EP3749280A1

EP3749280A1 - 1,2-diols for improving lather quality of cosmetic cleansing agents for skin and hair

Info

Publication number: EP3749280A1
Application number: EP19701533.2A
Authority: EP
Inventors: Catherine Weichold; Claus Nieendick; Andreas SCHWALLENBERG; Daniela Prinz; Monika Barbenheim; Ansgar Behler; Hans-Christian Raths
Original assignee: BASF SE
Current assignee: BASF SE
Priority date: 2018-02-07
Filing date: 2019-01-30
Publication date: 2020-12-16
Also published as: WO2019154674A1

Abstract

The invention relates to the use of specific 1,2-alkanediols as lather boosters in surfactant mixtures containing alkyl polyglycosides or derivatives of alkyl polyglycosides. In this way, mild cosmetic cleansing agents for skin and hair can be obtained.

Description

1, 2 diols for the foam improvement of cosmetic cleansers for skin and hair

The present invention relates to the use of one or more 1,2-alkanediols as foam improvers for alkyl and / or alkenyl oligoglycosides and / or their derivatives, where the alkyl and / or alkenyl oligoglycosides and / or their derivatives are alone or mixed with other surfactants may be present in a surfactant mixture. Another object of the present invention relates to a surfactant compound with 1, 2-alkanediols as foam improvers and alkyl and / or Alkenyloligoglykoside and / or derivatives thereof. Finally, the present invention also relates to cosmetic cleansers for skin and hair, which contain the 1, 2-alkanediols, for example in the form of the surfactant compounds of the invention, and methods for improving the foaming behavior of alkyl and / or Alkenyloligoglykosiden and / or their derivatives and a process for improving the foaming behavior of cosmetic cleaning agents, wherein the 1,2-alkanediols are added during their preparation, preferably in the form of a compound.

In the case of cosmetic products for the skin and hair, mainly personal cleansing such as hair shampoos or shower products, the consumer expects as much foam in a short time as often the cleaning performance is equated with the foaming power. In addition, a fine-pored foam when applied to the skin is perceived as pleasant and nourishing.

Detergents with a high foaming power are obtained when anionic surfactants such as fatty alcohol ether sulfates are used alone or else in combination with other surfactants.

In recent times, more and more cosmetic cleansing products for sensitive (head) skin in the market are in demand. For this field, the alkyl and / or Alkenyloligoglykoside from the group of nonionic surfactants are suitable because of their particularly mild character. However, cosmetic foams based solely on alkyl and / or alkenyl oligoglycosides as surfactants often do not meet the consumer's expectations in terms of their foaming behavior, in particular with regard to the amount of foam, intumescence and foam quality.

German Offenlegungsschrift DE 10 2007 028 509 discloses liquid detergents and cleaners which contain alkylpolyglucosides and, as "foam boosters", electrolytes selected from the group of the alkali metal, alkaline earth metal and / or ammonium compounds.

Document US 4,294,728 describes shampoo or foam bath compositions comprising an aqueous solution with at least one cationic, amphoteric or zwitterionic surfactant and at least one dihydric alcohol. These compositions may also contain nonionic surfactants such as ethoxylated and / or propoxylated fatty alcohols.

The document DE 931974 describes foaming-strong detergents and cleaners based on anionic with diols. In view of the known state of the art, there continues to be a need for mild cosmetic detergents and cleaners which exhibit improved foaming behavior. In particular, the cosmetic cleaners should be formable free from fatty alcohol ether sulfates (so-called "ether sulfates").

It was therefore a primary object of the present invention to provide skin and hair cosmetic cleaners based on the alkypolyglycosides or derivatives thereof which exhibit good foam volume and / or foaming power. Furthermore, it was an object of the present invention to improve the foam quality of the cosmetic cleaners so that the foam on the skin is perceived as pleasant and nourishing.

It has now surprisingly been found that the objects of the present invention can be achieved by the use of 1, 2 alkanediols of the formula (I),

R ¹ -CH (OH) -CH ₂ -OH (I) wherein R ^{1 is} a hydrocarbon radical having a total of 4 to 12 carbon atoms, as a foam improver for surfactant mixtures, the alkyl and / or Alkenyloligoglykoside and / or derivatives of alkyl and / or Alkenyl oligoglycosides included.

When using 1,2-alkanediols of the formula (I) according to the invention, an improved foam is made possible, whereby in the context of the invention foam improvement is understood to mean a foam reinforcement and / or a better foam quality.

For the purposes of the present invention is meant by the concept of foam reinforcement, the increase in the foam volume. Here again a distinction is made between the foaming volume and the foam volume over a longer period of time, the so-called foam stability. For the purposes of the present invention, the foaming behavior was determined as foam height after 10 seconds at 30 ° C., pH 5.5 with the stirring motor of the type "Eurostar 20 digital" from IKA-Werke GmbH & Co. KG equipped with a dispersion disk Z-disk, Diameter 6 cm. In the determination of the foaming behavior, an aqueous surfactant mixture with the identical surfactant, but without 1,2-alkanediol, served as comparison.

For the purposes of the present invention, the foam stability was measured as the foam height in cm after 20 or 80 seconds after the Sita test at 30 ° C., pH 5.5, 1300 revolutions per minute, based on the foam height of the same agent without 1,2-alkanediol , As a comparison served the same cosmetic detergent with identical ingredients in identical amounts, wherein the missing amount of 1, 2 alkanediol was balanced with water.

In the broadest sense, the term foam improvement also means the improvement of the foam quality, the aspect of the fine-poredness of the foam being particularly important (small air bubbles). Another aspect of the foam improvement is the velvety feeling on the skin subjectively evaluate subjects with grades.

For the purposes of the present invention, the term "compound" is understood to mean a prefabricated mixture of at least two constituents which can be used as a "premix" in the preparation of a final product. A surfactant compound contains one or more surfactants as one of at least two components in the compound. Alkanediols and surfactant mixture

The 1,2-alkanediols of the formula (I) used according to the invention can be used alone, i. a single 1,2-alkanediol is used, or a mixture of two or more 1,2-alkanediols of formula (I) is used, which mixture may contain any proportions of 1,2-alkanediols of formula (I).

Preference is given to using one or more 1,2-alkanediols of the formula (I) in which R ¹ denotes an unbranched hydrocarbon radical having 6 to 12 carbon atoms. For example, n-1, 2-octanediol, n-1, 2-decanediol and / or n-1, 2-dodecanediol are used.

Very particular preference is given to using the 1,2-alkanediol of the formula (I) in which R ¹ denotes an unbranched hydrocarbon radical having 6 carbon atoms, ie n-1, 2-octanediol.

Alkyl and / or alkenyl oligoglycosides are known nonionic surfactants which are obtained by the relevant processes of preparative organic chemistry and marketed, for example, on the market under the trade name Plantacare® by the Applicant.

According to one embodiment of the present invention, the 1,2-alkanediols are used for a surfactant mixture comprising alkyl and / or alkenyl oligoglycosides of the formula

(II)

R ² 0- [G] _p (II) in which R ^{2 is} an alkyl and / or alkenyl radical having 8 to 18 carbon atoms, G is a sugar radical having 5 or 6 carbon atoms and p is a number from 1 to 10 ,

The alkyl or alkenyl radical R ² can be derived from primary alcohols having 8 to 18, preferably primary, alcohols having 8 to 14 carbon atoms. Accordingly, the alkanediols are preferably used for surfactant mixtures which contain alkyl and / or alkenyl oligoglucosides of the formula (II) in which R ^{2 is} a C 8-14 -alkyl and / or alkenyl radical.

The alkyl and / or alkenyl oligoglycosides can be derived from aldoses or ketoses having 5 or 6 carbon atoms, preferably glucose. The preferred alkyl and / or alkenyl oligoglycosides are thus alkyl and / or alkenyl oligoglucosides. The index number p in the general formula (II) indicates the degree of oligomerization (DP), ie. H. the distribution of mono- and oligoglycosides and stands for a number between 1 and 10. While p in a given compound always has to be an integer, and here, above all, can assume the values p = 1 to 6, the value p for a determined alkyloligoglycoside an analytically determined computational size, which is usually a fractional number. Preference is given to using alkyl and / or alkenyl oligoglycosides having an average degree of oligomerization p of from 1.1 to 3.0. From an application point of view, those alkyl and / or alkenyl oligoglycosides whose degree of oligomerization is less than 1.7 and in particular between 1.2 and 1.4 are preferred.

The alkanediols are preferably used for surfactant mixtures which contain alkyl and / or alkynyl oligoglucosides of the formula (II) in which R ^{2 is} a C 8-14 -alkyl and / or alkenyl radical and G is a 6 carbon moiety and p is a number between 1, 2 and 1, 4.

