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WO2002062311A1 - Preparation cosmetique pour le soin de la peau a silicone dispersee de haute viscosite presentant une petite taille de gouttelettes - Google Patents

Preparation cosmetique pour le soin de la peau a silicone dispersee de haute viscosite presentant une petite taille de gouttelettes Download PDF

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Publication number
WO2002062311A1
WO2002062311A1 PCT/EP2002/001035 EP0201035W WO02062311A1 WO 2002062311 A1 WO2002062311 A1 WO 2002062311A1 EP 0201035 W EP0201035 W EP 0201035W WO 02062311 A1 WO02062311 A1 WO 02062311A1
Authority
WO
WIPO (PCT)
Prior art keywords
silicone
skin care
group
droplet size
viscosity
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/EP2002/001035
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English (en)
Inventor
Anne-Lise Girboux
Isabelle Van Reeth
Leon Andre Marteaux
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.)
Dow Silicones Belgium SPRL
Dow Silicones Corp
Original Assignee
Dow Corning SA
Dow Corning Corp
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 Dow Corning SA, Dow Corning Corp filed Critical Dow Corning SA
Publication of WO2002062311A1 publication Critical patent/WO2002062311A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • A61Q19/10—Washing or bathing 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
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A61K8/062—Oil-in-water emulsions
    • 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
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/21—Emulsions characterized by droplet sizes below 1 micron

