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WO2018141405A1 - Émulsions contenant des siloxanes à fonction acide aminé - Google Patents

Émulsions contenant des siloxanes à fonction acide aminé Download PDF

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Publication number
WO2018141405A1
WO2018141405A1 PCT/EP2017/052426 EP2017052426W WO2018141405A1 WO 2018141405 A1 WO2018141405 A1 WO 2018141405A1 EP 2017052426 W EP2017052426 W EP 2017052426W WO 2018141405 A1 WO2018141405 A1 WO 2018141405A1
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WO
WIPO (PCT)
Prior art keywords
hydrogen
groups
weight
parts
group
Prior art date
Application number
PCT/EP2017/052426
Other languages
German (de)
English (en)
Inventor
Elke Fritz-Langhals
Richard Weidner
Sotirios KNEISSL
Original Assignee
Wacker Chemie Ag
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 Wacker Chemie Ag filed Critical Wacker Chemie Ag
Priority to PCT/EP2017/052426 priority Critical patent/WO2018141405A1/fr
Publication of WO2018141405A1 publication Critical patent/WO2018141405A1/fr

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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
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A61K8/064—Water-in-oil emulsions, e.g. Water-in-silicone 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
    • A61K8/585—Organosilicon compounds
    • 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
    • A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
    • A61K8/898—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • 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
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/48—Thickener, Thickening system