Such alkyl polyglycosides are commercially available in liquid or pasty form, usually with an active substance content in the range of 40 to 60 wt .-%, for example under the trade name Plantacare® 1200 UP, Plantacare® 2000 UP, Plantacare® 810UP or Plantacare® 818UP at BASF.

According to a further embodiment of the present invention, the 1,2-alkanediols are used for surfactant mixtures containing alkyl and / or alkenyl oligoglycosyl carboxylates as derivatives of alkyl and / or alkenyl oligoglycosides according to the formula (III),

R ³ 0- [G] _P I- (CH ₂ 0CO M) I- ₃ (III) where R ^{3 is} an alkyl and / or alkenyl radical having 8 to 18 carbon atoms, G is a sugar radical having 5 or 6 carbon atoms and p1 represents numbers from 1 to 10 and the radical M selected from the group H, Li, Na, K, Ca / 2, Mg / 2, ammonium and alkanolamines is improved.

Alkyl and / or alkenyl oligoglycoside carboxylates are reaction products of alkyl and / or alkenyl oligoglycosides which are already known per se with W-halocarboxylic acids, their salts or esters, the preparation of which has been described, for example, in International Application W002 / 090369. Typically, an aqueous solution of alkyl and / or Alkenyloligoglycosiden, preferably Ci2 _{/ i} 6 -Alkylpolyglucoside, presented in a stirred vessel. This aqueous solution contains in particular 50 to 60 wt .-% alkyl and / or alkenyl oligoglycosides - based on the active ingredient content. Under nitrogen atmosphere, the solution is heated to 50 to 100, preferably 60 to 85 and in particular 80 ° C and then added alkali. In the context of the invention, alkali is understood as meaning solid alkali metal hydroxides or alkali metal carbonates or alkali metal hydroxide dissolved in water, preferably sodium hydroxide or alkali metal carbonate. Preferably, solid alkali hydroxide, in particular sodium hydroxide, such as NaOH prills used. After 1 to 4, preferably 1 hour stirring time (slight increase in temperature up to 90 ° C) is added with W-halocarboxylic acids, their salts or esters, preferably sodium chloroacetate (MCA), and stirred at 50 to 100, preferably 80 ° C. until complete implementation has taken place. The reaction control is carried out via the liberated amount of alkali metal halide, preferably sodium chloride. Typically, the alkyl and / or alkenyl oligoglycoside is reacted with sodium monochloroacetate (MCA) in a molar ratio of 1: 0.5 to 1: 1, 5 and preferably 1: 1 to 1: 1, 3.

After a reaction time of 2 to 8, preferably 3 to 6 and especially 3 to 5 hours, a yield of 30 to 100% alkyl and / or Alkenyloligoglycosidcarboxylaten of formula (III) based on the amount of alkyl and / or Alkenyloligoglycoside.

For the purposes of the present invention Alkyloligoglycosidcarboxylate of formula (III) are preferred in which R ^{3 is} a Ci2 _/ 16-alkyl radical and G is a sugar residue with 6 carbon atoms and p1 is a number between 1, 2 and 1, 4 and M is selected from the group H (hydrogen) and Na (sodium) and the group - (CH2OCOOM) is bound only once to the sugar residue. For the purposes of the present application, according to a further embodiment, the 1,2-alkanediols are used for surfactant mixtures which contain alkyl and / or alkenyl oligoglycosides of the formula (II) and alkyl and / or alkenyl oligoglycoside carboxylates of the formula (III) wherein R ² or R ³ , G and p and p1 and M have the meaning given above. Particularly suitable are surfactant mixtures containing alkyl and Alkenyloligoglykoside of formula (II) and Alkenyloligoglykosidcarboxylate of formula (III), wherein R ² and R ^{3 is} a Ci2-alkyl radical and G is a sugar residue with 6 carbon atoms and p and p1 for a number between 1, 2 and 1, 4, the group - (CH 2 OCOOM) of formula (III) is attached only once to the sugar residue and M is selected from the group H (hydrogen) and Na (sodium).

Surfactant mixtures of alkyl and / or alkenyl oligoglycosides of the formula (II) and their carboxylates of the formula (III) can be obtained by the controlled incomplete reaction in the above-described preparation of the alkyl and / or alkenyl oligoglycoside carboxylates of the formula (III) using W-halocarboxylic acids whose salts or esters are obtained.

These mixtures preferably contain from 5 to 70% by weight, in particular from 10 to 45% by weight, of alkyl and / or alkenyl oligoglycoside carboxylates of the formula (III) and from 5 to 50% by weight, in particular from 5 to 30% by weight. to alkyl and / or Alkenyloligoglykosid of formula (II) and optionally to 100 wt .-% missing balance of forming alkali halide and water, with an active ingredient content of 25-30 wt .-% is preferred.

Such surfactant mixtures are commercially available, for example, under the name Plantapon® LGC from BASF.

According to a further embodiment of the invention, the 1,2-alkanediols are used for a surfactant mixture consisting of alkyl and / or alkenyl oligoglycosides and / or derivatives of the alkyl and / or alkenyl oligoglycosides, preferably for a surfactant mixture consisting of alkyl and / or alkenyl oligoglycosides. and / or Alkenyloligoglykoside of formula (II) and alkyl and / or Alkenyloli- goglykosidcarboxylaten of formula (III), wherein R ² or R ³ , G and p and p1 and M have the meaning given above.

According to a further embodiment according to the invention, the 1, 2 alkanediols are used for containing a surfactant mixture

Alkyl and / or alkenyl oligoglycosides of the formula (II) and / or

Alkyl and / or Alkenyloligoglykosidcarboxylate of the formula (III), wherein R ² or R ³ , G and p and p1 and M have the meaning given above, and

additional additional surfactants, preferably further surfactants except ether sulfates.

These additional further surfactants may be anionic, nonionic, cationic and / or amphoteric in nature, with mild surfactants preferably being present, fatty alcohol ether sulfates not being present (so-called "ether sulfate-free surfactants").

Suitable additional surfactants may be:

Acylglutamates are known anionic surfactants which follow formula (IV), in which R ⁴ CO is a linear or branched acyl radical having 6 to 22 carbon atoms and 0 and / or 1, 2 or 3 double bonds and X is selected from the group H, Li, Na, K, Ca / 2, Mg / 2 , Ammonium and alkanolamines. They are prepared, for example, by Schotten-Baumann acylation of glutamic acid with fatty acids, fatty acid esters or chlorides. Sales products are available, for example, from Hoechst AG, Frankfurt / DE, BASF or Ajinomoto Co. Inc., Tokyo / JP. Typical examples of suitable acyl glutamates suitable for the purposes of the invention, anionic surfactants derived from fatty acids having 6 to 22, pre-located are derived preferably from 12 to 18 carbon atoms, such as C12 _/ 14 or Ci2 _{/ i} 8 coconut oil fatty - acid, lauric acid, myristic acid, palmitic acid and / or stearic acid. Particularly preferred are di-sodium-N-cocoyl and di-sodium-N-stearoyl-L-glutamate.

Betaines are known surfactants which are predominantly produced by carboxyalkylation, preferably carboxymethylation of aminic compounds. Preferably, the starting materials are condensed with halocarboxylic acids or their salts, in particular with sodium chloroacetate, wherein one mole of salt is formed per mole of betaine. Furthermore, the addition of unsaturated carboxylic acids, such as acrylic acid is possible. Examples of suitable betaines are the carboxyalkylation products of secondary and in particular tertiary amines which follow the formula (V),

in which R ^{5 is} alkyl and / or alkenyl radicals having from 6 to 22 carbon atoms, R ^{6 is} hydrogen or alkyl radicals having from 1 to 4 carbon atoms, R ^{7 is} or alkyl radicals having from 1 to 4 carbon atoms, n is from 1 to 6, and X is ^{1 is} selected from the group H, Li, Na, K, Ca / 2, Mg / 2, ammonium and alkanolamines. Typical examples are the carboxymethylation products of hexylmethylamine, hexyldimethylamine, octyldimethylamine, decyldimethylamine, dodecyl methylamine, dodecyl dimethylamine, Dodecylethylmethylamin, Ci2 _{/ i} 4-cocodimethylamine, Myristyldi- methylamine, cetyldimethylamine, stearyldimethylamine, stearyl amine Oleyldimethyl-, C16 / 18 tallow alkyl dimethyl amine as well as their technical mixtures.

