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
  • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
  • C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
  • A61K8/04—Dispersions; Emulsions
  • A61K8/06—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
  • A61K8/896—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
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/02—Preparations for cleaning the hair
• • 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
  • A61Q5/12—Preparations containing hair conditioners
• • 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
  • C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl 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
  • C08G77/38—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
• • 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
  • C08L83/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
• • 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 invention relates to fully acylated amino-functional and simultaneously hydroxy-terminated organopolysiloxanes, aqueous emulsions comprising the organopolysiloxanes, their use in the field of cosmetics and preparation of the organopolysiloxanes
• Amino-containing organopolysiloxanes whose amino groups are acylated have been state of the art for some time and are used, for example, as textile finishing agents. Above all, the acylation serves to effectively reduce thermal yellowing.
• JP-A-57/101076 describes the partial or complete acetylation with acetic anhydride of
• organosiloxanes having reactive end groups eg Si-OH or Si-O-alkyl
• Condensation catalysed which leads to an optionally no longer controllable increase in viscosity or gelling
• the invention relates to hydroxy-terminated
• R is a monovalent unsubstituted
• halogen-substituted hydrocarbon radical having 1 to 20
• R 1 is a radical R, -OR 4 or -OH
• R 4 is an alkyl radical having 1 to 6 carbon atoms
• G is a group of the general formula (2)
• R 1 is alkyl of 1 to 20 carbon atoms
• b mean integer values of at least 1.
• the invention further provides aqueous emulsions (W) containing 5% by weight to 70% by weight of the hydroxy-terminated organopolysiloxanes (0) of the general formula (1) and 1 to 150% by weight, based on the weight of the organopolysiloxane ( 0) of an emulsifier (E),
• the emulsions (W) are characterized by very good storage stability as well as dilution stability.
• Emulsions (W) are very good in compositions for the
• Cosmetics such as shampoo or conditioner can be used.
• Emulsions (W) in compositions for cosmetics are hair cleansing and care.
• the emulsions () cause, for example, good in hair by their content of organopolysiloxanes (0)
• the invention likewise provides a process A for the preparation of the hydroxy-terminated organopolysiloxanes (O), in which hydroxy-terminated organopolysiloxanes (N) of the
• G ' is a group of general formula (2a)
• R 2 is -N-R 3 -NH (2a)
• R 1 , R 2 , R 3 , R 4 , a and b have the above meanings
• the mixture of emulsifiers (El) and organopolysiloxane (O) can be emulsified immediately, so that the resulting oil viscosity of organopolysiloxane (0) remains stable.
• Emulsifying in one step is a very efficient one
• the invention likewise provides a process B for the preparation of the hydroxy-terminated organopolysiloxanes (0), in which hydroxy-terminated organopolysiloxanes (N) of the
• G ' is a group of general formula (2a) and R, R 1 , R 2 , R 3 , 4, a and b have the above meanings, with acyclic carboxylic acid anhydrides of the general formula (3)
• organopolysiloxane (N) amine groups has also in
• the conversion in "stoichiometrically equivalent amount to the amine groups present in the organopolysiloxane (N)" means that per mole of nitrogen atom in the general formula (2a) 1 to at most 1.1, preferably at most 1.05 mol, in particular at most 1.01 mol acyclic carboxylic anhydride of
• the monovalent hydrocarbon radical R can be any organic radical
• R has from 1 to 6 carbon atoms, more preferably linear Alkyl radicals and phenyl radicals.
• Preferred halogen substituents are fluorine and chlorine.
• Hydrocarbon radicals R are methyl, ethyl, phenyl.
• the alkyl radical is preferably selected from methyl,
• the radicals R 2 , R 3 is an ethylene, n-propylene, iso-butylene or n-butylene radical, particularly preferably the radical G 'is the radical - (CH 2 ) 3 NH (CH 2 ) NH 2 .
• R 5 can be linear, cyclic or branched.
• R5 has from 1 to 6 carbon atoms, with particular preference being given to linear alkyl radicals, in particular methyl, ethyl, n-propyl or isopropyl.
• a preferably denotes integer values of at least 200, particularly preferably at least 300, in particular at least 500 and at most 1300, particularly preferably at most 1100 and in particular at most 900.
• b preferably means integer values of at most 100, particularly preferred at most 10, in particular at most 5.
