EP3303452A1 - Composés d'organosilicium présentant des groupements acides aminés et procédé de production desdits composés - Google Patents

Composés d'organosilicium présentant des groupements acides aminés et procédé de production desdits composés

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Publication number
EP3303452A1
EP3303452A1 EP16726848.1A EP16726848A EP3303452A1 EP 3303452 A1 EP3303452 A1 EP 3303452A1 EP 16726848 A EP16726848 A EP 16726848A EP 3303452 A1 EP3303452 A1 EP 3303452A1
Authority
EP
European Patent Office
Prior art keywords
general formula
amino acid
group
hydrogen
groups
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.)
Withdrawn
Application number
EP16726848.1A
Other languages
German (de)
English (en)
Inventor
Elke Fritz-Langhals
Richard Weidner
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.)
Wacker Chemie AG
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
Publication of EP3303452A1 publication Critical patent/EP3303452A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/38—Polysiloxanes modified by chemical after-treatment
    • C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
    • C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/05—Alcohols; Metal alcoholates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/17—Amines; Quaternary ammonium compounds
    • C08K5/175—Amines; Quaternary ammonium compounds containing COOH-groups; Esters or salts thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups

Definitions

  • the invention relates to amino acid group-containing organosilicon compounds and a simple process for their preparation and their use.
  • Amino-containing organosilicon compounds play an important role in the art.
  • po ⁇ stellar amino group in a polysiloxane, for example, the interaction with polar surfaces, and thus the adhesion of the polysiloxane is greatly increased.
  • amino acid-functionalized Organosiliciumverbin ⁇ tions are technically highly interesting, since even higher polarity can be achieved by the additional presence of the carboxylic acid grouping.
  • Amino groups are present in the iA betaine, which electrostatic interactions are much more pronounced than in the amino group-containing organosilicon ⁇ .
  • amino acid-functionalized polysiloxanes are already known. Of particular interest, however, are amino acid-functional organosilicon compounds in which the basic character of the amino groups p réelle and consequently the amphoteric character of the amino acid moiety is retained after the linkage with the polysiloxane. This is especially the case when the amino acid is linked to the polysiloxane by addition to a reactive epoxide grouping on the polysiloxane.
  • JP 52-114699 also describes the reaction of carboxy-protected amino acids using an epoxy-functional trisiloxane.
  • EP 2826806 describes the preparation of amino acid- modified siloxanes from organic amino acid salts, in which the counterion to the carboxylation of the amino acid is an organic cation, eg a quaternary ammonium or phosphonium cation with a long-chain alkyl radical.
  • the preparation of these amino acid salts already requires two conversion ⁇ steps of: in a first step, the amino acids are in the In a second step, the reaction with the quaternary ammonium or phosphonium chloride to form potassium chloride, which can be precipitated and separated by dispersing in a suitable medium. This method is therefore both costly and expensive.
  • quaternary ammonium and phosphonium compounds are toxicologically questionable, thereby reducing the possible range of application of the compounds.
  • a great advantage would therefore be a method in which the technically available free amino acids could be used directly without prior conversion to salts. This would then also be opened up amino acid-functional organosilicon compounds containing unprotected carboxyl groups and thus show more pronounced properties of an amino acid grouping.
  • EP 2231753 describes the reaction of epoxy-functional polysiloxanes with free amino acids in an aqueous emulsion in the presence of about 25 to 28% by weight emulsifier. The mixing of the usually extremely viscous emulsions poses a high technical challenge for the
  • the formed amino acid-group-carrying siloxane always falls in admixture with emulsifiers, which can not be separated from the product due to their similar properties.
  • the amino acid-functionalized organosilicon compounds can therefore not be isolated in pure form according to this instruction. This limits the application ⁇ region of amino acid-functional polysiloxanes significantly.
  • the emulsifier components may interfere with further use or even prohibitively.
  • the invention relates to a process for the preparation of organosilicon compounds (0) containing free amino acid grouping, which comprises at least one 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 unsaturated ⁇ saturated alkyl group or alkoxy group having 1 to 20 carbon atoms, aryl or aralkyl group, wherein individual non-adjacent methylene units by groups -0-, -CO- , -COO-, -OCO- or -OCOO-, -S- or NR X or by an oxyalkylene group of the general formula (-O-CH 2 -CHR 3 -) d where d is from 1 to 100, in which the radicals R 3 are the importance
  • R x is hydrogen or an unsubstituted or ducks with substitution selected from -CN and halogen, substitu ⁇ wholesome C 1 - represents hydrocarbon radical, - C 1 0
  • X is a radical of the general formula V which carries at least one amino acid unit and is bonded via a carbon atom to the organosilicon compound