Also suitable are carboxyalkylation products of amidoamines which follow the formula (VI),

in which R ^{8 is} CO for an aliphatic acyl radical having 6 to 22 carbon atoms and 0 or 1 to 3 double bonds, m is a number from 1 to 3 and R ⁶ , R ⁷ , n and X ² are the meanings of X ^{1 of} the formula given above (V) can have. Typical examples are reaction products of fatty acids having 6 to 22 carbon atoms, namely caproic, caprylic, capric, lauric, myristic, palmitic, palmitic, stearic, isostearic, oleic, elaidic, petroselic, linoleic, linolenic, elaeostearic, arachidic, gadoleic, , Behenic acid and erucic acid and their technical mixtures, with N, N-dimethylaminoethylamine, N, N-dimethylaminopropylamine, N, N-diethylaminoethylamine and N, N-diethylaminopropylamine, which are condensed with sodium chloroacetate. Preferably, the input rate of a condensation product of _{C8 / i8} coconut oil fatty acid-N, N-dimethylaminopropylamide with sodium chloroacetate is.

Surfactants selected from the group of amphoactetates may additionally be present. The term amphoacetates is understood to mean the carboxylation products of amidoamines.

Preferred amphoacetates follow the formula (VII),

CH2CH2OH

R ^{9 is} CO-NH- (CH ₂ ) ₂ -N- (CH ₂ ) ₂ COOX ³ (VII) in which R ⁹ CO is an aliphatic acyl radical having 6 to 22 carbon atoms and 0 or 1 to 3 double bonds and X ³ is selected from the group H, Li, Na, K, Ca / 2, Mg / 2, ammonium and alkanolamines.

Typical examples are reaction products of fatty acids having 6 to 22 carbon atoms, namely caproic, caprylic, capric, lauric, myristic, palmitic, palmitic, stearic, isostearic, oleic, elaidic, petroselic, linoleic, linolenic, elaeostearic, arachidic, gadoleic, behenic and Erucic acid and its technical mixtures, with aminoethylethanolamine (AEEA) and subsequent carboxylation with sodium chloroacetate. Preferred to use a condensation product is of Ce _{/ i} e coconut oil fatty acid with aminoethylethanolamine (AEEA) and subsequent carbonyl boxylierung with sodium chloroacetate.

Sulfosuccinates, also referred to as sulfosuccinic acid esters, are other additional anionic surfactants which can be obtained by the relevant methods of preparative organic chemistry. They follow the formula (VIII),

S03X ⁴

R ¹⁰ (OCH 2 CH 2) r OC-CH-CH ₂ -COO (CH ₂ CH ₂ O) s R ¹¹ (VIII) in the R ^{10 is} an alkyl and / or alkenyl radical having 6 to 22 carbon atoms, R ^{11 is} R ¹⁰ or X ⁴ , r and s is independently 0 or numbers from 1 to 10 and X ^{4 is} selected from the group H, Li, Na, K, Ca / 2, Mg / 2, ammonium and alkanolamines. Their preparation is usually carried out from maleic acid, but preferably maleic anhydride, which are esterified in the first step with optionally ethoxylated primary alcohols. At this point, the mono / diester ratio can be adjusted by varying the amount of alcohol and temperature. In the second step, the addition of bisulfite, which is usually carried out in the solvent methanol. Typical examples are sulfosuccinic acid mono- and / or diesters in the form of their sodium salts, which are derived from fatty alcohols having 8 to 18, preferably 8 to 10 or 12 to 14 carbon atoms; The fatty alcohols can be etherified with an average of 1 to 10 and preferably 1 to 5 moles of ethylene oxide and thereby have both a conventional and preferably a narrowed homolog distribution. Examples include di-n-octylsulfosuccinat and monolauryl-3EO-sulfosuccinate in the form of their sodium salts.

Also known as isethionates surfactants may be included as additional surfactants. They have the given formula (IX),

R ¹² -C00-CHR ¹³ -CHR ¹⁴ -SO ₃ X ⁵ (IX) where the radical R ^{12 is} a linear or branched alkyl or alkenyl radical having 7 to 19 C atoms and radicals R ¹³ or R ¹⁴ - independently of one another - hydrogen or an alkyl radical having 1 to 6 C atoms, with the proviso that not both radicals R ¹³ and R ¹⁴ denote an alkyl radical, and in which the radical X ^{5 is} selected from the group H, Li, Na, K, Ca / 2, Mg / 2, ammonium and alkanolamines.

The compounds can be prepared by all methods known to those skilled in the art. For example, by the direct condensation of a salt of isethionic acid with one or more fatty acid (s) or alternatively by indirect means in which first one or more fatty acid (s) in the fatty acid chloride form and then brought to the reaction with the salt of isethionic acid ,

In one embodiment, the proportion of the compounds in which the radical R ^{12 is} an alkenyl radical, based on the total amount of the compounds of the formula (IX), is 3% by weight or less.

In a preferred embodiment, the radical R ¹² in the formula (IX) is a saturated, linear alkyl radical having 1 1 to 17 C atoms, wherein the proportion of compounds of the formula (IX) in which the radical R ^{12 is} an undecyl and / or a tridecyl radical is, based on the total amount of the compounds of formula (IX) - at 70 wt .-% or more and especially at 90 wt .-% or more.

In a preferred embodiment, the radical R ¹³ or R ^{14 is} a methyl or ethyl radical.

Preferably, the radical X ⁵ in the formula (II) is selected from the group H (hydrogen), Na (sodium) and NH ₄ (ammonium).

In addition, suitable additional surfactants are compounds of the formula (X) which are referred to as alpha-sulfofatty acid disalts in the context of the present invention, are for the aqueous surfactant compositions according to the invention obligatory. They have the formula given above (X),

R ¹⁵ CH (S0 ₃ M ¹ ) C00M ² (X) wherein the radical R ^{15 is} a linear or branched alkyl or alkenyl radical having 6 to 18 carbon atoms and the radicals M ¹ and M ² - independently selected - are selected from the group H, Li, Na, K, Ca / 2, Mg / 2, ammonium and alkanolamines. Particularly preferred alkanolamines are monoethanolamine, diethanolamine, triethanolamine and mono-isopropanolamine.

In one embodiment, the proviso that the proportion of compounds (X) in which the radical R ^{15 is} an alkenyl radical, based on the total amount of the compounds (X) - is 3% by weight or less.

In a preferred embodiment, the radical R ¹⁵ in the formula (X) is a saturated, linear alkyl radical having 10 to 16 C atoms, wherein the proportion of the compounds (X) in which the radical R ^{15 is} a decyl and / or a Dodecyl is - based on the total amount of the compounds (X) - at 70 wt .-% or more and preferably at 90 wt .-% or more.

Preferably, the radicals M ¹ and M ² in the formula (X) are selected from the group H (hydrogen) and Na (sodium).

The compounds (X) can be prepared by all methods known to the person skilled in the art. A particularly preferred method of preparation is the sulfonation of the corresponding carboxylic acids. In this case, the corresponding carboxylic acids and in particular the corresponding fatty acids are reacted with gaseous sulfur trioxide, the sulfur trioxide preferably being employed in an amount such that the molar ratio of SO ₃ to fatty acid in the range from 1.0: 1 to 1.1: 1 lies. The crude products thus obtained, which are acid sulfonated products, are then partially or completely neutralized, with complete neutralization with aqueous NaOH being preferred. If desired, it is also possible to carry out cleaning steps and / or bleaching (to set the desired light color of the products).

Accordingly, according to one embodiment, the 1,2-alkanediols are used for surfactant mixtures which comprise further surfactants, preferably further surfactants except ether sulfates and preferably further surfactants of the formulas (IV) to (X) and in particular further surfactants selected from those of acylglutamates , Betaines, sulfosuccinates, amphoacetates, amidoamines, isethionates and alpha-sulfofatty acid disalts.

Preferably, the 1,2-diols of formula (I) are used for a surfactant mixture consisting essentially of

Alkyl and / or Alkenyloligoglykosiden of the formula (II) and / or of alkyl and Alkenyloli- goglykosidcarboxylate of the formula (III) or for

Alkyl and / or Alkenyloligoglykosiden of the formula (II) and / or of alkyl and Alkenyloli- goglykosidcarboxylate of the formula (III) and additional surfactants selected from the Acylglutamates, betaines, sulfosuccinates, isethionates, alpha sulfo fatty acid salts and / or amphoacetates.

For the embodiment of the surfactant mixtures, the 1,2-alkanediols are preferably used for surfactant mixtures which are used in amounts of from 10 to 50, preferably from 20 to 40,% by weight of alkyl and / or alkenyl oligoglycosides and / or derivatives of alkyl and / or Alkenyloligoglycosides and in amounts of 50 to 90 wt .-%, preferably 60 to 80 wt .-% of other surfactants selected from those of acylglutamates, betaines, sulfosuccinates, isethionates, alpha-sulfofatty acid disalts and / or amphoacetates formed Group, wherein the wt .-% based on the active contents are ..

The additional additional surfactants are preferably free of ethylene oxide adducts.

The 1,2-diols of the formula (I) are preferably in a weight ratio of 1:10 to 10: 1, preferably 1: 7 to 7: 1, based on the active content of alkyl and / or alkenyl oligoglycosides and / or their derivatives in the surfactant mixture - used. The amount used is based on the amount of active substance in alkyl and alkenyl oligoglycosides and / or derivatives thereof, even if additional additional surfactants of the type described are present.

