EP1419137A2 - Method for producing acyl amino acids - Google Patents

Method for producing acyl amino acids

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Publication number
EP1419137A2
EP1419137A2 EP20020706698 EP02706698A EP1419137A2 EP 1419137 A2 EP1419137 A2 EP 1419137A2 EP 20020706698 EP20020706698 EP 20020706698 EP 02706698 A EP02706698 A EP 02706698A EP 1419137 A2 EP1419137 A2 EP 1419137A2
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EP
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Application
Patent type
Prior art keywords
propanol
acid
glycol
ether
water
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Withdrawn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
EP20020706698
Other languages
German (de)
French (fr)
Inventor
Jürgen FALKOWSKI
Josef Koester
Ingomar Mrozek
Hans-Christian Raths
Karl Heinz Schmid
Andreas Syldath
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Cognis IP Management GmbH
Original Assignee
Cognis Deutschland GmbH and Co KG
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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/10Washing or bathing preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/02Preparations for cleaning the hair
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00Preparation of carboxylic acid amides
    • C07C231/02Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL AND VEGETABLE OILS, FATS, FATTY SUBSTANCES AND WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02Anionic compounds
    • C11D1/04Carboxylic acids or salts thereof
    • C11D1/10Amino-carboxylic acids; Imino-carboxylic acids; Fatty acid condensates thereof
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL AND VEGETABLE OILS, FATS, FATTY SUBSTANCES AND WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38Cationic compounds
    • C11D1/52Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides

Abstract

The invention relates to a method for producing acyl amino acids, according to which a mixture of at least one amino acid or the salt thereof and an alkali source is introduced into a reactor and said mixture is added to a polyisotopic element containing fatty acid halides of formula (I): R1COX, wherein R1 represents an alkyl or alkenyl group with between 6 and 22 carbon atoms and X represents chlorine, bromine or iodine. The invention also relates to the resultant products and to the use thereof in cosmetic products and in detergents, dishwashing detergents and cleaning agents.

Description

A process for the preparation of acylamino acids

Field of the Invention

The invention relates to a process for the preparation of acylamino acids in which the dosage of the fatty acid halide is carried out in a provided with mixer circuit line while the mixture of an amino acid and an alkali source is placed in the reactor, the product obtained therefrom, as well as the use of these acylamino acids in surfactant-containing preparations ,

State of the art

From the prior art are N-acyl amino acids such as N-acyl glutamates, known as mild co-surfactants for use in cosmetic preparations. They are prepared by reacting fatty acid chlorides with the amino group of the glutamic acid sodium salt in the presence of bases such as NaOH in an aqueous medium. A disadvantage of this method is that the lipophilic fatty acid chloride with the hydrophilic amino acid and the underlying salt is difficult to bring to react in an aqueous medium. This problem is trying to go out of the way by the addition of organic solvents such as acetone, methyl ethyl ketone, dioxane, polyols, tetrahydrofuran, tert-butanol or cyclohexane.

From the European Patent EP 0827950 A1, the acylation without addition of solvents is known, however, using high agitation. The disadvantage of this process is the much foam, so that this method for large-scale use is considered inappropriate.

This foaming can also result in mixing problems with this from acid chloride or alkali. Accordingly, this method is not suitable for large-scale preparation of acylamino acids.

The patent application EP 0857717 A1 describes a process for the preparation of acylamino acids by reaction of amino acids with fatty acid in the presence of water, alkali and polyols in conventional stirred vessels in the sense of a one pot reaction. The disadvantages of this method, the partly very high amounts of polyol required for a sufficient yield and the insufficient mixing. The high levels of polyols described therein are partly for the use of the resulting acylated amino acids undesirable. However, a reduction in the polyol content is detrimental to the low temperature properties of the product.

The object of the invention therefore has been to provide a process for the preparation of acylamino acids is available, which ensures uniform as possible mixing of the reaction components without foam volume, as can be observed in a traditional stirred tank reactors, as well as to provide a product available which is characterized by a good refrigeration and storage stability.

Description of the Invention

The present invention is a process for the preparation of acylamino acids, which comprises submitting a mixture of at least one amino acid or its salt and an alkali source in a reactor, and this in a mixing element with fatty acid halides of the formula

(I).

R COX (I)

in which R 1 represents an alkyl or alkenyl group containing 6 to 22 carbon atoms and X is chlorine, bromine iodine, was added.

Surprisingly, it has been found that one can produce acylamino, without resulting in the production thereof to excessive foaming, - as observed in traditional stirred tank reactors - and thus a uniform thorough mixing of the reaction components, ie, the amino acids, the alkali source and the fatty acid halides ensures is.

Another object of the invention is a Acylaminosäuregemisch containing

(A) 3 to 10 wt.% Sodium chloride,

(B) 0.1 to 4 wt.% Free fatty acids,

(C) 1 to 11 wt.% Free amino acids,

(D) 0.1 to 6 wt.% Low molecular weight alcohol and

(E) 30 to 80 wt.% Water. This product is obtainable in that the added water-soluble and / or water dispersible organic solvents are not separated after carrying out the process according to the invention.

The Acylaminosäureprodukt obtained thereby has a content of water-soluble and / or water-dispersible solvents, preferably low molecular weight monoalcohols, in the range of 0.1 to 6%, preferably 0.2 to 3 and more preferably in the range of 0.5 to 2.0 having%, based on the aqueous surfactant paste, which in turn has a water content of 30 to 80.%, preferably 45 to 70 wt.%, particularly preferably 50 to 65 wt.%. The required for adjusting the resistance to cold content of subsequently added solvents can be remarkably reduced. For example, only a maximum of 6 wt.%, Preferably at most 4 wt.% And particularly preferably 3 wt.% Post-added to polyols to achieve good low-temperature behavior. In favorable cases may even be dispensed subsequently added solvent.

Amino acids or salts thereof

When amino acids or their salts in the context of the invention, all known in the art from the literature α-amino acids are suitable, which can be acylated with fatty acid halides to form N-acylamino acids. Preferably marketed as amino acids glutamic acid, sarcosine, aspartic acid, alanine, valine, leucine, isoleucine, proline, hydroxyproline, glycine, serine, cysteine, cystine, threonine, histidine and salts thereof and, in particular glutamic acid, sarcosine, aspartic acid, glycine, lysine and salts thereof in question, particularly preferably glutamic acid, sarcosine, aspartic acid, glycine and lysine. The amino acids may be used in optically pure form or as racemic mixtures.

The amino acids or salts thereof in the inventive preparation of the surfactant mixtures in quantities of 20 to 70 wt .-%, preferably 35 to 60 and in particular 40 to 50 wt .-% -bezogen on the starting mixture - that is, used, prior to acid chloride addition ,

fatty acid halides

For the inventive process fatty acid halides, which form component (b), of the formula (I),

R 1 COX (I) is used, in which R 1 is an alkyl or alkenyl group containing 6 to 22, preferably 8 to 18 and in particular 8 to 16 carbon atoms and X is chlorine, bromine or iodine and preferably chlorine. Typical acid halides are octanoyl, nonanoyl, decanoyl, undeca- noylchlorid, lauroyl, tridecanoyl, myristoyl, palmitoyl, stearoyl, oleoyl and mixtures thereof.

The fatty acid halides used in the preparation of the surfactant mixtures according to the invention in a molar ratio acylatable compound / acid halide is from 1 to 1, 5 more preferably from 1 15 to 1; 3.

alkali source

For the novel process in the reactor an alkali source is presented. Among the alkali source of the invention in water or in a mixture of water and / or at least one water-soluble organic solvent dissolved alkali metal hydroxide or carbonate is understood within the meaning. Preferably, an aqueous solution of alkali hydroxide or dissolved in water and water-soluble organic solvents, alkali metal hydroxide, especially sodium hydroxide used (see, method).

In the method, the amount of alkali is dimensioned such that a pH-value of the starting mixture of amino acid or amino acid salt from 10 to 12.5, preferably from 11, 5 to 12.5 is established.

Water-soluble organic solvent

As the water-soluble or water-dispersible organic solvent, for example acetone, methyl ethyl ketone, dioxane, tetrahydrofuran, methanol, ethanol, propanol, i-propanol, butanol, t-butanol, pentanol, isopentanol, trimethylhexanol, glycerol, ethylene glycol, 2-methyl-propane come diol-1, 3, propylene glycol, dipropylene glycol, 1, 3 butylene glycol, 1, 2-butanediol, 1, 4-butanediol, Isopen- tyldiol, sorbitol, xylitol, mannitol, erythritol, pentaerythritol, ethanolamine, triethanolamine, 2-amino-2 -methyl-propanol, 1-amino-2-propanol, 1-amino-butanol-2, 1-methoxy-2-propanol, 2-Methoxye- THANOL, 2-ethoxyethanol, 2-propoxyethanol, 2-isopropoxyethanol, 2-butoxyethanol , 1-methoxy-2-propanol, 1-ethoxy-2-propanol, 1-propoxy-2-propanol, 1-isopropoxy-2-propanol, 1-butoxy-2-propanol, 1-isobutoxy-2-propanol, methoxyisopropanol , diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, Diethylenglycolmonopropylether, Diethylenglycolmonisopropyl- ether, diethylene glycol monobutyl ether, triethyl englycolmonomethylether, Triethylenglycolmono- ether, Triethylenglycolmonopropylether, Triethylenglycolmonisopropylether, triethylene glycol monobutyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene lenglycolmonopropylether, Dipropylenglycolmonisopropylether, dipropylene glycol monobutyl ether, hexylene glycol, triacetin, Propylenncarbonat, glycerol in question. As preferred solvent is ethanol, isopropanol, diethylene glycol monoethyl ether and triethanolamine are used. These solvents are also presented along with the amino acid and the alkali source in the reactor.