• a and b are selected so that the organopolysiloxane (0) has a viscosity of at least 100, more preferably at least 1000, particularly preferably at least 5 000,
• the amine number of the organopolysiloxane (N) used is preferably at least 0.001, in particular at least 0.01 mmol / g and at most 5, more preferably at most 1, very particularly preferably at most 0.1, in particular at most 0.05 mmol / g,
• the amine number refers to the amount of mol
• Emulsifiers (E) all hitherto known, ionic and nonionic emulsifiers both individually and as mixtures of different emulsifiers are used, with which previously aqueous dispersions, especially aqueous emulsions of organopolysiloxanes could be produced.
• inorganic solids are e.g. Silicas or
• Alkyl sulfates especially those having a chain length of 8 to 18 carbon atoms, alkyl and Alkarylethersulfate having 8 to 18 carbon atoms in the hydrophobic radical and 1 to 40 ethylene oxide (EO) - or propylene oxide (PO) units.
• EO ethylene oxide
• PO propylene oxide
• sulfonates especially alkyl sulfonates having 8 to 18 carbon atoms, alkylaryl sulfonates having 8 to 18 carbon atoms, taurides, esters and half esters of sulfosuccinic acid with monohydric alcohols or alkylphenols having 4 to 15 carbon atoms; optionally, these alcohols or alkylphenols may also be ethoxylated with 1 to 40 EO units.
• nonionic emulsifiers examples include:
• polyvinyl alcohol which still has 5 to 50%, preferably 8 to 20 vinyl acetate units, with a degree of polymerization of 500 to 3000.
• Alkylpolyglycolether preferably those having 3 to 40 EO units and alkyl radicals of 8 to 20 carbon atoms.
• Alkylarylpolyglycolether preferably those having 5 to 40 EO units and 8 to 20 carbon atoms in the alkyl and
• Oligoglykosidrest with on average o 1-10 hexose or
• Pentose units or mixtures thereof mean.
• Natural products and their derivatives such as lecithin, lanolin, saponins, cellulose; Cellulose alkyl ethers and
• Carboxyalkylcelluloses whose alkyl groups each have up to 4 carbon atoms.
• cationic emulsifiers are:
• Alkyloxazoliniumsalze especially those whose alkyl chain has up to 18 carbon atoms, especially the halides, sulfates, phosphates and acetates.
• aminoethyl glycine or N-alkyl-2-aminopropionic acid salts.
• Betaines such as N- (3-acylamidopropyl) -N, N-dimethylammonium salts with a Ce-Ci-acyl radical and alkyl imidazolium betaines.
• Preferred emulsifiers are nonionic emulsifiers, in particular those listed under 6. above
• Alkyl polyglycol ethers and cationic emulsifiers in particular the quaternary alkyl and alkylbenzene ammonium salts listed under 15. above.
• the component (E) can be from one of the o.g. Emulsifiers or a mixture of two or
• Emulsifiers can be used in pure form or as solutions of one or more emulsifiers in water or organic solvents.
• the invention further aqueous emulsions (W) containing 5 wt .-% to 70 wt .-% of the hydroxy-terminated Organopolysiloxanes (O) of the general formula (1) and 2 to 150% by weight, based on the weight of the organopolysiloxane (0), of an emulsifier (E).
• the aqueous emulsions (W) consist of a
• the weight ratios of the discontinuous oil phase and the continuous water phase can be varied within wide limits.
• the proportion of the oil phase is 5 to 70 wt.%, Preferably 10 to 60 wt.%, Each based on the total weight of the emulsion (W).
• the proportion of emulsifiers is preferably in the range from 2 to 150% by weight, in particular up to 50% by weight, in each case based on the weight of the oil phase.
• the preferred mean particle size of the discontinuous oil phase is less than 2 ⁇ m, in particular less than 1 ⁇ m. Especially preferred are average particle sizes of at most 0.8 ⁇ m, in particular not more than 0.5 ⁇ m.
• the emulsion (W) may for certain purposes, for example for use in cosmetic compositions, in addition to the above ingredients contain additives.
• Suitable additives are, for example, biocides, such as fungicides,
• Antifreeze, antistatic agents, dyes, flame retardants and organic plasticizers are examples of organic plasticizers.
• Emulsifiers (El), which are used in the process A during the acetylation, must be compared to the acyclic
• Carboxylic anhydrides behave essentially inert. Under In this premise, they are preferably selected from the emulsifiers (E) described above.
• Alkylpolyglycolethe preferably those having 3 to 40 EO units and alkyl radicals of 8 to 20 carbon atoms.
