WO1998019783A2 - Tensioactifs jumeles - Google Patents

Tensioactifs jumeles Download PDF

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Publication number
WO1998019783A2
WO1998019783A2 PCT/EP1997/005903 EP9705903W WO9819783A2 WO 1998019783 A2 WO1998019783 A2 WO 1998019783A2 EP 9705903 W EP9705903 W EP 9705903W WO 9819783 A2 WO9819783 A2 WO 9819783A2
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WO
WIPO (PCT)
Prior art keywords
alkyl
acid
surfactants
bisepoxides
alcohol
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PCT/EP1997/005903
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German (de)
English (en)
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WO1998019783A3 (fr
Inventor
Oliver Rhode
Hans-Christian Raths
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Henkel Kommanditgesellschaft Auf Aktien
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Publication of WO1998019783A2 publication Critical patent/WO1998019783A2/fr
Publication of WO1998019783A3 publication Critical patent/WO1998019783A3/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/56—Glucosides; Mucilage; Saponins
    • 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
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/604—Alkylpolyglycosides; Derivatives thereof, e.g. esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/42—Ethers, e.g. polyglycol ethers of alcohols or phenols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/662—Carbohydrates or derivatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/10—General cosmetic use

Definitions

  • the invention relates to new gemini surfactants based on sugar surfactants and bisepoxides. a process for their production and the use of the substances as wetting agents, O / W emulsifiers and thickeners.
  • gemini surfactants or bolate surfactants
  • spacer a nonpolar radical
  • the complex object of the invention was to provide surfactants with a high wetting capacity which at the same time have excellent emulsifying and thickening properties, are well tolerated by skin cosmetics and are also readily biodegradable.
  • the invention relates to gemini surfactants which are obtained by reacting alkyl and / or alkenyl oligoglycosides with bisepoxides.
  • the gemini surfactants according to the invention not only have excellent wetting power, but also favor the production of O / W emulsions and comparable problematic surfactants, such as, in particular, alkyl glucosides or fatty acid N-alkyl glucamides, reliably compared to comparable products of the prior art thicken.
  • comparable problematic surfactants such as, in particular, alkyl glucosides or fatty acid N-alkyl glucamides
  • the invention further relates to a process for the preparation of gemini surfactants, in which alkyl and / or alkenyl oligoglycosides are reacted with bisepoxides.
  • Alkyl and alkenyl oligoglycosides are known nonionic surfactants which follow the formula (I)
  • R 1 is an alkyl and / or alkenyl radical having 4 to 22 carbon atoms
  • G is a sugar radical having 5 or 6 carbon atoms
  • p is a number from 1 to 10.
  • the alkyl and / or 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 (I) indicates the degree of oligomerization (DP), i.e. H. the distribution of mono- and oligoglycosides is present and stands for a number between 1 and 10.
  • Alkyl and / or alkenyl oligoglycosides with an average degree of oligomerization p of 1.1 to 3.0 are preferably used. From an application point of view, preference is given to those alkyl and / or alkenyl oligoglycosides whose degree of oligomerization is less than 1.7 and in particular between 1.2 and 1.4.
  • 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, capro alcohol, caprylic alcohol, capric alcohol and undecyl alcohol and their technical mixtures, such as are obtained, for example, in the hydrogenation of technical fatty acid methyl esters or in the course of the hydrogenation of aldehydes from Roelen's oxosynthesis.
  • the alkyl or alkenyl radical R 1 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 their technical mixtures, as described above, which can be obtained as described above.
  • Alkyl oligoglucosides based on hardened C 12/14 coconut alcohol with a DP of 1 to are preferred Bisepoxides