The water-soluble organic solvent are added in the inventive process in quantities of 0.1 to 15, preferably 0.2 to 7, and especially 0.2 to 4.0. Employed.

process

In a reactor (Fig. 1) is a mixture of at least one amino acid or its salt, preferably an aqueous solution of an amino acid or salt thereof and an alkali source, preferably, placed in water and / or aqueous organic solvents dissolved Alkalihydoxid or alkali metal carbonate and at 10 cooled to 20 ° C. water-soluble organic, preferably readily volatile solvent is added - in a particular embodiment of the invention can still - as described before. The reactor and the circulatory system are provided with a cooling jacket, which ensures the dissipation of the heat of reaction and a maximum temperature of 20 to 25 ° C ensured. The pH is adjusted prior to start of the reaction with alkali solution, preferably sodium hydroxide at about 12th Subsequently, the fatty acid halide and the alkali solution is metered in simultaneously so (see line concept) that the reactor temperature does not exceed 20 to 25 ° C and the pH-value of between 11 5 and 12.5. The dosage of the two reactants, preferably immersed in the alkali source in the reactor, ie, below the surface of the reaction mixture, and wherein the fatty acid chloride from the holding vessel in or in front of the mixing element (mixer). As a mixing element according to the invention dynamic or static mixers are understood. Under mixer encapsulated aggregates are understood to exclude the access of air during the mixing process. This may be (mixture using the flow energy) dynamic mixers with movable fittings and possibly additional fixed or static mixers with fixed fittings alone. The reactor and the mixing element are connected to each other via a circulation system. A circulation pump ensures throughout the reaction for the circulation of the reaction mixture, wherein the rear vehicle of the mixture is immersed in the reactor, ie, below the surface of the reaction mixture. After addition of the fatty acid chloride is stirred in the mixer for 2 to 5, preferably 2 hours at 20 to 25 ° C. and then heated for a further 2 to 5, preferably 2 hours to 60 to 80 ° C. organic solvent was added insofar as further components, these can be removed from the reaction mixture by distillation, preferably vacuum distillation or steam distillation again.

Since these solvents distil generally as an azeotrope with water, the concentration increase involved is offset by the addition of an adequate amount of water. Preferably, this distillation is carried out with simultaneous addition of water vapor, which reduces on the one hand, the foam volume during the distillation, on the other hand compensates for the loss of water. The distillation is preferably conducted at 60 to 80 ° C and a pressure of 200 to 400 mbar.

In a particular embodiment of the invention the organic solvents are largely subsequently removed after the reaction end by distillation from the mixture and remaining small amounts of solvent with the aid of a so-called Fryma system. In a further embodiment of the invention, the removal of the solvent from the mixture can also be effected by means of a membrane process. however, to dispense with the removal of the solvent, particularly when using low molecular weight monoalcohols, is preferred.

Then allowed to cool to room temperature and the pH value of the reaction mixture by addition of dilute hydrochloric acid to about 10 a. The reaction solution contains about 20 to 45 wt.%, Preferably 25 to 30 wt .-% acylated amino acid.

To keep the volume of foam is as low as possible in the reactor only with a speed of <60 / min, preferably stirred <30 / min. By mixing the absence of air foam formation is avoided during the entire running time.

commercial Applications

containing Acylaminosäuregemische produced via the inventive method

3 to 10 wt.% Sodium chloride, 0.1 to 4 wt.% Free fatty acids,

1 to 11 wt.% Free amino acids

0.1 to sixth% low molecular weight alcohol and

30 to 80 wt.% Water.

Preferred Acylaminosäuregemische

4 to 7 wt.% Sodium chloride, 0.5 to 3 wt.% Free fatty acids, 1, 5 to 8 wt.% Free amino acids

0.2 to. 3% low molecular weight alcohol and

45 wt to 70 wt.% Water,

contained and particularly preferred

4 to 5.5 wt.% Sodium chloride,

1 to 2.5 wt.% Free fatty acids,

3 by weight to. 6% free amino acids

0.5 to. 2% low molecular weight alcohol and

50 to 65 wt.% Water.

When using isopropanol and / or ethanol as a low molecular weight alcohol, this product is by weight for setting the cold resistance with a maximum of 6.%, Preferably a maximum of 4.% And particularly preferably up to 3 wt.% 1, 2-propylene glycol was added.

The product may be in surface-active preparations, such as detergents, budget and cosmetic and / or pharmaceutical preparations in amounts of 0.1 to 30.%, Preferably 0.5 to 10 wt.% And particularly preferably 1 to 5 wt .% are used. These can ren contain mild surfactants, oil bodies, emulsifiers, pearlescent waxes, consistency regulators, thickeners, superfatting agents, stabilizers, polymers, silicone compounds, fats, waxes, lecithins, phospholipids, biogenic agents, UV protection factors, antioxidants, deodorants, antiperspirants, antidandruff agents, film formers, swelling agents, insect repellents, self-tanning agents, tyrosine inhibitors (depigmentation agents), hydrotropes, solubilizers, preservatives, perfume oils, dyes and the like. As cosmetic and / or pharmaceutical cleaning preparations, for example hair shampoos come, oral and dental care products hair lotions, bubble baths, shower baths, creams, gels, lotions, alcoholic and aqueous / alcoholic solutions and emulsions in question.

surfactants

Suitable surfactants are anionic, nonionic, cationic and / or amphoteric or amphoteric surfactants may be included, which accounts for the compositions is usually about 1 to 70, preferably 5 to 50 and especially 10 to 30 wt .-%. Typical examples of anionic surfactants are soaps, alkylbenzenesulfonates, alkanesulfonates, olefin sulfonates, alkyl ether sulfonates, glycerol ether, α-methyl ester sulfonates, sulfofatty acids, alkyl sulfates, fatty alcohol ether sulfates, sulfates Glycerol ether, Fettsäureethersulfate, Hydroxymischethersulfate, monoglyceride (ether), fatty acid amide (ether) sulfates , mono- and dialkyl sulfosuccinates, mono- and dialkyl sulfosuccinamates, sulfotriglycerides, amide soaps, ether carboxylic acids and salts thereof, Fettsäurei- 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 ( in particular vegetable products (based on wheat) and alkyl ether) phosphates. Provided that the anionic surfactants contain polyglycol ether chains, these can have a conventional, but preferably have a narrowed homolog distribution. Typical examples of nonionic surfactants are fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol esters, fatty acid amide, fatty amine polyglycol ethers, alkoxylated triglycerides, mixed ethers and mixed formals, optionally partially oxidized alk (en) yl oligoglycosides or gluco- ronsäurederivate, fatty acid N-alkyl glucamides, protein hydrolyzates (particularly herbal products based on wheat), polyol, Zuckerester, sorbitan esters, polysorbates and amine oxides. If the nonionic surfactants contain polyglycol ether chains, these can have a conventional, but preferably have a narrowed homolog distribution. Typical examples of cationic surfactants are quaternary ammonium compounds, such as di- methyldistearylammoniumchloride and esterquats, more particularly quaternized aminestersalze Fettsäuretrialkanol-. Typical examples of amphoteric or zwitterionic surfactants are alkylbetaines, alkylamidobetaines, aminopropionates, aminoglycinates, imidazolinium betaines and sulfobetaines. The surfactants mentioned are all known compounds. Their structure and production can be found in relevant synoptic works, for example J. Falbe (ed.), "Surfactants in Consumer Products", Springer Verlag, Berlin, 1987, pp 54-124 or J. Falbe (ed.), "Catalysts referred surfactants and mineral oil additives ", Thieme Verlag, Stuttgart, 1978, pp 123-217. Typical examples of particularly suitable mild, ie particularly skin-compatible, surfactants are fatty alcohol polyglycol ether sulfates, monoglyceride sulfates, mono- and / or dialkyl sulfosuccinates, fatty acid taurides, acid glutamate fat, α-olefinsulfonates, ether carboxylic acids, alkyl oligoglucosides, fatty acid glucamides, alkylamidobetaines, amphoacetals and / or protein fatty acid condensates , preferably based on wheat proteins.