• Alkylarylpolyglycolether preferably those having 5 to 40 EO units and 8 to 20 carbon atoms in the alkyl and
• Alkyloxazoliniumsalze especially those whose alkyl chain has up to 18 carbon atoms, especially the halides, sulfates, phosphates and acetates.
• emulsifiers are nonionic
• Emulsifiers in particular those mentioned above under (a).
• the component (El) may be from one of the above-mentioned.
• Emulsifiers or consist of a mixture of two or more o.g, emulsifiers.
• Neutralizers (B) used in Preparation B are alkaline salts such as
• Potassium hydroxide, lithium hydroxide, (earth) alkali metal carbonates eg potassium carbonate, sodium carbon, lithium carbonate,
• alkali silanolates e.g. Sodium trimethylsilanolate
• Lithium trimethylsilanolate, (alkaline) alkali siloxanolate e.g.
• Lithium siloxanolate, (alkaline) alkanol alkanolates e.g.
• Sodium methoxide, sodium ethoxide, potassium tert. butanolate or ammonium salts e.g. Ammonium hydroxide or organic
• Amines e.g. Triethanolamine (TEA), diethanolamine, ethanolamine, triethylamine, isopropylamine.
• the pressures for the processes A and B are preferably at least 0.010, in particular at least 0.05 MPa and
• the temperature in the process A is preferably at least 0 ° C, more preferably at least 10 ° C, in particular
• the temperature in the process B is preferably at least 0 ° C, more preferably at least 10 ° C, in particular
• the organopolysiloxane (1) can be prepared either by breaking the
• Emulsion in any desired manner for example by adding water-soluble organic solvents, for example methanol, ethanol, isopropanol, acetone ,. or by addition of salts, such as sodium chloride, or by extraction with organic solvents, for example n-hexane, n-heptane, mixtures of n-hexane-isopropanol, n-hexane-acetone are obtained virtually emulsifier-free. All the above symbols of the above formulas each have their meanings independently of each other. In all
• Formulas is the silicon atom tetravalent.
• the acetylated amine oil of the general formula (1) has a viscosity of
• R 1 - methoxy, G '- 3 - ((2-aminoethyl) amino) propyl and a and b are chosen such that the oil has a viscosity of 14 100 mPas and an amine value of 0.032 mmol / g, becomes 40 ° C heated and with 1.96 g ⁇ 19.2 mmol; equimolar to the amine content) Added acetic anhydride and then stirred for 30 min at 40 ° C. After cooling to room temperature has
• acetylated amine oil has a viscosity of 24,600 mPas.
• Lutensol ® IT6 (Fa. BASF), 3.45 wt.% Of an aqueous solution of cetyltrimethylammonium chloride (29% pure, available under the trade name Genamin® CTAC, Fa. Clariant) by weight and 6.00 presented% deionized water. Subsequently, 55.00 wt.% Of organopolysiloxane of the general formula (1) are metered in, and under high shear, a pre-emulsion is prepared. This is by adding portions of
• G ' 3 - ((2-aminoethyl) amino) ropyl and a and b selected such that the oil has a viscosity of 18,000 mPas and an amine number of 0.022 mmol / g. 0.12% by weight
• Acetylation can be detected by the two H3C-C0 signals at 1.77 ppm and 2.03 ppm.
• Example 2 The acetylation and emulsion preparation of Example 2 is repeated analogously with the difference that in addition to desalted water, the following starting materials were used: 3.45 wt.% Isotridecylhexaethoxylat, commercially available under the following starting materials: 3.45 wt.% Isotridecylhexaethoxylat, commercially available under the following starting materials: 3.45 wt.% Isotridecylhexaethoxylat, commercially available under the
• Acetylation can be detected by the two H3C-CO signals at 1.77 ppm and 2.03 ppm.
• Example 2 The acetylation and emulsion production of Example 2 is repeated analogously with the difference that in addition desalted
• Citric Acid Citric Acid 0, 20
• Methylchloroisothiazolinone Kathon CG 0.10 and methylisothiazolinone.

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• 2010
  • 2010-09-28 DE DE102010041503A patent/DE102010041503A1/de not_active Withdrawn
• 2011
  • 2011-09-19 WO PCT/EP2011/066201 patent/WO2012041733A1/de not_active Ceased
  • 2011-09-19 CN CN201180046915.0A patent/CN103282410B/zh active Active
  • 2011-09-19 EP EP11761048.5A patent/EP2622003B1/de active Active
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