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WO1999006518A1 - Solutions tensio-actives aqueuses epaissies - Google Patents

Solutions tensio-actives aqueuses epaissies Download PDF

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Publication number
WO1999006518A1
WO1999006518A1 PCT/EP1998/004605 EP9804605W WO9906518A1 WO 1999006518 A1 WO1999006518 A1 WO 1999006518A1 EP 9804605 W EP9804605 W EP 9804605W WO 9906518 A1 WO9906518 A1 WO 9906518A1
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WO
WIPO (PCT)
Prior art keywords
acid
formula
fatty acid
fatty
surfactant solutions
Prior art date
Application number
PCT/EP1998/004605
Other languages
German (de)
English (en)
Inventor
Hans-Christian Raths
Norman Milstein
Werner Seipel
Original Assignee
Cognis Deutschland 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
Priority claimed from DE19736906A external-priority patent/DE19736906A1/de
Application filed by Cognis Deutschland Gmbh filed Critical Cognis Deutschland Gmbh
Priority to AU88076/98A priority Critical patent/AU8807698A/en
Publication of WO1999006518A1 publication Critical patent/WO1999006518A1/fr

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Classifications

    • 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
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0008—Detergent materials or soaps characterised by their shape or physical properties aqueous liquid non soap compositions
    • C11D17/003—Colloidal solutions, e.g. gels; Thixotropic solutions or pastes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/24—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran
    • C07C67/26—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran with an oxirane ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
    • C08G65/2615—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen the other compounds containing carboxylic acid, ester or anhydride groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
    • C08G65/2669—Non-metals or compounds thereof
    • C08G65/2672—Nitrogen or compounds thereof
    • 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
    • C11D1/74—Carboxylates or sulfonates esters of polyoxyalkylene glycols
    • 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
    • C11D1/825—Mixtures of compounds all of which are non-ionic

