EP2249778A1 - Tensio-actifs cationiques présentant des propriétés améliorées - Google Patents

Tensio-actifs cationiques présentant des propriétés améliorées

Info

Publication number
EP2249778A1
EP2249778A1 EP08801595A EP08801595A EP2249778A1 EP 2249778 A1 EP2249778 A1 EP 2249778A1 EP 08801595 A EP08801595 A EP 08801595A EP 08801595 A EP08801595 A EP 08801595A EP 2249778 A1 EP2249778 A1 EP 2249778A1
Authority
EP
European Patent Office
Prior art keywords
acid
carbon atoms
fatty
oil
cationic surfactants
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP08801595A
Other languages
German (de)
English (en)
Inventor
Ansgar Behler
Frank Clasen
Hans-Martin Haake
Monika Barbenheim
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Cognis IP Management GmbH
Original Assignee
Cognis IP Management GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Cognis IP Management GmbH filed Critical Cognis IP Management GmbH
Priority to EP08801595A priority Critical patent/EP2249778A1/fr
Publication of EP2249778A1 publication Critical patent/EP2249778A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing 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
    • A61K8/41—Amines
    • A61K8/416—Quaternary ammonium compounds
    • 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

Definitions

  • the invention is in the field of cationic surfactants and the cosmetic preparations containing these surfactants.
  • An important aspect of hair care is the conditioning of hair, e.g. after washing, as these daily different influencing factors such as sunlight, pollution or chlorinated water, but also various Behanlditch such as washing, bleaching, dyeing, waves. Combing or blow drying are exposed. All of this, on its own or in combination, can lead to hair damage, which may manifest as the hair surface becomes rougher. In addition, damaged hair has been found to have hydrophilization of the surface, an increase in the negative charges on the hair, and decreased mechanical stability. This then causes the hair to comb only bad, breaks fast and has split ends on the hair ends. The grip changes to the detriment and the natural shine of the hair is lost.
  • conditioners are used in cosmetic hair treatment agents, which increase the combing.
  • the electrostatic charge of the hair is prevented or minimized, the hair shines again and its surface is again significantly more hydrophobic.
  • the mechanical strength of hair is increased by conditioning, even during the otherwise harmful chemical treatments.
  • exemplary here are consistency or lipophilic conditioning agents such as fatty alcohols or partial glycerides called.
  • secondary conditioning agents silicones are used.
  • emulsifiers such as fat alcohol ethoxylates or alkyl polyglycosides or polymers, humectants or thickeners are said to have conditioning properties.
  • cationic surfactants are still to be mentioned as a conditioning component in cosmetic preparations. These are usually alkylammonium compounds with at least one long alkyl chain in the molecule. As a counterion, a halide such as chloride or methosulfate is often present. Examples of such cationic surfactants are cetrimonium chlorides, distearoyl hydroxyethylmonium methosulfate, distearyldimonium chlorides or behentrimonium chlorides.
  • the object of the present patent application has been to provide new cationic conditioning agents which do not have the above-mentioned disadvantages but nevertheless have excellent conditioning properties.
  • the present application therefore relates to cationic surfactants of the formula (I)
  • R1 is a saturated or unsaturated, branched or linear alkyl radical having 6 to 22 carbon atoms
  • R2 and R3 are independently alkyl radicals having 1 to 3 carbon atoms or hydrogen
  • n is 2 or 3
  • X is halogen, deprotonated carboxylic acids or methosulfate stand.
  • surfactants according to formula (I) are used in which R 1 is a saturated or unsaturated, branched or linear alkyl radical having 12 to 22 carbon atoms, R 2 is methyl and R 3 is methyl or hydrogen, n is 2 and X is chlorine ,
  • the surfactants of the formula (I) having a longer alkyl chain R1 are characterized by better conditioning properties, as demonstrated in the examples.
