EP3752126A1

EP3752126A1 - Use of 1,2-alkanediols as lather boosters for citric acid ester surfactants comprising ethoxylated alcohols

Info

Publication number: EP3752126A1
Application number: EP19703100.8A
Authority: EP
Inventors: Catherine Weichold; Ansgar Behler; David Melchior; Stefan Busch; Hans-Willi Kling; Karsten Lange; Bernd Jakob
Original assignee: BASF SE; Bergische Universitaet Wuppertal
Current assignee: BASF SE; Bergische Universitaet Wuppertal
Priority date: 2018-02-14
Filing date: 2019-02-06
Publication date: 2020-12-23
Also published as: WO2019158411A1

Abstract

The invention relates to the use of a 1,2-alkanediol as lather enhancers and/or lather boosters for a citric acid ester surfactant, which comprises one or more citric acid esters with one or more ethoxylated alcohols, and to a corresponding latherable composition. The invention further relates to a method for producing said type of latherable composition and to a corresponding washing, cleaning and/or care agent.

Description

Use of 1,2-alkanediols as foam improvers for citric acid ester surfactants comprising ethoxylated alcohols

The present invention relates to the use of a 1,2-alkanediol as a foam enhancer and / or foam improver for a citric acid ester surfactant comprising one or more esters of citric acid with one or more ethoxylated alcohols and a corresponding foamable composition. Furthermore, the present invention also relates to a process for the preparation of such a foamable composition and to a corresponding washing, cleaning and / or care agent.

Citric acid esters such as esters of citric acid with alkoxylated alcohols are already used in detergents, cleaners or care agents as surfactants or emulsifiers and as conditioning agents to create or improve a pleasant haptic perception or to prevent the electrical charging of hair. In particular, esters of citric acid with alkoxylated alcohols are often used as conditioning agents in cosmetic products to improve the skin and hair feel or skin and hair feel, to improve the wet and dry combing and antistatic hair, to improve the softness of the skin and hair Increasing the shine and / or smoothness of the skin and hair as well as a moisturizer ("moisturizer"). Depending on the intended use, foaming may occur.

neither desired nor desired. For example, in detergents for washing machines foaming or excessive foaming is often undesirable, while washing or dishwashing detergents for hand washing or personal care articles such as cosmetic products, such as hair shampoos, require foaming wrap, often even intense and long-lasting foaming is.

The prior art has already disclosed various publications on the use of citric acid esters in detergents, cleaners or conditioners and on the preparation of foaming compositions in general:

Document US 8,747,822 B1 describes alkoxylated citrate polyesters which are e.g. are suitable as skin or hair care products.

Document US Pat. No. 8,785,676 B1 describes citrate-co-polyesters which are suitable, for example, as constituents of cosmetic emulsions.

Document WO 2013/127960 A1 describes a process for the preparation of esters or ethers between fatty acid derivatives and hydroxycarboxylic acids which are e.g. are of interest as emulsifiers or surfactants.

The document WO 2013/0571 10 A1 describes a process for the synthesis of citric acid esters, which i.a. can be used as emulsifiers or surfactants.

The document WO 2015/028344 A1 describes oil concentrates with liquid anionic surfactants which are suitable for the production of cosmetic cleansing agents.

Document US 4,294,728 describes shampoo or foam bath compositions comprising an aqueous solution of at least one cationic, amphoteric or zwitterionic surfactant and at least one dihydric alcohol. The document DE 931974 describes washing and cleaning agents with improved foaming power.

Document US 2,956,025 A discloses sulfonate detergent compositions having improved foaming characteristics.

The document US 2,874,127 A also deals with improved sulfonate detergent compositions having improved foam characteristics

The document EP 0 176 018 A1 describes a stripping agent based on an aqueous alkali and / or ammonium hydroxide solution containing surfactants, which can be applied as a solid foam.

The document EP 1 621 231 A1 describes a conditioning surfactant preparation which is e.g. Contains citric acid ester surfactants.

However, in view of the known state of the art, there is still a need to increase the range of use of polyhydric alcohols known per se by using new ones. Furthermore, there is also a need to specifically change the properties of detergents, cleaners and / or care products and, for example, to improve or increase their foam properties for specific applications.

It was therefore a primary object of the present invention to increase the scope of use of known polyhydric alcohols by new uses. A further object of the present invention was to provide compositions of citric acid ester surfactants having improved foam properties and a process for their preparation.

Furthermore, it was a specific object of the present invention to provide washing, cleaning and / or care products which contain citric acid ester surfactants and have improved or increased foam properties.

