Laundry composition

Abstract

A fabric conditioner composition comprising from 1 to 30 wt.% ester-linked quaternary ammonium compound; from 0.01 to 5wt.% glycerol ester alkoxylate, from 0.1 to 20 wt.% perfume and having a viscosity of at least 100mPa.s when measured using a cone and plate rheometer.

Description

[0001] LAUNDRY COMPOSITION

[0002] Field of the Invention

[0003] The present invention relates to fabric conditioner compositions.

[0004] Background of the Invention

[0005] Fabric conditioner compositions deliver multiple benefits to fabrics in the rinse stage of the laundry process, for example by imparting softness or fragrance to the fabric surface.

[0006] Some fabric conditioners comprise a rheology modifier, usually to manipulate the pouring viscosity.

[0007] A common drawback of typical fabric conditioner compositions is that they tend to cause the fabric surface to become hydrophobic. This is exacerbated over multiple washes as more and more softener molecules build up, thus leading to an increasingly hydrophobic surface. The effect of this increased hydrophobicity is such that the water absorbency of said fabrics is reduced. This is a problem for fabrics used in many applications where the need to remove water from someone’s skin is important, for example a towel.

[0008] Despite the prior art there exists a need for improved fabric conditioner compositions which result in less of a detriment to a fabric’s water absorbing capacity when used in a typical laundry process, whilst simultaneously maintaining an acceptable viscosity.

[0009] Summary of the Invention

[0010] The inventors have surprisingly found that by including a specific glycerol ester alkoxylate a fabric conditioning composition can be provided which causes less of a detrimental effect on the water absorbency of fabrics treated with said composition, whilst simultaneously achieving a viscosity preferred by consumers.

[0011] Accordingly in a first aspect of the present invention is provided a fabric conditioner composition comprising: a. 1 to 30 wt.% ester-linked quaternary ammonium compound; b. 0.01 to 5wt.% glycerol ester alkoxylate; and c. 0.1 to 20 wt.% perfume, wherein the glycerol ester alkoxylate is selected from substances of the following formula (I): wherein R1, R2and R3are, independent from each other, selected from linear or branched alkylene groups (CmH2m) with m being 2 or 3 or mixtures thereof; x, y and z are, independent from each other, integer numbers from 0 to 300, where at least one of the variables x, y and z is 1 or an integer number greater than 1 , preferably are, independent from each other, integer numbers from 1 to 250, more preferably from 2 to 200, even more preferably from 5 to 150, particularly preferably from 10 to 120, extraordinarily preferably from 15 to 110 and especially preferably from 20 to 100;

[0012] R4, R5and R6are, independent from each other, selected from hydrogen, linear or branched, preferably linear, saturated or unsaturated acyl groups comprising from 8 to 30 carbon atoms or mixtures thereof, preferably are, independent from each other, selected from hydrogen, linear or branched, preferably linear, saturated or unsaturated acyl groups comprising from 12 to 30 carbon atoms or mixtures thereof, more preferably are, independent from each other, selected from hydrogen, linear or branched, preferably linear, saturated or unsaturated acyl groups comprising from 12 to 24 carbon atoms or mixtures thereof, even more preferably are, independent from each other, selected from hydrogen, linear or branched, preferably linear, saturated or unsaturated acyl groups comprising from 12 to 20 carbon atoms or mixtures thereof, and particularly preferably are, independent from each other, selected from hydrogen, linear or branched, preferably linear, saturated or unsaturated acyl groups comprising from 14 to 20 carbon atoms or mixtures thereof, and wherein in the definitions of R4, R5and R6above, at least one of R4, R5and R6is an acyl groups; characterized in that x+y+z is, based on a molar average, a number from 50 to 300, preferably from 60 to 300, more preferably from 70 to 280, even more preferably from 85 to 250 and particularly preferably from 90 to 250; at least 70 mol%, preferably at least 75 mol%, more preferably at least 80 mol% and even more preferably at least 85 mol% of the glycerol ester alkoxylates of the formula (I) in the mixture, in each case based on the total amount of the glycerol ester alkoxylates of the formula (I) in the mixture, are glycerol ester alkoxylates of the formula (I), wherein all of the groups R4, R5and R6are acyl groups; and at least 30 mol%, preferably at least 40 mol%, more preferably at least 50 mol%, even more preferably at least 60 mol% and particularly preferably at least 70 mol% of those groups R4, R5and R6, , are linear or branched, preferably linear, saturated or unsaturated acyl groups comprising 16 to 20 carbon atoms or mixtures thereof and preferably are linear or branched, preferably linear, saturated or unsaturated acyl groups comprising 16 to 18 carbon atoms or mixtures thereof, in each case based on the total amount of the linear or branched, preferably linear, saturated or unsaturated acyl groups R4, R5and R6, and wherein the viscosity of the composition is at least 100mPa.s when measured at a shear rate of 20s_1at 20°C using a cone and plate rheometer with a 2 degree cone angle.

[0013] In a second aspect is provided a method of manufacturing a fabric conditioner composition according to the first aspect, wherein the glycerol ester alkoxylate is added sequentially after the free oil perfume.

[0014] In a third aspect, the present invention provides a method of treating fabrics with a fabric conditioning composition, wherein a fabric conditioner as described herein is delivered to the fabric in the rinse stage of a laundry process.

[0015] In a further aspect is provided a use of a fabric conditioner as described herein to provide conditioning to a fabric surface whilst simultaneously not compromising said fabric’s wettability, wherein a composition as described herein is delivered to the fabric in the rinse stage of a laundry process. Detailed Description of the Invention

[0016] These and other aspects, features and advantages will become apparent to those of ordinary skill in the art from a reading of the following detailed description and the appended claims. For the avoidance of doubt, any feature of one aspect of the present invention may be utilised in any other aspect of the invention. The word “comprising” is intended to mean “including” but not necessarily “consisting of” or “composed of.” In other words, the listed steps or options need not be exhaustive. It is noted that the examples given in the description below are intended to clarify the invention and are not intended to limit the invention to those examples per se. Similarly, all percentages are weight / weight percentages unless otherwise indicated. Except in the operating and comparative examples, or where otherwise explicitly indicated, all numbers in this description indicating amounts of material or conditions of reaction, physical properties of materials and / or use are to be understood as modified by the word “about”. Numerical ranges expressed in the format "from x to y" are understood to include x and y. When for a specific feature multiple preferred ranges are described in the format "from x to y", it is understood that all ranges combining the different endpoints are also contemplated.

[0017] Ester-linked quaternary ammonium compound

[0018] The compositions described herein comprise 1 to 30 wt.% ester-linked quaternary ammonium compound. Preferably the compositions comprise 1.5 to 20 wt.% ester-linked quaternary ammonium compound, most preferably 2 to 15 wt.% ester-linked quaternary ammonium compound by weight of the composition.

