 3 M, 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, alkanolammonium (e.g., triethanolammonium), 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 or surfactants 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 hyd ration, 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 Technology, pp. 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 8 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 are sodium and ammonium salts of coconut alkyl thethylene 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 8 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 of 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-SO3-M] where R ⁇ 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 8 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-paraffins, having about 8 to about 24 carbon atoms, preferably about 8 to about 18 carbon atoms and a sulfonating agent, e.g., SO3, H2SO4, obtained according to known sulfonation methods, including bleaching and hydrolysis.
  • a sulfonating agent e.g., SO3, H2SO4
  • 8 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 for use in the shampoo compositions are the ⁇ -alkyloxy 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 in the shampoo compositions 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 in the shampoo compositions 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, ammonium cocoyl sulfate, ammonium lauroyl sulfate, sodium cocoyl sulfate, sodium lauroyl sulfate, potassium cocoyl sulfate, potassium la
  • anionic surfactants for use herein include polyhydrophilic anionic surfactants.
  • polyhydrophilic herein, is meant a surfactant that has at least two hydrophilic groups which provide a hydrophilic nature.
  • Polyhydrophilic surfactants useful herein are only those having at least two hydrophilic groups in the molecule, and is not intended to encompass those which only have one hydrophilic group.
  • One molecule of the polyhydrophilic anionic surfactant herein may comprise the same hydrophilic groups, or different hydrophilic groups.
  • the polyhydrophilic anionic surfactants comprise at least one group selected from the group consisting of carboxy, hydroxy, sulfate, sulfonate, and phosphate.
  • Suitable polyhydrophilic anionic surfactants are those which comprise at least one of a carboxy, sulfate, or sulfonate group, more preferably those which comprise at least one carboxy group.
  • Nonlimiting examples of polyhydrophilic anionic surfactants include N-acyl-
  • L-glutamates such as N-cocoyl-L-glutamate and, N-lauroyl-L-glutamate, lauhmino diproprionate, N-acyl-L-aspartate, di-(N-lauroyl N-methyl taurate), polyoxyethylene laurylsulfosuccinate, disodium N-octadecylsulfosuccinate; disodium lauryl sulfosuccinate; diammonium lauryl sulfosuccinate; tetra sodium N-(1,2-dicarboxyethyl)-N-octadecylsulfosuccinate; the diamyl ester of sodium sulfosuccinic acid; the dihexyl ester of sodium sulfosuccinic acid; and the dioctyl ester of sodium sulfosuccinic acid, and 2-cocoalkyl N-carboxyethy
  • R is an alkyl of 8 to 18 carbons.
  • Other polyhydrophilic anionic surfactants include olefin sulfonates having about 10 to about 24 carbon atoms.
  • olefin sulfonates is used herein to mean compounds which can be produced by the sulfonation of alpha-olefins by means of uncomplexed sulfur trioxide, followed by neutralization of the acid reaction mixture in conditions such that any sulfones which have been formed in the reaction are hydrolyzed 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 SO2, chlorinated hydrocarbons, etc., when used in the liquid form, or by air, nitrogen, gaseous SO2, etc., when used in the gaseous form.
  • the -olefins from which the olefin sulfonates are derived are mono-olefins having about 8 to about 24 carbon atoms, preferably about 10 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 ⁇ -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.
  • polyhydrophilic anionic surfactants are amino acid surfactants which are surfactants that have the basic chemical structure of an amino acid compound, i.e., that contains a structural component of one of the naturally-occurring amino acids. It is understood by the artisan that some surfactants may be regarded as both a polyhydrophilic anionic surfactant, and an amino acid surfactant. These surfactants are suitable anionic surfactants.
  • Nonlimiting examples of amino acid surfactants include, N- cocoylalaninate, N-acyl-N-methyl- ⁇ -alanate, N-acylsarcosinate; N-alkylamino propionates and N-alkyliminodipropionates, specific examples of which include N-lauryl- ⁇ -amino propionic acid or salts thereof, and N-lauryl- ⁇ -imino- dipropionate, N-acyl-DL-alaninate, sodium lauryl sarcosinate, sodium lauroyl sarcosinate, lauryl sarcosine, cocoyl sarcosine, N-acyl-N-methyl taurate, lauroyl taurate, and lauroyl lactylate.
  • anionic surfactants suitable are N-acyl-L- glutamate with a tradename AMISOFT CT-12S, N-acyl potassiumglycine with a tradename AMILITE GCK-12, lauroyl glutamate with a tradename AMISOFT LS- 11 , and N-acyl-DL-alaninate with tradename AMILITE ACT12 supplied by Ajinomoto; acylaspartate with tradenames ASPARACK and AAS supplied by Mitsubishi Chemical; and acyl derivaties of tradename ED3A supplied by Hampshire Chemical Corp.
  • the counter ion of anionic surfactants may be polyvalent cations.
  • Cationic conditioning agents may be included in the present composition to provide a shampoo which both cleanse and condition the hair from a single product.
  • Coacervate formulation is dependent upon a variety of criteria such as molecular weight, component concentration, and ratio of interacting ionic components ionic strength, charge density of the cationic and anionic components, pH, and temperature. Coacervate systems and the effect of these parameters are known in the art.
  • the anionic surfactants and the polyvalent metal cations at certain levels are believed to readily deposit on the hair upon diluting the coacervate with abundant water, i.e., rinsing of the shampoo.
  • the coacervates provide two major effects to the present shampoo composition.
  • CMC Critical Micelle Concentration
  • the reduction of the CMC relates to reduction of the surface tension, thereby improving lather performance.
