Process for preparing compositions comprising carboxyalkylated alkyl and / or alkenyl glycosides and compositions obtainable by process

Abstract

The present invention provides a process for the preparation of a composition comprising at least one carboxyalkylated alkyl glycoside and / or alkenyl glycoside (component (a)), wherein the process comprises the steps of: i) providing in a reactor at least one alkyl glycoside and / or alkenyl glycoside of formula (I) (component (b)); the present invention relates to a process for the preparation of halogenated carboxylic acids, comprising the steps of i) adding a halogenated carboxylic acid, a salt or ester thereof, ii) adding a halogenated carboxylic acid, a salt or ester thereof, iii) adding an alkaline agent, in which step ii) comprises iii ') initially feeding 0.3 wt.% to 50 wt.%, preferably 0.5 wt.% to 25 wt.%, more preferably 1 wt.% to 10 wt.%, of the total amount of halogenated carboxylic acid, a salt or ester thereof added in step (ii), and stirring until it dissolves, and ii') feeding the remaining halogenated carboxylic acid, a salt or ester thereof.

Description

Technical Field

[0001] This invention relates to a method for preparing a composition comprising one or more carboxyalkylated alkyl glycosides and / or alkenyl glycosides, to a composition obtainable by such a method, to a cosmetic composition comprising the composition, and to the use of said cosmetic composition in hair and / or skin cleansing applications. Background Technology

[0002] Skin and hair cleansing compositions are required not only to have good detergency and cleansing power, but also to be gentle and well-tolerated by skin and / or hair, without causing excessive degreasing or drying. They should also have reduced viscosity, be uniform, easy to apply, and exhibit good foaming properties, such as foam stability, foam quantity, foam quality, and foam smoothness. Furthermore, consumers demand that skin and hair cleansing compositions exhibit good viscosity and rheological properties such as stability, feel, and flowability. Additionally, there is a focus on the sustainability of cosmetics in the consumer product market. Therefore, it is also necessary to formulate products containing ingredients that are considered "green" or "natural" because they are derived from renewable and / or sustainable sources.

[0003] Another requirement for cosmetic ingredients is to reduce their environmental footprint from manufacturing to their use as cosmetic ingredients. Therefore, obtaining more concentrated liquid products, and thus with lower water content, is associated with reduced energy consumption because less water is transported. Furthermore, the reduced water content makes it possible to reduce the need for preservatives, as the low water content of concentrated products generally makes them unsuitable as a medium for microbial growth.

[0004] The preparation and use of anionic surfactants in skin and hair cleansing formulations are well known to those skilled in the art.

[0005] EP1436306 describes an aqueous surfactant mixture comprising alkyl oligosaccharide ether carboxylic acids and / or alkenyl oligosaccharide ether carboxylic acids. This patent application describes a method for preparing the surfactant by reacting alkyl oligosaccharides and / or alkenyl oligosaccharides with ω-halocarboxylic acids or their salts or esters.

[0006] EP1385612 describes the use of a surfactant composition containing a surfactant mixture having alkyl oligosaccharides and / or alkenyl oligosaccharides and alkyl oligosaccharide ether carboxylic acids and / or alkenyl oligosaccharide ether carboxylic acids. This patent application describes an aqueous composition wherein both foaming and viscosity requirements are met.

[0007] WO2021108518 describes citrate-functionalized alkyl polyglucoside derivatives prepared by the reaction of epichlorohydrin / citrate with alkyl polyglucosides. The patent also describes the use of functionalized alkyl polyglucosides as thickeners and anti-irritants in personal care cleaning products.

[0008] As can be seen from the above-mentioned prior art, there is still a need for other compositions containing carboxyalkylated alkyl glycosides and / or alkenyl glycosides for skin and / or hair cleaning. Summary of the Invention

[0009] The present invention aims to address the above-mentioned needs and provides a method for preparing a composition comprising at least one carboxylated alkyl glycoside and / or alkenyl glycoside compound; a composition obtainable by such preparation method; and the use of the composition in cosmetic applications such as skin and / or hair cleansing.

[0010] The composition meets the requirements for application and provides good performance.

[0011] The relevant properties of the carboxyalkylated alkyl glycosides and / or alkenyl glycosides of the present invention are ease of user handling, low residual salt content, low water content, and low color grade. In particular, the compositions of the present invention exhibit good viscosity, good stability, good hand feel and flow rheological properties, and good foaming properties, such as foam stability, foam volume, foam quality, and foam smoothness. The compositions of the present invention can also be obtained with higher dry content substances, thereby reducing their water content.

[0012] The compositions of the present invention also have good detergency and cleaning power; they are mild, well tolerated by skin and / or hair, do not cause excessive degreasing or drying of skin and hair, exhibit reduced tackiness, are uniform, and are easy to apply.

[0013] The inventors have developed a method that can impart or enhance at least some of the advantageous properties found in the compositions of the present invention.

[0014] Therefore, a first aspect of the present invention relates to a method for preparing a composition comprising at least one carboxylated alkyl glycoside and / or alkenyl glycoside.

[0015] In a second aspect of the invention, a composition is provided that can be obtained by methods as defined in the first aspect of the invention.

[0016] Cosmetic compositions comprising compositions as defined in the first and / or second aspects of the present invention are also an aspect of the present invention.

[0017] Another aspect of the invention is the use of any of the compositions provided by the invention for the care of skin and / or hair, particularly for the cleansing of skin and / or hair. This aspect can also be described as a method of cleansing or conditioning skin and / or hair with any of the compositions of the invention, the method comprising applying the composition to the skin and / or hair.

[0018] Another aspect of the present invention is a method for preparing a cleaning composition. Detailed Implementation

[0019] Terms not specifically defined herein should be given the meanings that those skilled in the art would assign to them based on this disclosure and the context. However, as used herein, unless otherwise stated, the following terms have the meanings indicated and follow the conventions described below.

[0020] Throughout this specification and the accompanying terms, the word “comprise” and variations thereof, such as “comprises” and “comprising”, shall be construed as inclusive. That is, where the context permits, these words are intended to convey that other elements or wholes not specifically described may be included. The word “comprise” also includes the term “composed of”.

[0021] For the purposes of this invention, any range given includes both the lower and upper limits of that range.

[0022] Unless otherwise stated, all percentages are by weight.

[0023] As a cosmetic composition, it should be understood as a composition suitable as an ingredient for use in cosmetic and personal care applications, particularly for skin and hair care.

[0024] The main objective of this invention is a method for preparing a composition comprising:

[0025] At least one carboxylated alkyl glycoside and / or alkenyl glycoside compound.

[0026] The terms “alkyl glycoside compound” and “alkenyl glycoside compound” refer to a sugar moiety (i.e., a sugar, which may be a monosaccharide or an oligosaccharide) that is derived by forming an ether bond by bonding one of its hydroxyl groups to an alkyl or alkenyl group, and wherein the remaining one or more hydroxyl groups of the sugar moiety are each bonded to a moiety that contains at least a halocarboxylic acid group or a salt thereof.

[0027] A method for preparing a composition comprising at least one component (a) (i.e., a carboxyalkylated alkyl glycoside and / or an alkenyl glycoside), comprising: in a first step, providing at least one alkyl glycoside and / or alkenyl glycoside of formula (I) (hereinafter also referred to as component (b)) in a reactor.

[0028] R1-[G] p Formula (I).

[0029] Alkyl glycosides and / or enyl glycosides (component (b)):

[0030] According to the present invention, the method for preparing carboxyalkylated alkyl glycosides and / or alkenyl glycosides comprises providing at least one alkyl glycoside and / or alkenyl glycoside of formula (I).

[0031] R1-[G] p Formula (I)

[0032] R1 represents an alkyl or alkenyl group having 4 to 24 carbon atoms, preferably 10 to 18 carbon atoms, more preferably 10 to 16 carbon atoms, and even more preferably 12 to 16 carbon atoms;

[0033] The G group is a sugar unit containing 5 or 6 carbon atoms, preferably glucose.

[0034] The R1 moiety is bonded to sugar unit G via an ether bond between R1 and a hydroxyl group of sugar unit G; when p>1, the bond between two G groups (-GG-) indicates the formation of a glycosidic bond (i.e., an ether bond between a hydroxyl group in one sugar unit G and a hydroxyl group in another sugar unit G) (as in any disaccharide, this results in one sugar unit G losing a hydrogen atom and the other sugar unit G losing a hydroxyl group).

[0035] Alkyl glycosides or alkenyl glycosides can be derived from aldoses or ketoses containing 5 or 6 carbon atoms, i.e., G is a sugar unit derived from aldoses or ketoses containing 5 or 6 carbon atoms.

