WO2004069137A2 - Utilisation de copolymeres de polyamino- et/ou polyammonium-polysiloxane - Google Patents

Utilisation de copolymeres de polyamino- et/ou polyammonium-polysiloxane Download PDF

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Publication number
WO2004069137A2
WO2004069137A2 PCT/EP2004/050091 EP2004050091W WO2004069137A2 WO 2004069137 A2 WO2004069137 A2 WO 2004069137A2 EP 2004050091 W EP2004050091 W EP 2004050091W WO 2004069137 A2 WO2004069137 A2 WO 2004069137A2
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group
hair
groups
defined above
use according
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PCT/EP2004/050091
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German (de)
English (en)
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WO2004069137A3 (fr
Inventor
Horst Lange
Roland Wagner
Martin Kropfgans
Sabine Musiol
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Ge Bayer Silicones Gmbh & Co. Kg
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Priority claimed from DE2003104923 external-priority patent/DE10304923A1/de
Application filed by Ge Bayer Silicones Gmbh & Co. Kg filed Critical Ge Bayer Silicones Gmbh & Co. Kg
Publication of WO2004069137A2 publication Critical patent/WO2004069137A2/fr
Publication of WO2004069137A3 publication Critical patent/WO2004069137A3/fr

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    • 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
    • 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
    • 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
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences

Definitions

  • the invention relates to the use of linear or branched polyamino and / or polyammonium polysiloxane copolymers in the production and / or treatment of colored hair and compositions for the production and / or treatment of colored hair.
  • the invention relates in particular to the use of at least one polyamino and / or polyammonium polysiloxane copolymer (silicone quat) in various, preferably cosmetic formulations, in particular for the treatment of substrates containing keratin, such as human and animal hair, their cleaning and care with so-called rinse-off products, such as shampoos and hair rinses and with so-called leave-in products such as lotions, gels, pump sprays and aerosol sprays in the manufacture and / or treatment of colored hair.
  • these are formulations that reduce the washing out of dyes from tinted or dyed hair.
  • Another object of the invention is the use of a cosmetic formulation which contains at least one of the quaternary siloxanes 'Siliko ⁇ quats' to improve the conditioning of hair at the same time, to reduce the wet and dry combing forces of the hair, to increase the volume and to improve the shine of hair.
  • a cosmetic formulation which contains at least one of the quaternary siloxanes 'Siliko ⁇ quats' to improve the conditioning of hair at the same time, to reduce the wet and dry combing forces of the hair, to increase the volume and to improve the shine of hair.
  • other dyed keratin and non-keratin fibers can be treated with these formulations in order to reduce washout of dyes during washing and cleaning and at the same time to produce a pleasant handle.
  • polysiloxane-based, polyquaternary compounds can be used advantageously in hair care formulations (US 4,587,321, US 4,833,225, EP 282,720, US 6,240,929).
  • the use of such compounds leads to a silicone-typical soft, smooth and flat handle, the improvement of the dry and wet combing forces, the increase in the hair shine and the reduction of electrostatic charge on the treated hair.
  • the substrate is made hydrophobic.
  • An improved hydrophilicity of the finished substrate can e.g. can be achieved if alkylene oxide structures are introduced into the molecules.
  • J. Soc. Cosmet. Chem., 46, 231-245 discloses the use of amino-functional silicones to reduce the washout of color from colored hair while at the same time improving the wet and dry combing forces.
  • Preferred embodiments are here amino functional silicones and silicone resins (INCI: trimethylsiloxysilicate). Here, their color-retaining properties are described (INCI: trimethylsilylamodimethicone and amodimethicone). The abbreviations are used in INCI (The Cosmetic, Toiletry and Fragra ⁇ ce
  • GB 2138845 describes the use of laterally amino-functionalized silicones and their derivatives in hair colorants. An intensification of the color result of the hair coloring is described. A statement about the color-preserving effect of such
  • amino or ammonmium-functional siloxanes mentioned here have contiguous siloxane bonds in the main chain, as are given, for example, in the following definition for the compounds ⁇ 5 b2) which are not interrupted by other units in the main chain. This limits the possibility of adapting the solubility properties, hydrophilicity and the interaction with the substrate and the altered substrate properties that can be achieved thereby.
  • No. 6,432,145 describes a hair colorant which contains, inter alia, a cyclic silicone and a silicone elastomer.
  • a hair colorant which contains, inter alia, a cyclic silicone and a silicone elastomer.
  • the use of this silicone elastomer leads to a reduction in the washing out of the hair color from the hair colored with the formulation.
  • polyamino and / or polyammonium-polysiloxane copolymers are preferably those according to WO 02/10256, WO 02/10257, WO 02/10259 and DE-OS 100 36 533, DE-OS 100 36 522, DE -OS 100 36 532, EP 282 720, US 6,240,929, DE-OS 30 3340 708 and the unpublished DE 102 12470.1, DE 102 51 525.5 and DE 102 51 526.3 advantageous for formulations for care, conditioning and treatment, cleaning and care colored or to coloring substrates preferably keratin-containing substrates such.
  • di- and polyquaternated ⁇ siloxane systems with the inclusion of amino acid segments which are known from DE 100 36 522 and DE 100 36 532.
  • the present invention relates to polyamino and / or polyammonium polysiloxane compounds according to the definition of component b1) of claim 1, in particular compounds according to WO 02/10256, WO 02/10257, WO 02/10259 and DE-OS 100 36
  • Mixtures, emulsions and microemulsions in turn facilitate the production of cosmetic formulations according to the invention and additionally increase their storage stability.
  • the invention also relates to the manufacture and use of
  • the substrates are preferably colored keratin-containing substrates such as. B. human and animal hair.
  • Another object of the present invention was to incorporate these compounds directly into formulations for hair tinting, hair coloring or two-component formulations - color solution and developer solution - oxidative hair colors, which can be used during the coloring process in addition to excellent softness, volume, to increase the combability and the shine, and to wash out the color from and from colored or to be colored substrates containing keratin, such as e.g. B. to significantly reduce human and animal hair without compromising the stability of the formulation i.e. To influence storage stability and the color result negatively.
  • formulations for hair tinting, hair coloring or two-component formulations - color solution and developer solution - oxidative hair colors which can be used during the coloring process in addition to excellent softness, volume, to increase the combability and the shine, and to wash out the color from and from colored or to be colored substrates containing keratin, such as e.g. B. to significantly reduce human and animal hair without compromising the stability of the formulation i.e. To influence storage stability and the color result negatively.
  • the present invention relates to the use of at least one linear or branched polyamino and / or polyammonium polysiloxane copolymer b1) with the repeating units of the formula (I):
  • R in each case represents hydrogen or a monovalent organic radical
  • V is at least one component selected from the group consisting of V 1 , V 2 and V 3 , wherein
  • V 2 is selected from divalent, straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals having up to 1000 carbon atoms (the carbon atoms of the polysiloxane radical Z 2 defined below not being counted), which optionally one or more groups selected from
  • R 2 is hydrogen, a monovalent, straight chain, cyclic or branched, saturated, unsaturated or aromatic
  • radical V 2 may optionally be substituted by one or more hydroxyl groups, and the radical V 2 at least one group -Z 2 - of the formula
  • V 1 is selected from divalent, straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals with up to 1000 carbon atoms, optionally one or more groups selected from -O-,
  • Groups V 1 and V 2 may be the same or different
  • radical V 1 may optionally be substituted by one or more hydroxyl groups
  • V 3 represents a trivalent or higher-chain, straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radical having up to 1000 carbon atoms, which optionally has one or more groups selected from
  • R 2 is as defined above, -C (O) -, -C (S) -,
  • Z 3 where Z 3 is a trivalent or higher organopolysiloxane unit
  • said polysiloxane compound contains at least one group V 1 , V 2 or V 3 ,
  • polysiloxane compound contains at least one group -Z 1 -, -Z 2 - or Z 3 , and - that the trivalent and tetravalent radicals Q either the
  • Branching of the main chain formed from Q and V serve so that the valences which do not serve for binding in the main chain carry further branches formed from - [QV] units, or the trivalent and tetravalent radicals Q saturate with radicals V 3 within a linear main chain without branching, and in which the positive charges resulting from ammonium groups are neutralized by organic or inorganic acid anions, and their acid addition salts, and optionally at least one amino and / or ammonium polysiloxane compound b2) in the preparation and / or treatment of colored hair.
