| Title of Invention | DIALKYL CARBONATES OF BRANCHED ALCOHOLS AND THEIR USE |
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| Abstract | DIALKYL CARBONATES OF BRANCHED ALCOHOLS AND THEIR USE Proposed are new dialkyl carbonates and also their use in cosmetic and/or pharmaceutical preparations |
| Full Text | Field of the invention The invention relates to dialkyl carbonates of branched alcohols and i their use in cosmetic and/or pharmaceutical preparations. Prior art The consumer has a large number of requirements in the field of cosmetic preparations for skin and hair care: Apart from the cleansing and care effects, which determine the intended use, value is placed on such different parameters as the highest possible dermatological tolerability, good re-oiling properties, elegant appearance, optimum sensorial impression and storage stability of human skin addition to a Preparations which are employed for cleansing and care and of hair as a rule comprise, in number of surface-active substances, above all oil substances and water. Oil substances/emollients which are employed are, for example, hydrocarbons, ester oils and plant and animal oils/fat a/waxes. To meet the high requirements of the market with respect to sensorial properties and optimum dermatological tolerability, novel oil substances and emulsifier mixtures are continuously being developed and tested. Dialkyl carbonates of linear alcohols and their use in cosmetics are known from the prior art, for example WO 97/47282 describes the use of octyl methyl carbonate in cosmetics and EP 1 510 199 describes the use of distearyl carbonate in cosmetics. Di-n-octyl carbonate is obtainable as a cosmetics raw material under the trade name Cetiol® CC (Cognis Deutschland GmbH & Co. KG). The preparation- of dialkyl carbonates is described in WO 97/47583. The symmetric dialkyl carbonates obtainable by the process described there contain e.g. 2-ethyl-l-hexyl pmethyl carbonate or 2-butyl-l-octyl methyl carbonate as by-products. A use of these compounds in cosmetics is not mentioned. EP 1 083 247 describes various short-chain branched dialkyl carbonates and [their suitability for washing metal surfaces. The object of the present invention was to provide novel raw materials for cosmetic applications which have an improved profile with respect to their sensorial properties (lightness, "non-greasy feeling on distribution, oi large number of the skin", softness, spreadability, absorption, ease of liness) and can be incorporated into a cosmetic formulations, for example as an oil substancd'/emollient or as an agent for imparting consistency. It should be possible for the raw materials to be 'incorporated both into W/0 and into 0/W formulations, and in particular they should be compatible with crystalline UV filters, pigments, antiperspirants,'; salts and silicones. It was of particular interest to provide raw materials which have It a good or improved dissolving power for pigments or inorganic UV" filters. It has been fpund, surprisingly, that the dialkyl carbonates of the present invention achieve this obj ect and in particular lead to sensorially light products. Surprisingly, the dialkyl carbonates of the present invention are suitable in particular for dissolving polar compounds,; in particular pigments or inorganic UV compounds in preparations is filters. An easier formulation of these active cosmetic and/or pharmaceutical thus achieved. Description of the invention Dialkyl carbonates are esters of carbonic acid of the general formula! 0=C(0R)2, wherein R denotes an alkyl radical. Dialkyl carbonates are named either by preceding the ; term "carbonate" by the alkyl substituents, or! as carbonic acid "alkyl" esters. Thus e.g. 0=C{OC8Hi7)2 lis called dioctyl carbonate or carbonic acid dioctyl ester, or e.g. 0=C(0CaH5) (OCgHiv) is called ethyl octyl carbonates or carbonic acid ethyl octyl ester. In the following, the formula R-0-CO-O-R is used for the dialkyl carbonates. The invention [provides dialkyl carbonates of the formula (I) ' R1O-CO-OR2 (I) , wherein - R1 is a2 2-propyl-1-heptyl radical and R1 represents linear or branched or cyclic hydrocarbon radicals having 1 to 22 carbon atoms and 0 or 1 to 3 double bonds, or - R1 is a R2-ethyl-l-butyl radical, R1 represents linear' or branched or cyclic hydrocarbon radicals having 1 to 22 carbon atoms and 0 or It 1 to 'l3 double bonds, wherein R^ is not 2- ethyl-butyl. In a preferred embodiment of the invention, R2 differs from R . In a preferred embodiment of the invention, R1 