[0036] Examples of aldoses containing 5 or 6 carbon atoms include ribose, arabinose, xylose, lythose, and glucose. Examples of ketoses containing 5 or 6 carbon atoms include ribulose, xylulose, fructose, psocose, sorbose, and tagatose.

[0037] Preferably, the alkyl glycoside or alkenyl glycoside is derived from glucose, i.e., G is glucose.

[0038] The exponent p in the formula indicates the degree of oligomerization (i.e., the number of glycosidic units, i.e., monosaccharides and oligosaccharides), and the number of p is from 1 to 10. Although p in a given compound must always be an integer, preferably, p can be assumed to be a value from 1 to 6, the p value of a particular alkyl glycoside and / or alkenyl glycoside is a number determined by analysis obtained by gas chromatography, which is generally not an integer but has decimal places. The determination of the degree of oligomerization can be obtained according to methods conventional and well known to those skilled in the art. Those skilled in the art will also recognize that using one method or another will yield substantially the same degree of oligomerization. Therefore, in the context of this invention, "p" also covers "average degree of oligomerization," which can be determined as described below. In one embodiment, the at least one alkyl glycoside and / or alkenyl glycoside has an average degree of oligomerization p of 1.1 to 3.0.

[0039] In one embodiment of the invention, R1 is a straight-chain alkyl or branched alkyl group having 4 to 24 carbon atoms or a straight-chain alkenyl group having 4 to 24 carbon atoms and 1 to 3 double bonds; preferably, the alkyl or alkenyl group has 10 to 18 carbon atoms, more preferably 10 to 16 carbon atoms, and even more preferably 12 to 16 carbon atoms.

[0040] As used herein, the term "alkyl" refers to a straight-chain or branched hydrocarbon chain having a specified number of carbon atoms, preferably 4 to 24 carbon atoms, more preferably 10 to 18 carbon atoms, more preferably 10 to 16 carbon atoms, and even more preferably 12 to 16 carbon atoms.

[0041] As used herein, the term "alkenyl" refers to a linear hydrocarbon chain having a specified number of carbon atoms, preferably 4 to 24 carbon atoms, more preferably 10 to 18 carbon atoms, even more preferably 10 to 16 carbon atoms, and even more preferably 12 to 16 carbon atoms and 1 to 3 double bonds (i.e., 1, 2 or 3 double bonds).

[0042] Illustrative and non-limiting examples of the R1 group are decyl, octyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl, hexadec-9-en-1-yl, octadecyl, 16-methylheptadecyl-1-yl, octadec-9-en-1-yl, octadec-9,12-dien-1-yl, octadec-6-en-1-yl, docosyl, and docosyl-13-en-1-yl.

[0043] In a preferred embodiment of the present invention, R1 is selected from dodecyl and tetradecyl.

[0044] In one embodiment of the invention, the alkyl glycoside and / or alkenyl glycoside of formula (I) is a glycoside wherein R1 is a straight-chain alkyl chain having 10 to 16 carbon atoms, G represents glucose, and the number of p is 1 to 3. In a preferred embodiment of the invention, the alkyl glycoside and / or alkenyl glycoside of formula (I) is caprylyl / capryl glycoside, myristyl glycoside, lauryl glycoside, cocoyl glycoside, or a combination thereof. In a more preferred embodiment, the alkyl glycoside and / or alkenyl glycoside of formula (I) is lauryl glycoside. In another preferred embodiment of the invention, the alkyl glycoside and / or alkenyl glycoside of formula (I) is D-glucanopyranose, oligomeric, or C10-16-alkyl glycoside.

[0045] In another embodiment of the invention, the alkyl glycosides and / or alkenyl glycosides are derived from natural sources (i.e., from plants or vegetables).

[0046] Obtaining the alkyl glycosides and / or alkenyl glycosides of formula (I) is well known in the art. The articles by Biermann et al. in Starch / Stärke 45, 281 (1993) and J. Kahre et al. in SÖFW Journal No. 8, 598 (1995) are representative of a large body of literature on this component.

[0047] Preparation method of the composition:

[0048] The method for preparing a composition comprising a carboxyalkylated alkyl glycoside and / or an alkenyl glycoside compound (component (a)) according to the present invention includes the following steps:

[0049] i) Provide at least one alkyl glycoside and / or alkenyl glycoside of formula (I) in the reactor (component (b))

[0050] R 1 -[G] p Formula (I)

[0051] R1, G, and p are defined as above.

[0052] ii) Add halocarboxylic acids, their esters, or salts to the reactor.

[0053] iii) Add an alkaline reagent.

[0054] Step ii) includes

[0055] ii') The initial feed is intended to be 0.3 wt.% to 50 wt.%, preferably 0.5 wt.% to 25 wt.%, more preferably 1 wt.% to 10 wt.%, of the total amount of the halocarboxylic acid, its salt, or ester added in step (ii), and stirred until dissolved; subsequently,

[0056] ii) Feed the remaining halocarboxylic acids, their salts or esters.

[0057] In the context of this invention, the term "halocarboxylic acid" refers to a saturated or unsaturated hydrocarbon chain having 1 to 10 carbon atoms, comprising one or more carboxyl groups (-COOH), wherein a halogen atom replaces a hydrogen atom in the hydrocarbon chain.

[0058] In one embodiment of the present invention, the halocarboxylic acid has formula (II).

[0059] A-(CH2) m -COOX formula (II)

[0060] Where A represents halogen, m is 1 to 5, and X is selected from hydrogen, alkali metals, ammonium and alkaline earth metals.

[0061] The "ester" or "salt" of organic acid used in the context of this invention can be obtained according to conventional synthetic methods used by those skilled in the art.

[0062] In another embodiment of the invention, the reaction between the alkyl glycoside and / or alkenyl glycoside of formula (I) and the halocarboxylic acid, its salt or ester is a carboxyl alkylation reaction.

[0063] In one embodiment of the invention, steps ii) and iii) are added simultaneously, particularly at a constant speed.

[0064] The term "constant rate" means ensuring that reagents (i.e., halocarboxylic acids, their salts or esters, and basic reagents) are added independently in substantially the same amount throughout the reaction time until the addition step is complete.

[0065] In another embodiment, the halocarboxylic acid, its salt or ester, and the basic reagent from step iii) are fed into the reaction independently at a constant rate. "Independently fed" should be understood as the halocarboxylic acid, its salt or ester, and the basic reagent being added to the reactor in an independent manner (i.e., through separate inlets).

[0066] In another embodiment, the halocarboxylic acid, its salt or ester from step ii), and the basic reagent from step iii) are added to the reactor at a constant rate over a period of 4 to 6 hours, preferably 4.5 to 5.5 hours.

[0067] In another embodiment, the reaction temperature is 40°C to 90°C, preferably 40°C to 80°C, and more preferably 40°C to 70°C.

[0068] In one embodiment of the invention, the method further includes step iv), wherein after steps ii') and iii), the reaction mixture is kept in the reactor for 3 to 5 hours under constant stirring.

[0069] In another embodiment, the temperature in step iv) is 40°C to 100°C, preferably 50°C to 95°C, more preferably 60°C to 95°C.

[0070] In one embodiment of the invention, the molar ratio between the halocarboxylic acid, its salt or ester and the alkyl glycoside and / or alkenyl glycoside of formula (I) is 0.8:1 to 3:1, preferably 0.9:1 to 2:1, more preferably 0.9:1 to 1.25:1, and even more preferably 0.9:1 to 1.2:1.

[0071] In one embodiment of the invention, the molar ratio between the alkaline reagent and the halocarboxylic acid, its salt or ester is 1:1.05 to 1:1.1, preferably 1:1.01 to 1:1.05, more preferably 1:1 to 1.1:1.01.

[0072] In one embodiment of the invention, the halocarboxylic acid, its salt or ester is a salt of monochloroacetic acid, preferably sodium monochloroacetate.

[0073] In another embodiment, the carboxyalkylated alkyl glycoside and / or alkenyl glycoside compound (component (a)) is a carboxymethylated alkyl glycoside and / or alkenyl glycoside compound.

[0074] In another embodiment, the salt of monochloroacetic acid is in solid form.

[0075] In one embodiment of the invention, the alkaline reagent is an alkali metal hydroxide or an alkaline earth metal hydroxide, such as sodium hydroxide, potassium hydroxide, magnesium hydroxide, lithium hydroxide, or barium hydroxide. Preferably, the alkaline reagent is selected from sodium hydroxide, potassium hydroxide, and mixtures thereof.

[0076] In another embodiment, the alkaline reagent is added in solid form.

[0077] In another embodiment of the invention, the degree of conversion of the carboxyalkylated alkyl glycoside and / or alkenyl glycoside is 30% to 80%, preferably 35% to 70%, and more preferably 40% to 60%.