  • Q in the linear or branched polyamino and / or polyammonium polysiloxane copolymer b1) is preferably selected from the group consisting of: an amino unit of the formula:
  • R 2 is as defined above,
  • R 3 has the meaning of R 2 , where R 2 and R 3 can be the same or different, or R 2 and R 3 together with the positively charged nitrogen atom form a five- to seven-membered heterocycle which optionally also has one or more nitrogen, Can have oxygen and / or sulfur atoms,
  • R 5 , R 6 , R 7 can be the same or different and are selected from the group consisting of: H, halogen, hydroxyl group, nitro group, cyano group, thiol group, carboxyl group, alkyl group, mono-hydroxyalkyl group, polyhydroxy alkyl group, thioalkyl group, cyano-alkyl group, alkoxy group, acyl group, acetyloxy group, cycloalkyl group, aryl group, alkylaryl group, and groups of the type-NHR W , in which R w H, alkyl group, monohydroxyalkyl group, polyhydroxyalkyl group, acetyl group, Mean ureido group, and in each case two of the adjacent radicals R 5 , R 6 and R 7 with which they can form aromatic five- to seven-membered rings to the heterocycle, and R 8 has the meaning of R 2 , where R 8 and R 2 are the same or can be different.
  • the group Q consists of trivalent radicals of the formulas
  • the units V in the repeating units [QV] contain units V 1 which contain at least one esterified polyalkylene oxide structural unit of the general formulas:
  • A -CH 2 C (0) 0-, -CH 2 CH 2 C (0) 0-, -CH 2 CH 2 CH 2 C (0) 0-,
  • terminal oxygen atom of group A bind to the terminal -GH 2 group of group E, and the terminal carbonyl carbon atom of group A 'to the terminal oxygen atom of group E, each with the formation of ester groups.
  • the units V in the repeating units contain [QVj units V 1 , which are selected from:
  • the groups V consist of the repeating units V 2 and V 1 , and the molar ratio V 2 / V 1 is from 0.0005 to 1000, more preferably from 0.01 to 100, even more preferably from 0 , 1 to 10 more preferably from 0.8 to 1, 2.
  • the groups V consist of the repeating units V 2 and V 1 , and the molar ratio V 2 / V 1 is 1.
  • V 2 is a group of the formula -V 2 * -Z -V 2 *, in which Z 2 is as defined above and V 2 * is selected from divalent, straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals with up to 40 carbon atoms, optionally one or more groups selected from
  • -CONR 2 - in which R 2 is as defined above, can contain -C (O) - and -C (S) -,
  • radical V 2 * can optionally be substituted by one or more hydroxyl groups.
  • V 2 * is selected from groups of the formulas
  • group V in the repeating units [QV] of the polyamino and / or polyammonium polysiloxane copolymers b1) consists of repeating units of the formulas (II) and (III): (II):
  • A organic or inorganic acid anions
  • V 2 * is as defined above, V 1 is as defined above,
  • V 1 ' has the meaning of V 1 as defined above, but V 1 ⁇
  • V 1 ' where the nitrogen atoms in the formula (II) can optionally be protonated.
  • V 1 ' is selected from C1-C8-alkylene radicals and (C1-C8-alkyl) aryl (C1-C8-alkyl) radicals.
  • the polyamino and / or polyammonium-polysiloxane copolymers b1) with the repeating units - [Q-Vj- as chain end groups have a group of the formula -QR or -VR, in which R is as defined above ,
  • polyamino and / or polyammonium-polysiloxane copolymers b1) which have the end groups -Q-R are selected from the following formulas (IV) to (VIII):
  • radicals R are the same or different and are as defined above, and
  • R preferably has the meaning of R 2 , n is as defined above and is preferably n1,
  • A organic or inorganic acid anions
  • V 2 * is as defined above
  • V 1 is as defined above
  • V 1 ' has the meaning of V 1 as defined above, but V 1 ⁇
  • V 1 ' where the nitrogen atoms can optionally be protonated
  • radicals R are as defined above and can be the same or different, and R is preferably selected from radicals R 2 .
  • the linear or branched polyamino and / or polyammonium polysiloxane copolymer b1) have the formula RQV 2 -QR, where R, Q and V 2 are as defined above.
  • the linear or branched polyamino and / or polyammonium polysiloxane copolymer b1) of the formula RQV 2 -QR preferably have the following formula:
  • R, Q, n, V 2 * are as defined above.
  • the following additional components are optionally used in a mixture with component b1) and optional component b2): one or more nitrogen-free polysiloxane compounds a) (co-adjuvants), one or more silicone-free surfactants c ), - one or more coacervate phase images d), and one or more carrier substances e).
  • compositions defined above are used for temporary, semi-permanent or permanent hair coloring, for tinting and / or for the care and conditioning of colored hair.
  • this comprises the following steps: a) producing a premix by mixing at least one component b1) with one or more components selected from b2), a), c), d) and e) to form solutions, mixtures or emulsions and b) preparation of a composition for the preparation and / or treatment of colored hair by mixing the
  • premix Premixing a) and, if appropriate, further surfactants, auxiliaries and other additives or combining steps a) and b), in which the constituents are mixed with stirrers, dissolvers, kneaders, pumps, mixing screws, mixing nozzles and / or low and high-pressure emulsifiers.
  • the premix mentioned has the following composition:
  • Component b1) used according to the invention is at least one polyamino and / or polyammonium polysiloxane compound.
  • the polyamino and / or polyammonium polysiloxane compound b1) is a copolymer compound which has amino and / or ammonium repeating units and polysiloxane repeating units in the polymer main chain.
  • the amino units Q expediently contain secondary and / or tertiary nitrogen atoms (2 or 3 organic radicals on the neutral nitrogen atom).
  • the ammonium units expediently contain secondary, tertiary and / or quaternary positively charged nitrogen atoms (2, 3 or 4 organic radicals on the nitrogen).
  • Amino and / or ammonium repeating units can also serve as heterocyclic radicals integrated into the polymer chain via two nitrogen atoms.
  • component b2) is polysiloxane compounds which contain amino and / or ammonium groups in the side groups of the main polyorganosiloxane chain. That is, the amino and / or ammonium groups are not in the main chain of polyorganosiloxane repeat units. The difference can be illustrated as follows:
  • Components b1) and b2) can be present alone or together in the application according to the invention. In a preferred embodiment, however, component b1) is present alone, without component b2) in the formulation according to the invention. In a likewise preferred embodiment, both component b1) and component b2) are present side by side.
  • Components b1) or b2) can be present together in any ratio to one another.
  • Another preferred embodiment of b1) is characterized in that the unit Q is selected from the group
  • R 2 furthermore preferably stands for:
  • R 2 , R 3 , R 5 , R 6 , R 7 and R 8 are as defined above.
  • ni 20 to 1000, particularly preferably 20 to 300, especially 20 to 200. In a further preferred embodiment, ni is between 20 and 50, 50 to 80 or between 80 and 200. The number ni is the average degree of polymerization from M "of the diorganosiloxy units in group Z 2 .
  • the units V 2 are selected from a group of the formula
  • V 2 * is a divalent straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radical having up to 40 carbon atoms, which may be one or more Groups selected from -O-, -CONH-, -CONR 2 -, in which R 2 is as defined above, and -C (O) - and -C (S) -, and the radical V 2 * optionally by one or more hydroxyl groups can be substituted.
  • the branched or linear polysiloxane copolymer b1) used according to the invention can have the following repeating units:
  • V 2 * a divalent straight-chain, cyclic or branched, saturated, unsaturated C 3 to C ⁇ 6 hydrocarbon radical or aromatic C 8 to C 2 o hydrocarbon radical, which optionally contains one or more groups selected from -O-, -CONH-, -CONR 2 -, -C (O) -, -C (S) - may contain and may be substituted by one or more OH groups, wherein R 2 is as defined above.
  • V for a divalent straight chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radical with up to 16 carbon atoms, which has one or more groups selected from -O-, -CONH-, -CONR 2 -, wherein R 2 is as defined above , -C (O) -, -C (S) - may contain and may be substituted with one or more hydroxyl groups.