The use according to the invention of the diols of the formula (I) leads to an increase in the foam volume of surfactant mixtures or of detergents which contain this surfactant mixture. The foaming behavior of the surfactant mixture is preferably measured as foam height after 10 seconds at 30 ° C., pH 5 , 5 with the stirring motor of the type "Eurostar 20 digital" IKA-Werke GmbH & Co KG equipped with a disc Z disk, diameter 6 cm by at least 15%, preferably improved by 30% up to 80% - based on the Foam height of the same surfactant mixture without 1, 2 alkane diol.

Another object of the present invention relates to a surface-active compound with improved foam consisting of 1, 2 alkanediols of the formula (I) and alkyl and / or Alkenyloli goglykosiden and / or derivatives thereof, preferably from alkyl and / or Alkenyloligoglykosiden the formula (II) and / or alkyl and Alkenyloligoglykosidcarboxylaten of formula (III), wherein R ² or R ³ , G and p and M have the meaning given above in the formulas. See also the meaning in the formulas according to claim 3,4 and / or 5.

Another object of the present invention relates to a surface-active compound with improved foam consisting of

1, 2 alkanediols according to the definition of claim 1 or and

Alkyl and / or alkenyl oligoglycosides and / or derivatives thereof, in particular of the formula

(II) and / or (III) and

additionally selected further surfactants, preferably excluding ether sulfates and preferably further surfactants of the formulas (IV) to (X) and in particular further surfactants from the group formed by acylglutamates, betaines, sulfosuccinates, amidoamines, isethionates, amphoacetates and alpha-sulfofatty acid disalts.

The surface-active compounds according to the invention consist essentially of the alkanediols and the surfactants of the type described as active substance, but may have water or impurities due to the preparation of the compounds described or else preservatives or other constituents which are immaterial to the invention.

In the preferred surfactant compounds according to the invention, essentially 1,2-diols of the formula (I) are present in a weight ratio of from 1:10 to 10: 1, preferably from 1: 7 to 7: 1, based on the active content of alkyl groups. and / or alkenyl oligoglycosides and / or derivatives thereof in the surfactant mixture.

The surface-active compounds according to the invention can be obtained by stirring the individual constituents, with the 1,2-alkanediols of the formula (I) preferably being stirred into the alkyl and alkenyl oligoglycosides and / or their derivatives at room temperature. In general, the alkyl and alkenyl oligoglycosides and / or their derivatives are in commercial form, i. as an aqueous formulation.

Another object of the present invention relates to cosmetic cleansers for skin and hair, the 1, 2 alkanediols of the type described for improving the Schaumverhal- of alkyl and / or Alkenyloligoglykoside and / or derivatives thereof, preferably in a weight ratio of 1: 10 to 10: 1, preferably 1: 7 to 7: 1, - based on the active content of alkyl and / or alkenyl oligoglycosides and / or derivatives thereof in the surfactant mixture - contained.

The cosmetic cleaners can contain the 1,2-alkanediols of the formula (I) and alkyl and alkenyl oligoglycosides and / or derivatives thereof as individual constituents or as a ready-made compound.

According to one embodiment, the cosmetic cleaning agent may be the compound according to the invention consisting of 1, 2 alkanediols of the formula (I) and also alkyl and / or alkenylologlycosides and / or derivatives thereof, preferably of the formula (II) and / or of the formula ( III), wherein R ² or R ³ , G and p with the meanings given above, included. In the context of this embodiment, it is preferred if the cosmetic cleaning agent contains, in addition to the compound, further additional surfactants, preferably those which have already been described as further surfactants in connection with the surfactant mixtures. Accordingly, according to this embodiment, the cleaning agents according to the invention contain further surfactants, preferably excluding ether sulfates and preferably contain as additional surfactants those of the formula (IV) to (X) and in particular those selected from acylglutamates, betaines , Sulfosuccinates, amidoamines, isethionates, alpha sulfo fatty acid salts and amphoacetates.

According to another embodiment, the cosmetic cleaning agent may also contain a compound according to the invention which, in addition to 1, 2 alkanediols of the formula (I) and alkyl and / or alkenyl oligoglycosides and / or derivatives thereof, preferably of the formula (II) and / or of the formula (III), additionally containing further surfactants, preferably those already described in connection with the surfactant mixtures as further surfactants. Accordingly, according to this embodiment, the cleaning agents according to the invention comprise a compound containing further surfactants, preferably excluding ether sulfates and preferably those of the formula (IV) to (X) and especially those selected from acylglutamates, betaines, sulfosuccinates, amidoamines, Isethionates, alpha-sulfofatty acid disalts and amphoacetates.

In other words, the cleaning agents according to the invention may contain the individual constituents (1, 2 alkanediol and surfactant mixture) or the prefabricated compound, wherein the additional further surfactants may likewise be contained as individual constituents or already prefabricated in the compound in the cleansing compositions.

Accordingly, further embodiments relate to cosmetic cleaning agents according to patent claims 14 and 17, respectively.

The compounds according to the invention are preferably present in the cosmetic cleansing compositions according to the invention in amounts of from 0.1 to 35% by weight.

Both cosmetic cleansing compositions for skin and hair according to the invention have the foam volume improved, and the foam stability is improved by at least 25%, preferably by 30 to 100%, based on the same cosmetic cleanser without 1,2-alkanediol, the foam stability being measured was measured as foam height in cm after 20 seconds according to the Sita test at 30 ° C., pH 5.5, 1300 revolutions per minute.

The same cosmetic cleanser used as a comparison has identical ingredients in identical amounts; only the water content is different, to compensate for the missing amount of 1, 2 alkane diol.

Another object of the present invention relates to a method for improving the foaming behavior of alkyl and / or Alkenyloligoglykosiden and / or derivatives thereof, characterized in that one, 1, 2 alkanediols of the formula R ¹ -CH (OH) -CH 2 -OH (I), wherein R ^{1 is} a hydrocarbon radical having a total of 4 to 12 carbon atoms, preferably an unbranched hydrocarbon radical having 6 to 12 and in particular a straight-chain hydrocarbon radical having 6 carbon atoms added.

Another object of the invention relates to a method for improving the foam behavior of alkyl and / or alkenyl oligoglycosides and / or their derivatives containing cosmetic cleaning agents, characterized in that 1, 2 alkanediols of the formula R ¹ - CH (OH) - CH 2 -OH (I) in which R ^{1 is} a hydrocarbon radical having a total of 4 to 12 carbon atoms, preferably an unbranched hydrocarbon radical having 6 to 12 and in particular an unbranched hydrocarbon radical having 6 carbon atoms, in the preparation of the cosmetic cleaning agent are added, preferably in the form of a surface-active compound according to claim 12 or 13.

It should be emphasized that the effect of 1, 2 alkanediols of formula (I) is still observed in the formulated detergents. As a rule, cosmetic cleansers for the skin and hair contain other ingredients. This is also possible with the cosmetic cleansing compositions according to the invention.

The following are typical other ingredients for skin and hair cleansers:

emulsifiers

Suitable emulsifiers are one or more of the following compounds:

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

Adducts of 1 to 15 moles of ethylene oxide with castor oil and / or hydrogenated castor oil;

Addition products of 15 to 60 moles of ethylene oxide with castor oil and / or hydrogenated castor oil;

Adducts with 1 to 30 moles of ethylene oxide on partial esters of glycerol and / or sorbitan with unsaturated, linear or saturated, branched fatty acids containing 12 to 22 carbon atoms and / or hydroxycarboxylic acids having 3 to 18 carbon atoms;

Partial esters of polyglycerol (average intrinsic condensation degree 2 to 8), polyethylene glycol (molecular weight 400 to 5000), sorbitan, trimethylolpropane, pentaerythritol, sugar alcohols (eg sorbitol), alkylglucosides (eg methylglucoside, butylglucoside, laurylglucoside) and polyglucosides ( 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 their adducts with 1 to 30 moles of ethylene oxide;

Mixed esters of pentaerythritol, fatty acids, citric acid and fatty alcohol and / or mixtures 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 their salts;

• wool wax alcohols;

Polysiloxane-polyalkyl-polyether copolymers or corresponding derivatives;

Block copolymers e.g. Polyethylene glycol-30 dipolyhydroxystearates;

Polymer emulsifiers, eg Pemulen types (TR-1, TR-2) from Goodrich; • Polyalkylene glycols as well

• Glycerine carbonate.

