WO2002024624A1 - Agents d'ouverture de cycle d'epoxydes obtenus par la chimie des graisse et leur utilisation dans des preparations cosmetiques - Google Patents

Agents d'ouverture de cycle d'epoxydes obtenus par la chimie des graisse et leur utilisation dans des preparations cosmetiques Download PDF

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Publication number
WO2002024624A1
WO2002024624A1 PCT/EP2001/010482 EP0110482W WO0224624A1 WO 2002024624 A1 WO2002024624 A1 WO 2002024624A1 EP 0110482 W EP0110482 W EP 0110482W WO 0224624 A1 WO0224624 A1 WO 0224624A1
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WO
WIPO (PCT)
Prior art keywords
preparations
reaction products
hair
alcohols
long
Prior art date
Application number
PCT/EP2001/010482
Other languages
German (de)
English (en)
Inventor
Thomas Otto Gassenmeier
Lars Zander
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
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 Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Priority to AU2001293806A priority Critical patent/AU2001293806A1/en
Publication of WO2002024624A1 publication Critical patent/WO2002024624A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/722—Ethers of polyoxyalkylene glycols having mixed oxyalkylene groups; Polyalkoxylated fatty alcohols or polyalkoxylated alkylaryl alcohols with mixed oxyalkylele groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/046—Aerosols; Foams
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/45—Derivatives containing from 2 to 10 oxyalkylene groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants
    • 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
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
    • C07C69/708—Ethers
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/72—Ethers of polyoxyalkylene glycols

