WO2009156241A1 - Haarbehandlungsmittel und haarnachbehandlungsmittel zum schutz vor schäden durch chemische behandlung und zur reparatur bereits geschädigter haare enthaltend als wirksubstanzen etherguanidine - Google Patents
Haarbehandlungsmittel und haarnachbehandlungsmittel zum schutz vor schäden durch chemische behandlung und zur reparatur bereits geschädigter haare enthaltend als wirksubstanzen etherguanidine Download PDFInfo
- Publication number
- WO2009156241A1 WO2009156241A1 PCT/EP2009/056492 EP2009056492W WO2009156241A1 WO 2009156241 A1 WO2009156241 A1 WO 2009156241A1 EP 2009056492 W EP2009056492 W EP 2009056492W WO 2009156241 A1 WO2009156241 A1 WO 2009156241A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acid
- hair
- radicals
- ether
- carbon atoms
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/006—Antidandruff preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/43—Guanidines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/12—Preparations containing hair conditioners
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
- C07C279/08—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by singly-bound oxygen atoms
Definitions
- human hair is today treated in a variety of ways with hair cosmetic preparations. These include, for example, the cleansing of hair with shampoos, the care and regeneration with rinses and cures, and the bleaching (or synonymously brightening or bleaching), dyeing and shaping the hair with bleaching agents (or synonym brighteners or bleaching agents), colorants, tinting agents, Wells and styling preparations.
- the color change of the hair experiences an increasing popularity with the consumer.
- the treatment with chemical agents alters the structure and surface properties of the hair. For example, in a perm, both the cortex and the cuticle of the hair are attacked. The disulfide bridges of cystine are broken by the reduction step and partially oxidized to cysteic acid in the subsequent oxidation step.
- Bleaching not only destroys the melanin, but also oxidizes about 15 to 25 weight percent of the disulfide bonds of the cystine with a mild bleach. With an excessive bleaching, it may even be up to 45% by weight (K.F. de Polo, A Short Textbook of Cosmetology, 2000, Verlag für chemische Industrie, H. Ziolkowsky GmbH).
- EP 1 493 423 describes the use of alkylguanidine compounds and / or salts thereof in hair treatment compositions and hair aftertreatment agents for the prevention of damage by chemical treatment agents and for the repair of damaged hair.
- EP 1 646 429 describes the use of alkyl guanidine compounds for the treatment and aftertreatment of hair.
- EP 1 671 615 describes emulsions comprising cationic emulsifiers based on salt conjugates of guanidine compounds, these guanidine compounds also including alkyloxyalkyl-guanidine compounds (Etherguanidine) can be. These emulsions can also be used for the production of hair care products.
- JP 11-035546 the use of branched is (C12-24- alkyloxy-Ci- 6 alkyl) guanidine derivatives described in hair care products.
- the object of the present invention was to provide ether guanidines which have improved hair care properties and can easily be incorporated into various formulations.
- the present invention therefore provides etherguanidines of the general formula (I)
- hair treatment compositions and hair aftertreatment compositions which have as active substances the etherguanidines of the invention according to the claims.
- the present invention provides the use of the inventive ether guanidines or the hair treatment compositions and hair aftertreatment agents according to the invention for the preparation of hair rinses, hair shampoos, hair conditioners, leave-in conditioners, softeners and setting formulations.
- etherguanidines should be understood to mean not only the etherguanidines themselves but also their salts or hydrates.
- the etherguanidines according to the invention have the advantage that they have both a good stability and a good formability. They also cause a clear effect even at low concentrations, are non-toxic, are very well tolerated by the hair and scalp, have a high compatibility with other ingredients and can be easily incorporated into hair treatment and hair treatment. In addition, they may still have an antimicrobial effect.
- etherguanidines and compositions according to the invention are described below by way of example, without the invention being restricted to these exemplary embodiments.
- ranges, general formulas, or classes of compounds are intended to encompass not only the corresponding regions or groups of compounds explicitly mentioned, but also all sub-regions and sub-groups of compounds obtained by removing individual values (ranges) or compounds can be. If documents are cited in the context of the present description, their contents are intended to form part of the disclosure content of the present invention. Be in the context of the present invention, compounds such.
- organomodifi ed polysiloxanes described which may have several units multiple, they may statistically distributed (statistical oligomer or polymer) or ordered (block oligomer or block polymer) occur in these compounds. Information on the number of units in such compounds is to be understood as an average, averaged over all corresponding compounds.
- R 1 -CH 2 -CH 2 -CH 2 -OR 3 with R 3 independently of one another hydrocarbon radicals, preferably alkyl radicals, with greater than or equal to 10 carbon atoms, preferably with 11 to 18, preferably 12 to 15 carbon atoms, wherein a
- R 2 independently of one another H or an optionally branched hydrocarbon radical optionally containing double bonds having 1 to 30 C atoms, preferably 4 to 22 and preferably 8 to 12 C atoms.
- Preferred novel ether guanidines are those in which the radicals R 2 are exclusively hydrogen atoms.
- ether guanidines from 50 to 95 wt .-%, preferably 70 to 90 wt .-%, preferably 75 to 85 wt .-% and particularly preferably about 80 wt .-% of the etherguanidines R 3 which are unbranched alkyl radicals, and 5 to 50 wt .-%, preferably 10 to 30 wt .-%, preferably 15 to 25 wt .-% and most preferably about 20% by weight of the ether guanidines have R 3 radicals which are branched alkyl radicals, the unbranched and branched alkyl radicals preferably having from 12 to 15 carbon atoms.
- the ether guanidines or the mixtures thereof are those in which both alkyl radicals R 3 with 12 and with 13, 14 and 15 carbon atoms are present and these in each case in an amount of 10 to 50 wt .-%, preferably 15 to 40 wt .-% and particularly preferably in a ratio of 20 to 30 wt .-% based on the mass of all alkyl radicals R 3 are included.
- the inventive Etherguanidine z. B be the salt of an organic or inorganic acid.
- the inventive Etherguanidine z. B the salt of at least one of the acids selected from the group of substituted or unsubstituted, preferably unsubstituted carboxylic acids (mono-, di- and polycarboxylic acids), such as. Formic acid, acetic acid, propionic acid, butanoic acid, isobutyric acid, hexanoic acid,
- Glycine alanine, beta-alanine, valine, leucine, phenylalanine, tyrosine, serine, threonine, methionine, cysteine, cystine, proline, hydroxyproline, pipecolic acid, tryptophan, aspartic acid, asparagine, glutamic acid, glutamine, lysine, histidine, ornithine, Arginine, or aminobenzoic acid, alkylsulfonic acids, such as. For example, methanesulfonic acid or trifluoromethanesulfonic, arylsulfonic, such as. B. benzenesulfonic acid or p-toluenesulfonic acid or inorganic acids such. B., carbonic acid, phosphoric acid, hydrochloric acid, hydrobromic acid,
- Hydroiodic acid hydrofluoric acid, perchloric acid, nitric acid or sulfuric acid, and mixtures thereof, preferably the salt of lactic acid, tartaric acid, acetic acid, sulfuric acid or hydrochloric acid, and preferably the salt of hydrochloric acid.
- the preparation of the Etherguanidine can be done in a conventional manner.
- the preparation of the ether guanidines based on the preparation of alkylguanidines can be carried out by guanidylation of the corresponding amines.
- the production of alkylguanidines is e.g. in the
- alkylamines are guanidylated in an alcoholic solution with cyanamide in the presence of a protonic acid.
- the products are called obtained crystalline salts.
- the preparation of the etherguanidines according to the invention can be carried out in an analogous manner by reacting etheramines in an alcoholic solution with cyanamide in the presence of a protonic acid.
- the preparation of the etherguanidines according to the invention can also be carried out by reacting the etheramines with guanidylating agents other than cyanamide.
- guanidylating agents other than cyanamide.
- a list of other guanidylating agents and methods can be found i.a. in EP 1 462 463, Ullmann's Encyclopedia of Industrial Chemistry "Guanidines and Derivatives" chapter 2.4 or Houben-Weyl, E 4, 608-624.
- the etheramines used according to the invention can be obtained in a simple manner by reacting corresponding alcohols R 3 -OH, where R 3 has the abovementioned meaning, with acrylonitrile according to the following reaction scheme:
- Etheramines are commercially available products and are used i.a. offered by the company Tomah Products (USA) under the trade name Tomamine® and the company Evonik Degussa GmbH under the trade name Adogen®.
- the etherguanidines according to the invention can, for. B. be used in hair treatment agents and hair aftertreatment.
- Hair aftertreatment agents in the context of the present invention are in particular those (cosmetic) Preparations understood that are used for post-treatment, shaping and care of the hair after a chemical treatment of the hair (hair post-treatment).
- hair treatment compositions are understood in particular to be (chemical) hair treatment compositions which damage the hair structure and in which the damage can be minimized by the addition of ether guanidines.
- the hair aftertreatment agents of the invention may be e.g. hair conditioners, hair conditioners, softeners, leave-in conditioners, hair shampoos, two-in-one shampoos, setting formulations such as mousse, hair sprays or hair lotions, hair lotions or hair tip fluids. You can z. As a gel, emulsion, solution, aerosol spray or - foaming, Nonaerosolspray or foam present.
- the hair treatment compositions according to the invention and hair aftertreatment agents are characterized in that they have one or more of the etherguanidines according to the invention as the active substance.
- the hair treatment compositions of the invention and hair aftertreatment agents are characterized in that they have one or more of the etherguanidines according to the invention as the active substance.
- the hair treatment compositions of the invention and hair aftertreatment agents are characterized in that they have one or more of the etherguanidines according to the invention as the active substance.
- Hair aftertreatment agent 0.01 to 10.0 wt .-%, preferably 0.05 to 8.0 wt .-%, preferably 0.1 to 5.0 wt .-% and particularly preferably 0.1 to 2.5 wt. -% of at least one of the Etherguanidine invention.