  • V 2 * is more preferably selected from groups of the formulas:
  • -CH CHCH 2 OC (0) CH 2 -
  • -CH CHCH 2 0C (0) CH 2 CH 2 -
  • CH3 -CH CHCH2 (OCH2CH2) v (OCH2CH) w OC (0) CH2-
  • CH3 -CH CHCH2 (OCH2CH2) v (OCH2CH) w OC (0) CH2CH2-
  • CH3 -CH CHCH2CH2 (OCH2CH2) v (OCH2CH) w OC (0) CH2-
  • CH3 -CH CHCH2CH2 (OCH2CH2) v (OCH2CH) w OC (0) CH2CH2-
  • R 2 preferably represents: H
  • R 4 straight-chain, cyclic or branched C 1 to C 18 hydrocarbon radical which is formed by one or more groups, may contain and by one or more OH groups may be substituted, preferably unsub--substituted C 5 to C 17 hydrocarbon radicals, which - selected from -O-, -NH-, -C (O) -, and -C (S) derived from the corresponding fatty acids or hydroxylated C 3 to C 17 residues, which can be attributed to hydroxylated carboxylic acids, especially saccharide carboxylic acids, and very specifically
  • the group Z 3 represents a three- or higher-order organopolysiloxane unit.
  • the branching unit V 3 can be constructed without silicon, ie without Z 3 . Examples of these include:
  • the branching unit V 3 can contain a trivalent or higher organopolysiloxane unit Z 3 , for example:
  • R 1 is as defined above.
  • Z 3 -containing branching unit V 3 is for example:
  • V 2 / V 1 can in itself assume any value.
  • the case is also included in which the polysiloxane compound of the formula (I) contains only V 2 units, the polysiloxane compound b1) thus has the formula - [QV 2 ] -.
  • the case in which the polysiloxane compound contains only V 1 units is also included according to the invention. In this case, however, the V 1 units must contain Z 1 siloxane units.
  • the polysiloxane compound of the formula (I) contains both V 2 and V 1 units.
  • R 1 is as defined above and n 2 means 0 to 19, preferably 0 to 10, especially 0 to 5, more particularly 0.
  • the number n 2 is the average degree of polymerization from M n of the diorganosiloxy units in the group Z 1 .
  • V 1 preferably stands for
  • R 9 represents a divalent, saturated or mono- or polyunsaturated, straight-chain or branched hydrocarbon radical having two to 25 carbon atoms, - (CH 2 ) uC (O) O - [(CH 2 CH 2 O) q - (CH 2 CH (CH 3 ) 0) r ] -C (O) (CH 2 ) u -
  • V 1 Preferred variants of V 1 are structures of the formula:
  • V1 are alkylene, alkenylene, alkynylene and aryl units, especially the structures:
  • -CH 2 C ⁇ CCH 2 -, -CH 2 CH CHCH 2 -, -CH (CH 3 ) CH 2 CH 2 -, and C6 to C22 aryl- or alkylarylene, such as:
  • V 1 is selected from polyalkylenotide units of the structures
  • Q 1 to 50, in particular 2 to 50, especially 1 to 20, very particularly 1 to 10, and 1 or 2
  • r 0 to 100, in particular 0 to 50, especially 0 to 20, very particularly 0 to 10, are preferred , as well as 0 or 1 or 2.
  • polyamino and / or polyammonium polysiioxane compounds b1) which, for. B. are described in WO 02/10257, WO 02/10259, DE-OS 100 36 522, DE-OS 100 36 532, DE-OS 100 36 533 and the unpublished DE application 102 12 470.1, are preferably suitable.
  • the connections according to US 6,240,929 can in principle also be used.
  • the linear or branched polyamino and / or polyammonium polysiloxane copolymers b1) of the formula - [QV-] and amino and optionally ammonium-polysiloxane compounds b2) preferably have as anions A " physiologically acceptable organic and inorganic radicals from the group consisting of chloride, bromide, hydrogen sulfate, sulfate, or organic residues from the group consisting of acetate, propionate, octa ⁇ oat, decanoate, dodecanoate, tetradecanoate, hexadecanoate, octadecanoate, oleate.
  • the compounds b2) are present in protonated form as amine salts.
  • the polysiloxanes of component b1) can be produced, for example, by a process as described in the prior art mentioned above, in particular in which
  • Reaction with the amino functions of the Ami ⁇ compound capable organic compounds are implemented, the molar ratio of the organic compounds being chosen so that the desired ratio V 2 ⁇ t 1 is obtained, b) at least two moles of an amine compound selected from a diamine compound and / or a primary or secondary monoamine compound, with one mole of a difunctional organic compound capable of reacting with the amino functions of the amine compound to form a diamine compound (monomer), which is then reacted with at least one
  • Amine compound selected from a diamine compound and / or a primary or secondary monoamine compound, and at least one further difunctional organic compound capable of reacting with the amino functions of the amine compounds is reacted
  • Variant a wherein at least one diamine compound, selected from a diamine compound and / or a primary or secondary monoamine compound, is reacted with at least two difunctional organic compounds capable of reacting with the amino functions of the amine compound, the molar ratio of organic compounds is selected so that the desired ratio V 2 / V 1 is satisfied, for example ⁇ 0.5, can be represented schematically, for example, as follows:
  • - [NV 2 -N] - may include, the latter resulting in two Q units and one V 1 and two V 2 units , and - [V 1 ] - and - [V 2 ] - are intended to represent monomers corresponding to the repeat units V 1 and V 2 , and - [N] - is a primary or secondary monoamine suitable for chain propagation,
  • At least one higher-alkylated amine or quaternary ammonium unit Q is formed from the - [NN] - and / or - [N] units, secondary or tertiary amino functions formed in the polymerization optionally after the polymerization in a separate one Step can be protonated or quaternized.
  • the formation of quaternary ammonium units is preferred.
  • Preferred examples of - [NN] - are as described in more detail below: piperazine and imidazole, preferred diamine units - [NV 1 -N] - include, for example: polymethylene diamines, tetramethyl-hexamethylene diamine, ⁇ , ⁇ -diamino-terminated, such as Polyethers such as Jeffamine, etc.
  • Preferred diamine units - [NV 2ft -Z -V 2 * -N] - include, for example, reaction products of ⁇ . ⁇ -dihydrogenpolydialkylsiloxanes with allylamines.
  • Preferred examples of - [N] - are, for example, dimethylamine, as described in more detail below.
  • the use of diamines - [NN] - is preferred per se.
  • Preferred - [V 1 ] monomers include, for example, epichlorohydrin, bis-chloroalkyl esters, bisepoxides or bisacrylates. Mixtures of the - [V 1 ] monomers mentioned, such as, for example, mixtures of epichlorohydrin, bis-chloroalkyl esters or bisepoxides, can also preferably be reacted.
  • Preferred - [V 2 ] monomers are monomers of the formula
  • V 2 repeat units are, in particular, co-diepoxy-terminated polydialkylsiloxanes.
  • Variant b) can be carried out with diamines, - [N-N] - as well as suitable monoamines - [N] - and can be represented schematically, for example, as follows:
  • Step 1) 2 - [NJ- + - [V 2 ] - or - [V 1 ] - ⁇ - [NVN] - or - [NV 2 -N] - Step 2.1): - [NV 2 -N] - + - [V 1 ] - + - [N] - ⁇ , step 2.2): - [NV 1 -N] - + - [V 2 ] - + - [N] - ⁇ , wherein this variant, as mentioned above, can only be carried out with primary or secondary monoamines and, with regard to the monomer units used - [N] -, - [V 1 ] - and - [V 2 ] - what has been said for step a) applies.
  • Variant c can be represented schematically, for example, as follows:
  • Step 1) - [NN] - + - [V 1 ] - ⁇ - [NN- (V 1 -NN) ⁇ ] - Step 2): - [NN- (V 1 -NN) J- + - [V 2 ] - ⁇ with regard to the preferred monomer units - [NN] -, -ry 1 ] - and -ry 2 ] - what has been said for step a) applies.
  • Variant c2) Step 1): - [N] - + - [V 1 ] - ⁇ - [N- (V 1 -N) protest] - Step 2): - [N- (V 1 -N) ⁇ ] - + - [V 2 ] - ⁇ with respect to the preferred monomer units - [N] ⁇ , - [V 1 ] - and - [V 2 ] - what has been said for step a) applies.
  • Variant d can be represented schematically, for example, as follows:
  • Step 1) - [V 1 ] - + - [NN] - ⁇ -ry 1 - (NNV 1 ) J- Step 2): - [ ⁇ - (NNV 1 ) *] - + - [V 2 ] - + - [N] - or - [NN] - ⁇ with respect to the preferred monomer units - [NN] -, -ry 1 ] - and - [V 2 ] - what has been said for step a) applies.
  • Step 1) - [V 1 ] - + - [N] - -> - [V 1 - (NV 1 ), j- Step 2): -ry 1 - (NV 1 ), J- + - [V 2 ] - + - [N] - or - [NN] - -> with respect to the preferred monomer units used - [N] -, - [NN] -, -ry 1 ] - and -ry 2 ] - what has been said for step a) applies.
  • mixtures of monoamines - [N] - and diamines - [NN] - can also be used.