Definitions

  • the present invention relates to use of certain silicone-in-water emulsions in a cosmetic skin care 5 preparation, for example a shower gel or facial cleanser.
  • Silicone-in-water emulsions are well known for use in skin care preparations, see for example EP 0874017, EP 0893467, and EP 1013700. Silicone is lubricious, and improves the properties of skin care preparations by 0 improving the feel of skin when deposited thereon.
  • EP0874017 refers to how the silicone-in-water emulsions disclosed therein are useable in personal care applications.
  • cosmetic skin care preparations which can provide still further improved 5 sensory performance when applied to skin, and at ever lower silicone concentrations. This could for example be improved by ensuring a larger proportion of the silicone is deposited on the skin.
  • the preferred silicone emulsions used have to have a silicone 0 viscosity range from 1. lO ⁇ mm ⁇ s-! to 1. lO ⁇ m ⁇ s--'- and a particle size of from 1 to 100 ⁇ n. It has now surprisingly been found that if the viscosity of the silicone is raised higher and is used in combination with a particle size below l ⁇ m, better deposition can be achieved, without any loss of 5 essential properties of skin care compositions are experienced.
  • a silicone-in-water emulsion in a cosmetic skin care preparation, wherein the dispersed 0 silicone has a viscosity of at least, and preferably more than 100 million mirths--'-, and a droplet size of at most, preferably less than I ⁇ m. (Herein all viscosities are measured at 25 a C and atmospheric pressure).
  • Use of the above defined silicone-in-water emulsion in cosmetic skin care preparations according to the present invention can provide cosmetic skin care preparations which have improved foam generation, quality and/or quantity compared to conventional preparations, and improved sensory perception for the user, including improved cushion and wet feel, tackiness, smoothness, and/or suppleness of skin to which the preparation is applied.
  • the amount of silicone required to achieve these results can surprisingly be lower than in conventional preparations, as the silicone is perceived by the user on the skin at lower active levels.
  • a cosmetic skin care preparation which comprises a silicone-in-water emulsion, wherein the dispersed silicone has a viscosity of at least, preferably greater than 100 million mm ⁇ s--'-, and a particle size of at most, preferably less than l ⁇ m.
  • the silicone-in-water emulsion used in the present invention may be prepared by the method disclosed in EP 0874017, which publication is incorporated herein by reference.
  • this method comprises a) mixing materials comprising a composition containing at least one polysiloxane, at least one organosilicon material which reacts with said polysiloxane by a chain extension reaction, a metal containing catalyst for said chain extension reaction, at least one surfactant, and water to form a mixture, and b) emulsifying the mixture.
  • This method provides a route to silicone-in-water emulsions having a wide range of physical characteristics, in particular emulsions wherein the dispersed silicone has a high viscosity and low droplet size.
  • Chain extension reactions with polysiloxanes are known in the art and can involve, for instance, the hydrosilylation reaction in which an Si-H reacts with an aliphatically unsaturated group in the presence of a platinum or rhodium-containing catalyst.
  • the reaction can involve the reaction of an Si-OH group (e.g. a hydroxy-terminated polysiloxane) with an alkoxy group (e.g. alkoxysilanes, silicates or alkoxysiloxanes) in the presence of a metal containing catalyst.
  • the polysiloxane (s) used in the chain extension reactions described above generally comprises a substantially linear polymer of the structure:
  • each R independently represent a hydrocarbon group having up to 20 carbon atoms such as an alkyl group (e.g., methyl, ethyl, propyl or butyl), an aryl group (e.g., phenyl) , or the group required for the chain extension reaction described above ("reactive group", e.g., hydrogens, aliphatically unsaturated groups such as vinyl, allyl or hexenyl, hydroxy, alkoxy such as methoxy, ethoxy or propoxy, alkoxy-alkoxy, acetoxy, amino and the like) , provided that on average there is between one and two reactive groups (inclusive) per polymer, and ⁇ is a positive integer greater than one.
  • a majority, more preferably >90%, and most preferably >98% of the reactive groups are end-groups .
  • n is an integer which results in polysiloxanes with viscosities between about 1 and about 1 million mm ⁇ s-!.
  • the polysiloxane (I) can have a small amount of branching (e.g., less than 2 mole % of the siloxane units) without affecting the invention, i.e., the polymers are w substantially linear" .
  • the R groups can be substituted with, for example, nitrogen containing groups (e.g., amino groups), epoxy groups, sulphur containing groups, silicon containing groups, oxygen containing groups and the like.
  • the organosilicon material which reacts with the polysiloxane by a chain extension reaction can be either a second polysiloxane or a material which acts as a chain extension agent. If the organosilicon material is a polysiloxane then it too will generally have the structure described above (I) . In such a situation one polysiloxane in the reaction will comprise one reactive group and the second polysiloxane will comprise a second reactive group which reacts with the first.
  • the organosilicon material comprises a chain extension agent
  • it can be a material such as a silane, a siloxane (e.g., disiloxane or trisiloxane) or a silazane.
  • a composition comprising a polysiloxane according to the above structure (I) which has at least one Si-OH group can be chain extended by using an alkoxysilane (e.g., a dialkoxysilane or trialkoxysilane) in the presence of a tin or titanium containing catalyst.
  • the metal containing catalysts used in the above described chain extension reactions are often specific to the particular reaction. Such catalysts, however, are known in the art.
  • a polysiloxane having at least one aliphatically unsaturated group, preferably an end group is reacted with an organosilicon material which is a siloxane or a polysiloxane having at least one Si-H group, preferably an end group, in the presence of a hydrosilylation catalyst.