[0019] The ester linked quaternary ammonium compound preferably comprises at least one chain derived from fatty acids, more preferably at least two chains derived from a fatty acid. Preferably the fatty acids are defined as aliphatic monocarboxylic acids having a chain of 4 to 28 carbons. Fatty acids may be derived from various sources such as tallow or plant sources (e.g. palm oil). Preferably the fatty acid chains are derived from plants. Preferably the fatty acid chains of the ester linked quaternary ammonium compound comprise from 10 to 50 wt. % of saturated C18 chains and from 5 to 40 wt. % of monounsaturated C18 chains by weight of total fatty acid chains. In a further preferred embodiment, the fatty acid chains of the ester linked quaternary ammonium compound comprise from 20 to 40 wt. %, preferably from 25 to 35 wt. % of saturated C18 chains and from 10 to 35 wt. %, preferably from 15 to 30 wt. % of monounsaturated C18 chains, by weight of total fatty acid chains.

[0020] Particularly preferred materials are ester-linked triethanolamine (TEA) quaternary ammonium compounds comprising a mixture of mono-, di- and tri-ester linked components. A first group of ester linked quaternary ammonium compounds suitable for use in compositions described herein are represented by formula (I): wherein each R is independently selected from a C5 to C35 alkyl or alkenyl group; R1represents a C1 to C4 alkyl, C2 to C4 alkenyl or a C1 to C4 hydroxyalkyl group; T may be either O-CO. (i.e. an ester group bound to R via its carbon atom), or may alternatively be CO-O (i.e. an ester group bound to R via its oxygen atom); n is a number selected from 1 to 4; m is a number selected from 1, 2, or 3; and X- is an anionic counter-ion, such as a halide or alkyl sulphate, e.g. chloride or methylsulfate. Di-esters variants of formula I (i.e., m = 2) are preferred and typically have mono- and tri-ester analogues associated with them. Such materials are particularly suitable for use in the present invention.

[0021] A second group of ester linked quaternary ammonium compounds suitable for use in the compositions described herein are represented by formula (II):

[0022] (R^NHCH -CH-TR^ X- (II) wherein each R1group is independently selected from C1 to C4 alkyl, hydroxyalkyl or C2 to C4 alkenyl groups; and wherein each R2group is independently selected from C8 to C28 alkyl or alkenyl groups; and wherein n, T, and X- are as defined above.

[0023] Preferred materials of this second group include 1,2 bis[tallowoyloxy]-3- trimethylammonium propane chloride, 1 ,2 bis[hardened tallowoyloxy]-3- trimethylammonium propane chloride, 1 ,2- bis[oleoyloxy]-3-trimethylammonium propane chloride, and 1,2 bis[stearoyloxy]-3- trimethylammonium propane chloride. Such materials are described in US 4, 137,180 (Lever Brothers). Preferably, these materials also comprise an amount of the corresponding monoester.

[0024] A third group of ester linked quaternary ammonium compounds suitable for use in the compositions described herein are represented by formula (III): wherein each R1group is independently selected from C1 to C4 alkyl, or C2 to C4 alkenyl groups; and wherein each R2group is independently selected from C8 to C28 alkyl or alkenyl groups; and n, T, and X- are as defined above. Preferred materials of this third group include bis(2-tallowoyloxyethyl)dimethyl ammonium chloride, partially hardened and hardened versions thereof.

[0025] A fourth group of ester linked quaternary ammonium compounds are represented the by the formula (IV):

[0026] A fifth group of ester linked quaternary ammonium compounds suitable for use in the invention are represented by formula (V)

[0027] Ri and R2 are independently selected from C10 to C22 alkyl or alkenyl groups, preferably C14 to C20 alkyl or alkenyl groups. X- is as defined above.

[0028] A sixth group of ester linked quaternary ammonium compounds suitable for use in the present compositions are compounds obtained by reacting: i) a mixture of at least one dicarboxylic acid of formula (VI)

[0029] Formula (VI) wherein X represents a saturated or unsaturated hydrocarbon residue having 1 to 8 carbon atoms, and at least one monocarboxylic acid of formula (VII) Formula (VII) wherein R1 represents a saturated or unsaturated hydrocarbon residue having 5 to 21 carbon atoms, with ii) at least one tertiary amine of formula (VIII) Formula (VIII) wherein R2, R3, and R4independently represent a C2 to Ce hydroxyalkyl group, preferably 2-hydroxyethyl, and then reacting the resulting product with iii) at least one quaternizing agent for quaternizing at least one amino group contained in the reaction product.

[0030] In the dicarboxylic acid of formula (VI), X preferably represents a group having 2 to 8 carbons, X preferably represents a hydroxy-substituted linear or branched alkyl or alkylene. More preferably, X represents ethan-1 ,2-diyl, propan-1 , 2-diyl, propan-1 , 3-diyl, butan-1 ,4-diyl, hexan- 1 ,4-diyl, or cyclohexan-1 ,4-diyl, particularly preferably X represents butan-1 , 4-diyl. Even more preferably the dicarboxylic acid is selected from: succinic acid, maleic acid, glutaric acid, adipic acid and combinations thereof. Most preferably the dicarboxylic acid comprises adipic acid.

[0031] In the monocarboxylic acids of formula (VII), R1CO preferably represents an aliphatic, linear, or branched acyl residue having 6 to 22 carbon atoms. Preferably the monocarboxylic acid is selected from caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselic acid, linoleic acid, linolenic acid, 2-octyldodecanoic acid, eleostearic acid, arachidic acid, gadoleic acid, behenic acid, erucic acid, coconut fatty acid, palm fatty acid, palm kernel fatty acid, tallow fatty acid and combinations thereof. Industrial mixtures thereof which are produced, for example, during the pressurized cleavage of natural fats and oils, during the reduction of aldehydes from the Roelen oxo synthesis, or the dimerization of unsaturated fatty acids may also be used. More preferably the monocarboxylic acid is selected from: Stearic acid, isostearic acid, palmitic acid, myristic acid, lauric acid, capric acid, caprylic acid, 2-ethylhexanoic acid, 2-octyldodecanoic acid, caproic acid, oleic acid, linoleic acid, and linolenic acid, coconut fatty acid, palm fatty acid, palm kernel fatty acid, tallow fatty acid and combinations thereof.