  • the functional groups of the difunctional compounds capable of reacting with amino functions are particularly preferably selected from the group consisting of epoxy groups and haloalkyl groups.
  • the starting point for the syntheses of the polysiloxane copolymers b1) used according to the invention are ⁇ , ⁇ -Si-H-functionalized siliconoxanes of the general structure
  • R 1 has the meaning given above and n, depending on the desired repeating unit, is V 1 or V 2 , n 2 or ni, which are as defined above.
  • these siloxanes can be prepared by known processes, for example by equilibration (Silicone, Chemistry and Technology, Vulkan-Verlag, Essen 1989, pp. 82-84).
  • the preparation of the precursors of the structural elements V 2 * and Q can, for. B. done in two ways.
  • Suitable starting materials for the production of reactive intermediates are, for example, halogenated alkenes or alkanes, especially allyl chloride, allyl bromide, chlorpropine and chlorobutin, unsaturated halocarboxylic acid esters, especially chloroacetic acid allyl esters, chloroacetic acid propargyl esters, 3-chloropropionic acid allyl esters and 3-chloropropylpropylene acid propylene acid, epoxy allyl epoxyhexylpropoxy acid propylene oxyphenyl propylene acid and epoxy-allyl epoxy propylene acid, glycidyl ether.
  • the general implementation of hydrosilylation with representatives of the groups of substances mentioned is also known (B.
  • Suitable representatives are N, N-dialkylamines, for example dimethylamine, diethylamine, dibutylamine, diethanolamine and N-methylgiucamine, cyclic secondary amines, for example morpholine and piperidine, aminoamides which carry secondary amino functions, for example the reaction products of diethylene triamine or dipropylenetriamine with lactones, such as -Butyrolactone, gluconic acid ⁇ -lactone and glucopyranosylarabonic acid lactone (DE-OS 43 18 536, Examples 11a, 12a, 13a), or secondary-tertiary diamines, such as N-methylpiperazine. It is particularly preferred to use corresponding imidazole or pyrazole derivatives, especially imidazole and pyrazole, for introducing tertiary amino functions.
  • Particularly suitable as partners for the epoxy derivatives used in one embodiment are the secondary-tertiary diamines mentioned, and also imidazole and pyrazole.
  • the alkylations can be directed regioselectively and without additional effort to the nitrogen atoms carrying hydrogen atoms.
  • the amines are used in a ratio of 1 ⁇ ⁇ secondary amino groups: reactive groups 10 10, preferably 1 to 3, especially 1 to 2, very particularly 1. Excess amine may need to be removed.
  • an alkylating or quaternizing, difunctional monomer corresponding to the repeating unit V 1 can, for example, jV 1 ] -, selected for example from bisepoxides, epichlorohydin, bishalogenalkyl compounds, can be used. It goes without saying that different groups V 1 can result in the prepolymer and in the connecting link between prepolymer and ⁇ , ⁇ -ditertiary aminosiloxane structure.
  • a preliminary provision of prepolymers terminated by amino groups, such as - [N- (V 1 -N) -] - opens up the possibility of carrying out the copolymer formation directly with suitable reactive intermediates, for example epoxy derivatives. It is also preferred to submit the reactive intermediates and the starting components for the construction of - [V 1 - (QV 1 ) > J- together and then to react them. Finally, it is possible to gradually dose the reactive intermediates into the components presented to build -ry 1 - (QV 1 ) ⁇ ] - over a period of time or, conversely, to gradually add these components to the reactive intermediate.
  • the overall stoichiometry is chosen such that the sum of the amino functions and the groups reactive with them is approximately 1: 1 is.
  • Suitable difunctional monomers on which the repeating units V 1 are based - [V 1 ] - are, for example, the halocarboxylic acid esters of the polyalkylene oxide diols.
  • Preferred starting materials for their synthesis are low molecular weight, oligomeric and polymeric alkylene oxides of the general composition
  • q and r have the meanings given above, and are statistical or block-like units.
  • Preferred representatives with regard to the alkylene oxide block are ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, the oligoethyl ⁇ n-glycols with molecular weights of 200 to 10,000 g / mol, especially 300 to 800, and 1,2-propylene glycol, 1,3-propylene glycol and dipropylene glycol.
  • the polyalkylene oxide units used can also be introduced via the ⁇ , ⁇ -dihalogen compounds. These are made from the oligomeric and polymeric alkyl oxides of the general composition
  • q and r have the meanings given above, for example accessible by chlorination of the hydroxyl groups with SOCI 2 (Orga ⁇ ikum, Organic Chemistry Basic Internship, 17th Edition, VEB German Publishing House of Sciences, Berlin 1988, pp. 189-190).
  • Mono-, di- or polyhydroxy-functional units as group V 1 can be introduced starting from epoxy derivatives.
  • Commercial examples are 1-chloro-2,3-epoxypropane, the glycerol-1,3-bis-glycidyl ether and diethylene glycol diglycidyl ether and neopentyl glycol diglycidyl ether.
  • Suitable starting materials for installation are, for example, the corresponding ⁇ , ⁇ -diepoxides or ⁇ , ⁇ -di (monohalogen carboxylic acid) ester structures.
  • care must be taken to ensure that one mole of H + per mole of epoxide / tertiary amine is added for alkylation of tertiary amino groups.
  • suitable amines as starting components for the formation of Q in the repeat unit -ry 1 - (QV 1 ) ⁇ ] - also determines the molecular structure to a large extent.
  • di-tertiary amines (corresponding to - [NN] -), for example N, N, N ', N'-
  • secondary-tertiary diamines for example N-methylpiperazine
  • N-methylpiperazine opens the way to repeat units - [V 1 - (QV 1 ) J-, in which tertiary and quaternary amine or ammonium structures are present in a 1: 1 ratio.
  • a partial or complete subsequent quaternization of remaining tertiary amino structures is a preferred variant for setting a desired high density of the quaternary ammonium groups.
  • the corresponding aromatic amines imidazole or pyrazole lead to products with a delocalized charge.
  • comb-like structures can be built up for which the degree of quaternization can be selected during a final alkylation.
  • the alkylations can also be set to degrees of quaternization of on average less than one quaternary ammonium group per repeating unit -ry 1 - (QV 1 ) J-.
  • QV 1 quaternary ammonium group per repeating unit
  • the di-secondary amines initially provide poly-tertiary amino-modified siloxane copolymers or prepolymers which are quaternized in a final reaction to - [V 1 - (QV 1 ) ⁇ ] - can.
  • Suitable quaternizing agents are the generally known groups of substances such as alkyl halides, halocarboxylic esters, epoxy derivatives in the presence of H + and dialkyl sulfates, especially dimethyl sulfate.
  • non-commercially available secondary amines are prepared starting from the corresponding diprimary amines, for example hexamethylenediamine, by alkylation with epoxides, such as, for example, ethylene oxide, propylene oxide, isopropylglycidyl ether, using the different reaction rates of primary and secondary amines. It had already been shown that within the scope of the invention it is possible to introduce siloxane chains Z 1 into the structure of V 1 .
  • the reactive intermediates ⁇ , ⁇ -diepoxides and ⁇ , ⁇ -bis (mo ⁇ ohalogenecarboxylic acid) esters were named as examples of suitable starting materials.
  • the quaternization reactions are preferably carried out in water, polar organic solvents or mixtures of the two components mentioned.
  • Suitable are e.g. Alcohols, especially methanol, ethanol, i-propanol and n-butanol, glycols such as ethylene glycol, diethylene glycol, triethylene glycol, the methyl, ethyl and butyl ethers of the glycols mentioned, 1, 2-propylene glycol and 1, 3-propylene glycol, Keto ⁇ e, such as acetone and methyl ethyl ketone, esters, such as ethyl acetate, butyl acetate and 2-ethylhexyl acetate, ethers, such as tetrahydrofuran and nitro compounds, such as nitromethane.
  • the choice of solvent depends essentially on the solubility of the reactants, the desired reaction temperature and any reactivity that may interfere with the reaction.
  • the reactions are carried out in the range from 20 ° C. to 130 ° C., preferably 40 ° C. to 100 ° C.
  • the molecular weight is expediently limited.
  • the polyorganosiloxane polymers can, in addition to the terminal groups naturally resulting from the reaction of the monomeric starting materials, also from monofunctional chain terminators, such as trialkylamines etc. and e.g. resulting ammonium, amino, ether or hydroxy end groups. All cases of end stop Q * are intended to be covered by the definition -Q-R and / or -V-R mentioned above, wherein Q, V and R are as defined above and R can be replaced by hydrogen.
