WO2004011581A1 - Compositions obtenues par reduction de lanoline - Google Patents

Compositions obtenues par reduction de lanoline Download PDF

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Publication number
WO2004011581A1
WO2004011581A1 PCT/GB2003/003299 GB0303299W WO2004011581A1 WO 2004011581 A1 WO2004011581 A1 WO 2004011581A1 GB 0303299 W GB0303299 W GB 0303299W WO 2004011581 A1 WO2004011581 A1 WO 2004011581A1
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WO
WIPO (PCT)
Prior art keywords
lanolin
composition
lanolins
hydrocarbons
hydrogenation
Prior art date
Application number
PCT/GB2003/003299
Other languages
English (en)
Inventor
Ian Steel
Original Assignee
Croda International Plc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Croda International Plc filed Critical Croda International Plc
Priority to AU2003251362A priority Critical patent/AU2003251362A1/en
Publication of WO2004011581A1 publication Critical patent/WO2004011581A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/005—Antimicrobial preparations
    • 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
    • A61K8/31—Hydrocarbons
    • 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
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/925—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of animal origin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/04—Antipruritics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/16—Emollients or protectives, e.g. against radiation
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B11/00—Recovery or refining of other fatty substances, e.g. lanolin or waxes
    • C11B11/005—Lanolin; Woolfat
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
    • C11C1/002—Sources of fatty acids, e.g. natural glycerides, characterised by the nature, the quantities or the distribution of said acids
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/12—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by hydrogenation
    • C11C3/126—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by hydrogenation using catalysts based principally on other metals or derivates