Definitions

  • the invention relates to aqueous surfactant solutions which contain fatty acid alkylene glycols as thickeners, the use of fatty acid alkylene glycols as thickeners in aqueous surfactant solutions and processes for the production of fatty acid propylene glycols and for the production of fatty acid ethylene propylene glycols.
  • Aqueous surfactant solutions in particular those which are used in the field of personal care as hair shampoos, bubble baths, shower baths, hand wash pastes and the like, usually contain anionic surfactants, such as, for example, alkyl ether sulfates.
  • anionic surfactants such as, for example, alkyl ether sulfates.
  • thickeners are usually added to these surfactant solutions.
  • inorganic and organic compounds which are used to increase the viscosity of solutions containing anionic surfactants are already known to the person skilled in the art.
  • Water-soluble electrolyte salts usually table salt, are generally used as inorganic thickeners.
  • organic thickeners are fatty acid alkanolamides, polyethylene glycol difatty acid esters and a number of water-soluble polymers.
  • organic thickeners In most cases it is at most possible to use large amounts to adjust the desired viscosity of the surfactant solution simply by using inorganic electrolyte salts. It is therefore generally the way to use organic thickeners in addition to the inorganic salts, but some of them have a number of disadvantages.
  • the surfactant solutions thickened with polyethylene glycol fatty acid diester often have inadequate viscosity stability during storage, while water-soluble polymers have an undesirable slimy flow behavior with a tendency to string in the thickened surfactant solutions.
  • the present invention therefore relates to thickened aqueous surfactant solutions which are characterized in that they are fatty acid alkylene glycols of the formula (I) as organic thickeners,
  • R 1 CO represents a linear or branched, aliphatic, saturated and / or unsaturated acyl radical having 6 to 22 carbon atoms
  • Alk represents CH2CH2, CHCH3CH2 and / or CH2CHCH3 and n represents numbers from 0.5 to 5.
  • thickened is to be understood such that the thickened surfactant solutions have at least one viscosity which is at least 5 times, preferably 10 times, higher than the non-thickened surfactant solutions.
  • thickened surfactant solutions have at least one viscosity which is at least 5 times, preferably 10 times, higher than the non-thickened surfactant solutions.
  • thickened surfactant solutions have at least one viscosity which is at least 5 times, preferably 10 times, higher than the non-thickened surfactant solutions.
  • thickened surfactant solutions have at least one viscosity which is at least 5 times, preferably 10 times, higher than the non-thickened surfactant solutions.
  • thickened surfactant solutions have at least one viscosity which is at least 5 times, preferably 10 times, higher than the non-thickened surfactant solutions.
  • thickened surfactant solutions have at least one viscosity which is at least 5 times, preferably 10 times, higher than the non-thickened surfactant solutions.
  • the fatty acid alkylene glycols are addition products of ethylene oxide or of ethylene oxide and propylene oxide onto fatty acids of the formula R COOH, in which R 1 CO is as defined above.
  • Typical examples are caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, elaeostearic acid, arachidic acid, gadoleic acid, behenic acid and erucic acid, and technical mixtures which are obtained, for example, in the pressure splitting of natural fats and oils, in the reduction of aldehydes from Roelen's oxosynthesis or as a monomer fraction in the dimerization of unsaturated fatty acids.
  • fatty acids with 12 to 18 carbon atoms such as coconut, palm, palm kernel or tallow fatty acids
  • Particularly preferred are ethoxylated or ethoxylated and propoxylated fatty acids which have n numbers between 1 and 2 as the degree of alkoxylation. It can it is exclusively propoxylated or ethoxylated and propoxylated fatty acids, and the mixed alkoxylated can be either random or block compounds.
  • ethoxylated and / or propoxylated fatty acids which are also referred to as fatty acid alkylene glycols
