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WO1996026710A1 - Preparations cosmetiques et/ou pharmaceutiques - Google Patents

Preparations cosmetiques et/ou pharmaceutiques Download PDF

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Publication number
WO1996026710A1
WO1996026710A1 PCT/EP1996/000740 EP9600740W WO9626710A1 WO 1996026710 A1 WO1996026710 A1 WO 1996026710A1 EP 9600740 W EP9600740 W EP 9600740W WO 9626710 A1 WO9626710 A1 WO 9626710A1
Authority
WO
WIPO (PCT)
Prior art keywords
dimer diol
cosmetic
technical
mixtures
trimer triol
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/EP1996/000740
Other languages
German (de)
English (en)
Inventor
Achim Ansmann
Rolf Kawa
Annette Schwarz
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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 Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of WO1996026710A1 publication Critical patent/WO1996026710A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • 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
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • 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

Definitions

  • the invention relates to cosmetic and / or pharmaceutical preparations containing selected polyols and the use of the polyols as oil bodies.
  • oil-soluble bases are needed, the task of which is to transport polar ingredients, such as, for example, active ingredients or moisture, through the lipid barrier of the skin.
  • polar ingredients such as, for example, active ingredients or moisture
  • a variety of natural and synthetic oils are suitable for this purpose, for example almond or avocado oil or ester oils based on short-chain triglycerides.
  • the oil components in the agents mentioned also have a nourishing effect which is directly related to the skin oiling. Products are desired by the consumer which impart a non-sticky feeling of skin smoothness and suppleness that occurs as quickly as possible and lasts longer.
  • cosmetic oil bodies can be divided into low-spreading (below 300 mm 2 / 10min), medium-spreading (approx. 300 to 1000 mm 2 / 10min) and high-spreading oils (above 1000 mm 2 / 10min).
  • Emulsions for the formulation of extensive care and Massageöl- are oil bodies with high greasiness, ie with a low Speit capacity of less than 100 mm 2/10 minutes erforder ⁇ Lich. These include vegetable oils, (33 2 mm / 10 min), such as peanut oil (62 mm 2/10 min) or castor oil.
  • vegetable oils (33 2 mm / 10 min)
  • peanut oil 62 mm 2/10 min
  • castor oil castor oil.
  • concentrations above 15% by weight for example, no longer lead to the formation of an emulsion.
  • a further disadvantage is the susceptibility to oxidation of the oil bodies mentioned at the outset and the fact that they are practically insoluble in polar media such as, for example, ethanol.
  • the complex object of the present invention was therefore to provide cosmetic and / or pharmaceutical preparations with an oil body content that have a low Zeidler spreading value of ⁇ 100 mm / 10 min, can be easily in W / Have O-emulsions incorporated, little susceptible to oxidation and moreover are still satisfactorily soluble in polar media such as ethanol.
  • the invention relates to cosmetic and pharmaceutical preparations containing technical dimer diol / trimer triol mixtures with an average of 24 to 66, preferably 36 to 54 carbon atoms.
  • Dimer diol / trimer triols are technical mixtures which are obtained by oligomerizing unsaturated fatty acids having 12 to 22, preferably 16 to 18 carbon atoms or their methyl esters and subsequent high-pressure hydrogenation.
  • the oligomerization of unsaturated fatty acids is a known electrocyclic reaction, about which in review articles, for example by A. Behr in Fat Sei. Technol. 93, 340 (1991), G.Spiteller in Fat Sei.Technol. .94 * 41 (1992) or P.Daute et al. in Fat Sei.Technol. J95_, 91 (1993) is reported.
  • oligomerization In oligomerization, on average two to three fatty acids come together and form dimers or trimers, which predominantly have cycloaliphatic structures. In addition to the fraction of the dimers and trimers, a so-called monomer fraction is obtained in which there are unreacted starting materials and branched monomers which have arisen in the course of the reaction by isomerization. There is of course also a fraction of higher oligomers, which, however, is generally not of major importance.
  • the oligomerization can be carried out thermally or in the presence of noble metal catalysts.
  • the reaction is preferably carried out in the presence of clays such as montomorillonite [cf. Greases, soaps, paints. 72, 667 (1970)].
  • the regulation of the content of dimers and trimers and the extent of the monomer fraction can be controlled by the reaction conditions.
  • Typical examples are palmoleic acid, oleic acid, elaidic acid, petroselinyl acid, linoleic acid, linolenic acid, conjugated fatty acid, elaeostearic acid, ricinoleic acid, gadoleic acid, erucic acid and their technical mixtures with saturated fatty acids.
  • Typical examples of suitable technical mixtures are uncured split fatty acids from natural triglyc ride with iodine numbers in the range from 40 to 140, such as palm fatty acid, tallow fatty acid, rapeseed oil fatty acid, sunflower fatty acid and the like. Split fatty acids with a high oleic acid content are preferred.