Definitions

  • the present invention relates to novel reduced lanolin products, particularly those comprising a high lanolin hydrocarbon content, processes for preparing them, especially catalytic hydrogenation, and their use, particularly in topical formulations.
  • Wool wax is a true wax in the chemical sense, there being no glycerides present, but rather it comprises a highly complex mixture of esters of fatty alcohols with fatty acids, both of which are of several different types and covering a wide range of molecular weight.
  • a typical composition of a pharmaceutical grade lanolin comprises, by weight:
  • Lanolin also contains a small amount of hydrocarbons, referred to as 'paraffins' by the European Pharmacopoeia (EP) and as 'petrolatum' by the US Pharmacopoeia.
  • the maximum permitted amount of lanolin hydrocarbons is 1 % by weight determined (EP) by column chromatography on activated aluminium oxide.
  • Lanolin alcohols can be prepared by reduction, as described in British patent specification no. 2 058 777, which discloses two routes for converting wool wax acids to their corresponding alcohols via hydrogenation.
  • the first route involves in situ esterification of distilled wool wax acids with a low molecular weight alcohol followed by high-pressure hydrogenation.
  • the second route simply uses a pre- prepared ester (eg methyl, ethyl, isopropyl, etc.) as the hydrogenation substrate.
  • Unwanted by-products, namely ⁇ , ⁇ -diols, which have pronounced anti- emulsification properties, could be separated from the resultant fatty alcohols by either molecular distillation or crystallisation.
  • reduced lanolin can be prepared, comprising a high proportion of lanolin hydrocarbons, which have excellent emollient properties, are aesthetically pleasing (which would, in use, improve compliance), and have potential in anti-inflammatory, barrier repair and anti-itch properties, particularly for wound healing.
  • reduced lanolin herein is meant the products of the process of the extended reduction of lanolin or lanolin-derived feedstock, whether produced by a process such as described in more detail below or by an alternative method.
  • reduced lanolin products may alternatively be obtained by one or more synthetic chemical methods and/or by extraction or concentration of naturally- occurring hydrocarbons and other components of lanolin.
  • the preferred feedstock for the reduction is isopropyl lanolate, particularly the solid fraction of isopropyl lanolate as mentioned below
  • the reduced lanolin products of the invention may be prepared by reduction of lanolin or a lanolin derivative, such as other lanolin fatty acids esters, woolwax alcohols, lanolin fatty acids and lanolin alcohols.
  • the reduced lanolin products of the invention preferably comprise at least 15% lanolin hydrocarbons, with the balance comprising partially-reduced lanolin derivatives, such as lanolin alcohols.
  • the present invention provides a lanolin-derivable composition comprising at least 25% w/w of lanolin hydrocarbons and at most 75% w/w lanolin alcohols, based on the total weight of the composition.
  • the composition comprises at least 50% w/w of lanolin hydrocarbons; more preferably, at least 75% w/w of lanolin hydrocarbons, and, especially, at least 90% w/w of lanolin hydrocarbons.
  • the reduced lanolin products of the invention are preferably substantially lanolin ester-free, that is to say that less than 2% of the reduced lanolin product comprises lanolin ester reduction feedstock. Especially preferred is when the reduced lanolin product comprises less than 1% lanolin ester reduction feedstock.
  • Chemical synthesis of reduced lanolin products of the invention may be undertaken by extended hydrogenation using a method analogous to the above-mentioned known processes for preparing lanolin alcohols.
  • extended hydrogenation is herein meant hydrogenation undertaken under such conditions and for a sufficient period of time to enable production of the reduced lanolin having high hydrocarbon content, as defined herein. Such conditions and/or time period are in excess of those required to produce the lanolin alcohols.
  • the reduction feedstock may be prepared by reaction of lanolin fatty acids and a short chain aliphatic alcohol, such as ROH wherein R is C 1-4 alkyl, preferably isopropyl (IPA), and a suitable catalyst.
  • a preferred catalyst is para-toluene sulphonic acid (j TSA), although other conventional esterification catalysts (such as those mentioned in patent specification no. WO 98/30532) may be used.
  • IPA is the alcohol: after removal of excess IPA, the crude ester can be base-washed to yield crude low acid value isopropyl lanolate.
  • the crude isopropyl lanolate can then be split by molecular distillation to yield solid and liquid fractions, which contain isopropyl esters of C16 - C40 lanolin fatty acids & C8 - C22 lanolin fatty acids, respectively.
  • the solid fraction of low acid value isopropyl lanolate is used as the reduction feedstock.
  • the feedstock is free of typical catalyst poisons (sulphur, chlorine & heavy metals) and has an acid value of less than 1 mgKOHg "1 . Still more preferred is when lower molecular weight lanolin fatty acid esters (C14 and lower) are excluded from the reduction feedstock.
  • Reduction of the isopropyl lanolate feedstock yields the reduced lanolin system. Reduction is preferably carried out by catalytic hydrogenation.
  • Hydrogenation may be carried out in the presence of a suitable hydrogenation catalyst at a high pressure in the range of from 100 to 30850 kPa, more preferably in the range 17450 to 30850 kPa, and a temperature in the range of from 100 to 300°C, more preferably in the range 200 to 300°C.
