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United States Patent [19] [11] Patent Number: 5,641,480 Vermeer [45] Date of Patent: Jun

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United States Patent [19] [11] Patent Number: 5,641,480 Vermeer [45] Date of Patent: Jun US005641480A United States Patent [19] [11] Patent Number: 5,641,480 Vermeer [45] Date of Patent: Jun. 24, 1997 [54] HAIR CARE COMPOSITIONS COMPRISING A New Family of Liquid Crystals: N-Substituted Aldona HETEROATOM CONTAINING ALKYL mides, Mol. Cryst. Liq. Cryst. 1986, vol. 135, pp. 93-110. ALDONAMIDE COMPOUNDS Molecular Packing and Hydrogen Bonding in the Crystal Structures of the N-(n-AlkyD-D-gluconarnide and the [75] Inventor: Robert Vermeer, Nutley, NJ. 1-Deoxy-(N-methyl-alkanamido)-D-glucitol Mesogens, Mol. Cryst. Liq. Cryst. 1990, vol. 185, PP - 209-213. [73] Assignee: Lever Brothers Company, Division of Conopco, Inc., New York, N.Y. Molecular Crystals and Liquid Crystals, vol. 198 (1991). Amphiphilic Properties of Synthetic Glycolipids Based on Amide Linkages, Zabel et al., Chemistry and Physics of [21] Appl. No.: 352,309 Lipids, 39 (1986) 313-327. [22] Filed: Dec. 8, 1994 Liquid-crystalline Behaviour in the N-alkyl Gluconamides and Other Related Carbohydrates, Pfanhemuller, Liquid [51] Int. (:1.6 ............................ .. A61K 7/07; A61K 7/075 Crystals, 1986, vol. 1, vol. 1, No. 4, 357-370. [52] US. Cl. ...................................... .. 424/7024; 424/701 Amphiphilic Properties of Synthetic Glycolipids Based in [58] Field of Search .............................. .. 424/701, 70.13, Amide Linkages, Makromol, Chem. 189, 2433-2442 424/7017, 70.24 (1988). [56] References Cited Molecular and Crystal Structures of N-(n-Heptyl)-and N-(n-DeCyD-D-GlycOnamide. Fahrnow et al., Carbohy U.S. PATENT DOCUMENTS drate Research 176 (1988) 165-174). 2,662,073 12/1953 Mehltretter et a1. ................. .. 536/172 Supramolecular Assemblies of Diacetylenic Aldonarnids, 2,721,211 10/1955 Frankel et al., J. Am. Chem. Soc., 1991, 113, 7436-7437. 2,752,334 6/1956 A New Class of Model Glycolipids; Synthesis, Character 2,776,951 1/1957 ization, and Interaction with Lectins, Williams et al., 2,785,152 3/1957 Archives of Biochemistry and Biophysics, vol. 195, No. 1, 3,766,267 l0/1973 Jun., pp. 145-151, 1979. 3,855,290 12/1974 3,990,991 11/1976 Synthesis of a New Class of Model Glycolipids, Williams et 4,038,294 7/1977 a1. —Carbohydrate Research, 67 (1978) C1-C3. 4,190,429 2/1980 Technical Notes, Scholnick et al, pp. 471-473. 4,342,706 8/1982 4,529,588 7/l985 Compositions Comprising Nonionic Glycolipid Surfactants, 4,534,964 8/1985 Filed as US. Ser. No. 816,419. 4,618,675 10/1986 Light Scattering from Nonionic Surfactants of the Sugar 4,973,473 ll/1990 Lipid Hybrid Type in Aqueous Solution, Denkinger et al., J. 5,037,973 8/1991 Phys. Chem, 1989, 93, PP. 1428-1434. 5,084,270 l/1992 Investigations of a Series of Nonionic Surfactants of Sugar FOREIGN PATENT DOCUMENTS Lipid Hybrids by Light Scattering and Electron Microscopy, Denldnger et al., Colloid & Polymer Science 268:513 527 2523962 9/1983 France . 2321752 1111974 Gennany . (1990). 2338087 l/1975 Germany . Mouolayers from Synthetic Glycolipids, Emmerling, Poly 62-327860 7/1989 Japan . mer Bulletin 6, 305-308 (1982). 94/12511 6/1994 WIPO . Synthesis of New Fluorinated Nonionic Surfactants Derived UT HER PUBLICATIONS from Lactose, Ghoul, Journal of Fluoride Chemistry, 59 (1992) 107-112. ~ Synthetic Ernulsifying Agents, Fieser et al., Jun. 20, 1956, Conformational Effects of 1,3-syn-Diaxial Repulsion and vol. 78, pp. 2825-2832. 1,2-gauche Attraction Between Hydroxy Groups in Mono Linking Sugars with Amino Acid Esters of Lipophilic Alco molecular N-Octyl-D-Hexonamide Solutions, Svenson et hols to Form Surface-Active Sugar Derivatives, Geyer, vol. al., J. Chem. Soc., Perkin Trans 2, 1994,pp. 1023-1028. 330 9 (1963), pp.182-188 (English Translation). Reaction of Aliphatic Diamines with D-Gluconic Acid 8-Lactone, Geyer, vol. 97 (1964), pp. 2271-2275 (English Primary Examiner-Sane M. Gardner Translation). Attorney, Agent, or Firm-—R0nald A. Koatz Amphiphilic Properties of Synthetic Glycolipids Based on Amide Linkages, 1. Electron Microscopic Studies on Aque [57] ABSTRACT ous Gels, Chem. & Physics of Lipids 37 (1985) 227-240. The invention relates to hair care compositions containing The Chiral Bilayer Effect Stabilizes Micellar Fibers, heteroatom containing alkyl aldonamide compounds and Fuhrhop et al., J.Am. Chem. Soc., vol. 109, No. 11; pp. hair conditioning agents. Unexpectedly, applicants have 3386-3390 & Supplemental Material. found that when these heteroatom containing alkyl aldona Lipid Bilayer Fibers from Diastereomeric and Enantiomeric N-Octylaldonamides, Fuhrhop et al., I. Am. Chem. Soc., mides are used, bene?ts such as enhanced stability and/or 1988, 110, pp. 2861-2867. enhanced viscosity are obtained relative to the use of other Stereochemistry and Curvature E?’ects in Supramolecular known thickeners or non-heteroatom containing aldona Organization and Separation Process of Mieellar N-Alky mides. laldonamide Mixtures, Fuhrhop et al., I. Am. Chem. Soc., 1990, 112, pp. 1768-1775. 