  • esters In addition to the fatty acids, their esters, preferably methyl esters, can also be dimerized. It is also possible to oligomerize the acid and convert it to the methyl ester before the hydrogenation.
  • the acid or ester group is hydrogenated to the alcohol group in a manner known per se in the presence of heterogeneous cupfer / chromium or cupfer / zinc catalysts at temperatures in the range from 200 to 300 ° C. and pressures of about 250 to 350 bar .
  • Dimer diol / trimer diol mixtures which are particularly preferred for the purposes of the invention, are obtained by oligomerizing technical oleic acid and subsequent high-pressure hydrogenation and have a dimer diol content of 33 to 99% by weight and a trimer triol content of 1 to 67% by weight. % on.
  • the monomer content can be 1 to 15% by weight and, if necessary, reduced by distillation.
  • Cosmetic or pharmaceutical preparations are primarily to be understood as skin care products which can contain the technical dimer diol / trimer triol mixtures in amounts of 1 to 35 and preferably 5 to 25% by weight, based on the composition.
  • the agents according to the invention such as creams and lotions, can contain additional oil bodies, emulsifiers, fats and waxes, stabilizers and superfatting agents, thickeners, biogenic agents, film formers, preservatives, colorants and fragrances exhibit.
  • Suitable emulsifiers are both known W / O and 0 / W emulsifiers, such as, for example, hardened and ethoxylated castor oil, polyglycerol fatty acid esters or polyglycerol poly ricinoleates or hydroxystearates, and also fatty alcohol sulfates, soaps, fatty alcohol ethoxylates, alkyl oligoglucosides and the like.
  • Typical examples of fats are glycerides, waxes which may be used include beeswax, paraffin wax or microwaxes, if appropriate in combination with hydrophilic waxes, for example cetylstearyl alcohol.
  • Metal salts of fatty acids such as magnesium, aluminum and / or zinc stearate can be used as stabilizers.
  • Substances such as, for example, polyethoxylated lanolin derivatives, lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides can be used as superfatting agents, the latter simultaneously serving as foam stabilizers.
  • Suitable thickeners are, for example, polysaccharides, in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, and also higher molecular weight polyethylene glycol mono- and diesters of fatty acids, polyacrylates, polyvinyl alcohol and polyvinyl pyrrolidone.
  • Biogenic active substances are understood to mean, for example, plant extracts and vitamin complexes.
  • Common film formers are, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinyl pyrrolidone, vinyl pyrrolidone-vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives, collagen, hyaluronic acid or its salts and similar compounds.
  • Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid.
  • Suitable pearlizing agents are, for example, glycol distearic acid esters such as ethylene glycol distearate, but also fatty acid monoglycol esters.
  • the dyes which can be used are the substances which are suitable and approved for cosmetic purposes, as compiled, for example, in the publication "Cosmetic Dyes” of the Dye Controls of the German Research Foundation, published by Verlag Chemie, Weinheim, 1984, pp. 81-106. These dyes are usually used in concentrations of 0.001 to 0.1% by weight, based on the mixture as a whole.
  • the total proportion of auxiliaries and additives can be 1 to 50, preferably 5 to 40% by weight and the non-aqueous proportion (“active substance content”) 20 to 80, preferably 30 to 70% by weight, based on the composition.
  • the preparation of the agents can be carried out in a manner known per se, i.e. for example by hot, cold, hot-hot / cold or PIT emulsification. This is a purely mechanical process, there is no chemical reaction.
  • the technical dimer diol / trimer triol mixtures are notable for their high fatness and low spreading capacity. They can be easily incorporated into emulsions and are surprisingly readily soluble in polar media. Another object of the invention therefore relates to their use as oil bodies or superfatting agents for the production of cosmetic and / or pharmaceutical preparations in which they are present in concentrations of 1 to 35, preferably 5 to 25% by weight on the means - may be included.
  • Lameform ( R ) TGI polyglyceryl-3-diisostearate.
  • Emulsions I to III are according to the invention, emulsion IV is used for comparison. While highly viscous creams with a rich care effect were obtained in the first three cases, in the case of the comparative example it was not possible to produce a stable emulsion.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Dermatology (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Emergency Medicine (AREA)
  • Birds (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne de nouvelles préparations cosmétiques et pharmaceutiques contenant des mélanges techniques diols dimères/triols trimères ayant, en moyenne, de 24 à 66 atomes de carbone. Les polyols peuvent être utilisés comme huiles et se caractérisent par une faible capacité d'étalement.
PCT/EP1996/000740 1995-03-02 1996-02-22 Preparations cosmetiques et/ou pharmaceutiques Ceased WO1996026710A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19507203.0 1995-03-02
DE1995107203 DE19507203A1 (de) 1995-03-02 1995-03-02 Kosmetische und/oder pharmazeutische Zubereitungen

