WO2019115478A1

WO2019115478A1 - Composition for inhibiting micro-organisms

Info

Publication number: WO2019115478A1
Application number: PCT/EP2018/084240
Authority: WO
Inventors: Franz-Xaver Scherl; Dirk Leinweber; Jan GAUCZINSKI
Original assignee: Clariant International Ltd
Priority date: 2017-12-11
Filing date: 2018-12-10
Publication date: 2019-06-20

Abstract

The present invention relates to a composition for inhibiting micro-organisms, as well as related processes, formulations, concentrates and uses. The composition comprises at least 30 wt.-% compound X, wherein compound X is according to Formula (I) wherein R is an unsaturated hydrocarbon chain having 5 to 13 carbon atoms; and wherein R1 is -H or a C1-6 unsubstituted alkyl moiety, preferably R1 is methyl.

Description

COMPOSITION FOR INHIBITING MICRO-ORGANISMS

FIELD OF THE INVENTION

The present invention relates to a composition for inhibiting micro-organisms, as well as related processes, formulations, concentrates and uses.

BACKGROUND OF THE INVENTION

Preservation of household formulations, such as cosmetic formulations, extends their shelf life and therefore provides greater value for money for consumers. Furthermore, preservatives prevent consumers from distributing microbes around their home or on themselves and hence provide health benefits. Anti-microbial actives are well-described in the art and there are many available that provide excellent performance.

Klug et al. in US-2012/0100085A1 (2012, Clariant) discloses liquid compositions which contain a) from 5 to 95 % by weight of sorbitan monocaprylate and b) from 5 to 95 % by weight of one or more alcohols of the formula (1 ) disclosed therein. Klug et al. discusses in §4 the objective of keeping the total amount of

antimicrobially active alcohols in the cosmetic, dermatological or pharmaceutical formulation low and finding a dermatologically and toxicologically harmless substance that supports the antimicrobial action of the antimicrobially active alcohols in a synergistic manner. Klug et al. then goes on to state that it has been found that the sorbitan monocaprylate already known and used in cosmetics as a surfactant and emulsifying agent fulfills exactly these conditions.

However, there is a desire for providing an array of sophisticated preservation systems whereby excellent anti-microbial performance is provided and yet keeping the levels of preservation actives to a minimum. In line with the statements of Klug et al., many well-known preservation actives having excellent efficacy are not preferred e.g. due to reduced consumer acceptance, health worries or due to regulatory restrictions. The levels of such actives may also be (legally) restricted for the same reasons. Furthermore, there is a desire for all elements of preservation systems to meet sustainability goals and ensure that household formulations are as environmentally friendly as possible.

There is thus a need to provide even more sophisticated preservation systems, and elements thereof, that provide excellent anti-microbial effects and yet are highly accepted by consumers, do not raise health or regulatory concerns, and have excellent sustainability and environmentally friendly profiles.

SUMMARY OF THE INVENTION

In a first aspect, the present invention relates to a composition for inhibiting micro- organisms wherein the composition comprises at least 30 wt.-% compound X, wherein compound X is according to Formula (I):

wherein R is an unsaturated hydrocarbon chain having 5 to 15 carbon atoms; and wherein R¹ is -H or a C1 -6 unsubstituted alkyl moiety, preferably R¹ is methyl.

DETAILED DESCRIPTION OF THE INVENTION

Definitions and General

In this document, including in all embodiments of all aspects of the present invention, the following definitions apply unless specifically stated otherwise. All percentages are by weight (w/w) of the total composition. All ratios are weight ratios.“wt.-%” means percentage by weight. References to‘parts’ e.g. a mixture of 1 part X and 3 parts Y, is a ratio by weight.“QS” or“QSP” means sufficient quantity for 100 % or for 100 g. +/- indicates the standard deviation. All ranges are inclusive and combinable. The number of significant digits conveys neither a limitation on the indicated amounts nor on the accuracy of the measurements. All numerical amounts are understood to be modified by the word“about”. All measurements are understood to be made at 23 °C and at ambient conditions, where“ambient conditions” means at 1 atmosphere (atm) of pressure and at 50 % relative humidity.“Relative humidity” refers to the ratio (stated as a percent) of the moisture content of air compared to the saturated moisture level at the same temperature and pressure. Relative humidity can be measured with a hygrometer, in particular with a probe hygrometer from VWR^® International. Herein“min” means“minute” or“minutes”. Herein“mol” means mole. Herein“g” following a number means“gram” or“grams”.“Ex.” means“example”. All amounts as they pertain to listed ingredients are based on the active level (‘solids’) and do not include carriers or by-products that may be included in commercially available materials. Herein, "comprising" means that other steps and other ingredients can be in addition.“Comprising” encompasses the terms "consisting of and

"consisting essentially of. The compositions, formulations, methods, uses, kits, and processes of the present invention can comprise, consist of, and consist essentially of the elements and limitations of the invention described herein, as well as any of the additional or optional ingredients, components, steps, or limitations described herein. Embodiments and aspects described herein may comprise or be combinable with elements, features or components of other embodiments and/or aspects despite not being expressly exemplified in

combination, unless an incompatibility is stated.“In at least one embodiment” means that one or more embodiments, optionally all embodiments or a large subset of embodiments, of the present invention has/have the subsequently described feature. Where amount ranges are given, these are to be understood as being the total amount of said ingredient in the composition, or where more than one species fall within the scope of the ingredient definition, the total amount of all ingredients fitting that definition, in the composition. For example, if the

composition comprises from 1 % to 5 % fatty alcohol, then a composition comprising 2 % stearyl alcohol and 1 % cetyl alcohol and no other fatty alcohol, would fall within this scope.

“Molecular weight” or“M.Wt.” or“MW” and grammatical equivalents mean the number average molecular weight. “Viscosity” is measured at 25 °C using a HAAKE Rotation Viscometer VT 550 with cooling/heating vessel and sensor systems according to DIN 53019 at a shear rate of 12.9 s-¹.

“Water-soluble” refers to any material that is sufficiently soluble in water to form a clear solution to the naked eye at a concentration of 0.1 % by weight of the material in water at 25 °C. The term“water-insoluble” refers to any material that is not“water-soluble”.

“Dry” or“substantially dry” means comprising less than 5 %, less than 3 % or, less than 2 %, less than 1 %, or about 0 % of any compound or composition being in liquid form when measured at 25 °C at ambient conditions. Such compounds or compositions being in liquid form include water, oils, organic solvents and other wetting agents. "Anhydrous" means that the composition comprises less than 5 %, less than 3 % or, less than 2 %, less than 1 %, or about 0 % water by total weight of the composition.

“Substantially free from” or“substantially free of means less than 1 %, or less than 0.8 %, or less than 0.5 %, or less than 0.3 %, or about 0 %, by total weight of the composition or formulation.

“Derivatives” includes but is not limited to, amide, ether, ester, amino, carboxyl, acetyl, acid, salt and/or alcohol derivatives of a given compound. In at least one embodiment,“derivatives thereof means the amide, ether, ester, amino, carboxyl, acetyl, acid, salt and alcohol derivatives.

“Monomer” means a discrete, non-polymerised chemical moiety capable of undergoing polymerisation in the presence of an initiator or any suitable reaction that creates a macromolecule e.g. such as polycondensation, polyaddition, anionic or cationic polymerization.“Unit” means a monomer that has already been polymerised i.e. is part of a polymer. "Polymer" means a chemical formed from the polymerisation of two or more monomers. The term "polymer" shall include all materials made by the

polymerisation of monomers as well as natural polymers. Polymers made from only one type of monomer are called homopolymers. Herein, a polymer comprises at least two monomers. Polymers made from two or more different types of monomers are called copolymers. The distribution of the different monomers can be random, alternating or block-wise (i.e. block copolymer). The term“polymer” used herein includes any type of polymer including homopolymers and

copolymers.

“Kit” means a package comprising a plurality of components.“Kit” may be referred to as“kit-of-parts”. An example of a kit is, for example, a first composition and a separately packaged second composition and optionally application instructions.

Explanation Of and Benefits Provided By the Invention

The present invention relates to a composition for inhibiting micro-organisms wherein the composition comprises compound X. Compound X relates to a specific type of unsaturated fatty N-methyl glucamide(s). It is important to note that the terms“glucamide” and“glucamine” are used interchangeably in the art (and herein) - both the terms“N-methyl glucamide” and“N-methyl glucamide” as used herein refer to the compound X according to Formula (I) to the extent that the R group is as claimed herein.

As per the present development it has it has surprisingly been found that such specific unsaturated fatty N-methyl glucamides are capable of inhibiting the growth of microorganisms.

Connor et al. in W092/06070 (1992, P&G) discloses a HIGH CATALYST

PROCESS FOR GLUCAMIDE DETERGENTS. There is no clear and

unambiguously derivable disclosure in Connor of the present invention, neither from a chemical structure perspective nor purpose and effect perspective. Surfactants based on undecylenic acid are known in the art - see for example Ludwig in EP0028459A2 (1981 , ICI). Unsaturated carboxylic acids in general are known in the art for use in preparing surfactants - see for example LOWICKI US4376789A (Grillo-Werke AG, 1983). The employment of unsaturated fatty N-methyl glucamides and their use in preservation is however not mentioned in these references.

Piggott in US1985424 (1934, ICI) discloses“textile assistants” and“ALKYLENE- OXIDE DERIVATIVES OF POLYHYDROXYALKYL-ALKYLAMIDES”. There is no clear and unambiguously derivable disclosure in Piggott of the present invention, neither from a chemical structure perspective nor purpose and effect perspective.

In particular, there is no explicit disclosure in Piggott of the specific type of unsaturated fatty N-methyl glucamides herein claimed.

Klug et at. in US2015/0140048A1 (2015, Clariant) discloses the USE OF

N-METHYL-N-ACYLGLUCAMINES AS SOLUBILIZERS. Claim 1 mentions

N-methyl-N-C8-C14-acylglucamines.

The specific unsaturated fatty N-methyl glucamides claimed herein are relatively short alkenyl chain polyols and represent amphiphilic compounds. The

hydrophobic hydrocarbon chain and the hydrophilic head group drive compound X into the interphases of oil/water, water/air, or water/phospholipid layers. The surface tension is thereby reduced. This allows interaction with cell walls, e.g. of microorganisms, and plays an important synergistic role in the mechanism of action of traditional preservatives. Compound X can stabilise oil/water interphases, e.g. by emulsifiying or solubilizing hydrophobic ingredients in polar solvents or modifying the viscosity of surfactant-based systems/surfactant solutions.

Regulatory restrictions in the field of preservatives have led to a smaller toolbox for formulators to preserve their formulations effectively. Synthetic and petroleum- based ingredients are under public scrutiny for many reasons, e.g. sustainability, safety, impurities, non-environmentally-friendly processes, waste generation, slow biodegradability, bad reputation amongst consumers. Lower amounts of preservatives have to be supported/improved in their preservation efficacy in order to provide sufficient protection against contamination of the formulation with microorganisms. Preservative boosters are used to overcome the gap in efficacy due to a reduction in the level of classical preservative used and boost the efficacy of preservatives synergistically. Commonly used preservative boosters are poorly water-soluble or completely water-insoluble. This makes formulating them difficult, as most formulations contain a high amount of water. Solubilisers may have to be used, to keep the ingredient in the formulation. Via the present invention, the cost of solubilisers can be saved, reducing formulation complexity and reducing storage need for more ingredients.

Indeed, the present invention provides excellent performance and provide the formulator with an excellent choice when deciding on a means for preserving the formulation. The specific type of unsaturated fatty N-methyl glucamides herein described inhibit the growth of microorganisms thus extending options for formulators. Indeed, compound X is water-soluble and can be dissolved at 1 % in water to obtain a clear solution. Similarly, 10 % of water can be dissolved in 90 % of a composition of compound X to obtain a clear solution; it is stable at a pH range of pH 4 - 10 due to the amide bond, which offers superior stability versus commonly used esters; it can be synthesised in a cost effective reaction without the need for process aids (during amidation). Another advantage lies in the fact that the compound X is a viscous liquid and can therefore easily be employed in a wide-variety of different formulations. Furthermore, the specific type of unsaturated fatty N-methyl glucamides of the present invention are based in the renewable raw materials glucose and fatty acids, which offer a more sustainable solution that is also more sustainable than commonly used boosters such as ethylhexylglycerin (EHG) or octanediol. Moreover, glucose is more easily available than many other sugars and sugar-derived ingredients are highly understood and accepted by consumers. Furthermore, the specific type of unsaturated fatty N-methyl glucamides as described herein offer many other benefits. Due to their surfactant- like structure, they can act as a hydrotrope and also as a wetting agent. Also they can act as emulsifiers due to their high HLB non-ionic surfactant-like structure and as solubilisers for the same reason. The details of the invention and its aspects are provided hereinafter.

First Aspect

The first aspect relates to a composition for inhibiting micro-organisms wherein the composition comprises at least 30 wt.-% compound X, wherein compound X is according to Formula (I):

wherein R is an unsaturated hydrocarbon chain having 5 to 15 carbon atoms; and wherein R¹ is -FI or a C1 -6 unsubstituted alkyl moiety, preferably R¹ is methyl.

In at least one embodiment, R is an unsaturated hydrocarbon chain having 9 to 14 carbon atoms. In at least one embodiment, R is an unsaturated hydrocarbon chain having 11 to 14 carbon atoms. In at least one embodiment, R is an unsaturated hydrocarbon chain having 7 to 13, preferably 7 to 11 carbon atoms. In at least one embodiment, R is an unsaturated hydrocarbon chain having seven, nine or eleven carbon atoms, or a combination thereof; preferably R is a linear, unsaturated hydrocarbon chain having seven, nine or eleven carbon atoms, or a combination thereof.

In at least one embodiment, R is a monounsaturated or di-unsaturated

hydrocarbon chain, preferably being linear.

In at least one embodiment, R is a monounsaturated hydrocarbon chain having 5 to 15 carbon atoms. In at least one embodiment, R is a monounsaturated hydrocarbon chain having seven, nine or eleven carbon atoms, or a combination thereof; preferably nine carbon atoms. In at least one embodiment, R is a monounsaturated linear hydrocarbon chain having seven, nine or eleven carbon atoms, or a combination thereof; preferably nine carbon atoms.

In at least one embodiment, R is H2C=CH-(CH2)7-.

In at least one embodiment, R is a monounsaturated or di-unsaturated

hydrocarbon chain having 11 to 14 carbon atoms. Preferably R is a linear hydrocarbon chain. In at least one embodiment, R is a di-unsaturated hydrocarbon chain having twelve or fourteen carbon atoms, or a combination thereof. In at least one embodiment, R is a monounsaturated linear hydrocarbon chain having eleven carbon atoms or nine carbon atoms, or a combination thereof.

In at least one embodiment, R¹ is -H, or is C1 to C6 alkyl, more preferably C1 to C4 alkyl, much more preferably C1 or C2 (methyl or ethyl); most preferably R¹ is methyl.

Compound X relates to a type of unsaturated fatty N-methyl glucamide. Formula (I) encompasses multiple different species of such specific unsaturated fatty N-methyl glucamides. For example, R is a hydrocarbon chain that can be branched or unbranched. In at least one embodiment, composition comprises at least 30 wt.-% compound X, wherein compound X is a combination of compounds according to Formula (I) having different R groups. In at least one embodiment, compound X is a mixture of different compounds according to Formula (I) wherein R is a linear unsaturated hydrocarbon chain having 5 to 13 carbon atoms.

In at least one embodiment, compound X is selected from the group consisting of N-decenoyl-N-methyl-glucamine, N-dodecenoyl-N-methyl-glucamine,

N-tridecadienoyl-N-methyl-glucamine, N-pentadecadienoyl-N-methyl-glucamine, and combinations thereof; preferably compound X is N-decenoyl-N-methyl- glucamine.

In at least one embodiment, the composition comprises a total amount of compound X being at least 30 wt.-% by total weight of the composition. In at least one embodiment, the composition comprises at least 40 wt.%, preferably at least 50 %, more preferably at least 60 %, even more preferably 70 wt.-%, even more preferably at least 80 wt.-%, most preferably at least 90 wt.-% compound X.

In at least one embodiment, the composition comprises a sole compound X according to Formula (I) and wherein R is an unsaturated hydrocarbon chain having seven, nine or eleven carbon atoms. In other words, the composition may comprise only one type of compound X according to Formula (I), wherein R is an unsaturated hydrocarbon chain having seven, nine or eleven carbon atoms.

Flaving such a pure composition has the benefit that the chemical interactions with other ingredients can be more easily predicted. Furthermore, it is more desirable for consumers when an ingredient relates to one type of molecule rather than a more complex mixture.

It may be desirable for the composition to comprise a minimum amount of one particular species of compound X according to Formula (I), wherein R is an unsaturated hydrocarbon chain having nine carbon atoms. In at least one embodiment, the composition comprises at least 15 wt.-% compound X, wherein compound X is according to Formula (I):

wherein R is H2C=CH-(CH2)7-. In at least one embodiment, the composition comprises at least 30 wt.-%, preferably at least 40 wt.-%, preferably at least 50 wt.-%, more preferably at least 60 wt.-%, even more preferably 70 wt.-%, even more preferably at least 80 wt.-%, most preferably at least 90 wt.-% compound X according to Formula (I), wherein R is H2C=CH-(CH2)7-.

In at least one embodiment, the composition is an aqueous solution. In at least one embodiment, the composition comprises solvent. In at least one embodiment, the composition comprises a solvent, wherein the solvent comprises water and/or alcohol. Solvent is useful for providing the compounds used in present invention in liquid form. In at least one embodiment, the solvent is cosmetically acceptable. In at least one embodiment, the composition comprises at least 10 wt.-%, preferably at least 20 wt.-%, more preferably at least 30 wt.-%, even more preferably at least 50 wt.-% water. Water is useful for economic reasons but also because it is cosmetically acceptable. Optionally the composition comprises water-miscible or water-soluble solvents such as lower alkyl alcohols. In at least one embodiment, the composition comprises C1 -C5 alkyl monohydric alcohols, preferably C2-C3 alkyl alcohols. The alcohols which may be present are in particular lower monohydric or polyhydric alcohols having 1 to 4 carbon atoms customarily used for cosmetic purposes, such as preferably ethanol and

isopropanol.