  • the polysiloxane having at least one aliphatically unsaturated group has the structure (I) wherein R and n axe as defined above and provided that on average between one and two (inclusive) R groups comprise an aliphatically unsaturated group per polymer.
  • the organosilicon material having at least one Si-H group preferably has the above structure (I) wherein R and n are as defined above and provided that on average between one and two (inclusive) R groups comprise hydrogen atoms and ⁇ is 0 or a positive integer.
  • This material can be a polymer or a lower molecular weight material such as a siloxane (e.g. a disiloxane or a trisiloxane) .
  • a hydrosilylation catalyst are known in the art and include, for example, platinum and rhodium- containing materials.
  • catalysts may take any of the known forms, such as platinum or rhodium deposited on carriers such as silica gel or powdered charcoal, or other appropriate compounds such as platinic chloride, salts of platinum and chloroplatinic acids.
  • a preferred material is chloroplatinic acid either as the commonly obtainable hexahydrate or the anhydrous form because of its easy dispersibility in organosilicon systems and its non-effect on colour of the mixture.
  • Platinum or rhodium complexes may also be used, for example those prepared from chloroplatinic acid hexahydrate and divinyltetramethyldisiloxane. Generally, these catalysts are used in amounts of between about 0.0001 and 10 wt .
  • a polysiloxane having at least one Si-OH group preferably an end group
  • an organosilicon material having at least one alkoxy group preferably a siloxane having at least one Si-OR group, or an alkoxysilane having at least two alkoxy groups in the presence of a metal containing catalyst.
  • the polysiloxane having at least one SiOH group has the structure (I) wherein R and n are as defined above and on average between one and two (inclusive) R ⁇ giffoupssKComprise a hydroxyl group (OH) .
  • the organosilicon at least one alkoxy group can have the str-uctlr ⁇ t-r) wherein R and n are as defined- above and on average between one and two (inclusive) R groups comprise alkoxy groups, e.g., of the structure (OR) in which R is as defined above and n is 0 or a positive integer.
  • the organosilicon material can be a silane of the structure R m Si (OR) 4 _ m , wherein R is as defined above and m is 0 to 2.
  • Other materials containing the alkoxy group e.g., alkoxy- alkoxy may also be used.
  • metal catalysts for the reaction of an Si-OH group with an Si-OR group are known in the art and may be employed including, for example, organic metal compounds such as organotin salts, titanates, or titanium chelates or complexes.
  • Examples include stannous octoate, dibutyltin dilaurate, dibutyltin diacetate, dimethyltin dineodecanoate, dibutyltin di ethoxide, isobutyl tin triceroate, dimethyltin dibutyrate, dimethyltin dineodecanoate, triethyltin tartrate, tin oleate, tin naphthenate, tin butyrate, tin acetate, tin benzoate, tin sebacate, tin succinate, tetrabutyl titanate, tetraisopropyl titante, tetraphenyl titante, tetraoctadecyl titanate, titanium naphthanate, ethyltriethanolamine titante, titanium diiso-propyl diethyl acetoacetate, titanium diisopropoxy diacetyl aceton
  • these catalysts are used in amounts of between about 0.001 and 10 wt. % based on the weight of the composition (I) .
  • any composition containing at least one polysiloxane, at least one organosilicon material which reacts with said polysiloxane by a chain extension reaction, and a metal containing catalyst for said chain extension reaction can be used for the chain extension reaction.
  • the mixture used to form the emulsion also contains at least one surfactant. This can be a non-ionic surfactant, a cationic surfactant, an anionic surfactant, alkylpolysaccharides, amphoteric surfactants and the like.
  • non-ionic surfactants include polyoxyalkylene alkyl ethers, polyoxyalkeylene sorbitan alkyl esters, polyoxyalkylene alkyl esters, and polyoxyalkylene alkylphenol ethers, polyethylene glycols, polypropylene glycols, and diethylene glycols.
  • cationic surfactants include quaternary ammonium hydroxides such as tetramethylammonium hydroxide, octyltrimethylammonium hydroxide, dodecyl- trimethyl ammonium hydroxide, hexadecyltrimethyl ammonium hydroxide, octyldimethylbenzylammonium hydroxide, decyldimethylbenzyl ammonium hydroxide, didodecyldimethyl ammonium hydroxide, dioctadecyl dimethylammonium hydroxide, tallow trimethylammonium hydroxide and cocotrimethylammonium hydroxide as well as corresponding salts of these materials, fatty acid amines and amides and their derivatives and the salts of the fatty acid amines and amides including aliphatic fatty amines and their derivatives, homologs of aromatic amines having fatty chains, fatty amides derived from alipha
  • Suitable anionic surfactants include alkyl sulfates such as lauryl sulfate, polymers such as acrylates/C ⁇ o- 3 o alkyl acrylate crosspolymer alkylbenzenesulfonic acids and salts such as hexylbenzenesulfonic acid, octylbenzenesulfonic acid, decylbenzenesulfonic acid, dodecylbenzenesulfonic acid, cetylbenzenesulfonic acid and myristylbenzenesulfonic acid; the sulfate esters of monoalkyl polyoxyethylene ethers; alkylnapthylsulfonic acid; alkali metal sulforecinates, sulfonated glyceryl esters of fatty acids such as sulfonated monoglycerides of coconut oil acids, salts of sulfonated monovalent alcohol esters, amides of alkyl
  • alkylpolysaccharides include, for example, materials of the structure R- ⁇ -O- (R ⁇ O) x - (G) y wherein R-- represents a linear or branched alkyl group, a linear or branched alkenyl group or an alkylphenyl group, R2 represent an alkylene group, G represents a reduced sugar, x denotes 0 or a positive integer and y denotes a positive integer as described, for example, in US Patent 5,035,832.
  • suitable amphoteric surfactants include cocamidopropyl betaine and cocamidopropyl hydroxysulfate .
  • the above surfactants may be used individually or in combination.
  • the dispersed silicone in the emulsion used in the present invention has a viscosity of at least, preferably more than 100 million mm ⁇ s--*-, more preferably at least 150 million m ⁇ s-!, most preferably at least 170 million mm ⁇ s- ⁇ , and a droplet size of at most, preferably less than l ⁇ m, more preferably 0.5 ⁇ m or less.
