DE19517048C1 - Use of quaternary aminoglycerin compounds - Google Patents

Abstract

Quaternary aminoglycerine compounds have formula (I), in which R<1>, R<2> and R<3> represent independently from each other hydrogen, an optionally hydroxy-substituted alkyl or aralkyl residue with 1 to 22 carbon atoms or a benzyl residue, and X stands for chloride or bromide. These compounds have brightening properties and are useful for preparing hair washing and hair care products.

Description

Field of the Invention

The invention relates to the use of quaternary aminoglycerin compounds available from Hy Drolysis of halogenated or epoxidized quaternary ammonium salts, for the production of hairline cleaning and maintenance products.

State of the art

A number of cationic surfactants have the property, both synthetic and kera to give tin fibers a pleasant soft feel while maintaining the electrostatic charge between the fibrils. For this reason, for example, quaternary ammo nium compounds of the distearyldimethylammonium chloride type as ingredients for hair care medium used, while other cationic surfactants such. B. the available on the chlorohydrin route and epoxypropyl and chlorohydroxypropylammonium salts known as quaternizing agents do not Show effect.

For a number of formulations, the application properties are those for the hair known products avivage not satisfactory. Accordingly, there is one in the market constant interest in new cationic surfactants that have at least equally good, preferably but have improved properties.  

The object of the invention was therefore to provide new cationic surfactants places that give the hair a pleasant soft feel, improve combability and the elec Reduce trostatic charge between the keratin fibers.

Description of the invention

The invention relates to the use of quaternary aminoglycerol compounds of the formula (I)

in which R¹, R² and R³ independently of one another for an optionally hydroxy substituted alkyl or aralkyl radical having 1 to 22 carbon atoms or a benzyl radical and X for Chloride or bromide is available for the production of hair cleaning and care products.

Surprisingly, it was found that the known quaternary aminoglycerol compounds have hair-activating and antistatic properties even if the quaternary stick Substituted only with short chain alkyl groups.

Quaternary aminoglycerol compounds

The quaternary aminoglycerol compounds to be used for the purposes of the invention have long been known substances of the prior art, even if their use for hair softening so far has not yet been considered. Descriptions of individual quaternary aminoglycerin ver Compounds that fall under the general formula (I) are, for example, the publications in Reports 32 750 (1899), Reports 33, 3500 (1900), Beilstein, Vol. 4 (Hw), 302 and (Erg), 841 remove. Further reference is made to the overviews in J. Org. Chem. 28, 2283 (1963), J. Chem. Soc. 890 (1950) and the publications CH-B 194 167, DE-AS 10 04 194, DE-A1 25 04 053, US 2,520,093 and US 2,876,217.  

To prepare the quaternary aminoglycerol compounds, the procedure is preferably such that quaternary ammonium salts of the formula (II)

in which R¹, R², R³ and X have the meanings given above and R⁴ for a 1,2-epoxypropyl or a 1-halo-2-hydroxypropyl group is subjected to basic hydrolysis. With the quar Tertiary ammonium salts, which are suitable as starting materials for the hydrolysis, are well-known substances, for example from Degussa AG Hanau / DE under the name QUAB® to be expelled. Quaternary ammonium salts of the formula (II) are preferably used in which

• - R¹, R² and R³ for methyl groups, R⁴ for a 1,2-epoxypropyl or 1-chloro-2-hydroxy propyl group and X represents chloride, or
• - R¹ and R² for methyl groups, R³ for an alkyl group having 12 to 18 carbon atoms or a benzyl group, R⁴ for a 1,2-epoxypropyl or 1-chloro-2-hydroxypropyl group and X for Bromide stands.