  • a suitable hydrogenation catalyst for this process is copper chromite.
  • Hydrogenation may be carried out also in the presence of a suitable hydrogenation catalyst at a high pressure in the range of from 100 to 30850 kPa, more preferably in the range 17450 to 30850 kPa, but at a temperature greater than 350°C.
  • a suitable hydrogenation catalyst at a high pressure in the range of from 100 to 30850 kPa, more preferably in the range 17450 to 30850 kPa, but at a temperature greater than 350°C.
  • Preferred hydrogenation catalysts for this process are metals such as Ni, Co, Rh or Ru, supported on alumina, silica or Ti0 2 .
  • the extended reduction, especially hydrogenation, process of the invention accordingly provides novel reduced lanolin products.
  • a typical composition according to the invention is one wherein the lanolin hydrocarbon content comprises in the range of from 15 to 45%, such as 20 to 40%, each of n-alkanes, 2-methylalkanes and 3-methylalkanes, based on the total weight of the lanolin hydrocarbons in the composition.
  • the lanolin hydrocarbons each comprise in the range of from 8 to 40, such as 12 to 32 carbon atoms.
  • the present invention provides a composition according to any preceding claim, preparable by extended hydrogenation of lanolin fatty acid esters, especially wherein the lanolin fatty acid esters are obtainable by reaction of lanolin fatty acids with iso-propyl alcohol. Because of the lanolin derivative content of the compositions according to preferred embodiments of the invention, they find particular use in the treatment of parts of the mammalian body, especially the skin, for various purposes.
  • suitable topical delivery forms may include sprays, aerosols, liniments, lotions, bath dispersions, shampoos, drenches, ointments, pastes, creams, gels, salves and patches and may also comprise non-topical forms such as pessaries, suppositories or any other suitable dosage form such as is typically used for the delivery of cosmetically or pharmacologically active agents.
  • the formulations may accordingly comprise oil-in- water or water-in-oil or complex emulsions, or solutions or suspensions.
  • Drops according to the present invention may comprise sterile aqueous or oily solutions and may be prepared by dissolving the active ingredient in a suitable aqueous solution containing a bactericide and/or fungicidal agent and/or any other suitable preservative.
  • the resulting solution may then be clarified by filtration, transferred to a suitable container, and then sealed and sterilized by autoclaving or maintaining at 90-100°C for half an hour.
  • the solution may be sterilized by filtration and transferred to the container by an aseptic technique.
  • Preservatives, bactericidal and fungicidal agents suitable for inclusion in the drops are phenylmercuric salts (0.002%), benzalkonium chloride (0.01%) and chlorhexidine acetate (0.01%).
  • Suitable solvents for the preparation of an oily solution include glycerol, diluted alcohol and propylene glycol.
  • Lotions according to the present -invention include those suitable for application to the eye.
  • An eye lotion may comprise a sterile aqueous solution optionally containing a bactericide or preservative prepared by methods similar to those for the preparation of drops.
  • Lotions or liniments for application to the skin may also include an agent to hasten drying and to cool the skin, such as an alcohol, or a softener or moisuriser such as glycerol or an oil such as castor oil or arachis oil.
  • Creams, ointments or pastes according to the present invention are semi-solid formulations of the active ingredient for external application. They may be made by mixing the active ingredient in granule or powdered form, alone or in solution or suspension in an aqueous or non-aqueous solution in suitable machinery, with a greasy or non-greasy basis.
  • the basis may comprise one or more of a hard, soft or liquid paraffin, glycerol, beeswax, a metallic soap; a mucilage; an oil such as vegetable oil, eg almond, corn, arachis, castor or olive oil; wool fat or its derivatives; or a fatty acid ester of a fatty acid together with an alcohol such as propylene glycol or macrogols.
  • the formulation may also comprise a suitable surface-active agent, such as an anionic, cationic or non-ionic surfactant such as glycol or polyoxyethylene derivatives thereof.
  • a suitable surface-active agent such as an anionic, cationic or non-ionic surfactant such as glycol or polyoxyethylene derivatives thereof.
  • Suspending agents such as natural gums may be incorporated, optionally with other inorganic materials such as silicaceous silicas, and other ingredients such as lanolin or other lanolin derivatives.
  • compositions of the invention may further be used as skin moisturizers or for the provision of a film or barrier to allow both the delivery of medicaments to underlying traumatised skin (eg to wounds, burns, ulcers) or to eczematous or psoriatic skin or to areas of generalised dry or damaged skin or hair, eg following excessive exposure to the sun or wind or after radiation or chemotherapy treatments, and also to prevent the actions of airborne infections to such aforesaid traumas.
  • traumatised skin eg to wounds, burns, ulcers
  • eczematous or psoriatic skin or to areas of generalised dry or damaged skin or hair eg following excessive exposure to the sun or wind or after radiation or chemotherapy treatments, and also to prevent the actions of airborne infections to such aforesaid traumas.