  • the cationic conditioning agents in the composition are mainly delivered to the hair via these coacervates, expansion of the coacervate region results in delivery of more cationic conditioning agents to the hair. Consequently, compositions which both cleanse and condition the hair from a single product, which have improved overall conditioning benefits and improved lathering are provided.
  • Amphotehc surfactants for use herein include the derivatives of aliphatic secondary and tertiary amines in which the aliphatic radical is straight or branched and one of the 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.
  • an anionic water solubilizing group e.g., carboxy, sulfonate, sulfate, phosphate, or phosphonate.
  • Zwitterionic surfactants for use herein 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,
  • 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 phosphorus atom;
  • R is an alkylene or hydroxyalkylene of from
  • 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.
  • Sultaines including amidosultaines, include for example, cocodimethylpropylsultaine, stearyldimethylpropylsultaine, lauryl-bis-(2- hydroxyethyl)propylsultaine and the like; and the amidosultaines such as cocamidodimethylpropylsultaine, stearylamidododimethylpropylsultaine, laurylamido-bis-(2-hydroxyethyl)propylsultaine, and the like.
  • amidohydroxysultaines such as the Cs-Ci8 hydrocarbylamidopropyl hydroxysultaines, especially C8-C14 hydrocarbylamidopropylhydroxysultaines, e.g., laurylamidopropylhydroxysultaine and cocamidopropylhydroxysultaine.
  • Cs-Ci8 hydrocarbylamidopropyl hydroxysultaines especially C8-C14 hydrocarbylamidopropylhydroxysultaines, e.g., laurylamidopropylhydroxysultaine and cocamidopropylhydroxysultaine.
  • 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 RNH(CH2)nCOOM, the iminodialkanoates of the formula RN[(CH2)mCOOM]2 an d mixtures thereof; wherein n and m are numbers from 1 to about 4, R is C3 - C22 alkyl or alkenyl, and M is hydrogen, alkali metal, alkaline earth metal, ammonium or alkanolammonium.
  • amphoteric surfactants include those represented by the formula :
  • R1 is Cs - C22 alkyl or alkenyl, preferably C8 - C-
  • R ⁇ and R 3 is independently selected from the group consisting of hydrogen, -CH2CO2M, - CH2CH2OH, -CH 2 CH 2 OCH2CH 2 COOM, or -(CH 2 CH2 ⁇ ) m H wherein m is an integer from 1 to about 25, and R 4 is hydrogen, -CH2CH2OH, or CH2CH2OCH2CH2COOM, Z is CO2M or CH2CO2M, 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 MIRANOL 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 R2. All such variations and species are meant to be encompassed by the above formula.
  • Examples of surfactants of the above formula are monocarboxylates and di-carboxylates. Examples of these materials include cocoamphocarboxypropionate, cocoamphocarboxypropionic acid, cocoamphocarboxyglycinate (alternately referred to as cocoamphodiacetate), and cocoamphoacetate.
  • amphoteric surfactants include those sold under the trade names MIRANOL C2M CONC N.P., MIRANOL C2M CONC O.P., MIRANOL C2M SF, MIRANOL CM SPECIAL (Miranol, Inc.); ALKATERIC 2CIB (Alkaril Chemicals); AMPHOTERGE W-2 (Lonza, Inc.); MONATERIC CDX-38, MONATERIC CSH-32 (Mona Industries); REWOTERIC AM-2C (Rewo Chemical Group); and SCHERCOTERIC MS-2 (Scher Chemicals).
  • Betaine surfactants i.e. zwitterionic surfactants, suitable for use in the conditioning compositions are those represented by the formula: O R 4 R 2
  • R1 is a member selected from the group consisting of
  • R2 is lower alkyl or hydroxyalkyl;
  • R 3 is lower alkyl or hydroxyalkyl;
  • R 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 8 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 substituents 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, lauryldimethylcarboxymethylbetaine, lauryldimethyl- ⁇ -carboxyethylbetaine, cetyldimethylcarboxymethylbetaine, lauryl- bis-(2-hydroxyethyl)-carboxymethylbetaine, stearyl-bis-(2-hydroxypropyl) carboxymethylbetaine, oieyldimethyl- ⁇ -carboxypropylbetaine, lauryl-bis-(2- hydroxypropyl)- ⁇ -carboxyethylbetaine, etc.
  • alkylbetaines such as cocodimethylcarboxymethylbetaine, lauryldimethylcarboxymethylbetaine, lauryldimethyl- ⁇ -carboxyethylbetaine, cetyldimethylcarboxymethylbetaine, lauryl- bis-(2-hydroxy
  • the sulfobetaines may be represented by cocodimethylsulfopropylbetaine, stearyldimethylsulfopropyl betaine, lauryl-bis-(2-hydroxyethyl)-sulfopropylbetaine, and the like.
  • amido betaines and amidosulfobetaines useful in the conditioning compositions include the amidocarboxybetaines, such as cocamido dimethylcarboxymethylbetaine, laurylamidodimethylcarboxymethylbetaine, cetylamidodimethylcarboxymethylbetaine, laurylamido-bis-(2-hydroxyethyl) carboxymethylbetaine, cocamido-bis-(2-hydroxyethyl)-carboxymethylbetaine, etc.
  • amidosulfobetaines may be represented by cocamidodimethyl sulfopropylbetaine, stearylamidodimethylsulfopropylbetaine, laurylamido-bis-(2- hydroxyethyl)-sulfopropylbetaine, and the like.