It has now surprisingly been found that the primary object and other objects and / or subtasks of the present invention are achieved by the use of a 1,2-alkanediol of the formula (I)

R ^{1 is} -CH (OH) -CH ₂ -OH (I) wherein

R ^{1 is} an unbranched or branched, preferably unbranched, alkyl group having a total of 6 to 12, preferably having a total of 6 to 10, particularly preferably having a total of 6 to 8, carbon atoms,

as a foam intensifier and / or foam improver for a citric acid ester surfactant which comprises one or more esters of citric acid with one or more ethoxylated alcohols of the formula (II)

R ² -O (CH ₂ CH ₂ -O) n H (II) wherein

R ^{2 is} an unbranched or branched alkyl group having a total of 6 to 22 carbon atoms or an unbranched or branched alkenyl group having a total of 6 to 22 carbon atoms and n is an integer ranging from 1 to 50.

The use of 1, 2-alkanediols of the formula (I) according to the invention enables foam reinforcement and / or foam improvement (generally better foamability) of the citric acid ester surfactants to be used according to the invention, at least with regard to one, in many cases to two and ideally to all three the foaming properties to be achieved, the foam height to be achieved, the foam quality to be achieved and / or the foam stability to be achieved, in each case in comparison to the corresponding citric acid ester surfactants to be used according to the invention alone, without the use of the 1,2-alkanediols to be used according to the invention of the formula (I), to achieve the aforementioned foam properties. The invention as well as preferred combinations of preferred parameters, properties and / or constituents of the present invention are defined in the appended claims. Preferred aspects of the present invention are also set forth and defined in the following description and examples.

The criterion for a good foam quality in the context of the present invention is the presence of exclusively or predominantly fine-pored foam (small air bubbles) or the absence or at least substantial absence of larger or larger air bubbles in a foam.

As a measure of the foam stability, in the context of the present invention, the period of time, preferably under standard conditions, for which a foam produced is stable, ie. still has visible air bubbles.

The 1,2-alkanediol of the formula (I) to be used according to the invention can be used alone, i. be used as a pure 1, 2-alkanediol, or it may be a mixture of two or more 1, 2-alkanediols of the formula (I) are used. Such a mixture may contain any ratios of the two or more 1,2-alkanediols of formula (I).

In the ethoxylated alcohols of the formula (II), the variable "n" stands for the "degree of ethoxylation" known per se. The degree of ethoxylation, in accordance with the usual understanding in the art, gives an average value for the number of ethoxy units present in an ethoxylated alcohol of formula (II) ("-CH 2 CH 2 O-", repeat units). Preferably, the one or more ethoxylated alcohols of the formula (II) to be used according to the invention have an even number of carbon atoms. In the substituent R ² of the ethoxylated alcohol (s) of the formula (II), an alkenyl group means a hydrocarbon group which has one or more double bonds. Preferably, an aforementioned alkenyl group has one, two or three, more preferably one or two, double bonds.

Preference is given to a use according to the invention, wherein the ester or esters of citric acid to be used according to the invention are esters which can be prepared by esterification of citric acid with one or more ethoxylated alcohols of the formula (II).

Likewise preferred is a preferred use according to the invention or one described above or below, wherein in one or at least one of a plurality of 1,2-alkanediols of the formula (I) R ^{1 is} an unbranched or branched, preferably unbranched, alkyl group a total of 6 to 10, preferably having a total of 6 to 8 carbon atoms, and preferably the one or at least one of a plurality of 1, 2-alkanediols of the formula (I) is selected from the group consisting of n-1, 2-octanediol, n- 1, 2-decanediol and n-1, 2-dodecanediol,

and very particularly preferably the one or at least one of a plurality of 1, 2-alkanediols of the formula (I) is selected from the group consisting of n-1, 2-octanediol and n-1, 2-decanediol.

It has been found in our own experiments that when using the abovementioned 1, 2-alkanediols or the 1,2-alkanediols indicated above as being particularly advantageous, particularly good results of foam reinforcement and / or foam improvement, in particular a particularly good improvement of achievable foam heights and the achievable foam qualities, are obtained in or with citric acid ester surfactants to be used according to the invention. It is also preferred to use according to the invention or one described above or below, wherein the or the 1, 2-alkanediols of the formula (I) are used in a foam-enhancing and / or foam-improving effective amount, preferably in a total amount in the range of 5 % By weight to 40% by weight, particularly preferably in the range from 10% by weight to 30% by weight, based on the total mass (or total weight) of the citric acid ester surfactant contained in the composition.