  • R 1 is a saturated or unsaturated, branched or linear alkyl radical having 18 to 22 carbon atoms.
  • the above-mentioned cationic surfactants are used for the preparation of cosmetic preparations. They are used as conditioning agents in these preparations.
  • the amounts used in these preparations are in proportions of 0.1 to 20 wt.%, Preferably from 0.1 to 10 wt.% And particularly preferably from 0.5 to 5 wt.% Based on the total formulation.
  • radical X for the deprotonated carboxylic acids mentioned as radical X, in particular organic acids such as citric acid, lactic acid or acetic acid are suitable.
  • the cosmetic preparations may be a variety of surfactant-based formulations, such as shampoos, conditioners, shower baths, shower gels, bubble baths, oil baths, 2-in-1 shampoos and the like.
  • the cationic surfactants of the formula (I) according to the invention can be used in detergents and cleaners, for example in cleaners for cleaning hard surfaces or in dishwashing detergents, both for manual and machine cleaning.
  • These agents may contain, as further auxiliaries and additives, mild surfactants, oil bodies, emulsifiers, pearlescent waxes, superfatting agents, stabilizers, polymers, silicone compounds, fats, waxes, lecithins, phospholipids, biogenic active ingredients, UV protection factors, antioxidants, deodorants, antiperspirants, antidandruff agents - tel, film formers, swelling agents, insect repellents, self-tanner, tyrosine inhibitors (depigmenting agents), hydrotropes, solubilizers, preservatives, perfume oils, dyes and the like.
  • Surfactants which may be present are anionic, nonionic, cationic and / or amphoteric or zwitterionic surfactants whose proportion of the agents is usually from about 1 to 70, preferably from 5 to 50 and in particular from 10 to 30% by weight.
  • anionic surfactants are soaps, alkylbenzenesulfonates, alkanesulfonates, olefinsulfonates, alkyl ether sulfonates, glycerol ether sulfonates, ⁇ -methyl ester sulfonates, sulfo fatty acids, alkyl sulfates, fatty alcohol ether sulfates, glycerol ether sulfates, fatty acid ether sulfates, hydroxy mixed ether sulfates, monoglyceride (ether) sulfates, fatty acid amide (ether) sulfates, mono and alkoxylated and non-alkoxylated dialkylsulfosuccinates, mono- and dialkylsulfosuccinamates, sulfotriglycerides, amide sisides, ethercarboxylic acids and their salts, fatty acid isethionates
  • anionic surfactants contain polyglycol ether chains, these may have a conventional, but preferably a narrow homolog distribution.
  • Typical examples of nonionic surfactants are fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol esters, fatty acid amide polyglycol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, mixed ethers, optionally partially oxidized alk (en) yloligoglycosides or glucuronic acid derivatives, fatty acid N-alkylglucamides, protein hydrolysates ( in particular vegetable products based on wheat), polyol fatty acid esters, sugar esters, sorbitan esters, poly-sorbates and amine oxides.
  • nonionic surfactants contain polyglycol ether chains, these may have a conventional, but preferably a narrow homolog distribution.
  • Typical examples of cationic surfactants are quaternary Ammonium compounds, such as, for example, dimethyl distearyl ammonium chloride or cetyl trimonium chloride, and ester quats, in particular quaternized fatty acid trialkanolamine ester salts.
  • amphoteric or zwitterionic surfactants are alkyl betaines, alkyl amidobetaines, aminopropionates, aminoglycinates, imidazolinium betaines and sulfobetaines.
  • the surfactants mentioned are exclusively known compounds.
  • particularly skin-compatible surfactants are fatty alcohol polyglycol ether sulfates, monoglyceride sulfates, mono- and / or dialkyl sulfosuccinates, fatty acid isethionates, fatty acid sarcosinates, fatty acid taurides, fatty acid glutamates, ⁇ -olefinsulfonates, ethercarboxylic acids, alkyloligoglucosides, fatty acid glucamides, alkylamidobetaines, amphoacetals and / or protein fatty acid condensates, the latter preferably based on wheat proteins.