and R2 are a 2-propyl-1-heptyl radical. This embodiment of the invention thus relates to di (2-propyl-l-heptyl) carbonate. The invention lalso provides dialkyl carbonates the formula (II) R^O-CO-OR* (II) wherein R1 is chosen from the group consisting of the isodecyl radical, neodecyl radical, isoundecyl radical, isododecyl radical, isotridecyl radical, 2-pentylnonyl radical, 2-hexyldecyl radical, 2-heptyl-undecyl radical, isostearyl radical, 2-octyl-dodecyl radical, 2-butyl-l-octyl radical and 2-ethyl-l-hexyl radical, and R** represents linear or branched or cyclic hydrocarbon radicals having 1 to 22 carbon atoms and 0 or 1 to 3 double bonds, wherein R^ is not identical to R1, excluding 2-butyl-l-octyl methyl carbonate and 2-ethyl-1-hexyl methyl carbonate. The invention • allso provides dialkyl carbonates of the formula (II) ,1 R1O-CO-OR* (II) wherein R^ is chosen from the group consisting of the isodecyl radical', neodecyl radical, isoundecyl radical, isododecyl radical, isotridecyl radical, 2-pentylnonyl radical, 2-hexyldecyl radical, 2-heptyl-undecyl radical, isostearyl radical and 2-octyl-dodecyl radical and R^ represents linear or branched or cyclic hydrocarbon radi'cals having 1 to 22 carbon atoms and 0 or 1 to 3 double bonds, wherein R is not identical to 2-Hexyldecyl methyl carbonate is particularly preferred in the context of the invention. The invention also provides dialkyl carbonates of the formula (III) R1O-CO-OR2 (III), m which R |j represents linear or branched or cyclic hydrocarbon radicals having 1 to 22 carbon atoms and 0 or 1 to 3 double bonds and R2 represents branched hydrocarbon radicals having more than 12 carbon atoms and 0 or 1 to 3 double bonds. A preferred embodiment of the invention relates to dialkyl carbonates of the formula (III) R^O-CO-OR*' (III) , in which R| represents linear or branched or cyclic hydrocarbon radicals having 1 to 22 carbon atoms and 0 or ,1 to 3 double bonds and R^ represents branched hydrocarbon radicals having more than 12 carbon atom and 0 or 1 double bond, wherein R is not identical to R2. The invention also provides dialkyl carbonates of the formula (V) R1 fO-CO-OR2 (V) , in which I R^ represents branched or cyclic hydrocarbonj radicals having 1 to 22 carbon atoms and 0 or l' to 3 double bonds and R^° represents branched hydrocarbon radicals having more than 12 carbon atoms and 0 or 1 to 3 double bonds, excluding methyl-(2R, 6R, 3E)-6,lO-dimethyl-3,9- undecadien-2-yl carbonate. The invention also provides the use of the dialkyl carbonates of the formulae (1) , (II) , (III) and (V) in cosmetic and/or 'pharmaceutical preparations. The invention | also provides the use of dialkyl carbonates of the formula (IV) R'O-CO-OR^ (IV) f( in which ij R represents branched hydrocarbon radicals having 3 to 22 carbon atoms and 0 or 1 to 3 double bonds and R^ represents linear or branched or cyclic j hydrocarbon radicals having 1 to 22 carbon atoms and 0 or 1 to 3 double bonds and wherein R1 is not identical to R2, in cosmetic and/or pharmaceutical preparations. In a preferred! embodiment of the invention, dialkyl carbonates of the formula (IV) are used, excluding Wherein R represents methyl, ethyl or isopropyl. In a preferred embodiment of the invention, dialkyl carbonates of the formula (IV) in which R^ represents branched or linear hydrocarbon radicals having 3 to 22 carbon atoms and p or 1 to 3 double bonds are used. In a preferred embodiment of the invention, dialkyl carbonates of the formula (IV) in which R^ represents branched hydrocarbon radicals having 3 to 22 carbon atoms and 0 or 1 to 3 double bonds are used. In a particularly preferred embodiment of the invention, dialkyl carbonates of the formula (IV) which contain a total carbon number of greater than 12 are used. R1, R2 and R3 can be linear or branched or cyclic hydrocarbon radicals having 1 to 22 carbon atoms and 0 or 1 to 3 double Ijbonds, R1 can be linear or branched or cyclic hydrocarbon radicals having 2 to 22 carbon atoms and 0 or 1 to 3 double bonds. R^ can be branched hydrocarbon radicals having 3 to 22 carbon atoms and 0 or 1 to 3 double bonds. R1 can be branched hydrocarbon radicals having more than 12 carbon atoms land 0 or 1 double bond. R1 can be branched hydrocarbon radicals having more than 12 carbon atoms and | 0 or 1 to 3 double bonds. R^ can be branched or cyclic hydrocarbon radicals having 1 to 22 carbon atoms and 0 or 1 to 3 double bonds. Linear alkyl rsidicals which may be mentioned as examples are: methyl, ethyl, butyl, pentyl, hexyl, heptyl, octyl, ;; nonyl, decyl, undecyl, undecenyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, octadecenyl, nonadecyl, eicosanyl (=C20),; docosanyl (= C22) radicals. Branched alkyl i radical which may be mentioned as examples are: 2-methylpropyl, iso-butyl, iso-pentyl, such as e.g. 2,2,-dimethylpropyl (=neopentyl), 3- methylbutyl (=iso-pentyl), iso-hexyl, i-octyl, such as e.g. 2-ethyl-hexyl or 3 -ethyl-hexyl or 4-ethylhexyl or 5-ethylhexyl radicals, i-decyl radicals, such as e.g. the trimethylheptyl radical (= neodecyl radical), isostearyl, isooctyl, isononyl, isodecyl, isotridecyl, i 2-ethylbutyl, |2-ethylhexyl, 2-propylheptyl, 2- butyloctyl, 2 -biityldecyl, 2 -hexyloctyl, 2 -hexyldecyl, 2-hexyldodecyl, 2;-octyldecyl radical. Cyclic alkyl radicals which may be mentioned are the borneyl and isoborneyl radical and cyclohexyl radical. The invention also provides the use of all the abovementioned dialkyl carbonates in cosmetic preparations. It has been found, surprisingly, that the dialkyl carbonates according to the invention are particularly suitable for the preparation of cosmetic preparations, anci they are suitable in particular as oil substances/emollients and/or agents which impart consistency in cosmetic preparations. The dialkyl carbonates according to the invention are furthermore I suitable for the preparation of pharmaceutical preparations, wherein the dialkyl carbonates are employed as technical auxiliary substance, such as e.g. oil substances. The dialkyl carbonates according to the invention can serve for the preparation of cosmetic preparations, such as, for example, hair shampoos, hair lotions, foam baths, shower baths, creams, gels, i| lotions, alcoholic and aqueous/alcoholic solutions, emulsions, wax/fat compositions, stick preparations, powders or ointments. These compositions can furthermore contain as further auxiliary substances and additives mild surfactants emulsifiers, pearlescent waxes, agents which impart consistency, thi ckening agents, over-greasing agents, stabilizers, polymers, silicone compounds, fats, waxes, lecithins, phospholipids, biogenic active compounds, UV light protection factors, antioxidants, deodorants, antiperspirants,i antidandruff agents, film-forming agents, swelling agents, insect repellants, self-tanning agents, tyrosine inhibitors (depigmentation agents), hydrbtropic substances, solubilizers, preservatives, perfume oils, dyestuffs and the like. The use of the dialkyl carbonates as oil substances is preferred. 11 The dialkyl carbonates according to the invention can be used in cosmetic formulations as so-called "light emollients" in order to establish specific properties, such as e.g. spreading properties or volatility. The dialkyl carbonates according to the invention furthermore make it possible to prepare cosmetic if formulations of stable viscosity. Preparation The preparation!) of the dialkyl carbonates is carried out by processes known to the person skilled in the art, for example by transesterif ication of lower dialkyl carbonates, such as, for example, dimethyl carbonate, diethyl carbonate, dipropyl carbonate or dibutyl carbonate, with the corresponding alcohols or alcohol mixtures in the presence of a catalyst, as described, for example, in WO 97/47583. other preparation processes are described in M. Dierker: Lipid Technology, 2004, 16(6), p. 130-134. Examples Example 1: Preparation of hexyldecyl methyl carbonate 1,350 g (15 mol) of dimethyl carbonate were initially introduced into'a 4 1 stirred apparatus with a dropping funnel with 14 g of sodium methylate (30 % strength in methanol) and the mixture was heated up to 80 °C. 699 g {1.5 mol) of hexyldecanol were then added dropwise over a period of 2 hours and the mixture was subsequently stirred at 80 °C for a further 9 hours. During this period, the methanol formed was distilled off from the reaction mixture over a distillation attachment. GC evaluation of the crude product gave a composition of: 4 % of hexyldecanol, 7 9 % of asymmetric hexyldecyl methyl carbonate and 13 % of symmetric di-hexyldecyl carbonate. | The pH was adjusted to pH 3-4 with 14 g of H3PO4 (85 % strength) and excess dimethyl carbonate was distilled off. The sodium phosphate which had precipitated out u was filtered off with suction and the product was i( fractionated. The reaction product, hexyldecyl methyl It carbonate, is obtained as a colorless oil with a boiling point of! 125-125 °C under 0.4 mbar. Example 2: Formulations with hexyldecyl methyl carbonate The following cosmetic recipes were prepared with the hexyldecyl methyl carbonate prepared according to Example 1. All the data are in wt.