Optionally, the composition comprises a water-soluble polyhydric alcohol. In at least one embodiment, the water-soluble polyhydric alcohols are polyhydric alcohols having two or more hydroxyl groups in the molecule. In at least one embodiment, the water-soluble polyhydric alcohol is selected from the group consisting of: dihydric alcohols such as ethylene glycol, propylene glycol, trimethylene glycol, 1 ,2-butylene glycol, 1 ,3-butylene glycol, 1 ,4-butylene glycol, tetramethylene glycol, 2,3-butylene glycol, pentamethylene glycol, 2-butene-1 ,4- diol, hexylene glycol, octylene glycol; trihydric alcohols such as glycerine, trimethylol propane, 1 ,2,6-hexanetriol and the like; tetrahydric alcohols such as penthaerythritol; pentahydric alcohols such as xylytol, etc.; hexahydric alcohols such as sorbitol, mannitol; polyhydric alcohol polymers such as diethylene glycol, dipropylene glycol, polyethylene glycol, polypropylene glycol, tetraethylene glycol, diglycerine, polyethylene glycol, triglycerine, tetraglycerine, polyglycerine; dihydric alcohol alkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol monophenyl ether, ethylene glycol monohexyl ether, ethylene glycol mono-2-methylhexyl ether, ethylene glycol isoamyl ether, ethylene glycol benzyl ether, ethylene glycol isopropyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibutyl ether; dihydric alcohol alkyl ethers such as diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol butyl ether, diethylene glycol methyl ethyl ether, triethylene glycol

monomethyl ether, triethylene glycol monoethyl ether, propylene glycol

monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, propylene glycol isopropyl ether, dipropylene glycol methyl ether,

dipropylene glycol ethyl ether, dipropylene glycol butyl ether; dihydric alcohol ether esters such as ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, ethylene glycol monophenyl ether acetate, ethylene glycol diadipate, ethylene glycol disuccinate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, propylene glycol monophenyl ether acetate; glycerine monoalkyl ethers such as xyl alcohol, selachyl alcohol, batyl alcohol; sugar alcohols such as sorbitol, maltitol,

maltotriose, mannitol, sucrose, erythritol, glucose, fructose, starch sugar, maltose, xylytose, starch sugar reduced alcohol, glysolid, tetrahydrofurfuryl alcohol, POE tetrahydrofurfuryl alcohol, POP butyl ether, POP POE butyl ether,

tripolyoxypropylene glycerine ether, POP glycerine ether, POP glycerine ether phosphoric acid, POP POE pentanerythritol ether, and mixtures thereof.

In a preferred embodiment, the composition comprises a solvent selected from the group consisting of water, glycols, ethanol, and combinations thereof.

In a preferred embodiment, the composition comprises an aqueous, alcoholic or aqueous-alcoholic solvent, and wherein the aqueous, alcoholic or aqueous- alcoholic solvent comprises water, ethanol, propanol, isopropanol, 1 ,2-propylene glycol, 1 ,3-propylene glycol, isobutanol, butanol, butyl glycol, butyl diglycol, glycerol, or a mixture thereof; preferably wherein the aqueous, alcoholic or aqueous-alcoholic solvent comprises water, ethanol, propanol, isopropanol, 1 ,2-propylene glycol, 1 ,3-propylene glycol, glycerol, or mixtures thereof; more preferably wherein the aqueous, alcoholic or aqueous-alcoholic solvent comprises water, isopropanol, 1 ,2-propylene glycol, 1 ,3-propylene glycol, or mixtures thereof; even more preferably wherein the aqueous, alcoholic or aqueous-alcoholic solvent consists of water or consists of a mixture of water and an alcohol wherein the alcohol is selected from the group consisting of isopropanol, 1 ,2-propylene glycol and 1 ,3-propylene glycol.

Natural solvents can also be used. In at least one embodiment, the composition comprises a solvent selected from the group consisting of plant oil, honey, plant- derived sugar compositions, and mixtures thereof.

In at least one embodiment, the composition is a pumpable liquid. In at least one embodiment, the composition is paste-like.

In at least one embodiment, the viscosity of the composition is from 1 mPa.s to 20,000 mPa.s.

In at least one embodiment, the composition is the composition, besides compound X, is substantially free of any anti-microbial active. Anti-microbial actives are discussed in more detail in the third aspect.

Example Embodiments of the First Aspect:

In a preferred embodiment, the first aspect relates to a composition for inhibiting micro-organisms wherein the composition comprises at least 60 wt.-% compound X, wherein compound X is according to Formula (I):

wherein R=CO derives from 9-decenoic acid, or from 9-dodecenoic acid, or from 9,12-tridecadienoic acid, or from 9,12-pentadecadienoic acid; and R¹ is -H or a C1-6 unsubstituted alkyl moiety, preferably R¹ is methyl;

and wherein the composition is an aqueous solution.

Second Aspect

A second aspect relates to a process for synthesising the composition according to the first aspect, the process comprising:

(a) Contacting N-methyl-D-glucamine with an unsaturated carboxylic acid

methylester to form a reaction blend at elevated temperatures in presence of an alkaline catalyst and an alcohol;

(b) Distilling off methanol at ambient pressure;

(c) Allowing the reaction blend to react for at least 1 hour while reducing

pressure;

(d) Optionally isolating a composition according to the first aspect.

Such processes are known in the art - see for example Connor et al

EP0550637B1 (P&G, 1992), and particularly claim 1 and examples I to V therein, which are incorporated herein by reference.

In at least one embodiment, the unsaturated carboxylic acid methylester is selected from the group consisting of a 9-decenoyl moiety, a 9-dodecenoyl moiety, a 9,12-tridecadienoyl moiety, or a 9,12-pentadecadienoyl moiety and mixtures thereof.

In at least one embodiment, R¹ is -H, or is C1 to C6 alkyl, more preferably C1 to C4 alkyl, much more preferably C1 or C2 (methyl or ethyl). Most preferably R¹ is methyl. N-methyl-D-glucamine is available from Sigma-Aldrich and the unsaturated carboxylic acid metylesters are available from Elevance (Elevance Renewable Sciences, Inc., 2501 Davey Road Woodridge, IL 60517 USA).

“Reaction blend” is to be understood as a mixture of starting materials and any solvents or other materials employed in or useful for the reaction.

In at least one embodiment, the molar ratio of N-methyl-glucamine to the unsaturated fatty acid methylester is in the range of 0.9 to 1.1 , more preferably 0.95 to 1.05.

In at least one embodiment, the reaction blend in step (a) comprises propylene glycol as a solvent in the range of 1 to 20 % by weight, more preferably 2 to 10 % by weight.

In at least one embodiment, the reaction blend in step (a) comprises sodium methoxide as a catalyst in the range of 0.1 % to 2 % by weight.

In at least one embodiment, the reaction blend in step (a) starts with molten N-methyl-glucamine at 135°C and unsaturated methylester at elevated

temperature.

In at least one embodiment, the reaction (b) occurs by keeping the reaction mixture at 110 °C, more preferably at 100 °C while the methanol is distilling off.

In at least one embodiment, step (b) distilling off methanol is continued for 15 min, more preferably for half an hour.

In at least one embodiment, step (c) occurs under vacuum. In at least one embodiment, the vacuum conditions are 50 mbar pressure, more preferably 30 mbar. In at least one embodiment, the step (c) occurs for at least half an hour, more preferably at least 1 hour.

In at least one embodiment, the step (c) occurs at 100 °C, more preferably at 90 to 100 °C.

In at least one embodiment, the step (c) occurs with stirring and under nitrogen gas.

In at least one embodiment, the final product is diluted with water to form a solution for increased handling properties.

In at least one embodiment, step (d) involves isolating a compound X, wherein compound X is selected from the group consisting of N-decenoyl-N-methyl- glucamine, N-dodecenoyl-N-methyl-glucamine, N-tridecadienoyl-N-methyl- glucamine, N-pentadecadienoyl-N-methyl-glucamine, and combinations thereof; preferably compound X is N-decenoyl-N-methyl-glucamine.

During the synthesis process, a number of by-products may be formed. Examples include, for example, esterified N-Alkenoyl-N-Alkyl-Glucamines and cyclic components. Esterified N-Alkenoyl-N-Alkyl-Glucamines are present in the range from 0.1 to 5%, whereas the content of cyclic components is below 0.5%

These by-product compounds may also have anti-microbial activity.

Other by-products that may be generated include N-methyl-glucamine; free fatty acid; linear fatty N-methyl-diglucamides (i.e. two glucose moieties as the polar head group).

Example Embodiments of the Second Aspect:

In at least one embodiment, the second aspect relates to a process for

synthesising the composition according to the first aspect comprising: (a) Providing a hot melt of N-methyl-glucamine (1 mol) at a temperature of at least 125 °C;

(b) Preparing a mixture out of 9-decenoic acid methylester (1 mol) and 10% propyleneglycol (with respect to reaction mixture) at at least 100°C.

(c) Adding the hot melt of N-methyl-glucamine to the 9-decenoic acid

methylester mixture to form a reaction blend;

(d) Adding at least 0.1 % by weight sodium methoxide (neat or as a solution in methanol) to the reaction blend

(e) Heating the reaction blend to evaporate methanol for half an hour,

preferably by heating the reaction blend to 110 °C, more preferably to 100 °C; to distill of methanol

(f) Apply vacuum of at least 50 mbar to evaporate traces of methanol while keeping temperature at at least 80 °C for at least 1 hour

(g) Optionally isolating a composition according to the first aspect.

In at least one embodiment, the process comprises:

(a) Providing an aqueous solution of N-methyl-glucamine;

(b) Creating a hot melt of N-methyl-glucamine (1 mol) at a temperature of at least 100 °C by evaporating off the water from the aqueous solution of

N-methyl-glucamine;

(c) Preparing a mixture out of 9-decenoic acid methylester (1 mol) and 10% propyleneglycol (with respect to reaction mixture) at at least 100°C.

(d) Adding the 9-decenoic acid methylester mixture to the hot melt of N-methyl- glucamine to form a reaction blend;

(e) Adding at least 0.1 % by weight sodium methoxide (neat or as a solution in methanol) to the reaction blend

(f) Heating the reaction blend to evaporate methanol for half an hour,

(g) Apply vacuum of at least 50 mbar to evaporate traces of methanol while keeping temperature at at least 80 °C for at least half an hour.

(h) Optionally isolating a composition according to the first aspect. In at least one embodiment, the process comprises:

(a) Providing an aqueous solution of N-methyl-glucamine;

(b) Creating a hot melt of N-methyl-glucamine (1 mol) at a temperature of at least 100 °C by evaporating off the water from the aqueous solution of N-methyl-glucamine;

(c) Preparing a mixture out of 9-dodecenoic acid methylester (1 mol) and 10% propyleneglycol (with respect to reaction mixture) at at least 100°C.

(d) Adding the 9-dodecenoic acid methylester mixture to the hot melt of

N-methyl-glucamine to form a reaction blend;

(f) Heating the reaction blend to evaporate methanol for half an hour,

preferably by heating the reaction blend to 110 °C, more preferably to

100 °C; to distill of methanol

(h) Optionally isolating a composition according to the first aspect.

Third Aspect

A third aspect relates to a preservative concentrate comprising:

compound X, wherein the compound X is according to Formula (I):

wherein R is an unsaturated hydrocarbon chain having 5 to 15 carbon atoms, and R¹ is -H or a C1-6 unsubstituted alkyl moiety; and

an anti-microbial active. In at least one embodiment, compound X is according to the first aspect.

In at least one embodiment, R is an unsaturated hydrocarbon chain having seven, nine or eleven carbon atoms, or a combination thereof; preferably R is a linear, unsaturated hydrocarbon chain having seven, nine or eleven carbon atoms, or a combination thereof. Preferably R is monounsaturated. In at least one

embodiment, R is H2C=CH-(CH2)7-.

In at least one embodiment, the concentrate comprises from 1 wt.-% to 99 wt.-%, or from 5 wt.-% to 90 wt.-%, or from 5 wt.-% to 95 wt.-%, or from 20 wt.-% to 80 wt.-%, or from 30 wt.-% to 80 wt.-% compound X.

In at least one embodiment, the concentrate comprises from 1 wt.-% to 99 wt.-%, or from or from 5 wt.-% to 95 wt.-%, 10 wt.-% to 95 wt.-%, or from 20 wt.-% to 80 wt.-%, or from 20 wt.-% to 70 wt.-% anti-microbial active.

In at least one embodiment, the weight ratio of the compound X to the anti- microbial active is from 1 :9 to 9:1.

In at least one embodiment, the antimicrobial active is a preservative, wherein the preservative is selected from the group consisting of aromatic alcohols, organic acids and salts thereof, hydroxypyridones, alkyl diols, halogenated compounds, isothiazolinones and combinations thereof.

In at least one embodiment, the anti-microbial active is selected from the group consisting of: aromatic alcohols, organic acids and salts thereof, compounds according to Formula (P), alkyl diols, halogenated compounds, isothiazolinones, preservation boosters and combinations thereof; wherein Formula (P) is as follows:

wherein

R^1’ is independently selected from H, an unsubstituted or halogen-substituted, branched or unbranched C₁-C₂₀-alkyl radical, an unsubstituted or halogen- substituted C₅-C₈-cycloalkyl radical, an unsubstituted or halogen-substituted C₆-C₁₀-aryl radical or an unsubstituted or halogen-substituted, branched or unbranched C₇-C₂₀-aralkyl radical;

R^2’ is either O or S,

R^3’ is H or a C₁-C₄-alkyl radical;

X⁺ is a cation.

Preferably R³’ is methyl.

In at least one embodiment, the aromatic alcohols are selected from the group consisting of benzyl alcohol, phenoxyethanol, veratryl alcohol, propylene phenoxyethanol, phenethyl alcohol, phenylpropanol, vanillin, 2-methyl-1 -phenyl-2- propanol and combinations thereof.

In at least one embodiment, the organic acids and salts thereof are selected from the group consisting of benzoic acid, sorbic acid, dehydroacetic acid, lactic acid, salicylic acid, p-anisic acid, undecylenic acid, glycolic acid, propionic acid, and combinations thereof.

^'

In at least one embodiment, the compound according to Formula (P) is selected from the group consisting of 2-hydroxypyridine-N-oxide, 2-pyridinthiol-1 -oxide and salts thereof, 1 -hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1 H)-pyridone and salts thereof (preferably the monoethanolamine salt), and combinations thereof. Formula (P) discloses and encompasses the tautomeric equivalents of these compounds since an equilibrium always exists. In at least one embodiment, the compound according to Formula (P) is Octopirox®.

In at least one embodiment, the alkyl diols are selected from the group consisting of 1 ,2-pentanediol, 1 ,2-hexanediol, 1 ,6-hexanediol, 1 ,2-octanediol, 1 ,2-decanediol, methylpropanediol, and combinations thereof.

In at least one embodiment, the halogenated compounds are selected from the group consisting of chlorhexidine and salts thereof, triclosan, chlorphenesin, trichlorcarban, chloroxylenol, iodoproprinyl butylcarbamate, Bonopol, climbazole, and combinations thereof.

In at least one embodiment, the isothiazolinones are selected from the group consisting of methylisothiazolinone, methylchloroisothiazolinone,

benzylisothiazolinone and combinations thereof.

In at least one embodiment, the preservation booster is selected from the group consisting of ethylhexylglycerol, sorbitan caprylate, isosorbide caprylate, glyceryl caprylate, glyceryl undecylenate, and combinations thereof.

In at least one embodiment, the preservation booster is ethylhexylglycerol. In at least one embodiment, the anti-microbial active is selected from preservation boosters and preservatives.

In at least one embodiment, the preservative is selected from the group consisting of aromatic alcohols, organic acids and salts thereof, hydroxypyridones, alkyl diols, halogenated compounds, isothiazolinones and combinations thereof.

In at least one embodiment, the preservative is selected from the group consisting of hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1 H)-pyridone, benzoic acid, phenetyl alcohol, benzyl alcohol, phenoxyethanol, salts thereof, and combinations thereof.

In at least one embodiment, the preservative concentrate comprises:

compound X, wherein the compound X is according to Formula (I):

at least one preservation booster; and

at least one preservative, wherein the preservative is preferably selected from the group consisting of aromatic alcohols, organic acids and salts thereof, hydroxypyridones, alkyl diols, halogenated compounds,

isothiazolinones and combinations thereof.

Preferably the preservation booster is selected from the group consisting of ethylhexylglycerol, sorbitan caprylate, isosorbide caprylate, glyceryl caprylate glyceryl undecylenate, and combinations thereof. Preferably, the preservative concentrate comprises:

compound X, wherein the compound X is according to Formula (I):

wherein R is an unsaturated hydrocarbon chain having 5 to 15 carbon atoms; preferably wherein R is H2C=CH-(CH2)7-; and R¹ is -H or a C1-6 unsubstituted alkyl moiety and

sorbitan monocaprylate; and

benzyl alcohol.

In at least one embodiment, the concentrate is substantially free of a preservation booster.

In at least one embodiment, the concentrate is an aqueous solution.

In at least one embodiment, the concentrate comprises solvent. In at least one embodiment, the concentrate comprises a solvent, wherein the solvent comprises water and/or alcohol. Solvent is useful for providing the compounds used in present invention in liquid form. In at least one embodiment, the solvent is cosmetically acceptable. In at least one embodiment, the concentrate comprises at least 10 wt.-%, preferably at least 20 wt.-%, more preferably at least 30 wt.-%, even more preferably at least 50 wt.-% water. Water is useful for economic reasons but also because it is cosmetically acceptable. Optionally the concentrate comprises water-miscible or water-soluble solvents such as lower alkyl alcohols. In at least one embodiment, the concentrate comprises C1 -C5 alkyl monohydric alcohols, preferably C2-C3 alkyl alcohols. The alcohols which may be present are in particular lower monohydric or polyhydric alcohols having 1 to 4 carbon atoms customarily used for cosmetic purposes, such as preferably ethanol and

isopropanol.

Optionally, the concentrate comprises a water-soluble polyhydric alcohol. In at least one embodiment, the water-soluble polyhydric alcohols are polyhydric alcohols having two or more hydroxyl groups in the molecule. In at least one embodiment, the water-soluble polyhydric alcohol is selected from the group consisting of: dihydric alcohols such as ethylene glycol, propylene glycol, trimethylene glycol, 1 ,2-butylene glycol, 1 ,3-butylene glycol, 1 ,4-butylene glycol, tetramethylene glycol, 2,3-butylene glycol, pentamethylene glycol, 2-butene-1 ,4- diol, hexylene glycol, octylene glycol; trihydric alcohols such as glycerine, trimethylol propane, 1 ,2,6-hexanetriol and the like; tetrahydric alcohols such as penthaerythritol; pentahydric alcohols such as xylytol, etc.; hexahydric alcohols such as sorbitol, mannitol; polyhydric alcohol polymers such as diethylene glycol, dipropylene glycol, polyethylene glycol, polypropylene glycol, tetraethylene glycol, diglycerine, polyethylene glycol, triglycerine, tetraglycerine, polyglycerine; dihydric alcohol alkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol monophenyl ether, ethylene glycol monohexyl ether, ethylene glycol mono-2-methylhexyl ether, ethylene glycol isoamyl ether, ethylene glycol benzyl ether, ethylene glycol isopropyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibutyl ether; dihydric alcohol alkyl ethers such as diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol butyl ether, diethylene glycol methyl ethyl ether, triethylene glycol

monomethyl ether, triethylene glycol monoethyl ether, propylene glycol

In a preferred embodiment, the concentrate comprises a solvent selected from the group consisting of water, glycols, ethanol, and combinations thereof.