  • Carboxylic acids with linear or branched C 6 -C 22 -fatty alcohols such as, for example, myristyl myristate, myristyl palmitate, myristyl stearate, myristyl isostearate, myristyl oleate, myristyl behenate, myristyl erucate, cetyl myristate, cetyl palmitate, cetyl stearate, cetyl isosteate, cetyl oleate, cetyl behenate, cetyl erucate, stearyl myristate, stearyl palmitate, Stearylstea- rat, tribehenate Steary
  • esters of linear C 6 -C 22 -fatty acids with branched alcohols in particular 2-ethylhexanol, esters of C 18 -C 38 -alkylhydroxycarboxylic acids with linear or branched C 6 -C 22 fatty alcohols, in particular dioctyl malates, esters of linear and / or branched fatty acids with polyhydric alcohols (such as propylene glycol, dimerdiol or trimer triol) and / or Guerbet alcohols, triglycerides Based on C 6 -Cio fatty acids, liquid mono- / di- / triglyceride mixtures based on C 6 - C 8 fatty acids, esters of C 6 -C 22 fatty alcohols and / or Guerbet alcohols with aromatic carboxylic acids, in particular benzoic acid, esters of C C 2 -C 2 -dicarboxylic acids with linear or branched alcohols having 1 to 22 carbon
  • Suitable emulsifiers are nonionic surfactants from at least one of the following groups:
  • Block copolymers e.g. Polyethylene glycol-30 dipolyhydroxystearates
  • Alkyl and / or alkenyl oligoglycosides their preparation and their use are known from the prior art. They are prepared in particular by reacting glucose or oligosaccharides with primary alcohols having 8 to 18 carbon atoms.
  • the glycoside radical both monoglycosides in which a cyclic sugar residue is glycosidically linked to the fatty alcohol and oligomeric glycosides having a degree of oligomerization of preferably approximately 8 are suitable.
  • the degree of oligomerization is a statistical mean, which is based on a homolog distribution typical for such technical products.
  • Suitable partial glycerides are Hydroxystearin Textremonoglyce- chloride, hydroxystearic acid diglyceride, isostearic acid, Isostearinklaredigly- cerid, oleic acid monoglyceride, oleic acid diglyceride, Ricinolklaremoglycerid, diglyceride Ricinolklare-, Linolklaremonoglycerid, Linolklarediglycerid, LinolenTalkremonoglycerid, Linolenchurediglycerid, Erucaklaklamonoglycerid, Erucaklakladiglycerid, Weinklaremo- noglycerid, Weinklarediglycerid, Citronenklamonoglycerid, Citronendiglycerid, Citronendiglycerid, Acid monoglyceride, malic acid diglyceride and their technical mixtures, which may contain minor amounts of triglyceride subordinate to the manufacturing process. Also suitable are addition
  • sorbitan sorbitan As sorbitan sorbitan, sorbitan sesquiisostearate, sorbitan diisostearate, sorbitan triisostearate, sorbitan monooleate, sorbitan dioleate, trioleate, Sorbitanmonoerucat, Sorbitansesquierucat, sorbitan come dierucat, Sorbitantrierucat, Sorbitanmonoricinoleat, Sorbitansesquiricinoleat, Sorbitandi- ricinoleate, sesquihydroxystearat Sorbitantriricinoleat, Sorbitanmonohydroxystearat, sorbitan, Sorbitandihydroxystearat , Sorbitan trihydroxystearate, sorbitan monotartrate, sorbitan sesquivar tartrate, sorbitan ditartrate, sorbitan tritartrate, sorbitan monocitrate, sorbitan siccitrate, sorb
  • polyglycerol esters are polyglyceryl-2-dipolyhydroxystearates (Dehymuls® PGPH), polyglycerol-3-diisostearates (Lameform® TGI), polyglyceryl-4 isostearates (Isolan® GI 34), polyglyceryl-3-oleates, diisostearoyl polyglycerol 3 diisostearates (Isolan® PDI), polyglyceryl-3-methylglucose distearate (Tego Carre® 450), polyglyceryl-3 beeswax (Cera Bellina®), polyglyceryl-4-caprate (polyglycerol caprate T2010 / 90), polyglyceryl-3-cetyl ether ( Chimexane® NL) 1 polyglyceryl-3 distearate (Cremophor® GS 32) and polyglyceryl polyricinoleate (Admul® WOL 1403) polyglycerol
  • polystyrene resin examples include the mono-, di- and triesters of trimethylolpropane or pentaerythritol with lauric acid, coconut fatty acid, tallow fatty acid, palmitic acid, stearic acid, oleic acid, behenic acid and the like optionally reacted with from 1 to 30 mol of ethylene oxide.
  • Typical anionic emulsifiers are aliphatic fatty acids having 12 to 22 carbon atoms, such as palmitic acid, stearic acid or behenic acid, and dicarboxylic acids having 12 to 22 carbon atoms, such as azelaic acid or sebacic acid.
  • zwitterionic surfactants can be used as emulsifiers.