  • the polyamino and / or polyammonium polysiloxane compounds b1) used can be solid or liquid at 25 ° C.
  • They can have melting points up to 250 ° C, but are water-soluble or dispersible. Their solubility is preferably more than 1 g / l at 25 ° C.
  • amino and / or ammonium polysiloxane compounds b2) can be used as additional component b2). We have included these above, amino or ammonium groups only in the side groups.
  • the amino and / or ammonium polysiloxane compounds b2) are preferably polysiloxanes bearing primary and / or secondary and / or tertiary amino groups in the side groups, in which the amino groups optionally protonated or quaternized, and which may optionally contain additional hydrophilic groups.
  • the amino or ammonium groups mentioned are preferably bonded to the siloxane skeleton via carbon.
  • the amino and / or ammonium polysiloxane compounds b2) mentioned are preferably polyalkylsiloxanes with aminoalkyl or aminoarylsiloxane units.
  • the aminoalkyl units can be bound both to the difunctional, trifunctional or monofunctional end groups and can be part of other oxygen-containing side groups, in particular of polyether side groups. Examples are SF 1708, Baysilone OF 7747 from GE Bayer Silicones GmbH & Co KG.
  • aminopolysiloxanes b2) mentioned are linear or branched polysiloxanes which are composed of siloxy units which are selected from the group consisting of:
  • R 11 represents organic radicals which may be the same or different from one another, with the proviso that at least one of the
  • R 11 contains at least one nitrogen atom.
  • the substituents R 11 are preferably selected from the group consisting of: straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radical with up to 200
  • Carbon atoms optionally one or more groups selected from -O-, -NR 2 -, where R 2 is as defined above,
  • R 1 and m are as defined above, a polyether radical having up to 20,000 carbon atoms, the
  • R 1 is preferably alkyl, in particular methyl.
  • Preferred radicals R 11 which have nitrogen are, for example:
  • amino or ammonium group-containing radicals R 11 are, for example:
  • the nitrogen-containing radical R 11 is preferably aminopropyl or aminoethylaminopropyl. Further preferred nitrogen-containing radicals R 11 are formed from the reaction of glycidyloxypropylsiloxanes with mono- or dialkylamines. Preferred compounds as component b2) are therefore, for example, aminopolysiloxanes which result from the reaction of epoxyalkylsiloxanes with ammonia, primary or secondary amines, such as those obtained from the reaction of glycidyloxypropylsiloxanes with mono- or dialkylamines.
  • Preferred alkoxy radicals for R 11 are methoxy, ethoxy, propoxy, isopropoxy, butoxy, hexyloxy and cyclohexyloxy.
  • Preferred polyether radicals having up to 20,000 carbon atoms, which can optionally carry one or more amino, mono- or dialkylamino or arylamino groups, for R 1 include, for example:
  • CH3 -CH CHCH2 (OCH2CH2) v (OCH2CH) w OH
  • CH3 -CH CHCH2 (OCH2CH2) v (OCH2CH) w OC (0) CH3
  • CH3 -CH CHCH2 (OCH2CH) V (OCH2CH) W OCH3
  • CH3 -CH CHCH2CH2 (OCH2CH2) v (OCH2CH) w OH
  • CH3 -CH CHCH2CH2 (OCH2CH2) v (OCH2 ⁇ H) w OC (0) CH3
  • CH3 -CH CHCH2CH2 (OCH2CH 2 ) v (OCH2CH) w OCH3
  • saccharide-containing organic radicals for R are:
  • the additional hydrophilizing groups which may be present are preferably those which are derived from polyalkylene oxides and saccharides.
  • saccharide-containing polysiloxanes can be found e.g. in DE 4 318 536, DE 4 318 537.
  • the average degree of polymerization of the polysilox content of the aminopolysiloxanes b2) used according to the invention, which results from Mn, is advantageously from 1 to 3000, preferably from 200 to 1000.
  • the ratio of the nitrogen-free polyorganosiloxane units to the nitrogen-containing polyorganosiloxane units in the aminopolysiloxanes b2) used according to the invention is advantageously from 1: 1 to 500: 1.
  • the ratio of the polyether- or saccharide-containing polyorganosiloxane units to the other polyorganosiloxane units can be from 0 to 1.
  • the compounds b1) and b2) described above can be used as a pure substance, solution, mixture, emulsion or microemulsion in the form of liquids, creams or pastes as a starting material for the production of suitable cosmetic formulations of different viscosities used in accordance with the invention.
  • the silicones are also called co-adjuvants or silicones of category 2) under conditioning agents, which are known from the prior art.
  • the process for the production of formulations for the treatment of substrates expediently consists of the steps: a) preparation of a premix in the form of solutions, mixtures or emulsions from the compositions according to the invention and b) production of a further mixture using the premix a) and addition of any further Te ⁇ side.Hilfsstoffe and other additives or combining steps a) and b), in which the mixing of
  • premixes or intermediate mixtures can preferably be mixtures in the form of solutions, pastes, creams or other forms of emulsions or dispersions.
  • the production and use of microemulsions with an average particle diameter of 10 to 200 nm in cosmetic formulations is particularly preferred.
  • the formulations according to the invention can be prepared in various dosage forms for hair treatment.
  • compositions containing quaternary polysiloxane compounds b1) are preferred as cosmetic formulations for the treatment of keratin-containing substrates, such as, for. B. human and animal hair or skin applied as an alcoholic or polyalcoholic solution or as an emulsion.
  • keratin-containing substrates such as, for. B. human and animal hair or skin applied as an alcoholic or polyalcoholic solution or as an emulsion.
  • auxiliary materials and the mixing process used in the production clear, cloudy and white formulations are obtained.
  • composition of the solutions Premixes and mixtures.
  • Alcoholic and polyalcoholic solvents and their mixtures with water, oil-like substances as carriers e) and conventional silicones (including polydimethylsiloxanes), the latter as nitrogen-free polysiloxane compound a) are preferably suitable for producing the solutions and mixtures used according to the invention.
  • Especially preferred solvents as carriers e) are ethanol, isopropanoi, ethylene glycol and ethylene glycol ether, polyethylene glycols and their ethers, propylene glycol and propylene glycol ether, polypropylene glycols and their ethers and glycerin.
  • Particularly preferred oil-like substances as carriers e) are mineral oil products and oils of vegetable, animal and synthetic origin.
  • Particularly preferred silicones as component a) are cyclic and linear polydimethylsiloxanes and their mixtures such as, for. B. (INCI) Cyclomethicone, cyclotetra- siloxane, Cyclopentasiloxane, Cyclohexasiloxa ⁇ e, Dimethicone with a viscosity range of 0.65 to 60,000,000 mPas at 25 Q C and dimethiconol having a viscosity range from 10 to 60,000,000 mPas at 25 ° C that do not fall under the definition of compounds b1) and b2) (see definition below).
  • Preferred solutions and mixtures have the following composition in% by weight:
  • compositions of the emulsions are provided.
  • emulsions can contain adjuvants such as e.g. B. inorganic and organic acids, bases and buffers, salts, thickeners, stabilizers for emulsions such as ⁇ . B.
  • adjuvants such as e.g. B. inorganic and organic acids, bases and buffers, salts, thickeners, stabilizers for emulsions such as ⁇ . B.
  • quaternary polysiloxanes according to the invention can also serve as emulsifiers in the preparation of emulsions.
  • Formulations in the manufacture and / or treatment of colored hair contain the following components in% by weight:
  • microemulsions with a high active content of polyamino and / or polyammonium-polysiloxane copolymers b1) is particularly preferred since, in addition to the possibility of producing clear cosmetic formulations, these also have the advantage of simple process incorporation (“cold process”) It is possible to use the quaternary polysiloxanes according to the invention in the preparation of microemulsions in the form of the solutions and mixtures described above.
  • a preferred active content of quaternary polysiloxanes b1) in the emulsion is between 5 and 60%, particularly preferably are 10-50%.
  • a very particularly preferred microemulsion consists of the following, but not limiting, parts by weight of the invention: 20 - 50% polyamino and / or polyammonium
  • Cosmetic formulations here include so-called “rinse-off” products such as, for example, 2-in-1 shampoos, body wash and hair rinses for treating hair during and after cleaning or after dyeing or treating hair before bleaching or curling or uncrimping, as well as so-called “leave-in” products such as hair treatments, skin care creams, hairdressing creams, hair gels, hair styling products, hair fixatives, hair sprays, pump sprays, blow-drying agents and blow-drying agents.