- the stated proportions by weight preferably represent the proportions of all the compounds according to the invention
- Hair treatment agent is applied to the keratinic fiber, in particular human hair, there are no restrictions in principle.
- these preparations for example, creams, lotions,
- Microemulsions and multiple emulsions, gels, sprays, aerosols and foam aerosols are disclosed.
- the pH of the hair treatment agent according to the invention may preferably be from 2 to 11, preferably from 3 to 10.
- the hair treatment compositions and hair aftertreatment agents according to the invention particularly preferably have a pH of from 3 to 7.
- any acid or base which can be used for cosmetic purposes or any buffer mixture can be used.
- Preferred bases are ammonia, alkali hydroxides, monoethanolamine, triethanolamine and
- N, N, N ', N'-tetrakis (2-hydroxypropyl) ethylenediamine Preferred acids are, for. As lactic acid or citric acid.
- hair remaining hair treatment compositions according to the invention and hair aftertreatment agents have been found to be effective and may therefore represent preferred embodiments of the teaching of the invention.
- Under remaining on the hair according to the invention means understood that not in the context of treatment after a period of a few seconds to one hour with
- these preparations are formulated as a hair conditioner or hair conditioner.
- the hair treatment compositions and
- Hair aftertreatment agents according to this embodiment can be rinsed out after expiration of this exposure time with water or an at least predominantly aqueous agent; however, they may be left on the hair as stated above.
- the agents according to the invention may also be, for example, cleansing agents such as shampoos, nourishing agents such as rinses, firming agents such as hair fixatives, mousses, styling gels and hair drier, permanent shaping agents such as perming and fixing agents and in particular in the context of a perming process or dyeing process used pre-treatment or rinsing act.
- cleansing agents such as shampoos
- nourishing agents such as rinses
- firming agents such as hair fixatives, mousses, styling gels and hair drier
- permanent shaping agents such as perming and fixing agents and in particular in the context of a perming process or dyeing process used pre-treatment or rinsing act.
- the preparations of this invention may in principle contain all other components known to the person skilled in the art for such cosmetic compositions.
- auxiliaries and additives are, for example, nonionic polymers such as, for example, vinylpyrrolidone / vinyl acrylate copolymers, polyvinylpyrrolidone and vinylpyrrolidone / vinyl acetate copolymers and polysiloxanes, thickeners such as agar-agar, guar gum, alginates, xanthan gum. Gum, gum arabic, karaya gum, locust bean gum, linseed gums, dextrans, cellulose derivatives, e.g. Methylcellulose, hydroxyalkylcellulose and
- hair conditioning compounds such as phospholipids, such as soybean lecithin, egg lecithin and cephalins, and silicone oils, perfume oils, dimethyl isosorbide and cyclodextrins, solvents and mediators such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerol and diethylene glycol, symmetrical and unbalanced, unbranched and branched dialkyl ethers having a total of from 12 to 36 carbon atoms, in particular 12 to 24 carbon atoms, such as, for example, di-n-octyl ether, di-n-decyl ether, di-n-nonyl ether, di-n-undecyl ether and di-n- dodecyl
- sunflower oil orange oil, almond oil, wheat germ oil and peach kernel oil and phospholipids, such as soybean lecithin, egg lecithin and cephalin, quaternized amines such as methyl-l-alkylamidoethyl-2 alkylimidazolinium methosulfate, defoamers such as silicones, dyes for staining the agent, anti-dandruff agents such as piroctone olamine, zinc omadine and climbazole, active ingredients such as allantoin and bisabolol, cholesterol, bodying agents such as sugar esters, polyol esters or polyol alkyl ethers, fats and waxes such as spermaceti, beeswax, montan wax and paraffins, fatty acid alkanolamides, complexing agents such as EDTA, NTA, alaninediacetic acid and phosphonic acids, swelling and penetrating agents such as primary, secondary and tertiary phosphat
- thioglycolic acid and its derivatives thiolactic acid, cysteamine, thiomalic acid and -Mercaptoethansulfonklare, propellants such as propane-butane mixtures, N2O, dimethyl ether, CO2 and air, antioxidants.
- propellants such as propane-butane mixtures, N2O, dimethyl ether, CO2 and air, antioxidants.
- the hair treatment compositions according to the invention and hair aftertreatment compositions which comprise the etherguanidines according to the invention can also be formulated from 0 to 10% by weight.
- % preferably from 0.1 to 7.5% by weight of one or more emulsifiers, from 0 to 10% by weight, preferably from 0.1 to 7.5% by weight, of one or more consistency factors, from 0 to 10 wt .-%, preferably from 0.1 to 7.5 wt .-% of one or more, preferably cationic, surfactants and / or
- the rest can z. B. water (ad 100 wt .-% water).
- the hair treatment compositions and hair aftertreatment agents according to the invention may contain one or more hair cosmetic active ingredients, preferably selected from the group of protein hydrolyzates of plant or animal origin based on keratin, collagen, elastin, peas, wheat, rice, soy, milk, silk or corn, anti-dandruff active ingredients , such as As Piroctone olamine, zinc Omadine, Pyrithionderivate (eg., Zinc pyrithione, aluminum pyrithione), sulfur colloidal, salicylic acid derivatives, selenium disulfide, selenium oxide, bifonazole, Actirox and climbazole, sebostatics, vitamins and / or vitamin precursors and / or derivatives of Vitamins or vitamin precursors, panthenol, pyrrolidonecarboxylic acid, bisabolol, plant extracts, niacinamide, polymeric quats, silicone compounds, creatine and / or ceramides.
- hair cosmetic active ingredients
- Preferred vitamins according to the invention, pro-vitamins and vitamin precursors are those which are usually assigned to groups A, B, C, E, F and H.
- vitamin A The group of substances called vitamin A include, for. Retinol (vitamin Al) and 3, 4-didehydroretinol
- the ß-carotene is the provitamin of retinol.
- vitamin A component according to the invention for example, vitamin A acid and its esters, vitamin A aldehyde and vitamin A alcohol and its esters such as
- the preparations used according to the invention contain the vitamin A component preferably in amounts of 0.05-1 wt .-%, based on the total preparation.
- the vitamin B group or the vitamin B complex include u. a. Vitamin B1 (thiamine), vitamin B2 (riboflavin) and vitamin B3. Under this name, the compounds nicotinic acid and nicotinamide (niacinamide) are often performed.
- Preferred according to the invention is the nicotinic acid amide which is contained in the agents used according to the invention preferably in amounts of from 0.05 to 1% by weight, based on the total agent.
- the vitamin B group or the vitamin B complex also includes vitamin B5 (pantothenic acid, panthenol and pantolactone). Panthenol and / or pantolactone are preferably used in the context of this group.
- panthenol which can be used according to the invention are, in particular, the esters and ethers of panthenol and also cationically derivatized panthenols.
- Individual representatives are, for example, the panthenol triacetate, the panthenol monoethyl ether and its monoacetate and also the cationic panthenol derivatives disclosed in WO 92/13829.
- the said compounds of the vitamin B5 type are contained in the agents used according to the invention preferably in amounts of 0.05-10% by weight, based on the total agent. Amounts of 0.1-5 wt .-% are particularly preferred. Also part of the vitamin B group or the vitamin B complex
- Vitamin B6 pyridoxine and pyridoxamine and pyridoxal.
- Vitamin C ascorbic acid
- Vitamin C is used in the compositions according to the invention preferably in amounts of 0.1 to 3 wt .-%, based on the total agent.
- Vitamin E tocopherols, especially ⁇ -tocopherol.
- Tocopherol and its derivatives which include in particular the esters such as the acetate, the nicotinate, the phosphate and the succinate, are preferably present in the agents used according to the invention in amounts of 0.05-1% by weight, based on the total agent ,
- Vitamin F is usually understood as meaning essential fatty acids, in particular linoleic acid, linolenic acid and arachidonic acid.
- Biotin is contained in the agents used according to the invention preferably in amounts of from 0.0001 to 1.0% by weight, in particular in amounts of from 0.001 to 0.01% by weight.
- the agents used according to the invention preferably contain vitamins, provitamins and vitamin precursors from groups A, B, E and H. Panthenol, pantolactone, pyridoxine and its derivatives as well as nicotinic acid amide and biotin are particularly preferred.
- Plant extracts suitable according to the invention are preferably prepared by extraction of the entire plant. However, it may also be preferred in individual cases, the extracts exclusively from flowers and / or
- According to the invention are especially the extracts of green tea, oak bark, nettle, witch hazel, hops, henna, chamomile, burdock root, horsetail, hawthorn, linden, almond, aloe vera, spruce needle, horse chestnut, sandalwood, juniper, coconut, mango, apricot, lime , Wheat, kiwi, melon, orange, grapefruit, sage, rosemary, birch, mallow, meadowfoam, quenelle, yarrow, thyme, lemon balm, toadstool, coltsfoot, marshmallow, meristem, ginseng and ginger root.
- the extracts are particularly suitable for use in hair treatment compositions or hair aftertreatment agents according to the invention
- Alcohols are lower alcohols such as ethanol and isopropanol, but especially polyhydric alcohols such as ethylene glycol and Propylene glycol, both as the sole extractant as well as in admixture with water, is preferred. Plant extracts based on water / propylene glycol in a ratio of 1:10 to 10: 1 have proven to be particularly suitable.
- the plant extracts can be used according to the invention both in pure and in diluted form. If they are used in diluted form, they usually contain about 2 to 80 wt .-% of active substance and as a solvent, preferably the extraction agent or extractant mixture used in their extraction.
- compositions according to the invention mixtures of several, especially two, different plant extracts.
- suitable protein hydrolysates are z.
- B product mixtures obtained by acid, alkaline or enzymatically catalyzed degradation of proteins (proteins).
- protein hydrolyzates also means total hydrolyzates as well as individual amino acids and their derivatives as well as mixtures of different amino acids.
- polymers made up of amino acids and amino acid derivatives are understood by the term protein hydrolyzates. The latter include, for example, polyalanine, polyasparagine, polyserine, polyglutamic acid, etc.
