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(12) United States Patent (10) Patent No.: US 9,168,397 B2 Amalric Et Al

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(12) United States Patent (10) Patent No.: US 9,168,397 B2 Amalric Et Al US009 168397B2 (12) United States Patent (10) Patent No.: US 9,168,397 B2 Amalric et al. (45) Date of Patent: Oct. 27, 2015 (54) POWDERY EMULSIFYING COMPOSITION A61Q 19/005; A61Q 1/02: A61K 8/92: OF ALKYL POLYGLYCOSIDES, USE A61K 8/34: A61K 8/602: A61K 8/022: THEREOF FOR PREPARING COSMETC A61K 8/60; A61K 8/062: A61K 8/604; EMULSIONS, AND METHOD FOR A61K 8/06; A61K 8/342: A61K 2800/412: PREPARING SAME BO1F17/0092 See application file for complete search history. (71) Applicant: SOCIETE DEXPLOITATION DE PRODUITS POUR LES INDUSTRIES CHIMIQUES SEPPIC, (56) References Cited Paris (FR) U.S. PATENT DOCUMENTS (72) Inventors: Chantal Amalric, Blan (FR); Alicia Roso, Saix (FR); Agnes Gorce, 5,670471 A 9, 1997 Amalric et al. 5,888,482 A 3, 1999 Amalric et al. Marseille (FR) 5,958,431 A 9/1999 Brancq et al. 6,245,821 B1 6/2001 Bulcourt et al. (73) Assignee: SOCIETE DEXPLOITATION DE 6,268.400 B1 7/2001 Amalric et al. PRODUITS POUR LES 6,353,034 B1 3/2002 Amalric et al. INDUSTRIES CHIMIQUES SEPPIC, 6,488,946 B1 12/2002 Milius et al. Paris (FR) 6,723,774 B2 4/2004 Guntherberg et al. 2003/0105169 A1 6/2003 Lennon (*) Notice: Subject to any disclaimer, the term of this patent is extended or adjusted under 35 FOREIGN PATENT DOCUMENTS U.S.C. 154(b) by 0 days. EP O992508 4/2000 FR 2756195 5, 1998 (21) Appl. No.: 14/278,908 FR 2784904 4/2000 FR 283O464 4/2003 (22) Filed: May 15, 2014 WO 92O6778 4f1992 WO 9513863 5, 1995 (65) Prior Publication Data WO 9637285 11 1996 WO 9637286 11, 1996 US 2014/O2554.57 A1 Sep. 11, 2014 WO 971.8033 5, 1997 Related U.S. Application Data (Continued) (62) Division of application No. 13/201,131, filed as OTHER PUBLICATIONS application No. PCT/FR2010/050250 on Feb. 15, 2010, now Pat. No. 8,821,902. Seppic, COSM'ethics, Mar. 2008, Seppic, pp. 1-33. (Continued) (51) Int. Cl. A61O 19/00 (2006.01) A6 IK 8/92 (2006.01) A6 IK 8/34 (2006.01) Primary Examiner — Trevor Love A6 IK 8/60 (2006.01) (74) Attorney, Agent, or Firm — Young & Thompson A6 IK 8/02 (2006.01) BOIF I7/00 (2006.01) A61O I/14 (2006.01) (57) ABSTRACT A6 IK 8/06 (2006.01) A61O 19/04 (2006.01) A powdery composition C1 contains for 100% of the mass: 5 A61O 1704 (2006.01) to 70 mass % and more particularly 10 to 50 mass % of at least A61O I/02 (2006.01) one compound of formula (I): R-O-(G),-H, wherein R is a (52) U.S. Cl. linear Saturated aliphatic radical including 12 to 22 carbon CPC .............. A61O 19/008 (2013.01); A61 K8/022 atoms, G is the remainder of a reducing Sugar selected from (2013.01); A61 K8/06 (2013.01); A61 K8/062 the group including glucose, Xylose and arabinose, and X is a (2013.01); A61K 8/34 (2013.01); A61K 8/342 decimal number greater than or equal to 1 and lower than or (2013.01); A61K 8/60 (2013.01); A61K 8/602 equal to 10; 95 to 30 mass % and more particularly 90 to 50 (2013.01); A61K 8/604 (2013.01); A61K 8/92 mass % of one or more alcohols of formula (II): R' OH, (2013.01); A61O 1/14 (2013.01); A61O 1704 wherein R' is a linear saturated aliphatic radical including 12 (2013.01); A61O 19/00 (2013.01); A61O to 22 carbonatoms identical to or different from Ras defined 19/007 (2013.01); A61O 19/04 (2013.01); in formula (I), wherein at least 90 vol% of the particles have BOIF 17/0092 (2013.01); A61K 2800/412 a diameter lower than or equal to 250 micrometers, more (2013.01); A61O 1/02 (2013.01); A61 O 19/005 particularly a diameter lower than or equal to 150 microme (2013.01) ters. (58) Field of Classification Search CPC ..... A61Q 19/008: A61Q 19/007; A61Q 1/14: A61Q 19/04; A61Q 19/00; A61Q 17/04; 5 Claims, No Drawings US 9,168.397 B2 Page 2 (56) References Cited PharmaNews, A Fresh Shot of Inspiration, 2008. Alsiano, No. 8, pp. 1-10. Snezana Savic et al., “Colloidal microstructure ofbinary systems and FOREIGN PATENT DOCUMENTS model creams stabilized with an alkylpolyglucoside non-ionic emul WO 98.47610 10, 1998 sifier”. Colloid & Polymer Science; Kolloid-Zeitschrift and WO 0056438 9, 2000 Zeitschrift fur Polymere, Springer, Berlin, DE, vol. 283, No. 4, Jan. 1, 2005, pp. 439-451, XPO1934.0382, ISSN: 1435-1536. OTHER PUBLICATIONS International Search Report, dated Jun. 4, 2010, from corresponding PCT application. Machine Translation of EPO992508, WIPO, last accessed Sep. 20, French Search Report, dated Oct. 14, 2009, from corresponding 2013. French application. US 9, 168,397 B2 1. 