  • the emulsion preferably comprises at least 50% wt . silicone, more preferably at least 60 wt . %, even more preferably 75 wt . %.
  • the emulsion is preferably incorporated in a skin care preparation in an amount which provides at least 1% silicone by weight of the skin care preparation, for example 1 to 10% by weight, (e.g. 2 to 6% wt . ) .
  • Skin care preparations are well known in the art, and typically comprise a washing base containing surfactants, and other agents for improving the cosmetic properties of the preparation.
  • the washing base typically comprises a cosmetically acceptable aqueous medium, which may be solely water, or water with a solvent (for example, a lower alcohol or alkylene glycol) .
  • the surfactants may be anionic, non- ionic, cationic or amphoteric.
  • additives which may be included in the preparation include pH adjusters (for example, amines) , viscosity regulators, electrolytes or thickeners, pearlising or opacifying agents, foam synergists, and other agents for improving the cosmetic properties of the preparation, for example anionic, non- ionic and cationic polymers, proteins, fatty acids and vitamins.
  • the cosmetic skin care preparation will typically be in the form of a thickened liquid, cream or gel.
  • the present invention will now be illustrated by way of example. All parts are parts and percentages are by weight .
  • Example 1 Various silicone-in-water emulsions having different physical properties (defined in Examples 3 to 9 below) were made according to the method described in EP 0874017, using the following components:
  • Example 2 [0033] Shower gel and facial cleanser preparations were prepared incorporating silicone-in-water emulsion prepared according to Example 1 above, each having the following formulations :
  • foam generation foam quality
  • foam quantity foam quantity
  • cushion feel wet feel
  • tackiness smoothness
  • film presence and suppleness.
  • the average rating for performance of each shower gel and facial cleanser in each category was calculated, and compared to the control preparation.
  • Example 2 Three silicone-in-water emulsions were prepared according to Example 1 above, a first having a silicone viscosity of 5 million mm ⁇ s--'-, a second having a silicone viscosity of 50 million mm ⁇ s--'-, and a third having a silicone viscosity of 170 million mm 2 s _ l. In each case the silicone droplet size was 0.4 ⁇ m.
  • shower gels were then prepared according to the formulation in Example 2 above, each shower gel containing 5% by weight of active silicone. The shower gels were then tested as described in Example 2 above, and the test results are given in Table 1 below.
  • Example 4 effect of silicone droplet size
  • Three silicone-in-water emulsions were prepared according to Example 1 above, a first having a silicone droplet size of 0.4 ⁇ m, a second having a silicone droplet size of 4 ⁇ m, and a third having a droplet size of 40 ⁇ m. In each case the silicone viscosity was 170 million mm 2 s ⁇ l.
  • Shower gels were then prepared according to the formulation in Example 2 above, each shower gel containing 5% by weight of active silicone. The shower gels were then tested as described in Example 2 above, and the test results are given in Table 2 below.
  • Example 3 Three silicone-in-water emulsions were prepared according to Example 1 above, with the exception that the first emulsion contained anionic surfactant sodium C ⁇ 4 _i 6 olefin sulphonate, the second contained non-ionic surfactant poly(EO) mono lauryl ether, and the third cationic surfactant hexadecyltrimethylammonium chloride.
  • the silicone droplet size was 0.4 ⁇ m and the silicone viscosity was 170 million mm s ⁇ -'-.
  • shower gels were then prepared according to the formulation in Example 2 above, each shower gel containing 5% by weight of active silicone. The shower gels were then tested as described in Example 2 above, and the test results are given in Table 3 below.
  • a silicone-in-water emulsion was prepared according to Example 1 above having a silicone droplet size of 0.4 ⁇ m and silicone viscosity was 170 million mm s--'-.
  • Three shower gels were then prepared according to the formulation in Example 2 above, the first shower gel containing 2% by weight of active silicone, the second containing 3% active silicone, and the third containing 5%. The shower gels were then tested as described in Example 2 above, and the test results are given in Table 4 below.
  • Example 7 non-ionic vs. anionic surfactant
  • the silicone-in-water emulsions were prepared according to Example 1 above, with the exception that the first contained anionic surfactant (control) , sodium C ⁇ 4 -i 6 olefin sulphonate, and the second contained non-ionic surfactant polyol (EO) mono lauryl ether. In both emulsions the silicone droplet size was 0.4 ⁇ m and silicone viscosity was 170 million mm 2 s ⁇ .
  • Two shower gels were then prepared according to the formulation in Example 2 above with 5 % silicone active level. The shower gels were then tested as described in Example 2 labove, using the anionic surfactant containing _showejr gel _as the control, and the test results are given in Table 5 below.
  • Example 8 FTIR measurement of skin deposition
  • silicone-in-water emulsions were prepared according to Example 1 above, two having a silicone viscosity of 170 million mm 2 s-l, and two having a silicone viscosity of 5 million mm 2 s -1 .
  • one emulsion had a silicone droplet size of 0.5 ⁇ m, and the other a silicone droplet size of 40 ⁇ m.
  • Four shower gels were then prepared according to the formulation in Example 2 above. FTIR measurements were made to determine the amount of silicone deposition on their skin by the following procedure. An IR scan of the forearm of each test subject was made to establish a control value.
  • a silicone-in-water emulsion were prepared according to Example 1 above, having a silicone viscosity of
  • Example 2 170 million mm 2 s ⁇ -'- and a silicone droplet size of 0.4 ⁇ m.
  • a facial cleanser was then prepared according to the formulation in Example 2 above, together with a control cleanser (containing no silicone) for comparison.
  • the facial cleanser was then tested as described in Example 2 above, and the test results are given in Table 7 below.