Definitions

  • the invention relates to ring opening products of long-chain epoxy compounds with 10-70 carbon atoms with terpene alcohols, which are suitable as components in cosmetic preparations for cleaning and care of the hair, skin and teeth.
  • aqueous preparations of surface-active substances are used for the cleaning and care of the body. These often have the disadvantage that they swell the skin too much, degrease the skin and hair too much and thus impair the condition of the skin and hair.
  • This problem is generally countered by adding moisturizing, skin-moistening or hair-activating components to the surfactant preparations, which counteract the degreasing of the skin and give the hair better combability and more shine.
  • Suitable additives are e.g. Oil components, e.g. Silicone oils and water-soluble polymers, especially cationic polymers with quaternary ammonium groups.
  • Oil components e.g. Silicone oils and water-soluble polymers, especially cationic polymers with quaternary ammonium groups.
  • Cosmetic-pharmaceutical oil components are known from EP 0 135 018 B1, which can be obtained by reacting epoxidized triglyceride oils with monohydric C 1 -C 4 alcohols. From the ' German Offenlegungsschrift DE 34 32 219 AI ethylene oxide addition products to reaction products of epoxidized triglyceride oils with mono- or polyvalent C 6 -C 6 alcohols were known as solubilizers for perfume oils. It has now been observed that reaction products of long-chain epoxy compounds with terpene alcohols are particularly interesting oleochemical oil components with new cosmetic properties.
  • the invention relates to reaction products of long-chain epoxy compounds with 10-70 carbon atoms with terpene alcohols of the formula R J OH with ring opening of the epoxy groups to form groups of the formula R'OCC-OH, in which R 1 is the residue of a mono-, sesqui- or diterpene alcohol ,
  • the new oleochemical terpene ethers are interesting oil components for cosmetic and pharmaceutical preparations, which have good skin and mucous membrane compatibility, good stability against rancidity and a high dissolving power for cosmetic and dermatological active ingredients. They are also distinguished by the fact that they undergo a gradual hydrolysis with the elimination of the terpene alcohols in acidic media. In terms of application technology, this can be used to release monoterpene alcohols with interesting fragrance properties in a controlled manner over long periods of time and thereby give the products a pleasant fragrance over a longer period of time than would be possible with a content of conventional volatile fragrances.
  • the new oleochemical terpene ethers can also be modified in their hydrophilicity and solution properties by adding ethylene oxide or propylene oxide. It has been shown that addition products to the ring opening products of long-chain, oleochemical epoxy compounds have very interesting hair cosmetic properties. You can e.g. Preparations for washing or rinsing the hair are added and bring about a marked improvement in the sensory parameters of the hair washed or treated with it.
  • the invention therefore furthermore relates to adducts of 1-100 mol of ethylene oxide, propylene oxide or mixtures thereof with reaction products of long-chain epoxy compounds having 10-70 C atoms with mono-, sesqui- or diterpene alcohols.
  • Linear and slightly branched epoxides of alpha-olefins or olefins with an internal double bond are suitable as long-chain epoxy compounds with 10-30 C atoms.
  • Linear olefin epoxides with 10-30 C atoms are particularly suitable.
  • the long-chain epoxy compounds are particularly preferably selected from the epoxidized unsaturated C 16 -C 22 fatty acid esters of mono- or polyhydric alcohols with 1-10 C atoms.
  • Suitable epoxy compounds are e.g. epoxidized oleic acid methyl ester, epoxidized oleic acid decyl ester, epoxidized olerlerucate, epoxidized ethylene glycol dioleate, epoxidized triolein or an epoxidized unsaturated vegetable oil such as e.g. epoxidized sperm oil or epoxidized jojoba oil.
  • the long-chain epoxy compound is selected from epoxidized triglyceride oils. Epoxidized triglycerides are known as so-called epoxy plasticizers and are commercially available products.
  • oils such as Soybean oil, linseed oil, tall oil, cottonseed oil, peanut oil, palm oil, sunflower oil, rapeseed oil or claw oil are obtained with the peracetic acid process described in the American Chemical Society 67, March 1945, pages 412 to 414.
  • unsaturated oils such as Soybean oil, linseed oil, tall oil, cottonseed oil, peanut oil, palm oil, sunflower oil, rapeseed oil or claw oil are obtained with the peracetic acid process described in the American Chemical Society 67, March 1945, pages 412 to 414.
  • Triglyceride oils with an iodine number of 50-150 are particularly suitable, which, with extensive epoxidation, are converted into epoxidates with an epoxy oxygen content of 3-10% by weight.
  • Epoxidates with a content of 4-8% by weight epoxy oxygen are particularly suitable for the further reaction with terpene alcohols.
  • Suitable monoterpene alcohols are e.g. Geraniol, Menthol, Citronellol, Nerol, Linalool, Terpineol, Borneol, Thujol, Sabinol, Myrtenol, Thymol, Verbenol, Fenchol and Piperitol.
  • Suitable sesquiterpene alcohols are, for example, farnesol, caryophyllenols, bisabolol, patchulial alcohol and betulenol.
  • Suitable diterpene alcohols are, for example, phytol, retinol and geranylgeraniol.
  • the terpene alcohols for the reaction products according to the invention are particularly preferably selected from the group of the monoterpene alcohols geraniol, menthol, citronellol, nerol, linalool and terpineol.
  • reaction of the long chain epoxy compounds with the terpene alcohols is preferred in the presence of an acid catalyst, e.g. performed by concentrated sulfuric acid.
  • an acid catalyst e.g. performed by concentrated sulfuric acid.
  • a particularly preferred ring opening process is described in DE 44 46 877 AI, using fluoroalkanesulfonic acids as acid catalysts.
  • the reaction leads to the opening of the epoxy groups (oxirane rings) with the formation of a group R ⁇ -CC-OH, in which R 1 is the rest of the mono-, sesqui- or diterpene alcohol.
  • the terpene alcohol is used in excess with respect to the epoxy groups in order to achieve a large opening of all oxirane groups.
  • the excess terpene alcohol can be removed by distillation after the reaction.
  • liquid, oxidation-stable, skin and mucous membrane compatible oil components are obtained with monoterpene alcohols. These have good dissolving power for cosmetic and dermatological active ingredients and good dispersing power for pigments. They are therefore particularly suitable as oil components for the production of cosmetic and therapeutic preparations for the care and treatment of the skin, in particular emulsions, creams, ointments, aerosol preparations, stick preparations and deodorants.
  • the use in deodorants is particularly interesting because the gradual release of the pleasantly smelling terpene alcohols on the skin enables a particularly long-lasting deodorant effect.
  • the addition of ethylene oxide, propylene oxide or mixtures thereof onto the reaction products according to the invention of long-chain epoxy compounds having 10-70 carbon atoms with terpene alcohols is carried out according to the known process of ethoxylation or propoxylation in the presence of acidic or basic catalysts.
  • the addition products obtained thereby are mixtures of homologous polyglycol ethers whose average degree of ethoxylation or propoxylation corresponds to the molar amount of the alkylene oxide added. With increasing degree of ethoxylation, the hydrophilicity of these addition products also increases, which gradually become water-soluble when 50-70% by weight of ethylene oxide is added (based on the addition product).
  • the adducts of ethylene oxide and / or propylene oxide with the oleochemical terpene ethers according to the invention have surface-active properties and can also be used as emulsifiers, co-emulsifiers and solubilization aids.
  • they show interesting hair cosmetic properties and are particularly suitable as conditioning components in preparations for washing and rinsing the hair, in particular an improvement in the hair shine, the manageability, the volume, the softness and the feel of the hair.
  • Another object of the invention is therefore the use of the addition products of 1-100 mol ethylene oxide and / or propylene oxide to the reaction products according to the invention of long-chain epoxy compounds with 10-70 carbon atoms with terpene alcohols as hair-activating component in preparations for cleaning and care of the hair.
  • Such preparations can e.g. Shampoos and hair rinses, hair dyes, permanent wave fixatives or other rinse-off products.
  • a particularly preferred embodiment of the invention are preparations for cleaning the hair and skin containing surface-active substances, the addition products of 1-100 mol ethylene oxide and / or propylene oxide onto reaction products according to the invention of long-chain epoxy compounds with terpene alcohols in an amount of 0.1-10 % By weight.
  • the adducts of ethylene oxide and propylene oxide with the oleochemical terpene ether according to the invention have a particularly good compatibility with cosmetic surfactant systems, as are customary in skin and hair cleansers.
  • the ring opening product was reacted with the ethylene oxide in an autoclave at 5 bar and 140 ° C. for 3 hours. The reaction mixture was then neutralized with lactic acid. A clear, light brown oil was thus obtained as the product.
  • the data relate to% by weight of anhydrous active substance.
  • compositions 2.1 to 2.3 were used for the treatment of 2 g, pre-cleaned locks of hair. For this purpose, 1 g of the composition per strand was left to act at 20 ° C. for one minute, then the hair was rinsed out and dried under air-conditioned conditions.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dispersion Chemistry (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Epoxy Compounds (AREA)