%. Recipe no. 1 2 Trade name (INCI; name) Dehymuls®LE (PEG-3 0 dipolyhydroxystearate) 5.00 4.00 Lameform®TGI (polyglyceryl-3 diisostearate) 0.00 2 .00 Hexyldecyl methyl carbonate 20.00 20.00 MgS04*7H20 1.00 1.00 Glycerol 99.5 % 1 5.00 5.00 Formalin soln. 37 % strength0.10.15 Dist. water ! to 100 to 100 1 Recipe no. : li 345 Trade name (INci name) Emulgade® PL 68/So (cetearyl glucoside (and) cetearyl alcohol) i| 4.50 0.00 0.00 Eumulgin® VL75 (lauryl glucoside (and) polyglyceryl-2 dipolyhydroxystearate (and) glycerol) 0.00 4.50 0.00 Eumulgin® B2 (cet|:eareth-20) 0.00 0.00 2.00 Hexyldecyl methyl carbonate 16.0016.00 16 .00 Carbopol® 980 (carbomer) 0.00 0.30 0 .00 Lanette® 0 (cetearyl alcohol)0.000.00 5.00 KOH (20 % strength) 0.00 0.60 0.00 Glycerol 99.5 % ! 3.003 .00 3.00 Formalin soln. 37 % strength 0.15 0.15 0.15 Dist. water i| to 100 to 100to 100 We claim:- 1. A dialkyl carbonate of the formula (I) R 0-CO-OR (I), wherein | represents linear or branched or cyclic hydrocarbon radicals having 1 to 22 carbon atoms and 0 or 1 to 3 double bonds, or represents linear | or branched or cyclic hydrocarbon radicals having 1 to 22 carbon atoms and 0 or 1 to 3' double bonds, wherein R1 is not 2-II ethyl-If-butyl. 2. A dialkyl carbonate as claimed in claim 1, wherein R1 and R1 are a 2-propyl-1-heptyl radical. 3. A dialkyl carbonate of the formula (II) R1O-CO-OR2 wherein R is chosen from the group consisting of the isodecyl radical, neodecyl radical, isoundecyl radical, ispdodecyl radical, isotridecyl radical, 2-pentylnonyl radical, 2-hexyldecyl radical, 2- heptyl-undecyl radical, isostearyl radical, 2- octyl-dodecyl radical, 2-butyl-i-octyl radical and 2-ethyl-l-hexyl radical, and R1 represents linear or branched or cyclic hydrocarbon radicals having 1 to 22 carbon atoms and 0 or 1 to 3 double bonds wherein R1 11 is not identical to R1, excluding 2- butyl-1-octyl methyl carbonate and 2-ethyl-l-hexyl methyl carbbnate. 4. A dialkyl carbonate of the formula (III) R O-CO-OR in which R1 represents linear or branched or cyclic hydrocarbon [radicals having 1 to 22 carbon atoms and 0 or 1 I to 3 double bonds and R1 represents branched hydrocarbon radicals having more than 12 carbon atoms and 0 or 1 double bond, wherein R is not identical to R1. 5. A dialkyl carbonate of the formula (V) R1 O-CO-OR2 in which ' R1 represents branched or cyclic hydrocarbon! radicals having 1 to 22 carbon atoms and 0 or l' to 3 double bonds and R1° represents branched hydrocarbon radicals having more than 12 carbon atoms and 0 or 1 to 3 double bonds, excluding methyl (2R, 6R, 3E)-6,10-dimethyl-3,9- undecadien-S-y1 carbonate. 6. . The use of the dialkyl carbonate as claimed in at least one of claims 1 to 4 5 in cosmetic and/or pharmaceutibal preparations. 7. The use of li dialkyl carbonates of the formula (IV) R'1O-CO-OR1 (IV) m which I R represents branched hydrocarbon radicals having 3 to 22 carbon atoms and 0 or 1 to 3 double bonds and R1 represents linear or branched or cyclic \ hydrocarbon radicals having 3 to 22 carbon atoms and 0 or 1 to 3 double bonds and wherein R'.; is not identical to R% in cosmetic and/or pharmaceutical preparations, excluding 8. The use as claimed in claim 7, characterized in that R® represents branched hydrocarbon radicals having 3 to 22 carbon atoms and 0 or 1 to 3 doiible bonds. 9. The use as claimed in claim 7 or 8, characterized in that the dialkyl carbonates contain more than 12 carbon atoms. 10. The use as claimed in at least one of claims 6 to 9 as oil !substances or as agents which impart consistency. |
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| Patent Number | 278929 | ||||||||||||
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| Indian Patent Application Number | 3443/CHENP/2009 | ||||||||||||
| PG Journal Number | 01/2017 | ||||||||||||
| Publication Date | 06-Jan-2017 | ||||||||||||
| Grant Date | 04-Jan-2017 | ||||||||||||
| Date of Filing | 17-Jun-2009 | ||||||||||||
| Name of Patentee | COGNIS IP MANAGEMENT GMBH | ||||||||||||
| Applicant Address | HENKELSTR.67, 40589 DUSSELDORF, | ||||||||||||
Inventors:
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| PCT International Classification Number | C07C 69/96 | ||||||||||||
| PCT International Application Number | PCT/EP2007/010351 | ||||||||||||
| PCT International Filing date | 2007-11-29 | ||||||||||||
PCT Conventions:
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