  • n stands for 0 or numbers from 1 to 10.
  • Typical examples are 1,2,3,4-bisepoxybutane, 1,2,4,5-bisepoxypentane, 1,2,5,6-bisepoxyhexane, 1,2,7,8-bisepoxyoctane, 1,2,9,10- Bisepoxydecane, 1,2,11,12-bisepoxydodecane and 1,2,13,14-bisepoxytetradecane and their technical mixtures.
  • Bisepoxides of the glycidyl ether type can also be used, which are prepared by reacting diols with epichlorohydrin in a manner known per se.
  • Such bisepoxides of the glycidyl ether type follow the formula (III)
  • R 2 represents a divalent radical derived from diols.
  • the diols can be aliphatic diols with 3 to 12 carbon atoms, alkoxylated aliphatic diols with 3 to 12 carbon atoms and / or alkylene glycols.
  • Typical examples of aliphatic diols with 3 to 12 carbon atoms are 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol, 1,10 Decanediol, 1,11-undecanediol and 1,12-dodecanediol.
  • the alkoxylated aliphatic diols having 3 to 12 carbon atoms are ethoxylation and / or propoxylation products of the abovementioned aliphatic diols, the degree of ethoxylation and / or propoxylation being a statistical mean and preferably in the range from 1 to 10.
  • Typical examples are 1,4-butanediol + ethylene oxide (EO), 1,4-butanediol + IEO + propylene oxide (PO), 1,4-butanediol + 2EO + 2PO, 1,4-butanediol + 3EO + 2PO, 1,4 -Butanediol + lPO + lEO.
  • alkylene glycols are ethylene glycol and propylene glycol and their oligomers such as diethylene glycol, triethylene glycol and tetraethylene glycol.
  • the degree of oligomerization of the alkylene glycols is a statistical mean and is preferably in the range from 1 to 10.
  • the gemini surfactants can be prepared in the manner known for the ring opening of ole-fine epoxides from the prior art.
  • the alkyl and / or alkenyl oligoglycosides and the bispoxides are usually used in a molar ratio of 1.8 to 2.2: 1, i.e. the ratio of glucoside per epoxy group is approximately 1: 1.
  • the ring opening takes place at sufficiently high temperatures or under pressure even without the use of catalysts.
  • reaction is advantageously carried out in the presence of alkaline catalysts, since this allows lower reaction temperatures of 100 to 180 and preferably 150 to 170 ° C. It is also advisable to carry out the reaction under reduced pressure in order to implement the sugar surfactants which tend to caramelize under the mildest possible conditions. Gemini surfactants produced in this way are characterized by a higher color quality and are therefore preferred.
  • the gemini surfactants according to the invention have a high wetting power and an extremely low critical micelle concentration.
  • One object of the invention therefore relates to their use as wetting agents for the production of washing, rinsing and cleaning agents.
  • the gemini surfactants can be present in these preparations in amounts of 1 to 50, preferably 2 to 30% by weight, based on the composition.
  • the gemini surfactants also have excellent emulsifying and thickening properties. Accordingly, further objects of the invention relate to their use as O / W emulsifiers for the production of cosmetic and / or pharmaceutical preparations and as thickeners, in particular for alkyl and / or alkenyl oligoglycosides and fatty acid N-alkyl polyhydroxylkylamides.
  • the gemini surfactants can be present in these preparations in amounts of 1 to 50, preferably 2 to 30% by weight, based on the composition.
  • the gemini surfactants can be used together with further anionic, nonionic, cationic, amphoteric and / or zwitterionic surfactants.
  • anionic surfactants are soaps, alkyl benzene sulfonates, alkane sulfonates, olefin sulfonates, alkyl ether sulfonates, glycerol ether sulfonates, ⁇ -methyl ester sulfonates, sulfo fatty acids, alkyl sulfates, fatty alcohol ether sulfates, glycerol ether sulfates, hydroxymixed ether ether sulfates, ether sulfate (sulfate amate) sulfates, mono-sulfate ether sulfates, mono and dialkyl sulfosuccinates.
  • anionic surfactants contain polyglycol ether chains, they can 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 or mixed formals, alk (en) yl oligoglycosides.
  • Nonionic surfactants contain polyglycol ether chains, they can have a conventional, but preferably a narrow, homolog distribution.