Hydrolysis of the quaternary ammonium salts, i.e. H. the ring opening of the epoxy compounds or the Hydrolysis of the halogen compounds takes place under basic conditions, preferably under one pH in the range from 9 to 13. It has proven to be advantageous to increase the hydrolysis Temperatures, for example at 50 to 98 ° C over a period of 1 to 48 and preferably 12 up to 36 hours. In the hydrolysis of the epoxy compounds, mass spectrometry copying studies in addition to the monomers of formula (I) also oligomers, in particular Dimers of the formula (III) are formed

in which R¹, R², R³ and X have the meanings given above and n for numbers from 2 to 10 and is preferably 2 to 5. If in the synthesis of the quaternary aminoglycerol compounds in addition to the monomers of the formula (I) and also oligomers of the formula (III), these are technical Mixtures expressly included in this teaching.

Industrial applicability

The quaternary aminoglycerin compounds according to the invention give hair, but also synthetic table fibers, a pleasant soft feel, improve dry and wet combability and reduce the electrostatic charge between the keratin fibers. They are therefore suitable for Manufacture of hair and personal care products and fabric softeners in which they are used in quantities from 1 to 50, preferably 2 to 15% by weight, based on the composition, can be present.

Hair cleaning and care products

The hair treatment agents can be added in minor amounts with the other ingredients contain compatible surfactants. Typical examples are fatty alcohol polyglycol ether sulfates, monoglyceride sulfates, mono- and / or dialkyl sulfosuccinates, fatty acid isethionates, fatty acid sarcosinates, fatty acid taurides, ether carboxylic acids, alkyl oligoglucosides, fatty acid glucamides, alkyl amido betaines and / or vegetable protein fatty acid condensates.

The hair treatment agents, such as hair shampoos, hair lotions or bubble baths, As further auxiliaries and additives, emulsifiers, superfatting agents, thickeners, Cation polymers, silicone compounds, biogenic agents, film formers, preservatives, dyes and Contain fragrances.

Non-ionic, ampholytic and / or hermaphrodite can be used as emulsifiers or co-emulsifiers Ionic surfactant compounds are used, which are preferred by a lipophilic linear alkyl or alkenyl group and at least one hydrophilic group. This hydro The phile group can be either an ionogenic or a nonionic group. Non-ionogenic Emulsifiers contain z as a hydrophilic group. B. a polyol group, a polyalkylene glycol ether group or a combination of polyol and polyglycol ether groups.  

Preferred agents are those which contain nonionic surfactants from at least one of the following groups as O / W emulsifiers: (a1) addition products of 2 to 30 mol of ethylene oxide and / or 0 to 5 mol of propylene oxide onto linear fatty alcohols having 8 to 22 carbon atoms , on fatty acids with 12 to 22 C atoms and on alkylphenols with 8 to 15 C atoms in the alkyl group; (a2) C _12/18 fatty acid _monoesters and diesters of adducts of 1 to 30 moles of ethylene oxide with glycerol; (a3) glycerol monoesters and diesters and sorbitan monoesters and diesters of saturated and unsaturated fatty acids having 6 to 22 carbon atoms and their ethylene oxide addition products; (a4) alkyl mono- and oligoglycosides with 8 to 22 carbon atoms in the alkyl radical and their ethoxylated analogues and (a5) addition products of 15 to 60 mol. ethylene oxide on castor oil and / or hardened castor oil; (a6) polyol and in particular polyglycerol esters such. B. polyglycerol polyricinoleate or polyglycerol poly-12-hydroxy stearate. Mixtures of compounds from several of these classes of substances are also suitable. The adducts of ethylene oxide and / or of propylene oxide with fatty alcohols, fatty acids, alkylphenols, glycerol mono- and diesters as well as sorbitan mono- and diesters of fatty acids or with castor oil are known, commercially available products. These are mixtures of homologs, their average degree of alkoxylation corresponds to the ratio of the amounts of ethylene oxide and / or propylene oxide and substrate with which the addition reaction is carried out. C _12/18 fatty acid _monoesters and diesters of adducts of ethylene oxide with glycerol are known from DE-PS 20 24 051 as refatting agents for cosmetic preparations. C _8/18 alkyl mono- and oligoglycosides, their preparation and their use as surface-active substances are, for example, from US 3,839,318, US 3,707,535, US 3,547,828, DE-OS 19 43 689, DE-OS 20 36 472 and DE-A1 30 01 064 and EP-A 0 077 167 are known. They are produced in particular by reacting glucose or oligosaccharides with primary alcohols with 8 to 18 carbon atoms. With regard to the glycoside residue, both monoglycosides in which a cyclic sugar residue is glycosidically bound 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. Furthermore, zwitterionic surfactants can be used as emulators. Zwitterionic surfactants are those surface-active compounds which carry at least one quaternary ammonium group and at least one carboxylate and one sulfonate group in the molecule. Particularly suitable zwitterionic surfactants are the so-called betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example the cocoalkyl-dimethylammonium glycinate, N-acyl-aminopropyl-N, N-dimethylammonium glycinate, for example the cocoacylaminopropyldimethylammonium glycinate, and 2-alkyl- 3-carboxyl-methyl-3-hydroxyethylimidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group and the coconut acylaminoethylhydroxyethylcarboxymethylglycinat. The 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 C _8/18 alkyl or acyl group, contain at least one free amino group and at least one -COOH or -SO₃H group in the molecule and are capable of forming internal salts. Examples of suitable ampholytic surfactants are N-alkylglycine, N-alkyl propionic acid, N-alkylaminobutyric acid, N-alkyliminodipropionic acid, N-hydroxyethyl-N-alkylamido propylglycine, N-alkyltaurine, N-alkyl sarcosine, 2-alkylaminopmpionic acid and alkylamino acetic acid with each about 8 to 18 carbon atoms in the alkyl group. Particularly preferred ampholytic surfactants are N-coconut alkyl amiriopropionate, coconut acyl aminoethyl aminopropionate and C _12/18 acyl sarcosine.