  • fatty acid alkylene glycols are known compounds. They can be prepared, for example, in accordance with German Offenlegungsschrift DE-A-2024050 by reacting carboxylic acids with alkylene oxides in the presence of armines as catalysts. According to this process, however, the low alkoxylated compounds are obtained in yields well below 90% of theory. According to this process, the ethoxylation is carried out in the presence of alkanolamines as catalyst and gives significantly higher yields.
  • R 1 CO is as defined in formula (I)
  • PO stands for CHCH3CH2 and / or CH2CHCH3 and n stands for numbers from 0.5 to 5 and fatty acid ethylene propylene glycols of the formula (III),
  • R 1 CO is as defined in formula (I)
  • EO is CH2CH2
  • PO is CHCH3CH2 and / or CH2CHCH3
  • x 0-5
  • y 0.1-5
  • z 0
  • the sum of x and z is greater than 0 and the sum of x, y and z is in the range from 0.5 to 5, by propoxylation or propoxylation / ethoxylation of fatty acids, which is characterized in that the propoxylation or ethoxylation / propoxylation reaction in the presence of alkanolamines as catalysts.
  • alkanolamines which can be used as basic catalysts are monoethanolamine, diethanolamine and preferably triethanolamine.
  • the alkanolamines are usually used in amounts of 0.1 to 5, preferably 0.5 to 3.0,% by weight, based on the fatty acids.
  • the propoxylation and / or ethoxylation propoxylation reaction can be carried out in a manner known per se be performed.
  • the fatty acid and the catalyst are usually placed in a stirred autoclave, which is freed of traces of water by alternating evacuation and nitrogen flushing before the reaction.
  • the fatty acid is then reacted with the propylene oxide or with the ethylene oxide / propylene oxide mixture in a molar ratio of 1: 0.5 to 1: 1.5, which can be metered into portions of the pressure vessel after heating by means of a siphon.
  • the fatty acids are preferably reacted with one mole to 2 moles of propylene oxide or with one to 2 moles of the ethylene oxide / propylene oxide mixture.
  • the reaction can be carried out at temperatures in the range from 80 to 180 ° C., preferably 100 to 120 ° C. and autogenous pressures in the range from 1 to 5, preferably 2 to 3 bar. After the end of the reaction, it is advisable to stir at the reaction temperature for a certain time to complete the conversion (15 to 90 min).
  • the autoclave is then cooled, decompressed and, if desired, acids such as lactic acid or phosphoric acid are added to the product in order to neutralize the basic catalyst.
  • the fatty acid alkylene glycols of the type described are usually present in the thickened aqueous surfactant solutions according to the invention in amounts of 0.2 to 5% by weight, based on the surfactant solution.
  • the surfactant solutions also contain 3 to 30% by weight of ionic surfactants and optionally up to 10% by weight of water-soluble inorganic and / or organic electrolyte salts. The rest of 100% by weight of the surfactant solution is water.
  • Anionic, zwitterionic and cationic surfactants can be present as ionic surfactants.
  • Suitable ionic surfactants are distinguished by a lipophilic, preferably linear alkyl or alkylene group having 8 to 18 carbon atoms and a ionic group, preferably terminally bonded to it, dissociating in water.
  • the anionic group can be, for example, a sulfate, sulfonate, phosphate or carboxylate group
  • the cationic group can be, for example, a quaternary ammonium group.
  • anionic surfactants are soaps, alkyl benzene sulfonates, alkane sulfonates, olefin sulfonates, alkyl ether sulfonates, glycerol ether sulfonates, ⁇ -methyl ester sulfonates,
  • Sulfofatty acids alkyl sulfates, fatty alcohol ether sulfates, Glycerol ether, Hydroxymischethersulfate, monoglyceride (ether) sulfates, fatty acid amide (ether) sulfates, mono- and dialkyl sulfosuccinates, mono- and dialkyl sulfosuccinamates, sulfotriglycerides, amide soaps, ether carboxylic acids and salts thereof, fatty acid isethionates, fatty acid sarcosinates, fatty acid taurides, N Acylamino acids, such as acyl lactylates, acyl tartrates, acyl glutamates and acyl aspartates, alkyl oligoglucoside sulfates, protein fatty acid condensates (especially vegetable products based on wheat) and alkyl (ether) phosphates.
  • anionic 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, especially quaternized fatty acids retrialkanolamine 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.
  • Suitable inorganic electrolyte salts are all water-soluble alkali, ammonium and / or alkaline earth metal salts such as fluorides, chlorides, bromides, sulfates, phosphates and nitrates, provided that they are soluble in water at 20 ° C in an amount of at least 1% by weight.