In a preferred embodiment, the concentrate comprises an aqueous, alcoholic or aqueous-alcoholic solvent, and wherein the aqueous, alcoholic or aqueous- alcoholic solvent comprises water, ethanol, propanol, isopropanol, 1 ,2-propylene glycol, 1 ,3-propylene glycol, isobutanol, butanol, butyl glycol, butyl diglycol, glycerol, or a mixture thereof; preferably wherein the aqueous, alcoholic or aqueous-alcoholic solvent comprises water, ethanol, propanol, isopropanol, 1 ,2-propylene glycol, 1 ,3-propylene glycol, glycerol, or mixtures thereof; more preferably wherein the aqueous, alcoholic or aqueous-alcoholic solvent comprises water, isopropanol, 1 ,2-propylene glycol, 1 ,3-propylene glycol, or mixtures thereof; even more preferably wherein the aqueous, alcoholic or aqueous-alcoholic solvent consists of water or consists of a mixture of water and an alcohol wherein the alcohol is selected from the group consisting of isopropanol, 1 ,2-propylene glycol and 1 ,3-propylene glycol.

Natural solvents can also be used. In at least one embodiment, the concentrate comprises a solvent selected from the group consisting of plant oil, honey, plant- derived sugar compositions, and mixtures thereof. In at least one embodiment, the concentrate comprises additives common in cosmetology, pharmacy, and dermatology, which are hereinafter called auxiliaries. In at least one embodiment, the auxiliary is selected from the group consisting of oily substances, emulsifiers, coemulsifiers, cationic polymers, film formers, superfatting agents, stabilizers, active biogenic substances, glycerol,

preservatives, pearlizing agents, dyes and fragrances, solvents, opacifiers, functional acids, and also protein derivatives such as gelatin, collagen

hydrolysates, natural or synthetic-based polypeptides, egg yolk, lecithin, lanolin and lanolin derivatives, fatty alcohols, silicones, deodorants, substances with a keratolytic and keratoplastic action, enzymes, and/or carriers/solvents. Preferably the auxiliary is selected from the group consisting of oily substances, emulsifiers, coemulsifiers, cationic polymers, film formers, superfatting agents, stabilizers, active biogenic substances, glycerol, pearlizing agents, dyes, fragrances, opacifiers, functional acids, protein derivatives such as gelatin, collagen

hydrolysates, natural or synthetic-based polypeptides, egg yolk, lecithin, lanolin and lanolin derivatives, fatty alcohols, silicones, deodorants, substances with a keratolytic and keratoplastic action, enzymes, and combinations thereof.

In at least one embodiment, the concentrate comprises water soluble vitamins and their derivatives, water soluble amino acids and their salts and/or derivatives, viscosity modifiers, dyes, nonvolatile solvents or diluents (water soluble and insoluble), pearlescent aids, thickeners, foam boosters, additional surfactants or nonionic co-surfactants, pediculocides, pH adjusting agents, perfumes,

preservatives, chelants, proteins, skin active agents, sunscreens, UV absorbers, vitamins, niacinamide, caffeine, minoxidil, and combinations thereof. In at least one embodiment, the concentrate comprises from 0 wt.-% to 5 wt.-% vitamins and amino acids, by total weight of the concentrate. The concentrate may also comprise pigment materials such as inorganic, nitroso, monoazo, disazo, carotenoid, triphenyl methane, triaryl methane, xanthene, quinoline, oxazine, azine, anthraquinone, indigoid, thionindigoid, quinacridone, phthalocianine, botanical, natural colors, including: water soluble components such as those having C.l. Names. The concentrate may comprise from 0 wt.-%, preferably from 0.0001 wt.-% to 5 wt.-% pigment materials.

Example Embodiments of the Third Aspect:

In at least one embodiment, the third aspect relates to a preservative concentrate consisting of:

compound X, wherein the compound X is according to Formula (I):

wherein R is an unsaturated hydrocarbon chain having 5 to 15 carbon atoms; preferably R is H2C=CH-(CH2)7-; and R¹ is -H or a C1-6 unsubstituted alkyl moiety; and

an anti-microbial active;

optionally a solvent;

optionally an auxiliary, wherein the auxiliary is selected from the group consisting of oily substances, emulsifiers, coemulsifiers, cationic polymers, film formers, superfatting agents, stabilizers, active biogenic substances, glycerol, pearlizing agents, dyes, fragrances, opacifiers, functional acids, protein derivatives such as gelatin, collagen hydrolysates, natural or synthetic-based polypeptides, egg yolk, lecithin, lanolin and lanolin derivatives, fatty alcohols, silicones, deodorants, substances with a keratolytic and keratoplastic action, enzymes, and combinations thereof.

at least 15 wt.-% of a compound X, wherein the compound X is according to Formula (I)

at least 10 wt.-% of an anti-microbial active;

optionally at least 75 wt.-% solvent;

wherein R is an unsaturated hydrocarbon chain having 5 to 13 carbon atoms; preferably R is H2C=CH-(CH2)7-; and R¹ is -H or a C1-6 unsubstituted alkyl moiety, preferably methyl; and

a preservative, wherein the preservative is selected from the group consisting of hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1 H)-pyridone, benzoic acid, phenetyl alcohol, benzyl alcohol, phenoxyethanol, salts thereof, and combinations thereof;

optionally a solvent;

- at least 15 wt.-% of a compound X, wherein the compound X is according to

Formula (I)

at least 10 wt.-% a preservative, wherein the preservative is selected from the group consisting of hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1 H)- pyridone, benzoic acid, phenetyl alcohol, benzyl alcohol, phenoxyethanol, salts thereof, and combinations thereof;

optionally a solvent;

Fourth Aspect

A fourth aspect relates to the use of a compound X as a preservative booster or as an antimicrobial agent, wherein compound X is according to Formula (I):

wherein R is an unsaturated hydrocarbon chain having 5 to 15 carbon atoms; and R¹ is -H or a C1-6 unsubstituted alkyl moiety.

In at least one embodiment, the compound X is according to the first aspect.

Preferably compound X is according to Formula (I) wherein R is H2C=CH-(CH2)7-. Preferably R¹ is methyl.

In at least one embodiment, compound X is selected from the group consisting of N-decenoyl-N-methyl-glucamine, N-dodecenoyl-N-methyl-glucamine, N- tridecadienoyl-N-methyl-glucamine, N-pentadecadienoyl-N-methyl-glucamine, and combinations thereof; preferably compound X is N-decenoyl-N-methyl-glucamine.

At least one embodiment relates to the use of a compound X as an antifungal agent, wherein compound X is according to Formula (I):

wherein R is an unsaturated hydrocarbon chain having 5 to 15 carbon atoms; R¹ is -H or a C₁-6 unsubstituted alkyl moiety. In at least one embodiment, the compound X is according to the first aspect.

Preferably compound X is according to Formula (I) wherein R is H2C=CH-(CH2)7-; preferably R¹ is methyl.

An alternative embodiment of the fourth aspect relates to the use of a compound X as an emulsifier or solubiliser, wherein compound X is according to Formula (I):

Preferably compound X is according to Formula (I) wherein R is H2C=CH-(CH2)7- and preferably R¹ is methyl. In at least one embodiment, compound X is selected from the group consisting of N-decenoyl-N-methyl-glucamine, N-dodecenoyl-N-methyl-glucamine,

Fifth Aspect

A fifth aspect relates to a method of reducing the effects of micro-organisms, wherein the method comprises adding the composition according to the first aspect to an anti-microbial active to form a formulation. In at least one

embodiment, the formulation is according to the sixth aspect.

In at least one embodiment, the level of the composition added to the formulation is from from 0.001 wt.-% to 20 wt.-%, preferably 0.01 wt.-% to 10 wt.-%, more preferably 0.1 wt.-% to 5 wt.-%, by total weight of the formulation.

Sixth Aspect

A sixth aspect relates to a formulation comprising a compound X according to Formula (I)

wherein R is an unsaturated hydrocarbon chain having 5 to 15 carbon atoms; and R¹ is -H or a C1-6 unsubstituted alkyl moiety. In at least one embodiment, the compound X is according to the first aspect.

Preferably, compound X is according to Formula (I) wherein R is H2C=CH-(CH2)7-. In at least one embodiment, the formulation comprises from 0.001 wt.-% to 20 wt.-%, preferably 0.01 wt.-% to 10 wt.-%, more preferably 0.1 wt.-% to 5 wt.-% compound X, by total weight of the formulation.

In at least one embodiment, the formulation comprises the composition according to the first aspect and/or the concentrate according to the third aspect.

In at least one embodiment, the formulation is selected from the group consisting of cosmetic formulations and household cleansing formulations.

In at least one embodiment, the formulation is a formulation selected from the group consisting of shampoo, body wash, facial cleanser, cleansing masks, bubble bath, bath oil, cleansing milk, micellar water, make-up remover, cleansing wipes, perfume, soaps, shaving soaps, shaving foams and cleansing foams.

In at least one embodiment, the formulation is a cosmetic formulation for cleansing hair and/or skin.

In at least one embodiment, the formulation is an aqueous solution.

In at least one embodiment, the formulation comprises solvent. In at least one embodiment, the formulation comprises a solvent, wherein the solvent comprises water and/or alcohol. Solvent is useful for providing the compounds used in present invention in liquid form. In at least one embodiment, the solvent is cosmetically acceptable. In at least one embodiment, the formulation comprises at least 10 wt.-%, preferably at least 20 wt.-%, more preferably at least 30 wt.-%, even more preferably at least 50 wt.-% water. Water is useful for economic reasons but also because it is cosmetically acceptable. Optionally the formulation comprises water-miscible or water-soluble solvents such as lower alkyl alcohols. In at least one embodiment, the formulation comprises C1 -C5 alkyl monohydric alcohols, preferably C2-C3 alkyl alcohols. The alcohols which may be present are in particular lower monohydric or polyhydric alcohols having 1 to 4 carbon atoms customarily used for cosmetic purposes, such as preferably ethanol and

isopropanol.

Optionally, the formulation comprises a water-soluble polyhydric alcohol. In at least one embodiment, the water-soluble polyhydric alcohols are polyhydric alcohols having two or more hydroxyl groups in the molecule. In at least one embodiment, the water-soluble polyhydric alcohol is selected from the group consisting of: dihydric alcohols such as ethylene glycol, propylene glycol, trimethylene glycol, 1 ,2-butylene glycol, 1 ,3-butylene glycol, 1 ,4-butylene glycol, tetramethylene glycol, 2,3-butylene glycol, pentamethylene glycol, 2-butene-1 ,4- diol, hexylene glycol, octylene glycol; trihydric alcohols such as glycerine, trimethylol propane, 1 ,2,6-hexanetriol and the like; tetrahydric alcohols such as penthaerythritol; pentahydric alcohols such as xylytol, etc.; hexahydric alcohols such as sorbitol, mannitol; polyhydric alcohol polymers such as diethylene glycol, dipropylene glycol, polyethylene glycol, polypropylene glycol, tetraethylene glycol, diglycerine, polyethylene glycol, triglycerine, tetraglycerine, polyglycerine; dihydric alcohol alkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol monophenyl ether, ethylene glycol monohexyl ether, ethylene glycol mono-2-methylhexyl ether, ethylene glycol isoamyl ether, ethylene glycol benzyl ether, ethylene glycol isopropyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibutyl ether; dihydric alcohol alkyl ethers such as diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol butyl ether, diethylene glycol methyl ethyl ether, triethylene glycol

monomethyl ether, triethylene glycol monoethyl ether, propylene glycol

In a preferred embodiment, the formulation comprises a solvent selected from the group consisting of water, glycols, ethanol, and combinations thereof.

In a preferred embodiment, the formulation comprises an aqueous, alcoholic or aqueous-alcoholic solvent, and wherein the aqueous, alcoholic or aqueous- alcoholic solvent comprises water, ethanol, propanol, isopropanol, 1 ,2-propylene glycol, 1 ,3-propylene glycol, isobutanol, butanol, butyl glycol, butyl diglycol, glycerol, or a mixture thereof; preferably wherein the aqueous, alcoholic or aqueous-alcoholic solvent comprises water, ethanol, propanol, isopropanol, 1 ,2-propylene glycol, 1 ,3-propylene glycol, glycerol, or mixtures thereof; more preferably wherein the aqueous, alcoholic or aqueous-alcoholic solvent comprises water, isopropanol, 1 ,2-propylene glycol, 1 ,3-propylene glycol, or mixtures thereof; even more preferably wherein the aqueous, alcoholic or aqueous-alcoholic solvent consists of water or consists of a mixture of water and an alcohol wherein the alcohol is selected from the group consisting of isopropanol, 1 ,2-propylene glycol and 1 ,3-propylene glycol. Natural solvents can also be used. In at least one embodiment, the formulation comprises a solvent selected from the group consisting of plant oil, honey, plant- derived sugar compositions, and mixtures thereof.

In at least one embodiment, the formulation comprises additives common in cosmetology, pharmacy, and dermatology, which are hereinafter called auxiliaries. In at least one embodiment, the auxiliary is selected from the group consisting of oily substances, emulsifiers, coemulsifiers, cationic polymers, film formers, superfatting agents, stabilizers, active biogenic substances, glycerol,

hydrolysates, natural or synthetic-based polypeptides, egg yolk, lecithin, lanolin and lanolin derivatives, fatty alcohols, silicones, deodorants, substances with a keratolytic and keratoplastic action, enzymes, and/or carriers/solvents.

In at least one embodiment, the formulation comprises water soluble vitamins and their derivatives, water soluble amino acids and their salts and/or derivatives, viscosity modifiers, dyes, nonvolatile solvents or diluents (water soluble and insoluble), pearlescent aids, thickeners, foam boosters, additional surfactants or nonionic co-surfactants, pediculocides, pH adjusting agents, perfumes,

preservatives, chelants, proteins, skin active agents, sunscreens, UV absorbers, vitamins, niacinamide, caffeine, minoxidil, and combinations thereof. In at least one embodiment, the formulation comprises from 0 wt.-% to 5 wt.-% vitamins and amino acids, by total weight of the formulation. The formulation may also comprise pigment materials such as inorganic, nitroso, monoazo, disazo, carotenoid, triphenyl methane, triaryl methane, xanthene, quinoline, oxazine, azine, anthraquinone, indigoid, thionindigoid, quinacridone, phthalocianine, botanical, natural colors, including: water soluble components such as those having C.l. Names. The formulation may comprise from 0 wt.-%, preferably from 0.0001 wt.-% to 5 wt.-% pigment materials.

In at least one embodiment, the formulation comprises an oily substance, which is any fatty substance which is liquid at room temperature (25 °C). In at least one embodiment, the formulation comprises oily substance selected from the group consisting of silicone oils, volatile or nonvolatile, linear, branched or cyclic, optionally with organic modification; phenylsilicones; silicone resins and silicone gums; mineral oils such as paraffin oil or vaseline oil; oils of animal origin such as perhydrosqualene, lanolin; oils of plant origin such as liquid triglycerides, e.g., sunflower oil, corn oil, soybean oil, rice oil, jojoba oil, babusscu oil, pumpkin oil, grapeseed oil, sesame oil, walnut oil, apricot oil, macadamia oil, avocado oil, sweet al.mond oil, lady’s-smock oil, castor oil, triglycerides of caprylic/capric acids, olive oil, peanut oil, rapeseed oil, argan oil, abyssinian oil, and coconut oil;

synthetic oils such as purcellin oil, isoparaffins, linear and/or branched fatty alcohols and fatty acid esters, preferably guerbet al.cohols having 6 to 18, preferably 8 to 10, carbon atoms; esters of linear (C6-C13) fatty acids with linear (C6-C20) fatty alcohols; esters of branched (C6-C13) carboxylic acids with linear (C6-C20) fatty alcohols, esters of linear (C6-C18) fatty acids with branched alcohols, especially 2-ethylhexanol; esters of linear and/or branched fatty acids with polyhydric alcohols (such as dimerdiol or trimerdiol, for example) and/or guerbet al.cohols; triglycerides based on (C6-C10) fatty acids; esters such as dioctyl adipate, diisopropyl dimer dilinoleate; propylene glycols/dicaprylate or waxes such as beeswax, paraffin wax or microwaxes, alone or in combination with hydrophilic waxes, such as cetylstearyl alcohol, for example; fluorinated and perfluorinated oils; fluorinated silicone oils; mixtures of the aforementioned compounds.

In at least one embodiment, the formulation comprises a non-ionic coemulsifier. In at least one embodiment, the non-ionic coemulsifier is selected from adducts of from 0 to 30 mol of ethylene oxide and/or from 0 to 5 mol of propylene oxide with linear fatty alcohols having 8 to 22 carbon atoms, with fatty acids having 12 to 22 carbon atoms, with alkylphenols having 8 to 15 carbon atoms in the alkyl group, and with sorbitan or sorbitol esters; (C12-C18) fatty acid monoesters and diesters of adducts of from 0 to 30 mol of ethylene oxide with glycerol; glycerol monoesters and diesters and sorbitan monoesters and diesters of saturated and unsaturated fatty acids having 6 to 22 carbon atoms and, where appropriate, their ethylene oxide adducts; adducts of from 15 to 60 mol of ethylene oxide with castor oil and/or hydrogenated castor oil; polyol esters and especially polyglycerol esters, such as polyglyceryl polyricinoleate and polyglyceryl poly-12-hydroxystearate, for example. Likewise suitable are mixtures of compounds from one or more of these classes of substance. Examples of suitable ionogenic coemulsifiers include anionic emulsifiers, such as mono -, di- or tri-phosphoric esters, but also cationic emulsifiers such as mono-, di-, and tri-alkyl quats and their polymeric derivatives.

In at least one embodiment, the formulation comprises a cationic polymer. Suitable cationic polymers include those known under the INCI designation

“Polyquaternium", especially Polyquaternium-31 , Polyquaternium-16,

Polyquaternium-24, Polyquaternium-7, Polyquaternium-22, Polyquaternium-39, Polyquaternium-28, Polyquaternium-2, Polyquaternium-10, Polyquaternium-11 , and also Polyquaternium 37 & mineral oil & PPG trideceth (Salcare SC95), PVP-dimethylaminoethyl methacrylate copolymer, guar- hydroxypropyltriammonium chlorides, and also calcium alginate and ammonium alginate. It is additionally possible to employ cationic cellulose derivatives; cationic starch; copolymers of diallylammonium salts and acrylamides; quaternized vinylpyrrolidone/vinylimidazole polymers; condensation products of polyglycols and amines; quaternized collagen polypeptides; quaternized wheat polypeptides; polyethyleneimines; cationic silicone polymers, such as amidomethicones, for example; copolymers of adipic acid and

dimethylaminohydroxypropyldiethylenetriamine; polyaminopolyamide and cationic chitin derivatives, such as chitosan, for example.