[0078] The conversion degree is calculated as the molar number of carboxyalkylated alkyl glycosides and / or alkenyl glycosides divided by the initial molar number of alkyl glycosides and / or alkenyl glycosides.

[0079] The composition produced by the reaction comprises carboxyalkylated alkyl glycosides and / or alkenyl glycosides (component (a)), unreacted substances in the method of obtaining carboxyalkylated alkyl glycosides and / or alkenyl glycosides (e.g., alkyl glycosides and / or alkenyl glycosides of formula (I), esters), impurities or byproducts from the same reaction (e.g., sodium glycolate, sodium diethanolate, haloacetic acid), and inorganic salts (e.g., sodium chloride) and water.

[0080] In one embodiment of the invention, the alkyl glycosides and / or alkenyl glycosides of formula (I) correspond to the non-derivative species obtained from the carboxyalkylated alkyl glycosides and / or alkenyl glycoside compounds (component (a)).

[0081] In another embodiment, the alkyl glycosides and / or alkenyl glycosides of formula (I) are different from the corresponding non-derivative species obtained from the carboxyalkylated alkyl glycosides and / or alkenyl glycoside compounds (component (a)). In this embodiment, the alkyl glycosides and / or alkenyl glycosides of formula (I) are added to the reaction medium in a separate step (before or after any of the above steps that form part of the method of the present invention).

[0082] In one embodiment of the present invention, the method further comprises adding a preservative, such as sorbic acid, sodium benzoate, or potassium sorbate; preferably sorbic acid.

[0083] In another embodiment of the invention, the method further includes adding a pH adjuster, such as citric acid, lactic acid, acetic acid, hydrochloric acid, sulfuric acid, or phosphoric acid; preferably citric acid.

[0084] In one embodiment of the present invention, a method for preparing a composition comprising carboxymethylated alkyl glycosides and / or alkenyl glycoside compounds (component (a)) includes the following steps:

[0085] i) Providing alkyl glycosides and / or alkenyl glycosides of formula (I) in the reactor,

[0086] ii') The initial feed is preferably 0.5% to 25%, more preferably 1% to 10%, of the halocarboxylic acid, its salt, or ester to be added in step (ii), and stirred until dissolved, subsequently,

[0087] ii) Feed the remaining halocarboxylic acids, their salts or esters.

[0088] iii) Add an alkaline reagent;

[0089] iv) Maintain the reaction mixture in the reactor for 3 to 5 hours while continuously stirring;

[0090] in:

[0091] The additions in steps ii) and iii) are carried out simultaneously, specifically at a constant rate; specifically, the halocarboxylic acid, its salt or ester, from step ii) and the basic reagent from step iii) are added to the reactor simultaneously but separately; more specifically,

[0092] The halocarboxylic acid, its salt or ester from step ii'), and the basic reagent from step iii) are fed into the reaction independently.

[0093] In one embodiment of the present invention, a method for preparing a composition comprising carboxymethylated alkyl glycosides and / or alkenyl glycoside compounds (component (a)) includes the following steps:

[0094] i) Providing alkyl glycosides and / or alkenyl glycosides of formula (I) in the reactor,

[0095] ii') The initial feed of halocarboxylic acid, its salt or ester is preferably 0.5% to 25%, more preferably 1% to 10%, and stirred until it is completely dissolved;

[0096] ii) Feed the remaining halocarboxylic acids, their salts or esters;

[0097] v) Add an alkaline reagent;

[0098] vi) Maintain the reaction mixture in the reactor at a temperature of 85°C to 95°C for 3 to 5 hours while continuously stirring;

[0099] in:

[0100] The addition of steps ii) and iii) is carried out simultaneously, particularly at a constant rate; in particular, the halocarboxylic acid, its salt or ester from step ii) and the basic reagent from step iii) are added to the reactor simultaneously but separately; more particularly, the halocarboxylic acid, its salt or ester from step ii') and the basic reagent from step iii) are fed into the reaction independently.

[0101] The reaction temperature is 40℃ to 70℃;

[0102] The halocarboxylic acid, its salt or ester is sodium monochloroacetate;

[0103] The alkaline reagent is sodium hydroxide;

[0104] The alkyl glycoside and / or alkenyl glycoside of formula (I) is a glycoside in which R1 is a straight-chain alkyl chain having 10 to 16 carbon atoms, G represents a glucose unit, and the number of p is 1 to 3; the molar ratio between sodium monochloroacetate and the alkyl glycoside and / or alkenyl glycoside of formula (I) is 0.9:1 to 1.2:1, wherein the molar ratio between sodium hydroxide and sodium monochloroacetate is 1:1 to 1.1:1.01.

[0105] Compositions comprising at least one carboxylated alkyl glycoside and / or enyl glycoside, obtainable by the method of the present invention:

[0106] In another aspect of the invention, the invention provides a composition that can be obtained by the methods defined in any of the above embodiments, the composition comprising at least one carboxylated alkyl glycoside and / or alkenyl glycoside (component (a)).

[0107] For the purposes of this invention, the expressions “available,” “obtainable,” and equivalent expressions are used interchangeably, and in any case, the expression “available” encompasses the expression “obtainable.”

[0108] All embodiments of the method of the present invention provided above, especially the steps, reagents, conditions, ratios and %wt, are also applicable to embodiments of compositions that can be obtained by the method of the present invention.

[0109] Preferably, the composition obtained by the method of the present invention comprises at least one carboxylated alkyl glycoside or alkenyl glycoside (component (a)) in a weight percentage of 15 wt.% to 60 wt.%, preferably 20 wt.% to 55 wt.%, more preferably 30 wt.% to 55 wt.%, based on the total dry weight of the composition.

[0110] In another embodiment of the invention, the total amount of component (b) in the composition obtainable by the method of the invention is 15 wt.% to 60 wt.%, preferably 20 wt.% to 55 wt.%, more preferably 30 wt.% to 55 wt.%, relative to the total dry weight of the composition.

[0111] In a preferred embodiment, in the composition obtainable by the method of the present invention, the weight ratio of component (a):(b) is 0.6:1 to 3.5:1, preferably 0.5:1 to 2.5:1, and more preferably 0.5:1 to 1.5:1. In this embodiment, "weight of component (a)" refers to the total amount of one or more components (a) contained in the composition; and "weight of component (b)" refers to the total amount of one or more components (b) contained in the composition, both weights being expressed in the same unit.

[0112] In another embodiment, the composition obtained by the method of the present invention comprises:

[0113] - Component (a), having a weight percentage of 15 wt.% to 60 wt.%, preferably 20 wt.% to 55 wt.%, more preferably 30 wt.% to 55 wt.%, based on the total dry weight of the composition;

[0114] - The weight percentage of component (b) of formula (I) as defined in any of the above embodiments is 15 wt.% to 60 wt.%, preferably 20 wt.% to 55 wt.%, more preferably 30 wt.% to 55 wt.%, based on the total dry weight of the composition.

[0115] In a preferred embodiment of the present invention, the composition obtained by the method of the present invention comprises:

[0116] - Component (a), which is a carboxymethylated alkyl glycoside and / or alkenyl glycoside as defined in any of the above embodiments, has a weight percentage of 15 wt.% to 60 wt.%, preferably 20 wt.% to 55 wt.%, more preferably 30 wt.% to 55 wt.%, based on the total dry weight of the composition.

[0117] In another preferred embodiment, the composition obtained by the method of the present invention comprises:

[0118] - Component (a), which is a carboxymethylated alkyl glycoside and / or alkenyl glycoside as defined in any of the above embodiments, having a weight percentage of 15 wt.% to 60 wt.%, preferably 20 wt.% to 55 wt.%, more preferably 30 wt.% to 55 wt.%, based on the total dry weight of the composition; and

[0119] - The weight percentage of component (b) of formula (I) as defined in any of the above embodiments is 15 wt.% to 60 wt.%, preferably 20 wt.% to 55 wt.%, more preferably 30 wt.% to 55 wt.%, based on the total dry weight of the composition.

[0120] In one embodiment of the invention, the content of inorganic salts in the final product (i.e., the composition obtained by the method of the invention) is 6 wt.% to 25 wt.%, preferably 7 wt.% to 20 wt.%, and more preferably 7 wt.% to 16 wt.%, based on the total dry weight of the composition.

[0121] In one embodiment of the invention, the content of inorganic salts in the final product (i.e., the composition obtainable by the method of the invention) is less than 12 wt.%, preferably less than 11 wt.%, and more preferably less than 10 wt.%, based on the total dry weight of the composition.

[0122] In the context of this invention, the expression "total dry weight of the composition" means the weight of all components of the composition except water, which is determined by oven drying according to ISO 638.