Definitions

  • the invention relates to emulsions containing amino acid functional siloxanes.
  • Emulsions play an important role in the art. They consist of two immiscible phases, an oil and a water phase. In order to achieve a stable finely divided distribution of the two phases, emulsifiers are used.
  • thickening agents include e.g. pectins,
  • Cellulose ethers Polyvinyl alcohol and silicates.
  • Emulsions of high water content are of particular interest in the art.
  • the active ingredients contained in the oil phase can then be applied more uniformly and thus often more sparingly due to the high dilution.
  • Silicone-based thickening emulsifiers are of particular interest because these polymers are very stable and chemically inert.
  • Emulsions containing amine-functional silicones in combination with acetic acid are known.
  • EP 0442098 A2 describes organopolysiloxane emulsions which comprise siloxanes containing ammonium acetate groups, an emulsifier and water. These are from
  • Acetic acid can increase the pH. This is particularly disadvantageous in cosmetic applications. In addition, the effect is limited to a narrow pH range.
  • Amino acid-functional siloxanes have also been used in emulsions, but no formulations are known which lead to thickened emulsions.
  • DE 10036532 A1 describes the formulation of 0.13 parts by weight of a sarcosine-functional siloxane in 100 parts by weight of water in the presence of 0.42 parts by weight of a detergent, which, however, is a solution.
  • EP 2231753 describes emulsions which in each case contain from 42 to 45 parts by weight of amino acid-functional siloxane and from 10 to 12 parts by weight of non-silicone-based emulsifiers in 100 parts by weight of water.
  • the object of the present invention is to provide thickened emulsions using silicones containing small amounts of amino acid moieties.
  • the invention relates to thickened emulsions containing
  • Silicone polymer (P) can be prepared based on the amount of water strongly thickened emulsions. The reduction in the proportion of amino acid-modified silicone means a significant increase in efficiency, resulting in new applications.
  • the silicone polymer (P) preferably contains at least one siloxane unit of the general formula I and no or at least one unit of the general formula II
  • R 1 and R 2 are independently hydrogen or a straight, branched or cyclic saturated or unsatu- rated alkyl group having 1 to 20 carbon atoms or aryl group or aralkyl group, wherein individual non-adjacent methylene units by groups -O-, -CO-, -COO -, -OCO- or -OCOO-, -S- or NR X or by an oxyalkylene group of the general formula (-O-CH 2 -CHR 3 -) d may be replaced, R 3 is hydrogen or alkyl,
  • R x is hydrogen or a C 1 -C 10 -hydrocarbon radical which is unsubstituted or substituted by substituents selected from -CN and halogen,
  • X is a radical of the general formula which carries at least one amino acid unit and is bonded via a carbon atom to the silicon atom
  • M is hydrogen, metal or an ammonium radical NR 10 4 + ,
  • R 10 are independently hydrogen or C 1 -C 12 alkyl, aryl or aralkyl,
  • R 4 is hydrogen or a linear, branched or cyclic saturated or unsaturated alkyl group having 1 to 20 C atoms or aryl group or aralkyl group, with individual non-adjacent methylene units being represented by groups -O-, -CO-, -COO-, -OCO- or - OCOO-, -S- or NR X or may be replaced by an oxyalkylene group of the general formula (-O-CH 2 -CHR 3 -) d ,
  • R 5 and R 6 are independently hydrogen or linear
  • branched or cyclic saturated or unsaturated alkyl groups having 1 to 20 C atoms or aryl groups or aralkyl groups, wherein individual non-adjacent methylene units represented by groups -O-, -CO-, -COO-, -OCO- or -OCOO-, -S- or NR X may be replaced, where R 5 or R 6 may be connected to R 4 ,
  • Y is a carbon atom to the organosilicon bond, linear, branched, cyclic, saturated or mono- or polyunsaturated C associated x to C 1 oo alkylene radical may be replaced in the individual carbon atoms are replaced by oxygen, nitrogen or sulfur atoms, and with non-adjacent hydroxyl groups may be substituted, mean
  • a 0, 1, 2 or 3
  • c 1, 2 or 3
  • e have integer values 0 to 50.
  • Carboxylic acid groups may be present as a free carboxylic acid or as a carboxylate salt or as mixtures of these.
  • the amino moiety may be present both as a free amino group or in protonated form as an ammonium moiety or as a mixture thereof.
  • R 1 and R 2 independently of one another preferably denote hydrogen or an unbranched, branched or cyclic saturated or unsaturated alkyl group having 1 to 6 C atoms or a benzyl or phenyl group, where non-adjacent methylene units may be replaced by nitrogen atoms or oxygen atoms, or by a Oxyalkylene group of the general formula (-O-CH 2 -CHR 3 -) d may be replaced.
  • radicals R 3 mean hydrogen or
  • Methyl especially methyl.
  • R x is preferably hydrogen or an unsubstituted C 1 -C 6 -hydrocarbon radical.
  • M is alkali metal or alkaline earth metal
  • alkali metal particularly particularly preferably sodium or potassium, or an ammonium radical.
  • R 10 preferably denotes hydrogen or C 1 -C 4 -alkyl, in particular methyl, ethyl, n-propyl.
  • R 4 is preferably hydrogen or a linear, branched or cyclic saturated or unsaturated alkyl group having 1 to 10 carbon atoms or a benzyl or phenyl group, wherein non-adjacent methylene units may be replaced by nitrogen atoms or oxygen atoms, or by a Oxyalkylene group of the general formula (-O-CH 2 -CHR 3 -) d .
  • R 4 particularly preferably represents a C 1 -C e alkyl group, wherein methylene units by oxyalkylene groups of the general
  • Formula -O- (CH 2 -CHR 3 -) d may be replaced, in particular methyl.
  • the radicals R 3 mean hydrogen or
  • Methyl especially methyl.
  • R 5 is hydrogen and R 6 is hydrogen or a linear, branched or cyclic saturated or unsaturated alkyl group having 1 to 10 carbon atoms or aryl group, or
  • Aralkyl group wherein individual non-adjacent methylene units may be replaced by groups -O-, -CO-, -COO-, -OCO- or -OCOO-, -S- or NR X.
  • R 5 is hydrogen and R 6 is -CH 2 -OH, -CH 2 -CH 2 -OH, -CHOH-CH 3 , -CH 2 -SS-CH 2 -CH (NH 2 ) COOH, -CH 2 -CH 2 -CONH 2 , -CH 2 CONH 2 , CH 2 -CH 2 -COOH, CH 2 -COOH, -CH 2 -CH 2 -CH 2 -NH-CO-NH 2 , -CH 2 -CH 2 -CH 2 -CH 2 -NH 2 , -CH 2 -CH 2 -CH 2 -NH 2 , -CH 2 -CH 2 -CH 2 -NH 2 , -CH 2 -CH 2 -CH
