WO2012016578A1 - Agents épaississants pour phases cosmétiques huileuses - Google Patents

Agents épaississants pour phases cosmétiques huileuses Download PDF

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Publication number
WO2012016578A1
WO2012016578A1 PCT/EP2010/004824 EP2010004824W WO2012016578A1 WO 2012016578 A1 WO2012016578 A1 WO 2012016578A1 EP 2010004824 W EP2010004824 W EP 2010004824W WO 2012016578 A1 WO2012016578 A1 WO 2012016578A1
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WO
WIPO (PCT)
Prior art keywords
cosmetic
use according
oil
polymer
polymers
Prior art date
Application number
PCT/EP2010/004824
Other languages
English (en)
Inventor
Wolfgang Denuell
Cindy Muenzenberg
Oliver Pietsch
Original Assignee
Cognis Ip Management Gmbh
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 Cognis Ip Management Gmbh filed Critical Cognis Ip Management Gmbh
Priority to PCT/EP2010/004824 priority Critical patent/WO2012016578A1/fr
Publication of WO2012016578A1 publication Critical patent/WO2012016578A1/fr

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Classifications

    • 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
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8164—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers, e.g. poly (methyl vinyl ether-co-maleic anhydride)
    • 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
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin

Definitions

  • the present invention is related to the area of cosmetic compositions and covers oil- based compositions comprising certain polymers suitable for increasing the viscosity.
  • Cosmetic hair and skin-care emulsions are expected by the consumer to satisfy a number of requirements. Apart from the cleansing and caring effects which determine the particular application, importance is attributed to such diverse parameters as highest possible dermatological compatibility, good lipid-layer-enhancing properties, elegant appearance, optimal sensory impression and shelf life. Besides a number of surfactants, cosmetic hair- and skin-care preparations generally contain, above all, oil components and water.
  • the oil component (emollients) used include, for example, hydrocarbons, ester oils and vegetable and animal oils/fats/waxes.
  • compositions irrespectively if present as homogenous solution, dispersion or aqueous emulsion contain certain compounds to increase their viscosity.
  • water-soluble vegetable gums such as alginates and tragacanth
  • water-soluble cellulose derivatives such as carboxymethyl cellulose, hydroxyethyl cellulose, methyl cellulose
  • synthetic polymers such as polyvinylalcohol, polyethylene oxides or polyacrylic acids.
  • the object of the present invention has been to find new rheology modifiers able to provide the appropriate rheological behavior to oil-based cosmetic compositions.
  • R and R' independently from each other represents either hydrogen or methyl or stand for a linear or branched alkyl or alkenyl radical having 2 to 22 carbon atoms with the proviso, that at least one moiety R or R' is not a hydrogen atom as thickening agent for cosmetic acceptable oil phases.
  • oil phase encompass all kinds of oil bodies or oil components, in particular vegetable oils, fatty acid alkyl esters based on said C6-C22 fatty acids, mineral oils, silicone oils and their mixtures.
  • cosmetic acceptable refers to those kinds of organic oils or blends of oils which can be used in such compositions which came into intense and/or direct contact to the human skin, scalp, hair or nails, without harming them.
  • Examples illustrating the nature of suitable hydrophobic carriers without limiting the invention to these examples are: C6-C22-Fatty alcohols, Guerbet alcohols based on fatty alcohols having 6 to 18, preferably 8 to 10, carbon atoms, esters of linear C6- C22-fatty acids with linear or branched C6-C22-fatty alcohols or esters of branched C6-C13-carboxylic acids with linear or branched C6-C22-fatty alcohols, such as, for example, myristyl myristate, myristyl palmitate, myristyl stearate, myristyl isostearate, myristyl oleate, myristyl behenate, myristyl erucate, cetyl myristate, cetyl palmitate, cetyl stearate, cetyl isostearate, cetyl oleate, cetyl behenate, cetyl erucate, stearyl myristate
  • esters of linear C6-C22-fatty acids with branched alcohols in particular 2-ethylhexanol, esters of C18-C38- alkylhydroxy carboxylic acids with linear or branched C6-C22-fatty alcohols, in particular dioctylmalate, esters of linear and/or branched fatty acids with polyhydric alcohols (such as, for example, propylene glycol, dimerdiol or trimertriol) and/or Guerbet alcohols, triglycerides based on C6-C10-fatty acids, liquid mono-/di-/triglyceride mixtures based on C6-C18-fatty acids, esters of C6-C22-fatty alcohols and/or Guerbet alcohols with aromatic carboxylic acids, in particular benzoic acid, esters of C2- CI 2- dicarboxylic acids with linear or branched alcohols having 1 to 22 carbon atoms or polyols having 2 to 10 carbon atom
