Europäisches Patentamt *EP001024783B1* (19) European Patent Office Office européen des brevets (11) EP 1 024 783 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.7: A61K 7/48 of the grant of the patent: 12.01.2005 Bulletin 2005/02 (86) International application number: PCT/US1998/021744 (21) Application number: 98953527.3 (87) International publication number: (22) Date of filing: 15.10.1998 WO 1999/020224 (29.04.1999 Gazette 1999/17) (54) EMOLLIENT COMPOSITIONS BASED ON JOJOBA OIL AUFWEICHMITTEL AUF BASIS VON JOJOBA ÖL COMPOSITIONS EMOLLIENTES BASEES SUR L’HUILE DE JOJOBA (84) Designated Contracting States: (56) References cited: AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU IN-A- 172 985 MC NL PT SE • BHATIA ET AL.: "Synthesis of shorter chain (30) Priority: 17.10.1997 US 953132 alcohol esters of jojoba oil" JOURNAL OF THE OIL TECHNOLOGISTS’ ASSOCIATION OF INDIA (43) Date of publication of application: , vol. 26, no. 1, January 1994 (1994-01) - March 09.08.2000 Bulletin 2000/32 1994 (1994-03), pages 23-25, XP002109720 • DATABASE EPODOC [Online] European Patent (73) Proprietor: International Flora Technologies, Ltd. Office, Munich, Germany CN-A-1084056 (ZHOU Gilbert, AZ 85233-2238 (US) ZHIHUI), 23 March 1994 (1994-03-23) XP002109723 (72) Inventor: ARQUETTE, Demetrios, James, G. • DATABASE WPI Week 8644 Derwent Tempe, AZ 85281 (US) Publications Ltd., London, GB; AN 86-287958 XP002109724 & JP 61 210054 A (NONOKAWA (74) Representative: SHOJI YG), 18 September 1986 (1986-09-18) Doble, Richard George Vivian et al • VAN BOVEN ET AL.: "Content and composition Langner Parry of free sterols and free fatty alcohols in jojoba 52-54 High Holborn oil" JOURNAL OF AGRICULTURAL AND FOOD London, WC1V 6RR (GB) CHEMISTRY, vol. 45, no. 4, April 1997 (1997-04), pages 1180-1184, XP000685891 Washington, US. • WENNINGER ET AL.: "International Cosmetic Ingredient Dictionary and Handbook" 1997 , THE COSMETIC, TOILETRY AND FRAGRANCE ASSOCIATION , WASHINGTON, DC, US 7TH ED. VOL 1 XP002109721 page 699 - page 700 Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 1 024 783 B1 Printed by Jouve, 75001 PARIS (FR) EP 1 024 783 B1 Description [0001] This invention relates to emollient compositions for use in cosmetic, personal care and pharmaceutical prep- arations and more particularly to such emollient compositions and processes for their preparation. 5 BACKGROUND OF THE INVENTION: [0002] In the field of cosmetic, personal care, and pharmaceutical products emollients are usually defined as an agent that softens or smooths the skin and which tend to reduce the roughness, cracking and irritation of the skin. The 10 ancient Greek physician, Galen, is thought to have made one of the first emollients consisting of beeswax, spermaceti, almond oil, borax and rosewater. [0003] At the present, there are numerous ingredients which function as emollients in a wide variety of products, and which ingredients may act in subtly different ways. For example, certain emollients sit on the surface of the skin and serve to impede water loss from the skin. Such ingredients generally comprise large molecules that form a hydrophobic 15 barrier to help prevent water from leaving the surface of the skin. Examples of such emollients are silicone derivatives and petroleum jelly. [0004] Other ingredients that have been used as emollients include a number of fatty acids derived from either plant or animal sources. Fatty acids generally comprise aliphatic hydrocarbon or other organic chains with carboxylic sub- stituents on them, typically having between 8 and 24 carbon atoms in the chain backbone. Fatty acids are often used 20 in creams, lotions, shaving creams, lipsticks and as pressing agents in pressed powders and blushes. Fatty acids which are used in cosmetics formulations generally include at least stearic acid, oleic acid, myristic acid and palmitic acid. Other typical fatty acids include linoleic acid, behenic acid, and other common fatty acids of the general formula CnH2n+1COOH. [0005] Fatty alcohols are also used as emollients. They are said to be less sticky and less heavy than many other 25 fatty materials, such as the fatty acids, and are frequently used to improve the viscosity and stability of lotions and creams. They also have utility in reactive hair dying and perming products. Examples of fatty alcohols which find use in the field of cosmetics and personal care products are cetyl alcohol, lauryl alcohol, stearyl alcohol and oleyl alcohol, and others of the general formula CnH2n+1OH. [0006] Additional examples of emollients are fatty esters. One of the best qualities of fatty esters is that they do not 