  • Typical examples of cationic surfactants are quaternary ammonium compounds and ester quats, in particular quaternized fatty acid trialkanolamine ester salts.
  • Typical examples of amphoteric or zwitterionic surfactants are alkyl betaines, alkyl amido betaines, aminopropionates, aminoglycinates, imidazolinium betaines and sulfobetaines. The surfactants mentioned are exclusively known compounds.
  • gemini surfactants of the invention are preferably used together with mild, ie particularly skin-compatible surfactants, such as, for example, fatty alcohol polyglycol ether sulfates, monoglyceride sulfates, mono- and / or dialkyl sulfosuccinates, fatty acid isethionates, fatty acid sarcosinates, fatty acid taurides, fatty acid glutamates, ether carboglucosacids, ether carboxylic acids,
  • mild, ie particularly skin-compatible surfactants such as, for example, fatty alcohol polyglycol ether sulfates, monoglyceride sulfates, mono- and / or dialkyl sulfosuccinates, fatty acid isethionates, fatty acid sarcosinates, fatty acid taurides, fatty acid glutamates, ether carboglucosacids, ether carboxylic acids,
  • the gemini surfactants according to the invention can be used as wetting agents for the production of washing, rinsing and cleaning agents.
  • Typical examples of detergents, dishwashing detergents and cleaning agents are liquid to pasty fabric softeners, hand dishwashing detergents, machine dishwashing detergents, rinse aids as well as universal, household and sanitary cleaners as well as powdered or granulated universal detergents.
  • the agents can have further typical ingredients such as, for example, builders, enzymes, enzyme stabilizers, bleaches, optical brighteners, thickeners, soil repellants, foam inhibitors, solubilizers, inorganic salts and fragrances and colorants.
  • Suitable builders are zeolites, layered silicates, phosphates and ethylenediaminetetraacetic acid, nitrilotriacetic acid, citric acid and inorganic phosphonic acids.
  • bleaching agents are, for example, peroxy carbonate, citrate perhydrates and H 2 O 2 -supplying peracid salts of peracids such as per-benzoates, peroxyphthalates or diperoxydodecanedioic acid. They are usually used in amounts of 8 to 25% by weight.
  • the use of sodium perborate monohydrate in amounts of 10 to 20% by weight and in particular 10 to 15% by weight is preferred. Due to its ability to bind free water with the formation of the tetrahydrate, it contributes to increasing the stability of the agent.
  • hardened castor oil, salts of long-chain fatty acids preferably in amounts of 0 to 5% by weight and in particular in amounts of 0.5 to 2% by weight, for example sodium, potassium, aluminum, magnesium, can be used as thickeners - And titanium stearates or the sodium and / or potassium salts of behenic acid, and other polymeric compounds be used.
  • the latter preferably include polyvinylpyrrolidone, urethanes and the salts of polymeric polycarboxylates, for example homopolymeric or copolymeric polyacrylates, polymethacrylates and in particular copolymers of acrylic acid with maleic acid, preferably those composed of 50 to 10% maleic acid.
  • the relative molecular weight of the homopolymers is generally between 1000 and 100000, that of the copolymers between 2000 and 200000, preferably between 50,000 to 120,000, based on the free acid.
  • water-soluble polyacrylates are suitable that the sucrose are crosslinked, for example with about 1% of a polyallyl ether and which have a relative molecular mass above 1,000,000 own Examples of these are under the name Carbopol ® 940 and 941 available polymers.
  • the crosslinked polyacrylates are preferably used in amounts of not more than 1% by weight, particularly preferably in amounts of 0.2 to 0.7% by weight.
  • Enzymes come from the class of proteases, lipase, amylases. Cellulases or their mixtures in question. Enzymes obtained from bacterial strains or fungi such as Bacillus subtilis, Bacillus lichenformis and Strptomyces griseus are particularly suitable. Proteases of the subtilisin type and in particular proteases obtained from Bacillus lentes are preferably used. Their proportion can be about 0.2 to 2% by weight. The enzymes can be adsorbed on carriers or embedded in coating substances to protect them against premature decomposition.