  • compositions particularly for use as a sunscreen, include one or more of a moisturizer, an emollient, an emulsifier, a preservative, a dispersant, a viscosity modifier, a herbal extract, a solvent, a chelating agent, an antioxidant, a waterproofing agent, a pH adjuster, a perfume, and a protein.
  • the composition may include one or more of: titanium dioxide, zinc oxide, benzophenone-3; benzophenone-4; octyl methoxycinnamate (Parsol 1789); 3,3,5- trimethylcyclohexyl salicylate; carbomer; hydroxyethyl cellulose; lanolin alcohols; cetyl phosphate; fatty alcohols; C 12 to C 15 alkyl benzoate; cyclomethicone; caprylic/capric triglycerides; mineral oil; glycerin; vitamin E; and isopropyl myristate.
  • a pharmaceutical formulation for treating skin inflammation caused by burns, by exposure to sunlight or by exposure to UV radiation comprising a composition of the invention and a physiologically acceptable carrier.
  • the carrier may therefore include excipients normally present in formulations for treating burns, such as antiseptic compounds, emollients, inorganics, humectants, moisturisers, anti-inflammatory agents, vitamins, preservatives, pH adjusters, proteins, herbal extracts, carriers/solvents, soothing/cooling agents, antioxidants, perfumes, emulsifiers and viscosity modifiers.
  • excipients normally present in formulations for treating burns such as antiseptic compounds, emollients, inorganics, humectants, moisturisers, anti-inflammatory agents, vitamins, preservatives, pH adjusters, proteins, herbal extracts, carriers/solvents, soothing/cooling agents, antioxidants, perfumes, emulsifiers and viscosity modifiers.
  • useful materials include glycerine, triethanolamine stearate, vitamin E, lanolin, zinc oxide, allantoin, calamine, sodium lactate, water, lactic acid, pro-
  • compositions of the invention also find use as carriers for one or more cosmetic or pharmaceutical active agents which are incorporated into the compositions so that they may be efficiently delivered to the skin, mucosae or other parts of the body by application of the composition thereto.
  • compositions of the invention may be incorporated into the compositions of the invention, examples of which are well known in the art.
  • suitable such bio-affecting active agents are disclosed, for example, in US patent specification no. 4560553.
  • the amount of active which is incorporated may be selected according to the amount required to be delivered, which again will generally be in accordance with well established principles and formulation techniques.
  • the compositions of the invention may also be used as vehicles for transdermally delivered drugs in pharmaceutical or veterinary applications.
  • compositions of the invention may also find use in industrial, domestic or agricultural applications.
  • Such applications may include treatment of leather, treatment of textiles, inks, metal-working, rust preventatives, cutting fluids, lubrication, penetrating oils, tissue-softening, fabric care, furniture, shoe & leather polishes, crop protection and as an agrochemical active or for delivery of agrochemical actives.
  • the crude hydrocarbons were purified by distillation on a laboratory scale molecular still.
  • a portion of the hydrocarbon product was dissolved in heptane and analysed using a 100% dimethylpolysiloxane capillary column (RH-1 or equivalent), 30 m x 0.25 ⁇ m i.d., film thickness 0.2 mm.
  • the injector and detector temperatures were 285 and 300 °C, respectively.
  • the oven program was as follows:
  • Peaks were assigned using a combination of standards for the n-alkanes and standards & theoretical elution orders for the 2- & 3-methylalkanes.
  • Distilled hydrocarbon product (29.98 g), produced according to Example 1 (C1 ), was allowed to equilibrate at -22 °C. After a sufficient length of time (24 to 96 h), the 5 clear liquid fraction was separated from the solid fraction by decantation.
  • Skin surface contour analysis was performed by taking silicone replicas of the skin. These were then, analysed by a mechanical profilometric technique, using the Hommel tester T-1000 ® (Hommelwerke GmbH).
  • the lanolin hydrocarbons demonstrated a significant decrease in Rzl compared to silicone at both 2 and 4.5 hours.
  • Moisturisation of the stratum corneum causes it to swell, making the skin's surface smoother.
  • the "moisturising potential" of a compound is therefore a valuable parameter used to assess the efficiency of an emollient.
  • the CorneometerTM ® CM825 (C+K, Germany) is an instrument which enables the determination of the water content of the stratum corneum by capacitance. This measurement is based on the completely different dielectric constant of water (81) and other substances (mostly ⁇ 7).
  • the measuring capacitor shows changes of capacitance according to the moisture content of the samples.
  • a glass lamina separates the metallic tracks (gold) in the probe head from the skin in order to prevent current conduction in the sample.
  • a scatterfield penetrates the very first layer of the skin and determines the dielectricity.
  • the penetration depth is very low at only 30-40 ⁇ m.
  • the most frequent allergens to give positive reactions were the metals, i.e., nickel, cobalt & chromate, the Fragrance mix, and the aminoglycoside antibiotics.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Dermatology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Wood Science & Technology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Rheumatology (AREA)
  • Zoology (AREA)
  • Microbiology (AREA)
  • Pain & Pain Management (AREA)
  • Toxicology (AREA)
  • Cosmetics (AREA)
  • Fats And Perfumes (AREA)
  • Medicinal Preparation (AREA)