  • Finsolv® TN linear or branched, symmetrical or asymmetrical dialkyl ethers having 6 to 22 carbon atoms per alkyl group, such as, for example, dicaprylyl ether (Cetiol® OE), ring-opening products of epoxidized fatty acid esters with polyols and/or silicone oils (cyclomethicones, silicone methicone grades, etc.).
  • a further preferred oil phase is selected from silicone oils, especially hydrophobically modified silicone oils (e.g. Dow Corning® 2502 by Dow Corning).
  • Suitable as cosmetic acceptable oil phases, or part of this oil phases are also vegetable oils, but with the proviso that rape seed oil, and derivates thereto, including rape seed oil methyl esters are excluded, because those oils are potentially irritating the human skin. Also excluded are oils, which are based on non-renewable sources, like mineral oils, paraffin oils and preferably commercial white oil.
  • Especially preferred cosmetic acceptable oil phase are selected from
  • Especially preferred oil phases according to the present teaching are selected from groups iii), iv), v) and/or vi) as well as any mixture thereof.
  • the polymers according to the present invention represent polymers containing monomers according to the following formula (I)
  • ROOC-CH CH-COOR' (I) in which R and R' independently from each other represents either hydrogen or methyl or stand for a linear or branched alkyl or alkenyl radical having 1 to 22 carbon atoms with the proviso, that at least one moiety R or R' is not a hydrogen atom.
  • Polymers according to this invention are such compounds which contain at least 5 and preferably at least 8 monomers.
  • the polymers according to this invention may comprise only one monomer (then homopolymers are present) or may contain two or more monomers according to formula (I) (then co- or terpolymers are present). In one preferred embodiment the polymers will only consist of monomers according to formula (I) above.
  • Such monomers according to formula (I) are selected where both groups R and R' are selected from linear or branched, saturated or unsaturated alkyl or alkenyl radical having 1 to 22 carbon atoms. More preferred are monomers where R and/or R' are selected from saturated alkyl groups with contain 6 to 22, and more advantageous from 12 to 22, and preferred from 16 to 22 C-atoms.
  • a certain preferred embodiment pertains to the use of polymers, containing monomers according to formula (I), whereby the groups R and/or R' are selected from blends of linear saturated C16/C18 alkyl chains, or of blends of C18/C22 alkyl chains, or both. Linear groups R and/ or R' might be preferred over branched ones.
  • the most preferred moiety R and/or R' is the behenyl-group, comprising of a linear saturated alkyl group with 22 C-atoms.
  • R and R' both represent such a behenyl group in the monomers according to formula (I).
  • the polymers are based preferably on fumaric acid mono- or diesters accordingly, and can be described as polyfumarates.
  • the polymers may consist of the monomers according to formula (I), but also suitable in the sense of the present invention are co- polymers, containing together with the monomers according to formula (I) different monomers too.
  • a preferred different monomer is fumaric acid. But in the sense of the present invention homo-polymers consisting of fumaric acid monomers only are excluded. But it is preferred to use polymers which contains fumaric acid together with other monomers according to formula (I) wherein in these other monomers at least one moiety R or R' will not be a hydrogen atom.
  • preferred monomers are those where R and/or R' is selected from a behenyl group.
  • R and/or R' are methyl, ethyl, propyl or butyl groups, or these groups are derived from C6-C22 fatty alcohols, as for example capryl alcohol, 2- ethylhexyl alcohol, C8-C10 fatty alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, linolyl alcohol, conjugated linolyl alcohol, linoleyl alcohol, ricinolyl alcohol, 12- hydroxystearyl alcohol, gadoleayl alcohol, arachidonyl alcohol, behenyl alcohol, eruciyl alcohol, Guerbet alcohols based on fatty alcohols having 6 to 18 carbon atoms, and their mixtures.
  • C6-C22 fatty alcohols as for example capryl alcohol, 2- ethylhexyl alcohol, C8-C10 fatty alcohol, lauryl