  • Y is a linear, branched, cyclic, saturated or mono- or polyunsaturated C 1 to C 100 alkylene radical bonded via a carbon atom to the organosilicon compound, in which individual carbon atoms may be replaced by oxygen, nitrogen or sulfur atoms,
  • R 4 , R 5 and R 6 independently of one another denote hydrogen or linear, branched or cyclic saturated or unsaturated C 1 to C 2 0 alkyl group, with some not being adjacent disclosed methylene units may be replaced by groups -0-, -CO-, -COO-, -OCO- or -OCOO-, -S- or NR X
  • R 7 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, wherein individual non-adjacent methylene units represented 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 where d is from 1 to 100, in which the radicals R 3 independently of one another have the meaning of hydrogen or alkyl,
  • R 8 and R 9 independently of one another are hydrogen or linear
  • Methylene units may be replaced by groups -O-, -CO-, -COO-, -OCO- or -OCOO-, -S- or NR X ,
  • R 7 can be connected to R 8 or to R 9 ,
  • a 0, 1, 2 or 3
  • e are the values 0 or 1 and
  • f have integer values from 0 to 50.
  • organosilicon compounds bearing epoxy groups can be reacted with the unprotected amino acids in the presence of alcohols to give the desired amino acid-functional organosilicon compounds (0).
  • the manufacturing process is thus simplified.
  • no emulsifier additive is necessary for the process of the invention, and thus amino acid moieties are included
  • R 1 and R 2 are hydrogen or a
  • R 1 and R 2 are the radicals methyl, ethyl, vinyl.
  • R x is hydrogen or straight, branched or cyclic saturated ver ⁇ alkyl group having 1 to 6 carbon atoms or a benzyl or phenyl group.
  • R x are hydrogen and the radicals methyl, ethyl, propyl, butyl.
  • Y represents a linear or branched, saturated C3 may be replaced in the individual carbon atoms are replaced by oxygen, nitrogen or sulfur atoms to C 20 alkylene radical.
  • Y is an oxyalkylene radical of the general formula
  • radicals R 3 independently of one another are hydrogen or alkyl, in particular methyl
  • g has a value of 0 to 100, preferably 0 to 50 and particularly preferably 0.
  • the radicals R 4 , R 5 and R 6 independently of one another preferably denote hydrogen or a linear C 1 to Ce alkyl group, especially preferably hydrogen or linear C 1 to C 3 alkyl group, in particular the radicals methyl, ethyl, propyl.
  • radicals R and R may also be connected to one another via alkylene radicals, in particular C 1 to Ce, alkylene radicals or oxygen and to the group Y.
  • R 7 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
  • R 7 particularly preferably denotes a C 1 -C 6 -alkyl group, where methylene units are denoted by oxyalkylene groups of the general formula -O- (CH 2 -CHR 3 -) d with d of 1 to 50, where the radicals R 3 independently of one another are hydrogen or methyl accept, be replaced.
  • Particularly preferred radicals R 7 are the radicals methyl, ethyl, propyl, butyl.
  • R 8 is hydrogen and R 9 is hydrogen or a linear, branched or cyclic saturated or unsaturated ⁇ saturated alkyl group having 1 to 10 carbon atoms or aryl group or aralkyl group, wherein individual non-adjacent Me ⁇ thylenechen by groups -0-, -CO- , -COO-, -OCO- or -OCOO-, -S- or NR X , in particular -CH 3 , - CH (CH 3 ) 2 , -CH 2 -CH (CH 3 ) 2 , -CH ( CH 3 ) -CH 2 -CH 3 , -CH 2 -OH, -CH 2 -CH 2 -OH, - CHOH-CH 3 , -CH 2 -SH, -CH 2 -SS-CH 2 -CH (NH 2 ) COOH, -CH 2 -CH 2 -S-CH 3, -CH 2 - CH 2 -CONH 2,
  • Epoxydüen bearing Si-bonded Gruppie ⁇ en run Z are:
  • the epoxy-carrying organosilicon compounds can - as known to the skilled worker - for example by addition of Si-H groups to olefinic groups bearing epoxides, such as allyl glycidyl ether or cyclohexadiene monoepoxide, or by epoxidation of olefinic
  • Group-carrying organosilicon compounds or be prepared by dehydrohalogenation of chlorohydrins.
  • R 7 can also be linked to R 8 or R 9 , the radicals are preferably via an alkylene radical
  • amino acid proline An example of this is the amino acid proline.
  • amino acids are:
  • Glycine Glycine, sarcosine, alanine, ß-alanine, valine, leucine, isoleucine, ⁇ -aminobutyric acid,
  • the further carboxyl groups can be used independently as free carboxyl groups or as salts, preferably metal or ammonium salts, particularly preferably as alkali metal, alkaline earth metal salts and tertiary amines, very particularly preferably as sodium or potassium salts, in the form of their esters, preferably alkyl esters, particularly preferably present as methyl esters or ethyl esters.
  • R 7 meaning hydrogen
  • the product formed in this case can react in the same way with a further Epoxydgrupptechnik.
  • products with a siloxane residue and products with two siloxane residues per amino acid molecule can arise.
  • Amino acids with other basic nitrogen-containing groups eg. As lysine, ornithine, arginine, histidine and
  • Tryptophan can react via these groups in each case once or twice with the epoxide of the organosilicon compound.
  • a maximum of one organosilicon radical can be bound per hydrogen atom to a basic nitrogen grouping of the amino acid of the general formula IV. If more than one basic nitrogen grouping is present in the amino acid of general formula IV used, regioisomeric products are generally formed.
  • S represents the organosilicon radical bonded via the respective spacer group: when reacted with an epoxide grouping:
  • the molar ratio of organosilicon compound to amino acid residue can be influenced by the molar ratio of the epoxide groups present to the amino groups of the amino acid. If, for example, a deficiency of the amino used acid, it is preferably carried out a multiple reaction with the Epoxydgrupptechniken.
  • the organosilicon compound contains more than one epoxide group