Olkörper

As Olkörper example, Guerbet alcohols based on fatty alcohols having 6 to 18, preferably 8 to 10 carbon atoms, esters of linear C6-C22-fatty acids with linear or branched C6-C22-fatty alcohols or esters of branched C6-Ci3-carboxylic acids with linear or branched C6-C22-fatty alcohols, such as myristyl myristate, myristyl palmitate, myristyl stearate, Myristylisostearat, myristyl, Myristylbehenat, Myristylerucat, cetyl myristate, cetyl palmitate, Ce tylstearat, Cetylisostearat, cetyl oleate, cetyl behenate, Cetylerucat, Stearylmyristat, stearyl palmitate, stearyl stearate, Stearylisostearat, stearyl oleate, stearyl behenate , Stearylerucat, isostearyl, isostearyl palmitate, Isostearylstearat, isostearyl isostearate, Isostearyloleat, isostearyl behenate, Isostearyloleat, oleyl myristate, oleyl palmitate, oleyl stearate, oleyl isostearate, oleyl oleate, Oleylbehenat, oleyl erucate, behenyl myristate, behenyl palmitate, behenyl, Behenylisostearat, behenyl oleate, behenyl behenate, Erucyl, erucyl, erucyl, erucyl, erucyl, erucyl, and erucyl erucate. Also suitable are esters of linear C6-C22-fatty acids with branched alcohols, especially 2-ethylhexanol, esters of CI8-C 3 8-alkylhydroxy carboxylic acids with linear or branched C6-C22-fatty alcohols (cf., DE 19756377 A1), in particular dioctyl Malate, esters of linear and / or branched fatty acids with polyhydric alcohols (for example propylene glycol, dimer diol or trimer triol) and / or Guerbet alcohols, Triglyce- ride on the basis Cδ-Cio-fatty acids, liquid mono- / di- / triglyceride mixtures based on of Cδ-Ciβ- fatty acids (see. EP 97/00434), esters of C6-C22-fatty alcohols and / or Guerbet alcohols with aromatic carboxylic acids, in particular benzoic acid, esters of C2-Ci2-dicarboxylic acids with linear or branched alcohols having 1 to 22 carbon atoms or polyols having 2 to 10 carbon atoms and 2 to 6 hydroxyl groups, vegetable oils, branched primary alcohols, substituted cyclohexanes, linear and branched C6-C22 fatty alcohol carbonates, such as Dic aprylyl Carbonate (Cetiol CC), Guerbet carbonates based on fatty alcohols having 6 to 18, preferably 8 to 10 carbon atoms, esters of benzoic acid 2 2-alcohols with linear and / or branched C6-C (for example, Finsolv® TN), linear or branched, symmetrical or asymmetrical dialkyl ethers having 6 to 22 carbon atoms per alkyl group, such as for example, dicaprylyl ether (Cetiol OE), ring opening products of epoxidized Fettsäureestern with polyols, silicone oils (cyclomethicones, Siliciummethi- contypen etc.) and / or aliphatic or naphthenic hydrocarbons, such as for example squalane, squalene or dialkyl.

Emulqatoren

As emulsifiers for example, nonionic surfactants from at least one of the following groups:

> Addition products of from 2 to 30 mol ethylene oxide and / or 0 to 5 mol propylene oxide onto linear fatty alcohols having 8 to 22 carbon atoms, onto fatty acids having 12 to 22 carbon atoms, to alkylphenols having 8 to 15 C atoms in the alkyl group and alkylamines containing 8 to 22 carbon atoms in the alkyl radical;

> Alkyl and / or alkenyl oligoglycosides having 8 to 22 carbon atoms in the alk (en) yl group and ethoxylated analogs thereof; > Addition products of from 1 to 30 moles of ethylene oxide with fatty acids insertion products of 1 to 30 mol ethylene oxide into fatty acid methyl ester

> Addition products of from 1 to 15 mol ethylene oxide onto castor oil and / or hydrogenated castor oil;

> Addition products of from 15 to 60 mol ethylene oxide onto castor oil and / or hydrogenated castor oil;

> Partial esters of glycerol and / or sorbitan with unsaturated, linear or saturated, branched fatty acids having 12 to 22 carbon atoms and / or hydroxycarboxylic acids having 3 to 18 carbon atoms and adducts thereof with 1 to 30 moles of ethylene oxide;

> Partial esters of polyglycerol (average self-condensation degree 2 to 8), polyethylene glycol (molecular weight 400 to 5,000), trimethylolpropane, pentaerythritol, sugar alcohols (for example sorbitol), alkyl glucosides (for example methyl glucoside, butyl glucoside, lauryl glucoside) and polyvinyl lyglucosiden (eg cellulose) with saturated and / or unsaturated, linear or branched fatty acids having 12 to 22 carbon atoms and / or hydroxycarboxylic acids having 3 to 18 carbon atoms and adducts thereof with 1 to 30 moles of ethylene oxide;

> Mischester of pentaerythritol, fatty acids, citric acid and fatty alcohol according to DE 1165574 PS and / or Mischester of fatty acids having 6 to 22 carbon atoms, methyl glucose and polyols, preferably glycerol or polyglycerol.

> Mono-, di- and trialkyl phosphates and mono-, di- and / or tri-PEG-alkyl phosphates and salts thereof;

> Lanolin alcohol;

> Polysiloxane-polyalkyl-polyether copolymers and corresponding derivatives;

> Block copolymers, for example polyethylene glycol-30 dipolyhydroxystearate;

> Polymeric emulsifiers such as Pemulen grades (TR-1, TR-2) from Goodrich;

> Polyalkylene glycols and

> Glycerol.

The addition products of ethylene oxide and / or propylene oxide with fatty alcohols, fatty acids, alkylphenols or with castor oil are known, commercially available products. These are homolog mixtures whose average degree of alkoxylation the ratio between the quantities of ethylene oxide and / or propylene oxide and substrate with which the addition reaction is carried out, corresponds. Ci2 / i8-fatty acid mono- and diesters of addition products of ethylene oxide onto glycerol are known from DE 2024051 as refatting agents for cosmetic preparations.

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. With regard to the glycoside radical is concerned, both monoglycosides, in which a cyclic sugar radical is glycosidically bonded to the fatty alcohol, and also oligomeric glycosides with a degree of oligomerization are suitable preferably up to about. 8 The degree of oligomerization here is a statistical average value which is typical of such technical products homolog distribution.

Typical examples of suitable partial glycerides are hydroxystearic acid monoglyceride, stearic acid diglyceride hydroxy, isostearic acid, Isostearinsäurediglycerid, Ölsäuremonoglyce- chloride, oleic acid diglyceride, Ricinolsäuremoglycerid, Ricinolsäurediglycerid, Linolsäuremonoglycerid, Linolsäurediglycerid, Linolensäuremonoglycerid, Linolensäurediglycerid, Erucasäuremonoglycerid, Erucasäurediglycerid, Weinsäuremonoglycerid, Weinsäurediglycerid, Citronensäuremonoglycerid, Citronendiglycerid, Äpfelsäuremonoglycerid, malic acid diglyceride and may contain technical mixtures thereof, the minor product of the manufacturing process small amounts of triglyceride. Likewise suitable are addition products of 1 to 30, preferably 5 to 10 mol ethylene oxide onto the partial glycerides mentioned.

As sorbitan esters sorbitan, sorbitan sesquiisostearate, Sorbitan, sorbitan triisostearate, sorbitan monooleate, sorbitan, sorbitan, Sorbitanmonoerucat, Sorbitansesquierucat, Sorbitandierucat, Sorbitantrierucat, Sorbitanmonorici- noleat, Sorbitansesquiricinoleat, Sorbitandiricinoleat, Sorbitantriricinoleat, Sorbitanmonohydro- xystearat, Sorbitansesquihydroxystearat, Sorbitandihydroxystearat, Sorbitantrihydroxystearat, sorting bitanmonotartrat , Sorbitansesquitartrat, Sorbitanditartrat, Sorbitantritartrat, Sorbitanmonocitrat, Sorbitansesquicitrat, Sorbitandicitrat, sorbitan, sorbitan, sorbitan, sorbitan, sorbitan and technical mixtures thereof. Likewise suitable are addition products of 1 to 30, preferably 5 to 10 mol ethylene oxide onto said sorbitan esters.

Typical examples of suitable polyglycerol esters are Polyglyceryl-2 Dipolyhydroxystearate (de- hymuls® PGPH), Polyglycerin-3-Diisostearate (Lameform® TGI), Polyglyceryl-4 Isostearate (iso LAN® Gl 34), Polyglyceryl-3 Oleate, Diisostearoyl polyglyceryl (3 Diisostearate (Isolan® PDI), Polyglyceryl-3 methylglucose Distearate (Tego Care ® 450), Polyglyceryl-3 Beeswax (Cera Bellina®), Polyglyceryl-4 Caprate (polyglycerol Caprate T2010 / 90), Polyglyceryl-3 Cetyl ether Chimexane® NL), Polyglyceryl-3 Distearate (Cremophor® GS 32) and Polyglyceryl polyricinoleates (Admul® WOL 1403) polyglyceryl dimerates Isostearate and mixtures thereof. Examples of further suitable polyol esters are the, optionally reacted with 1 to 30 moles of ethylene oxide, 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. Furthermore, zwitterionic surfactants can be used as emulsifiers. Zwitterionic surfactants are 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 are the betaines such as N-alkyl-N, N- dimethylammonium glycinates, for example cocoalkyldimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammonium glycinates, for example lammoniumglycinat the Kokosacylaminopropyldimethy-, and 2-alkyl-3-carboxylmethyl -3-hydroxyethylimidazoline glycinate each having 8 to 18 carbon atoms in the alkyl or acyl group as well as the Kokosacylaminoethylhydroxyethylcarboxymethyl-. Particular preference is known by the CTFA name Cocamidopropyl Betaine fatty acid amide derivative. Likewise suitable emulsifiers are ampholytic surfactants. Ampholytic surfactants are surface-active compounds which, in addition to a C / iβ alkyl or acyl group in the molecule at least one free amino group and at least one -COOH or -Sθ3H group and are capable of forming inner salts. Examples of suitable ampholytic surfactants are N-alkyl glycines, N-alkyl propionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids containing around 8 to 18 are each C -atoms in the alkyl group. Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethyl aminopropionate and C12 / 18 acyl sarcosine. Finally, cationic surfactants are also suitable emulsifiers, those of the esterquat type, preferably methyl-quaternized difatty acid triethanolamine ester salts, being particularly preferred.