1 Claim, No Drawings 5,641,480 1 2 HAIR CARE COMPOSITIONS COMPRISING Viscosity/Clarity HETEROATOM CONTAINING ALKYL The viscosity or thiclmess of a hair care composition also ALDONAMIDE COMPOUNDS plays an important role in the selection of that product, since consumers are accustomed to, and expect hair care compo TECHNICAL FIELD sitions to be thick and viscous. If a hair care composition is The present invention is related to new hair care compo thin and nonviscous, a consumer may conclude that the sitions that have improved foam, viscosity, clarity and product is inferior. Furthermore, successful hair care com conditioning characteristics due to the inclusion of a new positions must have good shelf life and should not become type of alkyl aldonamide compound. speci?cally heteroatom turbid or produce sedimentation upon standing. Ideal hair containing alkyl aldonamide compounds. care compositions should cleanse the hair gently and should not overdry the scalp. Surprising the hair care compositions BACKGROUND OF THE INVENTION of the present invention that comprise a heteroatom con The hair of the head has been associated with beauty and taining alkyl aldonamide compound produce clear, stable, social distinction. For this reason, a special importance is thick liquid compositions with good conditioning properties. attached in the cosmetic area to hair care products such as 15 This is unusual and unexpected, since alkyl aldonamides rinses, conditioners, shampoos, conditioning shampoos and that lack heteroatoms generally form opaque, nontransparent the like. liquid compositions which are instead useful as opacifying The primary function of a hair care composition is to or pearlescent agents. cleanse the hair and scalp from soil without stinging or Background Art Alkyl Aldonamides irritating the eyes and scalp. Hair soil includes natural skin An aldonamide is de?ned as the amide of an aldonic acid secretions (such as sebum), skin debris, dirt from the envi (or aldonolactone) and an aldonic acid, in turn is de?ned as ronment and residue from hair-grooming products applied a sugar substance in which the pseudoaldehyde or pseudoke by the consumer. After accomplishing the cleansing action, tose group, generally found at the C1 or C2 position on the the shampoo should not excessively remove the natural oil 25 sugar, has been oxidized to a carboxylic acid group which from the scalp and should leave the hair soft, lustrous and upon drying cyclizes to an aldonolactone. manageable while simultaneously providing a rich copious Aldonamides may be based on compounds comprising foam or lather. This has become a difficult challenge to meet one saccharide unit (e.g., ribonamides, gluconarnides or and it is not surprising to ?nd that considerable resource and glucoheptonamides), two saccharide units (e.g., effort have been directed towards the discovery and devel opment of new ingredients that provide improved foam, lactobionamides, maltobionamides, melibionarnides, viscosity, clarity and conditioning characteristics. The patent cellobionamides, gentiobionamides or D-glucopyranosyl literature, cosmetic journals and forrnularies describe many (1-5)-D-arabinonamides) or they may be based on com such ingredients, however, they still do not provide all the pounds comprising more than two saccharide units. Any answers to the problems encountered in making a totally carbohydrate can be used as long as the sugar has a satisfactory product. 35 pseudoaldehyde or pseudoketose group available for oxida tion to a carboxylic acid group. It has now been found that the inclusion of a heteroatom While alkyl aldonamides are known in the art, there is no containing alkyl aldonamide compound in a hair care com teaching or suggestion of using heteroatom containing alkyl position of the invention, surprisingly provides improved aldonamide compounds of the invention as foam stabilizers, foam, viscosity, clarity and conditioning characteristics. viscosity modi?ers or conditioning agents in hair care com These ?ndings are quite unexpected and have not been positions. recognized or appreciated in the art. In particular, there is no teaching that using heteroatom The hair care compositions of the present invention may containing alkyl aldonamide compounds in hair care com be in aerosol, liquid, gel, creme (cream), lotion, paste, positions alone or with, for example, anionic surfactants granular, powdered, tablet or bar form. Included among the 45 (e.g., sodium or ammonium salts of alkyl sulfates, alkyl hair care compositions are rinses, conditioners, shampoos, ether sulfates), nonionic surfactants (e.g., alkyl polyoxy conditioning shampoos, antidandruif shampoos and the like. alkylene sorbitau esters or alkyl polyglycosides), amphoteric However, the conditioners, shampoos, conditioning sham surfactants (e.g., alkyl carboxybetaines) and mixtures poos and antidandruff shampoos are the preferred compo thereof, could result in a clear thickened hair care compo sitions. sition that foams copiously and leaves the hair soft, lustrous Foam and manageable. US. Pat. No. 2,662,073 to Mehltretter, et al. for example, The ability of a hair care composition to create a desirable teaches gluconamide compounds of the formula: rich lather is a signi?cant driving force in the selection of that product.
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