  • Such polymers based on monomers which comprising short (C6-C14) and/or long chain (C16-C22) fatty alcohols, for example esters obtained from 2-ethylhexyl alcohol and behenyl alcohol as moieties R and/or R'.
  • esters obtained from 2-ethylhexyl alcohol and behenyl alcohol as moieties R and/or R'.
  • Behenyl alcohol could be used in a commercial available technical grade, which means that it is not a pure linear C22-alcohol, but a blend of CI 8-, C20- and C22-alcohols, with the majority (by weight) of C22-alcohol.
  • Different monomers according to formula (I) could be present in the inventive polymers.
  • Preferred are those co-polymers comprising of a first monomer according to formula (I), and a second monomer which is structural different to said first monomer, preferably fumaric acid.
  • the term "structural different” in this regard mean that the second monomer will not fall within the definition of Markush formula (I).
  • Preferred are polymers, where 40 to 100 mol %, and more advantageous of 70 to 100 mol % of all monomers are selected from those monomers according to formula (I), and it is then preferred to select those monomers according to formula (I) where R and/or R' represent a C-22 alkyl group, preferably a linear one.
  • the monomers up to 100 mol % then are selected from different compounds comprising unsaturated moieties, whereby unsaturated dibasic carboxylic acids, like fumaric acid could be preferred monomers.
  • the polymers used as thickener according to the present invention can be obtained according to the standards method known in organic chemistry. Esterification of the fumaric acid with the corresponding alcohol can be done by known methods in the art for example, by using / oluene sulfonic acids. Typically, the polymerization is initiated by a radical starter, for example a persulfate. It is possible, to prepare the esters in a first step followed by polymerization or vice versa, that means first preparing the polymeric backbone and than esterifying the polymer thus obtained.
  • the polymers according to the present invention show a preferred weight average molecular weight in the range of about 3,000 - 300,000 Da and preferably between 25,000 - 200,000 Da and most preferred between 60,000 - 100,000 Da.
  • a further embodiment of the invention is therefore directed to the use of the polymers as described above as thickening agent for the preparation of or for the use in cosmetic compositions.
  • Thickening in the sense of the present technical teaching encompasses any increasing of the viscosity of a given oil-phase after the polymer has been added, compared to the viscosity, measured without this additive, according to the same methods, and with the same equipment at the same physical conditions (temperature, air pressure, humidity etc.).
  • the polymers in the sense of this invention could be used as thickening agent for incorporation in all kind of cosmetic preparations, whereby oils as well as any kind of emulsions with water and oil are possible products.
  • the inventive polymers could also be used in aqueous dispersions.
  • Preferred oily products are for example body care and cleansing preparations, in particular body oils, baby oil, body milk, massage oils, shower oils, antiperspirants and deodorants, sun protection oils, creams, or lotions.
  • Preferred emulsions are water-in-oil emulsions.
  • the polymers in the sense of this invention could be used in decorative cosmetic products like lip sticks, lip gloss and the like.
  • the ready made compositions, containing the polymers according to the present invention may be applied as a care component to tissues, papers, wipes, nonwovens, sponges, puffs, plasters and bandages which are used in the field of hygiene and care (wet wipes for baby hygiene and baby care, cleaning wipes, facial wipes, skin care wipes, care wipes containing active ingredients against ageing of the skin, wipes containing sun protection formulations and insect repellents and wipes for decorative cosmetics or for after-sun treatment, toilet wipes, antiperspirant wipes, diapers, handkerchiefs, wet wipes, hygiene products, self-tanning wipes). They may also be used inter alia in hair-care, hair-cleaning or hair-colouring compositions.
  • They may furthermore also be used in decorative cosmetics, such as lipsticks, lipglosses, foundations, make-up, pressed and loose powders, eye-shadow, mascaras and the like.
  • One embodiment of the present invention is therefore directed to the use of the polymers as defined above in cosmetic compositions comprising any cosmetic acceptable oil phase, in amounts from 0.1 to 10 % by weight, and preferably from 0.5 to 8.0 % by weight or 1.0 to 6.0 % by weight and particularly preferred in the range between 1.5 and 3.0 % by weight (calculated on the total weight of the cosmetic composition).