Fats and waxes

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, suitable waxes are inter alia natural waxes such as candelilla wax, carnauba wax, Japan wax, esparto grass, cork wax, Guarumawachs, rice germ oil wax, sugar cane wax , ouricury wax, montan wax, beeswax, shellac wax, spermaceti, lanolin (wool wax), uropygial grease, ceresin, ozokerite (earth wax), petrolatum, paraffin waxes, microcrystalline waxes; chemically modified waxes (hard waxes), such as Montanesterwachse, sasol waxes, hydrogenated jojoba waxes and synthetic waxes such as polyalkylene waxes and polyethylene glycol waxes. Besides the fats, suitable additives are also fat-like substances, such as lecithins and phospholipids pide in question. The term lecithins is understood by those skilled those glycerophospholipids which form from fatty acids, glycerol, phosphoric acid and choline by esterification. Lecithins are therefore also often as phosphatidylcholines (PC) in the professional world and follow the general formula

wherein R typically represents linear aliphatic hydrocarbon radicals containing 15 to 17 carbon atoms and up to 4 cis-double bonds. Examples of natural lecithins which may be mentioned are the cephalins, which are also referred to as phosphatidic acids and derivatives of 1, 2-diacyl-sn-glycerol-3-phosphoric acids represent. By contrast, phospholipids are generally understood to be mono- and preferably diesters of phosphoric acid with glycerol (glycerol phosphates), which are normally classed as fats. Sphingosines and Sphin- come golipide in question.

pearlescent

Pearlescent waxes are, for example, alkylene glycol esters, especially ethylene glycol distearate stearate; Fettsaurealkanolamide, especially Kokosfettsaurediethanolamid; Partial glycerides, especially stearic acid monoglyceride; Esters of polybasic, optionally hydroxysubstituted 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 have at least 24 carbon atoms in total, especially laurone 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 and 2 to 10 hydroxyl groups and mixtures thereof.

Consistency Factors and Thickeners

The consistency factors mainly used are fatty alcohols or hydroxyfatty alcohols containing 12 to 22 and preferably 16 to 18 carbon atoms and also partial glycerides, fatty acids or hydroxyfatty acids. A combination of these substances with alkyl oligoglucosides to and / or fatty acid N-methylglucamides of identical chain length and / or polyglycerol poly-12- hydroxystearates is. Suitable thickeners are, for example, Aerosil types (hydrophilic silicas), polysaccharides, more especially xanthan gum, guar-guar, agar-agar, alginates and TY- loose, carboxymethyl cellulose and hydroxyethyl cellulose, also relatively high molecular Polyethylengly- colmono- and diesters of fatty acids, polyacrylates (eg Carbopols® and Pemulen grades from Goodrich; Synthalene® from Sigma; Keltrol grades from Kelco; Sepigel grades from Seppic; Salcare- types from Allied Colloids), polyacrylamides, polymers, polyvinyl alcohol and polyvinyl pyrrolidone, surfactants such as ethoxylated fatty acid glycerides esters of fatty acids with polyols such as pentaerythritol or trimethylolpropane, fatty alcohol ethoxylates with a narrowed homolog distribution or alkyl oligoglucosides and electrolytes such as sodium chloride and ammonium chloride.

superfatting

Superfatting agents may be used such as for example, lanolin and lecithin and also polyethoxylated or acylated lanolin xylierte and lecithin derivatives, polyol fatty acid esters, monoglycerides and Fettsaurealkanolamide, the latter also serving as foam stabilizers.

stabilizers

Metal salts of fatty acids, such as magnesium, aluminum and / or zinc stearate or ricinoleate may be used.

polymers

Suitable cationic polymers are for example cationic cellulose derivatives, for example, a quaternized hydroxyethylcellulose obtainable under the name Polymer JR 400® from Amerchol, cationic starch, copolymers of diallyl ammonium salts and acrylamides, quaternized vinylpyrrolidone / vinylimidazole polymers, for example Luviquat (BASF) , condensation products of polyglycols and amines, quaternized collagen polypeptides, for example lauryl- dimonium hydroxypropyl hydrolyzed collagen (Lamequat®L / Grunau), quaternized Weizenpoly- peptide, polyethyleneimine, cationic silicone polymers, for example amodimethicones, copolymers of adipic acid and dimethylaminohydroxypropyl (Cartaretine® / Sandoz ), copolymers of acrylic acid with dimethyl diallyl ammonium chloride (Merquat 550 / Chemviron), Polyaminopolya- mide, for example as described in FR 2252840 A, and crosslinked water-soluble polymers thereof, cationic chitin derivatives such as quaternized Chi tosan, optionally in microcrystalline distribution, condensation products of dihaloalkyls, for example dibromobutane, with bis-dialkylamines, for example bis-dimethylamino-1, 3-propane, cationic guar gum such as, for example, Jaguar® CBS, Jaguar® C-17, Jaguar® C-16 of Celanese, quaternized ammonium salt polymers such as, for example, 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, methyl vinyl ether / maleic anhydride copolymers and esters thereof, uncrosslinked and polyol-crosslinked polyacrylic acids, Acrylamidopropyltrimethylammoni - trimethylammonium chloride / acrylate copolymers, octylacrylamide / methyl methacrylate / tert. Butylaminoethylmethacry- lat / 2 Hydroxyproylmethacrylat copolymers, polyvinylpyrrolidone, vinylpyrrolidone / vinyl acetate copolymers, vinylpyrrolidone / dimethylaminoethyl methacrylate / vinyl caprolactam terpolymers and optionally derivatized cellulose ethers and silicones. Other suitable polymers and thickeners can be found in Cosmetics & Toiletries, Vol. 108, May 1993, page 95 et seq.

Silicone Compounds

Suitable silicone compounds are, for example, dimethyl polysiloxanes, Methylphenylpolysilo- Xane, cyclic silicones and amino-, fatty acid-, alcohol-, polyether-, epoxy-, fluorine-, glycoside- and / or alkyl-modified silicone compounds which may be both liquid and resin-like at room temperature. Also suitable are simethicones, which are mixtures of dimethicones with an average chain length of 200 to 300 dimethylsiloxane units and hydrogenated silicates. A detailed review of suitable volatile silicones is found in Todd et al. in Cosm. 91, 27 (1976).

UV üchtschutzfilter and antioxidants

Under UV light protection factors are, for example liquid at room temperature or crystalline present, organic substances (light protection filters) to be understood, that are able to absorb ultraviolet rays and give off the absorbed energy again in the form of longer-wave radiation, for example heat. UVB filters can be oil-soluble or water soluble. Oil-soluble substances which may be mentioned for example:> 3-benzylidene camphor or 3-benzylidene norcamphor and derivatives thereof, for example 3- (4-methyl benzylidene) camphor as described in EP 0693471 B1;

> 4-aminobenzoic acid derivatives, preferably 4- (dimethylamino) benzoic acid 2-ethylhexyl ester, 4- (dimethylamino) benzoic acid 2-octyl ester and 4- (dimethylamino) benzoesäureamylester;

> Esters of cinnamic acid, preferably 4-methoxycinnamic acid 2-ethylhexyl ester, 4-Methoxyzimtsäu- repropylester, 4-methoxycinnamic acid isoamyl ester 2-cyano-3,3-phenylcinnamate, 2-ethylhexyl (Octocrylene);

> Esters of salicylic acid, preferably 2-ethylhexyl salicylate, 4-isopropyl benzyl salicylate;

> Derivatives of benzophenone, preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone;

> Esters of benzalmalonic acid, preferably 4-methoxy-2-ethylhexyl ester;

> Triazine derivatives, such as 2,4) 6-trianilino- (p-carbo-2'-ethyl-1'-hexyloxy) -1, 3,5-triazine and Octyl Triazone as described in EP 0818450 A1 or Dioctyl Butamido Triazone (Uvasorb® HEB);

> Propane-1, 3-diones, such as 1 - (4-tert-butylphenyl) -3- (4'methoxyphenyl) propane-1, 3-dione;

> Ketotricyclo (5.2.1.0) decane derivatives as described in EP 0694521 B1.

Water-soluble substances are:

> 2-phenyl-5-sulfonic acid and alkali, alkaline earth, ammonium, alkylammonium nium-, alkanolammonium and glucammonium;

> Sulfonic acid derivatives of benzophenones, preferably 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid and its salts;

> Sulfonic acid derivatives of 3-benzylidenecamphor, eg 4- (2-oxo-3-bornylidenemethyl) benzene-sulfonic acid and 2-methyl-5- (2-oxo-3-bornylidene) sulfonic acid and salts thereof.

Typical UV-A filters are, in particular, derivatives of benzoylmethane, for example 1- (4'-tert-butylphenyl) -3- (4'-methoxyphenyl) propane-1, 3-dione, 4-tert-butyl -4'-methoxydi- benzoylmethane (Parsol 1789), 1-phenyl-3- (4'-isopropylphenyl) -propane-1, 3-dione and Enaminver- bonds, as described in DE 19712033 A1 (BASF). The UV-A and UV-B filters can of course also be used in mixtures. Particularly favorable combinations consist of the derivatives of benzoyl methane ,, for example 4-tert-butyl-4'-methoxydibenzoylmethane (Parsol 1789) and 2-cyano-3,3-phenylcinnamate, 2-ethylhexyl (octocrylene) in combination with esters of cinnamic acid , preferably 4-methoxycinnamic acid 2-etfιylhexylester and / or 4-methoxycinnamic säurepropylester and / or isoamyl 4-methoxycinnamate. such as these are advantageously combination nations with water-soluble filters such as 2-phenylbenzimidazole-5-sulfonic acid and combined their alkali, alkaline earth, ammonium, alkylammonium, alkanolammonium and glucammonium salts.