  • the formulations also include hair colorants, which can be divided into 3 types - permanent, semi-permanent and temporary hair colorants - depending on the wash resistance of the color result obtained.
  • the term hair includes all fibers containing keratin, but especially human hair.
  • ingredients of the formulations amino- and ammonium group-free silicones, silicone-free surfactants, auxiliary substances such as coacervate formers and carriers, and ingredients for hair colorants.
  • auxiliary substances such as coacervate formers and carriers
  • ingredients for hair colorants can be used either alone or in combination with other ingredients and stands for additional functions in the formulations, which increase the volume, combability and gloss and reduce the washout of the color from and from colored keratin-containing substrates such as human and animal hair and contain at least one quaternary polysiloxane compound.
  • the abbreviations are explained in the INCI (The Cosmetic, Toiletry and Fragrance Association Washington DC or at http: //www.cosrT.etic- world.com/inci /i ⁇ cialf.htm).
  • Silicone conditioning agents (co-adjuvants)
  • the silicones encompassed here according to component a) are cyclic, linear and branched polydimethylsiloxanes with a viscosity of 0.65-200,000,000 mPa.s at 25 ° C. and also mixtures thereof, such as, for example, octaorganocyclotetrasiloxanes, octamethylcyclotetrasiloxanes, deca-organocyclopentasiloxanes, organodasiloxanes, and dodecaorganocyclines, with dodecaorganocyclocycles being preferred Methyl means, such as SF 1173, SF 1202, SF 1217, SF 1204 and SF 1258 from GE Bayer Silicones, dimethicones such as the Baysilone M oils (M3 to M 2,000,000), SE 30, SF 1214, SF 1236, SF 1276 and CF 1251 from GE Bayer Silicones and Dimethiconole such as Baysilone Abhesive
  • Organofunctional silicones such as alkyl-, aryl-, arylalkyl-, phenyl-, fluoroalkyl- and polyether-modified silicones such as types SF 1632, SF 1642, SF 1555, Baysilone CF 1301, Baysilone PK 20, FF 157, are also suitable.
  • anionic surfactants are suitable, by way of example but not by way of limitation, as a constituent of the formulations: alkyl sulfates, alkyl ether sulfates, alkaryl sulfates, olefin sulfonates, alkyl amide ether sulfates, acyl isethionates, acyl glutamates, alkyl ether carboxylates, methyl taurides and taurides, sarcosides, sulfosuccinates and protein ether phosphates, protein ether phosphates.
  • the free acids and their alkali metal salts, magnesium, ammonium and mono-, di- and triethanolamine salts can be used here.
  • the alkyl and acyl groups typically contain 8-18 C atoms and can be unsaturated.
  • the alkyl ether sulfates, alkyl amide ether sulfates, alkyl ether carboxylates and alkyl ether phosphates can contain 1-10 ethylene oxide or propylene oxide or a combination of ethylene oxide and propylene oxide units.
  • amphoteric surfactants are suitable as part of the formulations by way of example but not by way of limitation:
  • Alkyl betaines alkyl amido betaines, sulfobetaines, acetates and diacetates, imidazolines, propionates and alkylamine oxides.
  • the alkyl and acyl groups contain 8-19 C atoms.
  • Nonionic surfactants are nonionic surfactants:
  • nonionic surfactants are suitable as part of the formulations, by way of example but not by way of limitation:
  • Alkyl ethoxylates aryl ethoxylates, ethoxylated esters, polyglycol amides, poly sorbates, glycerol fatty acid ethoxylates, alkyl phenol polyglycol ethers and sugar surfactants such as e.g. Alkylglycosides.
  • cationic surfactants With cationic surfactants, a distinction is made between pure cationic surfactants and cationic polymers.
  • nonionic surfactants are suitable as part of the formulations, by way of example but not by way of limitation:
  • Cationic polymers are used in particular as coacervaiphase formers d).
  • cationically modified polymers are used in addition to the pure cationic surfactants.
  • US 5,977,038 and WO 01-41720 A1 provide a comprehensive description of these polymers.
  • Cationic polyacrylamides, cationic protein derivatives and hydroxyalkyl cellulose ethers are preferred and cationic guar derivatives.
  • Cationic guar derivatives with the CTFA name guar hydroxypropyltrimonium chloride are particularly preferred. These types are available under the trade names Cosmedia Guar C 261 (Henkel), Diagum P 5070 (Diamalt), Jaguar C types and Jaguar EXCEL from Rhodia.
  • auxiliaries are suitable as part of the formulations: inorganic and organic acids, bases and buffers, salts, alcohols such as e.g. Ethanol, isopropanoi, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, glycol ether and glycerin, thickeners, stabilizers for emulsions such as B. xanthan gum, refatting agents, preservatives, foam stabilizers, defoamers, pearlescent and opacifiers such as e.g.
  • Glycol distearates and titanium dioxide collagen hydrolyzate, keratin hydrolyzate, silk hydrolyzate, anti-dandruff agents such as e.g. Zinc pyrithio ⁇ , salicylic acid, selenium disulfide, sulfur and tar preparations, polymeric emulsifiers, vitamins, dyes, UV filters, bentonites, perfume oils, fragrances, styling polymers, moisturizers, plant extracts and other natural or nature-identical raw materials.
  • anti-dandruff agents such as e.g. Zinc pyrithio ⁇ , salicylic acid, selenium disulfide, sulfur and tar preparations, polymeric emulsifiers, vitamins, dyes, UV filters, bentonites, perfume oils, fragrances, styling polymers, moisturizers, plant extracts and other natural or nature-identical raw materials.
  • Dyes and other ingredients of hair dyes are described in: A. Domsch, Die kosmetischen Preparate, Publishing House for Former Industry, 4th edition, 1992. Dyes are described in: Regulation on Cosmetics (Cosmetics Regulation), Federal Law Gazette 1997, Part I S . 2412, ⁇ 3 and Appendix 3 and in Europea ⁇ Community (EC) Directive, 76/68 / EEC, Annex IV. In the following, hair dye is divided into permanent, semi-permanent and temporary hair dye.
  • m- and p-phenylenediamines diaminobenzenes
  • their N-substituted derivatives and salts N-substituted derivatives of o-phenylenediamine, o-, m- and p-toluenediamines (methyl-diaminobenzenes), their N- substituted derivatives and salts
  • p-aminodiphenylamine hydrochloride and sulfate, o-, m- and p-aminophenol and hydrochloride, 2,4-diaminoisosulfate (4-metho-cy-m-phenylenediamine sulfate), o-chloro-p -phenylenediamine sulfate, picaminic acid (2,4-dinitro-6-aminophenol) and 2,4-dinitro-1-naphtol sulfonic acid and their sodium salt.
  • the following coupling components are suitable as part of the formulations: hydrochi ⁇ on (1,4-dihydroxybenzene), resorcinol (1,3-dihydroxybenzene), pyrocatechol (1,2-dihydroxybenzene), ⁇ -naphthol (1-hydroxynaphthalene), Pyrogallol (1, 2,3-trihydroxybenzene) and 2,6-diaminopyridine.
  • Oxidation bases and coupling components with surfactants are usually incorporated into oil-in-water emulsions, but simple solutions or shampoos are also known as formulations.
  • the formulations also contain antioxidants such as e.g. Sodium sulfite, sodium dithionite, ascorbic acid or thioglycolic acid to stabilize the precursors and are mixed with alkaline substances such as e.g. Ammonia adjusted to a pH value between 8 and 12 (preferably 9-11).
  • surfactants are added as wetting agents, complexing agents for heavy metals, fragrances to mask the smell of ammonia, conditioners to improve the feeling on the hair and to protect the hair, and solvents such as ethanol, ethylene glycol, glycerol or benzyl alcohol are added.
  • permanent hair colorants are offered as 2 component systems consisting of a color solution, cream or shampoo as described above and the developer solution.
  • the developer solution contains between 6-12% hydrogen peroxide and can optionally also be mixed with components of the formulation containing the color components. However, the peroxide solution must be carefully stabilized.
  • Semi-permanent hair dyes Semi-permanent dyes have been developed to maintain the color for shampooing 6-10 times. So-called direct dyes are used, which essentially belong to the group of nitro, azo and anthraquinone dyes. These dyes are small enough to penetrate the hair. Formulations typically used are solutions, creams, shampoos or aerosol foams. The composition is comparable to the formulations containing the color component, which are used as permanent hair colors.