  • Those preferred cosmetic composition may be present as oils or as water containing emulsions, and most preferred as W/O emulsions.
  • the amount of the polymer is in a preferred embodiment selected from 0.1 to 6.0 % by weight, and more advantageously from 0.5 to 3.0 % by weight, calculated on the total weight of the emulsion.
  • the cosmetic compositions contain besides the above describes polymers as thickeners a number of other auxiliaries and additives such as, for example, consistency factors, superfatting agents, stabilizers, polymers, pH-adjusting agents, phospholipids, biogenic agents, antioxidants, deodorants, antiperspirants, antidandruff agents, film formers, swelling agents, insect repellents, self-tanning agents, tyrosinase inhibitors (depigmenting agents), fillers, hydrotropes, solubilizers, preservatives, perfume oils, dyes, UV-filters etc.
  • the compositions where the polymeric thickening agents of the present invention are used are preferably free of any biocides.
  • a further advantage in using the above mentioned polymers is an enhanced ability of the thickened oils containing them to stabilize any kind of particles against separation or settlement.
  • particles could mean capsules, microcapsules, pigments, sensory modifiers, air bubbles, dispersed polymer particles and the like.
  • Fumarate dibehenyl ester is polymerized by radical polymerization at 80°C using sodium persulfate as initiator.
  • the resulting polymer has a weight average molecular weight of approx. 120.000 Da and has been tested in different application examples which are listed below.
  • other Polyfumarates have been prepared accordingly, starting with Fumarate diesters with different chain lengths of the ester groups.
  • mixtures of different fumarate diesters or of a fumarate diesters with fumaric acid have been polymerized to copolymers in the same way.
  • a polymer of fumarate dibehenyl ester has been added to various cosmetic acceptable oil phases, stirred at 80°C for 60 minutes, stored at 23°C for at least 12 hours and the viscosity was measured (if not mentioned at 23 °C ⁇ 2°C).
  • the viscosity data directly after addition of the polymer is shown, and after 2 minutes shearing.
  • the data show that the polymers are able to thicken the various oils.
  • the shear data indicate that a composition containing the polymers according to the present invention show a shear-thinning behavior, nevertheless a high viscosity is kept even under shear conditions.
  • compositions and the results of the viscosity measurement are shown in the following tables (all amounts are expressed as %-by weight). Comparison compositions are marked as CI, C2 etc.
  • Cosmetic oils and other ingredients used in the tests are as follows:
  • Example 3 Thickening of a Body Massage Oil
  • Measurement procedure Shear-rate controlled measurements are performed using a commercial rheometer (Malvern/Bohlin CVOR-120) with a 40 mm plate-plate geometry and a gap height of 1 mm, temperature is controlled by a Peltier system in the lower plate. Measurement temperatures are 14 °C, 21 °C, and 28 °C. After reaching thermal equilibrium, the sample is allowed to rest for 1200 s, and after that a shear rate ramp test (up-down) is conducted between 5 s _1 and 100 s _1 , 22 data points are collected in a measurement time of 30 s. A total of 2-3 individual measurements are conducted per sample and temperature. The viscosity values reported are averages of the data points collected at a shear rate of 100 s -1 .
  • a shear rate controlled pre-shear of 1 s "1 was applied for 15s to standardize the shear-history of the samples. This was followed by 75s of rest.
  • the actual measurement was a stress controlled ramp, ranging from shear stresses of 0.06 Pa to the maximum of 7162 Pa obtainable with the available instrument. For the complete ramp, a total of 150 data points were programmed to be recorded in logarithmic progression within 300s of total measurement time.
  • Viscosity of pure Oils (without Polymer) Pure Cetiol ® CC shows newtonian behavior with a viscosity of approx. 5 mPa s, pure Myritol ® 318 with approx. 20 mPa s.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne l'utilisation de certains polymères dérivés d'acide fumarique et d'esters d'acide fumarique pour épaissir des phases huileuses de compositions cosmétiques.
PCT/EP2010/004824 2010-08-06 2010-08-06 Agents épaississants pour phases cosmétiques huileuses WO2012016578A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/EP2010/004824 WO2012016578A1 (fr) 2010-08-06 2010-08-06 Agents épaississants pour phases cosmétiques huileuses