Particularly preferred emulsifiers are adducts of ethylene oxide with C12 _/ e-fatty acid mono- and diesters, addition products of 1 to 30, preferably 5 to 10 moles of ethylene oxide with hydroxystearic acid monoglyceride, hydroxystearic acid diglyceride, isostearic acid monoglyceride, isostearic acid diglyceride, oleic acid monoglyceride, oleic acid diglyceride , Ricinoleic acid moglyceride, ricinoleic acid diglyceride, linoleic acid monoglyceride, linoleic acid diglyceride, linolenic acid monoglyceride, linolenic acid diglyceride, erucic acid monoglyceride, erucic acid diglyceride, tartaric acid glyceride, tartaric acid diglyceride, citric acid monoglyceride, citron diglyceride, malic acid monoglyceride, malic acid diglyceride and technical mixtures thereof. Also suitable are addition products of 1 to 30, preferably 5 to 10 moles of ethylene oxide with sorbitan esters. As sorbitan sorbitan, sorbitan sesquiisostearate, sorbitan diisostearate, sorbitan triisostearate, sorbitan monooleate, sorbitan dioleate, trioleate, Sorbitanmonoerucat, Sorbitansesquierucat, Sorbitandierucat, Sorbitantrierucat, Sorbitanmonori- come cinoleat, Sorbitansesquiricinoleat, Sorbitandiricinoleat, Sorbitantriricinoleat, Sorbitanmonohydro- xystearat, Sorbitansesquihydroxystearat, Sorbitandihydroxystearat, Sorbitantrihydroxystearat , Sorbitan monotartrate, sorbitan sesquivar tartrate, sorbitan ditartrate, sorbitan tritartrate, sorbitan monocitrit, sorbitan siccitrate, sorbitan di-citrate, sorbitan tricitrate, sorbitan monomaleate, sorbitan sesqui-maleate, sorbitan dimaleate, sorbitan trimaleate and their technical mixtures. Typical examples of suitable polyglycerol esters are polyglyceryl-2 dipolyhydroxystearates (Dehyuls® PGPH), polyglycerol-3-diisostearates (Lameform® TGI), polyglyceryl-4 isostearates (Isolan® Gl 34), polyglyceryl-3 oleates, diisostearoyl Polyglyceryl-3 diisostearate (Isolan® PDI), polyglyceryl-3 methylglucose distearate (Tego Care® 450), polyglyceryl-3 beeswax (Cera Belina®), polyglyceryl-4-caprate (polyglycerol caprate T2010 / 90), polyglyceryl- 3 Cetyl ether (Chimexane® NL), polyglyceryl-3 distearate (Cremophor® GS 32) and polyglyceryl polyricinoleate (Admul® WOL 1403) polyglyceryl dimerate isostearate and mixtures thereof. Examples of other suitable polyol esters are the mono-, di- and triesters of trimethylolpropane or pentaerythritol with lauric acid, coconut fatty acid, tallow fatty acid, palmitic acid, stearic acid, oleic acid, behenic acid and the like, which are optionally reacted with from 1 to 30 mol of ethylene oxide. Trimethylpropane EO / PO trioleate is also preferred, a mixture obtainable by the reaction of trimethylolpropane trioleate with ethylene oxide and propylene oxide under alkaline conditions. In this case, at least in part, an incorporation of the ethylene oxide units (EO) and the propylene oxide units (PO) into the ester groups of the trimethylolpropane trioleate takes place. The trimethylpropane-EO / PO trioleate is characterized by its content of EO and PO units per molecule on a statistical average. In one embodiment of the present invention trimethyl propane EO / PO trioleate, with 120 ethylene oxide units (EO) and 10 propylene oxide units (PO) is used. Waxes and pearlescent waxes

Pearlescent waxes give the cosmetic preparations a white-shimmering, pearl-like effect, which is especially appreciated in shampoos and shower gels. However, waxes without pearlescent effect can also be contained in the hair treatment compositions.

Suitable wax bodies are: alkylene glycol esters, fatty acid alkanolamides, partial glycerides, esters of polybasic, optionally hydroxy-substituted carboxylic acids, fatty alcohols, fatty ketones, fatty aldehydes, fatty ethers, fatty carbonates, ring-opening products of olefin epoxides and mixtures thereof.

Consistency and thickener

As consistency factors are primarily fatty alcohols or hydroxy fatty alcohols having 12 to 22 and preferably 16 to 18 carbon atoms and in addition partial glycerides, fatty acids or hydroxy fatty acids into consideration. Preference is given to a combination of these substances with alkyl oligoglucosides and / or fatty acid N-methylglucamides of the same chain length and / or polyglycerol poly-12-hydroxystearates. Suitable thickeners are, for example, Aerosil types (hydrophilic silicas), polysaccharides, in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl and hydroxypropyl cellulose, and also higher molecular weight polyethylene glycol mono- and diesters of fatty acids , Polyacrylates, (eg Carbopol® and Pemulen types from Goodrich, Synthalene® from Sigma, Keltrol types from Kelco, Seppic types from Seppic, Salcare types from Allied Colloids), polyacrylamides, polymers, polyvinyl alcohol and polyvinylpyrrolidone. Bentonites, such as e.g. Bentone® Gel VS-5PC (Rheox), which is a mixture of cyclopentasiloxane, disteardimonium hectorite and propylene carbonate. Also suitable are surfactants, for example ethoxylated fatty acid glycerides, esters of fatty acids with polyols, for example pentaerythritol or trimethylolpropane, fatty alcohol ethoxylates with concentrated homologue distribution or alkyl oligoglucosides, and also electrolytes, such as common salt and ammonium chloride.

superfatting

Superfatting agents which can be used are substances such as lanolin and lecithin, as well as polyethoxylated or acylated lanolin and lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides, the latter also serving as foam stabilizers.

stabilizers

As stabilizers metal salts of fatty acids, such as magnesium, aluminum and / or zinc stearate or ricinoleate can be used. polymers

The presence of at least one cationic polymer is advantageous, preferably from the group of cationically modified cellulose derivatives, PQ 10, PQ 67, cationically modified guar derivatives such as Dehyquart® guar N, guar hydroxypropyltrimonium chloride, cationic homo- or copolymers based on acrylamide, cationic homo or copolymers based on vinylpyrrolidone, cationic homo- or copolymers based on quaternized vinylimidazole and cationic homo- or copolymers based on methacrylates.

Suitable cationic polymers are, for example, the quaternized hydroxyethylcellulose, which is also available under the name Polymer JR 400® from Amerchol, cationic starch, copolymers of diallylammonium salts and acrylamides, quaternized vinylpyrrolidone / vinylimidazole polymers, such as e.g. Luviquat® (BASF), condensation products of polyglycols and amines, quaternized protein hydrolysates, polypeptides and amino acids such as lauryldimonium hydroxypropyl hydrolyzed collagen (Lamequat®L / Grünau), quaternized wheat polypeptides, polyethylenimine, cationic silicone polymers, e.g. Amidomethicones, copolymers of adipic acid and dimethylaminohydroxypropyldiethylenetriamine (Cartaretine® / Sandoz), copolymers of acrylic acid with dimethyldiallylammonium chloride (Merquat® 550 / Chemviron), polyamino-polyamides, such as e.g. described in FR-A 2252840 and their crosslinked water-soluble polymers, cationic chitin derivatives such as quaternized chitosan, optionally microcrystalline distributed, condensation products of dihaloalkylene, such as. Dibromobutane with bis-dialkylamines, e.g. Bis-dimethylamino-1,3-propane, cationic guar gum, e.g. Jagar® CBS, Jaguar® C-17, Jaguar® C-16 from Celanese, quaternized ammonium salt polymers, such as ammonium chloride. Mirapol® A-15, Mirapol® AD-1, Mirapol® AZ-1 from Miranol. In particular, suitable cationic polymers are Polyquaternium-68, available as Luviquat® Supreme AT 1, or Polyquaternium-11, available as Luviquat® PQ 11 AT 1.

The cationic polymers are preferably present in the hair treatment compositions in amounts of from 0.02 to 5% by weight, preferably from 0.05 to 3% by weight and more preferably in amounts of from 0.1 to 2% by weight.

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 their esters, uncrosslinked polyols crosslinked with polyols, acrylamidopropyltrimethylammonium chloride / Acrylate copolymers, octylacrylamide / methyl methacrylate / tert-butylaminoethyl methacrylate / 2-hydroxypropyl methacrylate copolymers, polyvinylpyrrolidone, vinylpyrrolidone / vinyl acetate copolymers, vinylpyrrolidone / dimethylaminoethyl methacrylate / vinylcaprolactam terpolymers and optionally derivatized cellulose ethers and silicones. silicone compounds

Suitable silicone compounds are, for example, dimethylpolysiloxanes, methylphenylpolysiloxanes, cyclic silicones and also amino, fatty acid, alcohol, polyether, epoxy, fluorine, glycoside and / or alkyl-modified silicone compounds which may be both liquid and resin-form at room temperature. Also suitable are simethicones, which are mixtures of dimethicones having an average chain length of from 200 to 300 dimethylsiloxane units and hydrogenated silicates.