In at least one embodiment, the formulation comprises a superfatting agent. As superfatting agents it is possible to use substances such as, for example, polyethoxylated lanolin derivatives, lecithin derivatives, polyol fatty acid esters, monoglycerides, and fatty acid alkanol amides, the latter serving simultaneously as foam stabilizers. Moisturizers available include for example isopropyl palmitate, glycerol and/or sorbitol.

In at least one embodiment, the formulation comprises a stabiliser. As stabiliser it is possible to use metal salts of fatty acids, such as magnesium, aluminum and/or zinc stearate, for example. In at least one embodiment, the formulation comprises a care additive. The formulations can be blended with conventional ceramides, pseudoceramides, fatty acid N-alkylpolyhydroxyalkyl amides, cholesterol, cholesterol fatty acid esters, fatty acids, triglycerides, cerebrosides, phospholipids, panthenol and similar substances as a care additive.

In at least one embodiment, the formulation comprises an anti-fungal substance.

In at least one embodiment, the anti-fungal substance is selected from the group consisting of ketoconazole, oxiconazole, bifonazole, butoconazole, cloconazole, clotrimazole, econazole, enilconazole, fenticonazole, isoconazole, miconazole, sulconazole, tioconazole, fluconazole, itraconazole, terconazole, naftifine and terbinafine, zinc pyrithione, octopirox, and combinations thereof. In at least one embodiment, the formulation comprises a total amount of anti-fungal substance in the formulation of from 0.1 wt.-% to 1 wt.-%. In at least one embodiment, the formulation comprises a pyridinethione anti-dandruff particulates, for example 1-hydroxy-2-pyridinethione salts, are highly preferred particulate anti-dandruff agents. The concentration of pyridinethione antidandruff particulate may ranges from 0.1 wt.-% to 4 wt.-%, by total weight of the formulation, preferably from 0.1 wt.-% to 3 wt.-%, more preferably from 0.3 wt.-% to 2 wt.-%. Preferred pyridinethione salts include those formed from heavy metals such as zinc, tin, cadmium, magnesium, aluminum and zirconium, preferably zinc, more preferably the zinc salt of 1 -hydroxy-2-pyridinethione (known as "zinc pyridinethione" or "ZPT"), more preferably 1 -hydroxy-2-pyridinethione salts in platelet particle form. Salts formed from other cations, such as sodium, may also be suitable.

Pyridinethione anti-dandruff agents are described, for example, in US-2,809,971 ; US-3,236,733; US-3,753,196; US-3,761 ,418; US-4,345,080; US-4,323,683;

US-4,379,753; and US-4,470,982. It is contemplated that when ZPT is used as the anti-dandruff particulate in the formulations herein, that the growth or regrowth of hair may be stimulated or regulated, or both, or that hair loss may be reduced or inhibited, or that hair may appear thicker or fuller. Functional acids are acidic substances used to impart a clinical functionality to the skin or hair upon application. Suitable functional acids include alpha hydroxy acids, beta-hydroxy acids, lactic acid, retinoic acid, and similar substances.

In at least one embodiment, the formulation comprises an astringent. In at least one embodiment, the astringent is selected from the group consisting of

magnesium oxide, aluminium oxide, titanium dioxide, zirconium dioxide, zinc oxide, oxide hydrates, aluminium oxide hydrate (boehmite) and hydroxide, chlorohyd rates of calcium, magnesium, aluminium, titanium, zirconium or zinc. In at least one embodiment, the formulation comprises from 0.001 wt.-% to 10 wt.-%, or from 0.01 wt.-% to 9 wt.-%, or from 0.05 wt.-% to 8 wt.-%, or from 0.1 wt.-% to 5 wt.-% astringent.

In at least one embodiment, the formulation comprises a deodorising agent. In at least one embodiment, the deodorising agent is selected from the group consisting of allantoin, bisabolol, and combinations thereof. In at least one embodiment, the formulation comprises from 0.001 wt.-% to 10 wt.-%, or from 0.01 wt.-% to

9 wt.-%, or from 0.05 wt.-% to 8 wt.-%, or from 0.1 wt.-% to 5 wt.-% deodorising agent.

In at least one embodiment, the formulation comprises a sun protection agent and/or UV filter. Suitable sun protection agents and UV filters are disclosed in WO2013/017262A1 (published on 7^th Feb 2013), from page 32, line 11 to the end of page 33. In at least one embodiment, the sun protection agent and/or UV filter is selected from the group consisting of 4-amino benzoic acid,

3-(4'-trimethylammonium)-benzylide-boran-2-one-methylsulfate, camphor benzalkonium methosulfate, 3,3,5-trimethyl-cyclohexylsalicylate, 2-hydroxy-4- methoxybenzophenone, 2-phenylbenzimidazole-5-sulfonic acid and potassium-, sodium- und triethanolamine salts thereof, 3,3^'-(1 ,4-phenylene dimethine)-bis-(7,7- dimethyl-2-oxobicyclo[2.2.1]-heptane-1 -methane sulfonic acid) and its salts,

1 -(4-tert.-butylphenyl)-3-(4-methoxyphenyl)propan-1 ,3-dion, 3-(4^'-sulfo)- benzylidene-bornane-2-one its salts, 2-cyan-3, 3-diphenyl-acrylic acid-(2- ethylhexylester), polymers of N-[2(and 4)-(2-oxoborn-3-ylidenmethyl)benzyl]- acrylamide, 4-methoxy-cinnamic acid-2-ethyl-hexylester, ethoxylated ethyl-4- amino-benzoate, 4-methoxy-cinnamic acid-isoamylester, 2,4,6-tris-[p-(2- ethylhexyloxycarbonyl)anilino]-1 ,3,5-triazine, 2-(2H-benzotriazole-2-yl)-4-methyl-6- (2-methyl-3-(1 ,3,3,3-tetramethyl-1 -(trimethylsilyloxy)-disiloxanyl)-propyl)phenol, 4,4'-[(6-[4-((1 ,1 -dimethylethyl)-amino-carbonyl)phenylamino]-1 ,3,5-triazin-2,4- yl)diimino]bis-(benzoic acid-2-ethylhexylester), 3-benzophenone, 4-benzophenone (acic), 3(4'-methylbenzyliden)-D,L-camphor, 3-benzylidene-camphor, salicylic acid- 2-ethylhexylester, 4- dimethyl aminobenzic acid-2-ethylhexylester, hydroxy-4- methoxy-benzophenone-5 sulfonic acid and the sodium salt thereof, 4-isopropyl benzylsalicylate, N,N,N-trimethyl-4-(2-oxoborn-3-ylidenemethyl) anilium methyl sulfate, homosalate (INN), oxybenzone (INN), 2-phenylbenzimidazole-5-sulfonic acid and its sodium, potassium, and triethanolamine salts, octylmethoxy cinnamic acid, isopentyl-4-methoxy cinnamic acid, isoamyl-p-methoxy cinnamic acid, 2,4,6- trianilino-(p-carbo-2’-ethylhexyl-1’-oxy)-1 ,3,5-triazine (octyl triazone) phenol, 2,2(2H-benzotriazol-2-yl)-4-methyl-6-(2-methyl-3-(1 ,3,3,3-tetramethyl-1 - (trimethylsilyl)oxy)-disiloxanyl)propyl (drometrizole trisiloxane) benzic acid, 4,4-((6- (((1 ,1 -dimethylethyl)amino)carbonyl)phenyl)amino)-1 ,3,5-triazine-2,4- diyl)diimino)bis,bis(2-ethylhexyl)ester) benzoic acid, 4,4-((6-(((1 ,1 - dimethylethyl)amino)-carbonyl)phenyl)amino)-1 ,3,5-triazine-2,4- diyl)diimino)bis,bis(2-ethylhexyl)ester), 3-(4’-methylbenzylidene)-D,L-camphor (4-methylbenzylidene camphor), benzylidene-camphor-sulfonic acid, octocrylene, polyacrylamidomethyl-benzylidene-camphor, 2-ethylhexyl salicylate (octyl salicylate), 4-dimethyl-aminobenzoeacidethyl-2-hexylester (octyl dimethyl PABA), PEG-25 PABA, 2 hydroxy-4-methoxybenzo-phenone-5-sulfonic acid

(5-benzophenone) and the sodium salt thereof, 2,2’-methylene-bis-6-(2H- benzotriazol-2-yl)-4-(tetramethyl-butyl)-1 ,1 ,3,3-phenol, the sodium salt of 2-2’-bis- (1 ,4-phenylene)1 H-benzimidazole-4,6-disulfonic acid, (1 ,3,5)-triazine-2,4-bis((4-(2- ethyl-hexyloxy)-2-hydroxy)-phenyl)-6-(4-methoxyphenyl), 2-ethylhexyl-2-cyano- 3,3-diphenyl-2-propenoate, glyceryl octanoate, di-p-methoxy cinnamic acid, p-amino-benzoic acid and its ester, 4-tert-butyl-4'-methoxydibenzoylmethane, 4-(2- P-glucopyranoxy)propoxy-2-hydroxybenzophenone, octyl salicylate, methyl-2, 5- diisopropyl cinnamic acid, cinoxate, dihydroxy-dimethoxybenzophenone, disodium salts of 2,2’-dihydroxy-4,4'-dimethoxy-5,5'-disulfobenzophenone, dihydroxybenzophenone, 1 ,3,4-dimethoxyphenyl-4,4-dimethyl-1 ,3-pentanedione, 2-ethylhexyl-dimethoxybenzyliden-dioxoimidazolidinpropionate, methylene-bis- benztriazolyl tetramethylbutylphenol, phenyldibenzimidazoltetrasulfonate, bis- ethylhexyloxyphenol-methoxyphenol-triazine, tetrahydroxybenzophenone, terephthalylidendicamphor-sulfonic acid, 2,4,6-tris[4,2- ethylhexyloxycarbonyl)anilino]-1 ,3,5-triazine, methyl-bis(trimethylsiloxy)silyl- isopentyl trimethoxy cinnamic acid, amyl-p-dimethylaminobenzoate, amyl-p- dimethylamino benzoate, 2-ethylhexyl-p-dimethylaminobenzoate, isopropyl-p- methoxy cinnamic acid/diisopropyl cinnamic acid ester, 2-ethylhexyl-p-methoxy cinnamic acid, 2-hydroxy-4-methoxy benzophenone, 2-hydroxy-4- methoxybenzophenone-5-sulfonic acid and the trihydrate, 2-hydroxy-4- methoxybenzophenone-5-sulfonate sodium salt, phenyl-benzimidazole sulfonic acid, and combinations thereof. In at least one embodiment, the formulation comprises from 0.001 wt.-% to 10 wt.-%, preferably from 0.05 wt.-% to 5 wt.-%, even more preferably from 0.1 wt.-% to 3 wt.-%, most preferably from 0.05 wt.-% to 1 wt.-% sun protection agent and/or UV filter. In at least one embodiment, the formulation comprises a photoprotective substance in an amount of from 0.01 to 10 wt.-%, or from 0.1 to 5 wt.-%, more preferably from 0.2 to 2 wt.-%. Suitable photoprotective substances include, in particular, all of the photoprotective substances specified in EP1084696A1 (L’OREAL), which is incorporated herein by reference. In a preferred embodiment, the photoprotective substance is selected from the group consisting of 2-ethyl hexyl 4-methoxycinnamate, methyl

methoxycinnamate, 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid, polyethoxylated p-aminobenzoates, and combinations thereof.

In at least one embodiment, the formulation comprises an anti-oxidant. In at least one embodiment, the anti-oxidant is selected from the group consisting of amino acids, peptides, sugars, imidazoles, carotinoids, carotenes, chlorogenic acid, lipoic acid, thiols, thiol glycosyl esters, thiol N-acetyl esters, thiol methyl esters, thiol ethyl esters, thiol propyl esters, thiol amyl esters, thiol butyl esters, thiol lauryl esters, thiol palmitoyl esters, thiol oleyl esters, thiol linoleyl esters, thiol cholesteryl esters, thiol glyceryl esters, dilaurylthiodipropionate, distearylthiodipropionate, thiodipropionic acid, metal chelators, hydroxy acids, fatty acids, folic acids, vitamin C, tocopherol, vitamin A, stilbenes, derivatives and combinations thereof. In at least one embodiment, the anti-oxidant is selected from the group consisting of glycine, histidine, tyrosine, tryptophan, urocaninic acid, D,L-carnosine,

D-carnosine, L-carnosine, beta-carotene, alpha-carotene, lycopene, dihydrolipoic acid, aurothioglucose, propylthiouracil, thioredoxine, glutathione, cysteine, cystine, cystamine, buthioninsulfoximine, homocysteinsulfoximine, buthioninsulfone, penta- , hexa-, heptathioninsulfoximine, hydroxyfatty acids, palmitic acid, phytinic acid, lactoferrin, citric acid, lactic acid, malic acid, humic acid, bile acid, bilirubin, biliverdin, EDTA, EGTA, linoleic acid, linolenic acid, oleic acid, butylhydroxyanisol, trihydroxybutyrophenone, ubichinon, ubichinol, ascorbylpalmitate,

Mg-ascorbylphosphate, ascorbylacetate, vitamin E acetate, vitamin A palmitate, carnosine, mannose, ZnO, ZnS04, selenium methionine, stilbenes, superoxide dismutase, and combinations thereof. In at least one embodiment, the antioxidant is selected from the group consisting of vitamin A, vitamin A derivatives, vitamin E, vitamin E derivatives, and combinations thereof. In at least one embodiment, the formulation comprises from 0.001 wt.-% to 10 wt.-%, preferably from 0.05 wt.-% to 5 wt.-%, even more preferably from 0.1 wt.-% to 3 wt.-%, most preferably from 0.05 wt.-% to 1 wt.-% antioxidant.

In at least one embodiment, the formulation comprises a dye or pigment. In at least one embodiment, the formulation comprises at least one pigment. Suitable dyes and pigments are disclosed in WO2013/017262A1 in the table spanning pages 36 to 43. These may be colored pigments which impart color effects to the product mass or to hair, or they may be luster effect pigments which impart luster effects to the product mass or to the hair. The color or luster effects on the hair are preferably temporary, i.e. they last until the next hair wash and can be removed again by washing the hair with customary shampoos. In at least one embodiment, the formulation comprises a total amount of from 0.01 wt.-% to 25 wt.-%, preferably from 5 wt.-% to 15 wt.-% pigment. In at least one embodiment, the particle size of the pigment is from 1 micron to 200 micron, preferably from

3 micron to 150 micron, more preferably 10 micron to 100 micron. The pigments are colorants which are virtually insoluble in the application medium, and may be inorganic or organic. Inorganic-organic mixed pigments are also possible. Preference is given to inorganic pigments. The advantage of inorganic pigments is their excellent resistance to light, weather and temperature. The inorganic pigments may be of natural origin. In at least one embodiment, the inorganic pigment is selected from the group consisting of chalk, ochre, umber, green earth, burnt sienna, graphite, and combinations thereof. The pigments may be white pigments, such as, for example, titanium dioxide or zinc oxide, black pigments, such as, for example, iron oxide black, colored pigments, such as, for example, ultramarine or iron oxide red, lustre pigments, metal effect pigments, pearlescent pigments, and fluorescent or phosphorescent pigments, where preferably at least one pigment is a colored, nonwhite pigment. In at least one embodiment, the pigment is selected from the group consisting of metal oxides, hydroxides and oxide hydrates, mixed phase pigments, sulfur-containing silicates, metal sulfides, complex metal cyanides, metal sulfates, chromates and molybdates, and the metals themselves (bronze pigments), and combinations thereof. In at least one embodiment, the pigment is selected from the group consisting of titanium dioxide (Cl 77891 ), black iron oxide (Cl 77499), yellow iron oxide (Cl 77492), red and brown iron oxide (Cl 77491 ), manganese violet (Cl 77742), ultramarine (sodium aluminum sulfosilicates, Cl 77007, Pigment Blue 29), chromium oxide hydrate (Cl 77289), Prussian blue (ferric ferrocyanide, Cl 77510), carmine (cochineal), and combinations thereof. In at least one embodiment, the pigment is selected from the group consisting of pearlescent and colored pigments based on mica which are coated with a metal oxide or a metal oxychloride, such as titanium dioxide or bismuth oxychloride, and optionally further color-imparting substances, such as iron oxides, Prussian blue, ultramarine, carmine etc. and where the color can be determined by varying the layer thickness. Such pigments are sold, for example, under the trade names Rona®, Colorona®, Dichrona® and Timiron® by Merck, Germany. In at least one embodiment, the pigment is selected from the group consisting of organic pigments such as sepia, gamboge, bone charcoal, Cassel brown, indigo, chlorophyll and other plant pigments. In at least one embodiment, the pigment is selected from the group consisting of synthetic organic pigments such as azo pigments, anthraquinoids, indigoids, dioxazine, quinacridone, phthalocyanine, isoindolinone, perylene and perinone, metal complex, alkali blue and diketopyrrolopyrrole pigments. In at least one embodiment, the formulation comprises from 0.01 wt.-% to

10 wt.-%, preferably from 0.05 wt.-% to 5 wt.-%, of at least one particulate substance. Suitable substances are, for example, substances which are solid at room temperature (25 °C) and are in the form of particles. In at least one embodiment, the particulate substance is selected from the group consisting of silica, silicates, aluminates, clay earths, mica, insoluble salts, in particular insoluble inorganic metal salts, metal oxides, e.g. titanium dioxide, minerals and insoluble polymer particles are suitable. The particles may be present in the formulation in undissolved, preferably stably dispersed form, and, following application to the keratin substrate and evaporation of the solvent, can deposit on the substrate in solid form. A stable dispersion can be achieved by providing the formulation with a yield point which is large enough to prevent the solid particles from sinking. An adequate yield point can be established using suitable gel formers in a suitable amount. In at least one embodiment, the particulate substance is selected from the group consisting of silica (silica gel, silicon dioxide) and metal salts, in particular inorganic metal salts, where silica is particularly preferred. Metal salts are, for example, alkali metal or alkaline earth metal halides, such as sodium chloride or potassium chloride; alkali metal or alkaline earth metal sulfates, such as sodium sulfate or magnesium sulfate.