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Abstract

L'invention concerne l'utilisation d'une émulsion de silicone dans de l'eau, contenue dans une préparation cosmétique pour le soin de la peau, dans laquelle la silicone dispersée présente une viscosité au moins, de préférence, supérieure à 100 millions mm2s-1, et une taille de gouttelettes au moins, de préférence, inférieure à 1νm. L'invention concerne également une préparation cosmétique pour le soin de la peau qui contient une émulsion de silicone dans de l'eau, telle que décrite précédemment.
PCT/EP2002/001035 2001-02-02 2002-01-29 Preparation cosmetique pour le soin de la peau a silicone dispersee de haute viscosite presentant une petite taille de gouttelettes Ceased WO2002062311A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0102647.5 2001-02-02
GBGB0102647.5A GB0102647D0 (en) 2001-02-02 2001-02-02 Cosmetic skin care preparation

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WO2002062311A1 true WO2002062311A1 (fr) 2002-08-15

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PCT/EP2002/001035 Ceased WO2002062311A1 (fr) 2001-02-02 2002-01-29 Preparation cosmetique pour le soin de la peau a silicone dispersee de haute viscosite presentant une petite taille de gouttelettes

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004024114A3 (fr) * 2002-09-10 2004-06-10 Takasago Perfumery Co Ltd Compositions comportant des emulsions aqueuses de silicone et produits parfumes et de soins capillaires comprenant de telles compositions
US9198849B2 (en) 2013-07-03 2015-12-01 The Procter & Gamble Company Shampoo composition comprising low viscosity emulsified silicone polymers
US10363211B2 (en) 2013-09-27 2019-07-30 The Procter And Gamble Company Hair conditioning compositions comprising low viscosity emulsified silicone polymers

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0874017A2 (fr) * 1997-04-23 1998-10-28 Dow Corning S.A. Procédé de préparation d'émulsions aqueuses de silicone
EP1013700A2 (fr) * 1998-12-02 2000-06-28 Dow Corning S.A. Procédé de préparation d'émulsions à base de silicone du type huile dans l'eau
EP1108416A1 (fr) * 1999-10-20 2001-06-20 L'oreal Compositions cosmétiques contenant un copolymère vinyldiméthicone/diméthicone en émulsion aqueuse et un épaississant associatif et leurs utilisations

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0874017A2 (fr) * 1997-04-23 1998-10-28 Dow Corning S.A. Procédé de préparation d'émulsions aqueuses de silicone
EP1013700A2 (fr) * 1998-12-02 2000-06-28 Dow Corning S.A. Procédé de préparation d'émulsions à base de silicone du type huile dans l'eau
EP1108416A1 (fr) * 1999-10-20 2001-06-20 L'oreal Compositions cosmétiques contenant un copolymère vinyldiméthicone/diméthicone en émulsion aqueuse et un épaississant associatif et leurs utilisations

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004024114A3 (fr) * 2002-09-10 2004-06-10 Takasago Perfumery Co Ltd Compositions comportant des emulsions aqueuses de silicone et produits parfumes et de soins capillaires comprenant de telles compositions
US9198849B2 (en) 2013-07-03 2015-12-01 The Procter & Gamble Company Shampoo composition comprising low viscosity emulsified silicone polymers
US10363211B2 (en) 2013-09-27 2019-07-30 The Procter And Gamble Company Hair conditioning compositions comprising low viscosity emulsified silicone polymers

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