  • the chlorides or sulfates of an alkali metal, ammonium or magnesium are preferably used.
  • Sodium chloride (table salt) and magnesium chloride are particularly preferred.
  • All water-soluble alkali, ammonium and alkaline earth salts of mono-, di- and tricarboxylic acids are particularly suitable as organic electrolyte salts. Preference is given to carboxylic acids which have a molar mass of less than 200 g / mol.
  • the increase in viscosity of aqueous solutions of the type described with a comparatively low content of organic thickeners and of inorganic thickening electrolyte salts is of particularly high technical interest.
  • the thickening effect of the inorganic electrolyte salts is increased in a synergistic manner, so that the amount of inorganic electrolyte salts used can be reduced for a given viscosity setting.
  • Another object of the present invention therefore relates to the use of the fatty acid alkylene glycols of the formula (I) as organic thickeners for aqueous surfactant solutions.
  • the thickened surfactant solutions of the invention can furthermore contain oil bodies, emulsifiers, superfatting agents, pearlescent waxes, stabilizers, consistency enhancers, thickening agents, polymers, silicone compounds, biogenic active substances, antidandruff agents as further auxiliaries and additives
  • Film maker Preservatives, hydrotropes, solubilizers, UV light protection filters, insect repellents, self-tanners, perfume oils, dyes and the like contain.
  • Suitable emulsifiers are nonionic surfactants from at least one of the following groups:
  • alkyl mono- and oligoglycosides with 8 to 22 carbon atoms in the alkyl radical and their ethoxylated analogs
  • polyol and especially polyglycerol esters such as e.g. Polyglycerol polyricinoleate, polyglycerol poly-12-hydroxystearate or polyglycerol dimerate. Mixtures of compounds from several of these classes of substances are also suitable;
  • partial esters based on linear, branched, unsaturated or saturated C6 / 22 fatty acids, ricinoleic acid as well as 12-hydroxystearic acid and glycerin, polyglycerin, pentaerythritol, dipenta- erythritol, sugar alcohols (eg sorbitol), alkyl glucosides (eg 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 and sorbitan mono- and diesters of fatty acids or with castor oil are known, commercially available products. These are mixtures of homologs, the middle of which 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.
  • Ci2 / i8 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.
  • C & 7i8 alkyl mono- and oligoglycosides their preparation and their use are known from the prior art. They are produced in particular by reacting glucose or oligosaccharides with primary alcohols with 8 to 18 carbon atoms.
  • glycoside residue both monoglycosides in which a cyclic sugar residue is glycosidically bonded to the fatty alcohol and oligomeric glycosides with a degree of oligomerization of up to 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 coconut acylaminopropyldimethylammonium glycinate, and 2-alkyl-3-carboxyl -3-hydroxyethylimidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group and the cocoacylaminoethylhydroxyethylcarboxymethylglycinate.
  • betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example coconut alkyldimethylammonium glycinate, N-acylamino propyl-N, N-dimethylammonium glycinate, for
  • fatty acid amide derivative known under the CTFA name Cocamidopropyl Betaine is particularly preferred.
  • Suitable emulsifiers are ampholytic surfactants.
  • Ampholytic surfactants are surface-active compounds which, in addition to a Cs / i ⁇ -alkyl or -acyl group, have at least one free amino group in the molecule and at least one -COOH- or -SO3H- Contain group and are able to form internal salts.
  • ampholytic surfactants are N-alkylglycine, N-alkylpropionic acid, N-alkylaminobutyric acid, N-alkyliminodipropionic acid, N-hydroxyethyl-N-alkylamidopropylglycine, N-alkyltaurine, N-alkylsarcosine, 2-alkylaminopropionic acid and alkylaminoacetic acid each have about 8 to 18 carbon atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and Ci2 / ⁇ -acylsarcosine.
  • 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.
  • Pearlescent waxes are: alkylene glycol esters, especially ethylene glycol distearate; Fatty acid alkanolamides, especially coconut fatty acid diethanolamide; Partial glycerides, especially stearic acid monoglyceride; Esters of polyvalent, 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, for example, fatty alcohols, fatty ketones, fatty aldehydes, fatty ethers and fatty carbonates, which have a total of 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 with 12 to 22 carbon atoms with fatty alcohols with 12 to 22 carbon atoms and / or polyols with 2 to 15 carbon atoms