  • temporary dyeings In contrast to semi-permanent hair dyes, temporary dyeings, also called tints, contain larger dye molecules that are unable to penetrate the hair. They are designed to maintain the color for 1-6 washes. Typically, azo and basic dyes and azine and thiazine derivatives are used here. The same applies to the composition of the formulations as for semi-permanent and permanent hair dyes. Dyes and other ingredients of hair dyes are described in: A. Domsch, Die kosmetischen Preparate, Publishing House for Former Industry, 4th edition, 1992. Dyes are described in: Regulation on Cosmetics (Cosmetics Regulation), Federal Law Gazette 1997, Part I S . 2412, ⁇ 3 and Appendix 3 and in European Community (EC) Directive, 76/68 / EEC, Annex IV.
  • EC European Community
  • a typical shampoo formulation used according to the invention for the care and conditioning of hair consists of the following components in% by weight:
  • a typical shampoo formulation used according to the invention consists of the following components in% by weight:
  • 0.1-12% component b1) and optionally b2) (approx. 43.5% emulsion in water with nonionic emulsifiers)
  • a typical hair conditioner used according to the invention for the care and conditioning of hair consists of the following components in% by weight:
  • Another typical hair conditioner used according to the invention consists of the following components in% by weight:
  • component b1) 0.5-15% component b1) and optionally b2) (as an approximately 43.5% emulsion in water with nonionic emulsifiers)
  • a typical hair care cure for the care and conditioning of hair used according to the invention consists of the following components in% by weight:
  • a typical hair care treatment used according to the invention consists of the following components in% by weight:
  • component b1 1-20% component b1) and optionally b2) (as approx. 43.5% emulsion in water with nonionic emulsifiers)
  • citric acid 0-2% sodium chloride to 100% supplemented by water.
  • a typical hair care treatment used according to the invention consists of the following components in% by weight:
  • 2-5% component b1) and optionally b2) (as an approx. 43.5% emulsion in water with nonionic emulsifiers)
  • 0-5% silicone conditioners (co-adjuvants)
  • a typical dye-containing formulation used according to the invention for temporary, semi-permanent or permanent hair coloring consists of the following components in% by weight:
  • hair dye precursor or dyes depending on the desired hair color
  • silicone conditioning agents 0-10% excipients on 100% water
  • a special color cream according to the invention, but not limiting the invention, for permanent hair coloring consists of the following components in% by weight:
  • component b1) 0.1-10% component b1) and optionally b2) (as an approximately 20% emulsion in water with nonionic emulsifiers)
  • amphoteric surfactant 0-10% non-ionic surfactant
  • silicone conditioning agents 0-10% auxiliaries on 100% water
  • a typical color solution used according to the invention for permanent hair coloring consists of the following components in% by weight:
  • component b1) 0.1-10% component b1) and optionally b2) (as an approximately 20% emulsion in water with nonionic emulsifiers)
  • a typical developer formulation used according to the invention for permanent hair coloring consists of the following components in% by weight:
  • anionic surfactant 0-10% amphoteric surfactant
  • silicone conditioning agents 0-10% auxiliaries in 100% water
  • a typical developer cream for permanent hair dyeing used according to the invention consists of the following components in% by weight:
  • component b1) 0.1 -5% component b1) and optionally b2) (as an approx. 20% emulsion in water with non-ionic emulsifiers) 10-30% hydrogen peroxide (30%)
  • solutions or mixtures according to the invention are preferably suitable for the production of cosmetic formulations for coloring hair or for the nourishing and color-preserving treatment of colored hair, such as:
  • the treatment, conditioning, cleaning and / or care of colored or to be colored substrates i.e. the formulations containing at least one linear or branched polyamino and / or polyammonium polysiloxane copolymer b1) can be used in particular for the cleaning, care and conditioning of fibrous or sheet-like substrates and if these are colored and their color impression is to be largely retained , the treatment conditioning, cleaning and care of keratin-containing substrates, since they are used as cleaning agents for wool, for washing and / or increasing the volume and / or the combability and / or the gloss and / or for reducing the washout of the color from and from dyed or from substrates to be colored at the same time, such as keratin are suitable for human and animal hair.
  • the hair dye formulated with it also improves the softness and / or to reduce the wet and dry combing forces and / or to increase the gloss and / or to increase the hair volume and / or to reduce the washing out of dyes from and from tinted and dyed hair;
  • rinse-off products such as, for example, 2-in-1 shampoos, body wash and hair rinses for the aftertreatment of hair after cleaning or dyeing or the pretreatment of hair before bleaching, curling or uncrimping, and so-called "Leave-in” products, such as hair treatments, skin care creams, hairdressing creams, hair gels, hair styling products, hair setting agents, hair sprays, pump sprays, blow-drying agents or hair-setting agents;
  • compositions according to the invention are preferably suitable for the compounds b1), in particular for the treatment, cleaning and / or care of colored or to be colored substrates.
  • 15 water can be diluted in a ratio of 100 parts water to one part emulsion.
  • Example 4 4a 49.33 g of 2-propanol, 3.1 g of water and 0.53 g (6.12 mmol of tertiary amino groups) N, N, N ', N'-tetramethyl-1, 6-hexanediamine, 0.81 g (0.76 mmol primary amino groups) of a under the trade name Jeffamine ® ED 2003 available alkylene oxide derivative of structure
  • Cocoamidopropyl betaines (35%) 11.43 11.43 11.43 11.43 11.43
  • Example E was used here as a reference formulation and the relative volume of the examined example with the force (reference) measured for this reference was determined as follows:
  • Relative volume force (example) / force (reference)
  • the hair bundles treated and treated with formulations A, C and D were also presented to a panel consisting of 10 people for evaluating the feeling, the volume and the shine. In terms of feeling, preferred 7 test persons formulation D and 3 formulation C. In terms of volume, preferred 8 test persons formulation C, 1 test person formulation D and 1 test person formulation A. When evaluating the gloss of the hair bundles presented, 6 test persons formulation C and 4 test persons formulation D.
  • Example 2 (diluted with water to 20% silicone) - - 2 -
  • the developer solution listed in Table 11 consists of the following ingredients (according to INCI): Aqua, Hydrogen Peroxide, Acrylates Copolymer, Editronic Acid, Sodium Laureth Sulfate, 2,6-Dicarboxypyridine, Disodium Pyrophosphate, Dimethicone. 2 g each of the developer solutions described in Table 11 were mixed with 2 g of Brilliance Intensive Color Cream - Intensvrot 872 - color cream by stirring. Then 6 strands of natural blonde hair were dyed with a formulation as described in Example 7. These locks of hair were then washed 20 times with the shampoo formulation K described in Example 7 in Table 7. Then, as described in Example 7, the color result of all and the relative softness of the strands of hair treated with formulations S, V, W and X were determined. The results are described in Table 12.

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Abstract

L'invention concerne l'utilisation de copolymères de polyamido- et/ou polyammonium-polysiloxane linéaires ou ramifiées comportant les unités répétitives de formule (I) : -[Q-V]- dans la coloration des cheveux et/ou le traitement des cheveux colorés ainsi que des compositions pour la coloration des cheveux et/ou le traitement des cheveux colorés.
PCT/EP2004/050091 2003-02-07 2004-02-06 Utilisation de copolymeres de polyamino- et/ou polyammonium-polysiloxane WO2004069137A2 (fr)

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DE2003104923 DE10304923A1 (de) 2003-02-07 2003-02-07 Herstellung und Verwendung Polyamino- und/oder Polyammonium-Polysiloxancopolymere enthaltender Formulierungen
DE10304923.1 2003-02-07
DE10333375.4 2003-07-23
DE10333375 2003-07-23

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DE102005014311A1 (de) * 2005-03-30 2006-10-12 Ge Bayer Silicones Gmbh & Co. Kg Polyamino- und/oder Polyammonium-Polysiloxan-Colpolymer-Verbindungen mit kammartig angeordneten Polyalkylenonideinheiten
WO2007000223A1 (fr) * 2005-06-25 2007-01-04 Henkel Kommanditgesellschaft Auf Aktien Produits cosmetiques contenant un compose de polyammonium-polysiloxane et d'autres principes actifs
EP1806127A1 (fr) * 2005-12-23 2007-07-11 Henkel KGaA Décolorant, contenant une liaison polyammonium-polysiloxane
EP1806128A1 (fr) 2005-12-23 2007-07-11 Henkel KGaA Produit de soin pour cheveux
FR2931660A1 (fr) * 2008-05-30 2009-12-04 Oreal Composition cosmetique comprenant un copolymere polydiammonium-polysiloxane et un amidon et procede de traitement cosmetique des matieres keratiniques.