  • compositions 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;
  • R1 R2R 3 N ⁇ O long chain tertiary amine oxides of the formula [ R1 R2R 3 N ⁇ O ] where R1 contains an alkyl, alkenyl or monohydroxy 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, and R2 and R 3 contain from about 1 to about 3 carbon atoms and from 0 to about 1 hydroxy group, e.g., methyl, ethyl, propyl, hydroxyethyl, or hydroxypropyl radicals; (5) long chain tertiary phosphine oxides of the formula [RR'R"P ⁇ O] where 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
  • alkyl polyglycosides examples of which are described in U.S. Patent 4,565,647, which is incorporated herein by reference in its entirety, and which discloses 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 (8) polyoxyethylene alkyl ethers such as those of the formula
  • RO(CH2CH2)nH and polyethylene glycol (PEG) glyceryl fatty esters such as those of the formula R(0)OCH2CH(OH)CH2(OCH2CH2) 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.
  • Conditioning agents useful herein include cationic surfactants, oily compounds, cationic polymers, silicone compounds, and nonionic polymers. Conditioning agents may be present in the compositions herein either in combination with detersive surfactant, or without detersive surfactant.
  • the cationic surfactants useful herein are any known to the artisan.
  • cationic surfactants useful herein are those corresponding to the general formula (I):
  • Rl , R 2 , R3_ a nd R 4 is selected from an aliphatic group of from 8 to 30 carbon atoms or an aromatic, alkoxy, polyoxyalkylene, alkylamido, hydroxyalkyl, aryl or alkylaryl group having up to about 22 carbon atoms, the remainder of R1 , R 2 , 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.
  • 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 , R 3 , and R 4 are independently selected from C ⁇
  • Nonlimiting examples of cationic surfactants useful include the materials having the following CTFA designations: quaternium-8, quaternium-24, quaternium-26, quaternium-27, quaternium-30, quaternium-33, quaternium-43, quaternium-52, quaternium-53, quaternium-56, quaternium-60, quaternium-62, quaternium-70, quaternium-72, quaternium-75, quaternium-77, quaternium-78, quaternium-80, quaternium-81 , quaternium-82, quaternium-83, quaternium-84, and mixtures thereof.
  • CTFA designations quaternium-8, quaternium-24, quaternium-26, quaternium-27, quaternium-30, quaternium-33, quaternium-43, quaternium-52, quaternium-53, quaternium-56, quatern
  • hydrophilically substituted cationic surfactants in which at least one of the substituents contain one or more aromatic, ether, ester, amido, or amino moieties present as substituents or as linkages in the radical chain, wherein at least one of the R 1 - R4 radicals contain one or more hydrophilic moieties selected from alkoxy (preferably C-i - C3 alkoxy), polyoxyalkylene (preferably C-
  • the hydrophilically substituted cationic conditioning surfactant contains from 2 to about 10 nonionic hydrophile moieties located within the above stated ranges.
  • Preferred hydrophilically substituted cationic surfactants include those of the formula (II) through (VII) below: z 1
  • n is from 8 to about 28, x+y is from 2 to about 40, Z "1 is a short chain alkyl, preferably a C1 - C3 alkyl, more preferably methyl, or - (CH2CH2 ⁇ ) z H wherein x+y+z is up to 60, and X is a salt forming anion as defined above; R 6 R 8
  • m is 1 to 5
  • R5, R6, and R 7 are independently an C ⁇
  • the remainder are - CH2CH2OH
  • one or two of R 8 , R 9 , and R1° are independently an C-
  • remainder are - CH2CH2OH
  • X is a salt forming anion as mentioned above;
  • z2 is an alkyl, preferably a C-j - C3 alkyl, more preferably methyl
  • 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
  • R11 and Rl2 independently, are substituted or unsubstituted hydrocarbyls, preferably C-12 - C20 alkyl or alkenyl
  • X is a salt forming anion as defined above;
  • R1 3 is a hydrocarbyl, preferably a C1 - C3 alkyl, more preferably methyl
  • Z4 and Z 5 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;
  • R1 an d R15 independently, are C-
  • Nonlimiting examples of hydrophilically substituted cationic surfactants useful include the materials having the following CTFA designations: quaternium-16, quaternium- 61 , quaternium-71 , quaternium-79 hydrolyzed collagen, quaternium-79 hydrolyzed keratin, quaternium-79 hydrolyzed milk protein, quaternium-79 hydrolyzed silk, quaternium-79 hydrolyzed soy protein, and quaternium-79 hydrolyzed wheat protein.
  • Highly preferred compounds include commercially available materials of the following tradenames; 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 ICI Americas.
  • Salts of primary, secondary, and tertiary fatty amines are also suitable cationic surfactants.
  • the alkyl groups of such amines preferably have from about 12 to about 22 carbon atoms, and can be substituted or unsubstituted. Particularly useful are amido substituted tertiary fatty amines.
  • Such amines include stearamidopropyldimethylamine, stearamidopropyldiethylamine, stearamidoethyldiethylamine, stearamidoethyldimethylamine, palmitamidopropyldimethylamine, palmitamidopropyldiethylamine, palmitamidoethyldiethylamine, palmitamidoethyldimethylamine, behenamidopropyldimethylamine, behenamidopropyldiethylamine, behenamidoethyldiethylamine, behenamidoethyldimethylamine, arachidamidopropyldimethylamine, arachidamidopropyldiethylamine, arachidamidoethyldiethylamine, arachidamidoethyldimethylamine, diethylaminoethylstearamide.
  • dimethylstearamine dimethylsoyamine, soyamine, myristylamine, tridecylamine, ethylstearylamine, N-tallowpropane diamine, ethoxylated (with 5 moles of ethylene oxide) stearylamine, dihydroxyethylstearylamine, and arachidylbehenylamine.