It has been shown in own experiments that in the specified ranges of the total amount of 1,2-alkanediol of the formula (I) to be used according to the invention the best results of the foam reinforcement and / or the foam improvement, in particular a particularly good improvement of the achievable foam heights, at or with citric acid ester surfactants to be used according to the invention. A combination of 1,2-alkanediols of the formula (I) preferably used according to the invention with total amounts of 1,2-alkanediols of the formula (I) preferably used according to the invention gives particularly preferred uses according to the invention. Preference is also given to a preferred use according to the invention or one described above or below, in which one or at least one of several ethoxylated alcohols of the formula (II) n is an integer in the range from 1 to 20, preferably in the range from 1 to 10 and more preferably in the range of 3 to 8, means and / or

R ^{2 is} an unbranched or branched alkyl group having a total of 8 to 20, preferably 10 to 20, more preferably 12 to 18, carbon atoms, or a straight or branched alkenyl group having a total of 8 to 20, preferably 10 to 20 in total , particularly preferably having a total of 12 to 18, carbon atoms.

According to the invention, combinations of preferred meanings of the degree of ethoxylation n with preferred meanings of R ^{2 give} particularly preferred ethoxylated alcohols of the formula (II) which can be used or used according to the invention.

Preference is likewise given to a preferred use according to the invention or one described above or below, wherein the citric acid ester surfactant comprises a mixture of several esters of citric acid with one or more, preferably with several, ethoxylated alcohols of the formula (II), where the ethoxylated alcohols of the formula (II) preferably comprise mixtures of technical fatty alcohols. Preferably, one or more alcohols are used to form or prepare the ethoxylated alcohols of the formula (II) (ie, alcohols whose alkyl or alkenyl group then form the radical R ² ), which are selected from the group consisting of caprolanol, capryl alcohol , 2-ethylhexyl alcohol, capric alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol and brassidyl alcohol and mixtures thereof.

Particular preference is given to using or preparing the ethoxylated alcohols of the formula (II) mixtures of alcohols which preferably each have a total number of carbon atoms in the range from 12 to 18 and preferably by industrial processing of plant extracts, more preferably from plant extracts of coconut palms and or oil palms (also referred to as "mixtures of technical fatty alcohols"). Preferred mixtures of alcohols obtained by industrial processing of plant extracts are selected from the group consisting of coconut oil, palm alcohol, palm kernel alcohol, tallow fatty alcohol and mixtures thereof. The industrial processing of the abovementioned plant extracts is preferably carried out by high-pressure hydrogenation of technical methyl esters based on fats and oils or of aldehydes from Roelen's oxo synthesis or as a monomer fraction in the dimerization of unsaturated fatty alcohols.

Ethoxylated alcohols of the formula (II) formed or prepared from the abovementioned preferred mixtures of alcohols preferably have a degree of ethoxylation n in the range from 1 to 10, particularly preferably in the range from 3 to 8.

The use according to the invention or usability of a 1,2-alkanediol of the formula (I) as foam intensifier and / or foam improver for a citric acid ester surfactant which comprises ethoxylated alcohols of the formula (II) which are formed from mixtures of alcohols, in particular from mixtures of technical fatty alcohols or have been prepared, has the advantage that such mixtures of alcohols are well available on the market, inexpensive and well suited as basic materials for detergents, cleaners and / or care products such as cosmetics. Corresponding cosmetics are particularly skin and hair friendly, have excellent conditioning properties and contain little and preferably no cationic surfactants. A further aspect of this advantage is the particularly good suitability of the 1,2-alkanediols of the formula (I) as foam boosters and / or foam improvers for citric acid ester surfactants, which are prepared from such abovementioned mixtures of alcohols (as constituents of ethoxylated alcohols of the formula (I) II)) were formed or produced.

In a specific embodiment of the present invention, mixtures of alcohols containing a total amount of C 12 -alcohols (ie, alcohols or alkyl alcohols and / or alkenyl alcohols which have a total number of carbon atoms) are used to form or prepare the ethoxylated alcohols of the formula (II) of 12 carbon atoms, all possible isomers are included, this definition also applies mutatis mutandis to the alcohols of higher or lower chain lengths given in this text) in the range of 65 wt .-% to 75 wt .-%, a total amount of C14 alcohols in the range of 20% to 30% by weight, a total amount of C16 alcohols in the range of 0% to 5% by weight, and a total amount of C18 alcohols in the range of 0% by weight. to 5 wt .-%, each based on the total mass (or the total weight) of the mixture of alcohols, each comprising 100 wt .-% of alcohols. Ethoxylated alcohols of the formula (II) formed or prepared from the preferred mixtures of alcohols specified hereinbefore preferably have a degree of ethoxylation n in the range from 3 to 5. The mixtures of alcohols of this specific embodiment are commercially available, for example under the trade name "Lorol® Spezial" from BASF SE.