DE102008052859A1 (de) 2008-10-23 2010-04-29 Beiersdorf Ag Synergistische Mischungen von kationischen Aminosilikon Terpolymer mit einem weiteren Silikon
DE102010013763A1 (de) 2010-03-31 2011-10-06 Beiersdorf Ag Ausspülhaarbehandlungsmittel mit niedrig- bis mittelviskosen Polydimethylsiloxanen
US9198849B2 (en) 2013-07-03 2015-12-01 The Procter & Gamble Company Shampoo composition comprising low viscosity emulsified silicone polymers
US9650593B2 (en) 2010-04-01 2017-05-16 The Procter & Gamble Company Organosilicones
WO2018226656A1 (fr) 2017-06-05 2018-12-13 Momentive Performance Materials Inc. Compositions aqueuses pour le traitement des cheveux
WO2018226548A1 (fr) 2017-06-05 2018-12-13 Momentive Performance Materials Inc. Traitement capillaire comprenant des polyorganosiloxanes à fractions polyhydroxyaromatiques
EP3501488A1 (fr) 2017-12-21 2019-06-26 Momentive Performance Materials GmbH Compositions aqueuses de polymère de silicone
US10363211B2 (en) 2013-09-27 2019-07-30 The Procter And Gamble Company Hair conditioning compositions comprising low viscosity emulsified silicone polymers
US10617617B1 (en) 2018-12-04 2020-04-14 Momentive Performance Materials Inc. Polycarboxylic acid compounds for the treatment of fibrious amino acid based substrates, especially hair
WO2020104687A1 (fr) 2018-11-24 2020-05-28 Momentive Performance Materials Gmbh Utilisation de composés polyhydroxyaromatiques pour le traitement de substrats fibreux à base d'acides aminés
WO2020117516A1 (fr) 2018-12-04 2020-06-11 Momentive Performance Materials Inc. Utilisation de composés poly(acide carboxylique) pour le traitement de substrats fibreux à base d'acides aminés, spécialement des cheveux
WO2020222668A1 (fr) 2019-04-30 2020-11-05 Instituto de Medicina Molecular João Lobo Antunes Inhibiteurs de la voie rank en combinaison avec des inhibiteurs de cdk
WO2021123904A1 (fr) 2019-12-17 2021-06-24 Momentive Performance Materials Gmbh Composés d'acide gras polymeres pour le traitement de substrats fibreux à base d'acides aminés, en particulier les cheveux
WO2021123911A2 (fr) 2019-12-17 2021-06-24 Momentive Performance Materials Gmbh Composés d'acides gras polymériques non ioniques pour le traitement de substrats fibreux à base d'acides aminés, en particulier des cheveux
WO2022263525A1 (fr) 2021-06-16 2022-12-22 Momentive Performance Materials Gmbh Composés de sel d'acide gras polymères pour le traitement de substrats fibreux à base d'acides aminés, en particulier les cheveux

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Cited By (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8076442B2 (en) 2005-03-30 2011-12-13 Momentive Performance Materials Gmbh Polyamino and/or polyammonium/polysiloxane copolymer compounds with polyalkylene oxide units in comb-shaped arrangement
DE102005014311A1 (de) * 2005-03-30 2006-10-12 Ge Bayer Silicones Gmbh & Co. Kg Polyamino- und/oder Polyammonium-Polysiloxan-Colpolymer-Verbindungen mit kammartig angeordneten Polyalkylenonideinheiten
WO2007000223A1 (fr) * 2005-06-25 2007-01-04 Henkel Kommanditgesellschaft Auf Aktien Produits cosmetiques contenant un compose de polyammonium-polysiloxane et d'autres principes actifs
EP1806127A1 (fr) * 2005-12-23 2007-07-11 Henkel KGaA Décolorant, contenant une liaison polyammonium-polysiloxane
EP1806128A1 (fr) 2005-12-23 2007-07-11 Henkel KGaA Produit de soin pour cheveux
FR2931660A1 (fr) * 2008-05-30 2009-12-04 Oreal Composition cosmetique comprenant un copolymere polydiammonium-polysiloxane et un amidon et procede de traitement cosmetique des matieres keratiniques.
WO2009156663A2 (fr) * 2008-05-30 2009-12-30 L'oreal Composition cosmetique comprenant un copolymere polydiammonium-polysiloxane et un amidon et procede de traitement cosmetique des matieres keratiniques
WO2009156663A3 (fr) * 2008-05-30 2010-02-18 L'oreal Composition cosmetique comprenant un copolymere polydiammonium-polysiloxane et un amidon et procede de traitement cosmetique des matieres keratiniques
WO2010046119A2 (fr) 2008-10-23 2010-04-29 Beiersdorf Ag Mélanges synergiques comprenant un terpolymère d'aminosilicone cationique et une autre silicone
WO2010046119A3 (fr) * 2008-10-23 2010-07-15 Beiersdorf Ag Mélanges synergiques comprenant un terpolymère d'aminosilicone cationique et une autre silicone
DE102008052859A1 (de) 2008-10-23 2010-04-29 Beiersdorf Ag Synergistische Mischungen von kationischen Aminosilikon Terpolymer mit einem weiteren Silikon
DE102010013763A1 (de) 2010-03-31 2011-10-06 Beiersdorf Ag Ausspülhaarbehandlungsmittel mit niedrig- bis mittelviskosen Polydimethylsiloxanen
EP2552996B1 (fr) * 2010-04-01 2019-05-22 The Procter and Gamble Company Organosilicones
US9650593B2 (en) 2010-04-01 2017-05-16 The Procter & Gamble Company Organosilicones
US9198849B2 (en) 2013-07-03 2015-12-01 The Procter & Gamble Company Shampoo composition comprising low viscosity emulsified silicone polymers
US10363211B2 (en) 2013-09-27 2019-07-30 The Procter And Gamble Company Hair conditioning compositions comprising low viscosity emulsified silicone polymers
WO2018226656A1 (fr) 2017-06-05 2018-12-13 Momentive Performance Materials Inc. Compositions aqueuses pour le traitement des cheveux
WO2018226548A1 (fr) 2017-06-05 2018-12-13 Momentive Performance Materials Inc. Traitement capillaire comprenant des polyorganosiloxanes à fractions polyhydroxyaromatiques
US10982051B2 (en) 2017-06-05 2021-04-20 Momentive Performance Materials Inc. Aqueous compositions for hair treatment comprising polyorganosiloxanes with polyhydroxyaromatic moieties
US11179312B2 (en) 2017-06-05 2021-11-23 Momentive Performance Materials Inc. Aqueous compositions for the treatment of hair
EP3501488A1 (fr) 2017-12-21 2019-06-26 Momentive Performance Materials GmbH Compositions aqueuses de polymère de silicone
WO2020104687A1 (fr) 2018-11-24 2020-05-28 Momentive Performance Materials Gmbh Utilisation de composés polyhydroxyaromatiques pour le traitement de substrats fibreux à base d'acides aminés
US11090255B2 (en) 2018-12-04 2021-08-17 Momentive Performance Materials Inc. Use of polycarboxylic acid compounds for the treatment of fibrious amino acid based substrates, especially hair
US10617617B1 (en) 2018-12-04 2020-04-14 Momentive Performance Materials Inc. Polycarboxylic acid compounds for the treatment of fibrious amino acid based substrates, especially hair
WO2020117509A1 (fr) 2018-12-04 2020-06-11 Momentive Performance Materials Inc. Composés de poly(acide carboxylique) pour le traitement de substrats fibreux à base d'acides aminés, en particulier les cheveux
WO2020117516A1 (fr) 2018-12-04 2020-06-11 Momentive Performance Materials Inc. Utilisation de composés poly(acide carboxylique) pour le traitement de substrats fibreux à base d'acides aminés, spécialement des cheveux
WO2020222668A1 (fr) 2019-04-30 2020-11-05 Instituto de Medicina Molecular João Lobo Antunes Inhibiteurs de la voie rank en combinaison avec des inhibiteurs de cdk
WO2021123911A2 (fr) 2019-12-17 2021-06-24 Momentive Performance Materials Gmbh Composés d'acides gras polymériques non ioniques pour le traitement de substrats fibreux à base d'acides aminés, en particulier des cheveux
WO2021123904A1 (fr) 2019-12-17 2021-06-24 Momentive Performance Materials Gmbh Composés d'acide gras polymeres pour le traitement de substrats fibreux à base d'acides aminés, en particulier les cheveux
WO2022263525A1 (fr) 2021-06-16 2022-12-22 Momentive Performance Materials Gmbh Composés de sel d'acide gras polymères pour le traitement de substrats fibreux à base d'acides aminés, en particulier les cheveux

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