- Further examples of compounds which can be used according to the invention are L-alanyl-L-proline, polyglycine, glycyl-L-glutamine or D / L-methionine-S-methylsulfonium chloride.
- ⁇ -amino acids and their derivatives such as ⁇ -alanine, anthranilic acid or hippuric acid can also be used.
- the molecular weight of The protein hydrolysates which can be used according to the invention are preferably from 75, the molecular weight for glycine, to 200,000, preferably the molecular weight is from 75 to 50,000 and very particularly preferably from 75 to 20,000 daltons.
- protein hydrolysates of both vegetable and animal or marine or synthetic origin can be used.
- Animal protein hydrolysates are, for example, elastin,
- Collagen, keratin and milk protein protein hydrolysates which may also be in the form of salts.
- Such products are, for example, under the trademarks Dehylan ®
- Preferred according to the invention is the use of protein hydrolysates of plant origin, eg. Soybean, almond, pea, potato and wheat protein hydrolysates.
- Such products are, for example, under the trademarks Gluadin ® (Cognis), diamine ® (Diamalt) ® (Inolex), Hydrosoy ® (Croda), hydro Lupine ® (Croda), hydro Sesame ® (Croda), Hydro tritium (Croda) and Crotein ® (Croda) available.
- Protein hydrolysates for example in the form of their fatty acid condensation products.
- Such products are for example under the names Lamepon ® (Cognis), Lexein ® (Inolex), Crolastin ® (Croda) or Crotein ® (Croda) expelled.
- the protein hydrolysates are preferably present in the compositions according to the invention in concentrations of from 0.01% by weight to 20% by weight, preferably from 0.05% by weight to 15% by weight and very particularly preferably in amounts of 0.05% by weight. % up to 5% by weight.
- Silicone oils which are suitable according to the invention bring about a wide variety of effects. For example, at the same time they can influence the dry and wet combability, the grip of dry and wet hair and the shine.
- the term silicone oils is understood by the person skilled in the art to mean several structures of organosilicon compounds. First of all, this is understood to mean the dimethiconols (S1). Dimethiconols form the first group of silicones which are particularly preferred according to the invention.
- the dimethiconols according to the invention can be unbranched or branched as well as cyclic or cyclic and branched.
- Unbranched dimethiconols can be represented by the following structural formula (I-I): (SiOHR 1 2 ) -O- (SiR 2 2 -O-) x - (SiOHR ⁇ ) (I-I)
- Branched dimethiconols can be represented by the structural formula (S1-2): CSiOHR 1 J j - O - fSm 3 j - O - ⁇ * - Si • 0 - iSiR ⁇ - O - X - - (SiOHR' ⁇ l
- the radicals R 1 and R 2 are each independently hydrogen, a methyl radical, a C 2 to C 30 unbranched, saturated or unsaturated hydrocarbon radical, a phenyl radical and / or an aryl radical.
- the groups represented by R 1 and R 2 include alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, isopentyl, neopentyl, amyl, isoamyl, hexyl, isohexyl and the like; Alkenyl radicals such as vinyl, halovinyl, alkylvinyl, allyl, haloallyl, alkylallyl; Cycloalkyl radicals such as cyclobutyl, cyclopentyl, cyclohexyl and the like; Phenyl radicals, benzyl radicals, halohydrocarbon radicals such as 3-chloropropyl
- R 1 and R 2 are methyl.
- R 1 include methylene, ethylene, propylene, hexamethylene, decamethylene, -CH 2 CH (CH 3 ) CH 2 -, phenylene, naphthylene, -CH 2 CH 2 SCH 2 CH 2 -, -CH 2 CH 2 OCH 2 - , -OCH 2 CH 2 -, OCH 2 CH 2 CH 2 -, -CH 2 CH (CH 3 ) C (O) OCH 2 -, - (CH 2 ) 3 CC (O) 2 CH 2 -, -C 6 H 4 C 6 H 4 -, -C 6 H 4 CH 2 C 6 H 4 -; and - (CH 2 ) 3 C (O) SCH 2 CH 2 -.
- R 1 and R 2 are methyl, phenyl and C 2 to C 22 - alkyl radicals. Of the C 2 to C 22 alkyl radicals, lauryl, stearyl and behenyl radicals are particularly preferred.
- the numbers x, y and z are integers and each run independently from 0 to 50,000.
- the molecular weights of the dimethicones are preferably between 1000 D and 10,000,000 D.
- the viscosities are preferably between 100 and 10,000,000 cPs measured at 25 ° C. with the aid of a glass capillary viscometer according to the Dow Corning Corporate Test Method CTM 0004 of 20 July 1970. Preferred viscosities are between 1000 and 5,000,000 cps, more preferred viscosities are between 10,000 and 3,000,000 cps, and most preferably between 50,000 and 2,000,000 cps.
- the teaching of the invention also includes that the dimethiconols may already be present as an emulsion.
- the corresponding emulsion of the dimethiconols can be prepared both after the preparation of the corresponding dimethiconols from these and the usual methods of emulsification known to the person skilled in the art.
- both cationic, anionic, nonionic or zwitterionic surfactants and emulsifiers can be used as auxiliaries for the preparation of the corresponding emulsions.
- the emulsions of the dimethiconols can also be prepared directly by an emulsion polymerization process. Such methods are also well known to the person skilled in the art. For example, reference may be made to the "Encyclopedia of Polymer Science and Engineering, Volume 15, Second Edition, pages
- the droplet size of the emulsified particles is preferably 0.01 ⁇ m to 10000 ⁇ m, preferably 0.01 to 100 ⁇ m, more preferably 0.01 to 20 ⁇ m, and most preferably 0.01 to 10 microns.
- the Particle size is determined by the method of light scattering.
- branched dimethiconols are used, it is to be understood that the branching is greater than a random branching, which occurs by impurities of the respective monomers randomly.
- branched dimethiconols are therefore to be understood as meaning that the degree of branching is greater than 0.01%.
- a degree of branching is greater than 0.1%, and most preferably greater than 0.5%.
- the degree of branching is determined from the ratio of unbranched monomers, that is, the amount of monofunctional siloxane, to the branching monomers, that is, the amount of tri- and tetrafunctional siloxanes. According to the invention, both low-branched and highly branched dimethiconols may be preferred.
- Botanisil NU-150M Botanigenics
- Dow Coming 1-1254 Fluid Dow Corning 2-9023 Fluid
- Dow Corning 2-9026 Fluid Ultrapure Dimethiconol (Ultra Chemical)
- Unisil SF- R Universal Preserve
- X-21-5619 Shin-Etsu Chemical Co.
- Abil ® OSW 5 Degussa Care Specialties
- Wacker-Belsil CM 3092 Wacker-Belsil CM 5040, Wacker-Belsil DM 3096, Wacker-Belsil DM 3112 VP, Wacker-Belsil DM 8005 VP, Wacker-Belsil DM 60081 VP (all Wacker-Chemie GmbH mentioned above).
- dimethiconols (S1) are present in the hair treatment compositions or hair aftertreatment agents according to the invention, they preferably contain from 0.01 to 10% by weight, preferably from 0.1 to 8% by weight, particularly preferably from 0.25 to 7.5% by weight. % and in particular 0.5 to 5 wt.% Dimethiconol based on the total composition of the composition.
- Dimethicones (S2) form the second group of silicones, which are particularly preferred according to the invention.
- the dimethicones according to the invention may be unbranched or branched as well as cyclic or cyclic and branched. Unbranched dimethicones can by the following
- the radicals R 1 and R 2 are each independently hydrogen, a methyl radical, a C 2 to C 30 unbranched, saturated or unsaturated hydrocarbon radical, a phenyl radical and / or an aryl radical.
- the groups represented by R 1 and R 2 include alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, isopentyl, neopentyl, amyl, isoamyl, hexyl, isohexyl and the like; Alkenyl radicals such as vinyl, halovinyl, alkylvinyl, allyl, haloallyl, alkylallyl; Cycloalkyl radicals such as cyclobutyl, cyclopentyl, cyclohexyl and the like; Phenyl radicals, benzyl radicals, halohydrocarbon radicals such as 3-chloropropyl
- R 1 examples include methylene, ethylene, propylene, hexamethylene, decamethylene, -CH 2 CH (CH 3 ) CH 2 -, phenylene, naphthylene, -CH 2 CH 2 SCH 2 CH 2 -, -CH 2 CH 2 OCH 2 - , -OCH 2 CH 2 -, -OCH 2 CH 2 CH 2 -, -CH 2 CH (CH 3 ) C (O) OCH 2 -, - (CH 2 ) 3 CC (O) 2 CH 2 -, - C 6 H 4 C 6 H 4 -, -C 6 H 4 CH 2 C 6 H 4 -; and - (CH 2 ) 3 C (O) SCH 2 CH 2 -.
- R 1 and R 2 are methyl, phenyl and C 2 - to C 22 - alkyl radicals. Of the C 2 to C 22 alkyl radicals, very particularly are lauryl, Stearyl and behenyl residues preferred.
- the numbers x, y and z are integers and preferably each independently run from 0 to 50,000.
- the molecular weights of the dimethicones are preferably between 1000 D and 10,000,000 D.
- the viscosities are preferably between 100 and 10,000,000 cPs measured at 25 °. C with the aid of a glass capillary viscometer according to the Dow Corning Corporate Test Method CTM 0004 of 20 July 1970. Particularly preferred viscosities are between 1,000 and 5,000,000 cPs, very particularly preferred viscosities are between 10,000 and 3,000,000 cPs. The most preferred range is between 50,000 and 2,000,000 cps.
- the teaching of the invention also includes that the dimethicones may already be present as an emulsion.
- the corresponding emulsion of the dimethicones can be prepared both after the preparation of the corresponding dimethicones from these and the usual methods of emulsification known to the person skilled in the art.
- both cationic, anionic, nonionic or zwitterionic surfactants and emulsifiers can be used as auxiliaries for the preparation of the corresponding emulsions.