In a further specific embodiment of the present invention, mixtures of alcohols containing a total amount of C 12 alcohols in the range from 45% by weight to 60% by weight, are used to form or prepare the ethoxylated alcohols of the formula (II) Total amount of C14 alcohols in the range of 15% to 30% by weight, a total amount of C16 alcohols in the range of 5% to 15% by weight and a total amount of C18 alcohols in the range of 8 wt .-% to 20 wt .-%, each based on the total mass (or the total weight) of the mixture of alcohols, each comprising 100 wt .-% of alcohols. Ethoxylated alcohols of the formula (II) formed or prepared from the preferred mixtures of alcohols specified hereinbefore preferably have a degree of ethoxylation n in the range from 6 to 8. The mixtures of alcohols of this specific embodiment are commercially available, for example under the trade name "Lorol® Technical" from BASF SE.

Preferably, the citric acid ester surfactant to be used according to the invention comprises one or more constituents (or in many cases consists of one or more constituents, several constituents meaning a mixture of individual constituents) selected from the group consisting of:

Citric acid, preferably in a total amount of not more than 10% by weight, more preferably in a total amount in the range of 1 wt .-% to 9 wt .-%, based on the total mass (or the total weight) of citric acid ester surfactant ;

Own condensates of citric acid,

Salts of citric acid,

Monoesters of citric acid with ethoxylated alcohols of the formula (II), - salts of the monoesters of citric acid with ethoxylated alcohols of the formula (II),

Diesters of citric acid with ethoxylated alcohols of the formula (II),

Salts of diesters of citric acid with ethoxylated alcohols of the formula (II) and

Triester of citric acid with ethoxylated alcohols of the formula (II).

The aforementioned esters and / or salts of citric acid may be present in any isomeric forms as well as mixtures of such isomeric forms.

Preferably, the abovementioned salts of citric acid, the monoesters of citric acid with ethoxylated alcohols of the formula (II) and / or the diesters of citric acid with ethoxylated alcohols of the formula (II) are in each case present as alkali metal, alkaline earth metal, ammonium, alkylammonium that is, as salts with ammonium cations in which one, two, three or all four hydrogen atoms are each substituted by an alkyl group having a total of 1 to 4 carbon atoms or are unsubstituted), alkanolammonium (ie as salts with ammonium cations in which one, two, three or four hydrogen atoms are each substituted by a hydroxyalkyl group having a total of 1 to 4 carbon atoms or are unsubstituted) and / or glucammonium salts (ie, ammonium salts of 1-amino-1-deoxy-D-glucitol, also referred to as D-glucamine, CAS RN 488-43-7). Salts of the monoesters of citric acid with ethoxylated alcohols of the formula (II) may be simple salts which still have a free carboxyl group, or they may be di-salts in which both non-esterified carboxyl groups are present as carboxylate salts.

It is furthermore preferably a preferred use according to the invention or one described above or below, wherein the citric acid ester surfactant to be used according to the invention comprises one or more constituents selected from the group consisting of monoesters and diesters of citric acid with ethoxylated alcohols of the formula (II), preferably in a total amount in the range from 50% by weight to 90% by weight, particularly preferably in the range from 60% by weight to 80% by weight, based on the total mass (or total weight) of the citric acid ester surfactant to be used according to the invention. Preference is also given to a preferred use according to the invention or one described above or below, wherein in the citric acid ester surfactant to be used according to the invention the weight ratio of monoester constituents (ie monoesters and salts of the monoesters) of citric acid with ethoxylated alcohols of the formula (II) to diester Ingredients (ie diesters and salts of diesters) of citric acid with ethoxylated alcohols of the formula (II) in the range of 3: 1 to 10: 1, preferably in the range of 5: 1 to 8: 1, is located.

Particularly preferred citric acid ester surfactants to be used according to the invention are disclosed in particular in document EP 1 621 231 A1. A citric acid ester surfactant which is particularly preferably to be used according to the invention is commercially available, for example under the trade name "Plantapon® LC7" from BASF SE (CAS RN: 565429-75-6). The invention also relates to a foamable composition comprising one or more 1,2-alkanediols of the formula (I)

R ^{1 is} -CH (OH) -CH ₂ -OH (I) wherein

R ^{1 is} an unbranched or branched, preferably unbranched, alkyl group having a total of 6 to 12, preferably having a total of 6 to 10, particularly preferably having a total of 6 to 8, carbon atoms, and a citric acid ester surfactant comprising one or more esters of citric acid with one or more ethoxylated alcohols of the formula (II)

R ² -O (CH ₂ CH ₂ -O) n H (II) wherein

R ^{2 is} an unbranched or branched alkyl group having a total of 6 to 22 carbon atoms or an unbranched or branched alkenyl group having a total of 6 to 22 carbon atoms, and n is an integer in the range of 1 to 50.

With regard to preferred embodiments and possible combinations of preferred embodiments of the composition according to the invention, the explanations given above for the use according to the invention apply correspondingly (if appropriate, mutatis mutandis), and vice versa.

