EP2648695A2 - Zubereitungen enthaltend polysiloxane mit stickstoffhaltigen gruppen - Google Patents

Zubereitungen enthaltend polysiloxane mit stickstoffhaltigen gruppen

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Publication number
EP2648695A2
EP2648695A2 EP11791488.7A EP11791488A EP2648695A2 EP 2648695 A2 EP2648695 A2 EP 2648695A2 EP 11791488 A EP11791488 A EP 11791488A EP 2648695 A2 EP2648695 A2 EP 2648695A2
Authority
EP
European Patent Office
Prior art keywords
formulation
inci
hair
polysiloxane
carbon atoms
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Withdrawn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
EP11791488.7A
Other languages
German (de)
English (en)
French (fr)
Inventor
Frauke Henning
Michael Ferenz
Sascha Herrwerth
Christian Hartung
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.)
Evonik Operations GmbH
Original Assignee
Evonik Degussa 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 Evonik Degussa GmbH filed Critical Evonik Degussa GmbH
Publication of EP2648695A2 publication Critical patent/EP2648695A2/de
Withdrawn legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89Polysiloxanes
    • A61K8/896Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
    • A61K8/898Polysiloxanes 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/10Washing or bathing preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/06Preparations for styling the hair, e.g. by temporary shaping or colouring
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/12Preparations containing hair conditioners
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/10General cosmetic use
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02Preparations containing skin colorants, e.g. pigments
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/04Preparations for care of the skin for chemically tanning the skin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/08Anti-ageing preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/02Preparations for cleaning the hair

Definitions

  • the present invention relates to cosmetic preparations containing polysiloxanes which are modified with amino functions with amino functions and at least one further polar functional group in defined proportions, and the use of these preparations in cosmetic formulations for the care of skin and keratinic fibers.
  • Aminofunctional siloxanes are widely used as conditioning agents for textiles, additives in shampoos and hair care products and water repellents. A variety of structural variations of this group of substances is described in the prior art and is accessible via different manufac turing routes. In this case, terminally modified with amino groups, purely linear polydimethylsiloxanes are not variable in their degree of modification. This is disadvantageous in that both the number and the type of amino groups greatly affect substantivity, i. on the binding capacity on carriers such as keratinic substances, the aminopolysiloxane exercise. Thus, the total nitrogen content of an aminosiloxane is an important index that correlates directly with its substantivity.
  • Polysiloxanes having high degrees of modification with a chain length which can be variably adjusted independently of the nitrogen content can be obtained by lateral functionalization of a polysiloxane having organic substituents containing amino groups.
  • the prior art discloses a multitude of publications on laterally modified aminosiloxanes which are currently used in large quantities in cosmetic formulations.
  • the preparation of laterally modified aminosiloxanes can be carried out base or acid catalyzed.
  • the base-catalyzed equilibration for the preparation as described for example in EP 1972330 A2 in Sections 0154 and 0155, can lead either to terminally dihydroxy-functional, pendantly oligomerically-modified polysiloxanes or to amino-modified polysiloxanes on the side lead, the chain ends are endcapsulated with trimethylsilyl groups.
  • US Pat. No. 6,171,515 B1 describes end-capped and dialkoxy-functional aminopolysiloxanes which undergo a functionalization of the primary and secondary amino groups with epoxy-functional monomers, such as, for example, glycidol, in a synthesis step following the siloxane polymerization.
  • a similar functionalization of aminosiloxanes with alkylene oxides is described in DE 69003009 T2. Further functionalizations of amino-functional polysiloxanes with Glycerol carbonate or gluconolactone are described in EP 192330 A2 and in J. Phys. Chem. B 2010, 1 14, 6872-6877.
  • the derivatization of the amino function has a substantial influence on the substantivity of the nitrogen-containing polysiloxanes on skin or keratin fibers.
  • the sensory properties of the cosmetic formulations are dependent on the type and amount which is deposited in the application of the nitrogen-containing polysiloxanes used to skin or hair.
  • JP 2002-167437 A describes laterally functionalized polysi oxanes which are usually functionalized, and which are prepared by the reaction of the corresponding aminopolysiloxanes with cyanamide.
  • DE 102005004704 A1 describes the condensation copolymerization of a dihydroxy-functional polydimethylsiloxane with a guanidino group-containing silane and an amino group-containing silane. Although it is possible in this way to functionalize the polysaccharide with different types of nitrogen-containing groups, DE 102005004704 does not disclose access to end-capped multi-amino-functional polysiloxanes.