  • coupling of molecules of the organosilicon compound can occur due to the described multiple reaction of the amino group.
  • a deficiency of Ami ⁇ noklare used is preferably effected the coupling of moles ⁇ molecules of the organosilicon compound.
  • the coupling of the organosilicon radicals is suppressed.
  • Epoxy unit at least 0.01 mol and at most 50 mol of the amino acid of general formula III used, preferably at least 0.1 mol and at most 20 mol, more preferably at least 0.4 mol and at most 10 mol.
  • Any desired optical isomers of the amino acids can be used in the process according to the invention. It is also mög ⁇ lich to use mixtures of amino acids.
  • the reaction is in the presence of one or more
  • aliphatic alcohols preferably of the general formula R 10 -OH carried out.
  • R 10 is a linear or branched alkyl group having 1 to 20 carbon atoms, non-adjacent carbon atoms may be replaced by oxygen.
  • R 10 is particularly preferably a linear or branched alkyl group having 1 to 5 C atoms, preferably 1 to 2 C atoms may be replaced by oxygen.
  • Particularly preferred are alkyl groups having 1 to 5 carbon atoms, where particularly preferably, it is 1 C atom by oxygen is ⁇ .
  • alcohols examples include methanol, ethanol, n- Propanol, isopropanol, n-butanol, isobutanol, tert-butanol, tert-amyl alcohol, benzyl alcohol, ethylene glycol, propylene glycol, 2-methoxyethanol, 2-methoxypropanol, 2-ethoxyethanol and glycerol, polyethylene glycol or polypropylene glycol or cocondenser. sate of polyethylene glycol and polypropylene glycol.
  • Aliphatic alcohol is preferably used in proportions of at least 1% by weight and at most 10000% by weight, more preferably in proportions of at least 10% by weight and at most 5000% by weight and most preferably in proportions of at least 50% by weight and at most of 1000 wt.% Based on the mass of
  • the reaction mixture may additionally contain water, preferably at least 0.1% by weight and at most 1000% by weight, more preferably in proportions of at least 1% by weight and at most 500% by weight and most preferably in proportions of at least 5% by weight. % and at most of 1000 wt.% Based on the mass of the epoxy-functionalized
  • the reaction can be carried out in batch mode or in semi-batch mode or continuously.
  • one of the two reactants preferably the amino acid
  • the epoxide-functional organosilicon compound is added.
  • reaction times are preferably at least 1 minute to at most 100 hours, particularly preferably at least 30 minutes to at most 20 hours, and very particularly preferably
  • the reaction is preferably carried out at temperatures of at least 0 ° C and at most 200 ° C, preferably at least 20 ° C and at most 140 ° C and more preferably at least 40 ° C and at most 100 ° C performed.
  • the reaction is carried out at a pressure between at least 0.1 mbar to at most 50 bar, preferably at least 100 mbar to at most 20 bar, particularly preferably at least 0.9 bar to 10 bar.
  • further components for example solvents, may be used in amounts of at least 1% and at most 500%, preferably at least 10% and at most 200%, based on the total reaction mass.
  • Solvents are linear or cyclic, saturated or
  • unsaturated hydrocarbons e.g. Pentane, cyclohexane, toluene, ethers such as methyl tert-butyl ether, tetrahydrofuran or dioxane, halogenated hydrocarbons such as dichloromethane, 1,2-dichloroethane or chlorobenzene, or so-called dipolar
  • aprotic solvents such as acetonitrile, dimethyl sulfoxide or dimethylformamide.
  • Organosilicon compounds (0) obtained by the reaction can be isolated by removing the alcohol and optionally the solvent from the crude product. The removal is preferably carried out by distillation. If necessary, further cleaning steps can follow.
  • unreacted amino acid can be separated by washing the crude product with water or by liquid-liquid extraction. It is also possible, for example, the unreacted amino acid by adding a solvent in which the amino acid is poorly soluble, for example
  • the present invention also provides organosilicon compounds (0) containing free amino acid groups which can be prepared according to the above process. Because for the preparation of the free amino acid groupings containing organosilicon compounds (0) no
  • Emulgatorzusatz is required are the organosilicon compounds (0) with at most 15 weight percent, preferably at most 5 weight percent, more preferably at most 2 weight percent, more preferably at most 1 weight ⁇ mixed percent of an emulsifier.
  • organosilicon compounds (0) with at most 15 weight percent, preferably at most 5 weight percent, more preferably at most 2 weight percent, more preferably at most 1 weight ⁇ mixed percent of an emulsifier.
  • the organosilicon compounds (0) are mixed with no emulsifier. All the above symbols of the above formulas each have their meanings independently of each other. In all formulas, the silicon atom is tetravalent.
  • Another object of the invention is the use of the free amino acid groupings containing organosilicon compounds (O).
  • the softening and, optionally, water-repellent properties of the siloxane component on the one hand and the polar betaine structure on the other hand, which affect influence which the compounds of the invention absorption ⁇ behave significantly, can be used in cosmetic formulations for skin and hair care, in polishes for the treatment and finishing of surfaces, for Equipment of textiles and textile fibers or used as a plasticizer during or after the washing process.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Silicon Polymers (AREA)
  • Cosmetics (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