  • Zwitterionic surfactants are those surface-active compounds which carry at least one quaternary ammonium group and at least one carboxylate and one sulfonate group in the molecule.
  • Particularly suitable zwitterionic surfactants side are the so-called betaines such as the N-alkyl-N, N-dimethylammoniumglycinate, for example Kokosalkyldimethylammoniumglycinat, N-acylaminopropyl-NN-dimethylammonium glycinate, for example, the Kokosacylaminopropyldimethyl- ammoniumglycinat, and 2-alkyl-3-carboxylmethyl-3-hydroxyethylimidazoline with in each case 8 to 18 C atoms in the alkyl or acyl group and the Kokosacylaminoethyl- hydroxyethylcarboxymethylglycinat.
  • betaines such as the N-alkyl-N, N-dimethylammoniumglycinate, for example Kokosalkyldimethylammoniumglycinat, N-acylaminopropyl-NN-dimethylammonium glycinate,
  • fatty acid amide derivative known by the CTFA name Cocamidopropyl Betaine.
  • ampholytic surfactants are surface-active compounds which, apart from a C8 / i 8 - are alkyl or acyl group, contain at least one free amino group and at least one -COOH or -SO ß H group and are capable of forming inner salts.
  • ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and Alkylaminoacetic acids having in each case about 8 to 18 carbon atoms in the alkyl group.
  • ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and
  • cationic surfactants are also suitable as emulsifiers, with those of the esterquat type, preferably methyl-quaternized difatty acid triethanolamine ester salts, being particularly preferred.
  • Typical examples of fats are glycerides, ie solid or liquid vegetable or animal products, which consist essentially of mixed glycerol esters of higher fatty acids
  • waxes include natural waxes, such as candelilla wax, carnauba wax, Japan wax, Espartograswachs, cork wax, guarumewax, rice germ oil wax , Sugarcane wax, ouricury wax, montan wax, beeswax, shellac wax, spermaceti, lanolin (wool wax), crepe fat, ceresin, ozokeht (earth wax), petrolatum, paraffin waxes, microwaxes; chemically modified waxes (hard waxes), such as montan ester waxes, Sasol waxes, hydrogenated jojoba waxes and synthetic waxes, such as polyalkylene waxes and polyethylene glycol waxes in question.
  • natural waxes such as candelilla wax, carnauba wax
  • lecithin In addition to the fats, fat-like substances such as lecithins and phospholipids come into question as additives.
  • lecithin is understood by the specialist those glycerophospholipids which are formed from fatty acids, glycerol, phosphoric acid and choline by esterification. Lecithins are therefore often referred to in the art as Phosphatidylcholine (PC).
  • PC Phosphatidylcholine
  • cephalins which are also referred to as phosphatidic acids and derivatives of 1, 2-diacyl-sn-glycerol-3-phosphoric acids.
  • phospholipids are usually understood as meaning mono- and preferably diesters of phosphoric acid with glycerol (glycerol phosphates), which are generally regarded as fats.
  • glycerol phosphates glycerol phosphates
  • sphingosines or sphingolipids are also suitable.
  • Suitable pearlescing waxes are, for example: alkylene glycol esters, especially ethylene glycol distearate; Fatty acid alkanolamides, especially coconut fatty acid diethanolamide; Partial glycerides, especially stearic acid monoglyceride; Esters of polybasic, optionally hydroxy-substituted carboxylic acids with fatty alcohols having 6 to 22 carbon atoms, especially long-chain esters of tartaric acid; Fatty substances, such as fatty alcohols, fatty ketones, fatty aldehydes, fatty ethers and fatty carbonates, which in total have at least 24 carbon atoms, especially lauron and distearyl ether; Fatty acids such as stearic acid, hydroxystearic acid or behenic acid, ring-opening products of olefin epoxides having 12 to 22 carbon atoms with fatty alcohols having 12 to 22 carbon atoms and / or polyols having 2 to 15 carbon atoms
  • substances such as lanolin and lecithin as well as polyethoxylated or acylated lanolin and lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides can be used, the latter also serving as foam stabilizers.
  • stabilizers are especially used, the latter also serving as foam stabilizers.