UV light protection filters

By UV sun protection factors are meant, for example, liquid or crystalline organic substances present at room temperature (light protection filters) which are capable of absorbing ultraviolet rays and of absorbing the absorbed energy in the form of longer-wave radiation, e.g. Heat again. UVB filters can be oil-soluble or water-soluble. As oil-soluble substances are e.g. to call:

3-benzylidene camphor or 3-benzylidene norcamphor and its derivatives, e.g. 3- (4-methylbenzylidene) camphor described;

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

Esters of cinnamic acid, preferably 4-methoxycinnamic acid 2-ethylhexyl ester, 4-methoxycinnamic acid propyl ester, 4-methoxycinnamic acid isoamyl ester 2-cyano-3,3-phenylcinnamic acid 2-ethylhexyl ester (octocrylene);

Esters of salicylic acid, preferably salicylic acid 2-ethylhexyl ester, salicylic acid 4-isopropylbenzyl ester, salicylic acid homomenthyl ester;

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

Esters of benzalmalonic acid, preferably di-2-ethylhexyl 4-methoxybenzmalonate;

T riazine derivatives, e.g. 2,4,6-trianilino (p-carbo-2'-ethyl-1'-hexyloxy) -1, 3,5-triazine and octyl triazone or dioctyl butamido triazone (Uvasorb® HEB);

Propane-1,3-diones, e.g. 1- (4-tert-butylphenyl) -3- (4'-methoxyphenyl) propane-1,3-dione;

• Ketotricyclo (5.2.1.0) decane derivatives.

Suitable water-soluble substances are:

2-phenylbenzimidazole-5-sulfonic acid and its alkali, alkaline earth, ammonium, alkylammonium, alkanolammonium and glucammonium salts;

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

Sulfonic acid derivatives of the 3-benzylidene camphor, e.g. 4- (2-oxo-3-bomylidenemethyl) benzene sulfonic acid and 2-methyl-5- (2-oxo-3-bomylidene) sulfonic acid and salts thereof.

As typical UV-A filter, in particular derivatives of benzoylmethane are suitable, such as, for example, 1- (4'-tert-butylphenyl) -3- (4'-methoxyphenyl) propane-1,3-dione, 4-tert. butyl-4'-methodological xydibenzoylmethane (Parsol® 1789), 1-phenyl-3- (4'-isopropylphenyl) -propane-1, 3-dione and enamine compounds. The UV-A and UV-B filters can of course also be used in mixtures. Particularly favorable combinations consist of the derivatives of the benzoylmethane, for example 4-tert-butyl-4'-methoxydibenzoylmethane (Parsol® 1789) and 2-cyano-3,3-phenylcinnamic acid 2-ethylhexyl ester (octocrylene). in combination with esters of cinnamic acid, preferably 4-methoxycinnamic acid 2-ethylhexyl ester and / or 4-methoxycinnamic acid propyl ester and / or 4-methoxycinnamic acid isoamyl ester. Such combinations are advantageously combined with water-soluble filters such as, for example, 2-phenylbenzimidazole-5-sulfonic acid and its alkali metal, alkaline earth metal, ammonium, alkylammonium, alkanolammonium and glucammonium salts.

In addition to the soluble substances mentioned, insoluble sunscreen pigments, namely finely dispersed metal oxides or salts, are also suitable for this purpose. Examples of suitable metal oxides are, in particular, zinc oxide and titanium dioxide and, in addition, oxides of iron, zirconium, silicon, manganese, aluminum and cerium, and mixtures thereof. As salts silicates (talc), barium sulfate or zinc stearate can be used. The oxides and salts are used in the form of the pigments for skin-care and skin-protecting emulsions and decorative cosmetics. The particles should have an average diameter of less than 100 nm, preferably between 5 and 50 nm and in particular between 15 and 30 nm. They may have a spherical shape, but it is also possible to use those particles which have an ellipsoidal or otherwise deviating form from the spherical shape. The pigments can also be surface treated, i. hydrophilized or hydrophobized. Typical examples are coated titanium dioxides, e.g. Titanium dioxide T 805 (Degussa) or Eusolex® T2000 (Merck). Suitable hydrophobic coating agents are in particular silicones and in particular trialkoxyoctylsilanes or simethicones. In sunscreens, so-called micro- or nanopigments are preferably used. Preferably, micronized zinc oxide is used.

Biogenic agents and antioxidants

Examples of biogenic active substances include tocopherol, tocopherol acetate, tocopherol palmitate, ascorbic acid, (deoxy) ribonucleic acid and their fragmentation products, β-glucans, retinol, bisabolol, allantoin, phytantriol, panthenol, AHA acids, amino acids, ceramides, pseudoceramides, essential oils, Plant extracts, such as Prunus extract, Bambaranussextrakt or vitamin complexes to understand.

Antioxidants interrupt the photochemical reaction chain, which is triggered when UV radiation penetrates the skin. Typical examples are amino acids (eg glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (eg urocaninic acid) and their derivatives, peptides such as D, L-carnosine, D-carnosine, L-carnosine and their derivatives (eg Anserine), carotenoids, carotenes (eg a-carotene, .beta.-carotene, lycopene) and their derivatives, chlorogenic acid and its derivatives, lipoic acid and its derivatives (eg dihydrolipoic acid), aurothioglucose, propylthiouracil and other thiols (eg thioredoxin, Glutathione, cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, g- Linoleyl, cholesteryl and glyceryl esters) and their salts, dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and derivatives thereof (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) and sulfoximine compounds (eg buthionine sulfoximines, homocysulfonimine, butioninsulfones , Penta-, hexa-, heptathionine-sulfoximine) in very low tolerated dosages (eg pmol to mGhoI / kg), furthermore (metal) chelators (eg α-hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin), α-hydroxy acids (eg citric acid , Lactic acid, acetic acid), humic acid, bile acid, bile extracts, bilirubin, biliverdin, EDTA, EGTA and their derivatives, unsaturated fatty acids and their derivatives (eg g-linolenic acid, linoleic acid, oleic acid), folic acid and its derivatives, ubiquinone and ubiquinol and their derivatives, vitamin C and derivatives (eg ascorbyl palmitate, Mg-ascorbyl phosphate, ascorbyl acetate), tocopherols and derivatives (eg vitamin E acetate), vitamin A and others Derivatives (vitamin A palmitate) and coniferyl benzoate of benzoin, rutinic acid and its derivatives, α-glycosylrutin, ferulic acid, furfurylideneglucitol, carnosine, butylhydroxytoluene, butylated hydroxyanisole, nordihydroguaiacetic acid, nordihydroguajaretic acid, trihydroxybutyrophenone, uric acid and its derivatives, mannose and their derivatives, superoxide dismutase, zinc and its derivatives (eg ZnO, ZnS0 ₄ ) selenium and its derivatives (eg selenium methionine), stilbenes and their derivatives (eg stilbene oxide, trans-stilbene oxide) and the derivatives suitable according to the invention (salts , Esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids) of these active substances mentioned.

film formers

Typical film formers are, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinylpyrrolidone, vinylpyrrolidone / vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives, collagen, hyaluronic acid or salts thereof and similar compounds.

Antidandruff agents

Anti-dandruff agents used are Pirocton olamine (1-hydroxy-4-methyl-6- (2,4,4-trimethylphenyl) -2- (1H) -pyridinone monoethanolamine salt), Baypival® (climbazole), Ketoconazole® (4 Acetyl-1 - {-4- [2- (2,4-dichlorophenyl) r-2- (1 H -imidazol-1-ylmethyl) -1,3-dioxylan-c-4-ylmethoxyphenyl} piperazine, Ketoconazole, Elubiol , Selenium disulfide, sulfur colloidal, sulfur polyethyleneglycol sorbitan monooleate, sulfur trizinol polyethoxylate, sulfurized distillates, salicylic acid (or in combination with hexachlorophene), undecylenic acid monoethanolamide sulfosuccinate Na salt, Lamepon® UD (protein undecylenic acid condensate), zinc pyrithione, aluminum pyrithione and magnesium pyrithione / Dipyrithione magnesium sulfate in question.