  • These amines can also be used in combination with acids such as L-glutamic acid, lactic acid, hydrochloric acid, malic acid, succinic acid, acetic acid, fumaric acid, tartaric acid, citric acid, L-glutamic hydrochloride, and mixtures thereof; more preferably L-glutamic acid, lactic acid, citric acid.
  • Cationic amine surfactants included among those useful are disclosed in U.S. Patent 4,275,055, Nachtigal, et al., issued June 23, 1981 , which is incorporated by reference herein in its entirety.
  • the cationic surfactants for use herein may also include a plurality of ammonium quaternary moieties or amino moieties, or a mixture thereof.
  • compositions comprise an oily compound having a melting point of not more than about 25°C selected from the group consisting of a first oily compound, a second oily compound, and mixtures thereof.
  • the oily compounds useful herein may be volatile or nonvolatile. Without being bound by theory, it is believed that, the oily compounds may penetrate the hair to modify the hydroxy bonds of the hair, thereby resulting in providing softness and flexibility to the hair.
  • the oily compound may comprise either the first oily compound or the second oily compound as described herein. Preferably, a mixture of the first oily compound and the second oily compound is used.
  • the oily compounds of this section are to be distinguished from the high melting point compounds described above. Nonlimiting examples of the oily compounds 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 include 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 alcohols, preferably unsaturated alcohols. Nonlimiting examples of these compounds include oleyl alcohol, palmitoleic alcohol, isostearyl alcohol, isocetyl alchol, undecanol, octyl dodecanol, octyl decanol, octyl alcohol, caprylic alcohol, decyl alcohol and lauryl alcohol.
  • the fatty acids useful herein include those having from about 10 to about
  • fatty acids can be straight or branched chain acids and can be saturated or unsaturated.
  • Suitable fatty acids include, for example, oleic acid, linoleic acid, isostearic acid, linolenic acid, ethyl linolenic acid, ethyl linolenic acid, arachidonic acid, and ricinolic acid.
  • the fatty acid derivatives and fatty alcohol derivatives are defined herein to include, for example, esters of fatty alcohols, alkoxylated fatty alcohols, alkyl ethers of fatty alcohols, alkyl ethers of alkoxylated fatty alcohols, and mixtures thereof.
  • Nonlimiting examples of fatty acid derivatives and fatty alcohol derivatives include, for example, methyl linoleate, ethyl linoleate, isopropyl linoleate, isodecyl oleate, isopropyl oleate, ethyl oleate, octyldodecyl oleate, oleyl oleate, decyl oleate, butyl oleate, methyl oleate, octyldodecyl stearate, octyldodecyl isostearate, octyldodecyl isopalmitate, octyl isopelargonate, octyl pelargonate, hexyl isostearate, isopropyl isostearate, isodecyl isononanoate, Oleth-2, pentaeryth
  • first oily compounds useful herein include: oleyl alcohol with tradename UNJECOL 90BHR available from New Japan Chemical, pentaerythritol tetraisostearate and trimethylolpropane triisostearate with tradenames KAKPTI and KAKTTI available from Kokyu Alcohol (Chiba, Japan), pentaerythritol tetraoleate having the same tradename as the compound name available from New Japan Chemical, trimethylolpropane trioleate with a tradename ENUJERUBU series available from New Japan Chemical, various liquid esters with tradenames SCHERCEMOL series available from Scher, and hexyl isostearate with a tradename HIS and isopropryl isostearate having a tradename ZPIS available from Kokyu Alcohol.
  • the second oily compounds useful herein include straight chain, cyclic, and branched chain hydrocarbons which can be either saturated or unsaturated, so long as they have a melting point of not more than about 25°C These hydrocarbons have from about 12 to about 40 carbon atoms, preferably from about 12 to about 30 carbon atoms, and preferably from about 12 to about 22 carbon atoms. Also encompassed herein are polymeric hydrocarbons of alkenyl monomers, such as polymers of C2-6 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. 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.
  • Preferred for use herein are hydrocarbons selected from the group consisting of mineral oil, isododecane, isohexadecane, polybutene, polyisobutene, and mixtures thereof.
  • second oily compounds useful herein include isododecane, isohexadeance, and isoeicosene with tradenames PERMETHYL 99A, PERMETHYL 101 A, and PERMETHYL 1082, available from Presperse (South Plainfield New Jersey, USA), a copolymer of isobutene and normal butene with tradenames INDOPOL H-100 available from Amoco Chemicals (Chicago Illinois, USA), mineral oil with tradename BENOL available from Witco, isoparaffin with tradename ISOPAR from Exxon Chemical Co.
  • the term "polymer” shall include materials whether made by polymerization of one type of monomer or made by two (i.e., copolymers) or more types of monomers.
  • the cationic polymer is a water-soluble cationic polymer.
  • water soluble cationic polymer is 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 (distilled or equivalent) at 25°C
  • the preferred polymer will be sufficiently soluble to form a substantially clear solution at 0.5% concentration, more preferably at 1.0% concentration.
  • the 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 cationic nitrogen-containing moieties such as quaternary ammonium or cationic amino moieties, and mixtures thereof.
  • the cationic charge density is preferably at least about 0.1 meq/gram, more preferably at least about 1.5 meq/gram, even more preferably at least about 1.1 meq/gram, still more preferably at least about 1.2 meq/gram.