  • metal salts of fatty acids e.g. Magnesium, aluminum and / or zinc stearate or ricinoleate can be used.
  • Suitable cationic polymers are, for example, cationic cellulose derivatives, e.g. a quaternized hydroxyethylcellulose available under the name Polymer JR 400® from Amerchol, cationic starch, copolymers of diallylammonium salts and acrylamides, quaternized vinylpyrrolidone / vinylimidazole polymers, e.g.
  • Luviquat® condensation products of polyglycols and amines, quaternized collagen polypeptides, such as lauryldimonium hydroxypropyl hydrolysed collagen (Lamequat®L / Grünau), quaternized wheat polypeptides, polyethylenimine, cationic silicone polymers, such as e.g.
  • Amodimethicones, copolymers of adipic acid and dimethylaminohydroxypropyldiethylenetriamine (Cartaretine® / Sandoz), copolymers of acrylic acid with dimethyldiallylammonium chloride (Merquat® 550 / Chemviron), polyamino-polyamides and their crosslinked water-soluble polymers, cationic chitin derivatives such as quaternized chitosan, optionally microcrystalline dispersed, condensation products from dihaloalkylene, such as Dibromobutane with bis-dialkylamines, such as Bis-dimethylamino-1,3-propane, cationic guar gum, e.g. Jaguar® CBS, Jaguar® C-17, Jaguar® C-16 from Celanese, quaternized ammonium salt polymers, e.g. Mirapol® A-15, Mirapol® AD-1, Mirapol® AZ-1 from Miranol.
  • Suitable anionic, zwitterionic, amphoteric and nonionic polymers are, for example, vinyl acetate / crotonic acid copolymers, vinylpyrrolidone / vinyl acrylate copolymers, vinyl acetate / butyl maleate / isobornyl acrylate copolymers, methylvinyl ether / maleic anhydride copolymers and their esters, uncrosslinked polyols crosslinked with polyols, acrylamidopropyltrimethylammonium chloride / Acrylate copolymers, octylacrylamide / methylmethacrylate / tert.butylaminoethylmethacrylate / 2-hydroxypropylmethacrylate copolymers, polyvinylpyrrolidone, vinylpyrrolidone / vinylacetate Copolymers, vinylpyrrolidone / dimethylaminoethyl methacrylate / vinylcaprolactam
  • Suitable silicone compounds are, for example, dimethylpolysiloxanes, methylphenylpolysiloxanes, cyclic silicones and amino, fatty acid, alcohol, polyether, epoxy, fluorine, glycoside and / or alkyl-modified silicone compounds which may be both liquid and resin-form at room temperature.
  • trimethicones which are mixtures of dimethicones having an average chain length of from 200 to 300 dimethylsiloxane units and hydrogenated silicates.
  • biogenic active substances include tocopherol, tocopherol acetate, tocopherol analog, ascorbic acid, (deoxy) ribonucleic acid and their fragmentation products, ⁇ -glucans, retinol, bisabolol, allantoin, phytantriol, panthenol, AHA acids, amino acids, ceramides, pseudoceramides, essential oils , Plant extracts, such as Prunus extract, Bambaranussexschreib and vitamin complexes to understand.
  • Typical film formers are, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinylpyrrolidone, vinylpyrrolidone-vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives, collagen, hyaluronic acid or salts thereof and similar compounds.
  • Anti-dandruff agents used are Piroctone olamine (1-hydroxy-4-methyl-6- (2,4,4-trimethylpentyl) -2- (1H) -pyridinone monoethanolamine salt), Baypival® (climbazole), ketoconazole®, (4 Acetyl-1 - ⁇ - 4- [2- (2,4-dichlorophenyl) r-2- (1 H -imidazol-1-ylmethyl) -1,3-dioxylan-c-4-ylmethoxyphenyl ⁇ piperazine, ketoconazole, elubiol, selenium disulfide , Sulfur colloidal, Schwefelpolyehtylenglykolsorbitanmonooleat, Schwefelrizinolpolyehtoxylat, Schwfel-tar distillates, salicylic acid (or in combination with hexachlorophene), undenylenklad, Lame
  • Suitable swelling agents for aqueous phases are montmorillonites, clay minerals, pemulen and alkyl-modified Carbopol types (Goodrich).
  • Hydrotropes such as, for example, ethanol, isopropyl alcohol, or polyols can also be used to improve the flow behavior.
  • Polyols contemplated herein preferably have from 2 to 15 carbon atoms and at least two hydroxyl groups.
  • the polyols may contain other functional groups, in particular amino groups, or be modified with nitrogen. Typical examples are