In at least one embodiment, the formulation comprises a direct dye. Preferred among the direct dyes are the following compounds, alone or in combination with one another: Hydroxyethyl-2-nitro-p-toluidine, 2-hydroxyethylpicramic acid,

4-nitrophenylaminourea, tri(4-amino-3-methylphenyl)carbenium chloride (Basic Violet 2), 1 ,4-di-amino-9,10-anthracenedione (Disperse Violet 1 ), 1 -(2-hydroxy- ethyl)amino-2-nitro-4-[di(2-hydroxyethyl)amino]benzene (HC Blue No. 2), 4-[ethyl- (2-hydroxyethyl)amino]-1 -[(2-hydroxyethyl)amino]-2-nitrobenzene hydrochloride (HC Blue No. 12), 1 -amino-4-[di(2-hydroxyethyl)amino]-2-nitrobenzene

hydrochloride (HC Red No. 13), 4-amino-1 -[(2-hydroxyethyl)amino]-2-nitrobenzene (HC Red No. 3), 4-amino-3-nitrophenol, 4-[(2-hydroxyethyl)amino]-3-nitrophenol, 1-amino-5-chloro-4-[(2,3-dihydroxypropyl)amino]-2-nitrobenzene (HC Red No. 10),

5-chloro-1 ,4-[di(2,3-dihydroxypropyl)amino]-2-nitrobenzene (HC Red No. 11 ), 2-chloro-6-ethylamino-4-nitrophenol, 2-amino-6-chloro-4-nitrophenol,

4-[(2-hydroxyethyl)amino]-3-nitro-1 -trifluoromethylbenzene (HC Yellow No. 13), 8-amino-2-bromo-5-hydroxy-4-imino-6-{[3-(tnmethylammonio)-phenyl]annino}- 1 (4H)-naphthalenone chloride (C.l. 56059; Basic Blue No. 99),

1 -[(4-aminophenyl)azo]-7-(trimethylammonio)-2-naphthol chloride (C.l. 12250; Basic Brown No. 16), 1 -[(4-amino-2-nitrophenyl)azo]-7-(trimethylannnnonio)-2- naphthol chloride (Basic Brown No. 17), 2-hydroxy-1 -[(2-methoxyphenyl)azo]-7- (trimethylamnnonio)naphthalene chloride (C.l. 12245; Basic Red No. 76), 3-methyl-

1 -phenyl-4-{[3-(trimethylannnnonio)phenyl]azo}pyrazol-5-one chloride (C.l. 12719; Basic Yellow No. 57) and 2,6-diamino-3-[(pyridin-3-yl)azo]pyridine as well as the salts thereof. Particularly preferred among the aforesaid direct dyes are the following compounds, alone or in combination with one another: hydroxyethyl-2- nitro-p-toluidine, 2-hydroxyethylpicramic acid, 4-nitrophenylaminourea, tri(4-amino-

3-methylphenyl)carbenium chloride (Basic Violet 2), 1 ,4-di-amino-9,10- anthracenedione (Disperse Violet 1 ), 1 -(2-hydroxy-ethyl)amino-2-nitro-4-[di(2- hydro-xyethyl)amino]benzene (HC Blue No. 2), 4-[ethyl-(2-hydroxyethyl)amino]-1 - [(2-hydroxyethyl)amino]-2-nitrobenzene hydrochloride (HC Blue No. 12), 1 -amino-

4-[di(2-hydroxyethyl)amino]-2-nitrobenzene hydrochloride (HC Red No. 13), 4-amino-1 -[(2-hydroxyethyl)amino]-2-nitrobenzene (HC Red No. 3), 4-amino-3- nitrophenol, 4-[(2-hydroxyethyl)amino]-3-nitrophenol, 1 -amino-5-chloro-4-[(2,3- dihydroxypropyl)amino]-2-nitrobenzene (HC Red No. 10), 5-chloro-1 ,4-[di(2,3- dihydroxypropyl)- amino]-2-nitrobenzene (HC Red No. 1 1 ), 2-chloro-6-ethylamino- 4-nitrophenol, 2-amino-6-chloro-4-nitrophenol, 4-[(2-hydroxyethyl)amino]-3-nitro-1 - trifluoromethylbenzene (HC Yellow No. 13), 8-amino-2-bromo-5-hydroxy-4-imino- 6-{[3-(trimethylammonio)-phenyl]amino}-1 (4H)-naphthalenone chloride (C.l.

56059; Basic Blue No. 99), 1 -[(4-aminophenyl)azo]-7-(trimethylammonio)-2- naphthol chloride (C.l. 12250; Basic Brown No. 16), 1 -[(4-amino-2- nitrophenyl)azo]-7-(trimethylammonio)-2-naphthol chloride (Basic Brown No. 17),

2-hydroxy-1 -[(2-methoxyphenyl)azo]-7-(trimethylammonio)naphthalene chloride (C.l. 12245; Basic Red No. 76), 3-methyl-1 -phenyl-4-{[3- (trimethylammonio)phenyl]azo}pyrazol-5-one chloride (C.l. 12719; Basic Yellow No. 57) and 2,6-diamino-3-[(pyridin-3-yl)azo]pyridine as well as the salts thereof.

In at least one embodiment, the total quantity of direct dyes in the formulation amounts to 0.01 to 15 wt.-%, preferably 0.1 to 10 wt.-%, most preferred 0.5 to 8 wt.-%.

In at least one embodiment, the formulation comprises a conditioning agent. In at least one embodiment, the conditioning agent is a water insoluble, water dispersible, non-volatile, liquid that forms emulsified, liquid particles. In at least one embodiment, the conditioning agent is a silicone (e.g., silicone oil, cationic silicone, silicone gum, high refractive silicone, and silicone resin), an organic conditioning oil (e.g., hydrocarbon oils, polyolefins, and fatty esters), a cationic conditioning surfactant, a high melting point fatty compound, or combinations thereof.

In at least one embodiment, the conditioning agent is a silicone, and wherein the formulation comprises from 0.01 % to 10 %, or from 0.1 % to 5 % silicone conditioning agent, by total weight of the formulation. Suitable silicone conditioning agents, and optional suspending agents for the silicone, are described in

US-5,104,646. In at least one embodiment, the formulation comprises a silicone gum selected from the group consisting of polydimethylsiloxane,

(polydimethylsiloxane) (methylvinylsiloxane) copolymer, poly(dimethylsiloxane) (diphenylsiloxane) (methylvinylsiloxane) copolymer, and mixtures thereof.

In at least one embodiment, the formulation comprises a terminal aminosilicone. "Terminal aminosilicone" as defined herein means silicone comprising one or more amino groups at one or both ends of the silicone backbone. In at least one embodiment, the formulation is substantially free of any silicone compound comprising pendant amino groups. In an embodiment, the formulation is

substantially free of any silicone compound other than terminal aminosilicones. In at least one embodiment, the amino group at least one terminus of the silicone backbone of the terminal aminosilicone is selected from the group consisting of primary amines, secondary amines and tertiary amines. In at least one

embodiment, the formulation comprises a terminal aminosilicone conforming to Formula (S):

wherein

G is hydrogen, phenyl, hydroxy, or C₁-Cs alkyl, preferably methyl;

a is an integer having a value from 1 to 3, preferably 1 ; b is 0, 1 or 2,

preferably 1 ;

n is a number from 0 to 1 ,999;

R^F is a monovalent radical conforming to the general formula CqH2ql, wherein q is an integer having a value from 2 to 8 and L is selected from the following groups: -N(R^T)CH2-CH2-N(R^T)₂; -N(R^T)₂; -N(R^T)₃A ; -N(R^T)CH₂- CH2-NR^TH2A ; wherein R^T is hydrogen, phenyl, benzyl, or a saturated hydrocarbon radical, preferably an alkyl radical from having from 1 to 20 carbon atoms; A- is a halide ion.

In at least one embodiment, the terminal aminosilicone corresponding to Formula (S) has a = 1 , q = 3, G = methyl, n is from 1000 to 2500, alternatively from 1500 to 1700; and L is -N(CH3)2. A suitable terminal aminosilicone corresponding to Formula (III) has a = O, G = methyl, n is from 100 to 1500, or from 200 to 800, and L is selected from the following groups: -N(R^T)CFl2-CFl2-N(R^T)2; -N(R^T)2; -N(R^T)3A ; -N(R^T)CFl2-CFl2-NR^TFl2A-; wherein R^T is hydrogen, phenyl, benzyl, or a saturated hydrocarbon radical, preferably an alkyl radical from having from 1 to 20 carbon atoms; A- is a halide ion, alternatively L is -NFI2. In at least one embodiment, the terminal aminosilicone is selected from the group consisting of bis-aminomethyl dimethicone, bisaminoethyl dimethicone, bis-aminopropyl dimethicone,

bis-aminobutyl dimethicone, and mixtures thereof. In an embodiment, the viscosity of the terminal aminosilicone is from 1 ,000 to 30,000 cPs, or from 5,000 to

20,000 cPs measured at 25 °C.

In at least one embodiment, the formulation comprises from 0.1 % to 20 %, or from 0.5 % to 10 %, or from 1 % to 6 % terminal aminosilicone, by total weight of the formulation.

In at least one embodiment, the formulation comprises a high melting point fatty compound. The high melting point fatty compound has a melting point of 25 °C or higher. In at least one embodiment, the high melting point fatty compound is selected from the group consisting of a fatty alcohol, fatty acid, fatty alcohol derivative, fatty acid derivative, and mixtures thereof. Non-limiting examples of the high melting point compounds are found in International Cosmetic Ingredient Dictionary, Fifth Edition, 1993, and CTFA Cosmetic Ingredient Flandbook, Second Edition, 1992. The formulation may comprise from 0.1 % to 40 %, or from 1 % to 30 %, or from 1.5 % to 16 %, or from 1.5 % to 8 % of a high melting point fatty compound, by total weight of the formulation. This is advantageous in view of providing improved conditioning benefits such as slippery feel during the application to wet hair, softness and moisturized feel on dry hair. In at least one embodiment, the fatty alcohol is selected from the group consisting of: cetyl alcohol, stearyl alcohol, behenyl alcohol, and mixtures thereof. In at least one embodiment, the formulation comprises a linear fatty alcohol, wherein the linear fatty alcohol is comprised in a lamellar gel matrix. A lamellar gel matrix is suitable for providing various conditioning benefits such as slippery feel during the application to wet hair and softness and moisturized feel on dry hair. The linear fatty alcohol may comprise from 8 to 24 carbon atoms. In an embodiment, the linear fatty alcohol is selected from the group consisting of: cetyl alcohol, stearyl alcohol, and mixtures thereof. In an embodiment, the weight ratio of total linear fatty alcohol to terminal aminosilicone is from 0.5:1 to 10:1 , or from 1 :1 to 5:1 , or from 2.4:1 to 2.7:1.

In at least one embodiment, the lamellar gel matrix comprises a cationic conditioning surfactant and a high melting point fatty compound. In view of providing the lamellar gel matrix, the cationic conditioning surfactant and the high melting point fatty compound are contained at a level such that the weight ratio of the cationic surfactant to the high melting point fatty compound is in the range of from 1 : 1 to 1 : 10, or from 1 : 1 to 1 :6.

In at least one embodiment, the formulation comprises a cationic conditioning surfactant. In at least one embodiment, the formulation comprises from 0.05 % to 3.0 %, or from 0.075 % to 2.0 %, or from 0.1 % to 1.0 %, of cationic conditioning surfactant by total weight of the formulation. In at least one embodiment, the cationic conditioning surfactant is comprised in a lamellar gel matrix. In other words, the formulation comprises a lamellar gel matrix and the lamellar gel matrix comprises the cationic conditioning surfactant. In an embodiment, cationic conditioning surfactant is according to Formula (C):

wherein at least one of R⁷¹ , R⁷², R⁷³ and R⁷⁴ is selected from an aliphatic group of from 8 to 30 carbon atoms, an aromatic, alkoxy, polyoxyalkylene, alkylamido, hydroxyalkyl, aryl, or an alkylaryl group having up to 22 carbon atoms;

the remainder of R⁷¹ , R⁷², R⁷³ and R⁷⁴ are independently selected from the group consisting of an aliphatic group consisting of from 1 to 22 carbon atoms, and an aromatic, alkoxy, polyoxyalkylene, alkylamido, hydroxyalkyl, aryl or alkylaryl group having up to 22 carbon atoms;

X is selected from the group consisting of: halogen, acetate, citrate, lactate, glycolate, phosphate, nitrate, sulfonate, sulfate, alkylsulfate, alkyl sulfonate radicals, and combinations thereof.

In at least one embodiment, the cationic conditioning surfactant is selected from the group consisting of behenyl trimethyl ammonium chloride, methyl sulfate or ethyl sulfate, and stearyl trimethyl ammonium chloride, methyl sulfate or ethyl sulfate. It is believed that a longer alkyl group provides improved smoothness and soft feeling on wet and dry hair, compared to cationic surfactants with a shorter alkyl group. It is also believed that such cationic surfactants can provide reduced irritation, compared to those having a shorter alkyl group.

In at least one embodiment, the cationic surfactant is a di-long alkyl quatemized ammonium salt selected from the group consisting of: dialkyl (14 - 18) dimethyl ammonium chloride, ditallow alkyl dimethyl ammonium chloride, dihydrogenated tallow alkyl dimethyl ammonium chloride, distearyl dimethyl ammonium chloride, dicetyl dimethyl ammonium chloride, and mixtures thereof.

In at least one embodiment, the cationic surfactant is a tertiary amido amine having an alkyl group of from 12 to 22 carbons. The tertiary amido amine may be selected from the group consisting of stearamidopropyldimethyl-,

stearamidopropyldiethyl-, stearamidoethyldiethyl-, stearamidoethyldimethyl-, palmitamidopropyldimethyl-, palmitamidopropyldiethyl-, palmitamidoethyldiethyl-, palmitamidoethyldimethyl-, behenamidopropyldimethyl -,

behenamidopropyldiethyl-, behenamidoethyldiethyl-, behenamidoethyldimethyl-, arachidamidopropy Idimethy 1-, arachidamidopropyldiethyl-,

arachidamidoethyldiethyl-, and arachidamidoethyldimethyl-amine,

diethylaminoethylstearamide, and mixtures thereof. A tertiary amido amine may be used in combination with an acid. The acid is typically used as a salt-forming anion. In an embodiment, the acid is selected from the group consisting of lactic acid, malic acid, hydrochloric acid, 1 -glumatic acid, acetic acid, citric acid, and mixtures thereof.

In at least one embodiment, the cationic surfactant is selected from the group consisting of cetyltrimonium chloride (CTAC), stearyltrimonium chloride (STAC), behentrimonium methosulfate, stearoylamidopropyldimethyl amine (SAPDMA), distearyldimethylammonium chloride, and mixtures thereof.

In at least one embodiment, the formulation comprises a surfactant system. In at least one embodiment, the surfactant system comprises a surfactant selected from the group consisting of anionic surfactants, cationic surfactants, non-ionic surfactants, zwitterionic surfactants and/or amphoteric surfactants. In at least one embodiment, the formulation comprises a total amount of surfactant of from 0.01 wt.-% to 70 wt.-%, from 0.1 wt.-% to 40 %, from 1 wt.-% to 30 %, from

2 wt.-% to 20 wt.-%.

In at least one embodiment, the formulation comprises an anionic surfactant. In at least one embodiment, the anionic surfactant is selected from the group consisting of (C₁o-C2o)-alkyl and alkylene carboxylates, alkyl ether carboxylates, fatty alcohol sulfates, fatty alcohol ether sulfates, alkylamide sulfates and sulfonates, fatty acid alkylamide polyglycol ether sulfates, alkanesulfonates and

hydroxyalkanesulfonates, olefinsulfonates, acyl esters of isethionates, a-sulfo fatty acid esters, alkylbenzenesulfonates, alkylphenol glycol ether sulfonates, sulfosuccinates, sulfosuccinic monoesters and diesters, fatty alcohol ether phosphates, protein/fatty acid condensation products, alkyl monoglyceride sulfates and sulfonates, alkylglyceride ether sulfonates, fatty acid methyltaurides, fatty acid sarcosinates, sulforicinoleates, acylglutamates, and mixtures thereof. The anionic surfactants (and their mixtures) can be used in the form of their water-soluble or water-dispersible salts, examples being the sodium, potassium, magnesium, ammonium, mono, di-, and triethanolammonium, and analogous alkylammonium salts. In at least one embodiment, the anionic surfactant is the salt of an anionic surfactant comprising 12 to 14 carbon atoms. In at least one embodiment, the anionic surfactant is selected from the group consisting of sodium lauryl sulfate, sodium laureth sulfate, sodium tridecyl sulfate, sodium trideceth sulfate, sodium myristyl sulfate, sodium myreth sulfate, and mixtures thereof.

In at least one embodiment, the formulation comprises an acylglycinate surfactant. In at least one embodiment, the acylglycinate surfactant conforms to the

formula (Y):

wherein

R^1a is a linear or branched, saturated alkanoyl group having 6 to 30, preferably 8 to 22, particularly preferably 8 to 18, carbon atoms or is a linear or branched, mono- or polyunsaturated alkenoyl group having 6 to 30, preferably 8 to 22, more preferably 12 to 18 carbon atoms, and Q_a ⁺ is a cation.

In at least one embodiment, Q_a ⁺ is selected from the group consisting of Li⁺, Na⁺, a monoalkylammmonium ion, a dialkylammonium ion,

a trialkylammonium ion and a tetraalkylammonium ion, or combinations thereof. Optionally R^1a is independently from one another, are (C₁-C22)-alkyl radicals or (C2-C₁o)-hydroxyalkyl radicals. In at least one embodiment, the acylglycinate surfactant is selected from sodium cocoylglycinate and potassium cocoylglycinate. In at least one embodiment, the acylglycinate surfactant is selected from those conforming to formula (Y), wherein R is C12 alkyl or CM alkyl. In at least one embodiment, the acylglycinate surfactant is selected from those conforming to formula (Y), wherein R is C16 alkyl or C18 alkyl.

In at least one embodiment, the formulation comprises a glutamate surfactant corresponding to formula (Z) or a salt thereof:

wherein

R’ is

wherein M⁺ is a cation; and wherein R is a linear or branched, saturated alkanoyl group having 6 to 30, preferably 8 to 22, more preferably 8 to 18, carbon atoms or is a linear or branched, mono- or polyunsaturated alkenoyl group having 6 to 30, preferably 8 to 22 and more preferably 12 to 18 carbon atoms. In at least one embodiment, M⁺ is a metal cation. In at least one embodiment, M⁺ is selected from the group consisting of Li⁺, Na⁺, K⁺, Mg⁺⁺, Ca⁺⁺, Al⁺⁺⁺, NhV, a monoalkylammmonium ion, a dialkylammonium ion, a trialkylammonium ion and a tetraalkylammonium ion, or combinations thereof. In at least one embodiment, the glutamate surfactant is selected from sodium cocoyl glutamate and potassium cocoyl glutamate. In at least one embodiment, the glutamate surfactant is selected from those conforming to formula (Z), wherein R is C12 alkyl or C14 alkyl. In at least one embodiment, the glutamate surfactant is selected from those conforming to formula (Z), wherein R is C16 alkyl or C18 alkyl.

In at least one embodiment, the formulation comprises from 0.01 wt.-% to

30 wt.-%, or 1 wt.-% to 25 wt.-%, preferably from 5 wt.-% to 20 wt.-%, more preferably from 12 wt.-% to 18 wt.-% anionic surfactant.

In at least one embodiment, the formulation comprises a non-ionic surfactant. In at least one embodiment, the non-ionic surfactant has an HLB (Hydrophilic Lipophilic Balance) of greater than 12. Optionally, the non-ionic surfactant is selected from the group consisting of ethoxylated or ethoxylated/propoxylated fatty alcohols with a fatty chain comprising from 12 to 22 carbon atoms, ethoxylated sterols, such as stearyl- or lauryl alcohol (EO-7), PEG-16 soya sterol or PEG-10 soya sterol, polyoxyethylene polyoxypropylene block polymers (poloxamers), and mixtures thereof.