  • aminopolysiloxanes are inter alia their viscosity reduction of the formulations containing them. It is therefore desirable from a formulation point of view to use as small amounts of amino-functional siloxanes as possible, without having to accept significant losses in performance.
  • the object of the present invention is to provide cosmetic care active ingredients with good application properties.
  • nitrogen-containing polysiloxanes of the general formula 1 are excellent, cosmetic care active ingredients.
  • the present invention thus relates to the use of polysiloxanes as described in claim 1 as care active in dermatological, cosmetic and pharmaceutical applications and corresponding formulations containing the nitrogen-containing polysiloxanes of the general formula 1.
  • An advantage is that the nitrogen-containing polysiloxanes of the general formula 1 effect an improved conditioning of skin and hair than previously known aminopolysiloxanes.
  • Yet another advantage of the present invention is that the nitrogen-containing polysiloxanes of the general formula 1 have a very good substantivity.
  • a reduction in the amount of amino-functional polysiloxanes used has the advantage that the formulation and incorporation processes are simplified.
  • amino-functional agents with the same or better conditioning of skin and hair requires smaller amounts of thickener in a cosmetic surfactant formulation, since amino-functional siloxanes generally have a diluting effect in surfactant formulations (for example in shampoos or shower gels).
  • polysiloxanes used according to the invention represent structurally well-defined polymers whose nitrogen content, type and amount of the amino groups and their chain length can be adjusted independently of each other variably via the formulation, so that a constant composition and a reproducible quality the amino-containing polymers is given with a view to the respective application.
  • the nitrogen-containing polysiloxanes used are capable of improving both properties such as combability, softness, bulk, moldability, handleability, the entanglement of undamaged and damaged hair, and a beautiful sheen to the hair to lend.
  • the present invention is the use of at least one polysiloxane of the general formula 1
  • D [R 1 2 Si0 2/2]
  • D A [R 1 Si (R 7 NHR 3 ) 0 2 2 ]
  • R 1 independently of one another are identical or different linear or branched, saturated or unsaturated hydrocarbon radicals having 1 to 30 carbon atoms or else aromatic hydrocarbon radicals having 6 to 30 carbon atoms, preferably methyl or phenyl, in particular methyl;
  • R 2 independently of one another equal to R 1 , an alkoxy radical or a hydroxy group, preferably R 1 , in particular methyl;
  • R 3 independently of one another hydrogen or a hydrocarbon radical substituted by nitrogen atoms, for example an aminoethyl radical, in particular hydrogen;
  • R 4 independently of one another are identical or different linear or branched, saturated or olefinically unsaturated hydrocarbon radicals having from 8 to 30 carbon atoms, for example decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, in particular hexadecyl and octadecyl;
  • R 5 independently of one another are identical or different linear or branched, saturated or unsaturated polar hydroxy-substituted amide radicals having 1 to 30 carbon atoms and / or hydroxy-substituted carbamate radicals having 1 to 30 carbon atoms and / or ethoxylated amine radicals having 1 to 30 carbon atoms and / or guanidine radicals or alkylenylguanidine radicals having 1 to 30 carbon atoms, preferably selected from the group of the substituents of the formula 1 a to 1 h, in particular 1 e and 1 f,
  • R is hydrogen, a hydrocarbon radical, an acyl radical, a carboxylate radical or a carbamate or carbonate radical, in particular hydrogen and CH 3 -C (O);
  • b 10 to 5000, preferably 20 to 2000, in particular 20 to 1000,
  • c 1 to 500, preferably 1 to 100, in particular 1 to 30,
  • d 0 to 500, preferably 0 to 100, in particular 0 to 30,
  • g 0 to 20, preferably 0 to 10, in particular 0,
  • h 0 to 20, preferably 1 to 10, in particular 1-2, or their ionic adducts with protic reactants H + A " ,
  • a process for the preparation of the polysiloxanes used according to the invention or contained in the formulations of the invention is based on the use of the compounds exemplified below, wherein
  • R 1 , R 4 , R 7 and h have the abovementioned meaning of the formula 1
  • R 8 is a hydrogen atom, a methyl or a carboxyl group, preferably H or acetyl
  • R 9 is an alkyl or acyl radical, in particular methyl, ethyl or Acetyl is,
  • silanes are suitably used as a monomer. If it is advantageous for the later application, the silanes can be precondensed under hydrolytic acidic conditions to give oligomers before the polymer structure is initiated by adding the dihydroxy-functional polysiloxanes.