[0123] In one embodiment of the present invention, the content of sodium glycolate as a reaction byproduct is 3 wt.% to 10 wt.%, preferably 4 wt.% to 9 wt.%, more preferably 4 wt.% to 7 wt.%, based on the total dry weight of the composition; the content of sodium diglycolate as a reaction byproduct is 0.2 wt.% to 7 wt.%, preferably 0.4 wt.% to 4 wt.%, more preferably 0.4 wt.% to 2 wt.%, based on the total dry weight of the composition.

[0124] Specifically, sodium glycolate and sodium diethanolate were determined by reversed-phase high-performance liquid chromatography (HPLC-UV) with a UV detector in gradient mode using an external standard calibration method.

[0125] Quantification was performed using analytical standards in the acidic form of both products.

[0126] In another embodiment, the content of monohaloacetic acid, particularly monochloroacetic acid, is less than 20 ppm based on the total dry weight of the composition.

[0127] In another embodiment, the content of dihaloacetic acid, particularly dichloroacetic acid, is less than 20 ppm based on the total dry weight of the composition.

[0128] Monochloroacetic acid and dichloroacetic acid were determined by ion chromatography coupled with a UV detector. Quantification was performed using external standard calibration with analytical standards for both products.

[0129] In another embodiment of the invention, the degree of conversion of the carboxyalkylated alkyl glycoside and / or alkenyl glycoside is 30% to 80%, preferably 35% to 70%, and more preferably 40% to 60%.

[0130] The conversion degree is calculated as the molar number of carboxyalkylated alkyl glycosides and / or alkenyl glycosides divided by the initial molar number of alkyl glycosides and / or alkenyl glycosides.

[0131] Specifically, unreacted alkyl glycosides and / or alkenyl glycosides were determined by reversed-phase high-performance liquid chromatography (HPLC-ELSD) in gradient mode with an evaporative light scattering detector. The sample was dissolved in a mixture of water and an organic solvent. The percentage of free alkyl glycosides and / or alkenyl glycosides was obtained by comparing the retention times of C12-C14 alkyl glycoside (oligomeric) standards using an external standard quantification method.

[0132] Specifically, the content of carboxyalkylated alkyl glycosides and / or alkenyl glycosides was determined by the difference between the dried residue and the sum of all other species. The percentage of polyglycoside alkyl carboxylic esters was subtracted from the result.

[0133] In another embodiment of the invention, the pH of the composition obtained by the method of the invention is 5 to 14, preferably 7 to 12.

[0134] In another embodiment, the color of the composition obtained by the method of the present invention is less than 200 (APHA), preferably less than 150 (APHA), and more preferably less than 100 (APHA).

[0135] Specifically, the color of the compositions was determined after adding 3% citric acid to each composition based on the total weight of the compositions. Measurements were taken 24 hours after preparation at 20°C and 35% dry content. Color was determined according to ISO 6271.

[0136] In another embodiment, the viscosity of the composition obtainable by the method of the present invention is measured at 20°C using a Brookfield LV viscometer 24 hours after preparation, and is 10 cP to 1700 cP, preferably 20 cP to 900 cP, more preferably 50 cP to 800 cP.

[0137] In another embodiment, the viscosity of the composition obtained by the method of the present invention is less than 500 cP, preferably less than 400 cP, more preferably less than 200 cP, and even more preferably less than 100 cP.

[0138] Cosmetic composition:

[0139] Another aspect of the present invention is a cosmetic composition comprising a composition obtainable by means of methods defined in any of the aspects and embodiments provided above, and one or more cosmetically acceptable excipients and / or carriers.

[0140] In one embodiment, the cosmetic composition comprises components (a) and (b), and water as an excipient.

[0141] In one embodiment of the present invention, the amount of carboxyalkylated alkyl glycosides and / or alkenyl glycoside compounds (i.e., component (a)) in the cosmetic composition of the present invention is 0.5 wt.% to 15 wt.%, preferably 1.2 wt.% to 10 wt.%, and even more preferably 2 wt.% to 10 wt.%, based on the total weight of the cosmetic composition.

[0142] In another embodiment of the invention, the amount of alkyl glycosides and / or alkenyl glycosides (i.e., component (b)) in the cosmetic composition is 0.5 wt.% to 30 wt.%, preferably 1.2 wt.% to 20 wt.%, more preferably 2 wt.% to 20 wt.%, based on the total weight of the cosmetic composition.

[0143] In one embodiment of the present invention, the cosmetic composition comprises:

[0144] -0.5 wt.% to 15 wt.%, preferably 1.2 wt.% to 10 wt.%, more preferably 2 wt.% to 10 wt.% of component (a)

[0145] -0.5 wt.% to 30 wt.%, preferably 1.2 wt.% to 20 wt.%, more preferably 2 wt.% to 20 wt.% of component (b)

[0146] The specified amounts are each expressed as a weight percentage of the mentioned component relative to the total weight of the cosmetic composition.

[0147] The cosmetic composition of the present invention may further comprise an additional component (c), said component being an amphoteric surfactant.

[0148] Amphoteric surfactant (c):

[0149] Examples of amphoteric surfactants are alkylamine oxides, alkyl betaines, alkyl sulfobetaines (sulfobetaine), amyl alkyl betaines, alkyl glycinates, alkyl carboxyglycinates, alkyl amphoteric acetates, alkyl amphoteric propions, alkyl amphoteric glycinates, alkyl amamidopropyl betaines, alkyl amamidopropyl- and hydroxysulfobetaines. Particularly preferred amphoteric surfactants are betaines, alkylamine oxides, alkyl amphoteric glycinates and alkyl amphoteric acetates.

[0150] In a preferred embodiment of the invention, component (c) comprises one or more amphoteric electrolytes. Specific examples of amphoteric electrolytes are amine oxides. Suitable amine oxides according to the invention are amine oxides having a hydrocarbon chain containing 8 to 18 carbon atoms. Examples of commercially available amine oxides are those with the following commercial designations: OXIDET® DM-20 (INCI name: Lauream Oxide), OXIDET® DMCLD (INCI name: Coconut Oil Amine Oxide), OXIDET® DM-246 (INCI name: Coconut Oil Amine Oxide), OXIDET® DM-4 (INCI name: Myristate Amine Oxide), and OXIDET® L-75 (INCI name: Cocamidopropyl Amine Oxide), all of which are sold by KAO Chemicals Europe.

[0151] In the most preferred embodiment of the invention, component (c) comprises one or more betaines. Specific examples of betaines are alkyl betaines, alkyl sulfonyl betaines (sulfonyl betaines), amyl alkyl betaines, alkyl glycinates, alkyl carboxyglycinates, alkyl amphoteric acetates, alkyl amphoteric propionates, alkyl amphoteric glycinates, alkyl amamidopropyl betaines, and hydroxysulfonyl betaines. Particularly preferred betaines are alkyl amamidopropyl betaines, alkyl amamidopropyl hydroxysulfonyl betaines, alkyl hydroxysulfonyl betaines, and alkyl amphoteric acetates. In a preferred embodiment, the betaine is alkyl amamidopropyl betaine.

[0152] In the context of component (c), the term "alkyl" refers to a straight or branched hydrocarbon chain that is not unsaturated and has 8 to 18 carbon atoms.

[0153] Examples of alkylamidopropyl betaine are cocamidopropyl betaine, behenamidopropyl betaine, capryl / capramidopropyl betaine, lauramidopropyl betaine, myristamidopropyl betaine, palmamidopropyl betaine, palmamidopropyl betaine, and mixtures thereof.

[0154] Examples of commercially available useful betaine surfactants according to the invention are BETADET® HR, BETADET® HR-50 K, BETADET® S-20, BETADET® SHR and BETADET® THC-2, all of which are sold by KaoChemicals Europe.

[0155] In another embodiment of the invention, the amount of the amphoteric surfactant, i.e. component (c), in the composition is 0.5 wt.% to 20 wt.%, preferably 1.2 wt.% to 18 wt.%, and more preferably 2 wt.% to 10 wt.%, relative to the total amount of the cosmetic composition.

[0156] In a preferred embodiment, the weight ratio of the sum of components (a) and (b) to component (c) is 5:1 to 1:20, preferably 5:1 to 1:15:XX, and more preferably 5:1 to 1:10.

[0157] In one embodiment of the present invention, the cosmetic composition comprises:

[0158] -0.5 wt.% to 15 wt.%, preferably 1.2 wt.% to 10 wt.%, more preferably 2 wt.% to 10 wt.% of component (a)

[0159] -0.5 wt.% to 30 wt.%, preferably 1.2 wt.% to 20 wt.%, more preferably 2 wt.% to 20 wt.% of component (b)

[0160] -0.5 wt.% to 20 wt.%, preferably 1.2 wt.% to 18 wt.%, more preferably 2 wt.% to 10 wt.% of component (c)

[0161] The specified amounts are each expressed as a weight percentage of the mentioned component relative to the total weight of the cosmetic composition.