  • Alkylene glycols such as, for example, ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol and polyethylene glycols having an average molecular weight of from 100 to 1000 daltons;
  • Methylol compounds in particular trimethylolethane, trimethylolpropane, th-methylolbutane, pentaerythritol and dipentaerythritol;
  • Lower alkyl glucosides especially those having 1 to 8 carbons in the alkyl radical, such as, for example, methyl and butyl glucoside;
  • Dialcoholamines such as diethanolamine or 2-amino-1, 3-propanediol.
  • Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid and the silver complexes known under the name Surfacine® and the further classes of compounds listed in Appendix 6, Part A and B of the Cosmetics Regulation.
  • Natural fragrances are extracts of flowers (lily, lavender, roses, jasmine, neroli, ylang-ylang), stems and leaves (geranium, patchouli, petitgrain), fruits (aniseed, coriander, caraway, juniper), fruit peel (bergamot, lemon, Oranges), roots (macis, angelica, celery, cardamom, costus, iris, calmus), wood (pine, sandal, guaiac, cedar, rosewood), herbs and grasses (tarragon, lemongrass, sage, thyme), Needles and twigs (spruce, fir, pine, pines), resins and balsams (galbanum, elemi, benzoin, myrrh, olibanum, opoponax).
  • Typical synthetic fragrance compounds are ester type products, ethers, aldehydes, ketones, alcohols and hydrocarbons. Fragrance compounds of the ester type are, for example, benzyl acetate, phenoxyethyl isobutyrate, p-tert-butylcyclohexyl acetate, linalyl acetate, dimethylbenzylcarbinyl acetate, phenylethyl acetate, linalyl benzoate, benzyl formate, ethylmethylphenylglycinate, allylcyclohexylpropionate, styrallylpropionate and benzylsalicylate.
  • the ethers include, for example, benzyl ethyl ether, to the aldehydes, for example, the linear alkanals having 8 to 18 carbon atoms, citral, citronellal, Citronellellyloxyacetaldehyd, Cyclamenaldehyd, Hydroxycitronellal, Lilial and Bourgeonal, to the ketones such as the Jonone, ⁇ -lsomethylionon and Methylcedrylketon to the alcohol Anethole, citronellol, eugenol, isoeugenol, geraniol, linalool, phenylethylalcohol and terpineol; the hydrocarbons mainly include terpenes and balsams.
  • fragrance oils are also suitable as perfume oils, for example sage oil, chamomile oil, clove oil, lemon balm oil, mint oil, cinnamon oil, linden flower oil, juniper berry oil, vetiver oil, oliban oil, galbanum oil, labolanum oil and lavandin oil.
  • Suitable flavors are, for example, peppermint oil, spearmint oil, aniseed oil, star aniseed oil, caraway oil, eucalyptus oil, fennel oil, citron oil, wintergreen oil, clove oil, menthol and the like.
  • Dyes which may be used are those which are suitable and approved for cosmetic purposes. Examples are Kochillerot A (Cl.16255), Patent Blue V (C.1.42051), Indigotin (C.1.73015), Chlorophyllin (C.1.75810), Quinoline Yellow (CI47005), Titanium Dioxide (C.1.77891), Indanthrene Blue RS (Cl.69800 ) and madder paint (Cl.58000).
  • a luminescent dye and luminol may be included. These dyes are usually used in concentrations of 0.001 to 0.1 wt .-%, based on the total mixture. Examples
  • Stearic acid dimethylethanolamine ester is introduced into an autoclave suitable for quaternization and rinsed several times with nitrogen. It is heated to 90 ° C and methyl chloride is added in portions. After completion of the addition, the mixture is stirred at 90 0 C for four hours.
  • Comparative half-page tests were performed under standardized conditions on 10 female subjects to determine essential properties of shampoos.
  • composition used data as active substance content
  • the cationic surfactants were formulated in the following composition:
  • Table 2 shows impressively that the cationic surfactants Type 1 and Type 2 have the best properties and better conditioning properties than Behentrimonium Chloride.
  • Type 3 is at least comparable.
  • Example 3 Biodegradability and toxicity
  • the biodegradability and toxicity according to OECD 301 B was determined for algae. It was found that the product according to the invention is degraded rapidly and has a low toxicity of 50-100 mg / l against algae.
  • Behentrimonium chloride is not degraded and has a significantly higher toxicity of ⁇ 1 mg / l to algae.