Abstract

Produits de réaction de composés époxy à chaînes longues comportant 10-70 atomes de carbone avec des alcools terpéniques de formule R1OH, avec ouverture du cycle des groupes époxy, pour former des groupements de formule R1O-C-C-OH, dans laquelle R1 représente le reste d'un alcool monoterpénique, sesquiterpénique ou diterpénique. Ces produits sont appropriés, sous forme de composants huileux, pour la production de préparations cosmétiques ou pharmaceutiques destinées au soin et au traitement de la peau, notamment sous forme d'émulsions, crèmes, pommades, aérosols, bâtonnets ou déodorants. Les produits de réaction d'huiles triglycéridiques époxydés avec des alcools monoterpéniques tels que le géraniol, le menthol, le citronellol, le nérol, le linalol ou le terpinéol sont des produits particulièrement appropriés. L'hydrophilie et les propriétés de dissolution de ces nouveaux éthers terpéniques, obtenus par la chimie des graisses, peuvent en outre être modifiées à volonté par addition d'oxyde d'éthylène ou d'oxyde de propylène. Lors de cette opération, il s'est avéré les produits de l'addition sur agents d'ouverture de cycle de composés époxy, obtenus par la chimie des graisses, à chaînes longues, présentaient des propriétés très intéressantes pour la cosmétique capillaire. Ils peuvent par exemple être ajoutés à des préparations servant à laver et à rincer les cheveux pour améliorer notablement les paramètres sensoriels des cheveux lavés ou traités avec lesdits produits.
PCT/EP2001/010482 2000-09-20 2001-09-11 Agents d'ouverture de cycle d'epoxydes obtenus par la chimie des graisse et leur utilisation dans des preparations cosmetiques WO2002024624A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2001293806A AU2001293806A1 (en) 2000-09-20 2001-09-11 Ring opening agents of fat chemical epoxides obtained by fat chemistry and the use thereof in cosmetic preparations