[0162] The pH of the cosmetic composition of the present invention is 3.5 to 7.5, preferably 4.0 to 7.0, and more preferably 4.5 to 6.5.

[0163] The cosmetic compositions according to the present invention may further include oil components, organosilicon compounds, powders, nonionic surfactants, anionic surfactants, polymers, metal ion chelators, UV protection factors, vitamins, antioxidants, antioxidant auxiliaries, fragrance oils, bacterial inhibitors, etc., as other excipients and additives.

[0164] Examples of oils include liquid oils, solid oils, waxes, hydrocarbon oils, and synthetic ester oils. Suitable oil components are, for example, Guerbert alcohols based on fatty alcohols containing 6 to 22, preferably 8 to 10, carbon atoms. Esters of straight-chain C6-C22 fatty acids and straight-chain C6-C22 fatty alcohols, and esters of branched C6-C22 carboxylic acids and straight-chain C6-C22 fatty alcohols, such as myristyl myristate, myristyl palmitate, myristyl stearate, myristyl isostearate, myristyl oleate, myristyl behenate, myristyl erucate, cetyl myristate, cetyl palmitate, cetyl stearate, cetyl isostearate, cetyl oleate, cetyl behenate, cetyl erucate, stearyl myristate, stearyl palmitate, stearyl stearate, stearyl isostearate, stearyl oleate, stearyl behenate, stearyl erucate. Alcohol esters, isostearyl myristate, isopropyl myristate, isostearyl palmitate, isostearyl stearate, isostearyl isostearyl oleate, isostearyl behenate, isostearyl oleate, oleyl palmitate, oleyl stearate, isostearyl isostearyl oleate, oleyl behenate, oleyl erucate, behenate myristate, behenate palmitate, behenate stearate, isostearyl isostearyl oleate, behenate oleate, behenate erucate, behenate myristate, behenate palmitate, behenate stearate, behenate stearate, behenate isostearyl oleate, behenate erucate, behenate myristate, behenate palmitate, behenate stearate, behenate isostearyl oleate, behenate erucate cleats), behenicol ester and erucicol ester.Also suitable are esters of straight-chain C6-C22 fatty acids with branched-chain alcohols (more particularly 2-ethylhexanol), esters of hydroxycarboxylic acids with straight-chain or branched-chain C6-C22 fatty alcohols, esters of straight-chain and / or branched-chain fatty acids with polyols (e.g., propylene glycol, dimer glycol, or trimer glycol) and / or Guerbert alcohols, triglycerides based on C6-C10 fatty acids, and liquid monoglycerides / diglycerides / triglyceride mixtures based on C6-C18 fatty acids. Esters of C6-C22 fatty alcohols and / or Guerbert alcohols with aromatic carboxylic acids (especially benzoic acid); esters of C6-C12 dicarboxylic acids with straight-chain or branched alcohols containing 1 to 22 carbon atoms or polyols containing 2 to 10 carbon atoms and 2 to 6 hydroxyl groups; vegetable oils (such as avocado oil, almond oil, hazelnut oil, babassu palm oil, borage oil, peanut oil, jojoba oil, canola oil, hemp oil, soybean oil, milk thistle oil). Thistle oil), safflower oil, chufa oil, coconut oil, rapeseed oil, black cumin oil, wheat germ oil, sunflower seed oil, flaxseed oil, macadamia nut oil, corn oil, walnut oil, olive oil), branched primary alcohols, substituted cyclohexanes, straight-chain and branched C6-C22 fatty alcohol carbonates, guerbert carbonates, esters of benzoic acid with straight-chain and / or branched C6-C22 alcohols, straight-chain or branched symmetrical or asymmetric dialkyl ethers containing 6 to 22 carbon atoms per alkyl group, ring-opening products of epoxidized fatty acid esters and polyols, silicone oils and / or aliphatic or cycloalkanes such as dialkylcyclohexane.

[0165] Examples of waxes include natural waxes such as candelilla wax, carnauba wax, Japanese wax, espartograss wax, cork wax, guaruma wax, rice oil wax, sugarcane wax, ouricury wax, lignite wax, beeswax, shellac wax, spermatheca ceti, lanolin (wool wax), uropygial fat, ceresine, ozocerite (geothermal wax), petrolatum, paraffin wax, and microcrystalline wax; chemically modified waxes (hard waxes) such as montan ester wax, saol wax, and hydrogenated jojoba wax; and synthetic waxes such as polyalkylene wax and polyethylene glycol wax.

[0166] Examples of hydrocarbon oils include liquid paraffin, squalane, pterostilbene, paraffin wax, ceresin, squalene, petrolatum, and microcrystalline wax.

[0167] Suitable organosilicon compounds are, for example, dimethylpolysiloxane, methylphenylpolysiloxane, cyclic organosilicones, and amino-, fatty acid-, alcohol-, polyether-, epoxy-, fluorine-, glycoside-, and / or alkyl-modified organosilicon compounds, which can be liquid and resinous at room temperature. Preferred organosilicon compounds are hydrophobic silicone oils, which are silicone oils soluble in paraffin oil at 25°C. The hydrophobic silicone oils used according to the invention include volatile and non-volatile silicone oils.

[0168] Specific examples include those with the formula {(CH3)2SiO} x Cyclic methylsiloxanes (where x is 3 to 6), or having the formula ((CH3)2SiO{(CH3)2SiO} y Short-chain linear methylsiloxanes of Si(CH3)3 (where y is 0 to 5).

[0169] Some suitable cyclic methylsiloxanes are hexamethylcyclotrisiloxane (D3), a solid with a boiling point of 134 °C and the formula {(Me2)SiO}3; and octamethylcyclotetrasiloxane (D4), with a boiling point of 176 °C and a viscosity of 2.3 mm. 2 / s and has the formula {(Me2)SiO}4; decamethylcyclopentanesiloxane (D5) (cyclomethyl silicone oil), with a boiling point of 210℃ and a viscosity of 3.87 mm. 2 / s, having the formula {(Me2)SiO}5; and dodecylmethylcyclohexylsiloxane (DE), with a boiling point of 245℃ and a viscosity of 6.62 mm. 2 / s, with the formula {(Me2)SiO}6.

[0170] Some suitable short-chain linear methylsiloxanes are hexamethyldisiloxane (MM), which has a boiling point of 100°C and a viscosity of 0. 2 / s to 65mm 2 / s and has the formula Me3SiOMe3; octamethyltrisiloxane (MDM), with a boiling point of 152℃ and a viscosity of 1.04 mm. 2 / s and has the formula Me3SiOMe2SiOSiMe3; decamethyltetrasiloxane (MD2M), boiling point 194℃, viscosity 1.53mm 2 / s and has the formula Me3SiO(MeSiO)2SiMe3; dodecylpentasiloxane (MD3M), with a boiling point of 229℃ and a viscosity of 2.06 mm. 2 / s and has the formula Me3SiO(Me2SiO)3SiMe3; tetradecyl hexasiloxane (MD4M), with a boiling point of 245℃ and a viscosity of 2.63 mm. 2 / s and has the formula Me3SiO(Me2SiO)4SiMe3; hexadecylmethylmethylheptasiloxane (MD5M), with a boiling point of 270℃ and a viscosity of 3.24 mm. 2 / s and has the formula Me3SiO(Me2SiO)5SiMe3.

[0171] In addition, it also includes long-chain siloxanes, such as phenyltrimethylsiloxane, bis(phenylpropyl)dimethylsiloxane, dimethylsiloxane and dimethiconol.