  • 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 diesters of fatty acids, polyacrylates (eg Carbopole® from Goodrich or Synthalene® from Sigma), polyacrylic amides, polyvinyl alcohol and polyvinyl pyrrolidone, surfactants such as ethoxylated fatty acid glycerides, esters of fatty acids with polyols such as pentaerythritol or trimethylol propane, fatty alcohol ethoxylates with a narrow homolog distribution or alkyl oligoglucosides as well as electrolytes such as sodium chloride and ammonium chloride.
  • polysaccharides in particular xanthan gum, guar guar, agar agar
  • Suitable cationic polymers are, for example, cationic cellulose derivatives, such as, for example, a quaternized hydroxyethyl cellulose, which is obtained from Amerchol under the name Polymer JR 400®. is, cationic starch, copolymers of diallylammonium salts and acrylamides, quaternized vinyl pyrrolidone / vinyl imidazole polymers, such as Luviquat® (BASF), condensation products of polyglycols and amines, quaternized colagen polypeptides such as lauryldimonium hydroxypropyl hydrolyzed collagen ( ®L / Grünau), quaternized wheat polypeptides, polyethyleneimine, cationic silicone polymers, such as amidomethicones, copolymers of adipic acid and dimethylaminohydroxypropyldiethylenetriamine (Cartaretine® / Sandoz), copolymers of acrylic acid with dimethyldiallylammonium chlor
  • Anionic, zwitterionic, amphoteric and nonionic polymers include, for example, vinyl acetate / crotonic acid copolymers, vinylpyrrolidone / vinyl acrylate copolymers, vinyl acetate / butyl maleateV isobomylacrylate copolymers, methyl vinyl ether / maleic anhydride copolymers and their esters, polyols, acrylamide and non-crosslinked acrylamide and acrylamide vinyl chloride Acrylate copolymers, octylacrylamide / methyl methacrylate / tert-butylaminoethyl methacrylate / 2-hydroxypropyl methacrylate copolymers, polyvinylpyrrolidone, vinylpyrrolidone / vinyl acetate copolymers, vinylpyrrolidone / dimethylaminoethyl methacrylate / vinylcaprolactam terpolymer and optionally derivatized
  • 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 can be both liquid and resinous at room temperature.
  • Typical examples of fats are glycerides, beeswax, camamauba wax, candelilla wax, montan wax, paraffin wax or microwaxes, if appropriate in combination with hydrophilic waxes, for example cetylstearyl alcohol or partial glycerides.
  • Metal salts of fatty acids such as magnesium, aluminum and / or zinc stearate can be used as stabilizers.
  • Biogenic active substances are, for example, tocopherol, tocopherol acetate, tocopherol palmitate, ascorbic acid, deoxyribonucleic acid, retinol, bisabolol, allantoin, phytantriol, panthenol, AHA acids, amino acids, ceramides, pseudoceramides, essential oils, plant extracts and vitamins.
  • 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 their salts and similar compounds.
  • Montmorillonites, clay minerals, pemulene and alkyl-modified carbopol types can serve as swelling agents for aqueous phases.
  • UV light protection filters are organic substances which are able to absorb ultraviolet rays and the absorbed energy in the form of longer-wave radiation, e.g. To give off heat again.
  • UVB filters can be oil-soluble or water-soluble. As oil-soluble substances e.g. to call:
  • 4-aminobenzoic acid derivatives preferably 2-ethylhexyl 4- (dimethylamino) benzoate, 2-octyl 4- (dimethylamino) benzoate and amyl 4- (dimethylamino) benzoate;
  • esters of cinnamic acid preferably 2-ethylhexyl 4-methoxycinnamate, isopentyl 4-methoxycinnamate, 2-ethylhexyl 2-cyano-3-phenylcinnamate (octocrylene);
  • esters of salicylic acid preferably 2-ethylhexyl salicylate, 4-isopropylbenzyl salicylate, homomethyl salicylic acid;
  • benzophenone preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone;
  • esters of benzalmalonic acid preferably di-2-ethylhexyl 4-methoxybenzmalonate
  • Triazine derivatives e.g. 2,4,6-trianilino- (p-carbo-2'-ethyl-1'-hexyloxy) -1, 3,5-triazine and octyltriazone.
  • Propane-1,3-dione e.g. 1- (4-tert-butylphenyl) -3- (4'methoxyphenyl) propane-1,3-dione;
  • Sulfonic acid derivatives of 3-benzylidene camphor e.g. 4- (2-oxo-3-bornylidene methyl) benzenesulfonic acid and 2-methyl-5- (2-oxo-3-bornylidene) sulfonic acid and their salts.