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10046432A DE10046432A1 (de) 2000-09-20 2000-09-20 Ringöffnungsprodukte fettchemischer Epoxide und deren Verwendung in kosmetischen Zubereitungen
DE10046432.7 2000-09-20

Publications (1)

Publication Number Publication Date
WO2002024624A1 true WO2002024624A1 (fr) 2002-03-28

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PCT/EP2001/010482 WO2002024624A1 (fr) 2000-09-20 2001-09-11 Agents d'ouverture de cycle d'epoxydes obtenus par la chimie des graisse et leur utilisation dans des preparations cosmetiques

Country Status (3)

Country Link
AU (1) AU2001293806A1 (fr)
DE (1) DE10046432A1 (fr)
WO (1) WO2002024624A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003086515A1 (fr) * 2002-04-12 2003-10-23 Microdrug Ag Dispositif formant un rasoir a poudre a flux d'air
WO2007001694A1 (fr) 2005-06-24 2007-01-04 Exxonmobil Chemical Patents Inc. Composition adhésive de copolymère de propylène fonctionnalisé

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0135018A2 (fr) * 1983-07-22 1985-03-27 Henkel Kommanditgesellschaft auf Aktien Composants d'huile cosmétique-pharmaceutique
DE3432219A1 (de) * 1984-09-01 1986-03-13 Henkel KGaA, 4000 Düsseldorf Loesungsvermittler fuer oelloesliche parfuemoele
WO1998028249A1 (fr) * 1996-12-20 1998-07-02 Rhodia Chimie Composes terpeniques polyalcoxyles, leur procede de preparation et leur utilisation comme agents demoussants
DE19818410A1 (de) * 1998-04-24 1999-10-28 Wella Ag Haar- und Körperreinigungsmittel mit verminderter Hautirritation

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1947748B2 (de) * 1968-10-08 1973-09-20 Reichhold-Albert-Chemie Ag, 2000 Hamburg Verfahren zur Herstellung von wasser verdunnbaren, vinylmodifizierten Kunstharzen auf der Grundlage von Polyathern
GB9501861D0 (en) * 1995-01-31 1995-03-22 Croda Int Plc Solubilised essential oils
DE19851430A1 (de) * 1998-11-09 2000-05-11 Cognis Deutschland Gmbh Verwendung von kationaktiven Mischungen

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0135018A2 (fr) * 1983-07-22 1985-03-27 Henkel Kommanditgesellschaft auf Aktien Composants d'huile cosmétique-pharmaceutique
DE3432219A1 (de) * 1984-09-01 1986-03-13 Henkel KGaA, 4000 Düsseldorf Loesungsvermittler fuer oelloesliche parfuemoele
WO1998028249A1 (fr) * 1996-12-20 1998-07-02 Rhodia Chimie Composes terpeniques polyalcoxyles, leur procede de preparation et leur utilisation comme agents demoussants
DE19818410A1 (de) * 1998-04-24 1999-10-28 Wella Ag Haar- und Körperreinigungsmittel mit verminderter Hautirritation

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003086515A1 (fr) * 2002-04-12 2003-10-23 Microdrug Ag Dispositif formant un rasoir a poudre a flux d'air
WO2007001694A1 (fr) 2005-06-24 2007-01-04 Exxonmobil Chemical Patents Inc. Composition adhésive de copolymère de propylène fonctionnalisé

Also Published As

Publication number Publication date
AU2001293806A1 (en) 2002-04-02
DE10046432A1 (de) 2002-04-04

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