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PCT/EP2010/004824 WO2012016578A1 (fr) 2010-08-06 2010-08-06 Agents épaississants pour phases cosmétiques huileuses

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2803598A (en) * 1953-10-16 1957-08-20 Exxon Research Engineering Co Gamma ray polymerization of unsaturated esters
US3234134A (en) * 1962-09-07 1966-02-08 Exxon Research Engineering Co Terpolymer of an alpha, beta-unsaturated dicarboxylic acid ester, an alkylene ester and a hydroxyalkyl acrylate, and hydrocarbon oil compositions therewith
US5972356A (en) * 1997-11-05 1999-10-26 The Procter & Gamble Company Personal care compositions
US20020006419A1 (en) * 1998-09-16 2002-01-17 Raluca Lorant Emulsion comprising a hydrophilic thickening compound and a lipophilic thickening copolymer, compositions and products comprising the emulsion, and uses thereof
EP2218328A1 (fr) * 2009-02-17 2010-08-18 Cognis IP Management GmbH Compositions agrochimiques à base d'huile avec une viscosité améliorée

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2803598A (en) * 1953-10-16 1957-08-20 Exxon Research Engineering Co Gamma ray polymerization of unsaturated esters
US3234134A (en) * 1962-09-07 1966-02-08 Exxon Research Engineering Co Terpolymer of an alpha, beta-unsaturated dicarboxylic acid ester, an alkylene ester and a hydroxyalkyl acrylate, and hydrocarbon oil compositions therewith
US5972356A (en) * 1997-11-05 1999-10-26 The Procter & Gamble Company Personal care compositions
US20020006419A1 (en) * 1998-09-16 2002-01-17 Raluca Lorant Emulsion comprising a hydrophilic thickening compound and a lipophilic thickening copolymer, compositions and products comprising the emulsion, and uses thereof
EP2218328A1 (fr) * 2009-02-17 2010-08-18 Cognis IP Management GmbH Compositions agrochimiques à base d'huile avec une viscosité améliorée

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 25 January 1960 (1960-01-25), PENG, HONG-YUN; QI, GUO-RONG: "Synthesis of n-dibehenyl fumarate-vinyl acetate copolymers and their effects on pour point depression and viscosity reduction", XP002634269, Database accession no. 136:169955 *
PENG, HONG-YUN; QI, GUO-RONG: "Synthesis of n-dibehenyl fumarate-vinyl acetate copolymers and their effects on pour point depression and viscosity reduction", ZHEJIANG DAXUE XUEBAO, LIXUEBAN, vol. 28, no. 3, 2001, pages 284 - 288 *

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