  • UV-A filters such as 1- (4'-tert-butylphenyl) -3- (4'-methoxyphenyl) propane-1, 3-dione or 1-phenyl-3-
  • UV-A filters 4'-isopropylphenyl) propane-1,3-dione.
  • the UV-A and UV-B filters can of course also be used in mixtures.
  • insoluble pigments namely finely dispersed metal oxides or salts, such as, for example, titanium dioxide, zinc oxide, iron oxide, aluminum oxide, cerium oxide, zirconium oxide, silicates (talc), barium sulfate and zinc stearate are also suitable for this purpose.
  • 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 have, however, it is also possible to use those particles which have an ellipsoidal shape or shape which differs in some other way from the spherical shape.
  • 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). Further suitable UV light protection filters can be found in the overview by P.Finkel in S ⁇ FW-Journal 122, 543 (1996).
  • 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 in particular those with 1 to 8 carbons in the alkyl radical, such as methyl and butyl glucoside;
  • Sugar alcohols with 5 to 12 carbon atoms such as sorbitol or mannitol,
  • Aminosugars such as glucamine.
  • Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, parabens, 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.
  • Perfume oils include mixtures of natural and synthetic fragrances. Natural fragrances are extracts of flowers (lily, lavender, roses, jasmine, neroli, ylang-ylang), stems and leaves (geranium, patchouli, petitgrain), fruits (anise, coriander, caraway, juniper), fruit peel (bergamot, lemon, Oranges), roots (mace, 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, mountain pine), resins and balms (galbanum, elemi, benzoin, myrrh, olibanum, opoponax).
  • Typical synthetic Fragrance compounds are products of the ester, ether, aldehyde, ketone, alcohol and hydrocarbon type. Fragrance compounds of the ester type are, for example, benzyl acetate, phenoxyethyl isobutyrate, p-tert-butylcyclohexyl acetate, linalyl acetate, dimethylbenzylcarbinylacetate, phenylethyl acetate, linalyl benzoate, benzyl formate, ethyl methyl phenyl glycinate, allyl cyclohexyl propylate pylate allylpropionate,
  • the ethers include, for example, benzylethyl ether, the aldehydes, for example, the linear alkanals having 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehy
  • fragrance oils of lower volatility which are mostly used as aroma components, are also suitable as perfume oils, e.g. sage oil, chamomile oil, clove oil, lemon balm oil, mint oil, cinnamon leaf oil, linden blossom oil, juniper berry oil, vetiver oil, oliban oil, galbanum oil, labolanum oil and lavandin oil.
  • 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.
  • Example 1 200 g (1 mol) of technical lauric acid were placed in a 1 liter stirred autoclave and 6 g of triethanolamine (corresponding to 3% by weight based on lauric acid) were added.
  • the autoclave was alternately evacuated and pressurized with nitrogen three times to remove traces of water that could lead to the formation of polyethylene glycol.
  • the autoclave was closed and heated to 100 ° C. and 44 g (1 mol) of propylene oxide were added in portions at a maximum pressure of 5 bar.
  • stirring was continued for 30 minutes and the reaction mixture was then cooled and let down.
  • the basic catalyst was neutralized by adding an appropriate amount of lactic acid.
  • the characteristics of the lauric acid + 1PO adduct are (quantities as% by weight):
  • a 10% by weight aqueous solution of sodium laureth sulfate was mixed with 2% by weight of the lauric acid propoxylate prepared according to Example 1 with stirring and thickened by adding 1.25% by weight sodium chloride.
  • a viscosity (Brookfield, spindle 1, room temperature, 20 rpm) of 8140 mPas was established. Even after storing the sample for 4 weeks at 40 ° C, the viscosity remained constant.
  • the same fatty alcohol sulfate solution as in the application example was mixed with 3% by weight of the nonionic thickener Laureth-2 and thickened with 1.5% by weight sodium chloride.
  • a viscosity of 8500 mPas was established.
  • the comparative example shows that, with the viscosity to be set approximately the same, smaller amounts of the organic thickener according to the invention (lauric acid + 1 PO) and of thickening sodium chloride are used.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
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Abstract