Besides the soluble substances mentioned, insoluble light-blocking pigments, ie finely dispersed metal oxides or salts used for this purpose in question. Examples of suitable metal oxides are in particular zinc oxide and titanium dioxide and also oxides of iron, zirconium, silicon, manganese, aluminum and cerium and mixtures thereof. As salts of silicates can be used (talc), barium sulfate or zinc stearate. The oxides and salts are used in the form of the pigments for skincare and skin-protective emulsions and decorative cosmetics. The particles should have a mean diameter of less than 100 nm, preferably between 5 and 50 nm and in particular between 15 and 30 nm. You can have a spherical shape, but it is also such particles are used which have an ellipsoidal or otherwise deviates from the spherical shape. The pigments can also be surface treated, ie be hydrophilicized or hydrophobicized. Typical examples are coated titanium dioxides, for example Titandioxid T 805 (Degussa) or Eusolex® T2000 (Merck). Suitable hydrophobic coating materials are, above all, silicones and particularly Trialkoxyoctyl- silanes or simethicone. In sunscreens, so-called micro or nano pigments are preferably used. Preferably micronized zinc oxide is used. Further suitable UV light protection filters in the review by P. Finkel in SFW-Journal 122, 543 (1996) and perfumery and cosmetics 3 (1999), page 11ff be taken from.

Besides the two aforementioned groups of primary sun protection factors, secondary sun protection agents can be used of the antioxidant type which interrupt the photochemical reaction chain which is triggered when UV radiation penetrates into the skin. Typical examples thereof are amino acids (for example glycine, histidine, tyrosine, tryptophan) and derivatives thereof, imidazoles (for example urocanic acid) and derivatives thereof, peptides such as D, L-carnosine, D-carnosine, L-carnosine and derivatives thereof (for example, anserine), carotenoids, carotenes (for example α-carotene, beta-carotene, lycopene) and derivatives thereof, chlorogenic acid and derivatives thereof, lipoic acid and derivatives thereof (for example di- hydroliponsäure), aurothioglucose, propylthiouracil and other thiols (for example thioredoxin, Glu tathion, cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, γ-linoleyl, cholesteryl and glyceryl esters ) and salts thereof, dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and derivatives thereof (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) and sulfoximine compounds (for example Buthioninsulfoximine, homocysteine ​​sulfoximine, Butioninsulfone, penta-, hexa-, Heptathioninsulfoxi- min) in very gerin gen tolerated doses (for example pmol to .mu.mol / kg), also (metal) chelating agents (for example α-hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin), α-hydroxy acids (for example citric nensäure, lactic acid, malic acid), humic acid, bile acid, bile extracts , bilirubin, biliverdin, EDTA, EGTA and derivatives thereof, unsaturated fatty acids and their derivatives (eg, γ-linolenic acid, linoleic acid, oleic acid), folic acid and derivatives thereof, ubiquinone and ubiquinol and derivatives thereof, vitamin C and derivatives (for example ascorbyl palmitate, Mg ascorbyl phosphate, ascorbyl acetate), tocopherols and derivatives (for example vitamin e acetate), vitamin A and derivatives (vitamin A palmitate) and Koniferyl- benzoate of benzoin, rutinic acid and derivatives thereof, α-glycosyl rutin, ferulic acid, Furfury- lidenglucitol, carnosine, butylhydroxytoluene, butylhydroxyanisole, Nordihydroguajakharzsäure, Nordic hydroguajaretsäure, trihydroxybutyrophenone, uric acid and derivatives thereof, mannose and derivatives thereof, superoxide dismutase, Z ink and derivatives thereof (for example ZnO, ZnS0 4), selenium and derivatives thereof (for example selenium methionine), stilbenes and derivatives thereof (for example stilbene oxide, trans-stilbene oxide) and the present invention suitable derivatives (salts, esters, ethers, sugars, nucleotides, of these active compounds mentioned nucleotide side, peptides and lipids).

Bioqene agents

Biogenic agents, for example, tocopherol, tocopherol acetate, tocopherol palmitate, retinol, bisabolol, allantoin, phytantriol, panthenol, AHA acids, amino acids, ceramides, pseudoceramides, essential oils, plant extracts and vitamin complexes are to be understood.

Deodorants and Antimicrobial Agents

Cosmetic deodorants (deodorants) act against body odors, masking or eliminating them. Body odors arise by the action of skin bacteria on apocrine perspiration, with the unpleasant-smelling degradation products are formed. Accordingly, deodorants comprise active ingredients which act as antimicrobial agents, enzyme inhibitors, odor absorbers or odor masking agents. As antimicrobial agents suitable in principle are all active substances against gram positive bacteria such. B. 4-hydroxybenzoic acid and its salts and esters, N- (4-chlorophenyl) -N '- (3,4 dichlorophenyl) urea, 2,4,4'-trichloro-2' -hydroxydiphenylether (Triclosan), 4-chloro -3,5-dimethylphenol, 2,2 '-methylene-bis (6-bromo-4-chlorophenol), 3-methyl-4- (1-methylethyl) phenol, 2-benzyl-4-chlorophenol, 3- (4 -Chlorphenoxy) -1, 2-propanediol, 3-iodo-2-propynyl butylcarbamate, chlorhexidine, 3,4,4 '-Trichlorcarbanilid (TTC), antibacterial fragrances, thymol, thyme oil, eugenol, oil of cloves, menthol, mint oil, farnesol , phenoxyethanol, glycerol monocaprate, glycerol monocaprylate, glycerol monolaurate (GML), diglycerol monocaprate (DMC), salicylic acid-N-alkylamides such. As salicylic acid-n-octylamide decylamid salicylic acid-n-or. As esterase enzyme inhibitors are suitable. These are preferably trialkyl such as trimethyl citrate, tripropyl, triisopropyl, tributyl citrate and especially triethyl citrate (Hydagen® CAT, Henkel KGaA, Dusseldorf / FRG). The substances inhibit enzyme activity and thus reduce odor formation. Further substances that come into consideration as esterase inhibitors are sterol sulfates or phosphates, for example lanosterol, cholesterol, campesterol, stigmasterol and sitosterol sulfate or phosphate, dicarboxylic acids and esters thereof such as glutaric acid, monoethyl glutarate, Glutarsäurediethy- lester, adipic acid, adipic acid monoethyl ester, malonic acid and malonic acid diethyl ester, hydroxycarboxylic acids and esters thereof such as citric acid, malic acid, tartaric acid or diethyl tartrate, and zinc glycinate.

Suitable odor absorbers are substances that can absorb odor-forming compounds and firmly hold own. They also reduce the partial pressure of the individual components, thus reducing their speed of propagation. It is important that the perfumes remain unaffected. Odor absorbers are not active against bacteria. They contain, for example, as main constituent, a complex zinc salt of ricinoleic acid or specific, largely odor-neutral fragrances which are known in the art as "fixatives", such. B. Extracts of Labda- num or styrax or certain abietic acid derivatives. Odor-masking function perfumes or perfume oils that give in addition to their function as odor the deodorants their respective fragrance note. which may be mentioned as perfume oils mixtures of natural and synthetic fragrances. Natural fragrances are extracts from flowers, stems and leaves, fruits, fruit peel, roots, woods, herbs and grasses, needles and branches, resins and balsams. Animal raw materials in question, for example civet and beaver. Typical synthetic fragrance compounds are products of the ester, ether, aldehyde, ketone, alcohol and hydrocarbon type. Fragrance compounds of the ester type are benzyl acetate, p-tert-butylcyclohexyl acetate, linalyl acetate, phenylethyl acetate, Linalyl benzoate, benzyl formate, Allylcyclohexylpropionat, Styrallylpropionat and benzyl salicylate. The ethers include, for example, benzyl ethyl ether, the aldehydes include, for example, the linear alkanals having 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehyde, cyclamenaldehyde, hydroxycitronellal, lilial and bourgeonal, the ketones include, the ionones and methyl alcohols are anethol, citronellol, eugenol, isoeugenol, geraniol, linalool, phenylethyl alcohol and terpineol, and the hydrocarbons include mainly the Teφene and balsams. Preferably, however, mixtures of different odorants, which together produce a pleasing fragrance note. Essential oils of lower volatility, which are mostly used as aroma components, are also suitable as perfume oils, eg sage oil, chamomile oil, clove oil, melissa oil, mint oil, cinnamon leaf oil, lime blossom oil, juniper berry oil, vetiver oil, olibanum, Gal banumöl, labdanum and lavender oil. Preferably, bergamot oil, dihydromyrcenol, lilial, lyral, citronellol, phenylethyl alcohol, -Hexylzimtaldehyd, geraniol, benzyl acetone, Cyclame- be naldehyd, linalool, Boisambrene Forte, Ambroxan, indole, hedione, Sandelice, lemon oil, nenöl Mandari-, orange oil, allyl amyl glycolate, Cyclovertal, lavandin, clary sage oil, ß-damascones, geranium bourbon, cyclohexyl, Vertofix Coeur, Iso e Super, Fixolide NP, Evernyl, Iral- your gamma, phenylacetic acid, geranyl acetate, benzyl acetate, rose oxide, romilat, irotyl and Flo ramat alone or in mixtures.

Antiperspirants (antiperspirants) eccrine sweat glands reduce by influencing the activity perspiration and thus counteract underarm wetness and body odor. Aqueous or anhydrous formulations of antiperspirants typically comprise the following ingredients:

astringent active principles,

> Oil components,

> Nonionic emulsifiers,

> Co-emulsifiers,

> Bodying agents,

> Auxiliaries such. For example, thickeners or complexing agents and / or

> Non-aqueous solvents such. Ethanol, propylene glycol and / or glycerin.