L'invention concerne un procédé pour produire des composés d'organosilicium (O) contenant un groupement acide aminé libre, qui contiennent au moins un motif de formule générale (I) et aucun motif ou au moins un motif de formule générale (II), R1, b(X)cSiO[4-(b+c)/2 (I), R2 aSiO(4-a)/2 (II), procédé dans lequel des composés d'organosilicium à fonction époxyde sont composés d'au moins un motif de formule générale (III) et d'aucun motif ou d'au moins un motif de formule générale (II), R1 b(Z) cSiO[4-(b+c)]/2 (III), R2 aSiO(4-a)/2 (II), Z ayant la signification (formule A), avec les acides aminés non protégés de formule générale (IV) : H-NR7-(CH2)f-CR8R9-COOH, qui réagissent en présence d'alcools aliphatiques R1, R2, R4, R5, R6, R7, R8, R9, X, Z, Y, a, b, c, e et f ayant les significations données à la revendication 1. L'invention concerne également des composés d'organosilicium (O) contenant des groupements acides aminés libres pouvant être obtenus selon ce procédé ainsi que des utilisations de ces composés d'organosicilium (O).
EP16726848.1A 2015-06-02 2016-05-30 Composés d'organosilicium présentant des groupements acides aminés et procédé de production desdits composés Withdrawn EP3303452A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102015210171.1A DE102015210171A1 (de) 2015-06-02 2015-06-02 Aminosäure-Gruppierungen aufweisende Organosiliciumverbindungen und Verfahren zu ihrer Herstellung
PCT/EP2016/062104 WO2016193189A1 (fr) 2015-06-02 2016-05-30 Composés d'organosilicium présentant des groupements acides aminés et procédé de production desdits composés