L'invention concerne des solutions tensio-actives aqueuses épaissies caractérisées en ce qu'elles contiennent comme épaisissants organiques des alkylèneglycols d'acide gras de la formule (I): R1COO(AlkO)nH, où R1CO représente un reste acyle linéaire ou ramifié, aliphatique, saturé et/ou insaturé avec 6 à 22 atomes de carbone; Alk représente CH¿2?CH2, CHCH3CH2 et/ou CH2CHCH3 et n vaut un chiffre compris entre 0,5 et 5.
PCT/EP1998/004605 1997-07-30 1998-07-22 Solutions tensio-actives aqueuses epaissies WO1999006518A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU88076/98A AU8807698A (en) 1997-07-30 1998-07-22 Thickened aqueous tenside solutions

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US5437097P 1997-07-30 1997-07-30
US60/054,370 1997-07-30
DE19736906A DE19736906A1 (de) 1997-08-25 1997-08-25 Verfahren zur Herstellung von sulfatierten Fettsäurealkylenglykolestern
DE19736906.5 1997-08-25

Publications (1)

Publication Number Publication Date
WO1999006518A1 true WO1999006518A1 (fr) 1999-02-11

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WO (1) WO1999006518A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1746141A4 (fr) * 2004-02-13 2010-04-07 Ajinomoto Kk Composition d' epaississement
CN114752055A (zh) * 2022-03-16 2022-07-15 华南理工大学 对硝基肉桂酸改性的快速反应性缔合型增稠剂及其制备方法与应用

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2024050A1 (de) * 1970-05-16 1971-12-09 Henkel & Cie GmbH, 4000 Düsseldorf Verfahren zur Herstellung von Alkylenglykolestern
DE1617445A1 (de) * 1967-10-31 1972-03-16 Dragoco Gerberding Co Gmbh Mittel zur Haut- und Haarpflege
SU745925A1 (ru) * 1975-04-22 1980-07-07 Экспериментально-Конструкторский И Технологический Институт Автомобильной Промышленности Моющее средство дл очистки металлической поверхности
JPS5986700A (ja) * 1982-11-09 1984-05-18 ライオン株式会社 粉セツケン組成物
US4470982A (en) * 1980-12-22 1984-09-11 The Procter & Gamble Company Shampoo compositions
EP0247552A2 (fr) * 1986-05-30 1987-12-02 SO.RI.FAR. S.r.l. Graisse autoémulsifiante pour utilisation pharmaceutique et cosmétique, sa préparation et son application
JPS63274149A (ja) * 1987-05-06 1988-11-11 Mitsubishi Gas Chem Co Inc 半導体処理剤
DE4431577A1 (de) * 1994-09-05 1996-03-07 Wella Ag Wasserstoffperoxidhaltiges Aerosolpräparat
US5639450A (en) * 1994-12-15 1997-06-17 Colgate-Palmolive Company Cleansing and conditioning cosmetic composition

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1617445A1 (de) * 1967-10-31 1972-03-16 Dragoco Gerberding Co Gmbh Mittel zur Haut- und Haarpflege
DE2024050A1 (de) * 1970-05-16 1971-12-09 Henkel & Cie GmbH, 4000 Düsseldorf Verfahren zur Herstellung von Alkylenglykolestern
SU745925A1 (ru) * 1975-04-22 1980-07-07 Экспериментально-Конструкторский И Технологический Институт Автомобильной Промышленности Моющее средство дл очистки металлической поверхности
US4470982A (en) * 1980-12-22 1984-09-11 The Procter & Gamble Company Shampoo compositions
JPS5986700A (ja) * 1982-11-09 1984-05-18 ライオン株式会社 粉セツケン組成物
EP0247552A2 (fr) * 1986-05-30 1987-12-02 SO.RI.FAR. S.r.l. Graisse autoémulsifiante pour utilisation pharmaceutique et cosmétique, sa préparation et son application
JPS63274149A (ja) * 1987-05-06 1988-11-11 Mitsubishi Gas Chem Co Inc 半導体処理剤
DE4431577A1 (de) * 1994-09-05 1996-03-07 Wella Ag Wasserstoffperoxidhaltiges Aerosolpräparat
US5639450A (en) * 1994-12-15 1997-06-17 Colgate-Palmolive Company Cleansing and conditioning cosmetic composition

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Week 8110, Derwent World Patents Index; AN 81-16967d, XP002083477 *
DATABASE WPI Week 8349, Derwent World Patents Index; AN 83-835105, XP002083551 *
DATABASE WPI Week 8426, Derwent World Patents Index; AN 84-161916, XP002083478 *
DATABASE WPI Week 8851, Derwent World Patents Index; AN 88-364313, XP002083476 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1746141A4 (fr) * 2004-02-13 2010-04-07 Ajinomoto Kk Composition d' epaississement
US8193137B2 (en) 2004-02-13 2012-06-05 Ajinomoto Co., Inc. Thickening composition
CN114752055A (zh) * 2022-03-16 2022-07-15 华南理工大学 对硝基肉桂酸改性的快速反应性缔合型增稠剂及其制备方法与应用

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