Suitable astringent antiperspirant active ingredients are primarily salts of aluminum, zirconium or zinc. Such suitable antiperspirant active ingredients are, for example, aluminum chloride, aluminum chlorohydrate, aluminum sesquichlorohydrate and complex compounds thereof. B. with propylene glycol. 1, 2 Aluminiumhydroxyallantoinat, Aluminiumchlo- ridtartrat, aluminum zirconium trichlorohydrate, aluminum zirconium tetrachlorohydrate, aluminum zirconium pentachlorohydrate and complex compounds thereof. Eg with amino acids such as glycine. In addition, customary oil-soluble and water-soluble auxiliaries may be present in minor amounts in antiperspirants. Oil-soluble auxiliaries can be:

> Anti-inflammatory, skin-protecting or pleasant-smelling essential oils,

> Synthetic skin-protecting agents and / or

> Oil-soluble perfume oils.

Customary water-soluble additives are, for example, preservatives, water-soluble fragrances, pH adjusting agents, for example buffer mixtures, water-soluble thickeners, for example water-soluble natural or synthetic polymers such as xanthan gum, hydroxyethylcellulose, polyvinylpyrrolidone or high molecular weight polyethylene oxides.

film formers

Customary film formers are, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinylpyrrolidone, vinylpyrrolidone-vinyl acetate copolymers, polymers of Acrylsäu- rereihe, quaternary cellulose derivatives, collagen, hyaluronic acid and salts thereof and similar compounds.

Antidandruff agents

, Baypival® (Climbazole), Ketoconazol®, (4-acetyl-I - antidandruff agents are piroctone olamine (2- (1 H) -pyridinonmonoethanolaminsalz 1-hydroxy-4-methyl-6- (2,4,4-trimythylpentyl)) include - 1 - {4- [2- (2,4-dichlorophenyl) r-2- (1 H-imidazol-1 -y lmethyl) -1, 3-dioxylan-c-4-ylmethoxyphenyl} piperazine, ketoconazole, elubiol, selenium disulphide , colloidal sulfur, Schwefelrizinolpolyehtoxylat, Schwfel tar distillate, salicylic acid (or in combination with lorophen Hexach), undecylenic acid monoethanolamide sulfosuccinate Na salt, Lamepon® UD (protein undecylenic acid condensate), zinc pyrithione, magnesium pyrithione Aluminiumpyrithion and / Dipy- rithion- magnesium sulfate.

swelling agent

Suitable swelling agents for aqueous phases are montmorillonites, clay mineral substances serve, Pemulen and alkyl-modified Carbopol types (Goodrich). Other suitable polymers and swelling agents can Lochhead's review in Cosm. 108, 95 (1993) are taken.

Insect repellents

Suitable insect repellents are N, N-diethyl-m-toluamide, 1, 2-pentanediol or ethyl butylacetyl aminopropionates in question and self Depiqmentierunqsmittel

Self-tanning is dihydroxyacetone. Suitable tyrosine inhibitors which prevent the formation of melanin and are used in depigmentation agents, for example, arbutin, kojic acid, coumaric acid and ascorbic acid (vitamin C) in question.

Hvdrotrope

To improve the flow behavior, hydrotropes, polyols such as ethanol, isopropyl alcohol, or the like. Polyols which are suitable here preferably have 2 to 15 carbon atoms and at least two hydroxyl groups. The polyols may contain other functional groups, especially amino groups, or be modified with nitrogen. Typical examples are

> Glycerol;

> Alkylene glycols such as ethylene glycol, diethylene glycol, propylene glycol, Butylengly- col, hexylene glycol and polyethylene glycols with an average molecular weight of 100 to 1,000 daltons;

> Technical oligoglycerol mixtures with a self condensation degree of 1, 5 to 10, for example technical diglycerol mixtures with a diglycerol content of 40 to 50 wt .-%;

> Methyolverbindungen, such as in particular trimethylolethane, trimethylolpropane, Trimethylolbu- tan, pentaerythritol and dipentaerythritol;

> Niedrigalkylglucoside, in particular those having 1 to 8 carbon atoms in the alkyl radical, for example methyl and butyl glucoside;

> Sugar alcohols having 5 to 12 carbon atoms, for example sorbitol or mannitol;

> Sugar having 5 to 12 carbon atoms, for example glucose or sucrose;

> Amino sugars, for example glucamine;

> Dialcohol amines, such as diethanolamine or 2-amino-1, 3-propanediol.

preservative

Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid and the other classes of compounds listed in B Annex 6, Part A and the cosmetics regulations are suitable. perfume oils

As perfume oils are mixtures of natural and synthetic fragrances. Natural fragrances are extracts from flowers (lily, lavender, rose, jasmine, neroli, ylang-ylang), stems and leaves (geranium, patchouli, petitgrain), fruits (anise, coriander, caraway, juniper), fruit peels (bergamot, lemon, orange), roots (mace, angelica, celery, cardamom, costus, iris, Calmus), woods (pinewood, sandalwood, guaiac wood, cedarwood, rosewood), herbs and grasses (tarragon, lemon grass, sage, thyme) needles and branches (spruce, fir, pine, dwarf pine), resins and balsams (galbanum, elemi, benzoin, myrrh, olibanum, opoponax). Animal raw materials in question, for example civet and beaver. Typical synthetic fragrance compounds are products of the ester, ether, aldehyde, ketone, alcohol and hydrocarbon type. Fragrance compounds of the ester type are benzyl acetate, phenoxyethyl isobutyrate, p-tert-butylcyclohexyl acetate, linalyl acetate, dimethyl benzyl, phenylethyl acetate, Linalyl benzoate, benzyl formate, Ethylmethylphenylglycinat, Allylcyclohexylpropio- nat, Styrallylpropionat and benzyl salicylate. The ethers include, for example, benzyl ethyl ether, the aldehydes include, for example, the linear alkanals having 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehyde, cyclamenaldehyde, hydroxycitronellal, lilial and bourgeonal, the ketones include the ionones, α-isomethylionone and methyl alcohols anethole, citronellol, eugenol, isoeugenol, geraniol, linalool, phenylethyl alcohol and Teφineol, and the hydrocarbons include mainly the terpenes and balsams. Preferably, however, mixtures of different odorants, which together produce a pleasing fragrance note. Essential oils of lower volatility, which are mostly used as aroma components, are also suitable as perfume oils, eg sage oil, chamomile oil, clove oil, melissa oil, mint oil, cinnamon leaf oil, lime blossom oil, juniper berry oil, vetiver oil, olibanum oil, galbanum, labolanum and lavender oil. Preferably, bergamot oil, dihydromyrcenol, lilial, lyral, citronellol, phenylethyl alcohol, α-hexylcinnamaldehyde, geraniol, benzyl acetone, cyclamen aldehyde, linalool, BOI sambrene Forte, Ambroxan, indole, hedione, Sandelice, lemon oil, mandarin oil, orange oil, lamylglycolat allyl, Cyclovertal , lavandin oil, muscatel sage oil, beta-damascone, geranium oil bourbon, cyclohexyl salicylate, Vertofix Coeur, Iso-e-Super, Fixolide NP, Evernyl, Iraldein gamma, phenylacetic sigsäure, geranyl acetate, benzyl acetate, rose oxide, romillat, irotyl and floramat alone or in mixtures.

dyes

The dyes suitable for cosmetic purposes, and authorized substances may be used as fuel Commission of the Deutsche Forschungsgemeinschaft, Verlag Chemie, Weinheim, 1984, S.81-106 are summarized, for example in the publication "Cosmetic coloring agents" of color. These dyes are normally used in concentrations of 0.001 to 0.1 wt .-%, based on the total mixture.

The total content of auxiliaries and additives can be 1 to 80, preferably 5 to 50 and especially 7 to 10 wt .-% - based on the preparation - be. The formulations may be produced by standard hot - or Heißemulgierungen or else according to the PIT method.

Examples

I. Preparation of acyl amino acids

Example 1: Preparation of Ci2-CI8-acyl glutamate-di-sodium salt without removal of the solvent

In a 15 m 3 reactor (Fig. 1) 1300 kg of water, 10 kmol = 1870 kg monosodium glutamate (x 1 H2O), 100 kg of isopropyl alcohol and 1100 kg presented 33% sodium hydroxide solution and stirred until a clear solution is formed. It is then cooled to 10 to 20 ° C. The reactor and the circuit are provided with a cooling jacket, which ensures the dissipation of the heat of reaction and a maximum temperature of 20 to 25 ° C ensured. The pH is adjusted to about 12 before the start of reaction with 11% sodium hydroxide solution. Subsequently, 7.7 kmol = 1825 kg Cocoylfettsäurechlorid simultaneously and 4500 kg 11% NaOH metered (see line concept) that the reactor temperature does not exceed 20 to 25 ° C and the pH-value of between 11 5 and 12.5. The dosage of the two reactants, preferably immersed in the sodium hydroxide solution in the reactor, ie, below the surface of the reaction mixture, and the acid chloride from the holding vessel at or before the mixer. A circulation pump ensures throughout the reaction for the circulation of the reaction mixture, wherein the rear vehicle of the mixture is immersed in the reactor, ie, below the surface of the reaction mixture. After addition of the fatty acid chloride is stirred in the reactor for about 2 hours at 20 to 25 ° C. and then heated for a further 2 hrs. At 60 to 80 ° C. Then allowed to cool to room temperature and the pH value of the reaction mixture by addition of dilute hydrochloric acid to about 10 a.

The content of Ci2-CI8-acyl glutamate disodium salt in the end product is 26%.