- the emulsions of dimethicones can also be prepared directly by an emulsion polymerization process. Such methods are the
- the droplet size is the emulsified Particles according to the invention 0.01 micron to 10,000 microns, preferably 0.01 to 100 microns, most preferably 0.01 to 20 microns and most preferably 0.01 to 10 microns.
- the particle size is determined by the method of light scattering.
- branched dimethicones are used, it is to be understood that the branching is greater than a random branching, which occurs by impurities of the respective monomers randomly.
- branched dimethicones are therefore to be understood as meaning that the degree of branching is greater than 0.01%.
- a degree of branching is greater than 0.1%, and most preferably greater than 0.5%.
- the degree of branching is determined from the ratio of unbranched monomers, that is, the amount of monofunctional siloxane, to the branching monomers, that is, the amount of tri- and tetrafunctional siloxanes. According to the invention, both low-branched and highly branched dimethicones can be very particularly preferred.
- dimethicones (S2) are contained in the hair treatment compositions or hair aftertreatment agents according to the invention, these compositions preferably contain from 0.01 to 10% by weight, preferably from 0.1 to 8% by weight, particularly preferably
- Dimethicone copolyols form another group of preferred silicones. Dimethicone copolyols can be represented by the following structural formulas: (SiRS) -O- (SiR 2 2 O-) x - (SiRPE-O-) y - (SiR ⁇ ) (S3-1) or by the following structural formula: PE- (SiR 1) -O- (SiR 2 2 -O-) x - (SiR 1) -PE (S3-2)
- Branched dimethicone copolyols can be represented by the structural formulas (S3-3) or (S3-4):
- the radicals R 1 and R 2 are each independently hydrogen, a methyl radical, a C 2 to C 30 unbranched, saturated or unsaturated hydrocarbon radical, a phenyl radical and / or an aryl radical.
- the groups represented by R 1 and R 2 include alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, isopentyl, neopentyl, amyl, isoamyl, hexyl, isohexyl and the like; Alkenyl radicals such as vinyl, halovinyl, alkylvinyl, allyl, haloallyl, alkylallyl; Cycloalkyl radicals such as cyclobutyl, cyclopentyl, cyclohexyl and the like; Phenyl radicals, benzyl radicals, halohydrocarbon radicals such as 3-chloropropyl
- R 1 examples include methylene, ethylene, propylene, hexamethylene, decamethylene, -CH 2 CH (CH 3 ) CH 2 -, phenylene, naphthylene, -CH 2 CH 2 SCH 2 CH 2 -, -CH 2 CH 2 OCH 2 - , -OCH 2 CH 2 -, -OCH 2 CH 2 CH 2 -, -CH 2 CH (CH 3 ) C (O) OCH 2 -, - (CH 2 ) 3 CC (O) OCH 2 CH 2 -, C 6 H 4 C 6 H 4 -, -C 6 H 4 CH 2 C 6 H 4 -; and - (CH 2 ) 3 C (O) SCH 2 CH 2 -.
- R 1 and R 2 is methyl, phenyl, and C 2 are - to C 22 - alkyl radicals.
- C 2 - to C 22 -alkyl radicals particular preference is given to lauryl, stearyl and behenyl radicals.
- PE stands for a polyoxyalkylene radical.
- Preferred polyoxyalkylene radicals are derived from ethylene oxide, propylene oxide and glycerol.
- the numbers x, y and z are integers and preferably each independently run from 0 to 50,000.
- the molecular weights of the dimethicone copolyols are between 1000 D and 10,000,000 D.
- the viscosities are between 100 and 10,000,000 cPs measured at 25 ° C.
- Preferred viscosities are between 1,000 and 5,000,000 cPs, and particularly preferred viscosities are between 10,000 and 3,000,000 cPs. The most preferred range is between 50,000 and 2,000,000 cps.
- the teaching of the invention also includes that the Dimethiconcopolymere can already be present as an emulsion.
- the corresponding emulsion of the Dimethiconcopolymere can already be present as an emulsion.
- Dimethiconecopolyole be prepared both after the preparation of the corresponding dimethicone copolyols from these and the conventional methods for emulsification known in the art.
- both cationic, anionic, nonionic or zwitterionic surfactants and emulsifiers can be used as auxiliaries for the preparation of the corresponding emulsions.
- the emulsions of Dimethicone copolyols can also be prepared directly by an emulsion polymerization process. Such methods are also well known to the person skilled in the art. For example, see “Encyclopedia of Polymer Science and Engineering, Volume 15, Second Edition, pages 204 to 308, John Wiley & Sons, Inc. 1989". This reference is expressly incorporated by reference.
- the droplet size of the emulsified particles is preferably from 0.01 ⁇ m to 10000 ⁇ m, preferably from 0.01 to 100 ⁇ m, more preferably from 0.01 to 20 ⁇ m, and most preferably 0.01 up to 10 ⁇ m.
- the particle size is determined by the method of light scattering.
- branched dimethicone copolyols are used, it is to be understood that the branching is greater than a random branching, which occurs by impurities of the respective monomers randomly.
- branched dimethicone copolyols are therefore to be understood as meaning that the degree of branching is greater than 0.01%.
- a degree of branching is greater than 0.1%, and most preferably greater than 0.5%.
- the degree of branching is determined from the ratio of unbranched monomers, that is, the amount of monofunctional siloxane, to the branching monomers, that is, the amount of tri- and tetrafunctional siloxanes.
- both low-branched and highly branched dimethicone copolyols can be very particularly preferred.
- the dimethicone copolyols (S3) are present in the hair treatment compositions or hair aftertreatment agents according to the invention, they contain from 0.01 to 10% by weight, preferably 0.1 to 8% by weight, particularly preferably 0.25 to 7.5% by weight. % and in particular 0.5 to 5 wt.% Dimethiconcopolyol based on the total composition.
- Aminofunctional silicones or also called amodimethicones (S4), are silicones which have at least one (optionally substituted) amino group.
- Such silicones may e.g. by the formula (S4-1)
- R in the above formula is a hydrocarbon or a hydrocarbon group of 1 to about 6 carbon atoms
- Q is a polar group of the general formula -R 1 HZ wherein R 1 is a divalent linking group attached to hydrogen and the group Z is an organic, amino-functional radical containing at least one amino-functional group, carbon and hydrogen atoms, carbon, hydrogen and oxygen atoms or carbon, hydrogen and nitrogen atoms;
- "a” assumes values in the range of about 0 to about 2
- "b” assumes values in the range of about 1 to about 3
- "a” + "b” is less than or equal to 3
- "c” is a number in the range from about 1 to about 3
- x is a number ranging from 1 to about 2,000, preferably from about 3 to about 50, and most preferably from about 3 to about 25
- y is a number ranging from about 20 to about 10,000 , preferably from about 125 to about 10,000, and most preferably from about 150 to is about 1,000 and M is a
- Non-limiting examples of the groups represented by R include alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, amyl, isoamyl, hexyl, isohexyl and the like; Alkenyl radicals such as vinyl, halovinyl, alkylvinyl, allyl, haloallyl, alkylallyl; Cycloalkyl radicals such as cyclobutyl, cyclopentyl, cyclohexyl and the like; Phenyl radicals, benzyl radicals, halohydrocarbon radicals such as 3-chloropropyl, 4-bromobutyl, 3, 3, 3-trifluoropropyl, chlorocyclohexyl, bromophenyl, chlorophenyl and the like, and sulfur-containing radicals such as mercaptoethyl, mercaptopropyl, mercaptohexyl
- R and R 1 examples include methylene, ethylene, propylene, hexamethylene, decamethylene, -CH 2 CH (CH 3 ) CH 2 -, phenylene, naphthylene, -CH 2 CH 2 SCH 2 CH 2 -, -CH 2 CH 2 OCH 2 -, -OCH 2 CH 2 -, -OCH 2 CH 2 CH 2 -, -CH 2 CH (CH 3 ) C (O) OCH 2 -, - (CH 2 ) 3 CC (O) OCH 2 CH 2 - -C 6 H 4 C 6 H 4 -, -C 6 H 4 CH 2 C 6 H 4 -; and - (CH 2 ) 3 C (O) SCH 2 CH 2 -.
- Z is an organic, amino-functional radical containing at least one functional amino group.
- Another possible formula for Z is -NH (CH 2 ) z (CH 2 ) ZZ NH 2 , where both z and zz are independently 1 or more, this structure comprising diamino ring structures, such as piperazinyl.
- Z is most preferably a -NHCH 2 CH 2 NH 2 repeat.
- Z is - N (CH 2 ) z (CH 2 ) ZZ NX 2 or -NX 2 , wherein each X of X 2 is independently selected from the group consisting of hydrogen and alkyl groups of 1 to 12 carbon atoms, and z is 0.
- Q is most preferably a polar, amine functional group of the formula -CH 2 CH 2 CH 2 NHCH 2 CH 2 NH 2 .
- "a" assumes values in the range of about 0 to about 2
- "b” assumes values in the range of about 2 to about 3
- "a" + “b” is less than or equal to 3
- the molar ratio of the R a Q b Si0 ( 4 - a - b ) / 2 units to the R c Si0 ( 4 - c) / 2 units is preferably in the Range from about 1: 2 to 1:65, preferably from about 1: 5 to about 1:65, and more preferably from about 1:15 to about 1: 20.
- the various variable substituents in the above formula may be different for the various silicone components present in the silicone blend.