In the composition according to the invention, the one or more 1,2-alkanediols of formula (I) exist as free compounds besides the citric acid ester surfactant (or its constituents), i. the one or more 1,2-alkanediols of the formula (I) are in particular not present as constituents esterified with one or more hydroxyl groups of citric acid.

Also preferred is a composition according to the invention, wherein in the one or at least one of the plurality of 1, 2-alkanediols of the formula (I) R ^{1 is} an unbranched hydrocarbon group having a total of 6 to 10, preferably having a total of 6 to 8 carbon atoms; and preferably one or at least one of the plurality of 1,2-alkanediols of the formula (I) is selected from the group consisting of n-1, 2-octanediol, n-1, 2-decanediol and n-1,2-dodecanediol; and particularly preferably the one or at least one of a plurality of 1,2-alkanediols of the formula (I) is selected from the group consisting of n-1, 2-octanediol and n-1, 2-decanediol.

Furthermore, preference is also given to a preferred composition according to the invention or one described above or below, wherein

- The one or more 1,2-alkanediols of the formula (I) are contained in a foam-enhancing and / or foam-improving effective amount, and / or

- The composition is foamable in contact with water, and / or

- The composition is at least in a ratio of 1: 4 (w / w) miscible with water. The composition of the invention is preferably foamable in contact with water. For foaming, the composition of the invention is preferably water or an aqueous (ie water-containing) solvent

mixed, dissolved, dispersed or emulsified. By mechanical action (introduction of, for example, air), foam can be developed in the resulting mixture, solution, dispersion or emulsion in a manner known per se.

It is therefore also preferred that a preferred inventive composition or one described above or below, wherein

the total amount of the one or more 1,2-alkanediols of the formula (I) is in the range from 5% by weight to 40% by weight, preferably in the range from 10% by weight to 30% by weight, based on the total mass (or the total weight) of the citric acid ester surfactant contained in the composition, and / or

the total amount of the one or more 1,2-alkanediols of the formula (I) in the range from 0.1% to 30% by weight, preferably in the range from 0.2% by weight to 25% by weight. %, more preferably in the range of 0.25 wt .-% to 10 wt .-%, based on the total mass (or the total weight) of the composition composition.

The invention also relates to a process for the preparation of an above-mentioned inventive or preferred foamable composition according to the invention, comprising the steps

(a) providing or preparing one or more ethoxylated alcohols of the formula (II)

R ² -O (CH ₂ CH ₂ -O) n H (II) wherein

R ^{2 is} an unbranched or branched alkyl group having a total of 6 to 22 carbon atoms or an unbranched or branched alkenyl group having a total of 6 to 22 carbon atoms and n is an integer in the range of 1 to 50,

(b) providing or producing citric acid or a derivative of citric acid suitable for esterification,

(c) reacting the one or more ethoxylated alcohols of formula (II) from step (a) with citric acid or its derivative suitable for esterification under conditions which allow esterification to a citric acid ester surfactant,

(d) adding a foam-enhancing and / or foam-improving effective amount of one or more 1, 2-alkanediols of the formula (I) to the citric acid ester surfactant formed in step (c).

With regard to preferred embodiments and possible combinations of preferred embodiments of the method according to the invention, the explanations given above for the use according to the invention and / or for the composition according to the invention apply correspondingly (if appropriate mutatis mutandis), and vice versa.

As the citric acid derivative prepared or prepared in step (b) of the above-described process of the present invention, a per se known such derivative may be used, for example, a hydrate, or a salt of one, two, or all three citric acid carboxyl groups , depending on the particular desired degree of ester formation, ie depending on whether monoesters, diesters, triesters or mixtures of such esters are to be produced.

The reaction in step (c) of the abovementioned process according to the invention can be carried out in a manner known per se for the formation of esters from alcohols and carboxylic acids (or carboxylic acid derivatives).

The step (d) of the above-mentioned method according to the invention, the adding, can take place immediately after the preceding step (c), or further steps can be carried out after step (c) before step (d) is carried out. Further steps after step (c) include, for example, purification, concentration or dilution of citric acid surfactant obtained in step (c) or addition of further ingredients, such as surfactants, fragrances, thickeners and the like.

Also preferred is a process according to the invention, wherein the reaction in step (c) comprises reacting the citric acid or its derivative suitable for esterification with one or more ethoxylated alcohols of the formula (II) from step (a) in one step with an ethoxylated alcohol of the Formula (II) from step (a), or in one step, with a plurality of ethoxylated alcohols of the formula (II) from step (a), particularly preferably with a mixture of ethoxylated alcohols of the formula (II) from step (a), or in several successive steps, preferably with a plurality of ethoxylated alcohols of the formula (II) from step (a).