30 feel as oily to the touch as some other types of emollient fatty ingredients. Examples include isopropyl palmitate, isopropyl myristate and glyceryl stearate. [0007] An important emollient is jojoba oil which is derived from the seed of the species Simmondsia chinensis. It is a plant derived oil with excellent skin feel which is composed almost exclusively of wax esters, with little or no triglyc- erides present. A major portion of the production of jojoba oil is used by the cosmetic industry as an emollient in a 35 variety of products. Although jojoba oil has long been used as an emollient, some difficulty has been found in forming stable emulsions using the oil. [0008] The synthesis of esters and waxy esters of natural oils is known, as disclosed in U.S. Patent Nos. 4,031,019 and 4,152,278 (the "Bell" patents), and this technology may be traced back to earlier seminal work done in U.S. Patent No. 1,944,887. In the Bell patents, wax esters are prepared from acids obtained from hydrogenated vegetable oils. 40 Fatty alcohols are esterified with the fatty acids to yield the wax esters which are described as useful for lubricants in replacement of sperm oil. U.S. Patent No. 1,944,887 describes the manufacture of esters from monobasic saturated fatty acids containing 6 to 13 carbon atoms with aliphatic monohydric alcohols containing from 12 to eighteen carbon atoms. [0009] IN-A 172 985 discloses emollients comprising transesterified jojoba oil which is structurally different from the 45 jojoba oil of the present invention. SUMMARY OF THE INVENTION: [0010] The present invention describes a very effective emollient composition for use in personal care, cosmetic and 50 pharmaceutical products and a novel method of producing that composition. The composition can be produced from combinations of fatty alcohols, isopropyl esters and wax esters obtained from the oil contained in the seed of the jojoba plant (Simmondsia chinensis), jojoba oil. [0011] These new emollient compositions preserve the excellent skin feel attributed to jojoba oil, which has long been used as an emollient, and also increase the range of applications for cosmetic compositions by providing an 55 emollient that can provide a more polar and hydrophilic quality than is found in jojoba oils, (which may also be referred to in the art as jojoba wax esters). The composition forms stable emulsions much more readily than does jojoba oil. The composition may also further provide excellent emolliency to normally dry cosmetic systems involving high levels of pigments, with the emollient acting as a pigment wetting agent. It also functions as an excipient in pressed powder. 2 EP 1 024 783 B1 [0012] The compositions comprising fatty alcohols, isopropyl esters and jojoba wax esters (jojoba oil) may be ob- tained by the base catalyzed alcoholysis reaction between jojoba oil and isopropyl alcohol. [0013] The fatty alcohol components of jojoba oil include a mixture of ingredients, but the largest segment of the oil comprises the fatty alcohols of the following general formula: 5 CH3 - (CH2)7 - CH = CH - CH2 - (CH2)x - CH2 - OH wherein X= 6, 8 , 10 or 12. The preferred fatty alcohols comprise those where X= 8, 10 and/or 12. 10 [0014] Such fatty alcohols useful in the invention can be described as monounsaturated, straight chain, primary fatty alcohols (e.g., of 18 to 24 carbon atoms). A single double bond is located towards the middle of the respective fatty alcohol chain, specifically in the n-9 position (i.e., counted from the terminal (-CH3) group). The preferred fatty alcohols are composed of even numbers of carbon atoms, specifically, 20 and 22 carbon atoms. The typical composition of the fatty alcohols used in this invention as determined by gas chromatography (GC) is: 15 FATTY ALCOHOLS X (No. of carbon: No. of double Typical % (area by GC) bonds) 20 6 18:1 1 8 20:1 52 10 22:1 38 12 24:1 6 other fatty alcohols 3 25 Total 100 The isopropyl esters derived from jojoba oils according to a practice of this invention may have the following general formula: 30 35 wherein X= 6, 8, 10 and/or 12, preferably 8, 10 and/or 12. [0015] Thus, the isopropyl esters useful in this invention are composed of monounsaturated, straight-chain fatty acids combined with isopropyl alcohol. The double bond is located in the middle of the respective fatty acid, specifically 40 in the n-9 position. The fatty acids are all of even number of carbon atoms, primarily 20 and 22 carbons. The typical composition of the isopropyl esters found in this invention as determined by gas chromatography is: X Fatty Acid Component of Isopropyl Ester (No. of carbon atoms: No.