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)
  • Dermatology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)
  • Detergent Compositions (AREA)

Abstract

L'invention porte sur des tensio-actifs cationiques de la formule (I), dans laquelle R1 représente un radical alkyle à 6 à 22 atomes de carbone, saturé ou insaturé, à chaîne droite ou ramifiée, R2 et R3 représentent chacun indépendamment de l'autre un radical alkyle ayant 1 à 3 atomes de carbone ou un atome d'hydrogène, n vaut 2 ou 3, et X désigne un halogène, un acide carboxylique déprotoné, ou un méthosulfate.
EP08801595A 2008-03-12 2008-08-16 Tensio-actifs cationiques présentant des propriétés améliorées Withdrawn EP2249778A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP08801595A EP2249778A1 (fr) 2008-03-12 2008-08-16 Tensio-actifs cationiques présentant des propriétés améliorées

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP08004512A EP2100587A1 (fr) 2008-03-12 2008-03-12 Agent tensioactif cationique doté de propriétés améliorées
PCT/EP2008/006751 WO2009112061A1 (fr) 2008-03-12 2008-08-16 Tensio-actifs cationiques présentant des propriétés améliorées
EP08801595A EP2249778A1 (fr) 2008-03-12 2008-08-16 Tensio-actifs cationiques présentant des propriétés améliorées

Publications (1)

Publication Number Publication Date
EP2249778A1 true EP2249778A1 (fr) 2010-11-17

Family

ID=39639535

Family Applications (2)

Application Number Title Priority Date Filing Date
EP08004512A Withdrawn EP2100587A1 (fr) 2008-03-12 2008-03-12 Agent tensioactif cationique doté de propriétés améliorées
EP08801595A Withdrawn EP2249778A1 (fr) 2008-03-12 2008-08-16 Tensio-actifs cationiques présentant des propriétés améliorées