  • the dialkoxysilanes used are prepared by synthesis methods known in the art.
  • the guanidation of amino-functional silanes is carried out analogously to that in JP 2002 167437 described guanidation of aminosiloxanes.
  • the reaction of amino-functional siloxanes with glycerol carbonate or gluconolactone takes place on the basis of EP 1 972 330 A1 and J. Phys. Chem. B 2010, Vol. 1 14, pp. From 6872 to 6877.
  • carboxylic acids such as acetic acid, propionic acid, isononanoic acid or oleic acid are used.
  • the reaction can be carried out with the addition of small amounts of water to accelerate the hydrolysis, often sufficient moisture is present in the undried reagents used.
  • the reaction can be carried out neat or in the presence of solvents, such as in aliphatic and aromatic, protic and aprotic solvents, glycols, ethers, fatty alcohol alkoxylates, mono-, di- and triglycerides or oils of synthetic and natural origin.
  • solvents such as in aliphatic and aromatic, protic and aprotic solvents, glycols, ethers, fatty alcohol alkoxylates, mono-, di- and triglycerides or oils of synthetic and natural origin.
  • solvents is advantageous, for example, when the chain lengths of the desired structures cause high viscosities.
  • the solvent can be added before, during or after the reaction.
  • the reaction may be carried out at temperatures ranging from room temperature to 150 ° C, preferably at 50-100 ° C.
  • the alcohols liberated in the hydrolysis are distilled off during or after the reaction under vacuum. Alternatively, they can be carried out by a neutralization step and a filtration step.
  • the various monomer units of the siloxane chains given in the formulas can be constructed in blocks of any number of blocks and of any sequence or random distribution. Ionic adducts of the amino-functional siloxanes used according to the invention or contained in the formulations according to the invention with protic reactants H + A " are in the form -NH 3 + A " .
  • the anions A " are identical or different counterions to the positive charges on the protonated, primary amino groups selected from inorganic or organic anions of the acids H + A " , and their derivatives.
  • Preferred anions are chloride, sulfate or hydrogen sulfates, carbonate or bicarbonate, phosphate or hydrogen phosphates, acetate or homologous carboxylates with linear or branched, saturated or olefinically unsaturated alkyl chains, aromatic carboxylates, carboxylates formed from amino acids, citrates, malonates, fumarates, maleates , substituted and unsubstituted succinates and carboxylates formed from L-hydroxycarboxylic acids such as lactate.
  • the aminosiloxanes and their ionic adducts can naturally be present in dissociation equilibria, depending on the stability of the adduct formed.
  • the indices used in the formulas are to be regarded as statistical averages.
  • care active substance is understood here to mean a substance which serves the purpose of preserving an object in its original form or the effects of external influences (for example, time, light, temperature, pressure, pollution, chemical reaction with others, with the Article in contact reactive compounds) such as aging, fouling, material fatigue, fading, masking, mitigating or avoiding, or even improving desired positive properties of the article Finally, for example, improved hair shine or greater elasticity of the object under consideration called.
  • Water-soluble or water-insoluble polysiloxanes according to formula 1 can be used according to the invention. Depending on the formulation to be produced (turbid or clear formulations), it is familiar to the skilled worker whether water-soluble or insoluble polysiloxanes should be used to prepare the formulation.
  • the term "water-insoluble” in the sense of the present invention is defined as having a solubility of less than 0.01% by weight in aqueous solution at 20 ° C. and 1 bar pressure
  • water-soluble in the sense of the present invention is defined as having a solubility equal to or below more than 0.01 weight percent in aqueous solution at 20 ° C and 1 bar pressure.
  • the use according to the invention of the polysi loxanes according to formula 1 as care active substance preferably takes place in surfactant-containing, in particular in surfactant-containing aqueous formulations, whereby the term "aqueous" indi ese m connection formulations are understood which at least 40 wt .-%, in particular at least 60 wt .-%, more preferably at least 75 wt .-%, of water, based on the total formulation.