[0032] Preferably the dicarboxylic acid of formula (VI) is selected from: succinic acid, maleic acid, glutaric acid, adipic acid, and combinations thereof and the monocarboxylic acid of formula (II) is selected from: stearic acid, isostearic acid, palmitic acid, myristic acid, lauric acid, capric acid, caprylic acid, 2-ethylhexanoic acid, 2-octyldodecanoic acid, caproic acid, oleic acid, linoleic acid, linolenic acid, partially-hydrogenated coconut fatty acid, palm fatty acid, palm kernel fatty acid, tallow fatty acid and combinations thereof.

[0033] The alkanolamines of formula (VIII), preferably contain a hydroxyalkane residue (alkanol residue) having 2 to 6 carbon atoms, preferably 2 to 4 carbon atoms. Preferably the alkanolamines of formula (III) comprises triethanolamine.

[0034] The monocarboxylic acids (of formula VII) and the dicarboxylic acids (of formula VI) may be used in the molar ratio of from about 1 :10 to about 10:1. It has, however, proven advantageous to use a molar ratio of from about 1 :1 to about 4:1 and, in particular, from about 1.5:1 to about 3:1.

[0035] In an especially preferred embodiment of the sixth type of ester linked quaternary ammonium compounds, is an esterquat compound of formula (IX) wherein,

[0036] X is a saturated or unsaturated hydrocarbon residue having 1 to 10 carbon atoms preferably butan-1 ,4-diyl

[0037] A is a (C2 to C6) alkanediyl group, preferably ethan-1 ,2-diyl R1 is a (C2 to C4) hydroxyalkyl group or a (C6 to C22) acyloxy (C2 to C4) alkyl group, preferably 2-hydroxyethyl or 2-((C6 to C22) acyloxy)ethyl;

[0038] R2 is methyl or ethyl;

[0039] R3 and R4-independently are a hydrogen atom or a (C6 to C2) acyl group; n is 1 or 2; and

[0040] Z- is an anion, preferably methyl sulphate;

[0041] And wherein, at least one of the groups R1 , R3, or R4 comprises a (C6 to C22) acyl residue.

[0042] Glycerol ester alkoxylate

[0043] The composition defined herein comprises from 0.01 to 5wt.% glycerol ester alkoxylate by weight of the composition. Preferably the compositions comprise 0.05 to 4wt.% glycerol ester alkoxylate, more preferably 0.1 to 3wt% glycerol ester alkoxylate, more preferably 0.2 to 2wt% and most preferably 0.3 to 1wt% glycerol ester alkoxylate by weight of the composition.

[0044] Glycerol ester alkoxylates according to the invention are molecules according to the following formula(l):

[0045] Wherein,

[0046] R1, R2and R3are, independent from each other, selected from linear or branched alkylene groups (CmH2m) with m being 2 or 3 or mixtures thereof; x, y and z are independent from each other, integer numbers from 0 to 300, where at least one of the variables x, y and z is 1 or an integer number greater than 1 , preferably are, independent from each other, integer numbers from 1 to 250, more preferably from 2 to 200, even more preferably from 5 to 150, particularly preferably from 10 to 120, extraordinarily preferably from 15 to 110 and especially preferably from 20 to 100; R4, R5and R6are, independent from each other, selected from hydrogen, linear or branched, preferably linear, saturated or unsaturated acyl groups comprising from 8 to 30 carbon atoms or mixtures thereof, preferably are, independent from each other, selected from hydrogen, linear or branched, preferably linear, saturated or unsaturated acyl groups comprising from 12 to 30 carbon atoms or mixtures thereof, more preferably are, independent from each other, selected from hydrogen, linear or branched, preferably linear, saturated or unsaturated acyl groups comprising from 12 to 24 carbon atoms or mixtures thereof, even more preferably are, independent from each other, selected from hydrogen, linear or branched, preferably linear, saturated or unsaturated acyl groups comprising from 12 to 20 carbon atoms or mixtures thereof, and particularly preferably are, independent from each other, selected from hydrogen, linear or branched, preferably linear, saturated or unsaturated acyl groups comprising from 14 to 20 carbon atoms or mixtures thereof, and wherein in the definitions of R4, R5and R6above, at least one of R4, R5and R6is an acyl group; characterized in that x+y+z is, based on a molar average, a number from 50 to 300, preferably from 60 to 300, more preferably from 70 to 280, even more preferably from 85 to 250 and particularly preferably from 90 to 250; at least 70 mol%, preferably at least 75 mol%, more preferably at least 80 mol% and even more preferably at least 85 mol% of the glycerol ester alkoxylates of the formula (I) in the mixture, in each case based on the total amount of the glycerol ester alkoxylates of the formula (I) in the mixture, are glycerol ester alkoxylates of the formula (I), wherein all of the groups R4, R5and R6are acyl groups; and at least 30 mol%, preferably at least 40 mol%, more preferably at least 50 mol%, even more preferably at least 60 mol% and particularly preferably at least 70 mol% of those groups R4, R5and R6, are linear or branched, preferably linear, saturated or unsaturated acyl groups comprising 16 to 20 carbon atoms or mixtures thereof and preferably are linear or branched, preferably linear, saturated or unsaturated acyl groups comprising 16 to 18 carbon atoms or mixtures thereof, in each case based on the total amount of the linear or branched, preferably linear, saturated or unsaturated acyl groups R4, R5and R6.

[0047] In the inventive mixtures of glycerol ester alkoxylates of the formula (I), those of the groups R4, R5and R6, which have a meaning different from hydrogen, are referred to as “acyl groups”. In the inventive mixtures of glycerol ester alkoxylate of the formula (I), the single acyl groups R4, R5and R6consist of a carbonyl group C=O and a hydrocarbon residue, without further substituents, e.g. without hydroxyl groups, on the hydrocarbon residue.

[0048] More preferably, acyl groups R4, R5and R6are of the formula -C(=O)-R4a, -C(=O)-R5aand - C(=O)-R6a, respectively, wherein the residues R4a, R5aand R6acomprise one carbon atom less than the respective acyl groups R4, R5and R6and are, independent from each other, selected from linear or branched, preferably linear, saturated alkyl groups, linear or branched, preferably linear, mono- or polyunsaturated alkenyl groups, or mixtures thereof. For example, in this more preferred embodiment of the invention, in case R4, R5and R6are, independent from each other, selected from linear or branched, preferably linear, saturated or unsaturated acyl groups comprising from 8 to 30 carbon atoms or mixtures thereof, R4a, R5aor R6aare, independent from each other, selected from linear or branched, preferably linear, saturated alkyl groups comprising from 7 to 29 carbon atoms, linear or branched, preferably linear, mono- or polyunsaturated alkenyl groups comprising from 7 to 29 carbon atoms, or mixtures thereof.

[0049] In a single glycerol ester alkoxylate molecule of the formula (I), an acyl group R4, R5or R6forms an ester bond, either (i) with an oxygen atom of one of the structural units -[R1O]-, -[R2O]- or - [R3O]- or (ii) with an oxygen atom of the glycerol residue -O-CH2-CH(O-)-CH2-O-.