  • Cationic charge density of the cationic polymer can be determined according to the Kjeldahl Method. Those skilled in the art will recognize that the charge density of amino-containing polymers may 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 cationic polymers so long as the water solubility criteria is met. Suitable counterions include halides (e.g., Cl, Br, I, or F, preferably Cl, 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 cationic polymer can comprise copolymers, terpolymers, etc. of quaternary ammonium or cationic amine-substituted monomer units and other non-cationic units referred to herein as spacer monomer units.
  • spacer monomer units Such polymers are known in the art, and a variety can be found in the CTFA Cosmetic Ingredient Dictionary, 3rd edition, edited by Estrin, Crosley, and Haynes, (The Cosmetic, Toiletry, and Fragrance Association, Inc., Washington, D.C, 1982).
  • Suitable 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 acrylamides, alkyl and dialkyl methacrylamides, alkyl acrylate, alkyl methacrylate, vinyl caprolactone, and vinyl pyrrolidone.
  • the alkyl and dialkyl substituted monomers preferably have Ci - C7 alkyl groups, more preferably C ⁇ - 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 quaternization 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 R'X wherein R' is a short chain alkyl, preferably a C1 - C7 alkyl, more preferably a C-
  • Suitable cationic amino and quaternary ammonium monomers include, for example, vinyl compounds substituted with dialkylaminoalkyl acrylate, dialkylaminoalkyl methacrylate, monoalkylaminoalkyl acrylate, monoalkylaminoalkyl methacrylate, trialkyl methacryloxyalkyl ammonium salt, trialkyl acryloxyalkyl ammonium salt, 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.
  • alkyl portions of these monomers are preferably lower alkyls such as the C1 - C3 alkyls, more preferably C-
  • Suitable amine-substituted vinyl monomers for use herein include dialkylaminoalkyl acrylate, dialkylaminoalkyl methacrylate, 13849
  • the cationic polymers hereof can comprise mixtures of monomer units derived from amine- and/or quaternary ammonium-substituted monomer and/or compatible spacer monomers.
  • Suitable cationic hair conditioning polymers include, for example: copolymers of 1-vinyl-2-pyrrolidone and 1-vinyl-3-methylimidazolium salt (e.g., chloride salt) (referred to in the industry by the Cosmetic, Toiletry, and Fragrance Association, "CTFA", as Polyquaternium-16), such as those commercially available from BASF Wyandotte Corp.
  • CTFA Cosmetic, Toiletry, and Fragrance Association
  • cationic polymers that can be used include polysaccharide polymers, such as cationic cellulose derivatives and cationic starch derivatives.
  • Cationic polysaccharide polymer materials 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 1 , R2, and R 3 independently are alkyl, aryl, alkylaryl, arylalkyl, alkoxyalkyl, or alkoxyaryl groups, each group containing up to about 18 carbon atoms, and the total number of carbon atoms for each cationic moiety (i.e., the sum of carbon atoms in R1 , R2 and R 3 ) preferably being about 20 or less
  • X is an anionic counterion, as previously described.
  • Cationic cellulose is available from Amerchol Corp. (Edison, NJ, USA) in their Polymer JR® and LR® series of polymers, as salts of hydroxyethyl cellulose reacted with trimethyl ammonium substituted epoxide, referred to in the industry (CTFA) as Polyquaternium 10.
  • CTFA trimethyl ammonium substituted epoxide
  • Another type of cationic cellulose includes the polymeric quaternary ammonium salts of hydroxyethyl cellulose reacted with lauryl dimethyl ammonium-substituted epoxide, referred to in the industry (CTFA) as Polyquaternium 24. These materials are available from Amerchol Corp. (Edison, NJ, USA) under the tradename Polymer LM-200®.
  • 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).
  • Other materials include quaternary nitrogen-containing cellulose ethers (e.g., as described in U.S. Patent 3,962,418, incorporated herein by reference), and copolymers of etherified cellulose and starch (e.g., as described in U.S. Patent 3,958,581 , incorporated herein by reference.)
  • Silicone Compounds include silicone compounds.
  • the silicone compounds hereof can include volatile soluble or insoluble, or nonvolatile soluble or insoluble silicone conditioning agents.
  • soluble is that the silicone compound is miscible with the carrier of the composition so as to form part of the same phase.
  • insoluble what is meant is that the silicone forms a separate, discontinuous phase from the carrier, such as in the form of an emulsion or a suspension of droplets of the silicone.
  • Suitable silicone fluids include polyalkyl siloxanes, polyaryl siloxanes, polyalkylaryl siloxanes, polyether siloxane copolymers, and mixtures thereof. Other nonvolatile silicone compounds having hair conditioning properties can also be used.
  • silicone compounds herein also include polyalkyl or polyaryl siloxanes with the following structure (I)
  • R is alkyl or aryl
  • 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.
  • the two R groups represent the same group.
  • Suitable R groups include methyl, ethyl, propyl, phenyl, methylphenyl and phenylmethyl.
  • the preferred silicone compounds are polydimethylsiloxane, polydiethylsiloxane, and polymethylphenylsiloxane. Polydimethylsiloxane, which is also known as dimethicone, is especially preferred.
  • the polyalkylsiloxanes that can be used include, for example, polydimethylsiloxanes. These silicone compounds are available, for example, from the General Electric Company in their ViscasilR and SF 96 series, and from Dow Corning in their Dow Corning 200 series.
  • 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. Especially preferred, for enhancing the shine characteristics of hair, are highly arylated silicone compounds, such as highly phenylated polyethyl silicone having refractive index of about 1.46 or higher, especially about 1.52 or higher. When these high refractive index silicone compounds are used, they should be mixed with 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.