Abstract

L'invention concerne une composition obtenue par réduction de lanoline ou de charge dérivée de lanoline. Cette composition comprend au moins 25% en poids d'hydrocarbures de lanoline et 75% en poids au maximum d'alcools de lanoline, sur la base du poids total de la composition.
PCT/GB2003/003299 2002-07-26 2003-07-28 Compositions obtenues par reduction de lanoline WO2004011581A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003251362A AU2003251362A1 (en) 2002-07-26 2003-07-28 Compositions formed from the reduction of lanolin

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB0217366.4A GB0217366D0 (en) 2002-07-26 2002-07-26 Compositions
GB0217366.4 2002-07-26

Publications (1)

Publication Number Publication Date
WO2004011581A1 true WO2004011581A1 (fr) 2004-02-05

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AU (1) AU2003251362A1 (fr)
GB (2) GB0217366D0 (fr)
WO (1) WO2004011581A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008155059A2 (fr) * 2007-06-19 2008-12-24 Cognis Ip Management Gmbh Mélanges d'hydrocarbures et leur utilisation
WO2008155060A2 (fr) * 2007-06-19 2008-12-24 Cognis Ip Management Gmbh Mélanges d'hydrocarbures et leur utilisation
WO2008155057A2 (fr) * 2007-06-19 2008-12-24 Cognis Ip Management Gmbh Mélanges d'hydrocarbures et leur utilisation
WO2008155061A2 (fr) * 2007-06-19 2008-12-24 Cognis Ip Management Gmbh Préparations cosmétiques contenant des hydrocarbures
EP2111847A1 (fr) * 2007-06-19 2009-10-28 Cognis IP Management GmbH Mélanges d'hydrocarbures et leur utilisation

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Publication number Priority date Publication date Assignee Title
GB2425475A (en) * 2005-01-29 2006-11-01 Croda Int Plc PEG or PPG lanolin derivatives as antipruritic agents

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Publication number Priority date Publication date Assignee Title
GB2058777A (en) * 1979-09-25 1981-04-15 Beiersdorf Ag Manufacture of wool wax alcohols
EP0341547A1 (fr) * 1988-05-09 1989-11-15 Henkel Kommanditgesellschaft auf Aktien Procédé d'hydrogénation catalytique de lanoline en alcool de lanoline

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JPS5437840A (en) * 1977-08-29 1979-03-20 Kanebo Ltd Hair cosmetics
JPH0426621A (ja) * 1990-05-21 1992-01-29 Dai Ichi Kogyo Seiyaku Co Ltd 制がん増強剤

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Publication number Priority date Publication date Assignee Title
GB2058777A (en) * 1979-09-25 1981-04-15 Beiersdorf Ag Manufacture of wool wax alcohols
EP0341547A1 (fr) * 1988-05-09 1989-11-15 Henkel Kommanditgesellschaft auf Aktien Procédé d'hydrogénation catalytique de lanoline en alcool de lanoline