  • an inventively preferred use as care active ingredient is the use as a conditioning agent, in particular as a conditioner for skin and hair, preferably for hair. Therefore, the polysiloxanes according to formula 1 are preferably used in hair treatment agents and hair aftertreatment agents.
  • the use according to the invention is particularly in Hair treatment compositions and hair treatment compositions for rinsing or remaining in the hair, for example in shampoos with or without pronounced conditioning effect, 2in1 shampoos, rinses, hair treatments, hair masks, hairdressing aids, styling agents, hair lotions, hair fixatives, permanent wave agents, hair straightening agents and agents for dyeing the hair preferably performed.
  • the polysiloxanes according to formula 1 are advantageously used in a concentration of from 0.01 to 20% by mass, preferably from 0.1 to 8% by mass, more preferably from 0.2 to 4% by mass, very particularly preferably from 0.2 to 1, 0, in particular up to 0.7 percent by weight based on the total formulation used in the formulations.
  • the polysiloxanes according to formula 1 can be used advantageously for dispersing particles, in particular in cosmetic, dermatological or pharmaceutical formulations. Therefore, according to the invention, the polysiloxanes according to formula 1 can additionally be used as dispersing aids for particles, in particular metal oxides, in particular nanoparticulate TiO 2 , which may be hydrophobic or hydrophilic, color pigments, such as Fe x O y (iron oxides), Mica, Eq immers, ZnO, Titandi oxi d or manganese dioxide, wherein the formulations are preferably selected from the list consisting of sunscreens, decorative cosmetic formulations, such as lipsticks, make-ups, mascara, foundations or Blemish Creams.
  • sunscreens decorative cosmetic formulations, such as lipsticks, make-ups, mascara, foundations or Blemish Creams.
  • Another aspect of the present invention is dermatological and / or pharmaceutical formulations containing the polysiloxanes of general formula 1.
  • Preferred formulations according to the invention are those in which the use described above is preferably carried out.
  • formulations according to the invention which contain fatty alcohol ethoxylates contain at least one further component which is selected from at least one of the two groups "ionic surfactants" or "fatty alcohols".
  • Formulations preferred according to the invention comprise the polysiloxane of the general formula 1 in a concentration of 0.01 to 20% by mass, preferably 0, 1 to 8% by mass, more preferably from 0.2 to 4% by mass, very particularly preferably from 0.2 to 1.0 , in particular up to 0.7 percent by weight based on the total formulation.
  • the formulations according to the invention are preferably cosmetic skin and hair care formulations, in particular hair shampoos, conditioners and rinses which are washed out after application (so-called rinse-off formulations), such as, for example, shampoos and conditioners.
  • Shampoos preferred according to the invention are characterized in that they contain as further component a deposition polymer, such as, for example, quaternized polysaccharides, quaternized polyacrylates, quaternized polycelluloses, quaternized starches, quaternized guar or other quaternized or aminic polymers from the group of polyquaternium (PQ) compounds (INCI name).
  • a deposition polymer such as, for example, quaternized polysaccharides, quaternized polyacrylates, quaternized polycelluloses, quaternized starches, quaternized guar or other quaternized or aminic polymers from the group of polyquaternium (PQ) compounds (INCI name).
  • quats are selected from the group consisting of guar-quat (for example hydroxypropyl guar hydroxypropyltrimonium chlorides, guar hydroxypropyltrimonium chlorides or guar hydroxypropyltrimonium chlorides) or the polyquaternium (PQ) compounds such as PQ-10, PQ-7, PQ- 22, PQ-49, PQ 47, PQ-67 or PQ-6.
  • guar-quat for example hydroxypropyl guar hydroxypropyltrimonium chlorides, guar hydroxypropyltrimonium chlorides or guar hydroxypropyltrimonium chlorides
  • PQ polyquaternium
  • Shampoos preferred according to the invention are characterized in that they contain as further component at least one anionic surfactant (for example alkyl ether sulfate, alkyl sulfate or alkylbenzenesulfonate) and at least one further surfactant from the group of alkylbetaines or alkyloligoglucosides or mono- and / or dialkylsulfosuccinates or alkylamidobetaines or fatty acid sarcosinates ,
  • anionic surfactant for example alkyl ether sulfate, alkyl sulfate or alkylbenzenesulfonate
  • further surfactant from the group of alkylbetaines or alkyloligoglucosides or mono- and / or dialkylsulfosuccinates or alkylamidobetaines or fatty acid sarcosinates
  • Conditioners preferred according to the invention are characterized in that they contain in particular at least one quaternized or aminic or imidazolium-containing organic compound such as Cetri monium chloride, Dicetyldimonium chloride, Quaternium-18, Behentrimonium chlorides, Distearyldimonium chlorides, Quaternium-87, Palmitamidopropyltrimonium chlorides and the corresponding methosulfates or the amidamines stearamidopropyl dimethylamine and behenylamidopropyl dimethylamine.