- compositions according to the invention are characterized in that it comprises an amino-functional silicone of the formula (S4-2), R 'a G 3 - a -Si (OSiG 2) n - (OSiG b R' 2 - b) m -O-SiG 3 - a-R'a (S4-2),
- G is -H, phenyl, -OH, -O-CH 3 , -CH 3 , -CH 2 CH 3 , -CH 2 CH 2 CH 3 , -CH (CH 3 ) 2 , -CH 2 CH 2 CH 2 H 3 , - CH 2 CH (CH 3 ) 2 , -CH (CH 3 ) CH 2 CH 3 , -C (CH 3 ) 3 ;
- a stands for a number of
- b is a number from 0 to 1, in particular 1, m and n are numbers whose sum (m + n) of
- R ' is a monovalent radical selected from N (R ") -CH 2 -CH 2 - N (R") 2
- each R represents identical or different radicals from the group -H, -phenyl, -benzyl, of Ci- 2 alkyl groups o- , preferably -CH 3 , -CH 2 CH 3 , -CH 2 CH 2 CH 3 , -CH (CH 3 ) 2 , -CH 2 CH 2 CH 2 H 3 , -CH 2 CH (CH 3 ) 2 , -CH (CH 3 ) CH 2 CH 3 , -C (CH 3 ) 3 , and A represents an anion, which is preferably selected from chloride, bromide, iodide or methosulfate.
- Particularly preferred agents according to the invention are characterized in that they contain an amino-functional silicone of the formula (S4-3)
- m and n are numbers whose sum (m + n) is from 1 to 2000, preferably between 50 and 150, where n preferably values from 0 to 1999 and in particular from 49 to 149 and m preferably values from 1 to 2000 , in particular from 1 to 10 assumes.
- n preferably values from 0 to 1999 and in particular from 49 to 149 and m preferably values from 1 to 2000 , in particular from 1 to 10 assumes.
- Agents according to the invention which are characterized in that they contain an amino-functional silicone of the formula (S4-4) are also particularly preferred.
- nl and n2 are numbers whose sum (m + nl + n2) is from 1 to 2000, preferably between 50 and 150, wherein the sum (nl + n2) preferably takes values from 0 to 1999 and in particular from 49 to 149 and m preferably values from 1 to 2000, in particular from 1 to 10.
- S4 amodimethicones
- agents according to the invention are preferred in which the amino-functional silicone has an amine number above 0.25 meq / g, preferably above 0.3 meq / g and in particular above 0.4 meq / g ,
- the amine number stands for the milliequivalents of amine per gram of amino-functional silicone. It can be determined by titration and also expressed in mg KOH / g.
- amodimethicones (S4) are contained in the hair treatment compositions or hair aftertreatment agents according to the invention, these compositions contain from 0.01 to 10% by weight, preferably from 0.1 to 8% by weight, particularly preferably from 0.25 to 7.5% by weight. % and in particular 0.5 to 5 wt.% Of amodimethicone based on the total composition.
- the invention also encompasses the recognition that in the hair treatment compositions according to the invention or
- a mixture of at least 2 different silicones can be used.
- Preferred mixtures of different silicones are, for example, dimethicones and dimethiconols, unbranched dimethicones and cyclic dimethiconols. A very particularly preferred
- Mixture of silicones consists of at least one cyclic dimethiconol and / or dimethicone, at least one further non-cyclic dimethicone and / or dimethiconol and at least one amino-functional silicone. If different silicones are used as a mixture, the mixing ratio is largely variable. Preferably, however, all silicones used for mixing are used in a ratio of 5: 1 to 1: 5 in the case of a binary mixture. A ratio of 3: 1 to 1: 3 is particularly preferred. Very particularly preferred mixtures contain all the silicones contained in the mixture largely in a ratio of about 1: 1, in each case based on the amounts used in wt.%.
- these compositions contain from 0.01 to 10% by weight, preferably from 0.1 to 8% by weight, particularly preferably from 0.25 to 7.5% by weight, and in particular 0.5 to 5 wt.% Of silicone mixture based on the total composition.
- the cosmetic preparations according to the invention for the treatment of the hair after a chemical treatment may contain, in addition to the inventive ether guanidines and the above-mentioned optional components, further components which are advantageous and / or usual for the particular application.
- shampoos can contain from 3 to 30% by weight of foaming anionic, zwitterionic, ampholytic and nonionic surfactants.
- Hair rinses and hair treatments can z. B. 0 to 10 wt .-%, preferably 0.5 to 5 wt .-%, emulsifiers, 0 to 10 wt .-%, preferably 0.5 to 5 wt .-%, consistency and 0 to 20 wt. % cosmetic oils, the z. B. vegetable and / or of synthetic origin, emollients, vitamin preparations and / or proteins.
- Shampoos, hair conditioners, hair conditioners and softeners may contain 0 to 8% by weight, preferably 0.1 to 5% by weight, cationic surfactants and polymers having quaternary ammonium groups to reduce static chargeability and to improve combability, feel and gloss.
- Suitable anionic surfactants (E1) in preparations according to the invention are all anionic surfactants suitable for use on the human body. These are characterized by a water-solubilizing, anionic group such as. Example, a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group having about 8 to 30 carbon atoms. In addition, glycol or polyglycol ether groups, ester, ether and amide groups and hydroxyl groups may be present in the molecule.
- anionic surfactants are, in each case in the form of the sodium, potassium and ammonium as well as the mono-, di- and trialkanolammonium salts having 2 to 4 C atoms in the alkanol group, unbranched and branched fatty acids having 8 to 30 C atoms (Soaps), ether carboxylic acids of the formula RO-
- Sulfosuccinic acid mono- and dialkyl esters having 8 to 24 C atoms in the alkyl group and sulfosuccinic acid mono- alkylpolyoxyethyl esters having 8 to 24 C atoms in the alkyl group and 1 to 6 oxyethyl groups, unbranched alkanesulfonates having 8 to 24 C atoms, unbranched alpha-
- OX (El-I) in the R 1 is preferably an aliphatic hydrocarbon radical having 8 to 30 carbon atoms
- R 2 is hydrogen, a radical (CH 2 CH 2 O) n R 2 or X
- n is a number from 1 to 10
- X is is hydrogen, an alkali or alkaline earth metal or NR 3 R 4 R 5 R 6 , with R 3 to R 6 independently of one another represents hydrogen or a C 1 to C 4 hydrocarbon radical, is sulfated
- Typical examples of monoglyceride (ether) sulfates suitable for the purposes of the invention are the reaction products of lauric acid monoglyceride, coconut fatty acid monoglyceride, palmitic acid monoglyceride, stearic acid monoglyceride, oleic acid monoglyceride and tallow fatty acid monoglyceride and their ethylene oxide adducts with sulfur trioxide or chlorosulfonic acid in the form of their sodium salts.
- Preferred anionic surfactants are alkyl sulfates, alkyl polyglycol ether sulfates and ether carboxylic acids having 10 to 18 carbon atoms in the alkyl group and up to 12 glycol ether groups in the molecule, sulfosuccinic mono- and dialkyl esters having 8 to 18 carbon atoms in the alkyl group and Sulfosuccinic acid mono-alkylpolyoxyethyl esters having 8 to 18 carbon atoms in the alkyl group and 1 to 6 oxyethyl groups, monoglyceride sulfates, alkyl and alkenyl ether phosphates and protein fatty acid condensates.
- Zwitterionic surfactants are those surface-active compounds which carry at least one quaternary ammonium group and at least one COO (- 'or -SOs' ' ' group in the molecule.)
- Particularly suitable zwitterionic surfactants are the so-called betaines, such as N-alkyl N, N-dimethylammonium glycinates, for example, the cocoalkyl dimethylammonium glycinate, N-acyl-aminopropyl-N, N-dimethylammoniumglycinate, for example Kokosacylaminopropyldimethylammoniumglycinat, and 2-alkyl-3-carboxymethyl-3-hydroxyethyl-imidazolines each having 8 to 18
- a preferred zwitterionic surfactant is the fatty acid amide derivative known by the INCI name cocamidopropyl betaine.
- Ampholytic surfactants (E3) are understood as meaning those surface-active compounds which, apart from a Cs- 24- alkyl or acyl group in the molecule, contain at least one free amino group and at least one -COOH or -SOsH group and are capable of forming internal salts.
- suitable ampholytic surfactants are N-alkylglycines, N-alkylaminopropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylaminobutyric acids.
- Alkyl sarcosines, 2-Alkylaminopropion Acid and Alkylaminoessigklaren each having about 8 to 24 carbon atoms in the alkyl group.
- Particularly preferred ampholytic surfactants are N-cocoalkyl, cocoacylaminoethylaminopropionate and C12 - CI8 ⁇ sarcosine.
- Nonionic surfactants can be used as the hydrophilic group z.
- Example a polyol group, a Polyalkylenglykoletherement or a combination of polyol and Polyglykoletheroli included.
- Such compounds are, for example, adducts of 2 to 50 moles of ethylene oxide and / or 0 to 5 moles of propylene oxide with unbranched and branched fatty alcohols having 8 to 30 carbon atoms, with fatty acids having 8 to 30 carbon atoms and with alkylphenols having 8 to 15 carbon atoms.
- Atoms in the alkyl group with a methyl or C 2 -C ⁇ alkyl radical end-capped addition products of 2 to 50 moles of ethylene oxide and / or 0 to 5 moles of propylene oxide to unbranched and branched fatty alcohols having 8 to 30 carbon atoms, to fatty acids with 8 bis 30 carbon atoms and to alkylphenols having 8 to 15 carbon atoms in the alkyl group, such as those available under the sales names Dehydol ® LS, Dehydol ® LT (Cognis), C 2 -C 30 fatty acid mono- and diesters of addition products of 1 to 30 moles of ethylene oxide with glycerol, addition products of 5 to 60 moles of ethylene oxide with castor oil and hydrogenated castor oil, polyol fatty acid esters, such as the commercial product Hydagen ® HSP (Cognis) o Sovermol types (Cognis), alkoxylated triglycerides, alkoxy
- R 2 is hydrogen or methyl
- R 3 is unbranched or branched alkyl radicals having 1 to 4 carbon atoms and w is numbers from 1 to 20, Amine oxides, hydroxy mixed ethers, as described, for example, in DE-OS 19738866, sorbitan fatty acid esters and addition products of ethylene oxide onto sorbitan fatty acid esters, for example the polysorbates, sugar fatty acid esters and addition products of ethylene oxide with sugar fatty acid esters,
- the alkyl and alkenyl oligoglycosides can be derived from aldoses or ketoses with 5 or 6 carbon atoms, preferably glucose.