[0172] Examples of powders include inorganic powders such as talc, kaolin, mica, sericite, muscovite, phlogopite, synthetic mica, lepidolite, biotite, vermiculite, bentonite, lithium montmorillonite, synthetic clay (laponite), magnesium carbonate, calcium carbonate, aluminum silicate, barium silicate, calcium silicate, magnesium silicate, strontium silicate, tungstate, magnesium, silica, zeolite, barium sulfate, calcined calcium sulfate (calcined gypsum), calcium phosphate, fluorapatite, hydroxyapatite, ceramic powders, metal soaps (e.g., zinc myristate, calcium palmitate, and aluminum stearate), and boron nitride; organic powders such as polyamide resin powder (nylon powder), polyethylene powder, polymethyl methacrylate powder, polystyrene powder, styrene-acrylic acid copolymer resin powder, and benzoguanamine resin powder. Poly(tetrafluoroethylene) powder and cellulose powder; inorganic white pigments such as titanium dioxide and zinc oxide; inorganic red pigments such as iron oxide (red iron oxide) and iron titanate; inorganic brown pigments such as γ-iron oxide; inorganic yellow pigments such as yellow iron oxide and ochre; inorganic black pigments such as black iron oxide and low-order titanium dioxide; inorganic purple pigments such as mango purple and cobalt purple; inorganic green pigments such as chromium oxide, chromium hydroxide and cobalt titanate; inorganic blue pigments such as ultramarine and Prussian blue; pearl pigments such as titanium dioxide-coated mica, titanium dioxide-coated bismuth oxychloride, titanium dioxide-coated talc, colored titanium dioxide-coated mica, bismuth oxychloride and fish scales; metallic powder pigments such as aluminum powder and copper powder; organic pigments such as zirconium, barium or aluminum lake (e.g., organic pigments such as Red... No. 201, Red No. 202, Red No. 204, Red No. 205, Red No. 220, Red No. 226, Red No. 228, Red No. 405, Orange No. 203, Orange No. 204, Yellow No. 205, Yellow No. 401, and Blue No. 404, or Red No. 3, Red No. 104, Red No. 106, Red No. 227, Red No. 230, Red No. 401, Red No. 505, Orange No. 205, Yellow No. 4, Yellow No. 5, Yellow No. 202, Yellow No. 203, Green No. 3 and Blue No. 1); as well as natural colors such as chlorophyll and beta-carotene.

[0173] Examples of lipophilic nonionic surfactants include sorbitol fatty acid esters (e.g., sorbitol monooleate, sorbitol monoisostearate, sorbitol monolaurate, sorbitol monopalmitate, sorbitol monostearate, sorbitol sesquioleate, sorbitol trioleate, diglycerol sorbitol penta-2-ethylhexanoate, and diglycerol sorbitol tetra-2-ethylhexanoate); glycerol or polyglycerol fatty acid esters (e.g., glycerol monocotyledonate, glycerol monoerucic acid ester, glycerol monoerucic acid ester, glycerol sesquioleate, glycerol monostearate, glycerol-α,α'-oleate pyroglutamate, and glycerol monostearate malate); propylene glycol fatty acid esters (e.g., propylene glycol monostearate); hardened castor oil derivatives; and glycerol alkyl ethers.

[0174] Examples of hydrophilic nonionic surfactants include POE-sorbitol fatty acid esters (e.g., POE-sorbitol monooleate, POE-sorbitol monostearate, and POE-sorbitol tetraoleate); POE-sorbitol fatty acid esters (e.g., POE-sorbitol monolaurate, POE-sorbitol monooleate, POE-sorbitol pentaoleate, and POE-sorbitol monostearate); and POE-glycerol fatty acid esters (e.g., POE-monoleate, POE-glycerol monostearate, and POE-glycerol monoisostearate). Esters and POE-glycerol triisostearate; POE-fatty acid esters (e.g., POE-distearate, POE-mono-dioleate, and glycol distearate); POE-alkyl ethers (e.g., POE-lauryl ether, POE-oleyl ether, POE-stearyl ether, POE-behenyl ether, POE-2-octyldodecyl ether, and POE-cholesterol ether); Pluronic surfactants (e.g., poloxamer); POE / POP-alkyl ethers (e.g., POE / POP cetyl ether, POE / POP...) 2-Decyltetradecyl ether, POE / POP monobutyl ether, POE / POP hydrogenated lanolin and POE / POP glyceryl ether; tetra-POE / tetra-POP-ethylenediamine condensates (e.g., Tetronic); POE-caster oil or hardened castor oil derivatives (e.g., POE-caster oil, POE-hardened castor oil, POE-hardened castor oil monoisostearate, POE-hardened castor oil triisostearate, POE-hardened castor oil monopyroglutamate monoisostearate, and POE-hardened castor oil maleate); POE-beeswax lanolin derivatives (e.g., POE-sorbitol beeswax); alkanolamides (e.g., coconut oil fatty acid diethanolamide, lauric acid monoethanolamide, and fatty acid isopropanolamide); POE-propylene glycol fatty acid esters; POE-alkylamines; POE-fatty acid amides; sucrose fatty acid esters; alkylethoxydimethoxyamine oxides; and trioleenyl phosphate esters.

[0175] Examples of anionic surfactants are, for example, alkyl sulfates (e.g., C6-C22 alkyl sulfates, metal salts of said C6-C22 alkyl sulfates, and ammonium salts of said C6-C22 alkyl sulfates or salts of organic amines having alkyl or hydroxyalkyl substituents), alkyl ether sulfate surfactant types (e.g., C6-C22 alkyl ether sulfates containing 0.5 mol to 5 mol (preferably 0.8 mol to 3 mol) ethylene oxide per mol of C6-C22 alkyl ether sulfate, metal salts of said alkyl C6-C22 ether sulfates, and ammonium salts of organic amines having alkyl or hydroxyalkyl substituents, examples being sodium lauryl ether sulfate, potassium lauryl ether sulfate, ammonium lauryl ether sulfate, and mono-, di-, and triethylethanolamine lauryl ether sulfates containing 0.8 mol to 3 mol ethylene oxide per mol of alkyl ether sulfate, or mixtures thereof). Anionic surfactants of the sulfosuccinate type are also possible examples, including alkyl C6-C22 sulfosuccinates and alkyl C6-C22 ether sulfosuccinates, preferably monoalkyl and dialkyl C6-C22 sulfosuccinates, and monoalkyl and dialkyl C6-C22 ether sulfosuccinates containing 0.5 mol to 10 mol (preferably 1 mol to 5 mol) of ethylene oxide per mol of alkyl (e.g., monoalkyl or dialkyl) C6-C22 ether sulfosuccinates, or mixtures thereof. Metal salts of said monoalkyl and dialkyl C6-C22 sulfosuccinates and monoalkyl and dialkyl C6-C22 ether sulfosuccinates, as well as ammonium salts or salts of organic amines having alkyl or hydroxyalkyl substituents, can be used.

[0176] Suitable cationic polymers are, for example, cationic cellulose derivatives, such as those available from Amerchol under the name Polymer JR. The following are examples of products obtained from 400: quaternized hydroxyethyl cellulose, cationic starch, diallyl ammonium salts and acrylamide copolymers, quaternized vinylpyrrolidone / vinylimidazolium polymers such as Luviquat (BASF), condensation products of polyethylene glycol and amines, quaternized collagen peptides such as lauryl dimethylammonium hydroxypropyl hydrolyzed collagen, quaternized wheat peptides, polyethyleneimine, cationic organosilicon polymers such as ammonia-terminated polydimethylsiloxane (Amodimethicone), a copolymer of adipic acid and dimethylamino-hydroxypropyl diethylenetriamine (Cartaretine, Sandoz), copolymers of acrylic acid and dimethyl diallyl ammonium chloride, polyquaternary ammonium salt polymers, polyamino polyamides and their crosslinked water-soluble polymers, cationic chitin derivatives such as quaternized chitosan (optionally microcrystalline distribution), condensation products of dihaloalkyl (e.g., dibromobutane) and dialkylamine (e.g., dimethylamino-1,3-propane), and cationic guar gum (e.g., Celanese Jaguar). CBS, Jaguar C-17, Jaguar C-16, and quaternary ammonium salt polymers (e.g. Mirapol A-15, Mirapol AD-1, Mirapol AZ-1).

[0177] Suitable anionic, amphoteric, amphoteric, and nonionic polymers include, 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 and polyol-crosslinked polyacrylic acid, 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 optional derivatized cellulose ethers and siloxanes.

[0178] Examples of UV protective agents include organic substances (filters) that are liquid or crystalline at room temperature and are capable of absorbing ultraviolet radiation and releasing the absorbed energy (e.g., heat) in the form of longer-wavelength radiation. UV-B filters can be oil-soluble or water-soluble. Examples of oil-soluble substances include: 3-benzyl camphor or 3-benzyl camphor and its derivatives, such as 3-(4-methylbenzyl)-camphor; 4-aminobenzoic acid derivatives, preferably 4-(dimethylamino)-benzoic acid-2-ethylhexyl ester, 4-(dimethylamino)-benzoic acid-2-octyl ester, and 4-(dimethylamino)-benzoic acid-pentyl ester; esters of cinnamic acid, preferably 4-methoxycinnamic acid-2-ethylhexyl ester, 4-... -Propyl methoxycinnamate, isoamyl 4-methoxycinnamate, 2-cyano-3,3-phenylcinnamate-2-ethylhexyl ester (Octocrylene); esters of salicylic acid, preferably 2-ethylhexyl salicylate, 4-isopropylbenzyl salicylate, and methyl salicylate; derivatives of benzophenone, preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2-... '-Dihydroxy-4-methoxybenzophenone; esters of benzomalonic acid, preferably di-2-ethylhexyl 4-methoxyphenylmalonate; triazine derivatives, such as 2,4,6-triphenylamino-(p-carbonyl-2'-ethyl-1'-hexyloxy)-1,3,5-triazine and octyltriazinone; propane-1,3-dione, such as 1-(4-tert-butylphenyl)-3-(4T-methoxyphenyl)-propane-1,3-dione; 2 1-Phenylenylbenzimidazole-5-sulfonic acid and its alkali metal salts, alkaline earth metal salts, ammonium salts, alkyl ammonium salts, alkanol ammonium salts and glucosamine ammonium salts; sulfonic acid derivatives of benzophenone, preferably 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid and its salts; sulfonic acid derivatives of 3-benzyl camphor such as, for example, 4-(2-oxo-3-iminoborneolmethyl)-benzenesulfonic acid and 2-methyl-5-(2-oxo-3-iminoborneol)-sulfonic acid and their salts.

