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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 HAR 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-Alkyl)-D-gluconamide and the 75 Inventor: Robert Wermeer, Nutley, N.J. 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. Cl. ................ A61K7/07; A61K7/075 Crystals, 1986, vol. 1, vol. 1, No. 4, 357-370. 52 U.S. Cl. ........................................ 424/70.24; 424/70.1 Amphiphilic Properties of Synthetic Glycolipids Based in (58) Field of Search ........................... 424/70.1, 70.13, Amide Linkages, Makromol, Chem. 189, 2433-2442 424/70.17, 70.24 (1988). Molecular and Crystal Structures of N-(n-Heptyl)-and 56 References Cited N-(n-Decyl)-D-Glyconamide, Fahrnow et al., Carbohy U.S. PATENT DOCUMENTS drate Research 176 (1988) 165-174). 2,662,073 12/1953 Mehltretter et al. ................... 536/7.2 Supramolecular Assemblies of Diacetylenic Aldonamids, 2,72121 10/1955 Buc .................... ... 260/S62 Frankel et al., J. Am. Chem. Soc., 1991, 113,7436-7437. 2,752,334 6/1956 Walton ....... ... 260/21 A New Class of Model Glycolipids; Synthesis, Character 2,776,951 1/1957 Melamed ... ... 536/17.2 ization, and Interaction with Lectins, Williams et al., 2,785,152 3/1957 Jones ...... ... 260/112 Archives of Biochemistry and Biophysics, vol. 195, No. 1, 3,766,267 10/1973 Zak ........ ... 260/561 B 3,855.290 12/1974 Zak et al.... ... 260/561 B Jun., pp. 145-151, 1979. 3,990,991 1/1976 Gerstein .................................. 252/542 Synthesis of a New Class of Model Glycolipids, Williams et 4,038294 7/1977 Conner et al. .. 260/SO1.5 ai. -Carbohydrate Research, 67 (1978) C1-C3. 4,190,429 2/1980 Rutter et al. ................................ 71/67 Technical Notes, Scholnicket al., pp. 471-473. 4,342,706 8/1982 Conner et al. ....................... 260/404.5 4,529,588 7/1985 Smith et al. ........ ... 260/561 B Compositions Comprising Nonionic Glycolipid Surfactants, 4,534,964 8/1985 Herstein et al. .......................... 424/70 Filed as U.S. Ser. No. 816,419. 4,618,675 10/1986 Lichtenthalier ..... 536/72 Light Scattering from Nonionic Surfactants of the Sugar 4,973,473 1/1990 Schneider et al. .......................... 424/6 Lipid Hybrid Type in Aqueous Solution, Denkinger et al., J. 5,037,973 8/1991 Meinetsberger ... 260/102 Phys. Chem., 1989, 93, pp. 1428-1434. 5,084.270 1/1992 Ciaudelli................................... 424/59 Investigations of a Series of Nonionic Surfactants of Sugar FOREIGN PATENT DOCUMENTS Lipid Hybrids by Light Scattering and Electron Microscopy, 2523962 9/1983 France. Denkinger et al., Colloid & Polymer Science 268:513 527 2321752 11/1974 Germany. (1990). 2338087 1/1975 Germany. Monolayers 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 OTHER PUBLICATIONS from Lactose, Ghoul, Journal of Fluoride Chemistry, 59 (1992) 107-112. W Synthetic Emulsifying 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. 3309 (1963), pp.182-188 (English Translation). al., J. Chem. Soc., Perkin Trans 2, 1994pp. 1023-1028. Reaction of Aliphatic Diamines with D-Gluconic Acid 8-Lactone, Geyer, vol. 97 (1964), pp. 2271-2275 (English Primary Examiner-Salle M. Gardner Translation). Attorney, Agent, or Firm-Ronald A. Koatz Amphiphilic Properties of Synthetic Glycolipids Based on Amide Linkages, L. 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. Lipid Bilayer Fibers from Diastereomeric and Enantiomeric found that when these heteroatom containing alkyl aldona N-Octylaldonamides, Fuhrhop et al., J. Am. Chem. Soc., mides are used, benefits such as enhanced stability and/or 1988, 110, pp. 2861-2867. enhanced viscosity are obtained relative to the use of other Stereochemistry and Curvature Effects in Supramolecular known thickeners or non-heteroatom containing aldona Organization and Separation Process of Micellar N-Alky mides. laldonamide Mixtures, Fuhrhop et al., J. Am. Chem. Soc., 1990, 112, pp. 1768-1775. 1 Claim, No Drawings 5,641,480 1. 2 HAR CARE COMPOSITIONS COMPRSING Viscosity/Clarity HETEROATOM CONTAINING ALKYL The viscosity or thickness 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, specifically heteroatom turbid or produce sedimentation upon standing. Ideal hair containing alkyl aldonamide compounds. 10 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 thickliquid 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 lackheteroatoms 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 20 Background Art Alkyl Aldonamides initating the eyes and scalp. Hair soil includes natural skin An aldonamide is defined 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 defined as ronment and residue from hair-grooming products applied a sugar substance in which the pseudoaldehyde orpseudoke by the consumer. After accomplishing the cleansing action, tose group, generally found at the C or C. 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 aidonolactone. 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, gluconamides or and it is not surprising to find that considerable resource and glucoheptonamides), two saccharide units (e.g., effort have been directed towards the discovery and devel 30 lactobionamides, maltobionamides, meibionarnides, opment of new ingredients that provide improved foam, cellobionamides, gentiobionamides or D-glucopyranosyl viscosity, clarity and conditioning characteristics. The patent (1-5)-D-arabinomamides) or they may be based on com literature, cosmetic journals and formularies describe many pounds comprising more than two saccharide units. Any such ingredients, however, they still do not provide all the carbohydrate can be used as long as the sugar has a answers to the problems encountered in making a totally 35 pseudoaldehyde or pseudoketose group available for oxida satisfactory product. 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 modifiers or conditioning agents in hair care com These findings are quite unexpected and have not been positions. recognized or appreciated in the art. In particular,
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