In at least one embodiment, the non-ionic surfactant is selected from the group consisting of ethoxylated fatty alcohols, fatty acids, fatty acid glycerides or alkylphenols, in particular addition products of from 2 to 30 mol of ethylene oxide and/or 1 to 5 mol of propylene oxide onto Cs- to C22-fatty alcohols, onto C12- to C22-fatty acids or onto alkyl phenols having 8 to 15 carbon atoms in the alkyl group, C12- to C22-fatty acid mono- and diesters of addition products of from 1 to 30 mol of ethylene oxide onto glycerol, addition products of from 5 to 60 mol of ethylene oxide onto castor oil or onto hydrogenated castor oil, fatty acid sugar esters, in particular esters of sucrose and one or two Cs- to C22-fatty acids, INCI: Sucrose Cocoate, Sucrose Dilaurate, Sucrose Distearate, Sucrose Laurate, Sucrose Myristate, Sucrose Oleate, Sucrose Palmitate, Sucrose Ricinoleate, Sucrose Stearate, esters of sorbitan and one, two or three Cs- to C22-fatty acids and a degree of ethoxylation of from 4 to 20, polyglyceryl fatty acid esters, in particular of one, two or more Cs- to C22-fatty acids and polyglycerol having preferably 2 to 20 glyceryl units, alkyl glucosides, alkyl oligoglucosides and alkyl polyglucosides having Cs to C22-alkyl groups, e.g. decylglucoside or laurylglucoside, and mixtures thereof.

In at least one embodiment, the non-ionic surfactant is selected from the group consisting of fatty alcohol ethoxylates (alkylpolyethylene glycols), alkylphenol polyethylene glycols, alkyl mercaptan polyethylene glycols, fatty amine ethoxylates (alkylaminopolyethylene glycols), fatty acid ethoxylates (acylpolyethylene glycols), polypropylene glycol ethoxylates (Pluronics^®), fatty acid alkylol amides, (fatty acid amide polyethylene glycols), N-alkyl-, N-alkoxypolyhydroxy-fatty acid amide, sucrose esters, sorbitol esters, polyglycol ethers, and mixtures thereof.

In at least one embodiment, the formulation comprises a fatty N-methyl-N- glucamide surfactant, wherein the fatty N-methyl-N-glucamide surfactant conforms to the formula (X):

wherein R is a linear or branched alkyl or alkenyl group having from 3 to 30 carbon atoms. In at least one embodiment, R is an alkyl group having from 3 to 30 carbon atoms. In at least one embodiment, R is a saturated aliphatic hydrocarbon group which can be linear or branched and can have from 3 to 20 carbon atoms in the hydrocarbon chain, preferably linear or branched. Branched means that a lower alkyl group such as methyl, ethyl or propyl is present as substituent on a linear alkyl chain. In at least one embodiment, R is selected from the group consisting of

1 -propyl, 2-propyl, 1 -butyl, 2-butyl, 2-methyl-1 -propyl (isobutyl), 2-methyl-2-propyl (tert-butyl), 1 -pentyl, 2-pentyl, 3-pentyl, 2-methyl-1 -butyl, 3-methyl-1 -butyl,

2-methyl-2-butyl, 3-methyl-2-butyl, 2, 2-dimethyl-1 -propyl, 1 -hexyl, 2-hexyl, 3-hexyl,

2-methyl-1 -pentyl, 3-methyl-1 -pentyl, 4-methyl-1 -pentyl, 2-methyl-2-pentyl,

3-methyl-2-pentyl, 4-methyl-2-pentyl, 2-methyl-3-pentyl, 3-methyl-3-pentyl, 2.2-dimethyl-1 -butyl, 2,3-dimethyl-1 -butyl, 3,3-dimethyl-1 -butyl, 2-ethyl-1 -butyl,

2.3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, 1 -heptyl, 1 -octyl, 1 -nonyl, 1 -decyl, 1 -undecyl, 1 -dodecyl, 1 -tetradecyl, 1 -hexadecyl and 1 -octadecyl. Suitable fatty N-methyl-N-glucamide surfactants are described in WO2013/178700 and

EP0550637, which are incorporated herein by reference. In at least one

embodiment, the N-methyl-N-glucamide surfactant is selected from those conforming to formula (X), wherein R is C12 alkyl or CM alkyl. In at least one embodiment, the N-methyl-N-glucamide surfactant is selected from those conforming to formula (X), wherein R is C16 alkyl or C18 alkyl.

In at least one embodiment, the formulation comprises from 1 wt.-% to 20 wt.-%, more preferably from 2 wt.-% to 10 wt.-%, even more preferably from 3 wt.-% to 7 wt.-% non-ionic surfactant.

In at least one embodiment, the amphoteric surfactants are selected from the group consisting of N-(C₁₂-C₁₈)-alkyl-β-aminopropionates and N-(C₁₂-C₁₈)-alkyl-β- iminodipropionates as alkali metal salts and mono-, di-, and trialkylammonium salts; N-acylaminoalkyl-N,N-dimethylacetobetaine, preferably N-(C₈- C₁₈)- acylaminopropyl-N,N-dimethylacetobetaine, (C₁₂- C₁₈)-alkyl-dimethyl- sulfopropylbetaine, amphosurfactants based on imidazoline (trade name: Miranol^®, Steinapon^®), preferably the sodium salt of 1 -(β-carboxymethyloxyethyl)-1 - (carboxymethyl)-2-laurylimidazolinium; amine oxide, e.g., (C₁₂-C₁₈)-alkyl-dimethyl- amine oxide, fatty acid amidoalkyldimethylamine oxide, and mixtures thereof.

In at least one embodiment, the formulation comprises a betaine surfactant.

Optionally, the betaine surfactant is selected from C₈- to C₁₈-alkylbetaines. In at least one embodiment, the betaine surfactant is selected from the group consisting of cocodimethylcarboxymethylbetaine, lauryldimethylcarboxymethylbetaine, lauryldimethylalphacarboxyethylbetaine, cetyldimethylcarboxymethylbetaine, oleyldimethylgammacarboxypropylbetaine and laurylbis(2- hydroxypropyl)alphacarboxyethylbetaine and combinations thereof. Optionally, the betaine surfactant is selected from C₈- to C₁₈-sulfobetaines. In at least one embodiment, the betaine surfactant is selected from the group consisting of cocodimethylsulfopropylbetaine, stearyldimethylsulfopropylbetaine, lauryldimethyl- sulfoethylbetaine, laurylbis(2-hydroxyethyl)sulfopropylbetaine, and combinations thereof. Optionally, the betaine surfactant is selected from carboxyl derivatives of imidazole, the Cs- to C₁₈-alkyldimethylammonium acetates, the Cs- to

C₁₈-alkyldimethylcarbonylmethylammonium salts, and the Cs- to C₁₈-fatty acid alkylamidobetaines, and mixtures thereof. Optionally, the Cs- to C₁₈-fatty acid alkylamidobetaine is selected from coconut fatty acid amidopropylbetaine,

N-coconut fatty acid amidoethyl-N-[2-(carboxymethoxy)ethyl]glycerol (CTFA name: Cocoamphocarboxyglycinate), and mixtures thereof.

In at least one embodiment, the formulation comprises from 0.5 wt.-% to 20 wt.-%, preferably from 1 wt.-% to 10 wt.-% amphoteric surfactant.

In at least one embodiment, the formulation comprises a surfactant system. In at least one embodiment, the surfactant system comprises at least one surfactant selected from the group consisting of lauryl sulfate, laureth sulfate, cocoamido- propylbetaine, sodium cocoylglutamate, lauroamphoacetate, and mixtures thereof. In at least one embodiment, the surfactant system comprises sodium laureth sulphate, sodium lauryl sulphate, and optionally cocamidopropyl betaine. In at least one embodiment, the surfactant system comprises sodium laureth sulphate, Potassium Cocyl Glutamate, and cocamidopropyl betaine.

In at least one embodiment, the formulation further comprises a hairstyling polymer. In at least one embodiment, the hairstyling polymer is selected from the group consisting of: amphoteric hairstyling polymers, zwitterionic hairstyling polymers, anionic hairstyling polymers, non-ionic hairstyling polymers, cationic hairstyling polymers, and mixtures thereof. In at least one embodiment, the formulation comprises from 0.01 % to 20 %, or from 0.01 % to 16 %, or from 0.01 % to 10 %, or from 1 % to 8 %, or from 2 % to 6 % of hairstyling polymer.

In at least one embodiment, the hairstyling polymer is a water-compatible hairstyling polymer, alternatively a water-soluble hairstyling polymer. In at least one embodiment, the formulation is substantially free of a water-incompatible hairstyling polymer. An example of a water-incompatible hairstyling polymer includes an Acrylates/t-Butylacrylamide Copolymer which is a copolymer of tert-butyl acrylamide and one or more monomers of acrylic acid, methacrylic acid, or one of their simple esters (e.g. Ultrahold^® 8 from BASF). Balance^® CR from Akzo Nobel, which is an acrylates copolymer of two or more monomers of

(meth)acrylic acid or one of their simple esters, is water-compatible. The

octylacrylamide/acrylate/butylaminoethyl methacrylate copolymer Amphomer^® is also water-compatible. In at least one embodiment, the hairstyling polymer is a latex hairstyling polymer.

The formulation may comprise a cationic hairstyling polymer. In at least one embodiment, the cationic hairstyling polymers is selected from from group consisting of those with primary, secondary, tertiary or quaternary amino groups.

In at least one embodiment, the cationic hairstyling polymer has a cationic charge density, and wherein the cationic charge density is from 1 to 7 meq/g. In at least one embodiment, the cationic hairstyling polymer comprises quaternary amino groups. In at least one embodiment, the cationic hairstyling polymer is a homo- or copolymer where the quaternary nitrogen groups are contained either in the polymer chain or as substituents on one or more of the monomers. The

ammonium group-containing monomers can be copolymerized with non-cationic monomers. In at least one embodiment, the cationic hairstyling polymer comprises cationic monomers where the cationic monomers are unsaturated compounds that can undergo radical polymerization and which bear at least one cationic group. In at least one embodiment, the cationic monomers are selected from the group consisting of: ammonium-substituted vinyl monomers such as, for example, trialkylmethacryloxyalkylammonium, trial kylacryloxyalkylammonium,

dialkyldiallylammonium and quaternary vinylammonium monomers with cyclic, cationic nitrogen-containing groups such as pyridinium, imidazolium or quaternary pyrrolidones, e.g. alkylvinylimidazolium, alkylvinylpyridinium, or

alkylvinylpyrrolidone salts. The alkyl groups of these monomers may be lower alkyl groups such, as for example, C₁- to C₇-alkyl groups, and may also be are C₁- to C3-alkyl groups. In at least one embodiment, cationic hairstyling polymer comprises ammonium group-containing monomers being copolymerized with non-cationic monomers.

The non-cationic monomers may be selected from the group consisting of:

acrylamide, methacrylamide, alkyl- and dialkylacrylamide, alkyl- and

dialkylmethacrylamide, alkyl acrylate, alkyl methacrylate, vinylcaprolactone, vinylcaprolactam, vinylpyrrolidone, vinyl esters, for example vinyl acetate, vinyl alcohol, propylene glycol or ethylene glycol, and mixture thereof. The alkyl groups of these monomers may be C₁- to C₇-alkyl groups, and may be C₁- to C3-alkyl groups. In at least one embodiment, cationic hairstyling polymer comprises at least one quaternary amino group. Suitable polymers with at least one quaternary amino group include, for example, those described in the CTFA Cosmetic

Ingredient Dictionary under the designations‘polyquaternium’ such as

methylvinylimidazolium chloride/vinylpyrrolidone copolymer (polyquaternium-16) or quaternized vinylpyrrolidone/dimethylaminoethyl methacrylate copolymer

(polyquaternium-11 ; Gafquat^® 755N-PW from ISP) as well as quaternary silicone polymers or silicone oligomers such as, for example, silicone polymers with quaternary end groups (quatemium-80).

In at least one embodiment, the hairstyling polymer is a cationic hairstyling polymer being of synthetic origin. In at least one embodiment, the cationic hairstyling polymers of synthetic origin are selected from the group consisting of: poly(dimethyldiallylammonium chloride); copolymers from acrylamide and dimethyldiallylammonium chloride; quaternary ammonium polymers, formed by the reaction of diethyl sulfate with a copolymer from vinylpyrrolidone and

dimethylaminoethyl methacrylate, especially vinylpyrrolidone/dimethylaminoethyl methacrylate methosulfate copolymer (e.g. Gafquat^® 755 N; Gafquat^® 734);

quaternary ammonium polymers from methylvinylimidazolium chloride and vinylpyrrolidone (e.g. Luviquat^® HM 550 from BASF; Luviquat^® Hold from BASF; polyquaternium-46 [vinylcaprolactam {VCap}, vinylpyrrolidone {VP} and

quaternized vinylimidazole {QVI}] from BASF; Luviquat^® FC 905 from BASF

[polyquaternium-16]); Luviquat Supreme^® from BASF (polyquaternium-68, quaternised copolymer of vinyl pyrrolidone, methacrylamides, vinyl imidazole and quaternized vinyl imidazole); polyquaternium-35; polyquaternium-57; polymers from trimethylammonium ethyl methacrylate chloride; terpolymers from

dimethyldiallylammonium chloride, sodium acrylate and acrylamide (e.g. Merquat^® Plus 3300); copolymers from vinylpyrrolidone, dimethylaminopropyl

methacrylamide, and methacryloylaminopropyllauryldimethylammonium chloride; terpolymers from vinylpyrrolidone, dimethylaminoethyl methacrylate, and

vinylcaprolactam (e.g. Gaffix^® VC 713);

vinylpyrrolidone/methacrylamidopropyltrimethylammonium chloride copolymers (e.g. Gafquat^® HS 100); copolymers from vinylpyrrolidone and dimethylaminoethyl methacrylate; copolymers from vinylpyrrolidone, vinylcaprolactam, and

dimethylaminopropylacrylamide; poly- or oligoesters formed from at least one first type of monomer that is selected from hydroxyacids substituted with at least one quaternary ammonium group; dimethylpolysiloxane substituted with quaternary ammonium groups in the terminal positions; and mixtures thereof.

In at least one embodiment, the hairstyling polymer is a cationic hairstyling polymer being of natural origin. In at least one embodiment, the cationic hairstyling polymers being of natural origin are selected from the group consisting of: cationic derivatives of polysaccharides, for example, cationic cellulose derivatives, starch, guar, and mixtures thereof. Cationic derivatives of polysaccharides may be represented by the general formula:

wherein

G is an anhydroglucose residue, for example, starch or cellulose anhydroglucoses;

B is a divalent bonding group, for example, alkylene, oxyalkylene, polyoxyalkylene or hydroxyalkylene;

R^a, R^b and R^c are, independently from one another, alkyl, aryl, alkylaryl, arylalkyl, alkoxyalkyl or alkoxyaryl, any of which can have up to 22 carbon atoms, wherein the total number of carbon atoms in R^a, R^b and R^c is may be a maximum of 20. In at least one embodiment, the hairstyling polymer is a cationic cellulose derivative being selected from the group consisting of: those that have at least one quaternary ammonium group, e.g. a copolymer made of hydroxyethyl cellulose and diallyldimethyl ammonium chloride (polyquaternium-4), or the reaction product made of hydroxyethyl cellulose and an epoxide substituted with a trialkyl ammonium group (polyquaternium-10), wherein the alkyl groups can have 1 to 20 carbon atoms, or wherein the alkyl group is methyl. In at least one embodiment, the hairstyling polymer is a cationic cellulose derivative having a molecular weight of from 100,000 Da to 600,000 Da, or from 200,000 Da to 400,000 Da. In at least one embodiment, the cationic cellulose derivative has a nitrogen content, wherein the nitrogen content is from 0.5 % to 4 %, or from aout 1 .5 % to 3 %. In at least one embodiment, the hairstyling polymer is a cationic cellulose derivative being polyquaternium-4. Polyquaternium-4 is sold under the trade names Celquat^® HIOO and Celquat^® L200, of which Celquat^® L200 is especially preferred.

In at least one embodiment, the hairstyling polymer is a cationic latex hairstyling polymer. In at least one embodiment, the cationic hairstyling polymer is selected from the group consisting of: polyquaternium-4, polyquaternium-1 1 ,

polyquaternium-16, polyquaternium-68, mixtures thereof, and mixtures of polyquaternium-68 with a non-ionic hairstyling polymer. In at least one

embodiment, the hairstyling polymer is selected from the group consisting of:

polyquaternium-4, polyquaternium-1 1 , polyquaternium-68, and mixtures thereof. In at least one embodiment, the formulation comprises a chitosan, a chitosan salt or a chitosan derivative. In at least one embodiment, the formulation comprises less than 0.1 % by weight chitosan, chitosan salts and chitosan derivatives. In another embodiment, the formulation is substantially free from chitosan, chitosan salts and chitosan derivatives. In at least one embodiment, the formulation comprises a hairstyling polymer selected from the group consisting of: polyquaternium-4, polyquaternium-1 1 , polyquaternium-16, polyquaternium-68, mixtures thereof; or from the group consisting of: polyquaternium-4, polyquaternium-68, and mixtures thereof. In at least one embodiment, the formulation comprises a hairstyling polymer selected from the group consisting of: polyquaternium-4, polyquaternium- 11 , polyquaternium-68, mixtures thereof; or from the group consisting of:

polyquaternium-4, polyquaternium-68, and mixtures thereof.

In at least one embodiment, the formulation comprises less than 0.5 wt.-% of a cationic hairstyling polymer by total weight of the formulation.

In at least one embodiment, the formulation comprises an amphoteric or zwitterionic hairstyling polymer. In at least one embodiment, the amphoteric or zwitterionic hairstyling polymer is selected from the group consisting of:

copolymers formed from alkylacrylamide, alkylaminoalkyl methacrylate, and two or more monomers from acrylic acid and methacrylic acid as well as, if necessary, their esters, especially copolymers from octylacrylamide, acrylic acid,

butylaminoethyl methacrylate, methyl methacrylate and hydroxypropyl

methacrylate (octylacrylamide/acrylate/butylaminoethyl methacrylate copolymer, for example Amphomer^® from Akzo Nobel); copolymers, that are formed from at least one of a first type of monomer that possesses quaternary amino groups and at least one of a second type of monomer that possesses acid groups; copolymers from fatty alcohol acrylates, alkylamine oxide methacrylate and at least one monomer selected from acrylic acid and methacrylic acid as well as, if necessary, acrylic acid esters and methacrylic acid esters, especially copolymers from lauryl acrylate, stearyl acrylate, ethylamine oxide methacrylate and at least one monomer selected from acrylic acid and methacrylic acid as well as, if necessary, their esters; copolymers from methacryloyl ethyl betaine and at least one monomer selected from methacrylic acid and methacrylic acid esters; copolymers from acrylic acid, methyl acrylate and methacrylamidopropyltrimethylammonium chloride (polyquaternium-47); copolymers from

acrylamidopropyltrimethylammonium chloride and acrylates or copolymers from acrylamide, acrylamidopropyltrimethylammonium chloride,

2-amidopropylacrylamide sulfonate and dimethylaminopropylamine

(polyquaternium-43); oligomers or polymers, producible from quaternary crotonoylbetaines or quaternary crotonoylbetaine esters. In at least one

embodiment, the formulation comprises an amphoteric or zwitterionic latex hairstyling polymer. In at least one embodiment, the hairstyling polymer is selected from the group consisting of: polyquaternium-47,

octylacrylamide/acrylate/butylaminoethyl methacrylate copolymers, and mixtures thereof.