  • the formulation according to the invention may contain, for example, at least one additional component selected from the group of
  • Hydrotropes (or polyols),
  • the solids content determination is carried out by distilling off the solvent for two hours on a rotary evaporator at 60 ° C and 20 mbar and subsequent weighing.
  • the 13 C NMR spectrum shows a complete reaction with the gluconolactone, because there are no signals at 45 ppm would mean the residual amounts of a CH 2 -NH 2 group.
  • Example 3 Preparation of a gluconolactampropyl- and aminopropyl-functional polysiloxane
  • a gluconolactampropyl- and aminopropyl-functional polysiloxane In a 500 ml four-necked flask with attached KPG stirrer, dropping funnel, reflux condenser and internal thermometer, 200 g of dihydroxy-functional polydimethylsiloxane having a chain length of 47.2 dimethylsiloxane units, 6.52 g of 3-aminopropylmethyldiethoxysilane (Dynasylan® 1505, Evonik Degussa GmbH) and 6 , 48 g of 64.8% strength 2-propanol silane solution from Example 1 with stirring to 85 ° C heated.
  • the vacuum is broken and stirred after addition of 4, 18 g of hexamethyldisilazane (98.5%, ABCR GmbH) for 1 hour at 85 ° C and room pressure.
  • the mixture is then distilled for 3 hours at 85 ° C and 20 mbar.
  • a cloudy, colorless product with a viscosity of 41,500 mPa * s at 25 ° C. is obtained.
  • the proportion of trimethylsilyl end-capped chain ends determined by 29 Si-NMR is 80%.
  • the potentiometric titration of the product with two different basic nitrogen-containing groups has two turnover points.
  • compositions are named in the compositions in the form of the generally accepted INCI nomenclature using the English terms. All concentrations in the application examples are given in percent by weight.
  • Example No. 3 For evaluating the conditioning of skin (skin care performance) of Example No. 3 according to the invention in aqueous, surfactant formulations, sensory hand washing tests were carried out in comparison to Comparative Example 2 according to the prior art.
  • Comparative Example 2 is widely used in industry as a care active ingredient and is considered to be a highly effective care active ingredient in aqueous, surface-active formulations.
  • a group of 10 trained test persons washed their hands and evaluated foam properties and skin sensation on the basis of grades ranging from 1 (poor) to 5 (very good).
  • Tab. 1 Test formulations for hand washing test.
  • Table 2 shows the results of the hand wash test. On the basis of the measurement results, it can be seen that formulation 1 b according to the invention using Example 3 according to the invention is superior in all application properties in comparison with comparative formulation V2b according to the prior art.
  • Example 3 according to the invention in Formulation 1b leads to an improvement in the skin properties in comparison with Comparative Example 2 in Formulation V2b.
  • Example 3 To evaluate the conditioning of skin (skin care performance) and the foaming properties of Example 3 according to the invention in aqueous, surface-active mold formulations, such washing tests were carried out in comparison to Comparative Example 2 according to the prior art , This time a lower use concentration compared to Comparative Example 2 was used to test the inventive Example 3 to a higher efficiency.
  • control formulation 0c a formulation without the addition of an organomodified siloxane is used.
  • Inventive Example 4 and Comparative Example 1 were used in simple cosmetic formulations (shampoo and hair conditioner).
  • the pretreatment of the hair takes place in the case of property testing of hair rinses by a shampoo containing no conditioning agent.
  • hair tresses used for sensory tests are predamaged in a standardized way by a permanent wave treatment and a bleaching treatment.
  • hairdressing customary products are used.
  • the criteria of the invention are described in DE 103 27 871. The invention is based on the following examples.
  • the strands of hair are moistened under running, warm water. The excess water is gently squeezed out by hand, then the shampoo is applied and gently incorporated into the hair (1 ml / strand of hair (2 g)). After a residence time of 1 min, the hair is rinsed for 1 min.