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Title
NEUMÜLLER, OTTO-ALBRECHT: "Römpps Chemie-Lexikon, Band 1", 1979, FRANCKH'SCHE VERLAGSBUCHHANDLUNG, STUTTGART, XP002261403 *
NEUMÜLLER, OTTO-ALBRECHT: "Römpps Chemie-Lexikon, Band 4", 1979, FRANCKH'SCHE VERLAGSBUCHHANDLUNG, STUTTGART, XP002261404 *

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008155059A2 (fr) * 2007-06-19 2008-12-24 Cognis Ip Management Gmbh Mélanges d'hydrocarbures et leur utilisation
WO2008155060A2 (fr) * 2007-06-19 2008-12-24 Cognis Ip Management Gmbh Mélanges d'hydrocarbures et leur utilisation
WO2008155057A2 (fr) * 2007-06-19 2008-12-24 Cognis Ip Management Gmbh Mélanges d'hydrocarbures et leur utilisation
WO2008155061A2 (fr) * 2007-06-19 2008-12-24 Cognis Ip Management Gmbh Préparations cosmétiques contenant des hydrocarbures
EP2111847A1 (fr) * 2007-06-19 2009-10-28 Cognis IP Management GmbH Mélanges d'hydrocarbures et leur utilisation
WO2008155060A3 (fr) * 2007-06-19 2009-11-12 Cognis Ip Management Gmbh Mélanges d'hydrocarbures et leur utilisation
WO2008155059A3 (fr) * 2007-06-19 2009-11-12 Cognis Ip Management Gmbh Mélanges d'hydrocarbures et leur utilisation
WO2008155061A3 (fr) * 2007-06-19 2009-11-12 Cognis Ip Management Gmbh Préparations cosmétiques contenant des hydrocarbures
WO2008155057A3 (fr) * 2007-06-19 2009-12-03 Cognis Ip Management Gmbh Mélanges d'hydrocarbures et leur utilisation
JP2010530389A (ja) * 2007-06-19 2010-09-09 コグニス・アイピー・マネージメント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング 炭化水素混合物およびその使用
JP2010530390A (ja) * 2007-06-19 2010-09-09 コグニス・アイピー・マネージメント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング 炭化水素を含有する化粧品
JP2010531809A (ja) * 2007-06-19 2010-09-30 コグニス・アイピー・マネージメント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング 炭化水素混合物およびその使用
US20110059032A1 (en) * 2007-06-19 2011-03-10 Cognis Ip Management Gmbh Hydrocarbon Mixtures and use Thereof
US8309065B2 (en) 2007-06-19 2012-11-13 Cognis Ip Management Gmbh Hydrocarbon mixture and use thereof
US8895039B2 (en) 2007-06-19 2014-11-25 Cognis Ip Management Gmbh Cosmetic preparations containing hydrocarbons
US8956598B2 (en) 2007-06-19 2015-02-17 Cognis Ip Management Gmbh Hydrocarbon mixtures and use thereof
KR101553415B1 (ko) * 2007-06-19 2015-09-15 코그니스 아이피 매니지먼트 게엠베하 탄화수소 혼합물 및 이의 용도
JP2015166373A (ja) * 2007-06-19 2015-09-24 コグニス・アイピー・マネージメント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＣｏｇｎｉｓ ＩＰ Ｍａｎａｇｅｍｅｎｔ ＧｍｂＨ 炭化水素を含有する化粧品
JP2017206536A (ja) * 2007-06-19 2017-11-24 コグニス・アイピー・マネージメント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＣｏｇｎｉｓ ＩＰ Ｍａｎａｇｅｍｅｎｔ ＧｍｂＨ 炭化水素を含有する化粧品
US10537505B2 (en) 2007-06-19 2020-01-21 Cognis Ip Management Gmbh Hydrocarbon mixtures and use thereof

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GB0317524D0 (en) 2003-08-27
AU2003251362A1 (en) 2004-02-16

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