The hairstyling formulation may comprise an anionic hairstyling polymer. In at least one embodiment, the anionic hairstyling polymer is selected from the group consisting of: acrylates copolymers of two or more monomers of (meth)acrylic acid or one of their simple esters (e.g. Balance^® CR from Akzo Nobel);

acrylates/hydroxyesters acrylates copolymers including those being copolymers of butyl acrylate, methyl methacrylate, methacrylic acid, ethyl acrylate and

hydroxyethyl methacrylate (e.g. Acudyne™ 1000 from Dow Personal Care);

terpolymers of acrylic acid, ethyl acrylate, and N-tert-butylacrylamide; crosslinked or uncrosslinked vinyl acetate/croton ic acid copolymers; terpolymers of

tert-butylacrylate, ethyl acrylate and methacrylic acid; sodium

polystyrenesulfonate; copolymers of vinyl acetate, crotonic acid and vinyl propionate; copolymers of vinyl acetate, crotonic acid and vinyl neodecanoate; aminomethylpropanol/acrylate copolymers; copolymers of vinylpyrrolidone and at least one further monomer selected from among acrylic acid, methacrylic acid, acrylic acid esters and methacrylic acid esters; copolymers of methyl vinyl ether and maleic acid monoalkyl esters; aminomethylpropanol salts of copolymers of allyl methacrylate and at least one further monomer selected from among acrylic acid, methacrylic acid, acrylic acid esters and methacrylic acid esters; crosslinked copolymers of ethyl acrylate and methacrylic acid; copolymers of vinyl acetate, mono-n-butyl maleate and isobornyl acrylate; copolymers of two or more

monomers selected from among acrylic acid, methacrylic acid, acrylic acid esters and methacrylic acid esters, copolymers of octylacrylamide and at least one monomer selected from among acrylic acid, methacrylic acid, acrylic acid esters and methacrylic acid esters; polyesters of diglycol, cyclohexanedimethanol, isophthalic acid and sulfoisophthalic acid; polyurethanes; and copolymers of polyurethane and acrylates, e.g. polyurethane-14/AMP-acrylates polymer blend (e.g. DynamX^® from Akzo Nobel). Suitable polyester polymers include polyester-5 polymers, for example AQ^® 48 Ultra Polymer, (diglycol/CHDM/isophthalates/SIP copolymer [a copolymer of diethylene glycol, 1 ,4-cyclohexanedimethanol and the simple esters of isophthalic acid and sulfoisophthalic acid]), AQ^® 55 S, and AQ^® 38 S, all from Eastman Chemical Company. Also suitable is a

polyvinylmethacrylic acid/maleic acid copolymer (Omnirez^® 2000 from ISP).

Anionic latex hairstyling polymers are also suitable. In at least one embodiment, the anionic hairstyling polymer is selected from the group consisting of:

polyurethane-1 (e.g. Luviset^® P.U.R. from BASF), polyurethane-14/AMP-acrylates copolymer blend (e.g. DynamX^® from Akzo Nobel), acrylates copolymers of two or more monomers of (meth)acrylic acid or one of their simple esters (e.g. Balance^® CR from Akzo Nobel), and mixtures thereof. In at least one embodiment, the anionic hairstyling polymer is Polyurethane-1 .

The formulation may comprise a non-ionic hairstyling polymer. In at least one embodiment, the formulation comprises a non-ionic hairstyling polymer, wherein are non-ionic hairstyling polymer is a homo- or copolymer that is formed from at least one of the following monomers: vinylpyrrolidone, vinylcaprolactam, vinyl esters such as, for example, vinyl acetate, vinyl alcohol, acrylamide,

methacrylamide, alkyl- and dialkylacrylamide, alkyl- and dialkylmethacrylamide, alkyl acrylate, alkyl methacrylate, propylene glycol or ethylene glycol, where the alkyl groups in these monomers may be C₁- to C₇-alkyl groups or C₁- to C3-alkyl groups. In at least one embodiment, the formulation comprises a homopolymer selected from the group consisting of: vinylcaprolactam, vinylpyrrolidone,

N-vinylformamide and mixtures thereof. In at least one embodiment, the non-ionic hairstyling polymer is selected from the group consisting of: copolymers of vinylpyrrolidone and vinyl acetate, terpolymers of vinylpyrrolidone, vinyl acetate and vinyl propionate, polyacrylamides; polyvinyl alcohols as well as polyethylene glycol/polypropylene glycol copolymers; and mixtures thereof. In at least one embodiment, the non-ionic hairstyling polymer is selected from the group consisting of: polyvinylpyrrolidone/dimethylaminopropylaminoacrylates copolymer (Aquaflex^® SF 40 from ISP); isobutylene ethylmaleinimide/hydroxy

ethylmaleinimide copolymer (Aquaflex^® FX 64 from ISP);

vinylcaprolactam/polyvinylpyrrolidone/dimethylaminoethyl methacrylate copolymer (Advantage^® from ISP); and mixtures thereof. Non-ionic latex hairstyling polymers are also suitable. In at least one embodiment, the non-ionic hairstyling polymer is selected from the group consisting of: polyvinylpyrrolidone (K90, 85, 80, 60, 30), polyvinylpyrrolidone/vinyl acetate copolymers (PVPA/A 64), terpolymers of vinylpyrrolidone, methacrylamide and vinylimidazole (e.g. Luviset^® Clear from BASF), and mixtures thereof. In at least one embodiment, the non-ionic hairstyling polymer is selected from the group consisting of: PVP K 60, 30, and PVPA/A 37/64. In at least one embodiment, the non-ionic hairstyling polymer is selected from the group consisting of: PVP K60 and PVPA/A 37/64.

In at least one embodiment, the formulation comprises an anionic latex hairstyling polymer. In at least one embodiment, the anionic latex hairstyling polymer is a urethane-based polymer, for example polyurethane-34 (Baycusan^® from Bayer). Polyurethane-34 is described in EP-2105127A1. In at least one embodiment, the hairstyling polymer is the latex hairstyling polymer polyurethane-34.

In at least one embodiment, the anionic hairstyling polymer and/or cationic hairstyling polymer is present in neutralized or partially neutralized form. In at least one embodiment, the formulation comprises a neutralising agent, and wherein the neutralising agent is selected from the group consisting of: potassium hydroxide, sodium hydroxide, triisopropanolamine (TIPA), 2-aminobutanol, 2-aminomethyl propanol (AMP), aminoethylpropandiol, dimethyl stearamine (Armeen 18 D), sodium silicate, tetrahydroxypropyl ethylenediamine (Neutral^® TE), ammonia (NFb), triethanolamine, trimethylamine (Tris Amino Ultra), aminomethylpropandiol (AMPD) and mixtures thereof. In at least one embodiment, the neutralising agent is 2-aminomethyl propanol.

In at least one embodiment, the formulation has a viscosity of from 0 cPs to 20,000 cPs. In at least one embodiment, the formulation has a viscosity of from 0.1 cPs to 10,000 cPs, or from 1 cPs to 5,000 cPs, or from 5 cPs to 3,500 cPs.

The viscosity measurement conditions are defined in the definitions section above. Viscosity may be important for anti-drip reasons. Dripping can be inconvenient for the user. Furthermore, more viscous formulations can be useful for measured dispensing. In at least one embodiment, the formulation has a viscosity of from 0 cPs to 1 ,000 cPs. This viscosity range is advantageous when the formulation is in the form of a facial cleanser in view of the need for distribution on skin and ability to rinse off.

In at least one embodiment, the formulation further comprises a viscosity- modifying substance. The viscosity-modifying substance is preferably a thickening polymer.

In at least one embodiment, the thickening polymer is a polymers based on acrylamidomethylpropanesulfonic acid (AMPS^®, Lubrizol). These polymers, even at pH values of 7 or less, exhibit good thickening performance. Especially preferably, the the thickening polymer is selected from the group consisting of homo- or copolymers of acrylamidomethylpropanesulfonic acid and salts thereof. Among the polymers just mentioned, preference is in turn given to polymers having at least 20 mol-% of units based on acrylamidomethylpropanesulfonic acid and/or salts thereof, and particular preference to polymers having at least

50 mol-% of units based on acrylamidomethylpropanesulfonic acid and/or salts thereof, the mole figures relating in each case to the overall polymer. In the case of the copolymers, as well as structural units based on

acrylamidomethylpropanesulfonic acid and/or salts thereof, preferably one or more structural units based on the following comonomers are present in the copolymers: acrylic acid, methacrylic acid, acrylamide, dimethylacrylamide, vinylpyrrolidone (VP), hydroxyethyl acrylate, hydroxyethyl methacrylate, acrylic or methacrylic esters of ethoxylated alcohols R0-(CH2CH20)mH, in which R is an alkyl radical having 12 to 30 carbon atoms and m is a number from 3 to 30, and CH2 =

CH-COO-(CH2CH2-COO)_nX in which n is a number from 0 to 10 and X is a counterion and is preferably H⁺, Na⁺ and/or NH4⁺. The polymers selected from the group consisting of homo- or copolymers of acrylamidomethylpropanesulfonic acid and salts thereof may be crosslinked or uncrosslinked. In the case of crosslinking, they contain structural units based on monomers having 2 or more olefinic double bonds. In the case of crosslinking, preferably from 0.1 to 10 mol-% of such structural units are present in the homo- or copolymers, based on the overall polymer. If one or more structural units based on

acrylamidomethylpropanesulfonic acid and/or salts thereof in the homo- or copolymers of acrylamidomethylpropanesulfonic acid and/or salts thereof have one or more counterions other than H⁺, these other counterions are preferably selected from the group consisting of Na⁺ and NhV. Suitable polymers are mentioned in publications including EP-0816403, EP-1069142, EP-1 1 16733 and DE-10 2009 014877 (Clariant), EP-1347736 (L'Oreal) or EP-1496081 (Seppic). Examples include: Aristoflex^® AVC (Ammonium Acryloyldimethyltaurate/VP Copolymer), Aristoflex^® AVS (Sodium Acryloyldimethyltaurate/VP Crosspolymer), Aristoflex^® TAC (Ammonium Acryloyl Dimethyltaurate Carboxyethyl Acrylate Crosspolymer), Hostacerin^® AMP5 (Ammonium Polyacryloyldimethyl Taurate), Aristoflex^® HMB (Ammonium Acryloyldimethyltaurate/Beheneth-25 Methacrylate Crosspolymer), Aristoflex^® BLV (Ammonium Acryloyldimethyltaurate/Beheneth-25 Methacrylate Crosspolymer), Aristoflex^® HMS (Ammonium Acryloyldimethyl- taurate/Steareth-25 Methacrylate Crosspolymer), Aristoflex^® SNC (Ammonium Acryloyldimethyltaurate/Steareth-8 Methacrylate Copolymer), Aristoflex^® LNC (Ammonium Acryloyldimethyltaurate/Laureth-7 Methacrylate Copolymer) or Sepinov^® EMT 10 (Hydroxyethyl Acrylate/Sodium Acryloyldimethyl Taurate Copolymer), Sepigel^® 305.

In at least one embodiment, the thickening polymer selected from the group consisting of: copolymers of at least one first monomer type, which is chosen from acrylic acid and methacrylic acid, and at least one second monomer type, which is chosen from esters of acrylic acid and ethoxylated fatty alcohol; crosslinked polyacrylic acid; crosslinked copolymers of at least one first monomer type, which is chosen from acrylic acid and methacrylic acid, and at least one second monomer type, which is chosen from esters of acrylic acid with C10- to

C3o-alcohols; copolymers of at least one first monomer type, which is chosen from acrylic acid and methacrylic acid, and at least one second monomer type, which is chosen from esters of itaconic acid and ethoxylated fatty alcohol; copolymers of at least one first monomer type, which is chosen from acrylic acid and methacrylic acid, at least one second monomer type, which is chosen from esters of itaconic acid and ethoxylated C10- to C3o-alcohol and a third monomer type, chosen from C₁-to C4-aminoalkyl acrylates; copolymers of two or more monomers chosen from acrylic acid, methacrylic acid, acrylic esters and methacrylic esters; copolymers of vinylpyrrolidone and ammonium acryloyldimethyltaurate; copolymers of ammonium acryloyldimethyltaurate and monomers chosen from esters of methacrylic acid and ethoxylated fatty alcohols; hydroxyethylcellulose;

hydroxypropylcellulose; hydroxypropylguar; glyceryl polyacrylate; glyceryl polymethacrylate; copolymers of at least one C2-, C3- or C4-alkylene and styrene; polyurethanes; hydroxypropyl starch phosphate; polyacrylamide; copolymer of maleic anhydride and methyl vinyl ether crosslinked with decadiene; carob seed flour; guar gum; xanthan; dehydroxanthan; carrageenan; karaya gum; hydrolyzed corn starch; copolymers of polyethylene oxide, fatty alcohols and saturated methylenediphenyl diisocyanate (e.g. PEG-150/stearyl alcohol/SMDI copolymer); and mixtures thereof.

In at least one embodiment, the formulation has a pH value of from 2.0 to 12.0, preferably from 3.0 to 9.0, more preferably from 4.5 to 7.5. By varying the pH value, a formulation can be made available that is suitable for different

applications.

In at least one embodiment, the formulation comprises an alkalizing agent or pH adjusting agent. In at least one embodiment, ammonia or caustic soda is suitable, but water-soluble, physiologically tolerable salts of organic and inorganic bases can also be considered. Optionally, the pH adjusting agent is selected from ammonium hydrogen carbonate, ammonia, monoethanolamine, ammonium carbonate. In at least one embodiment, the alkalizing agents is selected from the group consisting of 2-amino-2-methyl-1 -propanol, 2-amino-2-methyl-1 ,3- propanediol, 2-amino-2-ethyl-1 ,3-propanediol, tris(hydroxyl-methyl)- aminomethane, 2-amino-1 -butanole, tris-(2-hydroxypropyl)-amine,

2,2-iminobisethanol, lysine, iminourea (guanidine carbonate), tetrahydro-1 ,4- oxazine, 2-amino-5-guanidin-valeric acid, 2-aminoethansulfonic acid,

diethanolamine, triethanolamine, N-methyl ethanolamine, isopropanolamine, diisopropanolamine, triisopropanolamine, glucamine, sodium hydroxide, potassium hydroxide, lithium hydroxide and magnesium oxide, and mixtures thereof. To establish an acidic pH value, and acid can be included. In at least one embodiment, the formulation comprises an acid selected from the group consisting of hydrochloric acid, phosphoric acid, acetic acid, formic acid, sulfuric acid, hydrochloric acid, citric acid, and mixtures thereof. Citric acid is most preferred in that it has high consumer acceptance. In at least one embodiment, the acidic pH is adjusted with a buffer such as a phosphate buffer, a TRIS buffer or a citric buffer. The buffers may be used alone or in combination with an acid.

In at least one embodiment, the formulation is in liquid form. In an alternative embodiment, the formulation is in solid form. Optionally, the formulation is in powdered or granulated form. This is advantageous in that it is not needed to ship liquid, which are typically heavy over long distances, which has economic and environmental benefits. A solid form can be achieved by spray drying the formulation or the employment of a rotary evaporator. The formulation can be converted into liquid form after it has been shipped e.g. by adding water.

In at least one embodiment, the composition is selected from the group consisting of shampoo, body wash, facial cleanser, face mask, bubble bath, intimate wash, bath oil, cleansing milk, micellar water, make-up remover, cleansing wipes, hair mask, perfume, liquid soap, shaving soap, shaving foam, cleansing foam, day cream, anti-ageing cream, body milk, body lotion, body mousse, face serum, eye cream, sunscreen lotion, sun cream, face cream, after-shave lotion, pre-shaving cream, depilatory cream, skin-whitening gel, self-tanning cream, anti-acne gel, mascara, foundation, primer, concealer, blush, bronzer, blemish balm (bb) cream, eyeliner, night cream, eye brow gel, highlighter, lip stain, hand sanitizer, hair oil, nail varnish remover, conditioner, hair styling gel, hair styling cream, anti-frizz serum, scalp treatment, hair colorant, split end fluid, deodorant, antiperspirant, baby cream, insect repellent, hand cream, sunscreen gel, foot cream, exfoliator, body scrub, cellulite treatment, bar soap, cuticle cream, lip balm, hair treatment, eye shadow, bath additive, body mist, eau de toilette, mouthwash, toothpaste, lubricating gel, moisturizer, serum, toner, aqua sorbet, cream gel, styling mousse, dry shampoo, lip stick, lip gloss, hydro-alcoholic gel, body oil, shower milk, illuminator, lip crayon, hair spray, combing cream, and sunblock. In at least one embodiment, the formulation is a household cleansing formulation.

In at least one embodiment, the formulation is a hand dishwashing formulation. In at least one embodiment, the hand dishwashing formulation comprises an anionic surfactant. In at least one embodiment, the hand dishwashing formulation comprises from 5 wt.-% to 25 wt.-% anionic surfactant. In at least one

embodiment, the hand dishwashing formulation comprises a surfactant system comprising at least one anionic surfactant and a further surfactant selected from non-ionic surfactants, amphoteric surfactants, or zwitterionic surfactants.

Preferably, the hand dishwashing formulation comprises cocoamidopropylbetaine or an amine oxide. Preferably the amine oxide is lauryl amine oxide, cocoyl amine oxide, or a combination thereof. In at least one embodiment, the pH value of the hand dishwashing formulation is between pH 5.0 and pH 10, preferably pH 5,5 to 9.0. In the case of the hand dishwashing formulation comprising an amine oxide, the hand dishwashing formulation preferably has a pH of between pH 7.5 and pH 9.5, most preferably pH 8.0 and pH 9.0.