Publications (1)

Publication Number Publication Date
EP3303452A1 true EP3303452A1 (fr) 2018-04-11

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EP16726848.1A Withdrawn EP3303452A1 (fr) 2015-06-02 2016-05-30 Composés d'organosilicium présentant des groupements acides aminés et procédé de production desdits composés

Country Status (7)

Country Link
US (1) US20180155502A1 (fr)
EP (1) EP3303452A1 (fr)
JP (1) JP2018522092A (fr)
KR (2) KR20190075180A (fr)
CN (1) CN107636048A (fr)
DE (1) DE102015210171A1 (fr)
WO (1) WO2016193189A1 (fr)

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* Cited by examiner, † Cited by third party
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CN105778106A (zh) * 2016-04-01 2016-07-20 上海上萃精细化工有限公司 赖氨酸在制备两性离子硅油中的应用和方法
EP3576870A1 (fr) * 2017-02-03 2019-12-11 Wacker Chemie AG Procédé d'absorption de liquides dans des polymères contenant de la silicone
CN111548501A (zh) * 2020-06-02 2020-08-18 四川达威科技股份有限公司 一种含氨基酸有机硅表面活性剂的制备方法

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JPS52114699A (en) 1976-03-22 1977-09-26 Toshiba Silicone Co Ltd Preparation of silicones modified with amino acids
JP2748174B2 (ja) * 1990-01-29 1998-05-06 株式会社成和化成 化粧品基剤
JP3516272B2 (ja) * 1994-02-10 2004-04-05 株式会社成和化成 化粧品基材
GB9506926D0 (en) * 1995-04-04 1995-05-24 Croda Int Plc Cystine-siicone copolymers and their use for treating keratin substrates
JPH11106330A (ja) * 1997-08-04 1999-04-20 Ajinomoto Co Inc 化粧料組成物
DE10036532A1 (de) 2000-07-27 2002-02-21 Ge Bayer Silicones Gmbh & Co alpha.w-aminosäurefunktionalisierte Polysiloxane
JP4033758B2 (ja) * 2002-11-11 2008-01-16 チッソ株式会社 ポリオルガノシロキサン含有ε−ポリリジン
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JP5383035B2 (ja) * 2007-12-27 2014-01-08 東レ・ダウコーニング株式会社 アミノ酸変性オルガノポリシロキサンエマルジョンの製造方法
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CN103435746B (zh) * 2013-09-03 2015-07-15 东南大学 一种氨基酸两性离子水凝胶材料及其制备方法
DE102015210173A1 (de) * 2015-06-02 2016-12-08 Wacker Chemie Ag Verfahren zur Herstellung von Aminosäure-Gruppierungen aufweisenden Organosiliciumverbindungen

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Publication number Publication date
WO2016193189A1 (fr) 2016-12-08
JP2018522092A (ja) 2018-08-09
KR20190075180A (ko) 2019-06-28
US20180155502A1 (en) 2018-06-07
KR20170140323A (ko) 2017-12-20
CN107636048A (zh) 2018-01-26
DE102015210171A1 (de) 2016-12-08

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