  • the rinse is immediately applied and gently incorporated into the hair (1 ml / strand of hair (2 g)). After a residence time of 1 min, the hair is rinsed for 1 min. Before the sensory evaluation, the hair is dried in air at 50% humidity and 25 ° C for at least 12 hours.
  • Sensory scores are scored on grades ranging from 1 to 5, with 1 being the worst and 5 the best scoring.
  • the individual test criteria each receive their own rating.
  • test criteria are: wet combability, wet grip, dry combability, dry grip, appearance / gloss.
  • the following table compares the results of the sensory evaluation of the treatment of the hair strands as described above with the formulation 1d according to the invention, the comparison formulation V2d and the control formulation Od (placebo without test substance).
  • Example 4 and Comparative Example 1 of the prior art were used in simple cosmetic formulations (shampoo and hair conditioner). This time, a lower use concentration was used in comparison with Comparative Example 1 in order to test Example 4 according to the invention for greater effectiveness.
  • Comparative Example 1 (not According to the Invention) 0.5% Tab. 10: Hair Conditioner Formulations for testing hair conditioning properties at different concentrations. The following table compares the results of the sensory evaluation of hair strand treatment as described above with formulation 1d according to the invention, comparison formulation V2d and control formulation Od (placebo without test substance).
  • Tab. 11 Results of conditioning hair from shampoo formulation using different concentrations. The results show, surprisingly, that formulation 1f according to the invention with Example 4 according to the invention is superior or equivalent in all application properties in comparison to comparative formulation V2f according to the prior art, although 20% less Example 4 was used as Comparative Example 1 in the respective formulations.
  • Tab. 12 Results of the conditioning of hair from hair conditioner formulations using different concentrations. Also in the application of hair rinse, the formulation according to the invention 1 g with Example 4 according to the invention in the sensory evaluation shows very good cosmetic strength. However, comparison Example 1 with Comparative Example 1 was at least achieved or slightly exceeded by Example 1 according to the invention with Inventive Example 4, although 20% less Example 4 than Comparative Example 1 was used in the respective formulations.
  • ANTIL ® 200 Evonik Goldschmidt GmbH (INCI: PEG-200 hydrogenated glyceryl palmate 2.00% PEG-7 Glyceryl Cocoate)
  • ANTIL ® 200 Evonik Goldschmidt GmbH (INCI: PEG-200 hydrogenated glyceryl palmate 2.00% PEG-7 Glyceryl Cocoate)
  • Citric Acid (30% in water) 3.00%
  • VARISC-Ft EQ 65 Evonik Goldschmidt GmbH 2.00% (INCI: Distearyl Dimonium Chloride, Cetearyl Alcohol)
  • VARISOFT ® EQ 65 Evonik Goldschmidt GmbH 2.00% (INCI: Distearyl Dimonium Chloride, Cetearyl Alcohol)
  • Myristyl myristate 1 1, 00%
  • Triisostearin 1 1, 00%
  • Citric Acid (10% Solution) (pH Adjustment to 4.0) q.s. Methylisothiazolinone, methylparaben, ethylparaben;

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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)
  • Dermatology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)
  • Silicon Polymers (AREA)
  • Medicinal Preparation (AREA)
EP11791488.7A 2010-12-09 2011-11-15 Zubereitungen enthaltend polysiloxane mit stickstoffhaltigen gruppen Withdrawn EP2648695A2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102010062676A DE102010062676A1 (de) 2010-12-09 2010-12-09 Zubereitungen enthaltend Polysiloxane mit stickstoffhaltigen Gruppen