In at least one embodiment, the formulation is a hard surface cleaner. In at least one embodiment, the hard surface cleaner comprises an anionic surfactant. In at least one embodiment, the hard surface cleaner comprises from 1 wt.-% to 10 wt.-% anionic surfactant. In at least one embodiment, the hard surface cleaner comprises a nonionic surfactant. In at least one embodiment, the hard surface cleaner comprises from 1 wt.-% to 10 wt.-% nonionic surfactant. In at least one embodiment, the hard surface cleaner comprises a surfactant system comprising at least one anionic surfactant and a further surfactant selected from non-ionic surfactants, amphoteric surfactants, and zwitterionic surfactants, or combinations thereof. Preferably, the hard surface cleaner comprises linear

alkylbenzenesulfonate and fatty alcohol ethoxylate. In at least one embodiment, the pH value of the hard surface cleaner is between pH 5.0 and pH 11 , preferably from pH 6.0 to pH 9.0. In at least one embodiment, the formulation is a liquid laundry detergent formulation comprising one or more surfactants. Preferably, the one or more surfactants of the liquid laundry detergent formulation are selected from the group consisting of anionic, nonionic, cationic and zwitterionic surfactants, and more preferably from the group consisting of anionic, nonionic and zwitterionic surfactants.

Anionic Surfactants

In at least one embodiment, the formulation comprises an anionic surfactant.

Anionic surfactants are particularly useful in cleansing formulations such as household cleansing formulations. Preferred anionic surfactants are alkyl sulfonates and alkyl ether sulfates.

Preferred alkyl sulfonates are alkylbenzene sulfonates, particularly linear alkylbenzene sulfonates (LAS) having an alkyl chain length of C8-C15. Possible counterions for concentrated alkaline liquids are ammonium ions, e.g. those generated by the neutralization of alkylbenzene sulfonic acid with one or more ethanolamines, for example monoethanolamine (MEA) and triethanolamine (TEA), or alternatively, alkali metals, e.g. those arising from the neutralization of alkylbenzene sulfonic acid with alkali hydroxides. The linear alkyl benzene sulfonate surfactants may be LAS with an alkyl chain length of preferably from 8 to 15 and more preferably from 12 to 14. Preferred alkyl ether sulfates (AES) are alkyl polyethoxylate sulfate anionic surfactants.

Nonionic Surfactants

In at least one embodiment, the formulation comprises a nonionic surfactant.

Nonionic surfactants include primary and secondary alcohol ethoxylates, especially C8-C20 aliphatic alcohol ethoxylated with an average of from 1 to 20 moles of ethylene oxide per mole of alcohol, and more especially the C10-C15 primary and secondary aliphatic alcohols ethoxylated with an average of from 1 to 10 moles of ethylene oxide per mole of alcohol. Non-ethoxylated nonionic surfactants include alkyl polyglycosides, glycerol monoethers and polyhydroxy amides (glucamide). Mixtures of nonionic surfactants may be used. When included therein, the household cleansing formulation, particularly the liquid laundry detergent formulation, preferably comprises from 0.2 wt.-% to 40 wt. %, more preferably 1 wt.-% to 20 wt.-% nonionic surfactant, such as alcohol ethoxylate, nonylphenol ethoxylate, alkylpolyglycoside, alkyldimethylamineoxide, ethoxylated fatty acid monoethanolamide, fatty acid monoethanolamide, polyhydroxy alkyl fatty acid amide, N-acyl N-alkyl derivatives of glucosamine ("glucamides"), or combinations thereof. The nonionic surfactants that may be used include the primary and secondary alcohol ethoxylates, especially the C8-C20 aliphatic alcohols ethoxylated with an average of from 1 to 35 moles of ethylene oxide per mole of alcohol, and more especially the C10-C15 primary and secondary aliphatic alcohols ethoxylated with an average of from 1 to 10 moles of ethylene oxide per mole of alcohol.

Zwitterionic Surfactants

In at least one embodiment, the formulation comprises a zwitterionic surfactant. The liquid laundry detergent formulation may comprise a zwitterionic surfactant, e.g. amine oxide or betaine, preferably in an amount of up to 10 wt.-% based on the total weight of the liquid laundry detergent formulation.

Betaines may be alkyldimethyl betaines or alkylamido betaines, wherein the alkyl groups have C12-18 chains.

Additional Surfactants

In at least one embodiment, the liquid laundry detergent formulation comprises a surfactant selected from the group consisting of anionic surfactants, nonionic surfactants, and mixtures thereof; preferably the surfactant is selected from the group consisting of linear alkyl benzene sulfonates, alkyl ether sulfates, nonionic surfactants, amine oxides and betaines; and more preferably selected from the group consisting of linear alkyl benzene sulfonates, alkyl ether sulfates and nonionic surfactants. Other surfactants than the preferred LAS, AES, and nonionic surfactants may be added to the formulation according to the sixth aspect.

Although less preferred, some alkyl sulfate surfactant may be used, especially the non-ethoxylated C12-15 primary and secondary alkyl sulfates. Soap may also be used. Levels of soap are preferably lower than 10 wt.-%.

Preferably, the one or more surfactants in the liquid laundry detergent

formulations, are present in an amount of at least 5 wt.-%, more preferably from 5 wt.-% to 65 wt.-%, even more preferably from 6 to 60 wt.-% and extraordinarily preferably from 7 wt.-% to 55 wt.-%, in each case based on the total weight of the liquid laundry detergent formulation.

Further Optional Ingredients

The household cleansing formulations may comprise one or more optional ingredients, e.g. they may comprise conventional ingredients commonly used in detergent compositions, especially laundry detergent compositions. Examples of optional ingredients include, but are not limited to builders, bleaching agents, bleach active compounds, bleach activators, bleach catalysts, photobleaches, dye transfer inhibitors, colour protection agents, anti-redeposition agents, dispersing agents, fabric softening and antistatic agents, fluorescent whitening agents, enzymes, enzyme stabilizing agents, foam regulators, defoamers, malodour reducers, preservatives, disinfecting agents, hydrotropes, fibre lubricants, anti- shrinkage agents, buffers, fragrances, processing aids, colorants, dyes, pigments, anti-corrosion agents, fillers, stabilizers and other conventional ingredients for washing or laundry detergent compositions.

Polymer

For detergency boosting, it may be advantageous to use a polymer in the household cleansing formulations, particularly in the liquid laundry detergent formulations. This polymer is preferably a polyalkoxylated polyethyleneimine (EPEI). Polyethylene imines are materials composed of ethylene imine units -CH2CH2NH- and, where branched, the hydrogen on the nitrogen is replaced by another chain of ethylene imine units. These polyethyleneimines can be prepared, for example, by polymerizing ethyleneimine in the presence of a catalyst such as carbon dioxide, sodium bisulfite, sulfuric acid, hydrogen peroxide, hydrochloric acid, acetic acid, and the like. Specific methods for preparing these polyamine backbones are disclosed in US 2,182,306, US 3,033,746, US 2,208,095,

US 2,806,839, and US 2,553,696.

The household cleansing formulations, particularly the liquid laundry detergent formulations, may comprise other polymeric materials, for example: dye transfer inhibition polymers, anti-redeposition polymers and cotton soil release polymers, especially those based on modified cellulosic materials. Especially, when EPEI is not present, the formulation may further comprise a polymer of polyethylene glycol and vinyl acetate, for example the lightly grafted copolymers described in

WO 2007/138054. Such amphiphilic graft polymers based on water soluble polyalkylene oxides as graft base and side chains formed by polymerisation of a vinyl ester component have the ability to enable reduction of surfactant levels whilst maintaining high levels of oily soil removal.

Hydrotropes

In at least one embodiment, the formulation comprises a hydrotrope. Herein “hydrotrope” is a solvent that is neither water nor conventional surfactant, and that aids the solubilisation of surfactants and other components, especially any polymer and/or sequestrant, in the liquid, to render it isotropic. Hydrotropes are particularly useful in household cleansing formulations. Among suitable

hydrotropes the following are noteworthy: monopropylene glycol (MPG), glycerol, sodium cumene sulfonate, ethanol, other glycols, e.g. dipropylene glycol, diethers and urea. MPG and glycerol are preferred hydrotropes.

Enzymes

In at least one embodiment, the formulation, particularly the liquid laundry detergent formulation, comprises an enzyme. In at least one embodiment, the enyzme is selected from the group consisting of protease, mannanase, pectate lyase, cutinase, esterase, lipase, amylase, cellulase, and combinations thereof. Less preferred additional enzymes may be selected from peroxidase and oxidase. The enzymes are preferably present with corresponding enzyme stabilizers. The total enzyme content in the formulation is preferably from 0 wt. % to 5 wt.-%, more preferably from 0.5 wt.-% to 5 wt.-% and even more preferably from 1 wt.-% to 4 wt.-%, by total weight of the formulation.

Sequestrants

Sequestrants are preferably included in the formulation, particularly in the household cleansing formulations. Preferred sequestrants include organic phosphonates, alkanehydroxy phosphonates and carboxylates available under the DEQUEST trade mark from Thermphos. The preferred sequestrant level is less than 10 wt.-% and preferably less than 5 wt.-% by total weight of the formulation.

A particularly preferred sequestrant is HEDP (1 -hydroxyethylidene-1 ,1 - diphosphonic acid), for example sold as Dequest 2010. Also suitable but less preferred as it gives inferior cleaning results is Dequest^® 2066 (diethylenetriamine penta(methylene-phosphonic acid) or Heptasodium DTPMP).

Buffers

In at least one embodiment, the formulation, particularly the liquid laundry detergent formulation, comprises a buffer. In addition to agents optionally included for the generation of anionic surfactants, e.g. from LAS or fatty acids, the presence of buffer is preferred for pH control. Possible buffers are one or more

ethanolamines, e.g. monoethanolamine (MEA) or triethanolamine (TEA). They are preferably used in formulation at levels of from 1.0 to 15 wt.-%. Other suitable amino alcohol buffer materials may be selected from the group consisting of compounds having a molecular weight above 61 g/mol, which includes MEA. Suitable materials also include, in addition to the already mentioned materials: monoisopropanolamine, diisopropanolamine, triisopropanolamine, monoamino hexanol, 2-[(2-methoxyethyl) methylamino]-ethanol, propanolamine,

N methylethanolamine, diethanolamine, monobutanolamine, isobutanolamine, monopentanolamine, 1 -amino-3-(2-methoxyethoxy)-2-propanol, 2-methyl-4- (methylamino)-2-butanol and mixtures thereof. Potential alternatives to amino ethanol buffers are alkali hydroxides such as sodium hydroxide or potassium hydroxide.

EXAMPLES

The examples which follow are intended to illustrate the subject matter of the invention without restricting it thereto.

Synthesis examples of the compound X of the first aspect:

Synthesis example 1 : Preparation of N-decenoyl-N-methyl-glucamine:

In a 500 mL glass flask (equipped with stirrer, dropping funnel, water separator, nitrogen line and vacuum line) 649.0 g of a ca. 42 % aqueous solution of

N-methyl-glucamine (1.40 mol) are placed. While stirring, this solution is heated up to 135 °C to evaporate water. Then 30 mbar vacuum is applied for 1 h at 135 °C and then vacuum is broken with nitrogen. Afterwards 53.8 g of propylene glycol are added. 252.8 g (1.42 mol) of tempered decenoic acid methylester (120 °C) is added slowly to the hot melt of N-Methyl-Glucamine to avoid foaming. Then 5.59 g sodium methoxide are added. Meanwhile the temperature of the reaction mixture reached 110°C and methanol is distilling off. After half an hour, vacuum is applied step by step to gain 30 mbar finally. Temperature is hold at 90 - 100°C and also vacuum is hold at 30 mbar for 90 min. Then vacuum is broken with nitrogen. The hot mixture is filled in a suitable glass bottle. You get 528 g of a slightly yellowish and highly viscous paste. The resultant product contains 76 % of the desired N-decenoyl-N-methyl-glucamine measured by GC after derivatisation.

Synthesis example 2: The steps as per synthesis example 1 are followed except that the (1.43 mol) of tempered decenoic acid methylester is replaced with

1.43 mol of tempered dodecenoic acid methylester (120 °C). The resultant product contains 77 % of N-dodecenoyl-N-methyl glucamine measured by GC after derivatisation. Synthesis example 3: The steps as per synthesis example 1 are followed except that the (1.43 mol) of tempered decenoic acid methylester is replaced with

1.43 mol of a mixture of tempered (120 °C) 9,12-tridecadienic acid methylester and 9,12-pentadecadienic acid methylester. The resultant product contains 82 % of a mixture of the desired glucamide measured by GC after derivatisation.

Table 1 : Example compositions of the first aspect

KEY:

* = compound according to Formula (I), wherein R derives from a 9-decenoic acid;

^# = compound according to Formula (I), wherein R derives from a 9-dodecenoic acid;

^** = compound according to Formula (I), wherein R derives from a mixture of 9,12-tridecadienic acid and 9,12-pentadecadienic acid. 3

o m

4

n

H

e¾ bo o o

Table 3: Example formulations of the sixth aspect

KEY:

¹ = see Table 2 above;

² = see Table 1 above;

ND = not determined.

Table 3: Example formulations of the sixth aspect (continued)

KEY:

¹ = see Table 2 above;

² = see Table 1 above;

§ = hand dishwashing formulation.

Table 3: Example formulations of the sixth aspect (continued)

KEY:

¹ = see Table 2 above;

² = see Table 1 above,

ND = not determined.

Table 3: Example formulations of the sixth aspect (continued)

KEY:

¹ = see Table 2 above;

² = see Table 1 above;

§ = hard surface cleaner

Table 3: Example formulations of the sixth aspect (continued)

KEY:

1 = see Table 2 above;

² = see Table 1 above;

& = liquid laundry detergent formulation Table 3: Example formulations of the sixth aspect (continued)

KEY:

¹ = see Table 2 above;

² = see Table 1 above; Example methods of use of the formulations:

Example 1 in Table 3 is a shampoo formulation. Shampoo formulations of the present invention are used in a conventional manner for cleaning and conditioning hair or skin. For example, an effective amount of the composition for cleansing and conditioning the hair or skin is applied to the hair or skin, which has preferably already been wetted with water, and then rinsed off. Such effective amounts generally range from about 1 gram to about 50 gram, preferably from about 1 gram to about 20 gram. Application to the hair typically includes working the composition through the hair such that most or all of the hair is contacted with the composition. For example, for cleansing and conditioning the hair or skin comprises the steps of: a) wetting the hair or skin with water, b) applying an effective amount of the shampoo composition to the hair or skin, and c) rinsing the applied areas of skin or hair with water. These steps can be repeated as many times as desired to achieve the desired cleansing and/or conditioning benefit.

EXPERIMENTAL

For testing the inhibition of bacteria, Composition 1 from Table 1 above was diluted in butylpolyglycol and added in different concentrations to liquid Caso-Agar at 50 °C and is buffered to pH 7 (+/- 0.2). For testing the inhibition of yeast and mold, Composition 1 was diluted in butylpolyglycol and added in different concentrations to liquid Sabouraud-4 % Dextrose-Agar at 50 °C and is buffered to pH 5.6 (+/- 0.2). Each of the solutions is poured into a petri-dish and inoculated with the same amount of bacteria, yeast or mold respectively. The minimum inhibitory concentration (MIC) is the lowest concentration of Composition 1 that inhibits the growth of the respective microorganism where the next lowest dilution fails to inhibit the growth of said microorganism.

The experiments were carried out in scientifically fair conditions so that a proper comparison can be made and conclusions drawn.

Table 4: Table of MIC data:

Conclusions:

The data shows Composition Ts activity against a broad range of microorganisms. The MIC values are very strong against Staph, aureus, and Klebsiella pneumonia. Composition 1 is especially strong against fungi, while against some gram- negative bacteria no efficacy is found. The comparison shows a similar profile as the MIC found for Sorbitan Caprylate, both substance show efficacy against the same organisms and a gap in efficacy against the same organisms as well. The structure of Composition 1 is chemically more stable than comparable market standards (sorbitan caprylate, glyceryl caprylate) versus high/low pH as the amide bond is more stable than an ester bond. This enables use in broader range of formulations across the application areas, without compromising on performance. The increased water solubility of Composition 1 is a feature, which is not found in the comparable market standards. This is highly appreciated by formulators, because it makes formulating the ingredient easier in all types of formulations containing water. Composition 1 is less likely to precipitate/cream in the respective formulation, contributing not only to microbiological stability, but also ensures formulation stability.

The Compound X has a relatively high Hydrophilic Lipophilic Balance HLB value (Compound X = HLB of 10.5) and this allows its use as a non-ionic surfactant in rinse-off formulations, as non-ionic emulsifier in emulsions and as a solubiliser for additives in all kinds of formulations.

Claims

Patent claims What is claimed is:

1. A composition for inhibiting micro-organisms wherein the composition comprises at least 30 wt.-% compound X, wherein compound X is according to Formula (I):

2. The composition according to claim 1 , wherein the composition is an aqueous solution.

3. The composition according to any of the preceding claims, wherein the composition comprises at least 40 wt.-%, preferably at least 50 wt.-%, more preferably at least 60 wt.-%, even more preferably 70 wt.-% compound X.

4. The composition according to any of the preceding claims, wherein the composition is a pumpable liquid.

5. The composition according to any of the preceding claims, wherein the viscosity of the composition is from 1 mPa.s to 20,000 mPa.s.

6. The composition according to any of the preceding claims, wherein R is an unsaturated hydrocarbon chain having seven, nine or eleven carbon atoms, or a combination thereof; preferably R is a linear, unsaturated hydrocarbon chain having seven, nine or eleven carbon atoms, or a combination thereof.

7. The composition according to any of the preceding claims, wherein the composition comprises a solvent selected from the group consisting of water, glycols, ethanol, and combinations thereof.

8. The composition according to any of the preceding claims, wherein R is

H₂C=CH-(CH₂)7-.

9. The composition according to any of the preceding claims, wherein R¹ is -H, or is C1 to C6 alkyl, more preferably C1 to C4 alkyl, much more preferably C1 or C2 (methyl or ethyl); most preferably R¹ is methyl.

10. A preservative concentrate comprising:

compound X, wherein the compound X is according to Formula (I):

wherein R is an unsaturated hydrocarbon chain having 5 to 13 carbon atoms; and wherein R¹ is -H or a C1-6 unsubstituted alkyl moiety, preferably R¹ is methyl; and

an anti-microbial active.

11. The concentrate according to claim 10, wherein the weight ratio of the compound X to the anti-microbial active is from 1 :9 to 9:1.

12. The concentrate according to any of claims 10 to 11 , wherein the

antimicrobial active is a preservative, wherein the preservative is selected from the group consisting of aromatic alcohols, organic acids and salts thereof,

hydroxypyridones, alkyl diols, halogenated compounds, isothiazolinones and combinations thereof.

13. Use of a compound X as a preservative booster or as an antimicrobial agent, wherein compound X is according to Formula (I):

wherein R is an unsaturated hydrocarbon chain having 5 to 13 carbon atoms; and wherein R¹ is -H or a C1-6 unsubstituted alkyl moiety, preferably R¹ is methyl.

14. The use according to claim 13, wherein compound X is a mixture of compounds according to Formula (I) wherein R is H2C=CH-(CH2)7-.

15. A method of reducing the effects of micro-organisms, wherein the method comprises adding the composition according to any of claims 1 to 8 to an anti- microbial active to form a formulation.