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(19) United States (12) Patent Application Publication (10) Pub US 20070286828A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2007/0286828 A1 Deswartvaegher et al. (43) Pub. Date: Dec. 13, 2007 (54) VARNISH COMPOSITION BASED ON A (22) Filed: May 23, 2007 SOLVENT EXCLUSIVELY OF VEGETABLE ORIGIN Related US. Application Data (75) Inventors: Alain Deswartvaegher, Bergerac (FR); (63) Continuation of application No. PCT/EP05/56098, Bernard Forestier, Saint Nexans (FR); ?led on Nov. 21, 2005. Sophie Miard, Saint Germain Et Mons (FR); Jean-Pierre Senet, Buthiers (FR); (30) Foreign Application Priority Data Sophie Thiebaud-Roux, L’Union (FR); Daniela Cristea, Toulouse (FR); Nov. 23, 2004 (FR) ............................................ .. 0412409 Pascale De Caro, Toulouse (FR); Geraldine Giacinti, Fonsorbes (FR); Publication Classi?cation Mathieu Bandres, Toulouse (FR) (51) Int. Cl. Correspondence Address: A61K 8/34 (2006.01) HARNESS, DICKEY & PIERCE, P.L.C. A61K 8/37 (2006.01) P.O. BOX 828 (52) US. Cl. .............................................................. .. 424/61 BLOOMFIELD HILLS, MI 48303 (US) (57) ABSTRACT (73) Assignee: Durlin France, Bergerac (FR) A varnish composition for cosmetic or pharmaceutical use, (21) Appl. No.: 11/805,553 comprising at least one solvent of plant origin. US 2007/0286828 A1 Dec. 13, 2007 VARNISH COMPOSITION BASED ON A SOLVENT [0006] The emissions of each solvent present in a varnish EXCLUSIVELY OF VEGETABLE ORIGIN composition are calculated by the equation: CROSS-REFERENCE TO RELATED APPLICATIONS [0001] This application is a continuation of PCT/EP2005/ 056098, ?led Nov. 21, 2005, Which claims priority to French Application No. 04/ 12409, ?led Nov. 23, 2004. Both of Where: these applications are incorporated by reference herein. Ei is the emission of the species i in kg per year, Mi is the molecular mass of the species i in g/mol, BACKGROUND AND SUMMARY Ki is the mass transfer coe?icient of the species i in m~s_l, [0002] The present invention relates to a varnish compo from the liquid phase to the gas phase, sition for cosmetic or pharmaceutical use, produced using solvents of natural origin. These solvents are acetates, car Pi is the vapour pressure of the species i in kPa, bonates or ethers prepared from the same natural molecule Hr is the duration in hours of the manufacturing operation, and have a vapour tension that is less than ethyl, propyl or A is the free surface area of the tank in m2, butyl acetates. This property induces a lesser emission of volatile organic compounds (V OCs). R is the ideal gas constant (8.314 J~K_l~mol_l), [0003] A ministerial order dated 1 Mar. 1993 considers T is the absolute temperature in Kelvin, and any compound Which, With the exclusion of methane, con N is the number of identical manufacturing operations in the tains carbon and hydrogen (Which may be substituted With year. other atoms such as halogens, oxygen, sulphur, nitrogen or phosphorus, With the exception of carbon oxides and of The coef?cient of transfer of the species i to the gas phase (Ki) can be determined by the equation: carbonates), and Which is in the gaseous or vapour state under normal temperature and pressure conditions, to be a volatile organic compound (VOC). European Directive is 1/3 1999/ 13/EC completes this de?nition and adds that any Ki: 0.00250- V078 Ml organic product having a vapour pressure of greater than 10 Pa (approximately 0.075 mmHg) is considered to be a VOC. In the United States, the vapour tension threshold selected is Where: much loWer, namely 0.13 Pa (approximately 0.001 mmHg) under normal conditions. In Australia, VOCs are de?ned as Ki is expressed in m~s_l, chemical compounds having a vapour pressure of greater V is the speed of the air above the tank in ms“, than 27 Pa at 250 C. [0007] Mi is the molar mass of the species i in g~mol_l. [0004] Among VOCs, mention may in particular be made, without this list being exhaustive, of solvents, degreasing TABLE 1 agents, dissolving agents, preserving agents, cleaning agents Comparison between the vapour tensions and the ?ashpoints of and dispersing agents. The legislations, although variable the usual solvents for nail varnish (ethyl and butyl acetate) according to country, all tend toWards a reduction in the and of the solvents of natural origin emission of these VOCs. In France, the regulations have Vapour tension at 25° C. been modi?ed in order to take into account the requirements (Pa) Flashpoint (0 C.) derived from European Directive 1999/ 13/EC of 11 Mar. 1999 relating to the reduction of VOC emissions due to the Ethyl acetate 10300 —4 Butyl acetate 1990 