Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
  • C07C69/96—Esters of carbonic or haloformic acids
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K31/00—Medicinal preparations containing organic active ingredients
  • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
  • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
  • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
  • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/37—Esters of carboxylic acids
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
  • A61Q19/10—Washing or bathing preparations
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/02—Preparations for cleaning the hair
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C68/00—Preparation of esters of carbonic or haloformic acids

Definitions

• the invention relates to dialkyl carbonates of branched alcohols and their use in cosmetic and/or pharmaceutical preparations.
• 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.
• Preparations which are employed for cleansing and care of human skin and of hair as a rule comprise, in addition to a 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/fats/waxes.
• 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).
• dialkyl carbonates 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-1-hexyl methyl carbonate or 2-butyl-1-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 the skin”, softness, spreadability, absorption, ease of distribution, oiliness) and can be incorporated into a large number of cosmetic formulations, for example as an oil substance/emollient or as an agent for imparting consistency. It should be possible for the raw materials to be incorporated both into W/O and into O/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 a good or improved dissolving power for pigments or inorganic UV filters.
• dialkyl carbonates of the present invention achieve this object and in particular lead to sensorially light products.
• the dialkyl carbonates of the present invention are suitable in particular for dissolving polar compounds, in particular pigments or inorganic UV filters. An easier formulation of these active compounds in cosmetic and/or pharmaceutical preparations is thus achieved.
• Dialkyl carbonates are esters of carbonic acid of the general formula O ⁇ C(OR) 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. O ⁇ C(OC 8 H 17 ) 2 is called dioctyl carbonate or carbonic acid dioctyl ester, or e.g. O ⁇ C(OC 2 H 5 ) (OC 8 H 17 ) is called ethyl octyl carbonates or carbonic acid ethyl octyl ester. In the following, the formula R—O—CO—O—R is used for the dialkyl carbonates.
• the invention provides dialkyl carbonates of the formula (I)
• R 1 differs from R 2 .
• R 1 and R 2 are a 2-propyl-1-heptyl radical. This embodiment of the invention thus relates to di-(2-propyl-1-heptyl)carbonate.
• the invention also provides dialkyl carbonates the formula (II) R 3 O—CO—OR 4 (II)
• R 3 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-1-octyl radical and 2-ethyl-1-hexyl radical, and R 4 represents linear or branched or cyclic hydrocarbon radicals having 1 to 22 carbon atoms and 0 or 1 to 3 double bonds, wherein R 3 is not identical to R 4 , excluding 2-butyl-1-octyl methyl carbonate and 2-ethyl-1-hexyl methyl carbonate.
• the invention also provides dialkyl carbonates of the formula (II)
• R 3 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 4 represents linear or branched or cyclic hydrocarbon radicals having 1 to 22 carbon atoms and 0 or 1 to 3 double bonds, wherein R 3 is not identical to R 4 .
• 2-Hexyldecyl methyl carbonate is particularly preferred in the context of the invention.
• the invention also provides dialkyl carbonates of the formula (III)
• a preferred embodiment of the invention relates to dialkyl carbonates of the formula (III)
• the invention also provides dialkyl carbonates of the formula (V)
• the invention also provides the use of the dialkyl carbonates of the formulae (I),(II), (III) and (V) in cosmetic and/or pharmaceutical preparations.
• the invention also provides the use of dialkyl carbonates of the formula (IV)
• dialkyl carbonates of the formula (IV) are used, excluding
• R represents methyl, ethyl or isopropyl.
• dialkyl carbonates of the formula (IV) in which R 8 represents branched or linear hydrocarbon radicals having 3 to 22 carbon atoms and 0 or 1 to 3 double bonds are used.
• dialkyl carbonates of the formula (IV) in which R 8 represents branched hydrocarbon radicals having 3 to 22 carbon atoms and 0 or 1 to 3 double bonds are used.
• dialkyl carbonates of the formula (IV) which contain a total carbon number of greater than 12 are used.
• R 2 , R 5 and R 8 can be linear or branched or cyclic hydrocarbon radicals having 1 to 22 carbon atoms and 0 or 1 to 3 double bonds
• R 4 can be linear or branched or cyclic hydrocarbon radicals having 2 to 22 carbon atoms and 0 or 1 to 3 double bonds
• R 7 can be branched hydrocarbon radicals having 3 to 22 carbon atoms and 0 or 1 to 3 double bonds.
• R 6 can be branched hydrocarbon radicals having more than 12 carbon atoms and 0 or 1 double bond.
• R 10 can be branched hydrocarbon radicals having more than 12 carbon atoms and 0 or 1 to 3 double bonds.
• R 9 can be branched or cyclic hydrocarbon radicals having 1 to 22 carbon atoms and 0 or 1 to 3 double bonds.
• Linear alkyl radicals 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.
• 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, and 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 suitable for the preparation of pharmaceutical preparations, wherein the dialkyl carbonates are employed as technical auxiliary substance, such as e.g. oil substances.
• 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, lotions, alcoholic and aqueous/alcoholic solutions, emulsions, wax/fat compositions, stick preparations, powders or ointments.
• cosmetic preparations such as, for example, hair shampoos, hair lotions, foam baths, shower baths, creams, gels, lotions, alcoholic and aqueous/alcoholic solutions, emulsions, wax/fat compositions, stick preparations, powders or ointments.
• compositions can furthermore contain as further auxiliary substances and additives mild surfactants, oil substances, emulsifiers, pearlescent waxes, agents which impart consistency, thickening agents, over-greasing agents, stabilizers, polymers, silicone compounds, fats, waxes, lecithins, phospholipids, biogenic active compounds, UV light protection factors, antioxidants, deodorants, antiperspirants, antidandruff agents, film-forming agents, swelling agents, insect repellants, self-tanning agents, tyrosine inhibitors (depigmentation agents), hydrotropic substances, solubilizers, preservatives, perfume oils, dyestuffs and the like.
• mild surfactants oil substances, emulsifiers, pearlescent waxes, agents which impart consistency, thickening agents, over-greasing agents, stabilizers, polymers, silicone compounds, fats, waxes, lecithins, phospholipids, biogenic active compounds, UV light protection factors, antioxidants, deodor
• 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 formulations of stable viscosity.
• dialkyl carbonates are carried out by processes known to the person skilled in the art, for example by transesterification 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.
• lower dialkyl carbonates such as, for example, dimethyl carbonate, diethyl carbonate, dipropyl carbonate or dibutyl carbonate
• a catalyst as described, for example, in WO 97/47583.
• 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.

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• General Chemical & Material Sciences (AREA)
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• Oil, Petroleum & Natural Gas (AREA)
• Cosmetics (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Medicinal Preparation (AREA)

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• 2006
  • 2006-12-08 EP EP06025406A patent/EP1930311A1/fr not_active Withdrawn
• 2007
  • 2007-11-29 ES ES07846876.6T patent/ES2503723T3/es active Active
  • 2007-11-29 WO PCT/EP2007/010351 patent/WO2008067946A1/fr active Application Filing
  • 2007-11-29 KR KR1020097011621A patent/KR101485203B1/ko active IP Right Grant
  • 2007-11-29 EP EP07846876.6A patent/EP2094641B1/fr active Active
  • 2007-11-29 JP JP2009539644A patent/JP5399260B2/ja active Active
  • 2007-11-29 CN CN201410802932.8A patent/CN104592031A/zh active Pending
  • 2007-11-29 CN CNA2007800452365A patent/CN101547889A/zh active Pending
  • 2007-11-29 US US12/518,208 patent/US20100331565A1/en not_active Abandoned
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