Particular preference is given to a preferred process according to the invention or one described above or below, wherein the reaction in step (c) comprises reacting the citric acid or its derivative suitable for esterification with a plurality of ethoxylated alcohols of the formula (II) from step (a) in one step , preferably with a mixture of ethoxylated alcohols of the formula (II) from step (a). In this embodiment of the process according to the invention, preference is given to using a mixture of ethoxylated alcohols of the formula (II) which has been formed or prepared from a mixture of alcohols, in particular from a mixture of technical fatty alcohols (as indicated above).

The invention also relates to a process for improving the foam properties of a citric acid ester surfactant comprising one or more esters of citric acid with one or more ethoxylated alcohols of the formula (II) and / or a further process for the preparation of an inventive or preferred foamable composition according to the invention described above, comprising the steps

(aa) providing or preparing a citric acid ester surfactant comprising one or more esters of citric acid with one or more ethoxylated alcohols of the formula (II)

R ² -O (CH ₂ CH ₂ -O) n H (II) wherein

R ^{2 is} an unbranched or branched alkyl group having a total of 6 to 22 carbon atoms or an unbranched or branched alkenyl group having a total of 6 to 22 carbon atoms and n is an integer in the range of 1 to 50, (bb) providing or preparing at least one 1, 2 Alkanediols of the formula (I)

R ^{1 is} -CH (OH) -CH ₂ -OH (I) wherein

R ^{1 is} an unbranched or branched, preferably unbranched, alkyl group having a total of 6 to 12, preferably having a total of 6 to 10, more preferably having a total of 6 to 8, carbon atoms, and

(cc) mixing together the ingredients respectively provided or prepared in steps (aa) and (bb).

With regard to preferred embodiments and possible combinations of preferred embodiments of the method according to the invention for improving the foam properties of a citric acid ester surfactant and / or the inventive further method for producing a foamable composition according to the invention or above, the above-mentioned for the inventive use, for the inventive composition and / or o- for the inventive method for producing an above-mentioned

Explanations given according to the invention or preferred foamable composition according to the invention (if appropriate, mutatis mutandis), and vice versa.

The present invention also relates to a foamable composition which can be prepared or prepared by a preferred process according to the invention or a process described above and / or by a further process according to the invention described above.

With regard to preferred embodiments and possible combinations of preferred embodiments of the composition which can be prepared or prepared according to the invention, the explanations given above for the use according to the invention, the composition according to the invention and / or for the method according to the invention apply correspondingly (if appropriate mutatis mutandis), and vice versa.

The present invention also relates to a washing, cleaning and / or care agent comprising a foamable composition according to the invention and / or a foamable composition which can be prepared or prepared according to the invention.

With regard to preferred embodiments and possible combinations of preferred embodiments of the inventive washing, cleaning and / or care agent, the explanations given above for the inventive use, the composition according to the invention and / or for the method according to the invention or inventive method apply correspondingly (if appropriate mutatis mutandis), and vice versa.

In the context of the present invention, washing, cleaning and / or care agents are, for example, detergents, preferably hand detergents, dishwashing detergents, preferably hand dishwashing detergents and personal care products such as shampoos, conditioners for skin and / or hair, shower baths or Bath additives in question.

Detergents, cleaners and / or care agents according to the invention may contain, in addition to the foamable compositions according to the invention, further constituents, preferably further surfactants, fragrances, dyes, pigments, rheology additives, stabilizers and / or preservatives.

Characters:

Figures 1 -1 to 1-6 show pattern views for the evaluation or assessment of foam qualities according to Example 2:

Fig. 1-1: Foam quality very good (1), fine-pored, no large air bubbles visible Fig. 1-2 Foam quality good (2), essentially fine-pored, a few larger air bubbles visible;

Fig. 1-3: Foam quality satisfactory (3), partly fine-pored, some larger air bubbles visible, a few large air bubbles;

Fig. 1-4: foam quality sufficient (4), more larger air bubbles than fine-pored

Foam, a few big bubbles;

Fig. 1-5: Foam quality not sufficient (5), larger air bubbles clearly in the

Plurality, few large bubbles;

Fig. 1-6: Foam quality poor (6), almost without exception larger and larger air bubbles. Examples:

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

The influence of 1,2-alkanediols of the formula (I) on the foam properties (foam height, foam quality) of a citric acid ester surfactant to be used according to the invention was determined according to the following test methods:

Example 1: Determination of the foam height

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, 2.5 g of a citric acid ester surfactant (Plantapon® LC7, BASF SE) to be used according to the invention were weighed in a 800 ml beaker (Schott Duran, H: 13.5 cm, R: 9.4 cm) using a stirrer, and mixed with 50 ml of tap water. For each test, the 1,2-alkanediol indicated in Table 1 was added to this template in each case also indicated in Table 1. 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 total volume and then heated to 30 ° C (water bath). The resulting tempered mixture was then stirred for 10 seconds (stopwatch) to generate foam with an agitator (see above) at a speed of 2000 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 are given below in Table 1.