[0179] Typical UV-A filters are, in particular, derivatives of benzoylmethane, such as 1-(4'-tert-butylphenyl)-3-(4'-methoxyphenyl)-propane-1,3-dione, 4-tert-butyl-4'-methoxydibenzoylmethane (Parsol 1789), or 1-phenyl-3-(4'-isopropylphenyl)-propane-1,3-dione.

[0180] UV-A and UV-B filters can, of course, be used in mixtures. In addition to the soluble substances mentioned, insoluble pigments, i.e., finely dispersed metal oxides or salts, can also be used for this purpose. Examples of suitable metal oxides are particularly zinc oxide and titanium dioxide, as well as oxides of iron, zirconium, silicon, manganese, aluminum, and cerium, and mixtures thereof. Silicates (talc), barium sulfate, and zinc stearate can be used as salts. Oxides and salts are used in the form of pigments in skin care and skin-protecting lotions and decorative cosmetics. The average diameter of the particles should be less than 100 nm, preferably 5 nm to 50 nm, more preferably 15 nm to 30 nm. They can be spherical, although elliptical particles or other non-spherical particles can also be used. Pigments can also be surface-treated, i.e., hydrophilicated or hydrophobicated. Typical examples are coated titanium dioxide, such as Titandioxid T 805 (Degussa) or Eusolex T2000 (Merck). Suitable hydrophobic coating materials are especially silicones, particularly trialkoxyoctylsilane or dimethyl silicone oil. So-called micron or nano pigments are preferred for use in sunscreen products. Micronized zinc oxide is preferred.

[0181] In addition to the two main groups of protective factors mentioned above, secondary protective factors of the antioxidant type can also be used. Antioxidant-type secondary sunscreens interrupt the photochemical reaction chain triggered when UV rays penetrate the skin. Typical examples of suitable antioxidants are amino acids (e.g., glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (e.g., uric acid) and their derivatives, peptides such as D,L-carnosine, D-carnosine, L-carnosine and their derivatives (e.g., anserine), carotenoids, carotenes (e.g., α-carotene, β-carotene, lycopene) and their derivatives, chlorogenic acid and its derivatives, keto acids and their derivatives (e.g., dihydroketoacid), aurylthioglycol, propylthiouracil, and others. Thiols (such as thioredoxin, glutathione, cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, pentyl, butyl and lauryl, palmitoyl, oleylenyl, γ-linoleylenyl, cholesterol and glyceryl esters) and their salts, dilauryl thiodipropionate, distearate thiodipropionate, thiodipropionic acid and its derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) and sulfadiazine compounds (such as butionine sulfoximine, homocysteine ​​sulfadiazine, butionine sulfone). sulfone), penta-, hexa-, and hepta-thionine sulfadiazine (in very small compatible doses) (and (metal) chelating agents (e.g., α-hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin), α-hydroxy acids (e.g., citric acid, lactic acid, malic acid), humic acid, bile acids, bile extracts, bilirubin, biliverdin, EDTA, EGTA and their derivatives, unsaturated fatty acids and their derivatives (e.g., gamma-linolenic acid, linoleic acid, oleic acid), folic acid and its derivatives, ubiquinone and panthenol and their derivatives, vitamin C and its derivatives (e.g., ascorbate palmitate, Mg ascorbate phosphate, ascorbate acetate), tocopherol and its derivatives (e.g., vitamin E acetate), vitamin Vitamin A and its derivatives (vitamin A palmitate) and benzoic acid coniferate, rutinic acid and its derivatives (α-glycylrutin, ferulic acid, furfuryl glucosyl alcohol, carnosine, butyl hydroxyphenyl, butyl hydroxyanisole, nordihydroguaiac acid, nordihydroguaiac acid, trihydroxy-propylphenyl ketone, uric acid and its derivatives, mannose and its derivatives, superoxide dismutase, zinc and its derivatives (e.g., ZnO, ZnSO4), selenium and its derivatives (e.g., selenomethionine selenium), stilbene and its derivatives (e.g., stilbene oxide, trans-stilbene oxide), and derivatives of these active substances suitable for the purposes of this invention (salts, esters, ethers, sugars, nucleotides, nucleosides, peptides, and lipids).

[0182] Examples of metal ion chelating agents include 1-hydroxyethane-1,1-diphosphonic acid, 4Na salt of 1-hydroxyethane-1,1-diphosphonic acid, disodium edetate, trisodium edetate, tetrasodium edetate, sodium citrate, sodium polyphosphate, sodium metaphosphate, gluconic acid, phosphoric acid, citric acid, ascorbic acid, succinic acid, edetate, and trisodium hydroxyethylethylenediaminetriacetate.

[0183] Examples of vitamins include vitamins A, B1, B2, B6, C, and E and their derivatives; pantothenic acid and its derivatives; and biotin.

[0184] Examples of antioxidants include tocopherol, butylated hydroxytoluene, butylated hydroxyanisole, and gallate. Examples of antioxidant adjuvants include phosphoric acid, citric acid, ascorbic acid, maleic acid, malonic acid, succinic acid, lactic acid, fumaric acid, phosphatidylcholine, hexametaphosphate, phytic acid, and ethylenediaminetetraacetic acid.

[0185] Suitable fragrance oils are mixtures of natural and synthetic fragrances. Natural fragrances include extracts of the following: flowers (lily, lavender, rose, jasmine, orange blossom, ylang-ylang), stems and leaves (geranium, patchouli, orange leaf), fruits (fennel, coriander, cilantro, juniper), peels (bergamot, lemon, orange), roots (nutmeg, angelica, celery, cardamom, costus root, iris, calamus), trees (pine, sandalwood, guaiac, cedar, mahogany), herbs and grasses (tarragon, lemongrass, sage, thyme), conifers and branches (spruce, fir, pine, dwarf pine), resins and balsams (galbanum, elemi, benzoin, myrrh resin, frankincense, balsam). Animal ingredients, such as civets and beavers, can also be used. Typical synthetic fragrance compounds are products of the ester, ether, aldehyde, ketone, alcohol, and hydrocarbon types. Examples of ester-type fragrance compounds are benzyl acetate, phenoxyethyl isobutyrate, p-tert-butyl cyclohexylacetate, linalool acetate, dimethyl benzyl carbene acetate, phenethyl acetate, linalool benzoate, benzyl formate, glycine ethyl methyl phenyl ester, allyl allyl propionate, styrene propyl propionate, and benzyl salicylate. Ethers include, for example, benzyl ethyl ether, while aldehydes include, for example, straight-chain alkanes containing 8 to 18 carbon atoms, citral, citronellol, citronellol oxyacetaldehyde, styracil, hydroxycitronellol, filial, and bourgeonal. Examples of suitable ketones are ionone, α-isomethylionone, and methyl cedrol. Suitable alcohols are anethole, citronellol, eugenol, isoeugenol, geraniol, linalool, phenethyl alcohol, and terpineol. Hydrocarbons mainly include terpenes and balsams. However, mixtures of different fragrance compounds are preferred, as they together produce a pleasant aroma. Other suitable fragrance oils are essential oils with relatively low volatility, which are mostly used as aroma components. Examples include sage oil, chamomile oil, clove oil, bee pollen oil, peppermint oil, cinnamon leaf oil, limeflower oil, juniper berry oil, vetiver oil, frankincense oil, galbanum oil, labolanum oil, and lavender oil.The following substances are preferably used alone or in mixtures: bergamot oil, dihydrogeraniol, lily aldehyde, neolily aldehyde, citronellol, phenethyl alcohol, α-hexylcinnamaldehyde, geraniol, benzylacetone, senna aldehyde, linalool, Boisambrene Forte, ambroxan, indole, hedione, sandelice, lemon oil, orange peel oil, orange oil, allyl pentyl oxalate, cyclovertal, lavender oil, sage oil, β-damascone, geranium oil, bourbon whiskey, cyclohexyl salicylate, vertofix coeur, ambroxol (Iso-E-Super), fixeprazole NP, evernyl, γ-methyl ionone. gamma), phenylacetic acid, geraniol acetate, benzyl acetate, oxidized rose, romillat, irotyl, and floramat.