[0050] WO 93 / 10072 A1 discloses the preparation of esters of fatty acids with ethoxylated polyols by (a) ethoxylating polyols in the presence of basic catalysts at high temperatures with 80 to 150 moles ethylene oxide per mol polyol and then (b) reacting the reaction product with 1 to 1 .3 moles fatty acids per mole of hydroxyl groups contained in the original polyol, in the presence of acid catalysts. These esters are useful as thickeners of aqueous solutions of surface active agents.

[0051] If present, the structural units -[R1O]-, -[R2O]- and -[R3O]- in the glycerol ester alkoxylates of the formula (I) are, independent from each other, selected from [(C2H4)O] or [(C3He)O].

[0052] If present, the structural units of the formula -[R1O]x-, -[R2O]y- and -[R3O]z- in a single glycerol ester alkoxylate molecule of the formula (I), independent from each other, may consist of one or more [(C2H4)O]-groups, may consist of one or more [(C3H6)O]- groups or may consist of a mixture of [(C2H4)O]- and [(C3H6)O]-groups. Within a single glycerol ester alkoxylate molecule of the formula (I), the structural units -[R1O]X-, -[R2O]y- and -[R3O]Z- may be the same or different.

[0053] The groups [(C2H4)O], if present in the structural units of the formula -[R1O]X-, -[R2O]y- and / or - [R3O]Z- of the glycerol ester alkoxylates of the formula (I), preferably are of the formula -CH2- CH2-O-.

[0054] The groups [(C3He)O], if present in the structural units of the formula -[R1O]X-, -[R2O]y- and / or - [R3O]Z- of the glycerol ester alkoxylates of the formula (I), preferably are of the formula - CH(CH3)-CH2-O- or -CH2-CH(CH3)-O-, i.e. of the formula

[0055] In the case that [(C2H4)O]- and [(C3He)]O-groups exist in a structural unit of the formula -[R1O]X-, -[R2O]y- and / or -[R3O]Z-, they may be arranged blockwise, alternating, periodically and / or statistically, preferably blockwise and / or statistically. This means that in a structural unit of the formula -[R1O]X-, -[R2O]y- and / or -[R3O]Z-, the groups [(C3H4)O] and [(C3He)O] may be arranged, for example, in a purely statistically or blockwise form but may also be arranged in a form which could be considered as both, statistical and blockwise, e.g. small blocks of [(C2H4)O] and [(C3H6)O] arranged in a statistical manner, or in a form wherein adjacent instances of statistical and blockwise arrangements of the groups [(C2H4)O] and [(C3H6)O] exist.

[0056] Any of the groups [(C2H4)O] and [(C3He)O] can be linked to -R4, -R5, -R6and an oxygen of the glycerol backbone in a glycerol ester alkoxylate molecule of the formula (I). This means, for example, that all, -R4, -R5, -R6and the oxygens of the glycerol backbone in a glycerol ester alkoxylate molecule of the formula (I), may be connected to a [(C2H4)O]-group, they may all be connected to a [(C3He)O]-group or they may be connected independently from one another to either group selected from [(C2H4)O] and [(C3He)O].

[0057] In a preferred embodiment of the invention, the structural units -[R1O]-, -[R2O]- and -[R3O]- in the mixture of glycerol ester alkoxylates of the formula (I) are [(C2H4)O].

[0058] Preferably, the variables x, y and z in the mixture of glycerol ester alkoxylates of the formula (I) are, based on a molar average, independent from each other, numbers from 0 to 150, more preferably from 0 to 125, even more preferably from 0 to 110, particularly preferably from 0 to 100, and extraordinarily preferably from 0 to 90, and wherein in the definitions above in this paragraph at least one of the variables x, y, and z is, based on a molar average, a number greater than 0.

[0059] In a more preferred embodiment of the invention, the variables x, y and z in the mixture of glycerol ester alkoxylates of the formula (I) are, based on a molar average, independent from each other, numbers from 2 to 149, even more preferably from 5 to 125, particularly preferably from 10 to 110, extraordinarily preferably from 20 to 100 and especially preferably from 30 to 90.

[0060] The variables x, y, and z are the same or different and are independently integer numbers for each single glycerol ester alkoxylate molecule of the formula (I) in the mixture according to the invention and may be the same or different for the various glycerol ester alkoxylate molecules in the mixture according to the invention.

[0061] The sum x+y+z is an integer number for each single glycerol ester alkoxylate molecule of the formula (I) in the mixture according to the invention and may be the same or different for the various glycerol ester alkoxylate molecules in the mixture according to the invention. Preferably, the sum x+y+z for a single glycerol ester alkoxylate molecule of the formula (I) in the mixture according to the invention is selected from integer numbers from 5 to 600, more preferably is selected from integer numbers from 10 to 500, even more preferably is selected from integer numbers from 20 to 400, and particularly preferably is selected from integer numbers from 30 to 300.

[0062] In a preferred embodiment of the invention, in the inventive mixtures of glycerol ester alkoxylates of the formula (I), at least 20 mol%, preferably at least 25 mol%, more preferably at least 30 mol%, even more preferably at least 35 mol% and particularly preferably at least 40 mol% of those groups R4, R5and R6, , are linear or branched, preferably linear, unsaturated acyl groups comprising 16 to 20 carbon atoms or mixtures thereof and preferably are linear or branched, preferably linear, unsaturated acyl groups comprising 16 to 18 carbon atoms or mixtures thereof, in each case based on the total amount of the acyl groups R4, R5and R6.

[0063] In a further preferred embodiment of the invention, in the inventive mixtures of glycerol ester alkoxylates of the formula (I), the groups R4, R5and R6are selected from hydrogen, acyl groups derived from palm oil, rape seed oil, refined rape seed oil, sunflower oil, high oleic sunflower oil, or mixtures thereof.

[0064] In the context of the present invention, “high oleic sunflower oil” refers to a sunflower oil, wherein the amount of the oleic acid residues in the oil, based on the total amount of fatty acid residues in the oil, is at least 50 mol%, preferably at least 60 mol%, more preferably at least 70 mol% and even more preferably at least 80 mol%.

[0065] “Refined rape seed oil” refers to a rapeseed oil wherein undesired impurities have been reduced or removed.

[0066] In case the mixture of glycerol ester alkoxylates of the formula (I) comprises acyl groups with 16 carbon atoms and acyl groups with 18 carbon atoms, the molar ratio of the acyl groups with 16 carbon atoms to the acyl groups with 18 carbon atoms preferably is not 1:1.