Example 2: Determination of foam quality

Immediately following the determination of the foam height (see Example 1), a sample of the resulting foam was removed with a spoon, applied to a dark background, and the foam quality was visually rated on a scale of 1 to 6 ("1 very good," 6 ": poor foam quality, see above). Examples of the evaluation of foam qualities are shown in the accompanying drawings (Figs. 1-1 to 1-6). The standard (SQ = 2) used was the commercially available surfactant Texapon® NSO (sodium lauryl ether sulfate).

The results of this test, given as foam qualities "SQ", in values from 1 to 6 (averages of four measurements) for different 1,2-alkanediols are shown below in

Table 1 listed.

Table 1: Influence of 1,2-alkanediols on foam properties of a citric acid ester surfactant (Plantapon® LC7)

nb: value not determined

From the results given in Table 1 it can be seen that the achievable under the experimental conditions foam height of the citric acid ester surfactant used by addition of 1, 2-octanediol or 1, 2-decanediol could be significantly improved (increased). The strongest improvement was achieved with 1, 2-decanediol. Furthermore, it can be seen from the results given in Table 1 that the foam quality of the citric acid ester surfactant used can be significantly improved by the addition of 1,2-octanediol, 1,2-decanediol or 1,2-dodecanediol. The strongest improvements were achieved with 1, 2-octanediol and 1, 2-decanediol.

Claims

claims:

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

R ^{1 is} -CH (OH) -CH ₂ -OH (I) in which R ^{1 is} an unbranched or branched alkyl group having a total of 6 to 12 carbon atoms, as a foam enhancer and / or foam improver for a citric acid ester surfactant which contains one or more esters of citric acid with one or more ethoxylated alcohols of the formula (II) R ² -O (CH ₂ CH ₂ -O) n H (II), in which

2. Use according to claim 1, wherein the ester or esters of citric acid are esters which can be prepared by esterification of citric acid with one or more ethoxylated alcohols of the formula (II).

3. Use according to one of the preceding claims, wherein

in which one or at least one of a plurality of 1, 2-alkanediols of the formula (I) R ^{1 is} an unbranched or branched, preferably unbranched, alkyl group having a total of 6 to 10 carbon atoms, and preferably one or at least one of several 1, 2 Alkanediols of the formula (I) is selected from the group consisting of n-1, 2-octanediol, n-1, 2-decanediol and n-1, 2-

Dodecanediol.

4. Use according to one of the preceding claims, wherein in the one or at least in one of a plurality of 1, 2-alkanediols of the formula (I) R ^{1 is} an unbranched or branched, preferably unbranched, alkyl group having a total of 6 to 8 carbon atoms and preferably one or at least one of a plurality of 1,2-alkanediols of the formula (I) is selected from the group consisting of n-1, 2-octanediol and n-1, 2-decanediol.

5. Use according to one of the preceding claims, wherein the or the 1, 2-AI kandiole of the formula (I) are used in a foam-enhancing and / or foam-improving effective amount, preferably in a total amount in the range of 5 wt .-% to 40 wt .-%, particularly preferably in the range of 10 wt .-% to 30 wt .-%, based on the total mass of the citric acid ester surfactant contained in the composition.

6. Use according to one of the preceding claims, wherein in the one or at least in one of a plurality of ethoxylated alcohols of the formula (II) n is an integer in the range of 1 to 20, preferably in the range of 1 to 10 and particularly preferably in the range of 3 to 8, means and / or

R ^{2 is} a straight or branched alkyl group having a total of 8 to 20, preferably a total of 10 to 20, particularly preferably having a total of 12 to 18, carbon atoms or an unbranched or branched alkenyl group having a total of 8 to 20, preferably a total of 10 to

20, more preferably having a total of 12 to 18, carbon atoms.

7. Use according to one of the preceding claims, wherein the citric acid ester surfactant comprises a mixture of several esters of citric acid with one or more ethoxylated alcohols of the formula (II), wherein the ethoxylated alcohols of the formula (II) preferably comprise mixtures of technical fatty alcohols.

Use according to any of the preceding claims, preferably according to claim 6, wherein the citric acid ester surfactant comprises one or more constituents selected from the group consisting of monoesters and diesters of citric acid with ethoxylated alcohols of formula (II), preferably in a total amount in the range of 50 Wt .-% to 90 wt .-%, particularly preferably in the range of 60 wt .-% to 80 wt .-%, based on the total mass of the citric acid ester surfactant.