  • R 4 When R 4 is connected to R 5 or to R 6 , the radicals are preferably linked via an alkylene radical, in particular with 1 to 6 carbon atoms.
  • Y is preferably a linear or branched, saturated C 1 to C 20 alkylene radical in which individual carbon atoms may be replaced by oxygen, nitrogen or sulfur atoms.
  • Y is particularly preferably a grouping
  • Z is a via a carbon atom to the Organosili- ciumharm linked linear, branched, cyclic, saturated or mono- or polyunsaturated C 1 to C 100 Alkylene radical in which individual carbon atoms may be replaced by oxygen atoms.
  • Z particularly preferably denotes an oxyalkylene radical of the general formula
  • radicals R 11 independently of one another are hydrogen or alkyl, in particular methyl, and f is a value of 0 to 100, preferably 0 to 50 and more preferably 0 assumes.
  • radicals R 7 , R 8 and R 9 independently of one another preferably denote hydrogen or a linear C 1 to C 6 alkyl group, particularly preferably hydrogen or a linear C 1 to C 3 alkyl group.
  • the radicals R 8 and R 9 may also be connected to one another via alkylene radicals or oxygen and to the Z grouping.
  • d and f are each independently of one another preferably 0 to 50, particularly preferably 0 to 10, particularly preferably 0 to 5 and very particularly preferably the values 0 to 3.
  • e is preferably 0 to 10, particularly preferably 0 to 5 and very particularly preferably 0 to 3.
  • the liquid (F) is preferably an organic liquid which is liquid at 20 ° C and 0.1 MPa.
  • the compounds (V) contained in the liquid (F) are preferably selected from siloxanes, ethers, esters, amines,
  • the compounds (V) are liquid at 20 ° C and 0.1 MPa.
  • the siloxanes are linear, branched or cyclic siloxanes or mixtures thereof.
  • linear siloxanes examples include hexamethyldisiloxane,
  • Octamethyltrisiloxane decamethyltetrasiloxane, their higher homologs and mixtures thereof.
  • Examples of cyclic siloxanes are hexamethylcyclotrisiloxane (D3), octamethylcyclotetrasiloxane (D4) and decamethylcyclopentasiloxane (D6), their higher homologs and mixtures thereof.
  • Examples of branched siloxanes are Me 3 Si-O-SiMe (OSiMe 3 ) -O-SiMe 3 and (Me 3 SiO) 4 Si.
  • ethers are methyl tert. butyl ether, diethyl ether, diphenyl ether, diisopropyl ether, tetrahydrofuran, dioxane and ethylene glycol diethyl ether.
  • esters are ethyl acetate and butyl acetate.
  • amines examples are triethylamine and tributylamine.
  • nitriles examples include acetonitrile, propionitrile, butyronitrile and benzonitrile.
  • the hydrocarbons may be linear, branched, cyclic, aliphatic or aromatic.
  • hydrocarbons examples include pentane, hexane, heptane and their higher homologues, 2-methylpentane, cyclohexane,
  • Methylcyclohexane, toluene, dimethylbenzene, cumene, fcert-butylbenzene and chlorobenzene contain based on 100
  • the emulsions contain, based on 100 parts by weight of water (W), at least 0.1 part by weight and at most 10 parts by weight of a silicone polymer (P) containing amino acid moieties and at least 2 parts by weight and at most 20 parts by weight of the liquid (F).
  • W water
  • P silicone polymer
  • the silicone polymers (P) used in the emulsions can be prepared in a manner known to those skilled in the art. For example, the following reactions can be used for the attachment of the amino acids:
  • Amino group may be bound to two silicone radicals. If an amino acid contains more than one basic nitrogen-containing group, it can react in the same way so that a maximum of 2 siloxane residues per amino group present can be bound.
  • the arrangement of the siloxane or the amino acid units to each other can be different, as in the
  • the emulsions may contain other polymers. These may form homogeneous or inhomogeneous mixtures, they may be covalently bound or not bound to the polymer (P)
  • the emulsions contain these further polymers preferably in proportions of at least 0.01 and at most 50 parts by weight, more preferably in amounts of at least 0.1 and
  • the silicone-containing polymer (P) may contain blocks of siloxane units of the general formula I and none or at least one unit of the general formula II and organic blocks through which the blocks of siloxane units
  • organic blocks may be linked to the blocks of siloxane units, for example via urea moieties, urethane moieties or ester groups.
  • the proportion of organic blocks is preferred
  • the emulsions may contain further substances which are present either as solids or dissolved.
  • solids for example, highly disperse silica, silicates or zeolites or inorganic and organic salts, for example NaCl, ammonium chloride, potassium chloride in proportions of preferably at least 0.01 wt .-% to at most 30 wt .-%, particularly preferably 0.1 wt. % to a maximum of 10% by weight,
  • the silicone-containing polymer (P) is used to prepare the silicone-containing polymer (P)
  • Emulsion preferably dissolved in the liquid (F) or
  • water is added and water is then added in several steps and the mixture is mechanically agitated, e.g. by stirring or shaking.
  • the emulsions according to the invention are preferably added
  • Another object of the invention is the use of the emulsions.
  • the emulsions are preferably used in cosmetic
  • Hydrous samples (pseudoplastic): Cones: CP25-1 / TG (25mm width, 1 degree and true gap surface)
  • siloxane (P) and liquid (F) given in Table 1 are each based on 100 parts by weight of water.
  • silicone oil DM2 linear oligodimethylsiloxane having an average chain length of 5 and a viscosity of about 2 ⁇ s.
  • Viscosity values as a function of the composition of the sample at two different shear rates ⁇ are a function of the composition of the sample at two different shear rates ⁇ .
  • siloxane (P) and liquid (F) given in Table 2 are each based on 100 parts by weight of water.
  • ⁇ , ⁇ -Glu-Na, n 54: prepared analogously with glutamic acid disodium salt
  • the amino acid-functional siloxanes (P) were dissolved or suspended in the liquid (F), and the mixture was then added with water in portions with stirring or shaking. This formed an emulsion, which at high
  • Stable emulsions whose composition is listed in Table 3 were prepared from the siloxanes containing amino acid moieties.
  • Table 3 Manufactured stable emulsions, parts by weight of components P and F based on 100 parts by weight of water. Abbreviations:
  • HMDS hexamethyldisiloxane
  • DM2 linear oligodimethylsiloxane with an average chain length of 5 and one