  • a spreading agent such as a surfactant or a silicone resin
  • the silicone compounds that can be used include, for example, a polypropylene oxide modified polydimethylsiloxane 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.
  • Other silicone compounds include amino substituted materials. Suitable alkylamino substituted silicone compounds include those represented by the following structure (II)
  • R is CH3 or OH
  • x and y are integers which depend on the molecular weight, the average molecular weight being approximately between 5,000 and 10,000.
  • This polymer is also known as "amodimethicone”.
  • Suitable amino substituted silicone fluids include those represented by the formula (III)
  • R2 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.
  • An especially preferred amino substituted silicone corresponding to formula (III) is the polymer known as "trimethylsilylamodimethicone", of formula (IV):
  • n and m are selected depending on the exact molecular weight of the compound desired.
  • 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 ⁇
  • Q " is a halide 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 silicone compounds 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 silicone compounds.
  • 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 silicone compounds. This overlap is not intended as a limitation on any of these materials. Silicone gums are described by Petrarch, 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 polydimethylsiloxane, polydimethylsiloxane methylvinylsiloxane) copolymer, polydimethylsiloxane diphenylsiloxane methylvinylsiloxane) copolymer and mixtures thereof.
  • silicone resins which are highly crosslinked polymeric siloxane systems.
  • the crosslinking is introduced through the incorporation of tri- functional and tetra-functional silanes with mono-functional or di-functional, 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 methylvinylchlorosilanes, and tetrachlorosilane, with the methyl substituted silanes being most commonly utilized.
  • Preferred resins are offered by General Electric as GE SS4230 and SS4267.
  • 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 silicone compounds 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 TospearfTM 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 mono-functional unit (CH3)3SiO) 5
  • D denotes the difunctional unit (CH3)2SiO
  • T denotes the trifunctional unit (CH3)SiO-
  • Q denotes the quadri- or tetra-functional unit Si ⁇ 2- 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.
  • Nonionic polymers useful herein include cellulose derivatives, hydrophobically modified cellulose derivatives, ethylene oxide polymers, and ethylene oxide/propylene oxide based polymers.
  • Suitable nonionic polymers are cellulose derivatives including methylcellulose with tradename BENECEL, hydroxyethyl cellulose with tradename NATROSOL, hydroxypropyl cellulose with tradename KLUCEL, cetyl hydroxyethyl cellulose with tradename POLYSURF 67, all supplied by Herculus.
  • Other suitable nonionic polymers are ethylene oxide and/or propylene oxide based polymers with tradenames CARBOWAX PEGs, POLYOX WASRs, and UCON FLUIDS, all supplied by Amerchol.
  • the polyalkylene glycol is typically used at a level from about 0.025% to about 1.5%, preferably from about 0.05% to about 1%, and more preferably from about 0.1% to about 0.5% of the compositions.
  • the polyalkylene glycols are characterized by the general formula: H (OCH 2 CH) 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 it is also understood that various positional isomers 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-35 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 known as Polyox WSR® N-3333 available from Union Carbide); and PEG-14 M wherein R equals H and n has an average value of about 14,000 (P
  • compositions of the present invention may include a variety of additional components, which may be selected by the artisan according to the desired characteristics of the final product. Additional components include, for example, polyvalent metal cations, suspending agents, and other additional components.
  • Suitable polyvalent metal cations include divalent and trivalent metals, divalent metals being preferred.
  • Exemplary metal cations include alkaline earth metals, such as magnesium, calcium, zinc, and copper, and trivalent metals such as aluminum and iron. Preferred are calcium and magnesium.
  • the polyvalent metal cation can be added as an inorganic salt, organic salt, or as a hydroxide.
  • the polyvalent metal cation may also be added as a salt with anionic surfactants, as mentioned above.
  • the polyvalent metal cation is introduced as an inorganic salt or organic salt.
  • Inorganic salts include chloride, bromide, iodine, nitrate, or sulfate, more preferably chloride or sulfate.
  • Organic salts include L-glutamate, lactate, malate, succinate, acetate, fumarate, L-glutamic acid hydrochloride, and tartarate.
  • Hardness of the conditioning shampoo compositions can be measured by standard methods in the art, such as by ethylene diamine tetraacetic acid (EDTA) titration. In the event that the composition contains dyes or other color materials that interfere with the ability of EDTA titration to yield a perceptible color change, hardness should be determined fro the composition in the absence of the interfering dye or color.
  • EDTA ethylene diamine tetraacetic acid
  • a preferred additional component is a suspending agent, particularly for compositions comprising silicone compounds of high viscosity and/or large particle size.
  • the suspending agent is in dispersed form in the compositions.
  • 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 such as ethylene glycol stearates, both mono and distearate, long chain amine oxides such as alkyl (C16-C22) dimethyl amine oxides, e.g., stearyl dimethyl amine oxide, and mixtures thereof. When used in the shampoo compositions, these preferred suspending agents are present in the composition in crystalline form. These suspending agents are described in U.S. Patent 4,741 ,855.
  • suspending agents include alkanol amides of fatty acids, preferably having from about 16 to about 22 carbon atoms, more preferably about 16 to 18 carbon atoms, preferred examples of which include stearic monoethanolamide, cocomonoethanolamide, stearic diethanolamide, stearic monoisopropanolamide and stearic monoethanolamide stearate.
  • suspending agents include N,N-dihydrocarbyl amido benzoic acid and soluble salts thereof (e.g., Na and K salts), particularly N,N-di(hydrogenated) C16.
  • soluble salts thereof e.g., Na and K salts
  • N,N-di(hydrogenated) C16 particularly N,N-di(hydrogenated) C16.