Example 2: Preparation of Ci2-CI8-acyl glutamate disodium salt without removal of the solvent

In a 15 m 3 reactor (Fig. 1) 1300 kg of water, 10 kmol = 1870 kg monosodium glutamate (1 x H2O), 135 kg of ethanol and 1100 kg presented 33% sodium hydroxide solution and stirred until a clear solution is formed. It is then cooled to 10 to 20 ° C. The reactor and the circuit are provided with a cooling jacket, which ensures the dissipation of the heat of reaction and a maximum temperature of 20 to 25 ° C ensured. The pH is adjusted to about 12 before the start of reaction with 11% sodium hydroxide solution. Subsequently, 7.7 kmol = 1825 kg Cocoylfettsäurechlorid simultaneously and 4500 kg 11% NaOH metered (see line concept) that the reactor temperature does not exceed 20 to 25 ° C and the pH-value of between 11 5 and 12.5. The dosage of the two reactants, preferably immersed in the sodium hydroxide solution in the reactor, ie, below the surface of the reaction mixture, and the acid chloride from the Voriagebehälter in or before the mixer. A circulation pump ensures throughout the reaction for the circulation of the reaction mixture, wherein the rear vehicle of the mixture is immersed in the reactor, ie, below the surface of the reaction mixture. After addition of the fatty acid chloride is stirred in the reactor for about 2 hours at 20 to 25 ° C. and then heated for a further 2 hrs. At 60 to 80 C. then allowed to cool to room temperature and the pH value of the reaction mixture through addition of dilute hydrochloric acid to about 10 degrees.

The content of Ci2-CI8-acyl glutamate disodium salt in the end product is 27.6%.

Example 3: Preparation of Ci2-CI8-acyl glutamate-di-sodium salt without removal of the solvent

In a 15 m 3 reactor (Fig. 1) 1300 kg of water, 10 kmol = 1870 kg monosodium glutamate (x 1 H2O), 160 kg Diethyenglykolmonoethylether and 1100 kg presented 33% sodium hydroxide solution and stirred until a clear solution is formed. It is then cooled to 10 to 20 ° C. The reactor and the circuit are provided with a cooling jacket, which ensures the removal of the reaction heat, and a maximum temperature of 20 to 25 carbon ensured. The pH is adjusted to about 12 before the start of reaction with 11% sodium hydroxide solution. Subsequently, 7.7 kmol = 1825 kg Cocoylfettsäurechlorid simultaneously and 4500 kg 11% NaOH metered (see line concept) that the reactor temperature does not exceed 20 to 25 ° C and the pH-value of between 11 5 and 12.5. The dosage of the two reactants, preferably immersed in the sodium hydroxide solution in the reactor, ie, below the surface of the reaction mixture, and the acid chloride from the Voriagebehälter in or before the mixer. A circulation pump ensures throughout the reaction for the circulation of the reaction mixture, wherein the rear vehicle of the mixture is immersed in the reactor, ie, below the surface of the reaction mixture. After addition of the fatty acid chloride is stirred in the reactor for about 2 hours at 20 to 25 ° C. and then heated for a further 2 hrs. At 60 to 80 ° C. Then allowed to cool to room temperature and the pH value of the reaction mixture by addition of dilute hydrochloric acid to about 10 a.

The content of Ci2-CI8-acyl glutamate disodium salt in the end product is 27.6%. Example 4: Preparation of Ci2-CI8-acyl glutamate-di-sodium salt with separation of the solvent

In a 15 m 3 reactor (Fig. 1) 1300 kg of water, 10 kmol = 1870 kg monosodium glutamate (x 1 H2O), 160 kg of isopropanol and 1100 kg presented 33% sodium hydroxide solution and stirred until a clear solution is formed. It is then cooled to 10 to 20 ° C. The reactor and the circuit are provided with a cooling jacket, which ensures the dissipation of the heat of reaction and a maximum temperature of 20 to 25 ° C ensured. The pH is adjusted to about 12 before the start of reaction with 11% sodium hydroxide solution. Subsequently, 7.7 kmol = 1825 kg Cocoylfettsäurechlorid simultaneously 4500 kg 11% NaOH metered (see line concept) that the reactor temperature does not exceed 20 to 25 ° C and the pH-value of between 11 5 and 12.5. The dosage of the two reactants, preferably immersed in the sodium hydroxide solution in the reactor, ie, below the surface of the reaction mixture, and the acid chloride from the Voriagebehälter in or before the mixer. A circulation pump ensures throughout the reaction for the circulation of the reaction mixture, wherein the rear vehicle of the mixture is immersed in the reactor, ie, below the surface of the reaction mixture. After addition of the fatty acid chloride is stirred in the reactor for about 2 hours at 20 to 25 ° C. and then heated for a further 2 hrs. At 60 to 80 C.

If desired, the pressure is reduced to 300 to 400 mbar and distilled at 60 to 80 ° C a mixture of isopropanol / water. To avoid concentrating the reaction mixture and to make distillation more effective, water vapor is dosed simultaneously. Here distill within an hour 1845 kg of isopropanol / water. The content of isopropanol is thereby reduced by 1, 5% to about 9 ppm.

The solution is adjusted, after cooling to room temperature with dilute hydrochloric acid to about pH = 10, and optionally adjusted by addition of water to the desired final concentration.

Example 5:

To the prepared according to Example 2 product is still 540 kg of propylene glycol-1, added the second Comparative Example 1: Preparation of Ci2-CI8-acyl glutamate-di-sodium salt

In a 15 m 3 reactor (Fig. 2), 2279 kg of water, 10 kmol = 1870 kg monosodium glutamate (1 x H2O) and 1870 kg presented 25% sodium hydroxide solution and stirred until a clear solution is formed. It is then cooled to 10 to 20 ° C. The reactor is provided with a cooling jacket, which ensures the dissipation of the heat of reaction and a maximum temperature of 20 to 25 ° C ensured. The pH is adjusted to about 12 before the start of reaction with 25% strength sodium hydroxide solution. Subsequently, 7.7 kmol = 1825 kg Cocoylfettsäurechlorid and 1540 kg 25% NaOH simultaneously metered in such that the reactor temperature does not exceed 20 to 25 ° C and the pH between 11 5 and 12.5. The dosage of the two reactants in the reactor is preferably immersed, ie below the surface of the reaction mixture. The reaction mixture is stirred with a Ikato Intermig stirrer at a speed of 120 / min intensive.

After dosing of 208 kg of acid chloride and 180 kg of 25% strength sodium hydroxide solution of the test should be discontinued, since the foam to the cover edge of the 15 m 3 reactor is (net capacity: 6407 kg).

Claims

claims
1. A process for the preparation of acylamino acids, in which into a reactor a mixture of at least one amino acid or its salt and an alkali source and that in or in front of a mixing element with fatty acid halides of the formula (I),
R 1 COX (I)
in which R 1 represents an alkyl or alkenyl group containing 6 to 22 carbon atoms and X is chlorine, bromine iodine, was added.
2. The method according to claim 1, characterized in that is used as the amino acids glutamic acid, sarcosine, aspartic acid, alanine, valine, leucine, isoleucine, proline, hydroxyproline, glycine, serine, cysteine, cystine, threonine, histidine and salts thereof.
3. Process according to claims 1 and / or 2, characterized in that carbonate as the alkali source in water and / or water-soluble organic solvents or dissolved alkali hydroxide, or amines, or using mixtures thereof.
4. A method according to any one of claims 1 to 3, characterized in that is used as the mixing element dynamic or static mixers.
5. A method according to any one of claims 1 to 4, characterized in that the reactor and the mixing element are connected to each other via a circulation system.
6. A method according to any one of claims 1 to 5, characterized in that it further presents water-soluble or water-dispersible organic solvent in the reactor, which are selected from the group formed by acetone, methyl ethyl ketone, dioxane, tetrahydrofuran, methanol, ethanol, propanol, i-propanol, butanol, t-butanol, penta nol, isopentanol, trimethylhexanol, glycerol, ethylene glycol, 2-methyl-propane-1, 3, propylene glycol, dipropylene glycol, 1, 3 butylene glycol, 1, 2-butanediol , 1, 4-butanediol, isopentyldiol, sorting Bitol, xylitol, mannitol, erythritol, pentaerythritol, ethanolamine, triethanolamine, 2-amino-2-methyl-propanol, 1-amino-2-propanol, 1-amino-butanol-2 , 1-methoxy-2-propanol, 2-methoxy ethanol, 2-ethoxyethanol, 2-propoxyethanol, 2-isopropoxyethanol, 2-butoxyethanol, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, 1 propoxy-2-propanol, 1-isopropoxy-2-propanol, 1-butoxy-2-propanol, 1 -lsobutoxy-2-propanol, methoxyisopropanol, diethylene colmonomethy- ether, diethylene glycol monoethyl ether, Diethylenglycolmonopropylether, Diethylenglycolmoni- sopropylether, diethylene glycol mono-butyl ether, triethylene glycol monomethyl ether, triethylene lenglycolmonoethylether, Triethylenglycolmonopropylether, Triethylenglycolmonisopropylether, triethylene glycol monobutyl ether, dipropylene glycol monomethyl ether, Dipropylenglycolmo- noethylether, Dipropylenglycolmonopropylether, Dipropylenglycolmonisopropylether, dipropylene lenglycolmonobutylether, hexylene glycol, triacetin, Propylenncarbonat, glycerol
7. A method according to any one of claims 1 to 6, characterized in that is not separated after the reaction of amino acids with fatty acid, the residual content of water-soluble or water-dispersible organic solvent.
8. A method according to any one of claims 1 to 7, characterized in that are mixed after the reaction of amino acids with fatty acid to the finished product of one or more of the following solvents: trimethylhexanol, glycerol, ethylene glycol, 2-methyl-propane-1, 3 , propylene glycol, dipropylene glycol, 1, 3 butylene glycol, 1, 2-butanediol, 1, 4-butanediol, isopentyldiol, sorbitol, xylitol, mannitol, erythritol, pentaerythritol, 1-methoxy-2-propanol, 2-methoxyethanol, 2-ethoxyethanol, 2-propoxyethanol, 2-lsopropoxye- THANOL, 2-butoxyethanol, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, 1-propoxy-2-propanol,
1-isopropoxy-2-propanol, 1-butoxy-2-propanol, 1-isobutoxy-2-propanol, methoxy isopropanol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, Diethylenglycolmonopropylether, Diethylenglycolmonisopropylether.Diethylenglycolmonobutylether, Triethylenglycolmo- monomethyl ether, triethylene glycol monoethyl ether, Triethylenglycolmonopropylether, triethylene lenglycolmonisopropylether, triethylene glycol monobutyl ether , Dipropylenglycolmonomethy- ether, dipropylene glycol monoethyl ether, Dipropylenglycolmonopropylether, dipropylene glycol monisopropylether, dipropylene glycol monobutyl ether, hexylene glycol,
9. Acylaminosäurezubereitungen containing,
(A) 3 to 10 wt.% Sodium chloride,
(B) 0.1 to 4 wt.% Free fatty acids,
(C) 1 to 11 wt.% Free amino acids,
(D) 0.1 to 6 wt.% Low molecular weight alcohol and
(E) 30 to 80 wt.% Water.
10. Use of acylamino acids according to claim 9 for use in cosmetics as well as in laundry detergents, dishwashing detergents and cleaners.
EP20020706698 2001-01-18 2002-01-09 Method for producing acyl amino acids Withdrawn EP1419137A2 (en)