Publications (1)

Publication Number Publication Date
WO1996026710A1 true WO1996026710A1 (fr) 1996-09-06

Family

ID=7755396

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1996/000740 Ceased WO1996026710A1 (fr) 1995-03-02 1996-02-22 Preparations cosmetiques et/ou pharmaceutiques

Country Status (2)

Country Link
DE (1) DE19507203A1 (fr)
WO (1) WO1996026710A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003051324A1 (fr) * 2001-12-19 2003-06-26 Cognis Deutschland Gmbh & Co. Kg Produits de protection solaire cosmetiques et/ou pharmaceutiques
FR2839308A1 (fr) * 2002-04-24 2003-11-07 Croda Japan Kk Derive de diol et composition le contenant
US7226587B2 (en) 2001-06-01 2007-06-05 Wyeth Compositions and methods for systemic administration of sequences encoding bone morphogenetic proteins
US7413753B2 (en) 2001-06-08 2008-08-19 Wyeth Calcium phosphate delivery vehicles for osteoinductive proteins

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL2345406T3 (pl) 2010-01-16 2017-02-28 Aachener Centrum Für Technologietransfer In Der Ophthalmologie E.V. Kompozycje z dimerodiolu jako zamienniki płynów ustrojowych
US8697756B2 (en) 2012-07-10 2014-04-15 Acto E.V. Dimer diol compositions as substitutes of body fluids

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1043507A (en) * 1964-02-25 1966-09-21 Marchon Products Ltd Cyclo-aliphatic diols and process for their preparation
US3947382A (en) * 1967-02-01 1976-03-30 Cincinnati Milacron, Inc. Mildness additive
US3981990A (en) * 1967-02-01 1976-09-21 Cincinnati Milacron, Inc. Skin protective compositions
GB1577926A (en) * 1976-11-03 1980-10-29 Johnson & Johnson Cloth or paper impregnated with skinprotective agents

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1043507A (en) * 1964-02-25 1966-09-21 Marchon Products Ltd Cyclo-aliphatic diols and process for their preparation
US3947382A (en) * 1967-02-01 1976-03-30 Cincinnati Milacron, Inc. Mildness additive
US3981990A (en) * 1967-02-01 1976-09-21 Cincinnati Milacron, Inc. Skin protective compositions
GB1577926A (en) * 1976-11-03 1980-10-29 Johnson & Johnson Cloth or paper impregnated with skinprotective agents

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7226587B2 (en) 2001-06-01 2007-06-05 Wyeth Compositions and methods for systemic administration of sequences encoding bone morphogenetic proteins
US7413753B2 (en) 2001-06-08 2008-08-19 Wyeth Calcium phosphate delivery vehicles for osteoinductive proteins
WO2003051324A1 (fr) * 2001-12-19 2003-06-26 Cognis Deutschland Gmbh & Co. Kg Produits de protection solaire cosmetiques et/ou pharmaceutiques
FR2839308A1 (fr) * 2002-04-24 2003-11-07 Croda Japan Kk Derive de diol et composition le contenant

Also Published As

Publication number Publication date
DE19507203A1 (de) 1996-09-05

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