[0186] Typical examples of antimicrobial agents are preservatives that specifically target Gram-positive bacteria, such as 2,4,4'-trichloro-2'-hydroxydiphenyl ether, chlorhexidine (1,6-di-(4-chlorophenyl-biguanidinyl)-hexane), or TCC (3,4,4'-triclocarban). Many perfumes and essential oils also possess antimicrobial properties. Typical examples are the active substances eugenol, menthol, and thymol found in clove, peppermint, and thyme oils.

[0187] The cosmetic compositions of the present invention can be conventionally prepared, for example, by mixing the selected excipients with the compositions defined as in any aspect and embodiment provided in the specification.

[0188] This cosmetic composition can be used in a wide range of products for skin and / or hair, such as mousses, gels, masks, conditioning agents for face or hair, formulations for improving hair styling or promoting combing or uncombing, for providing curl or shine, rinse preparations, compositions for hair dyeing or coloring, hand and body lotions and oils, products for improving skin hydration, cleansing milks, makeup remover compositions, creams or lotions for sun protection and protection against UV radiation, care and / or treatment emulsions and creams, anti-acne preparations, topical analgesics, mascaras, products intended for application to the lips or other mucous membranes, sticks, deodorant and antiperspirant products, shaving lotions, bath oils, talcum powder, and other similar compositions.

[0189] In another embodiment, the compositions of the present invention are used for hair care and / or for skin care. In another embodiment, the compositions of the present invention can be used as compositions for cleansing skin and / or hair, hair dyeing compositions, and compositions for conditioning and moisturizing skin and / or hair.

[0190] Therefore, another aspect relates to the use of the cosmetic compositions of the present invention for the care of skin and / or hair, the use being selected from cleansing skin and / or hair, conditioning and moisturizing skin and / or hair, and dyeing hair, preferably cleansing skin and / or hair.

[0191] In a preferred embodiment, the cosmetic composition of the present invention is used for cleansing skin and / or hair.

[0192] Methods for cleaning skin and / or hair are also part of this invention, wherein the methods include the following steps: wetting or moistening the skin and / or hair, applying the cosmetic composition according to the invention to the skin and / or hair, and rinsing the skin and / or hair with water.

[0193] Methods for conditioning human hair and / or skin are also part of this invention, wherein the method comprises the steps of: applying a cosmetic composition according to the invention to moistened hair and / or moistened skin, and rinsing the cosmetic composition off the hair and / or skin with water, or alternatively leaving the cosmetic composition on the hair and / or skin.

[0194] Specifically, in the methods defined above, a sufficient amount of the composition of the present invention is applied. The term "sufficient amount" refers to the amount of cosmetic composition necessary to achieve the cleansing or conditioning of the skin and / or hair, and can be readily determined by a person skilled in the art. Examples of sufficient amounts are 0.2 g to 20 g, more preferably 0.5 g to 15 g.

[0195] The following examples are provided to give those skilled in the art a sufficiently clear and complete explanation of the invention, but should not be considered as limitations on the basic aspects of the subject matter of the invention as described in the foregoing sections of this specification.

[0196] Example:

[0197] The first part of the Examples section corresponds to the method of preparing the composition according to the present invention.

[0198] The second part of the examples presents the physicochemical properties of the prepared compositions.

[0199] Example 1

[0200] Preparation of Composition A (Comparative)

[0201] 643.6 g (0.73 mol) of C12 / 14 alkyl polyglycosides were placed in a stirred flask and heated to 60 °C. After reaching the temperature, 29.1 g (0.73 mol) of NaOH pellets were added, and the mixture was stirred for 1 hour. Then, 84.7 g (0.73 mol) of sodium monochloroacetate was added, and the mixture was stirred again at 65 °C for 3 hours. A viscous, pale yellow liquid was formed. The pH (10% aqueous solution) was 11.7.

[0202] Preparation of Composition B (according to the present invention)

[0203] 632.2 g (0.71 mol) of C12 / 14 alkyl polyglycoside was placed in a stirred tank and heated to 60 °C. Once the temperature was reached, 0.8 g (0.007 mol) of sodium monochloroacetate was added and stirred until completely dissolved. Subsequently, 83.1 g (0.71 mol) of sodium monochloroacetate (0.28 g / min) and 28.6 g (0.71 mol) of NaOH pellets (0.10 g / min) were added simultaneously over a 5-hour period. The reaction mixture was then stirred at 65 °C for 3 hours. A viscous, pale yellow liquid was formed. The pH (10% aqueous solution) was 11.7.

[0204] Example 2

[0205] The viscosity of the composition was determined 24 hours after preparation at 20°C and 33% dry content using a Brookfield LV viscometer. Viscosity was measured using a No. 3 rotor at 12 rpm.

[0206] Table 1 summarizes the viscosity results:

[0207] Table 1:

[0208]

[0209] It can be seen that although the two compositions contain the same percentage of dry matter, the viscosity of the composition of the present invention (which is obtained after adding a halocarboxylic acid in two separate steps) is significantly lower when compared with composition A obtained by adding acid in a single step.

Claims

1. A method for preparing a composition comprising at least one carboxyalkylated alkyl glycoside and / or alkenyl glycoside, wherein the method comprises the following steps: i) Provide at least one alkyl glycoside and / or alkenyl glycoside of formula (I) in the reactor (component (b)) R 1 -[G] p Formula (I) Wherein R1 represents an alkyl or alkenyl group having 4 to 24 carbon atoms, preferably 10 to 18 carbon atoms, more preferably 10 to 16 carbon atoms, and even more preferably 12 to 16 carbon atoms; G is a sugar unit having 5 or 6 carbon atoms, preferably glucose; and the number of p is 1 to 10. ii) Adding a halocarboxylic acid, its salt, or an ester; iii) Add an alkaline reagent; Step ii) includes ii') The initial feed is intended to be 0.3 wt.% to 50 wt.%, preferably 0.5 wt.% to 25 wt.%, more preferably 1 wt.% to 10 wt.%, of the total amount of the halocarboxylic acid, its salt, or ester added in step (ii), and stirred until dissolved; and ii) Feed the remaining halocarboxylic acids, their salts or esters.

2. The preparation method according to claim 1, wherein, Steps ii) and iii) are performed simultaneously.

3. The preparation method according to any one of claims 1 to 2, wherein, The halocarboxylic acid, its salt or ester, from step (ii) and the basic reagent from step (iii) are each fed into the reaction at a constant rate.

4. The preparation method according to any one of claims 1 to 3, wherein, The molar ratio between the halocarboxylic acid, its salt or ester and the alkyl glycoside and / or alkenyl glycoside is 0.8:1 to 3:1, preferably 0.9:1 to 2:1, and more preferably 0.9:1 to 1.25:

1.

5. The preparation method according to any one of claims 1 to 4, wherein, The halocarboxylic acid, its salt or ester, from step ii) and the alkaline reagent from step iii) are each added to the reactor at a constant rate over a period of 4 to 6 hours, preferably 4.5 to 5.5 hours.

6. The preparation method according to any one of claims 1 to 5, wherein, The halocarboxylic acid, its ester or salt has formula (II). A-(CH2) m -COOX, formula (II) Where A represents halogen, m is 1 to 5, and X is selected from hydrogen, alkali metals, ammonium and alkaline earth metals.

7. A composition comprising at least one carboxylated alkyl glycoside and / or alkenyl glycoside compound, said composition being obtainable by the method according to any one of claims 1 to 6.

8. A cosmetic composition comprising the composition according to claim 7 and one or more cosmetically acceptable excipients and / or carriers.

9. The use of the composition according to claim 7 or the cosmetic composition according to claim 8 for the care of skin and / or hair, particularly for the cleansing of skin and / or hair.

10. A method for cleaning skin and / or hair, comprising the following steps: Wet or wet the skin and / or hair, apply a sufficient amount of the composition according to claim 7, or alternatively the cosmetic composition according to claim 8, onto the skin and / or hair, and then rinse.

11. A method for conditioning skin and / or hair, comprising the following steps: The composition according to claim 7, or alternatively the cosmetic composition according to claim 8, is applied to moistened skin and / or hair, and then the cosmetic composition is rinsed off the hair and / or skin with water, or alternatively the cosmetic composition is left on the hair and / or skin.

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