Priority Applications (5)

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DE10102008 2001-01-18
DE10102008 2001-01-18
DE2001142469 DE10142469A1 (en) 2001-01-18 2001-08-31 Production of acylamino acids, useful in cosmetic products such as wash, rinse and cleaning agents, comprises reaction of an amino acid and an alkali source, prepared with a fatty acid halide
DE10142469 2001-08-31
PCT/EP2002/000123 WO2002057217A3 (en) 2001-01-18 2002-01-09 Method for producing acyl amino acids

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Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20040025904A (en) 2001-03-14 2004-03-26 브리스톨-마이어스 스큅 컴퍼니 Combination of epothilone analogs and chemotherapeutic agents for the treatment of proliferative diseases
DE10144264A1 (en) * 2001-09-08 2003-03-27 Cognis Deutschland Gmbh Aqueous detergent formulation, useful in cosmetics, e.g. shampoo, hair lotion, foam bath or shower formulation, contains N-acylamino-acid and/or salt and polyol and/or polyol fatty acid ester
US7545941B2 (en) * 2003-09-16 2009-06-09 Nokia Corporation Method of initializing and using a security association for middleware based on physical proximity
US6909721B2 (en) 2002-10-31 2005-06-21 Nokia Corporation Device detection and service discovery system and method for a mobile ad hoc communications network
US20050058109A1 (en) * 2003-09-16 2005-03-17 Jan-Erik Ekberg Mechanism for improving connection control in peer-to-peer ad-hoc networks
US7313120B2 (en) * 2003-09-16 2007-12-25 Nokia Corporation Application control in peer-to-peer ad-hoc communication networks
US7263345B2 (en) * 2004-03-17 2007-08-28 Nokia Corporation System and method for remote service information
US7697894B2 (en) * 2005-03-01 2010-04-13 Nokia Corporation Method and system for tactile confirmation of service bookmarks
US7359674B2 (en) * 2005-05-10 2008-04-15 Nokia Corporation Content distribution & communication system for enhancing service distribution in short range radio environment
US20060268896A1 (en) * 2005-05-31 2006-11-30 Sakari Kotola System and method for services functionality
DE102006038853A1 (en) 2006-08-18 2008-02-21 Clariant International Limited A process for preparing by means of direct oxidation acylglycinates
DE102007055265A1 (en) 2007-11-20 2009-05-28 Clariant International Ltd. A process for preparing acylglycinates
DE102008003825A1 (en) * 2008-01-10 2009-07-16 Clariant International Ltd. A process for preparing by means of direct oxidation acylglycinates
CN102126984B (en) * 2010-12-30 2014-10-01 上海奥利实业有限公司 Long chain acyl amino acid salt of N- condensation equipment and production process
DE102011107503A1 (en) * 2011-07-15 2012-03-01 Clariant International Ltd. Preparing acylglycinate compound useful in a composition, which is used as a surfactant in a cosmetic preparation, comprises reacting glycine with fatty acid chloride in water and in the presence of a basic alkali metal compound
US8697897B2 (en) * 2011-07-28 2014-04-15 Conopco, Inc. Method for preparing fatty acyl amido carboxylic acid based surfactants
US8853433B2 (en) 2011-07-28 2014-10-07 Conopco, Inc. General method for preparing fatty acyl amido based surfactants
US8822711B2 (en) 2011-07-28 2014-09-02 Conopco, Inc. Method for preparing fatty acyl amido carboxylic acid based surfactants
US8658589B2 (en) 2011-07-28 2014-02-25 Conopco, Inc. Fatty acyl amido based surfactant concentrates
US8981134B2 (en) 2011-07-28 2015-03-17 Conopco, Inc. Amino acid salt containing compositions
US8853447B2 (en) 2011-07-28 2014-10-07 Conopco, Inc. General method for preparing fatty acyl amido based surfactants
US8653018B2 (en) 2011-07-28 2014-02-18 Conopco, Inc. Fatty acyl amido based surfactant concentrates
GB201122220D0 (en) * 2011-12-23 2012-02-01 Croda Int Plc Novel emoillients
US9156777B2 (en) 2012-07-03 2015-10-13 Stepan Company Process for preparing N-acyl amino acid salts
CN102925122A (en) * 2012-11-22 2013-02-13 黄文章 Synthesis method of humic amide used for oil-based drilling fluid
CN103242206A (en) * 2013-05-30 2013-08-14 湖南众业科技实业有限公司 Production process for preparing fatty acyl-N-sodium methyl taurate surfactant
WO2015026538A1 (en) 2013-08-19 2015-02-26 Stepan Company Process for preparing n-acyl amino acid salts
CN103408449B (en) * 2013-08-21 2015-09-23 南京华狮化工有限公司 Preparing one kind n- acylamino acid or a salt thereof
KR101880791B1 (en) * 2015-10-08 2018-07-20 주식회사 엘지생활건강 Method for preparing N-acyl glycinate or salt thereof and use of composition for personal care products
KR101874024B1 (en) * 2016-06-29 2018-07-04 에이케이켐텍 주식회사 Manufacturing method of amino acid-based surfactant

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1165574B (en) 1960-08-08 1964-03-19 Dehydag Gmbh A process for producing for emulsifying ointment bases as serving mixed esters
DE2024051C3 (en) 1970-05-16 1986-05-07 Henkel Kgaa, 4000 Duesseldorf, De
LU68901A1 (en) 1973-11-30 1975-08-20
US4172887A (en) 1973-11-30 1979-10-30 L'oreal Hair conditioning compositions containing crosslinked polyaminopolyamides
DE4426216A1 (en) 1994-07-23 1996-01-25 Merck Patent Gmbh Benzylidenenorcamphor derivatives
DE4426215A1 (en) 1994-07-23 1996-01-25 Merck Patent Gmbh Ketotricyclo [5.2.1.0] decane derivatives
US5551301A (en) 1995-06-19 1996-09-03 Cardiometrics, Inc. Piezoresistive pressure transducer circuitry accommodating transducer variability
KR100437309B1 (en) 1995-07-12 2004-09-08 교와 핫꼬 고교 가부시끼가이샤 Detergent composition
DE19540645A1 (en) 1995-10-31 1997-05-07 Basf Ag Method and apparatus for the continuous preparation of N-acylamino carboxylic acids and N-acylamino sulfonic acids and their alkali metal salts
ES2188883T3 (en) 1996-07-08 2003-07-01 Ciba Sc Holding Ag Triazine derivatives as UV filter in sunscreen products.
JPH1081656A (en) 1996-09-06 1998-03-31 Ajinomoto Co Inc Production of n-long chain acyl acidic aminoacid or salts of the same
ES2246501T3 (en) 1996-11-29 2006-02-16 Basf Aktiengesellschaft Cosmetic and pharmaceutical preparations containing photostable UV-A.
DE69801383D1 (en) 1997-02-05 2001-09-27 Ajinomoto Kk A process for preparing N-long chain acyl-substituted acidic amino acids or salts thereof
FR2760746B3 (en) 1997-03-14 1999-05-21 Phytocos Lab new acylamino
DE19712033A1 (en) 1997-03-21 1998-09-24 Basf Ag Use of enamine derivatives as ultraviolet-A filters
DE19756377A1 (en) 1997-12-18 1999-06-24 Beiersdorf Ag Enhancing light protection factor of sun screen preparations containing UV filter compound
JP4392884B2 (en) * 1998-12-28 2010-01-06 旭化成ケミカルズ株式会社 N- long-chain acyl acidic amino acid salt, and a manufacturing method thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO02057217A2 *

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US20040063980A1 (en) 2004-04-01 application
WO2002057217A3 (en) 2004-03-25 application

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