A foamable composition comprising - one or more 1,2-alkanediols of the formula (I)

R ^{1 is} -CH (OH) -CH ₂ -OH (I) wherein

a citric acid ester surfactant comprising one or more esters of citric acid with one or more ethoxylated alcohols of the formula (II) R ² -O (CH ₂ CH ₂ -O) n H (II) wherein

R ^{2 is} an unbranched or branched alkyl group having a total of 6 to 22 carbon atoms or an unbranched or branched alkenyl group having a total of 6 to 22 carbon atoms and n is an integer in the range of 1 to 50.

A composition according to claim 9, wherein in said one or at least one of said plurality of 1,2-alkanediols of formula (I), R 1 is an unbranched hydrocarbon group having a total of 6 to 10 carbon atoms and preferably one or more of 1, 2 Alkanediol of the formula (I) is selected from the group consisting of n-1, 2-octanediol, n-1, 2-decanediol and n-1, 2-dodecanediol.

A composition according to any one of claims 9 or 10, wherein in said one or at least one of said plurality of 1,2-alkanediols of formula (I) R 1 is an unbranched hydrocarbon group having a total of 6 to 8 carbon atoms and preferably one or at least one of several 1,2-alkanediols of

Formula (I) is selected from the group consisting of n-1, 2-octanediol and n-1, 2-decanediol.

12. The composition according to any one of claims 9 to 11, wherein

- The composition is foamable in contact with water, and / or

- The composition is at least in a ratio of 1: 4 (w / w) miscible with water.

13. A composition according to any one of claims 9 to 12, wherein

the total amount of the one or more 1,2-alkanediols of the formula (I) in the range from 5% by weight to 40% by weight, preferably in the range from 10% by weight

% to 30 wt .-%, is based on the total mass of the citric acid ester surfactant contained in the composition, and / or

the total amount of the one or more 1,2-alkanediols of the formula (I) in the range from 0.1% by weight to 30% by weight, preferably in the range from 0.2% by weight.

% to 25 wt .-%, more preferably in the range of 0.25 wt .-% to 10 wt .-%, based on the total mass of the composition.

14. A process for preparing a composition according to any one of claims 9 to 13, comprising the steps of: (a) providing or preparing one or more ethoxylated alcohols of

Formula (II)

R ² -O (CH ₂ CH ₂ -O) n H (II) wherein

R ^{2 is} an unbranched or branched alkyl group having a total of 6 to 22 carbon atoms or an unbranched or branched alkenyl group having a total of 6 to 22 carbon atoms and n is an integer in the range from 1 to 50,

(c) reacting the one or more ethoxylated alcohols of formula (II) from step (a) with citric acid or its derivative suitable for esterification under conditions which allow esterification to give a citric acid ester surfactant, (d) adding a foam-boosting and / or or foam-improving amount of one or more 1, 2-alkanediols of the formula (I) to the citric acid ester surfactant formed in step (c).

15. The method of claim 14, wherein reacting in step (c) comprises reacting the citric acid or its derivative suitable for esterification with one or more ethoxylated alcohols of formula (II) from step (a) in one step with an ethoxylated one Alcohol of the formula (II) from step (a), or in one step, with a plurality of ethoxylated alcohols of the formula (II) from step (a), more preferably with a mixture of ethoxylated alcohols of the formula (II) from step (a), or in several successive steps, preferably with a plurality of ethoxylated alcohols of the formula (II) from step (a).

16. The method according to any one of claims 14 or 15, wherein the esterification suitable derivative of citric acid is selected from the group consisting of a hydrate of citric acid, a salt of a citric acid carboxyl group, a salt of two citric acid carboxyl groups and a salt of three citric acid carboxyl groups.

17. A process for improving the foam properties of a citric acid ester surfactant comprising one or more esters of citric acid with one or more ethoxylated alcohols of the formula (II) and / or processes for the preparation thereof

A composition according to any one of claims 9 to 13, comprising the steps

R ² -O (CH ₂ CH ₂ -O) n H (II) wherein

(bb) providing or preparing at least one 1,2-alkanediol of the formula (I)

R ^{1 is} -CH (OH) -CH ₂ -OH (I), where R ^{1 is} an unbranched or branched, preferably unbranched, alkyl group having a total of 6 to 12, preferably 6 to 10, more preferably 6 to 8 in total, Carbon atoms, and (cc) mixing the ingredients respectively prepared or prepared in steps (aa) and (bb) with each other.

18. Foamable composition, preparable or prepared by a process according to one of claims 14 to 17.

19. Washing, cleaning and / or care compositions containing a foamable composition according to one of claims 9 to 13 and / or according to claim 18.