  • the agents can contain further enzyme stabilizers.
  • enzyme stabilizers For example, 0.5 to 1% by weight sodium formate can be used. It is also possible to use proteases which are stabilized with soluble calcium salts and a calcium content of preferably about 1.2% by weight, based on the enzyme.
  • boron compounds for example boric acid, boron oxide, borax and other alkali metal borates such as the salts of orthoboric acid (H 3 BO 3 ), metaboric acid (HBO 2 ) and pyrobic acid (tetraboric acid H 2 B 4 O 7 ), is particularly advantageous.
  • Suitable foam inhibitors contain, for example, known organopolysiloxanes, paraffins or waxes.
  • the gemini surfactants according to the invention can be used as O / W emulsifiers for the production of cosmetic and / or pharmaceutical preparations.
  • the cosmetic and / or pharmaceutical preparations for example hair shampoos, hair lotions, foam baths, creams, lotions or ointments, can furthermore contain, as further auxiliaries and additives, oil bodies, co-emulsifiers, superfatting agents, stabilizers, waxes, consistency agents, thickeners, cation polymers, silicone compounds , biogenic agents, antidandruff agents, film formers, preservatives, hydrotropes, solubilizers, UV light protection filters, insect repellents, self-tanners, dyes and fragrances.
  • Guerbet alcohols based on fatty alcohols having 6 to 18, preferably 8 to 10, carbon atoms, esters of linear C 6 -C 22 fatty acids with linear C 6 -C 22 fatty alcohols, esters of branched C 6 -C 13 carboxylic acids are examples of oil bodies with linear C 6 -C 22 fatty alcohols, esters of linear C 6 -C 22 fatty acids with branched alcohols, in particular 2-ethylhexanol, esters of linear and / or branched fatty acids with polyhydric alcohols (such as propylene glycol, dimer diol or trimer triol) and / or Guerbet alcohols, triglycerides based on C 6 -C 10 fatty acids, esters of C 6 -C 22 fatty alcohols and / or Guerbet alcohols with aromatic carboxylic acids, especially benzoic acid, vegetable oils, branched primary alcohols, substituted cyclohexanes, linear C 6 -C 22
  • suitable co-emulsifiers are nonionic surfactants from at least one of the following groups:
  • polystyrene resin e.g. Polyglycerol polyricinoleate or polyglycerol poly-12-hydroxystearate. Mixtures of compounds from several of these classes of substances are also suitable;
  • partial esters based on linear, branched, unsaturated or saturated C 6/22 fatty acids, ricinoleic acid and 12-hydroxystearic acid and glycerin, polyglycerin, pentaerythritol, dipentaerythritol, sugar alcohols (e.g. sorbitol), alkyl glucosides (e.g. methyl glucoside, butyl glucoside Lauryl glucoside) and polyglucosides (eg cellulose);
  • the adducts of ethylene oxide and / or of propylene oxide with fatty alcohols, fatty acids, alkylphenols, glycerol mono- and diesters as well as sorbitan mono- and diesters of fatty acids or with castor oil are known, commercially available products. These are mixtures of homologs, whose average degree of alkoxylation corresponds to the ratio of the amounts of ethylene oxide and / or propylene oxide and substrate with which the addition reaction is carried out.
  • C 12/18 fatty acid monoesters and diesters of adducts of ethylene oxide with glycerol are known from DE-PS 20 24 051 as refatting agents for cosmetic preparations.
  • Cg / , 8 - alkyl mono- and oligoglycosides their preparation and their use as surface-active substances are, for example, from US 3,839,318, US 3,707,535, US 3,547,828, DE-OS 19 43 689, DE-OS 20 36 472 and DE-Al 30 01 064 and EP-A 0 077 167 are known. They are produced in particular by reacting glucose or oligosaccharides with primary alcohols with 8 to 18 carbon atoms.
  • both Monoglycosides in which a cyclic sugar residue is glycosidically bound to the fatty alcohol, and also oligomeric glycosides with a degree of oligomerization of up to preferably about 8 are suitable.
  • the degree of oligomerization is a statistical mean value which is based on a homolog distribution customary for such technical products.
  • Zwitterionic surfactants can also be used as emulsifiers.