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP08004512A Withdrawn EP2100587A1 (fr) 2008-03-12 2008-03-12 Agent tensioactif cationique doté de propriétés améliorées

Country Status (5)

Country Link
US (1) US20110014148A1 (fr)
EP (2) EP2100587A1 (fr)
JP (1) JP2011513444A (fr)
CN (1) CN101969919A (fr)
WO (1) WO2009112061A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3387217A4 (fr) * 2015-12-08 2019-07-31 Kemira Oyj Compositions polymères liquides
CN108927073B (zh) * 2018-07-04 2020-10-23 江南大学 一种腰果酚氨基酸表面活性剂及其制备方法
CN113481062A (zh) * 2021-07-08 2021-10-08 安徽启威生物科技有限公司 一种羽绒清洗蓬松剂及其制备方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS57109709A (en) * 1980-12-26 1982-07-08 Lion Corp Hair cosmetic
DE3440935A1 (de) * 1984-11-09 1986-05-15 Wella Ag, 6100 Darmstadt Haarkonditionierungsmittel mit perlglanz
JP2000128740A (ja) * 1998-10-23 2000-05-09 Kao Corp 毛髪化粧料
ITMI20042505A1 (it) * 2004-12-24 2005-03-24 Oro Consulting S R L Sostanza emulsionante e-o tensioattiva ad attivita' battericida per la preparazione di emulsioni e di tensidi per uso dermofarmaceutico e cosmetico emulsioni e tensidi preparati con questa sostanzaa prodotto dermofarmaceutico e prodotto cosmetico ott

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2009112061A1 *

Also Published As

Publication number Publication date
WO2009112061A1 (fr) 2009-09-17
CN101969919A (zh) 2011-02-09
JP2011513444A (ja) 2011-04-28
US20110014148A1 (en) 2011-01-20
EP2100587A1 (fr) 2009-09-16

Similar Documents

Publication Publication Date Title
EP2012741B1 (fr) Agents épaississants
EP1395643B1 (fr) Melanges d'agents tensioactifs
EP1434556A1 (fr) Preparations cosmetiques et / ou pharmaceutiques
EP1524029A1 (fr) Compositions auto-emuslifiantes
EP1254653B1 (fr) Utilisation de compositions cationiques
EP1286952B1 (fr) Melanges de composes quaternaires d'ester
EP1254655B1 (fr) Utilisation d'esters quaternaires
EP2366377B1 (fr) Composition de conditionnement et shampooing conditionnant comprenant un ester de pentaérythritol
DE10213019A1 (de) Verwendung von Extrakten des Olivenbaumes als Antischuppenmittel
EP1254654B1 (fr) Utilisation des compositions cationiques
WO2003032930A1 (fr) Shampooing conditionneur
EP2249778A1 (fr) Tensio-actifs cationiques présentant des propriétés améliorées
WO2004083351A1 (fr) Melanges d'agents tensioactifs
EP1264634B1 (fr) Utilisation d'alkyl(ether)phosphates
EP1374845A1 (fr) Préparations cosmétiques
WO2002087538A1 (fr) Utilisation de preparations cationiques
EP1374846A1 (fr) Compositions huileuses avec und viscosité élevée
DE10237031A1 (de) Quaternierte Fettsäurealkanolaminestersalze aur Basis konjugierter Linolsäure
DE10117501A1 (de) Mineralölhaltige Waschzubereitungen
EP1413285A1 (fr) Compositions d'apres-shampooing contenant des tensioactifs cationiques, des huiles et des alcohols d'acides gras
DE102005028763A1 (de) Haarbehandlungsmittel
WO2002038124A1 (fr) Utilisation de tensioactifs amphoteres
EP1064933A1 (fr) Proliposomes d'esters quaternaires
WO2003030843A2 (fr) Produits de soin capillaire

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20100805

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MT NL NO PL PT RO SE SI SK TR

AX Request for extension of the european patent

Extension state: AL BA MK RS

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20101130