- the preferred alkyl and / or alkenyl oligoglycosides are thus alkyl and / or alkenyl oligoglucosides.
- the index number p in the general formula (E4-II) indicates the degree of oligomerization (DP), d. H.
- DP degree of oligomerization
- alkyl and / or Alkenyloligoglykoside having a mean degree of oligomerization p of 1.1 to 3.0 used. From an application point of view, those alkyl and / or alkenyl oligoglycosides whose degree of oligomerization is less than 1.7 and in particular between 1.2 and 1.4 are preferred.
- the alkyl or alkenyl radical R can be derived from primary alcohols having 4 to 11, preferably 8 to 10 carbon atoms.
- Typical examples are butanol, caproic alcohol, caprylic alcohol, capric alcohol and undecyl alcohol and their technical mixtures, as obtained, for example, in the hydrogenation of technical fatty acid methyl esters or in the hydrogenation of aldehydes from Roelen's oxo synthesis.
- the alkyl or alkenyl radical R 3 can also be derived from primary alcohols having 12 to 22, preferably 12 to 14 carbon atoms.
- Typical examples are lauryl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol, brassidyl alcohol, and technical mixtures thereof which can be obtained as described above.
- alkyl oligoglucosides based on hydrogenated C 12/14 coconut oil having a DP of 1 to 3.
- Nonionic surfactants are, for example, sugar surfactants of the fatty acid-N-alkylpolyhydroxyalkylamide type, a nonionic surfactant of the formula (E4-3), R 5 CO-NR 6 - [Z] (E4-3) in which R 5 is CO for an aliphatic acyl radical having 6 to 22 carbon atoms, R is hydrogen, an alkyl or hydroxyalkyl radical having 1 to 4 carbon atoms and [Z] is an unbranched or branched polyhydroxyalkyl radical having 3 to 12 carbon atoms and 3 to 10 hydroxyl groups ,
- the fatty acid N-alkyl polyhydroxyalkylamides are known substances which can usually be obtained by reductive amination of a reducing sugar with ammonia, an alkylamine or an alkanolamine and subsequent acylation with a fatty acid, a fatty acid alkyl ester or a fatty acid chloride.
- the fatty acid N-alkylpolyhydroxyalkylamides are preferably derived from reducing sugars having 5 or 6 carbon atoms, in particular from glucose.
- the preferred fatty acid N-alkylpolyhydroxyalkylamides are therefore fatty acid N-alkylglucamides as represented by the formula (E4-4):
- the fatty acid N-alkylpolyhydroxyalkylamides used are preferably glucamides of the formula (E4-4) in which R 8 is hydrogen or an alkyl group and R 7 CO is the acyl radical of caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmitic acid, Stearic acid, isostearic acid, oleic acid, elaidic acid, petroselic acid, linoleic acid, linolenic acid, arachidic acid, gadoleic acid, behenic acid or erucic acid or their technical mixtures.
- R 8 is hydrogen or an alkyl group
- R 7 CO is the acyl radical of caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmitic acid, Stearic acid, isostearic acid, oleic acid, elaidic acid, petroselic acid, l
- fatty acid N-alkylglucamides of the formula (E4-4) obtained by reductive amination of glucose with methylamine and subsequent acylation with lauric acid or C 12/14 coconut fatty acid or a corresponding derivative.
- the polyhydroxyalkylamides can also be derived from maltose and palatinose.
- the cationic surfactants may be, for. B. act to quaternary ammonium compounds, such as alkyltrimethylammonium salts, dialkyldimethylammonium, Trialkylmethylammoniumsalze and imidazolinium compounds.
- the long alkyl chains consist of a carbon chain with 10 to 22 carbon atoms, the counterions to the quaternary nitrogen are, for example, halides, sulfate, methosulfate, acetate, lactate, glycolate, nitrate or phosphate.
- Esterquats ie compounds which contain both at least one ester function and at least one quaternary ammonium group as a structural element.
- Preferred ester quats are quaternized ester salts of fatty acids with triethanolamine, quaternized ester salts of fatty acids with diethanolalkylamines and quaternized ester salts of fatty acids with 1,2-dihydroxypropyldialkylamines.
- Such products are marketed for example under the trademark Stepantex ®, Dehyquart ® (Cognis) and Armocare ® (Akzo Nobel).
- the products Armocare ® VGH-70, a N, N-bis are (2- Palmi toyloxyethyl) dimethylammoniumchlor id, as well as Dehyquart ® F-75, Dehyquart ® C-4046, Dehyquart ® L80 and Dehyquart ® AU-35 (Cognis) Examples for such esterquats.
- Alkylamidoquats such as those sold under the name Varisoft® PATC and RTM 50 by Evonik Goldschmidt,
- Alkylamidoamines commonly prepared by amidation of natural or synthetic fatty acids and fatty acid cuts with dialkylaminoamines, and e.g. available under the name Tegoamid® S 18 from Evonik Goldschmidt.
- cationic cellulose derivatives commercially available under the name Celquat® H 100 and L 200 from National Starch or polymer JR® 400 from Amerchol, polymeric dimethyldiallylammonium salts and their copolymers with esters and amides of acrylic acid and methacrylic acid.
- the products commercially available under the name Merquat® 100 or Merquat® 550 from Calgon are examples of such cationic polymers, copolymers of vinylpyrrolidone with quaternized derivatives of dialkylamino acrylate and methacrylate.
- Such compounds are commercially available under the name Gafquat® 735 and Gafquat® 744 from ISP,
- Vinylpyrrolidone-vinylimidazolium methochloride copolymers such as those sold under the name Luviquat® FC 370, FC 550, FC 905 and HM-552 by BASF, quaternized polyvinyl alcohol, quaternized protein hydrolyzates of animal or vegetable origin based on keratin, collagen, elastin, wheat, Rice, soy, milk, silk, corn.
- Such products are, for example, under the name Croquat® Wheat and SiIk from Croda, Promois® W-32CAQ, SiIk CAQ, WG CAQ from Seiwa Kasei or Quat-Coll® CDMA sold by Brooks,
- Guar hydroxypropyltrimethylammonium chloride amino-functional polydimethylsiloxanes or hydroxylamine-modified silicones, such as the commercial products ABIL® Quat 3272 and ABIL® Quat 3474 from Evonik Goldschmidt, Dow Corning® 929 emulsion, Dow Corning® 939 from Dow Corning.
- hair treatment compositions according to the invention are the hair treatment compositions according to the invention and hair aftertreatment z.
- these z. B 0.1 to 5 wt .-% film-forming, in aqueous or aqueous-alcoholic media-soluble polymers, optionally together with cationic surfactants or cationic polymers.
- film formers are z. B.
- homopolymers of vinylpyrrolidone homopolymers of N-vinylformamide, copolymers of vinylpyrrolidone and vinyl acetate, terpolymers of vinylpyrrolidone vinyl acetate and vinyl propionate, polyacrylamides, polyvinyl alcohols, high molecular weight polyethylene glycol or high molecular weight copolymers of ethylene glycol with propylene glycol, chitosan.
- Luviskol® K30, K60, K80, VA37E from BASF
- PVP / VA E335 and PVP K30 from ISP.
- Typical frame formulations for the respective applications are known in the art and are included, for example, in the brochures of the manufacturers of the respective basic substances and active ingredients. These existing formulations can usually be adopted unchanged. If necessary, the desired Modifications, however, are made without complications by simple experiments.
- the hair treatment compositions and hair aftertreatment compositions according to the invention which comprise the etherguanidines according to the invention additionally comprise, in addition to the ether guanidines, from 0 to 10% by weight, preferably from 0.1 to 7.5% by weight, of one or more emulsifiers, from 0 to 10% by weight, preferably from 0.1 to 7.5% by weight, of one or more consistency factors, from 0.1 to 7.5% by weight, preferably from 0.1 to 5% by weight one or more of the abovementioned cationic surfactants and / or polymers having one or more quaternary ammonium groups and / or from 0 to 20% by weight, preferably from 0.1 to 17.5% by weight, of one or more cosmetic oils or emollients as well as customary auxiliaries and additives in usual concentrations.
- the hair treatment compositions and hair aftertreatment agents according to the invention contain as cationic surfactants or polymers with one or more quaternary ammonium groups one or more compounds selected from the group comprising cetrimonium chloride, dicetyldimonium chloride, Behe ntr imo ni umch 1 orid, Di ar ar y 1 dimenum iumchlor or id, behentrimonium methosulfate, distearoylethyldimonium chloride,
- Hydroxypropyltrimoniumchlorid hydroxypropylguar hydroxypropyltrimonium chloride, or quaternium-80 or amine derivatives such as aminopropyldimethicone or Stearamidopropyldimethylamine.
- Such preferred agents are particularly suitable to be used as a hair rinse, Intensivkur, leave-in conditioner or shampoo.
- a typical hair conditioner / conditioner formulation includes, for example:
- a typical formulation for a hair shampoo contains, for example:
- hair treatment compositions or hair treatment compositions according to the invention for chemical hair treatment it may be, for. B. agents for permanent deformation of hair such as perming and fixing or hair relaxers, color-modifying agents such as Blondierstoff, oxidation dyes and tints and shampoos based on substantive dyes.
- agents for permanent deformation of hair such as perming and fixing or hair relaxers, color-modifying agents such as Blondierstoff, oxidation dyes and tints and shampoos based on substantive dyes.
- the preparations according to the invention for the chemical treatment of the hair may, in addition to the ether guanidines according to the invention and their salts, contain further components which are customarily used for the respective application.
- a permanent wave solution e.g. 1 to 10 wt .-% thioglycolic acid, thioglycolic acid salts or esters.
- Perming agents or bleaching agents preferably contain from 2 to 10% by weight of oxidizing agent, e.g.