[0067] In case the mixture of glycerol ester alkoxylates of the formula (I) comprises saturated and unsaturated acyl groups with 16 carbon atoms and saturated and unsaturated acyl groups with 18 carbon atoms, the molar ratio of the sum of the saturated and unsaturated acyl groups with 16 carbon atoms to the sum of the saturated and unsaturated acyl groups with 18 carbon atoms preferably is < 1.0 and more preferably < 0.9.

[0068] In case the mixture of glycerol ester alkoxylates of the formula (I) comprises saturated acyl groups with 16 carbon atoms and saturated acyl groups with 18 carbon atoms, the molar ratio of the saturated acyl groups with 16 carbon atoms to the saturated acyl groups with 18 carbon atoms preferably is > 1.0, more preferably > 1.2 and even more preferably > 1.5.

[0069] In case the mixture of glycerol ester alkoxylates of the formula (I) comprises saturated and unsaturated acyl groups with 16 carbon atoms and saturated acyl groups with 18 carbon atoms, the molar ratio of the sum of the saturated and unsaturated acyl groups with 16 carbon atoms to the saturated acyl groups with 18 carbon atoms preferably is > 1.0, more preferably > 1.2 and even more preferably > 1.5.

[0070] In case the mixture of glycerol ester alkoxylates of the formula (I) comprises acyl groups with 16 carbon atoms and acyl groups with 18 carbon atoms, the weight ratio of the acyl groups with 16 carbon atoms to the acyl groups with 18 carbon atoms preferably is not 1:1. In case the mixture of glycerol ester alkoxylates of the formula (I) comprises saturated and unsaturated acyl groups with 16 carbon atoms and saturated and unsaturated acyl groups with 18 carbon atoms, the weight ratio of the sum of the saturated and unsaturated acyl groups with 16 carbon atoms to the sum of the saturated and unsaturated acyl groups with 18 carbon atoms preferably is < 1.0 and more preferably < 0.9.

[0071] In case the mixture of glycerol ester alkoxylates of the formula (I) comprises saturated acyl groups with 16 carbon atoms and saturated acyl groups with 18 carbon atoms, the weight ratio of the saturated acyl groups with 16 carbon atoms to the saturated acyl groups with 18 carbon atoms preferably is > 1.0, more preferably > 1.2 and even more preferably > 1.5.

[0072] In case the mixture of glycerol ester alkoxylates of the formula (I) comprises saturated and unsaturated acyl groups with 16 carbon atoms and saturated acyl groups with 18 carbon atoms, the weight ratio of the sum of the saturated and unsaturated acyl groups with 16 carbon atoms to the saturated acyl groups with 18 carbon atoms preferably is > 1.0, more preferably > 1.2 and even more preferably > 1.5.

[0073] Glycerol ester alkoxylates are already known in the prior art. Glycerol ester ethoxylates of the prior art are e. g. described in WO 2020 / 239750 A1 , WO 2020 / 239760 A1, WO 2021 / 078807 A1 , EP 4 067468 A1 , WO 2023 / 057335 A1 or WO 2023 / 083995 A1. Glycerol ester ethoxylates are also disclosed in ON 111234199 A, e.g. as latex paint thickening rheological agents.

[0074] Glycerol ester alkoxylates may be produced by the reaction of glycerol ester such as triglyceride with alkylene oxide e.g. using catalysts based on calcium or magnesium.

[0075] An alternative route to prepare glycerol ester alkoxylates is a transesterification reaction of a methyl ester or esterification reaction of a carboxylic acid with an alkoxylated glycerol.

[0076] The inventive mixture of glycerol ester alkoxylates of the formula (I) may advantageously be prepared by insertion alkoxylation, e.g. by alkoxylation of glycerol esters such as triglycerides using an alkaline earth metal catalyst.

[0077] A method for preparing an inventive mixture of glycerol ester alkoxylates of the formula (I), in particular an inventive mixture of glycerol ester alkoxylates of the formula (I)

[0078] wherein

[0079] R1, R2, R3, x, y, z, R4, R5, R6, and the sum of x + y + z, based on a molar average, are as defined above, and the amount of the glycerol ester alkoxylates of the formula (I), wherein all of the groups R4, R5and R6are as defined above, and the amount of those groups R4, R5and R6, which are acyl groups, and are linear or branched, preferably linear, saturated or unsaturated acyl groups comprising 16 to 20 carbon atoms or mixtures thereof and preferably are linear or branched, preferably linear, saturated or unsaturated acyl groups comprising 16 to 18 carbon atoms or mixtures thereof, is as defined above, from ethylene oxide, propylene oxide or a mixture of ethylene oxide and propylene oxide and a mixture of glycerol esters of the formula (II) wherein R4, R5and R6in the mixture of the glycerol esters of the formula (II) have the same meaning as in the mixture of the glycerol ester alkoxylates of the formula (I), characterized in that in the method a catalyst (C) based on an alkaline earth metal is used is disclosed herein.

[0080] In the method for preparing an inventive mixture of glycerol ester alkoxylates of the formula (I), R4, R5and R6in the mixture of the glycerol esters of the formula (II) have the same meaning as in the mixture of the glycerol ester alkoxylates of the formula (I). This e.g. means, that R4, R5and R6in the mixture of the glycerol esters of the formula (II), are, independent from each other, selected from hydrogen, linear or branched, preferably linear, saturated or unsaturated acyl groups comprising from 8 to 30 carbon atoms or mixtures thereof, and wherein, in the single glycerol ester molecules of the formula (II), at least one of the groups R4, R5and R6is an acyl group, and at least 70 mol% of the glycerol esters of the formula (II) in the mixture of the glycerol esters of the formula (II), based on the total amount of the glycerol esters of the formula (II) in the mixture of the glycerol esters of the formula (II), are glycerol esters of the formula (II), wherein all of the groups R4, R5and R6are acyl groups, and in the mixture of the glycerol esters of the formula (II), at least 30 mol% of those groups R4, R5and R6, which are acyl groups, are linear or branched, preferably linear, saturated or unsaturated acyl groups comprising 16 to 20 carbon atoms or mixtures thereof, based on the total amount of the linear or branched, preferably linear, saturated or unsaturated acyl groups R4, R5and R6.

[0081] Preferably, triglycerides of the formula (II) are used for the preparation of the inventive mixtures of alkoxylates of the formula (I) and are not admixed with other reactants that contain any free hydroxyl groups.

[0082] Preferably, in the method, the catalyst (C) is obtainable by a reaction involving

[0083] (a) an alkaline earth metal compound (A) and

[0084] (b) one or more substances selected from the group consisting of a carboxylic acid (B) preferably comprising 3 to 60, more preferably 3 to 46, carbon atoms; a polyalkylene glycol having a molecular weight from 100 g / mol to 1500 g / mol; a C1-C18 alkyl-capped polyalkylene glycol having a molecular weight from 100 g / mol to 1500 g / mol; an alcohol solvent; and mixtures including any of the foregoing, and

[0085] (c) a strong acid (AC).