2 POWDERY EMULSIFYING COMPOSITION final emulsion. For this, branched or unsaturated fatty alco OF ALKYL POLYGLYCOSIDES, USE hols have been used to produce such mixtures. Such liquid THEREOF FOR PREPARING COSMETC emulsifiers are described in the international application pub EMULSIONS, AND METHOD FOR lished under number WO 00/56438 or else in the French PREPARING SAME patent application published under number FR 2830 464. Such liquid compositions, owing to their very lipophilic The invention relates to the provision of novel emulsifying nature, do not make it possible to prepare oil-in-water emul compositions that can be used in the preparation of cosmetic sions which are sufficiently stable and/or which have sensory and/or pharmaceutical formulations in particular for topical properties that are sufficiently satisfactory for the final client. SC. 10 In the context of their research on the constant improve Sugar-derived emulsifiers have been developed for more ment of emulsifiers for preparing “oil-in-water emulsions than about twenty years and their commercial Success which do not have the abovementioned drawbacks, the inven requires no further demonstration. They consist of a mixture tors have developed novel emulsifying compositions, and of alkyl polyglycosides and/or alkenyl polyglycosides and of also a novel method for preparing oil-in-water emulsions, fatty alcohols, and are available on the market in solid form, 15 which make it possible to prepare emulsions that are stable in whether as flakes, powder or beads. Such emulsifiers are the presence of thermosensitive and/or Volatile ingredients, described in the international applications published under without the appearance of phase inversion phenomena during numbers WO92/06778, WO95/13.863, WO 96/37285. WO their preparation, and which provide said emulsions with 98/47610 or FR 2784904. They make it possible to prepare advantageous sensory properties, such as a rich and creamy stable emulsions in oil-in-water or water-in-oil form. The feel. presence of an amount of fatty alcohols of greater than 30% According to a first aspect, the Subject of the invention is a by weight for 100% of the weight of these compositions pulverulent composition C1 comprising, for 100% of its creates a consistency and sensory properties which are advan weight: tageous, for instance a rich and creamy feel of the final emul from 5% by weight to 70% by weight, more particularly S1O. 25 Patent application FR 2 756 195 discloses emulsifying from 10% by weight to 50% by weight, of at least one compositions intended for the preparation of emulsions with compound of formula (I): improved Stability, and particularly intended for preparing stable fluid emulsions. These compositions comprise: i) from 30% to 90% by weight of a mixture of at least one 30 in which the R radical represents a saturated linear aliphatic alkyl polyglycoside of which the linear or branched, saturated radical containing from 12 to 22 carbon atoms, G represents or unsaturated alkyl radical contains from 8 to 22 carbon the residue of a reducing Sugar selected from the group con atoms and at least one alkyl polyglycoside of which the alkyl sisting of glucose, Xylose and arabinose, and X represents a radical is an oleyl radical or an isostearyl radical, and decimal number greater than or equal to 1 and less than or ii) from 10% to 70% by weight of at least one fatty alcohol 35 equal to 10; of which the linear or branched, saturated or unsaturated alkyl from 95% by weight to 30% by weight, more particularly radicals contain from 8 to 22 carbon atoms. from 90% by weight to 50% by weight, of one or more Application EP 0992 508 discloses emulsifying composi alcohols of formula (II): tions intended for improving the whiteness of the emulsions prepared, and which comprise: 40 R" OH (II) i) from 5% to 60% by weight of a mixture of alkyl polyg in which the R' radical, which may be identical to or different lycosides comprising, for 100% of its weight: than the R radical as defined above, represents a saturated from 30% to 95% by weight of a mixture of cetyl polyg linear aliphatic radical containing from 12 to 22 carbon lycosides and Stearyl polyglycosides, atoms, and in which at least 90% by volume of the particles from 70% to 5% by weight of a mixture of arachidyl 45 have a diameter of less than or equal to 250 micrometers, and polyglycosides and behenyl polyglycosides; more particularly a diameter of less than or equal to 150 ii) from 95% to 40% by weight of one or more fatty alco micrometers. hols of which the linear or branched, saturated or unsaturated The expression “saturated linear aliphatic radical contain alkyl radicals contain from 14 to 22 carbon atoms.
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