PCT/EP2011/070091 WO2012076293A2 (de) 2010-12-09 2011-11-15 Zubereitungen enthaltend polysiloxane mit stickstoffhaltigen gruppen

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EP2648695A2 true EP2648695A2 (de) 2013-10-16

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US (1) US20130259821A1 (zh)
EP (1) EP2648695A2 (zh)
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Families Citing this family (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102012201167A1 (de) 2012-01-27 2013-08-01 Evonik Industries Ag Mischungszusammensetzung enthaltend aminofunktionelle Siloxane, hydrophobePartikel und hochmolekulare Silicone sowie dessen Verwendung zur Lederbehandlung
DE102013214081A1 (de) 2013-07-18 2015-01-22 Evonik Industries Ag Neue aminosäuremodifizierte Siloxane, Verfahren zu ihrer Herstellung und Anwendung
DE102013216777A1 (de) 2013-08-23 2015-02-26 Evonik Industries Ag Bei Raumtemperatur härtbare Silikonharz-Zusammensetzungen
DE102013216787A1 (de) 2013-08-23 2015-02-26 Evonik Degussa Gmbh Guanidingruppen aufweisende semi-organische Siliciumgruppen enthaltende Verbindungen
DE102013216781A1 (de) 2013-08-23 2015-02-26 Evonik Industries Ag Beschichtungsmassen
DE102013218134A1 (de) 2013-09-11 2015-03-12 Evonik Industries Ag Beschichtungsmittel enthaltend Polysiloxan-Quats
DE102013218981A1 (de) 2013-09-20 2015-03-26 Evonik Industries Ag Raumtemperaturhärtendes Silikon-Polyester-Bindemittel
DE102013218976A1 (de) 2013-09-20 2015-04-16 Evonik Industries Ag Hydroxylgruppenhaltiges Silikon-Polyester-Acrylat-Bindemittel
DE102014205806A1 (de) * 2014-03-28 2015-10-01 Evonik Degussa Gmbh Silan enthaltend jeweils mindestens zwei Alkoxygruppen sowie eine Guanidino- oder Harnstoffgruppe
DE102014217790A1 (de) 2014-09-05 2016-03-10 Evonik Degussa Gmbh Verfahren zur Herstellung von hydrosilylierbaren Eugenol-Polyethern und Eugenol-Polyethersiloxanen sowie deren Verwendung
EP3029087A1 (de) 2014-12-05 2016-06-08 Evonik Degussa GmbH Verfahren zur Herstellung von niedrigviskosen Polyethersiloxanen
EP3061442A1 (de) 2015-02-27 2016-08-31 Evonik Degussa GmbH Zusammensetzung enthaltend Rhamnolipid und Siloxan
ES2629050T3 (es) 2015-06-16 2017-08-07 Evonik Degussa Gmbh Trisiloxano órgano-modificado superdispersante biodegradable
JP6896381B2 (ja) 2015-07-10 2021-06-30 花王株式会社 毛髪化粧料
EP3168273B1 (de) 2015-11-11 2018-05-23 Evonik Degussa GmbH Härtbare polymere
EP3168251B1 (de) 2015-11-16 2019-02-06 Evonik Degussa GmbH Vernetzte polyglycerinester
DE102016207060A1 (de) * 2016-04-26 2017-10-26 Wacker Chemie Ag Wässrige Emulsionen aus Carbamato-funktionalisierten Organopolysiloxanen
PL3243858T3 (pl) 2016-05-11 2019-09-30 Basf Se Sieciowane polimery, sposoby ich wytwarzania i zastosowanie
EP3467052B1 (de) 2017-10-06 2022-04-13 Evonik Operations GmbH Wässrige dispersion enthaltend siliziumdioxid und trimethyl 1,6-hexamethylendiamin
EP3470475B1 (de) 2017-10-13 2021-01-27 Evonik Operations GmbH Härtbare zusammensetzung für beschichtungen mit anti-adhäsiver eigenschaft
EP3676322B1 (en) 2018-05-31 2021-08-11 Dow Silicones Corporation Method for making an amino-functional polydiorganosiloxane using a removable acid catalyst
CN111148794B (zh) 2018-05-31 2022-11-04 美国陶氏有机硅公司 使用可移除固体催化剂制备氨基官能聚二有机硅氧烷的方法
EP3611215A1 (de) 2018-08-15 2020-02-19 Evonik Operations GmbH Verfahren zur herstellung acetoxygruppen-tragender siloxane
EP3744774B1 (de) 2019-05-28 2021-09-01 Evonik Operations GmbH Verfahren zum recycling von silikonen
EP3744753B1 (de) 2019-05-28 2022-04-06 Evonik Operations GmbH Verfahren zur aufreinigung von acetoxysiloxanen
EP3744756B1 (de) 2019-05-28 2024-07-03 Evonik Operations GmbH Acetoxysysteme