[0086] The carboxylic acid (B) mentioned under component (b) above may e. g. be a carboxylic acid, wherein the carboxylic acid function -COOH is connected to a hydrocarbon group but may also e. g. be a carboxylic acid wherein the carboxylic acid function -COOH is connected to a hydrocarbon group that contains or is interrupted by ether functions.

[0087] The alcohol mentioned in component (b) is an alcohol wherein the hydroxyl function -OH is bonded to a hydrocarbyl group. Preferably, in the method the alcohol solvent is an alcohol solvent having 1 to 5 carbon atoms, more preferably propan-2-ol, or a mixture thereof with water.

[0088] Preferably, in the method the alkaline earth metal compound (A) is selected from the group consisting of magnesium hydroxide, magnesium acetate, magnesium carbonate, magnesium sulfate, magnesium phosphate, calcium hydroxide, calcium acetate, calcium carbonate, calcium sulfate, calcium phosphate, strontium hydroxide, strontium acetate, strontium carbonate, strontium sulfate, strontium phosphate, barium hydroxide, barium acetate, barium carbonate, barium sulfate, and barium phosphate. In a more preferred embodiment of the method the alkaline earth metal compound (A) is selected from the group consisting of calcium hydroxide, calcium acetate, calcium carbonate, calcium sulfate, and calcium phosphate. In another more preferred embodiment of the method the alkaline earth metal compound (A) is selected from the group consisting of magnesium hydroxide, magnesium acetate, calcium hydroxide, calcium acetate, strontium hydroxide, strontium acetate, barium hydroxide, and barium acetate.

[0089] Particularly preferably, in the method the alkaline earth metal compound (A) is selected from the group consisting of calcium acetate and calcium hydroxide.

[0090] Preferably, in the method the strong acid (AC) is an acid which has a PKA value of 3 or less, more preferably is selected from the group consisting of acids of sulfur oxides and phosphorus oxides, even more preferably from the group consisting of sulfuric acid, sulfurous acid, sulfonic acids (among the sulfonic acids methane sulfonic acid is preferred), phosphorus acid, phosphorous acid and phosphonic acids (among the phosphonic acids methane phosphonic acid is preferred) and particularly preferably from the group consisting of sulfuric acid, sulfurous acid and methane sulfonic acid. Extraordinarily preferably, in the method the strong acid (AC) is sulfuric acid.

[0091] Preferably, in the method the molar ratio of the alkaline earth metal compound (A) to the strong acid (AC) is from 1.0:0.1 to 1.0: 1.0, more preferably from 1.0:0.2 to 1.0:0.9 and even more preferably from 1.0:0.3 to 1.0:0.8.

[0092] Preferably, in the method the polyalkylene glycol having a molecular weight from 100 g / mol to 1500 g / mol is a polyethylene glycol having a molecular weight from 100 g / mol to 1500 g / mol. Preferably, in the method the C1-C18 alkyl-capped polyalkylene glycol having a molecular weight from 100 g / mol to 1500 g / mol is a methyl-capped polyalkylene glycol having a molecular weight from 100 g / mol to 1500 g / mol and more preferably is a methyl-capped polyethylene glycol having a molecular weight from 100 g / mol to 1500 g / mol.

[0093] Preferably, in the method volatile components are removed before the catalyst (C) is used for the preparation of the mixture of glycerol ester alkoxylates of the formula (I).

[0094] In one preferred embodiment of the method a carboxylic acid (B) is used in the preparation of the catalyst (C).

[0095] Preferably, in the method the molar ratio of alkaline earth metal compound (A) to carboxylic acid (B) in the preparation of the catalyst (C) is from 1 :1 to 1 :5.

[0096] Preferably, the carboxylic acid (B) is represented by formula (III),

[0097] R4-[O]q-[CH2CH2-O]p-CH2COOH (III) wherein

[0098] R4is selected from saturated or unsaturated, linear or branched Ci to C30 hydrocarbyl groups, preferably Ci to C22hydrocarbyl groups, and more preferably Ce to C18 hydrocarbyl groups, q is 0 or 1 , and p is, based on molar average, a number from 0 to 11 , preferably from 1 to 11 , more preferably from 1 to 9, and even more preferably from 2 to 7.

[0099] In a more preferred embodiment of the method, the carboxylic acid (B) is represented by formula (III),

[0100] R4-[O]q-[CH2CH2-O]P-CH2COOH (III) wherein

[0101] R4is selected from saturated or unsaturated, linear or branched Ci to C30 hydrocarbyl groups, preferably Ci to C22hydrocarbyl groups, and more preferably Ce to C18 hydrocarbyl groups, q is 0, and p is 0, and preferably is isononanoic acid or oleic acid. In another more preferred embodiment of the method, the carboxylic acid (B) is represented by formula (III),

[0102] R4-[O]q-[CH2CH2-O]p-CH2COOH (III) wherein

[0103] R4is selected from saturated or unsaturated, linear or branched Ci to C30 hydrocarbyl groups, preferably Ci to C22hydrocarbyl groups, and more preferably Ce to Cis hydrocarbyl groups, q is 1 , and p is, based on molar average, a number from 0 to 11 , preferably from 1 to 11 , more preferably from 1 to 9, and even more preferably from 2 to 7, and preferably, R4is oleyl, q is 1 , and p is, based on molar average, 5.

[0104] In one preferred embodiment of the method the catalyst (C) is obtainable by a reaction involving

[0105] (a) calcium hydroxide and

[0106] (b) a carboxylic acid (B), which is represented by formula (III),

[0107] R4-[O]q-[CH2CH2-O]P-CH2COOH (III) wherein

[0108] R4is selected from saturated or unsaturated, linear or branched Ci to C30 hydrocarbyl groups, preferably Ci to C22hydrocarbyl groups, and more preferably Ce to Cis hydrocarbyl groups, q is 0, and p is 0, and preferably is isononanoic acid, and an alcohol solvent, preferably an alcohol solvent having 1 to 5 carbon atoms, more preferably propan-2-ol, or a mixture thereof with water, and (c) sulfuric acid.