  • Zwitterionic surfactants are surface-active compounds that contain at least one quaternary ammonium group and at least one carboxylate and one sulfonate group in the molecule.
  • Particularly suitable zwitterionic surfactants are the so-called betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example coconut alkyldimethylammonium glycinate, N-acylamino-propyl-N, N-dimethylammonium glycinate, for example the cocosacy laminopropyldimethylammonium glycinate, and 2- Alkyl-3-carboxylmethyl 1-3 -hydroxyethylimidazolines, each with 8 to 18 carbon atoms in the alkyl or acyl group, and the cocosacylaminoethylhydroxyethylcarboxymethylglycinate.
  • betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example coconut alkyldimethylammonium glycinate, N-acylamino-propyl-N, N-dimethylammonium
  • Suitable emulsifiers are ampholytic surfactants.
  • Ampholytic surfactants are surface-active compounds which, in addition to a C8 / I8 alkyl or acyl group in the molecule at least one free amino group and at least one -COOH or -SO3H group and are capable of forming inner salts.
  • ampholytic surfactants are N-alkylglycine, N-alkylpropionic acid, N-alkylaminobutyric acid, N-alkylimino dipropionic acid, N-hydroxyethyl-N-alkylamidopropylglycine, N-alkyltaurine, N-alkyl sarcosine, 2-alkylaminopropionic acid and alkylamino acetic acid, each with approximately 8 to 18 carbon atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-coconut alkylaminopropionate, coconut acylaminoethylaminopropionate and C 12/18 acyl sarcosine.
  • quaternary emulsifiers are also suitable, those of the esterquat type, preferably methyl-quaternized difatty acid triethanolamine ester salts, being particularly preferred.
  • Substances such as, for example, lanolin and lecithin and polyethoxylated or acylated lanolin and lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides can be used as superfatting agents, the latter simultaneously serving as foam stabilizers.
  • Mainly fatty alcohols with 12 to 22 and preferably 16 to 18 carbon atoms and also partial glycerides come into consideration as consistency agents.
  • a combination of these substances with alkyl oligoglucosides and / or fatty acid N-methylglucamides of the same chain length and / or polyglycerol poly-12- is preferred.
  • Suitable thickeners are, for example, polysaccharides, in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, and also higher molecular weight polyethylene glycol mono- and di-esters of fatty acids, polyacrylates (e.g.
  • surfactants such as ethoxylated fatty acid glycerides, esters of fatty acids with polyols such as pentaerythritol or trimethylolpropane, fatty alcohol ethoxylates with a narrow homolog distribution or alkyl oligoglucosides as well as electrolytes such as sodium chloride and ammonium chloride.
  • Suitable cationic polymers are, for example, cationic cellulose derivatives, e.g. a quaternized hydroxyethyl cellulose available under the name Polymer JR 400® from Amerchol, cationic starch, copolymers of diallyl ammonium salts and acrylamides, quaternized vinyl pyrrolidone / vinyl imidazole polymers such as e.g.
  • Luviquat® condensation products of poly-glycols and amines, quaternized collagen polypeptides such as lauryldimonium hydroxypropyl hydrolyzed collagen (Lamequat®L / Grünau), quaternized wheat polypeptides, polyethyleneimine, cationic silicone polymers such as e.g. Amidomethicone, copolymers of adipic acid and dimethylaminohydroxypropyldiethylenetrimamine (Carretine® / Sandoz), copolymers of acrylic acid with dimethyldiallylammonium chloride (Merquat® 550 / Chemviron), polyaminopolyamides such as e.g.
  • cationic chitin derivatives such as quaternized chitosan, optionally microcrystalline, condensation products of dihaloalkylene such as e.g. Dibromobutane with bisdialkylamines such as Bis-dimethylamino-1,3-propane, cationic guar gum such as e.g. Jaguar® CBS, Jaguar® C-17, Jaguar® C-16 from Celanese, quaternized ammonium salt polymers such as Mirapol® A-15, Mirapol® AD-1, Mirapol® AZ-1 from Miranol.
  • dihaloalkylene such as e.g. Dibromobutane
  • bisdialkylamines such as Bis-dimethylamino-1,3-propane
  • cationic guar gum such as e.g. Jaguar® CBS, Jaguar® C-17, Jaguar® C-16 from Celanese
  • quaternized ammonium salt polymers such as Mirapol® A-15, Mirapol® AD-1, Mir