Possible W / O emulsifiers are: (b1) adducts of 2 to 15 mol of ethylene oxide with castor oil and / or hardened castor oil; (b2) _{partial esters} based on linear, branched, unsaturated or saturated C _12/22 fatty acids, ricinoleic acid and 12-hydroxystearic acid and glycerol, polyglycerol, pentaerythritol, dipentaerythritol, sugar alcohols (e.g. sorbitol) and polyglucosides (e.g. Cellulose); (b3) trialkyl phosphates; (b4) wool wax alcohols; (b5) polysiloxane-polyalkyl-polyether copolymers or corresponding derivatives; (b6) mixed esters of pentaerythritol, fatty acids, citric acid and fatty alcohol according to DE-PS 11 65 574 and (b7) polyalkylene glycols.

Substances such as polyethoxylated lanolin derivatives, Lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides are used, the latter also serving as foam stabilizers. Suitable thickeners are for example polysaccharides, especially xanthan gum, guar guar, agar agar, alginates and Ty loose, carboxymethyl cellulose and hydroxyethyl cellulose, also higher molecular weight polyethylene glycol colmono- and diesters of fatty acids, polyacrylates, polyvinyl alcohol and polyvinyl pyrrolidone, surfactants such as fatty alcohol ethoxylates with a narrow homolog distribution or alkyl oligoglu coside as well as electrolytes such as table salt and ammonium chloride.

Suitable cationic polymers are, for example, cationic cellulose derivatives, cationic Strong, copolymers of diallyl ammonium salts and acrylamides, quaternized vinyl pyrrolidone / Vinylimidazole polymers such as B. Luviquat® (BASF AG, Ludwigshafen / FRG), condensation products of polyglycols and amines, quaternized collagen polypeptides such as lauryldimonium hydroxypropyl hydrolyzed collagen (Lamequat®L, Grünau GmbH), polyethyleneimine, cationic sili conpolymers such as B. Amidomethicone or Dow Corning, Dow Corning Co./US, copolymers of Adi pinic acid and dimethylaminohydroxypropyldiethylenetrimamine (Cartaretine®, Sandoz / CH), polyamino polyamides such as B. described in FR A 22 52 840 and its crosslinked water-soluble poly  mer, cationic chitin derivatives such as quaternized chitosan, optionally micro crystalline, cationic guar gum such as B. Jaguar® CBS, Jaguar® C-17, Jaguar® C-16 the Celanese / US, quaternized ammonium salt polymers such. B. Mirapol® A-15, Mirapol® AD-1, Mira pol® AZ-1 from Miranol / US.