EP3744754B1 (de) 2019-05-28 2024-10-02 Evonik Operations GmbH Verfahren zur herstellung acetoxygruppen-tragender siloxane
EP3744755B1 (de) 2019-05-28 2024-10-09 Evonik Operations GmbH Verfahren zur herstellung acetoxygruppen-tragender siloxane
EP3816247B1 (de) 2019-10-28 2022-12-07 Evonik Operations GmbH Härtermischung
EP3954740A1 (de) 2020-08-14 2022-02-16 Evonik Operations GmbH Entschäumerzusammensetzung auf basis von organofunktionell modifizierten polysiloxanen
FR3136167A1 (fr) * 2022-06-01 2023-12-08 L'oreal Procédé de traitement capillaire pour limiter la teneur en calcium des cheveux
FR3136159A1 (fr) * 2022-06-01 2023-12-08 L'oreal Composition cosmétique un ou plusieurs aminoacides, un ou plusieurs (poly)acides carboxyliques hydroxylés en C2-C8 et un ou plusieurs sels de (poly)acides carboxyliques hydroxylés en C2-C8, et procédé de traitement cosmétique
FR3136162A1 (fr) * 2022-06-01 2023-12-08 L'oreal Procédé de traitement capillaire comprenant l’application d’une composition comprenant des aminoacides et des (poly)acides carboxyliques hydroxylés, suivie d’un lavage des cheveux, et utilisation comme pré-shampoing

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1972330A2 (en) * 2008-06-13 2008-09-24 Clariant International Ltd. Cosmetic or pharmaceutical compositions comprising modified polysiloxanes with at least one carbamate group

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8501264D0 (en) 1985-01-18 1985-02-20 Ransomes Sims & Jefferies Plc Grass cutting attachment
DE68920775T2 (de) * 1988-05-17 1995-06-08 Dow Corning Ltd Behandlung von faserigen Materialien.
GB8911970D0 (en) 1989-05-24 1989-07-12 Dow Corning Method of treating fibrous materials
JP3859723B2 (ja) 1996-03-04 2006-12-20 オーエスアイ スペシャルティーズ インコーポレーテッド シリコーンアミノポリアルキレンオキシドブロックコポリマー
US6136938A (en) * 1999-03-05 2000-10-24 Dow Corning Corporation Silicone terpolymers containing dimethyl higher alkyl and repeating units
US6207781B1 (en) * 1999-08-20 2001-03-27 Dow Corning Corporation Polymerization of an organofunctional cocyclic siloxane
US6171515B1 (en) 1999-09-02 2001-01-09 Dow Corning Corporation Fiber treatment composition containing amine-, polyol-, functional siloxanes
JP2002167437A (ja) 2000-11-29 2002-06-11 Lion Corp グアニジン変性シリコーン及びその製造方法、並びに、それを用いた毛髪化粧料及び繊維処理剤
GB0120058D0 (en) 2001-08-17 2001-10-10 Dow Corning Polysiloxanes and their preparation
DE10153023A1 (de) * 2001-10-26 2003-05-15 Beiersdorf Ag Wirkstoffhaltige kosmetische Reinigungsemulsionen
DE10327871A1 (de) 2003-06-18 2005-01-05 Goldschmidt Ag Verwendung von Alkylguanidin-Verbindungen zur Behandlung und Nachbehandlung von Haaren
JP2006117606A (ja) * 2004-10-22 2006-05-11 Shiseido Co Ltd 毛髪化粧料
DE102005004704A1 (de) * 2005-02-02 2006-08-10 Goldschmidt Gmbh Guanidinogruppen-haltige Siloxane und deren Verwendung für kosmetische Formulierungen
JP5160921B2 (ja) * 2008-02-25 2013-03-13 花王株式会社 ウレタン結合含有基を有するオルガノポリシロキサン化合物
DE102008001788A1 (de) 2008-05-15 2009-11-26 Evonik Goldschmidt Gmbh Verwendung organomodifizierter Siloxanblockcopolymere zur Herstellung kosmetischer oder pharmazeutischer Zusammensetzungen
DE102010062156A1 (de) * 2010-10-25 2012-04-26 Evonik Goldschmidt Gmbh Polysiloxane mit stickstoffhaltigen Gruppen

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1972330A2 (en) * 2008-06-13 2008-09-24 Clariant International Ltd. Cosmetic or pharmaceutical compositions comprising modified polysiloxanes with at least one carbamate group

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of WO2012076293A2 *

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BR112013012305A2 (pt) 2016-07-12
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