- Hair relaxers are preferably based on the use of strong bases or on reducing agents, e.g.
- Hair dyes preferably contain substantive
- the substantive dyes are preferably selected from the nitrophenylenediamines, the nitroaminophenols, the azo dyes, the anthraquinones or the indophenols.
- Particularly preferred substantive dyes are those under the international designations or trade names HC Yellow 2, HC Yellow 4, HC Yellow 5, HC Yellow 6, HC Yellow 12, Acid Yellow 1, Acid Yellow 10, Acid Yellow 23, Acid Yellow 36, HC Orange Red 1, HC Red 3, HC Red 10, Red Red HC, HC Red 13, Acid Red 33, Acid Red 52, HC Red BN, Pigment Red 57: 1, HC Blue 2, HC Blue 12, Disperse Blue 3, Acid Blue 7, Acid Green 50, HC Violet 1, Disperse Violet 1, Disperse Violet 4, Acid Violet 43, Disperse Black 9, Acid Black 1, and Acid Black 52 known compounds and 1, 4-diamino-2-nitrobenzene, 2-amino-4-nitrophenol, 1,4-bis (.beta.-hydroxyethyl) amino-2-nitrobenzene, 3-nitro -4- ( ⁇ -hydroxy
- the hair treatment compositions and hair aftertreatment compositions according to the invention can contain further cosmetic auxiliary ⁇ and additives which are usual in such preparations.
- auxiliaries are, for example, solubilizers such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerol and diethylene glycol, complexing agents such as EDTA, NTA, ⁇ -alaninediacetic acid and phosphonic acid, preservatives, antioxidants, fragrances, dyes for coloring the cosmetic preparation, opacifiers such as latex, styrene / PVP and styrene-acrylamide copolymers, pearlescing agents such as ethylene glycol mono- and distearate and PEG-3-distearate, pigments, light stabilizers, thickeners and / or blowing agents.
- solubilizers such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerol and diethylene glycol
- the preparation of the hair treatment compositions or hair aftertreatment agents according to the invention can be carried out in the usual way, wherein the ether guanine both in the aqueous as can also be solved in the oil phase.
- the adjustment of the pH can preferably be carried out last by adding the appropriate acid and / or the buffer mixture.
- the etherguanidines according to the invention and / or the hair treatment compositions and hair aftertreatment agents according to the invention may, for. B. for the preparation of hair shampoo, leave-in formulations or as an active component in cosmetic formulations with anti-dandruff action are used. Because of their mild microbiocidal activity, the ether guanedines of the general formula (I) can be used or used in particular as active ingredients in mild anti-dandruff formulations.
- the remaining ether guanidines were prepared analogously based on the Tomamine® PAl4, PA1618 and PAl7.
- the damaged hair was treated with the example formulations.
- customary formulation methods known to the person skilled in the art were used.
- the compositions of the formulations are shown in Tables 1 and 2.
- the improvement of the mechanical resistance of damaged hair by alkylguanidinium compounds was determined by pairwise comparison of single hairs before and after treatment with the test formulation.
- the hair was dipped for at least 30 minutes in a water bath for recovery.
- Table 5 Formulations for testing the hair sensor system (in% by weight)
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP09769090A EP2300418A1 (de) | 2008-06-27 | 2009-05-28 | Haarbehandlungsmittel und haarnachbehandlungsmittel zum schutz vor schäden durch chemische behandlung und zur reparatur bereits geschädigter haare enthaltend als wirksubstanzen etherguanidine |
CN2009801219827A CN102056896A (zh) | 2008-06-27 | 2009-05-28 | 用于防止化学处理损伤和用于修复已受损头发的含有醚胍作为活性物质的头发处理组合物和头发后处理组合物 |
US13/001,562 US8642659B2 (en) | 2008-06-27 | 2009-05-28 | Hair treatment product and hair after-treatment product containing ether guanidines as active substances, for protecting from damage caused by chemical treatment and for repairing already damaged hair |
JP2011515275A JP2011525515A (ja) | 2008-06-27 | 2009-05-28 | 化学処理による損傷からの保護用およびすでに損傷している頭髪の修復用の、エーテルグアニジンを有効物質として含むヘアトリートメント組成物およびヘアアフタートリートメント組成物 |
BRPI0913984A BRPI0913984A2 (pt) | 2008-06-27 | 2009-05-28 | produto para o tratamento capilar e produto para pós-tratamento capilar conotendo éter guanidinas com substâncias ativas para proteção contra danos causados por tratamento químico e para reparar cabelos já danificados |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102008002707.3 | 2008-06-27 | ||
DE102008002707A DE102008002707A1 (de) | 2008-06-27 | 2008-06-27 | Haarbehandlungsmittel und Haarnachbehandlungsmittel zum Schutz vor Schäden durch chemische Behandlung und zur Reparatur bereits geschädigter Haare enthaltend als Wirksubstanzen Etherguanidine |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2009156241A1 true WO2009156241A1 (de) | 2009-12-30 |
Family
ID=41228453
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2009/056492 WO2009156241A1 (de) | 2008-06-27 | 2009-05-28 | Haarbehandlungsmittel und haarnachbehandlungsmittel zum schutz vor schäden durch chemische behandlung und zur reparatur bereits geschädigter haare enthaltend als wirksubstanzen etherguanidine |
Country Status (7)
Country | Link |
---|---|
US (1) | US8642659B2 (de) |
EP (1) | EP2300418A1 (de) |
JP (1) | JP2011525515A (de) |
CN (1) | CN102056896A (de) |
BR (1) | BRPI0913984A2 (de) |
DE (1) | DE102008002707A1 (de) |
WO (1) | WO2009156241A1 (de) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011023465A3 (de) * | 2009-08-31 | 2012-02-16 | Evonik Goldschmidt Gmbh | Antimikrobielle etherguanidine |
CN106833587A (zh) * | 2016-12-28 | 2017-06-13 | 浙江海洋大学 | 一种基于餐厨废弃油脂的生物油羟基磺酸盐制备方法 |
US10995174B2 (en) | 2017-09-25 | 2021-05-04 | Evonik Operations Gmbh | Production of polyurethane systems |
Families Citing this family (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102013223444B4 (de) | 2013-11-18 | 2015-06-03 | Evonik Industries Ag | Verwendung von Guanidinumsetzungsprodukten bei der Herstellung von Polyurethansystemen |
RU2746990C2 (ru) | 2015-05-01 | 2021-04-23 | Л'Ореаль | Применение активных агентов при химической обработке |
US10080714B2 (en) * | 2015-11-19 | 2018-09-25 | Avon Products, Inc. | Peptides and their use in the treatment of hair |
ES2893123T3 (es) * | 2015-11-24 | 2022-02-08 | Oreal | Composiciones de tratamiento del cabello |
WO2017091800A1 (en) * | 2015-11-24 | 2017-06-01 | L'oreal | Compositions for treating the hair |
RU2771234C2 (ru) | 2015-11-24 | 2022-04-28 | Л'Ореаль | Композиции для обработки волос |
WO2017091797A1 (en) | 2015-11-24 | 2017-06-01 | L'oreal | Compositions for treating the hair |
WO2017214497A1 (en) | 2016-06-10 | 2017-12-14 | Clarity Cosmetics Inc. | Non-comedogenic hair and scalp care formulations and method for use |
MX2019000424A (es) | 2016-07-19 | 2019-03-28 | Evonik Degussa Gmbh | Uso de poliolesteres para la produccion de revestimientos plasticos porosos. |
CN109715129A (zh) * | 2016-10-05 | 2019-05-03 | 荷兰联合利华有限公司 | 毛发处理组合物 |
US11135150B2 (en) | 2016-11-21 | 2021-10-05 | L'oreal | Compositions and methods for improving the quality of chemically treated hair |
US11433011B2 (en) | 2017-05-24 | 2022-09-06 | L'oreal | Methods for treating chemically relaxed hair |
US10660838B2 (en) | 2017-06-23 | 2020-05-26 | The Procter & Gamble Company | Composition and method for improving the appearance of skin |
CN113616552A (zh) | 2017-12-29 | 2021-11-09 | 欧莱雅 | 用于改变毛发颜色的组合物 |
WO2019183694A1 (en) * | 2018-03-29 | 2019-10-03 | L'oreal | Compositions and methods for treating the hair |
US11622963B2 (en) | 2018-07-03 | 2023-04-11 | The Procter & Gamble Company | Method of treating a skin condition |
US11090249B2 (en) | 2018-10-31 | 2021-08-17 | L'oreal | Hair treatment compositions, methods, and kits for treating hair |
RU2741386C2 (ru) * | 2019-05-24 | 2021-01-25 | Общество С Ограниченной Ответственностью "Сплат Глобал" | Композиция для ухода за волосами и косметическое средство для ухода за волосами, ее содержащее |
US11419809B2 (en) | 2019-06-27 | 2022-08-23 | L'oreal | Hair treatment compositions and methods for treating hair |
US11583488B2 (en) | 2020-06-01 | 2023-02-21 | The Procter & Gamble Company | Method of improving penetration of a vitamin B3 compound into skin |
US10959933B1 (en) | 2020-06-01 | 2021-03-30 | The Procter & Gamble Company | Low pH skin care composition and methods of using the same |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH1135546A (ja) * | 1997-07-22 | 1999-02-09 | Kao Corp | グアニジン誘導体及びこれを含有する毛髪化粧料 |