  • Suitable silicone compounds are, for example, dimethylpolysiloxanes, methylphenylpolysiloxanes, cyclic silicones and amino-, fatty acid-, alcohol-, polyether-, epoxy-, fluorine- and / or alkyl-modified silicone compounds which can be both liquid and resinous at room temperature.
  • Typical examples of fats are glycerides, waxes include beeswax, carnauba wax, candelilla wax, montan wax, paraffin wax or micro waxes, if appropriate in combination with hydrophilic waxes, for example cetyl stearyl alcohol or partial glycerides.
  • Pearlescent waxes which can in particular be mono- and difatty acid esters of polyalkylene glycols, partial glycerides or esters of Fatty alcohols with polyvalent carboxylic acids or hydroxycarboxylic acids can be used.
  • Metal salts of fatty acids such as magnesium, aluminum and / or zinc stearate can be used as stabilizers.
  • Biogenic active substances are to be understood to mean, for example, tocopherol, tocopherol acetate, tocopherol palmitate, ascorbic acid, retinol, bisabolol, allantoin, phytantriol, panthenol, AHA acids, plant extracts and vitamin complexes.
  • Climbazole, octopirox and zinc pyrethione can be used as antidandruff agents.
  • Common 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 its salts and similar compounds.
  • UV light protection filters are understood to mean organic substances which are able to absorb ultra-violet rays and which absorb energy in the form of longer-wave radiation, e.g. To give off heat again.
  • Typical examples are 4-aminobenzoic acid and its esters and derivatives (e.g. 2-ethylhexyl-p-dimethylaminobenzoate or p-dimethylaminobenzoic acid octyl ester), methoxycinnamic acid and its derivatives (e.g. 4-methoxycinnamic acid-2-ethylhexyl ester), benzophenones (e.g.
  • the particles should have an average diameter of less than 100 nm, preferably between 5 and 50 nm and in particular between 15 and 30 nm. They can have a spherical shape, but it is also possible to use particles which have an ellipsoidal shape or shape which differs from the spherical shape in some other way.
  • secondary light stabilizers of the antioxidant type can also be used, which interrupt the photochemical reaction chain which is triggered when UV radiation penetrates the skin. Typical examples are superoxide dismutase, tocopherols (vitamin E) and ascorbic acid (vitamin C).
  • Hydrotropes such as ethanol, isopropyl alcohol or polyols can also be used to improve the flow behavior.
  • Polyols that come into consideration here preferably have 2 to 15 carbon atoms and at least two hydroxyl groups. Typical examples are
  • Alkylene glycols such as, for example, ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol and polyethylene glycols with an average molecular weight of 100 to 1,000 daltons;
  • Methyl compounds such as in particular trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol and dipentaerythritol;
  • Lower alkyl glucosides especially those with 1 to 8 carbons in the alkyl radical, such as methyl and butyl glucoside;
  • Sugar alcohols having 5 to 12 carbon atoms such as, for example, sorbitol or mannitol,
  • Aminosugars such as glucamine.
  • Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, para-bene, pentanediol or sorbic acid.
  • N, N-diethyl-m-touluamide, 1, 2-pentanediol or Insect repellent 3535 are suitable as insect repellents, and dihydroxyacetone is suitable as a self-tanner.
  • the dyes which can be used are those substances which are suitable and approved for cosmetic purposes, as compiled, for example, in the publication "Cosmetic Dyes" by the Dye Commission of the German Research Foundation, Verlag Chemie, Weinheim, 1984, pp. 81-106. These dyes are usually used in concentrations of 0.001 to 0.1% by weight, based on the mixture as a whole.
  • the total proportion of auxiliaries and additives can be 1 to 50, preferably 5 to 40,% by weight, based on the composition.
  • the agents can be produced by customary cold or hot processes; the phase inversion temperature method is preferably used. Examples
  • Example 1 was repeated, but 43 g (0.5 mol) of 1,2,3,4-diepoxybutane were used instead of the glycidyl ether.
  • the reaction product was also obtained as a yellow, slightly water-soluble solid.