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

Abstract

L'invention concerne des émulsions épaissies contenant 1) 100 parties en poids d'eau (W), 2) au maximum 20 parties en poids d'un polymère de silicone (P) contenant des groupements d'acides aminés, 3) au maximum 30 parties en poids d'un liquide (F) constitué d'un ou de plusieurs composés (V), le liquide (F) présentant une lacune de miscibilité avec l'eau (W).
PCT/EP2017/052426 2017-02-03 2017-02-03 Émulsions contenant des siloxanes à fonction acide aminé WO2018141405A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/EP2017/052426 WO2018141405A1 (fr) 2017-02-03 2017-02-03 Émulsions contenant des siloxanes à fonction acide aminé

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/EP2017/052426 WO2018141405A1 (fr) 2017-02-03 2017-02-03 Émulsions contenant des siloxanes à fonction acide aminé

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WO2018141405A1 true WO2018141405A1 (fr) 2018-08-09

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0442098A2 (fr) 1990-02-16 1991-08-21 Wacker-Chemie Gmbh Procédé de préparation d'emulsions d'organopolysiloxanes à particules fines
DE10036532A1 (de) 2000-07-27 2002-02-21 Ge Bayer Silicones Gmbh & Co alpha.w-aminosäurefunktionalisierte Polysiloxane
WO2009084711A1 (fr) * 2007-12-27 2009-07-09 Dow Corning Toray Co., Ltd. Procédé de fabrication d'émulsions d'organopolysiloxane modifié par acide aminé
EP2826806A1 (fr) * 2013-07-18 2015-01-21 Evonik Industries AG Nouveau siloxane à acides aminés modifiés, son procédé de fabrication et son utilisation

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0442098A2 (fr) 1990-02-16 1991-08-21 Wacker-Chemie Gmbh Procédé de préparation d'emulsions d'organopolysiloxanes à particules fines
DE10036532A1 (de) 2000-07-27 2002-02-21 Ge Bayer Silicones Gmbh & Co alpha.w-aminosäurefunktionalisierte Polysiloxane
WO2009084711A1 (fr) * 2007-12-27 2009-07-09 Dow Corning Toray Co., Ltd. Procédé de fabrication d'émulsions d'organopolysiloxane modifié par acide aminé
EP2231753A1 (fr) 2007-12-27 2010-09-29 Dow Corning Toray Co., Ltd. Procédé de fabrication d'émulsions d'organopolysiloxane modifié par acide aminé
EP2826806A1 (fr) * 2013-07-18 2015-01-21 Evonik Industries AG Nouveau siloxane à acides aminés modifiés, son procédé de fabrication et son utilisation

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