[0109] In another preferred embodiment of the method the catalyst (C) is obtainable by a reaction involving

[0110] (a) calcium hydroxide and (b) a carboxylic acid (B), which is represented by formula (III),

[0111] R4-[O]q-[CH2CH2-O]p-CH2COOH (III) wherein

[0112] R4is selected from saturated or unsaturated, linear or branched Ci to C30 hydrocarbyl groups, preferably Ci to C22hydrocarbyl groups, and more preferably Ce to Cis hydrocarbyl groups, q is 1 , and p is, based on molar average, a number from 0 to 11 , preferably from 1 to 11 , more preferably from 1 to 9, and even more preferably from 2 to 7, and preferably, R4is oleyl, q is 1 , and p is, based on molar average, 5, and an alcohol solvent, preferably an alcohol solvent having 1 to 5 carbon atoms, more preferably propan-2-ol, or a mixture thereof with water, and

[0113] (c) a strong acid and preferably sulfuric acid.

[0114] In another preferred embodiment of the method the catalyst (C) is obtainable by a reaction involving

[0115] (a) calcium acetate and

[0116] (b) a polyalkylene glycol having a molecular weight from 100 g / mol to 1500 g / mol or mixtures of such polyalkylene glycols, and

[0117] (c) sulfuric acid.

[0118] In another preferred embodiment of the method the catalyst (C) is obtainable by a reaction involving

[0119] (a) calcium acetate and

[0120] (b) a carboxylic acid (B), which is represented by formula (III),

[0121] R4-[O]q-[CH2CH2-O]P-CH2COOH (III) wherein R4is selected from saturated or unsaturated, linear or branched Ci to C30 hydrocarbyl groups, preferably Ci to C22 hydrocarbyl groups, and more preferably Ce to Cis hydrocarbyl groups, q is 0, and p is 0, and preferably, is oleic acid, and a C1-C18 alkyl-capped polyalkylene glycol having a molecular weight from 100 g / mol to 1500 g / mol, preferably a methyl-capped polyalkylene glycol having a molecular weight from 100 g / mol to 1500 g / mol and more preferably a methyl-capped polyethylene glycol having a molecular weight from 100 g / mol to 1500 g / mol or mixtures of such alkyl- capped polyalkylene glycols, and

[0122] (c) sulfuric acid.

[0123] In another preferred embodiment of the method the catalyst (C) is obtainable by a reaction involving

[0124] (a) calcium acetate and

[0125] (b) an alcohol solvent, preferably an alcohol solvent having 1 to 5 carbon atoms, more preferably propan-2-ol, or a mixture thereof with water, and

[0126] (c) sulfuric acid.

[0127] In the method for preparing the mixture of alkoxylates of the formula (I), the molar ratio of the alkylene oxide selected from the group consisting of ethylene oxide, propylene oxide and mixtures of ethylene oxide and propylene oxide to the one or more glycerol esters of the formula (II) preferably is from 50:1 to 300:1 , more preferably from 60:1 to 300:1 , even more preferably from 70:1 to 280:1 , particularly preferably from 85:1 to 250:1 , and extraordinarily preferably from 90:1 to 250:1.

[0128] The molar ratio of alkaline earth metal compound (A) to carboxylic acid (B) (molar ratio (A):(B)) in the preparation of the catalyst (C) preferably is from 1 :1 to 1 :5. More preferably, the molar ratio (A):(B) is from 1 :1.5 to 1 :4, even more preferably from 1 :1.8 to 1 :2.2 and particularly preferably from 1 :1.9 to 1 :2.1. In an extraordinarily preferred embodiment of the method the molar ratio of (A):(B) in the preparation of the catalyst (C) is approximately 1 :2. In one preferred embodiment of the method the reaction for the preparation of the catalyst (C) is carried out in the presence of at least one polar solvent, more preferably a polar solvent comprising at least one hydroxyl group, even more preferably at least one alcohol having 1 to 5 carbon atoms or a mixture thereof with water. In a particularly preferred embodiment, the polar solvent is propan-2-ol or a mixture thereof with water. In another particularly preferred embodiment, the polar solvent is ethanol or a mixture thereof with water.

[0129] It is advisable to perform the reaction for obtaining the catalyst (C) in the presence of an acid (AC) which has a PKA value of 3 or less, preferably 2 or less, more preferably 0 or less, and often -3 or less.

[0130] Preferably the acid (AC) is selected from the group consisting of acids of sulfur oxides and phosphorus oxides, more preferably from the group consisting of sulfuric acid, sulfurous acid, sulfonic acids (among the sulfonic acids methane sulfonic acid is preferred), phosphorus acid, phosphorous acid and phosphonic acids (among the phosphonic acids methane phosphonic acid is preferred). Sulfuric acid, sulfurous acid and methane sulfonic acid are of particular interest.

[0131] In a particularly preferred embodiment of the method the reaction for obtaining the catalyst (C) is performed in the presence of sulfuric acid.

[0132] It is particularly advantageous to prepare the alkaline earth metal catalyst (C) by first allowing the alkaline earth metal compound (A) to react with the carboxylic acid (B), preferably in a solvent as described above, after which the reaction mixture is further treated with the acid (AC).

[0133] It is also particularly advantageous to prepare the alkaline earth metal catalyst (C) by first dispersing the alkaline earth metal compound (A) in a polyalkylene glycol having a molecular weight from 100 g / mol to 1500 g / mol or mixtures of such polyalkylene glycols, or in a C1-C18 alkyl-capped polyalkylene glycol having a molecular weight from 100 g / mol to 1500 g / mol, preferably a methyl-capped polyalkylene glycol having a molecular weight from 100 g / mol to 1500 g / mol and more preferably a methyl-capped polyethylene glycol having a molecular weight from 100 g / mol to 1500 g / mol or mixtures of such alkyl-capped polyalkylene glycols, optionally in the presence of water, after which the reaction mixture is further treated with the acid (AC). The dispersing step may be performed in the presence of a carboxylic acid (B), which is represented by formula (III),

[0134] R4-[O]q-[CH2CH2-O]p-CH2COOH (III) wherein

[0135] R4is selected from saturated or unsaturated, linear or branched Ci to C30 hydrocarbyl groups, preferably Ci to C22hydrocarbyl groups, and more preferably Ce to Cis hydrocarbyl groups, q is 0, and p is 0, and preferably is oleic acid.

[0136] It is also particularly advantageous to prepare the alkaline earth metal catalyst (C) by first dispersing the alkaline earth metal compound (A) in an alcohol solvent, preferably an alcohol solvent having 1 to 5 carbon atoms, more preferably propan2-ol, or a mixture thereof with water, after which the reaction mixture is further treated with the acid (AC).

[0137] For the reaction by which the alkaline earth metal catalyst (C) is obtained, any common reactor may be employed, preferably a reactor with an agitating / mixing means, such as, e.g., a magnetic stirrer, a mechanical stirrer, a static mixer, a blender, a batch disperser, or a Rotor- Stator disperser.