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Abstract

L'invention concerne de nouveaux tensioactifs jumelés obtenus par condensation d'oligoglycosides d'alkyle et/ou d'alkylène avec des bis-époxydes. Ces substances s'utilisent comme agents mouillants, émulsifiants huile dans l'eau, ainsi que comme épaississants pour des glucosides d'alkyle.
PCT/EP1997/005903 1996-11-02 1997-10-25 Tensioactifs jumeles WO1998019783A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19645189A DE19645189A1 (de) 1996-11-02 1996-11-02 Geminitenside
DE19645189.2 1996-11-02

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WO1998019783A2 true WO1998019783A2 (fr) 1998-05-14
WO1998019783A3 WO1998019783A3 (fr) 1998-08-20

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DE (1) DE19645189A1 (fr)
WO (1) WO1998019783A2 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6183550B1 (en) 1998-04-22 2001-02-06 Hercules Incorporated Paper size dispersions
CN102503863A (zh) * 2011-10-10 2012-06-20 西南石油大学 一种双烷基醚双磺酸盐表面活性剂及其制备方法
CN102861532A (zh) * 2012-09-21 2013-01-09 浙江大学 一种十八醇葡萄糖双子表面活性剂及其制备方法
CN102875613A (zh) * 2012-09-21 2013-01-16 浙江大学 一种十六醇葡萄糖双子表面活性剂及其制备方法
CN102895915A (zh) * 2012-09-21 2013-01-30 浙江大学 一种十四醇葡萄糖双子表面活性剂及其制备方法
CN102895914A (zh) * 2012-09-21 2013-01-30 浙江大学 一种十二醇葡萄糖双子表面活性剂及其制备方法

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19943681A1 (de) * 1999-09-13 2001-03-15 Rwe Dea Ag Tensidzusammensetzung enthaltend Geminitenside und deren Verwendung zur Haut- und Haarreinigung
CN102872752B (zh) * 2012-09-21 2014-04-16 浙江大学 一种癸醇葡萄糖双子表面活性剂及其制备方法

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DE1206877B (de) * 1963-03-12 1965-12-16 Richard Huttenlocher Dr Ing Verfahren zur Herstellung von grenzflaechenaktiven, biologisch abbaufaehigen AEthern von Zuckern oder mehrwertigen aliphatischen Alkoholen
US4011389A (en) * 1975-03-21 1977-03-08 Basf Wyandotte Corporation Glycoside polyethers
EP0442371A2 (fr) * 1990-02-16 1991-08-21 BASF Aktiengesellschaft Bisglycosides

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FR2683223B1 (fr) * 1991-11-05 1995-04-28 Stepan Europe Composes amphiphiles, a double tete sucre agent tensioactif et agent vesiculaire comprenant un tel compose et procede de preparation dudit compose.

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1206877B (de) * 1963-03-12 1965-12-16 Richard Huttenlocher Dr Ing Verfahren zur Herstellung von grenzflaechenaktiven, biologisch abbaufaehigen AEthern von Zuckern oder mehrwertigen aliphatischen Alkoholen
US4011389A (en) * 1975-03-21 1977-03-08 Basf Wyandotte Corporation Glycoside polyethers
EP0442371A2 (fr) * 1990-02-16 1991-08-21 BASF Aktiengesellschaft Bisglycosides

Non-Patent Citations (2)

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Title
P. GOUÉTH ET AL: CARBOHYDRATE RESEARCH , Nr. 266, 1995, Seiten 171-189, XP004022191 in der Anmeldung erwähnt *
Y. SUMIDA ET AL: LANGMUIR, Bd. 12, Nr. 16, 1996, Seiten 3986-3990, XP002057421 *

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6183550B1 (en) 1998-04-22 2001-02-06 Hercules Incorporated Paper size dispersions
CN102503863A (zh) * 2011-10-10 2012-06-20 西南石油大学 一种双烷基醚双磺酸盐表面活性剂及其制备方法
CN102861532A (zh) * 2012-09-21 2013-01-09 浙江大学 一种十八醇葡萄糖双子表面活性剂及其制备方法
CN102875613A (zh) * 2012-09-21 2013-01-16 浙江大学 一种十六醇葡萄糖双子表面活性剂及其制备方法
CN102895915A (zh) * 2012-09-21 2013-01-30 浙江大学 一种十四醇葡萄糖双子表面活性剂及其制备方法
CN102895914A (zh) * 2012-09-21 2013-01-30 浙江大学 一种十二醇葡萄糖双子表面活性剂及其制备方法
CN102895914B (zh) * 2012-09-21 2014-03-12 浙江大学 一种十二醇葡萄糖双子表面活性剂及其制备方法
CN102895915B (zh) * 2012-09-21 2014-03-12 浙江大学 一种十四醇葡萄糖双子表面活性剂及其制备方法
CN102875613B (zh) * 2012-09-21 2014-04-16 浙江大学 一种十六醇葡萄糖双子表面活性剂及其制备方法

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WO1998019783A3 (fr) 1998-08-20
DE19645189A1 (de) 1998-05-07

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