Other additives

Suitable swelling agents for aqueous phases are montmorillonites, clay minerals, pemulen and alkyl-modified carbopol types (Goodrich). Further suitable polymers or swelling agents can be reviewed by R. Lochhead in Cosm.Toil. 108, 95 (1993). Insect repellents are N, N-diethyl-m-toluamide, 1, 2-pentanediol or ethyl Butylacetyla- minopropionate in question, suitable as a self-tanner dihydroxyacetone. As tyrosine supplements, For example, arbutin, ferulic acid, kojic acid, coumaric acid and ascorbic acid (vitamin C) are considered to prevent the formation of melanin and find application in depigmentation agents.

protein

If desired, it is possible to use further protein hydrolyzates known from the prior art, for example based on keratin, such as the commercially available Nutrilan® keratin W PP or on the basis of wheat such as Gluadin® WLM Benz, Gluadin® WK or Gluadin® WP. It is also possible to add small amounts of free amino acids such as lysine or arginine.

hydrotropes

Hydrotropes such as, for example, ethanol, isopropyl alcohol, or polyols can also be used to improve the flow behavior. Polyols contemplated herein preferably have from 2 to 15 carbon atoms and at least two hydroxyl groups. The polyols may contain other functional groups, in particular amino groups, or be modified with nitrogen. Typical examples are

• glycerin;

Alkylene glycols, such as, for example, ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol and polyethylene glycols having an average molecular weight of from 100 to 1000 daltons;

Technical Oligoglyceringemische with an intrinsic degree of condensation of 1, 5 to 10 such as technical Diglyceringemische with a diglycerol content of 40 to 50 wt .-%;

Methylol compounds, in particular trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol and dipentaerythritol;

Lower alkyl glucosides, in particular those having 1 to 8 carbons in the alkyl radical, such as, for example, methyl and butyl glucoside;

Sugar alcohols having 5 to 12 carbon atoms, such as sorbitol or mannitol,

• sugars having 5 to 12 carbon atoms, such as glucose or sucrose;

• amino sugars, such as glucamine;

• Dialcoholamines, such as diethanolamine or 2-amino-1,3-propanediol.

preservative

Suitable preservatives are, for example, benzoates, phenoxyethanol, formaldehyde solution, parabens, pentanediol, sorbic acid, levulinic acid and arachidonic acid, as well as the silver complexes known under the name Surfacine® and the further classes of compounds listed in Appendix 6, Part A and B of the Cosmetics Regulation. Perfume oils and flavors

As perfume oils are called mixtures of natural and synthetic fragrances. Natural fragrances are extracts of flowers (lily, lavender, roses, jasmine, neroli, ylang-ylang), stems and leaves (geranium, patchouli, petitgrain), fruits (aniseed, coriander, cumin, cucumber), fruit peel ( Bergamot, Lemon, Oranges), Roots (Macis, Angelica, Celery, Cardamom, Costus, Iris, Calmus), Woods (Pine, Sandey, Guaiac, Cedar, Rosewood), Herbs and Grasses (Tarragon, Lemongrass , Sage, thyme), needles and twigs (spruce, fir, pine, pine), resins and balsams (galbanum, elemi, benzoin, myrrh, olibanum, opoponax). Furthermore, animal raw materials come into question, such as civet and Castoreum. Typical synthetic fragrance compounds are products of the ester type, ethers, aldehydes, ketones, alcohols and hydrocarbons. Fragrance compounds of the ester type are known e.g. Benzyl acetate, phenoxyethyl isobutyrate, p-tert-butylcyclohexyl acetate, linalyl acetate, dimethylbenzylcarbinylacetate, phenylethyl acetate, linalylbenzoate, benzylformate, ethylmethylphenylglycinate, allylcyclohexylpropionate, styrallylpropionate and benzylsalicylate. The ethers include, for example, benzyl ethyl ether, to the aldehydes e.g. the linear alkanals having 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehyde, cyclamen aldehyde, hydroxycitronellal, lilial and bourgeonal, to the ketones e.g. the alcohols, anethole, citronellol, eugenol, isoeugenol, geraniol, linalool, phenylethyl alcohol and terpineol; the hydrocarbons mainly include the terpenes and balsams. Preferably, however, mixtures of different fragrances are used, which together produce an attractive fragrance. Also, lower volatility volatile oils, which are most commonly used as aroma components, are useful as perfume oils, e.g. Sage oil, chamomile oil, clove oil, lemon balm oil, mint oil, cinnamon leaf oil, lime blossom oil, juniper berry oil, vetiver oil, olive oil, galbanum oil, labolanum oil and lavandin oil. Bergamot oil, dihydro myrcenol, lilial, lyral, citronellol, phenylethyl alcohol, a-hexyl cinnamaldehyde, geraniol, benzylacetone, cyclamen aldehyde, linalool, Boisambrene Forte, Ambroxan, indole, hedione, sandelice, citron oil, mandarin oil, orange oil, allylamyl glycolate are preferably used , Cyclovertal, lavandin oil, muscat oil, β-damascone, geranium oil bourbon, cyclohexyl salicylate, vertofix coeur, iso-E-super, fixolide NP, evernyl, iraldeine gamma, phenylacetic acid, geranyl acetate, benzyl acetate, rose oxide, romilllate, irotyl and Floramate alone or in mixtures used. Suitable flavors are, for example, peppermint oil, spearmint oil, aniseed oil, star aniseed oil, caraway oil, eucalyptus oil, fenchel oil, citron oil, wintergreen oil, clove oil, menthol and the like.

dyes

Dyes which may be used are those which are suitable and approved for cosmetic purposes, as compiled, for example, in the publication "Kosmetische Färbemittel" of the Coloring Committee of the Deutsche Forschungsgemeinschaft, Verlag Chemie, Weinheim, 1984, pp. 81-106. Examples are Kochillerot A (Cl 16255), Patent Blue V (C.1.42051), Indigotin (Cl73015), Chlorophyllin (Cl75810), Quinoline Yellow (Cl47005), Titanium Dioxide (Cl77891), Indanthrene Blue RS (Cl 69800) and Krapplack (Cl58000). As a luminescent dye and luminol may be included. Examples:

The following examples are intended to further describe and explain the invention without limiting its scope.

The effect of 1, 2-alkanediols of the formula (I) on the foam properties (foam height, foamability) was determined according to the following test methods:

A) Examples 1 to 6: Use according to the invention of the 1,2-alkanediols for lauryl glucoside and for a surfactant mixture with lauryl glucoside and Na lauryl glucoside carboxylate

The agitator used was a stirring machine of the "Eurostar 20 digital" type from IKA-Werke GmbH & Co. KG, Germany, which was equipped with a dispersion disk ("Z disk", diameter 6 cm) ("stirrer").

To determine the foam height, in each case the amount of A1 or A2 mentioned in Table 1 was determined in an 800 ml beaker (Schott Duran, H: 13.5 cm, R: 9.4 cm) with stirrer

A1) lauryl glucoside (Plantacare® 1200, active substance content ~ 52% by weight)

A2) Mixture of Na lauryl glucoside carboxylate and lauryl glucoside (Plantapon® LGC Sorb .; active substance content ~ 30% by weight, weight ratio approximately 1.5: 1)

Weighed and mixed with 50 ml of tap water.

To this was added the 1,2-alkanediol indicated in Table 1 in the stated amount:

O _Q = n-hexanediol

Cs = n-octanediol

C10 = n-decanediol

The resulting aqueous mixture or solution was adjusted to a pH of 5.5 by addition of a suitable amount of aqueous NaOH solution (c = 1.0 mol / l) with warm water (about 30 ° C.) 100 ml of total volume and then heated to 30 ° C (water bath). Subsequently, the resulting tempered mixture was stirred for 10 seconds (stopwatch) to generate foam with a stirrer (see above) at a speed of 1300 rpm. Immediately after switching off the stirrer and without removing the stirrer (dispersion disk, see above) from the beaker, the height of the resulting foam was then measured from the bottom of the beaker with a ruler and indicated in cm as "foam height"("SH") , The results of this test can be found in Table 1: Table 1 (foam height in cm after 10 sec, at 30 ° C, pH 5.5, 1300 rpm - LW)

From Table 1 it can be seen that by adding the diols of the invention, the foam height after 10 seconds, i. the so-called foaming behavior is improved. The foam height was improved by at least 40% both in the case of the alkylpolyglucoside A1 and in the mixture of alkylpolyglucoside and alkylpolyglucosidecarboxylate according to A2, in particular due to the addition of Cs and / or Cio-diols, and this although the amount of surfactant at A1 or A2 is lower than in the comparative example (only 2.0 g instead of 2.5 g).

Particularly good results were obtained for 1, 2 octanediol.

B) Examples 7 to 9: Determination of the foam height of detergents according to the invention with diols in comparison with detergents without diols

Detergents were prepared with the ingredients and amounts listed in Table 2.

Example 7 / Comparative Example V7

For the preparation of the detergents according to Comparative Example 7, the ingredients of phase A were mixed with those of phase B in the order listed until complete homogeneity. Then the ingredients of Phase C were added and heated to 70 ° C; After complete dissolution, the mixture was cooled to 30 ° C. and the ingredients of phase D were added. The pH adjustment is analogous to phase E and the viscosity adjustment analogous to phase F. It was a liquid hair shampoo preparation obtained with a pH of 4.8 and a Brookfield viscosity (RVT, spindle 4, 10 rpm, 23 ° C ) of 8500 mPas.