US20050136017A1 (en) * | 2003-11-18 | 2005-06-23 | Gerard Malle | Hair relaxing composition comprising at least one non-hydroxide imine |
EP1671615A2 (de) * | 2004-12-20 | 2006-06-21 | Goldschmidt GmbH | Verwendung von Alkylguanidinen als kationische Emulgatoren |
Family Cites Families (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE506282C (de) | 1926-10-29 | 1930-09-01 | Schering Kahlbaum Akt Ges | Verfahren zur Darstellung hochalkylierter Guanidine |
US2016962A (en) | 1932-09-27 | 1935-10-08 | Du Pont | Process for producing glucamines and related products |
US1985424A (en) | 1933-03-23 | 1934-12-25 | Ici Ltd | Alkylene-oxide derivatives of polyhydroxyalkyl-alkylamides |
US2703798A (en) | 1950-05-25 | 1955-03-08 | Commercial Solvents Corp | Detergents from nu-monoalkyl-glucamines |
GB1112307A (en) * | 1964-11-10 | 1968-05-01 | American Cyanamid Co | Alkoxyalkylguanidines and their salts |
DE3723354A1 (de) | 1987-07-15 | 1989-01-26 | Henkel Kgaa | Sulfatierte hydroxy-mischether, verfahren zu ihrer herstellung und ihre verwendung |
DE3725030A1 (de) | 1987-07-29 | 1989-02-09 | Henkel Kgaa | Oberflaechenaktive hydroxysulfonate |
DE3926344A1 (de) | 1989-08-09 | 1991-02-28 | Henkel Kgaa | Verfahren zur herstellung von hellfarbigen oelsaeuresulfonaten |
JPH06501688A (ja) | 1990-10-12 | 1994-02-24 | ザ、プロクター、エンド、ギャンブル、カンパニー | ヒドロキシ溶剤中におけるn−アルキルポリヒドロキシアミンおよびそれからの脂肪酸アミドの製造法 |
DE4038478A1 (de) | 1990-12-03 | 1992-06-04 | Henkel Kgaa | Verfahren zur herstellung von partialglyceridsulfaten |
DE4038477A1 (de) | 1990-12-03 | 1992-06-04 | Henkel Kgaa | Verfahren zur kontinuierlichen herstellung von partialglyceridsulfaten |
US5136093A (en) | 1991-02-06 | 1992-08-04 | Smith Ronald J | Quaternized panthenol compounds and their use |
DE4204700A1 (de) | 1992-02-17 | 1993-08-19 | Henkel Kgaa | Verfahren zur abtrennung anorganischer salze |
DE69516584T2 (de) | 1994-06-27 | 2001-01-04 | Kao Corp | Verfahren zur Herstellung von Amidoethercarbonsäure oder deren Salz und diese enthaltende oberflächenaktive Mischung |
JP2853020B2 (ja) * | 1994-07-26 | 1999-02-03 | 花王株式会社 | グアニジン誘導体及びその製造方法 |
TW300883B (de) | 1994-07-26 | 1997-03-21 | Kao Corp | |
US5939078A (en) | 1995-11-20 | 1999-08-17 | Kao Corporation | Wrinkle-care product |
DE19736906A1 (de) | 1997-08-25 | 1999-03-04 | Henkel Kgaa | Verfahren zur Herstellung von sulfatierten Fettsäurealkylenglykolestern |
DE19738866A1 (de) | 1997-09-05 | 1999-03-11 | Henkel Kgaa | Schaumarme Tensidmischungen mit Hydroxymischethern |
US6576794B2 (en) | 2000-12-28 | 2003-06-10 | Kao Corporation | Process for production of ether amine |
US20020172655A1 (en) | 2001-03-01 | 2002-11-21 | Mitsubishi Chemical Corporation | Cosmetic-use polymer, cosmetic employing same, and method of preparing same |
EP1493423B1 (de) | 2003-06-18 | 2006-06-14 | Goldschmidt GmbH | Haarbehandlungsmittel und Haarnachbehandlungsmittel zum Schutz vor Schäden durch chemische Behandlung und zur Reparatur bereits geschädigter Haare enthaltend als Wirksubstanz Alkylguanidin-Verbindungen |
DE10327871A1 (de) | 2003-06-18 | 2005-01-05 | Goldschmidt Ag | Verwendung von Alkylguanidin-Verbindungen zur Behandlung und Nachbehandlung von Haaren |
US20050129645A1 (en) | 2003-11-18 | 2005-06-16 | L'oreal | Hair shaping composition comprising at least one non-hydroxide imine |
-
2008
- 2008-06-27 DE DE102008002707A patent/DE102008002707A1/de not_active Withdrawn
-
2009
- 2009-05-28 WO PCT/EP2009/056492 patent/WO2009156241A1/de active Application Filing
- 2009-05-28 US US13/001,562 patent/US8642659B2/en not_active Expired - Fee Related
- 2009-05-28 BR BRPI0913984A patent/BRPI0913984A2/pt not_active IP Right Cessation
- 2009-05-28 EP EP09769090A patent/EP2300418A1/de not_active Withdrawn
- 2009-05-28 CN CN2009801219827A patent/CN102056896A/zh active Pending
- 2009-05-28 JP JP2011515275A patent/JP2011525515A/ja not_active Ceased
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH1135546A (ja) * | 1997-07-22 | 1999-02-09 | Kao Corp | グアニジン誘導体及びこれを含有する毛髪化粧料 |
US20050136017A1 (en) * | 2003-11-18 | 2005-06-23 | Gerard Malle | Hair relaxing composition comprising at least one non-hydroxide imine |
EP1671615A2 (de) * | 2004-12-20 | 2006-06-21 | Goldschmidt GmbH | Verwendung von Alkylguanidinen als kationische Emulgatoren |
Non-Patent Citations (2)
Title |
---|
AIR PRODUCTS: "Tomamine Ether Amines Product Guide", 2008, AIRPRODUCTS AND CHEMICALS INC, ALLENTOWN USA, XP002553897 * |
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; NAGAI, MINORU ET AL: "Guanidines and hair cosmetics containing them", XP002553894, retrieved from STN Database accession no. 130:213456 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011023465A3 (de) * | 2009-08-31 | 2012-02-16 | Evonik Goldschmidt Gmbh | Antimikrobielle etherguanidine |
CN106833587A (zh) * | 2016-12-28 | 2017-06-13 | 浙江海洋大学 | 一种基于餐厨废弃油脂的生物油羟基磺酸盐制备方法 |
US10995174B2 (en) | 2017-09-25 | 2021-05-04 | Evonik Operations Gmbh | Production of polyurethane systems |
Also Published As
Publication number | Publication date |
---|---|
CN102056896A (zh) | 2011-05-11 |
EP2300418A1 (de) | 2011-03-30 |
US8642659B2 (en) | 2014-02-04 |
US20110117219A1 (en) | 2011-05-19 |
DE102008002707A1 (de) | 2009-12-31 |
JP2011525515A (ja) | 2011-09-22 |
BRPI0913984A2 (pt) | 2015-10-20 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP2300418A1 (de) | Haarbehandlungsmittel und haarnachbehandlungsmittel zum schutz vor schäden durch chemische behandlung und zur reparatur bereits geschädigter haare enthaltend als wirksubstanzen etherguanidine | |
EP2037877B1 (de) | Anti schuppen-shampoo | |
EP1935878B1 (de) | Gesteigerte Befeuchtungswirksamkeit durch Verwendung eines Hydroxyalkylharnstoff | |
EP1812117B1 (de) | Verfahren zur restrukturierung keratinischer fasern | |
EP1493423B1 (de) | Haarbehandlungsmittel und Haarnachbehandlungsmittel zum Schutz vor Schäden durch chemische Behandlung und zur Reparatur bereits geschädigter Haare enthaltend als Wirksubstanz Alkylguanidin-Verbindungen | |
AU2004231260A1 (en) | Increased moisturization efficacy using hydroxyalkylurea | |
DE102015223196A1 (de) | Mittel und Verfahren zur Reinigung und/oder zur Pflege geschädigter keratinischer Fasern | |
EP2049073A1 (de) | Mittel zur bekämpfung von kopfhautschuppen | |
EP1228748B1 (de) | Haarpflegemittel mit diquaternären Silikonpolymeren | |
EP1009367B1 (de) | Verwendung einer wirkstoffkombination und mittel zum schutz von keratinischen fasern | |
EP1752138B1 (de) | Amaranthsamenöl in Haarbehandlungsmitteln | |
EP2263645B1 (de) | Stylingmittel mit hohem Haltegrad bei Feuchtigkeit | |
DE102008036073A1 (de) | Reinigungsmittel mit Terpolymer | |
DE102009028207A1 (de) | Haarbehandlungsmittel mit Polyether-modifizierten Feststoffpartikeln und haarfestigenden Polymeren | |
DE102016218984A1 (de) | "verbessert konditionierende Haarbehandlungsmittel mit Auswaschschutz" | |
DE102004045253A1 (de) | Kationische Copolymere und ihre Verwendung in haarkosmetischen Zubereitungen | |
EP2391339B1 (de) | Farberhaltende haarbehandlungsmittel | |
DE102017218980A1 (de) | "Strukturkräftigende Haarbehandlungsmittel mit gesteigerter Pflegewirkung " | |
DE102016219009A1 (de) | Verbessert konditionierende Haarbehandlungsmittel mit Auswaschschutz | |
DE102016218989A1 (de) | verbessert konditionierende Haarbehandlungsmittel mit Auswaschschutz | |
DE102016218987A1 (de) | verbessert konditionierende Haarbehandlungsmittel mit Auswaschschutz | |
EP2489345A1 (de) | Stylingmittel mit hohem Haltegrad bei Feuchtigkeit III | |
DE102016218999A1 (de) | Verbessert konditionierende Haarbehandlungsmittel mit Auswaschschutz | |
DE102015223855A1 (de) | Leistungsstarke Haarbehandlungsmittel mit Anti-Auswasch-Effekt | |
WO2008028775A1 (de) | Mittel, enthaltend biochinone und betaine |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
WWE | Wipo information: entry into national phase |
Ref document number: 200980121982.7 Country of ref document: CN |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 09769090 Country of ref document: EP Kind code of ref document: A1 |
|
ENP | Entry into the national phase |
Ref document number: 2011515275 Country of ref document: JP Kind code of ref document: A |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2009769090 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 13001562 Country of ref document: US |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
ENP | Entry into the national phase |
Ref document number: PI0913984 Country of ref document: BR Kind code of ref document: A2 Effective date: 20101227 |