Suitable silicone compounds are, for example, dimethylpolysiloxanes, methylphenylpolysiloxanes, Cyclic silicones as well as amino, fatty acid, alcohol, polyether, epoxy, fluorine and / or alkyl modified Silicone compounds. Plant extracts and vita are examples of biogenic active ingredients to understand min complexes. Common film formers are, for example, chitosan, microcrystalline Chitosan, quaternized chitosan, polyvinylpyrrolidone, vinylpyrrolidone-vinyl acetate copolymers, poly mers of the acrylic acid series, quaternary cellulose derivatives, collagen, hyaluronic acid or their salts and similar compounds. Suitable preservatives are, for example, phenoxyethanol, Formaldehyde solution, parabens, pentanediol or sorbic acid. As pearlescent agents come for example as glycol distearic acid esters such as ethylene glycol distearate, but also fatty acid monoglycol esters in Be dress. Suitable dyes are those which are suitable and approved for cosmetic purposes are used, such as those in the publication "Cosmetic Colorants" of the color material commission of the German Research Foundation, Verlag Chemie, Weinheim, 1984, Pp. 81-106 are compiled. These dyes are usually used in concentrations of 0.001 up to 0.1 wt .-%, based on the total mixture used.

The total proportion of auxiliaries and additives can be 1 to 50, preferably 5 to 40% by weight on the middle - amount.  

Examples Manufacturing examples Manufacturing example H1

151 g (1 mol) epoxypropyltrimethylammonium chloride in 150 ml Was water dissolved and mixed with such an amount of concentrated aqueous sodium hydroxide solution that a pH of 11 was established. The mixture was heated to 70 ° C and over a period of Hydrolyzed for 24 h. The 1,2-dihydroxypropyltrimethylammonium chloride became practically quantitative Get yield.

Manufacturing example H2

Analogously to Example H1, 430 g of a 40% by weight aqueous solution of 3-chloro-2-hydroxy were propyldimethyldodecylammonium chloride hydrolyzed. Monomeric 1,2-diol and dimers were in Ge weight ratio of about 50:50 obtained.

II. Wet and dry combability

To determine the combability, the products according to the preparation examples H1 and H2 in following acidic formulations (pH value: 4) used (Table 1; percentages as wt .-%). The Recipes R1 and R2 are according to the invention, the recipe R3 (DSDMAC = distearyldimethylammo nium chloride) is used for comparison.  

Table 1

Recipe example

Wet combability

Wet combability was assessed on brown hair (Alkinco # 6634, strand length 12 cm, strand mass 1 g) examined. After the zero measurement, the strands were washed with 100 ml of For formulations A to J or U, V and W soaked. After a contact time of 5 minutes, the strands were 1 min rinsed under running water (1 l / min, 38 ° C). The strands were measured again and compared to the zero measurement. The error in the measurements was 2% on average, the statistical one Security was at least 99%. The results are shown in Table 2.

Dry combability

The dry combability was approved with the approval of the electrostatic Aufla dung examined. A relative humidity of 20% was set. The conditioning time was 12 h at 30 ° C. The measurement was carried out using the charge tapping on a double Faraday container fig after performing 10 combs. The average error in the measurements was 2.5% statistical certainty was at least 99.9%. The results of the combing work are also in Table 2 shown.

Electrostatic charge

The electrostatic charge was at 20% relative humidity measured. The results are summarized in Table 3.

A detailed description of the measurement methods can be found in J. Soc. Cosm. Chem., 24, 782 (1973).  

Table 2

Wet and dry combability

Table 3

Electrostatic charge

Application engineering example

Table 4

Hair cosmetics (water ad 100 wt .-%)

Claims (1)

Use of quaternary aminoglycerol compounds of the formula (I), in which R¹, R² and R³ independently represent an optionally hydroxy-substituted alkyl or aralkyl radical having 1 to 22 carbon atoms or a benzyl radical and X represents chloride or bromide, for the preparation of hair cleaning and care products.