  • 8 and tallow amido benzoic acid species of this family which are commercially available from Stepan Company (Northfield,
  • 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 ally! ether of propylene.
  • Neutralizers may be required, for example, amino methyl propanol, triethanol amine, or sodium hydroxide.
  • suspending agents can be used in the compositions, including those that can impart a gel-like viscosity to the composition, such as water soluble or colloidally water soluble polymers like cellulose ethers such as hydroxyethyl cellulose, hydroxymethyl cellulose, hydroxypropyl cellulose, and materials such as guar gum, polyvinyl alcohol, polyvinyl pyrrolidone, hydroxypropyl guar gum, starch and starch derivatives.
  • water soluble or colloidally water soluble polymers like cellulose ethers such as hydroxyethyl cellulose, hydroxymethyl cellulose, hydroxypropyl cellulose, and materials such as guar gum, polyvinyl alcohol, polyvinyl pyrrolidone, hydroxypropyl guar gum, starch and starch derivatives.
  • cellulose ethers such as hydroxyethyl cellulose, hydroxymethyl cellulose, hydroxypropyl cellulose
  • materials such as guar gum, polyvinyl alcohol,
  • a wide variety of other additional ingredients can be formulated into the present compositions. These include: other conditioning agents such as hydrolysed collagen with tradename Peptein 2000 available from Hormel, vitamin E with tradename Emix-d available from Eisai, panthenol available from Roche, panthenyl ethyl ether available from Roche, hydrolysed keratin, proteins, plant extracts, and nutrients; hair-fixative polymers such as amphoteric fixative polymers, cationic fixative polymers, anionic fixative polymers, nonionic fixative polymers, and silicone grafted copolymers; preservatives such as benzyl alcohol, methyl paraben, propyl paraben and imidazolidinyl urea; pH adjusting agents, such as citric acid, sodium citrate, succinic acid, phosphoric acid, sodium hydroxide, sodium carbonate; salts, in general, such as potassium acetate and sodium chloride; coloring agents, such as any of the FD&C or D&C dyes;
  • the hair spray, mousses, lotions and conditioners are suitably made as follows: If included in the formula, polymeric materials are dispersed in water at room temperature. If required, the polymeric materials such as Carbomer and Acrylates/Steareth-20 Methacrylate Copolymer may be neutralized after dispersing. The mixture is then heated up to above 60°C, and fatty alcohols and emulsifiers are added if included in the formulation. After cooling down to below 50°C, the remaining components are added with agitation then cooled down to about 30°C Ethanol is added here if included in the formula. A triblender and mill can be used if necessary to disperse the materials. As appropriate, the mixture thus obtained can be packed into an aerosol can with propellant.
  • the polymeric materials such as Carbomer and Acrylates/Steareth-20 Methacrylate Copolymer may be neutralized after dispersing.
  • the mixture is then heated up to above 60°C, and fatty alcohols and emulsifier
  • the shampoos are suitably prepared by any conventional method well known in the art.
  • a suitable method is as follows: polymer and surfactants are dispersed in water to form a homogeous mixture. To this mixture are added the other ingredients except for silicone emulsion (if present), perfume, and salt; the obtained mixture is agitated. If present, the silicone emulsion is made with Dimethicone or Dimethiconol, a small amount of detersive surfactant, and a portion of water. The obtained mixture is then passed through a heat exchanger to cool, and the silicone emulsion, perfume, and salt are added. The obtained compositions are poured into bottles to make hair shampoo compositions.
  • water and surfactants and any other solids that need to be melted can be mixed together at elevated temperature, e.g., above about 70°C, to speed the mixing into shampoo. Additional ingredients can be added either to this hot premix or after cooling the premix. The ingredients are mixed thoroughly at the elevated temperature and then pumped through a high shear mill and then through a heat exchanger to cool them to ambient temperature. If present in the composition, silicone emulsified at room temperature in concentrated surfactant is added to the cooled mix.
  • Glycerin GLYCERIN USP obtained by Nihon Yushi.
  • Citric Acid ANHYDROUS CITRIC ACID obtained by Haarman & Reimer.
  • Polyquaternium-7 MERQUAT S obtained by Calgon.
  • CARBOPOL 980 obtained by BF Goodrich.
  • Alkyl Trimethyl Ammonium Chloride available from TOHO.
  • optical brighteners e.g., shine, UV protection, color alteration
  • conditioning benefits such as good combing and smoothness

Abstract

L'invention porte sur des compositions de soin pour les cheveux comprenant: (a) une quantité efficace d'un agent optique de brillance; (b) un composé à point de fusion élevé, et (c) un véhiculeur destiné à être appliqué sur les cheveux.