Comparative Example 7 was used for Example 7, but the amount of water was reduced and added about 23 wt .-% n-octanediol in process step G.

For Comparative Example C8, Phase A ingredients were mixed with those of Phase B in the order listed until complete homogeneity. Then the thicker the phase C added. Subsequently, the ingredients of phase D were added in the order listed and mixed until complete homogeneity. The pH is adjusted analogously to phase E. A liquid hair shampoo preparation having a pH of 4.9 and a Brookfield viscosity (RVT, spindle 4, 10 rpm, 23 ° C.) of 6700 mPas was obtained.

For Example 8 was carried out analogously to Comparative Example 8, but the amount of water was reduced and added about 23 wt .-% n-octanediol in process step G.

For Comparative Example C9, the ingredients of Phase A were mixed in the order listed after 10 minutes of swelling, the ingredients of Phase B in the order listed stirred until complete homogeneity. The pH adjustment takes place in phase C and the viscosity adjustment in phase D. A liquid hair shampoo preparation having a pH of 4.8 and a Brookfield viscosity (RVT, spindle 4, 10 rpm, 23 ° C.) was obtained. of 9900 mPas.

For Example 9 was carried out analogously to Comparative Example 9, but the amount of water was reduced and added about 23 wt .-% n-octanediol in process step G.

The foam height was determined in cm according to the Sita test at 30 ° C., pH 5.5 and 1300 rpm LW after 20 s and after 80 s as follows. The formulation to be tested was placed in the removable tank of a SITA Foam Tester R-2000. The regulation of the conditions (temperature, number and duration of measurements, stirring speed) was carried out via the connected PC. The temperature of the formulation was carried out via an outer jacket of the Aufschäumgefäßes, which in turn is fed by a water bath. The measurement was started via the PC.

The formulation to be tested was stirred at a speed of 1300 rpm and had a temperature of 30 ° C (+/- 1 ° C). The foam height (in cm) was recorded electronically after a measurement period of 20 and 80s. There was a triple determination of each formulation. After each measurement curve, an automatic 8-minute cleaning took place.

The statement after 20 seconds shows that the detergents according to the invention with diol have a better foaming behavior than without diol and the foam also remains stable over a longer period. Table 2 shows the amounts used calculated on the active substance content.

Table 2

Cont. Table 2

Claims

claims

1. Use of 1,2-alkanediols of the formula (I)

2. Use according to claim 1, characterized in that 1.2 alkanediols of the formula (I) are used, wherein R ^{1 is} an unbranched hydrocarbon radical having 6 to 12 carbon atoms, preferably wherein R ^{1 is} an unbranched hydrocarbon radical having 6 carbon atoms.

3. Use according to claim 1, characterized in that the 1,2 alkane diols for surfactant mixtures comprising alkyl and / or alkenyl oligoglycosides of the formula (II),

R ² 0- [G] _p (II) wherein R ^{2 is} an alkyl and / or alkenyl radical of 8 to 18 carbon atoms, G is a sugar radical of 5 or 6 carbon atoms and p is a number of 1 to 10.

4. Use according to claim 3, characterized in that the 1,2 alkane diols are used for surfactant mixtures comprising alkyl and / or alkenyl oligoglycosides of the formula (II) in which R ^{2 is} an alkyl and / or alkenyl radical having 8 to 14 Carbon atoms.

5. Use according to claim 1, characterized in that the 1,2 alkane diols for surfactant mixtures containing derivatives of the alkyl and / or alkenyl oligoglycosides of the formula

(III)

R ³ 0- [G] pi- (CH ₂ 0C00M) i- ₃ (III) wherein R ^{3 is} an alkyl and / or alkenyl radical of 8 to 18 carbon atoms, G is a sugar radical of 5 or 6 carbon atoms and p 1 is a number is from 1 to 10 and the radical M is selected from the group H, Li, Na, K, Ca / 2, Mg / 2, ammonium and alkanolamines used.

6. Use according to any one of claims 1 to 5, characterized in that the 1, 2 alkane diols for surfactant mixtures containing alkyl and / or Alkenyloligoglykoside of formula (II) and alkyl and / or Alkenyloligoglykosidcarboxylate of formula (III), wherein R ² and R ³ , G and p and p1 and M have the meaning given above, can be used.

7. Use according to claim 1, characterized in that the 1,2 alkanediols of the formula (I) are used for surfactant mixtures consisting of alkyl and / or alkenyl oligoglycosides and / or derivatives of alkyl and / or alkenyl oligoglycosides.

8. Use according to at least one of claims 1 to 6, characterized in that the 1, 2 alkanediols are used for surfactant mixtures containing further surfactants, preferably other surfactants except ether sulfates, preferably further surfactants of the formulas (IV) to (X) and in particular further surfactants selected from the group formed by acylglutamates, betaines, sulphosuccinates, amidoamines, isethionates, alpha-sulfofatty acid disalts and amphoacetates.

9. Use according to claim 8, characterized in that the 1,2-alkanediols are used for surfactant mixtures which are used in amounts of from 10 to 50, preferably from 20 to 40,% by weight of alkyl and / or alkenyl oligoglycosides and / or derivatives of Alkyl and / or alkenyloligoglykoside and in amounts of from 50 to 90 wt .-%, preferably 60 to 80 wt .-% further surfactants according to claim 8 included.

10. Use according to any one of claims 1 to 9, characterized in that the 1, 2-alkanediols in a weight ratio of 1: 10 to 10: 1, preferably 1: 7 to 7: 1 - based on the active content of alkyl and / or alkenyl oligoglycosides and / or derivatives thereof in the surfactant mixture.

1 1. Use according to one of claims 1 to 10, characterized in that the 1, 2 alkanediols to improve the foam volume, preferably the Anschäumverhal- tens measured as a foam height after 10 seconds at 30 ° C, pH 5.5 with the stirring motor of the type "Eurostar 20 digital" from IKA-Werke GmbH & Co. KG equipped with a dispersion disc Z-disc, diameter 6 cm by at least 15%, preferably by 30% up to 80% - based on foam height of the same surfactant mixture without 1, 2 alkandiol - be added.

12. A surfactant compound with improved foam consisting of 1, 2 alkanediols according to claim 1 or 2 and alkyl and / or Alkenyloligoglykosiden and / or derivatives thereof, preferably alkyl and / or Alkenyloligoglykosiden of formula (II) and / or their derivatives of the formula (III) in which R ² or R ³ , G and p have the meaning given above according to claims 3, 4, 5 and / or 6.

13. A surfactant compound with improved foam consisting of 1, 2 alkanediols according to claim 1 or 2 and a surfactant mixture of alkyl and / or Alkenyloligoglykosiden and / or derivatives thereof and other surfactants, preferably except Ethersulfa- th, preferably other surfactants of the formula (IV ) to (X) and in particular further surfactants selected from the group formed by acylglutamates, betaines, sulphosuccinates, amidoamines, isethionates, alpha-sulfofatty acid disalts and amphoacetates.

14. Cosmetic cleanser for skin and hair containing 1, 2 alkanediols according to formula (I) according to claim 1 or 2 and alkyl and Alkenyloligoglykoside and / or derivatives thereof, wherein the 1, 2 alkanediols to improve the foaming behavior in a weight ratio of 1: 10 to 10: 1, preferably 1: 7 to 7: 1, - based on the active content of alkyl and / or Alkenyloligoglykosiden and / or derivatives thereof in the T ensidmischung - are included.

15. Cosmetic cleanser for skin and hair containing a surface-active compound according to claim 12.

16. Cosmetic cleanser for skin and hair comprising a surface-active compound according to claim 12 and further surfactants, preferably excluding ether sulfates, preferably further surfactants of the formula (IV) to (X) and in particular further surfactants which are selected from those of Acylglutamates, betaines, sulfosuccinates, amidoamines, isethionates, alpha-sulfofatty acid disalts and amphoacetates.

17. Cosmetic cleanser for skin and hair comprising a surface-active compound according to claim 13.

18. Cosmetic cleanser for skin and hair according to one of claims 14 to 17, characterized in that it has an improved foam volume, preferably an improved foam stability measured as foam height in cm after 20 seconds measured according to the Sita test at 30 ° C, pH 5.5, 1300 revolutions per minute by at least 25%, preferably by 30 to 100% - based on the same cosmetic detergent without 1, 2-alkanediol - has.

19. A method for improving the foaming behavior of alkyl and / or Alkenyloligoglyko- siden and / or derivatives thereof, characterized in that one adds 1, 2 alkanediols of the formula (I) according to claim 1 or 2.

20. A process for improving the foaming behavior of cosmetic cleansing compositions comprising alkyl and / or alkenyl oligoglycosides and / or derivatives thereof, characterized in that one adds 1, 2 alkanediols of the formula, preferably in the form of a surface-active compound according to claim 12 or 13.