24 use of organic solvents in certain activities and installations. Ethanol 7827 12.8 Consequently, it is essential to ?nd cosmetic compositions Isoarnyl acetate 757 25 Which have limited VOC levels. Isoarnyl alcohol 555 45.6 Isoarnyl carbonate 374 55.5 [0005] The molecules presented in Table 1 have a vapour Ethyl isoalnyl ether 3413 9 tension that is substantially loWer than the vapour tensions Methyl isovalerate 2426 19.4 Ethyl isovalerate 1047 26.7 of the solvents normally used in nail varnishes, ethyl acetate and butyl acetate. In order to clearly and vigorously evaluate the reduction in VOC emission brought about by the use of The term “fusel oil”, of German origin, translates as “loWer novel solvents of natural origin, the study Was based on a alcohol or alcohol of poor quality”. Today, this term denotes model published in 2002 by the ADEME [French Environ all higher alcohols obtained at various stages of fermenta mental and Energy Control Agency) in the report titled tion. The compounds of fusel oil can be classi?ed in tWo “VOC emissions in the paint, varnish, printing ink, glue and major groups (PATIL A. G. S. M. et al. International Sugar adhesive production sector”. The model used, the Clements model, makes it possible to calculate the VOC emissions Journal, (2002), 104, 51-54, 56-58): engendered by surface evaporation during the production of [0008] the high boiling fraction (HBF), Bp >132o C. It a varnish in an open tank. represents only 1 to 5% of fusel oil. The constituents of this US 2007/0286828 A1 Dec. 13, 2007 2 fraction can be classi?ed in three groups (SHORUIGIN, P. fermentation and distillation conditions, as illustrated in Pet al. Ber. (1933). 66B: 1087-1093; SHORUIGIN, P P et Table 3 below, al., Zhurnal Obshchei Khimii (1934), 4 372-394): [0009] acidic compounds (10-25%): higher alcohols TABLE 3 (hexanol, hep'tanol, octanol, nonanol), fatty acids Fusel on production yidds (butync, Valenc: CaPFOIC, CaPryhC, Pelargonlc, CaPnC, (according to PATIL A.G.S. already cited) lauric, myristic, palmitic) and esters thereof (acetates, butyrates) Starting material Fusel oil [0010]ethylpyraZines, basic compounds and (5-10%): di-, tri- and tetram- 5213mm“ molass?s 23%‘: [0011] neutral compounds (60-80%): terpenes; Potatoes 541% [0012] the loW boiling fraction (LBF), Bp <132o C. This fraction represents the maJor portion of fusel 011 (95-98%) [0016] The uses of fusel Oil are quite diverse and have (PATIL already cued)‘ changed a great deal over the years. Before the 1930s, fusel [0013] Table 2 hereinafter presents some compositions of Oil W85 used only as a Source ofamy1a1coho1s.Around 1935, the LBF fraction of fusel oil. several studies begin to refer to the use of fusel oil or of its TABLE 2 Corn osition of the LBF fraction of ?isel oils of various ori ins % Iso- Active Iso H2O EtOH PrOH Iso-PrOH BuOH BuOH ArnOH ArnOH Beet molasses i 10.0 0.6 i 2.0 0.2 3.0 73.0 Beet molasses i 12.4 3.5 i i 9.5 i 74.6 (KUCUK Z. et a1. Turkish Journal of Chemistry (1998) 22(3), 289-300) Sugarbeet i 3.96 i 9.61 5.28 i 76.86 molasses (KHEDR, M. A. et a1. Pakistan Journal of Scienti?c and Industrial Research (1994) 37 (11) 488-490) Molasses i nd 13.2 i 0.2-0.7 15.8 18.4 37.4 (ULLMAN’S 1981) Potatoes i nd 14.0 i 0.5 15.5 15.0 55.0 (ULLMAN’S 1981) Fruits i nd 8.0 i 2.0 19.0 14.0 57.0 (ULLMAN’S 1981) Cereals i nd 9.1 i 0.2-0.7 19.0 20.0 13.0 (ULLMAN’S 1981) Waste i nd 7.0 i i 22.0 13.0 55.0 (ULLMAN’S 1981) The percentages of each alcohol vary greatly according to derivatives as solvents for paints, lacquers and nitrocellulose the starting material used for the fermentation, but also (MAKINO Z. et al., JP 111027; TING H. W. Research Inst. according to the method of fermentation or of distillation. Ann. Rept. Bur. Chem. (1936), 3, 75; CAVALIE H. R. et al., [0014] Fusel oil is a relatively viscous liquid that is straW FR988540). HoWever, the vast majority of authors Were yelloW to dark red in colour and has an unpleasant odour. studying the distillation and puri?cation of this distillation Before the development of processes of chemical synthesis, residue. Koslov et al. (Zhurnal Prikladnoi Khimii, (1954), fusel oil Was the only commercial source of amyl alcohols. 27, 223-225) used fusel oil as a ?otation agent for copper [0015] Subsequent to the production of 10001 of alcohol, and Zinc ores. Gukasyan et al. (Tsvetnye Metallyst, (1979), betWeen 1 and 111 of fusel oil can be obtained. This 12, 61-62) used fusel oil in place of trioctylamine for percentage depends on the starting material used and on the extracting rhenium from solutions thereof. Other authors US 2007/0286828 A1 Dec.
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