PCT/US1997/016618 1997-09-17 1997-09-17 Compositions de soin pour les cheveux comprenant des agents optiques de brillance et des composes a point de fusion eleve WO1999013849A1 (fr)

Priority Applications (10)

Application Number Priority Date Filing Date Title
PCT/US1997/016618 WO1999013849A1 (fr) 1997-09-17 1997-09-17 Compositions de soin pour les cheveux comprenant des agents optiques de brillance et des composes a point de fusion eleve
AU44864/97A AU4486497A (en) 1997-09-17 1997-09-17 Hair care compositions comprising optical brighteners and high melting point compounds
JP2000511451A JP2001516701A (ja) 1997-09-17 1998-09-04 光学ブライトナーおよびヘアーコンディショニング剤を含んでなるヘアーケア組成物
CN98811097A CN1278717A (zh) 1997-09-17 1998-09-04 包括荧光增白剂和头发调理剂的护发组合物
BR9812818-3A BR9812818A (pt) 1997-09-17 1998-09-04 Composição para tratamento do cabelo e composição de xampu
PCT/IB1998/001381 WO1999013823A2 (fr) 1997-09-17 1998-09-04 Compositions de soins des cheveux, contenant des azurants optiques et des tonifiants capillaires
EP98939798A EP1028697A2 (fr) 1997-09-17 1998-09-04 Compositions de soins des cheveux, contenant des azurants optiques et des tonifiants capillaires
AU88190/98A AU8819098A (en) 1997-09-17 1998-09-04 Hair care compositions comprising optical brighteners and hair conditioning agents
CO98053352A CO4970697A1 (es) 1997-09-17 1998-09-16 Composiciones para el cuidado del pelo que comprenden abri- llantadores opticos y agentes acondicionadores de pelo
PE1998000888A PE116600A1 (es) 1997-09-17 1998-09-17 Composiciones para el cuidado del pelo que comprenden abrillantadores opticos y agentes acondicionadores del pelo

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DE10236063A1 (de) * 2002-08-07 2004-02-19 Beiersdorf Ag Milde Reinigungszubereitung
FR2853231A1 (fr) * 2003-04-01 2004-10-08 Oreal Composition de coloration pour matieres keratiniques humaines comprenant un colorant fluorescent et un agent sequestrant particulier, procede et utilisation
FR2875131A1 (fr) * 2004-09-13 2006-03-17 Oreal Composition comprenant au moins un derive substitue de carbocyanine, procede de traitement des fibres keratiniques la mettant en oeuvre, dispositif et utilisation
US7419511B2 (en) 2004-09-13 2008-09-02 L'oreal, S.A. Compositions comprising at least one substituted carbocyanin derivative, processes for treating keratin fibers using them, device therefor and uses thereof
US7425221B2 (en) 2004-09-13 2008-09-16 L'oreal S.A. Composition comprising at least one substituted derivative of carbocyanine, method for treating keratin fibers using it, device and use
US7427301B2 (en) 2004-09-13 2008-09-23 L'ORéAL S.A. Composition comprising at least one substituted carbocyanin derivative, process for treating keratin fibers using it, device therefor and use thereof

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FR1181860A (fr) * 1956-08-31 1959-06-19 Geigy Ag J R Cosmétiques et leur préparation
US3658985A (en) * 1969-07-28 1972-04-25 Colgate Palmolive Co Oil and fluorescent dye containing luster imparting liquid shampoo
DE2632810A1 (de) * 1976-07-21 1978-01-26 Henkel Kgaa Haarfaerbemittel
EP0717978A2 (fr) * 1994-12-06 1996-06-26 Helene Curtis Inc. Composition de rinçage sous forme d'émulsion eau/huile/eau
EP0754443A2 (fr) * 1995-07-15 1997-01-22 Wella Aktiengesellschaft Composition pour le traitement des cheveux et son procédé de fabrication

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Publication number Priority date Publication date Assignee Title
FR1181860A (fr) * 1956-08-31 1959-06-19 Geigy Ag J R Cosmétiques et leur préparation
US3658985A (en) * 1969-07-28 1972-04-25 Colgate Palmolive Co Oil and fluorescent dye containing luster imparting liquid shampoo
DE2632810A1 (de) * 1976-07-21 1978-01-26 Henkel Kgaa Haarfaerbemittel
EP0717978A2 (fr) * 1994-12-06 1996-06-26 Helene Curtis Inc. Composition de rinçage sous forme d'émulsion eau/huile/eau
EP0754443A2 (fr) * 1995-07-15 1997-01-22 Wella Aktiengesellschaft Composition pour le traitement des cheveux et son procédé de fabrication

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10236063A1 (de) * 2002-08-07 2004-02-19 Beiersdorf Ag Milde Reinigungszubereitung
FR2853231A1 (fr) * 2003-04-01 2004-10-08 Oreal Composition de coloration pour matieres keratiniques humaines comprenant un colorant fluorescent et un agent sequestrant particulier, procede et utilisation
WO2004091556A2 (fr) * 2003-04-01 2004-10-28 L'oreal Composition de coloration pour matieres keratiniques humaines comprenant un colorant fluorescent et agent sequestrant particulier, procede et utilisation
WO2004091556A3 (fr) * 2003-04-01 2005-02-17 Oreal Composition de coloration pour matieres keratiniques humaines comprenant un colorant fluorescent et agent sequestrant particulier, procede et utilisation
FR2875131A1 (fr) * 2004-09-13 2006-03-17 Oreal Composition comprenant au moins un derive substitue de carbocyanine, procede de traitement des fibres keratiniques la mettant en oeuvre, dispositif et utilisation
EP1652553A1 (fr) * 2004-09-13 2006-05-03 L'oreal Composition comprenant au moins un dérivé substitué de carbocyanine, procédé de traitement des fibres kératiniques la mettant en oeuvre, dispositif et utilisation
US7419511B2 (en) 2004-09-13 2008-09-02 L'oreal, S.A. Compositions comprising at least one substituted carbocyanin derivative, processes for treating keratin fibers using them, device therefor and uses thereof
US7425221B2 (en) 2004-09-13 2008-09-16 L'oreal S.A. Composition comprising at least one substituted derivative of carbocyanine, method for treating keratin fibers using it, device and use
US7427301B2 (en) 2004-09-13 2008-09-23 L'ORéAL S.A. Composition comprising at least one substituted carbocyanin derivative, process for treating keratin fibers using it, device therefor and use thereof

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