[0138] The preparation of the catalyst (C) is preferably carried out under a pressure of from 0.5 to 2 bar, more preferably from 0.8 to 1.5 bar, even more preferably from 0.9 to 1.2 bar. In a preferred embodiment of the method the catalyst is prepared under atmospheric pressure. Furthermore, the catalyst (C) is preferably prepared at a temperature of from -30 °C to 80 °C, preferably from -10 °C to 60 °C, more preferably from 0 °C to 50 °C. In a preferred embodiment of the method the catalyst is prepared at a temperature of from 20 to 40 °C, especially at room temperature.

[0139] The thus prepared alkaline earth metal catalyst (C), preferably the calcium catalyst, typically has a content of alkaline earth metal ions, preferably Ca2+ions, that is from 0.5 to 10 wt.-%, often from 1 to 7 wt.-%, often from 2.0 to 5.5 wt.-%. Optionally, the catalyst may be purged of volatile components, such as the solvent, water and other volatile byproducts by employing commonly used methods. Preferably, the volatile components are removed in vacuo, e.g. under a pressure below 0.8 bar, preferably below 0.3 bar, more preferably below 0.1 bar, and / or at elevated temperatures, e.g. 50 to 180 °C, preferably 70 to 150 °C, more preferably 80 to 140 °C.

[0140] In a particularly preferred embodiment of the method the volatile compounds are removed on a rotary evaporator at a pressure below 0.1 bar and a temperature of from 80 °C to 140 °C.

[0141] Preferably, the method for preparing a mixture of glycerol ester alkoxylates of the formula (I) according to the invention comprises the steps of i) introducing the catalyst (C) as defined above and one or more glycerol esters of the formula (II) as described above into a pressure-resistant reactor; ii) optionally replacing the air in the reactor with nitrogen or other protective gas; iii) optionally drying the reactor content at a temperature of from 50 to 200 °C and / or a pressure below 0.8 bar; iv) heating the content of the reactor to a temperature of from 80 °C to 200 °C; v) optionally pressurizing the reactor with nitrogen or other protective gas to a pressure of from 0.3 bar to 3.5 bar above atmospheric pressure; vi) pressurizing the reactor with alkylene oxide gas selected from the group consisting of ethylene oxide gas, propylene oxide gas and mixtures of ethylene oxide gas and propylene oxide gas to a pressure of from 1.5 bar to 10 bar above atmospheric pressure with the proviso that the pressure is above the pressure prior to step vi); vii) allowing the mixture to react until the pressure in the reactor is constant.

[0142] In step i), the catalyst (C) may be introduced as obtained from the reaction of its preparation described above directly, or in its form that has been purged of volatile compounds, but preferably as obtained from the reaction of its preparation described above directly. The glycerol esters of formula (II) may be introduced in their raw form or may be purified prior to use.

[0143] The catalyst (C) is preferably introduced into the reactor in an amount from 0.5 to 5 wt.-%, preferably from 1 to 3 wt.-%, more preferably from 1 to 2 wt.-% based on the total weight of the mixture of glycerol esters of formula (II) and alkylene oxide selected from the group consisting of ethylene oxide, propylene oxide and mixtures of ethylene oxide and propylene oxide.

[0144] The pressure-resistant reactor is not particularly limited but is designed to withstand the pressures employed in the process, thus that it is not damaged during the process. Preferably, the reactor is designed to withstand pressures both above 10 bar, more preferably above 15 bar, and below 0.01 bar, more preferably below 0.001 bar. Preferably, the pressure-resistant reactor is an autoclave, more preferably an autoclave equipped with an agitating means such as a magnetic or a mechanical stirrer.

[0145] Generally, the replacement of air in the reactor with nitrogen or other protective gas is not necessarily required, because the mixture of glycerol ester alkoxylates of the formula (I) according to the invention would at least partially be generated in the process. However, air, particularly oxygen, in the reactor may lead to safety concerns during alkoxylation reactions in general and decomposition products due to oxidation and / or hydrolysis of the employed materials and of the generated products, especially at elevated temperatures. Therefore, it is advisable to carry out step ii) of the method after step i).

[0146] In general, the step of drying the reactor content is also not necessarily required, because the mixture of glycerol ester alkoxylates of the formula (I) according to the invention would at least partially be generated in the process. However, water and alcohols may facilitate hydrolysis and transesterification of the employed materials and of the generated products under the reaction conditions. Especially if in step i) the catalyst (C) is introduced into the reactor as obtained from the reaction of its preparation described above directly, it is advisable to carry out the drying step, since the directly obtained catalyst (C) typically contains residues of polar solvents or their mixtures with water. In case the catalyst (C) is purged of volatile components before introducing it into the reactor, the drying step iii) may be omitted. Nevertheless, in this case it may be advisable to carry out step iii) since volatile components may also be present as impurities in the one or more glycerol esters of formula (II). Therefore, in particularly preferred embodiments, step iii) is carried out.

[0147] The step iii) of drying the reactor content is typically performed at a temperature of from 50 °C to 200 °C, preferably of from 50 °C to 180 °C, more preferably of from 60 °C to 150 °C, even more preferably of from 70 °C to 130 °C, particularly preferably of from 80 °C to 120 °C, and at a pressure below 0.8 bar, preferably below 0.1 bar, more preferably below 0.05 bar. The thus generated vacuum is preferably a dynamic vacuum.

[0148] The vacuum pump for generating the vacuum is not particularly limited; it is, however, preferable to use an aspirator for generating the vacuum. Furthermore, it is advisable to reduce the pressure and increase temperature in the reactor gradually to prevent boiling retardation. In a particularly preferred embodiment, the step of drying the reactor content is carried out at a temperature of from 80 °C to 120 °C and a pressure below 0.01 bar, preferably over a period of at least 15 minutes, more preferably over a period of at least 30 minutes, even more preferably over a period of at least 1 hour. It is particularly preferred to dry the content of the reactor to constant mass.

[0149] After the drying step iii), the fluid line between the vacuum pump and the reactor is interrupted, to ensure that the components added to the reactor after the drying remain in the reactor and are not directly withdrawn therefrom. Furthermore, it is preferable to compensate the vacuum in the reactor with nitrogen or other protective gas before carrying out the further steps, to reduce the risk of air entering the reactor.

[0150] Step iv) of heating the content of the reactor is generally performed at a temperature of from 80 °C to 200 °C, preferably from 120 °C to 190 °C, more preferably from 160 °C to 180 °C. This temperature is maintained at least until step vi) is finished, preferably until step vii) is finished.

[0151] After setting the temperature in step iv), the reactor may be optionally pressurized in step v) with nitrogen or other protective gas to a pressure of from 0.3 to 3.5 bar, preferably of from 0.4 to 3.3 bar, more preferably of from 0.5 to 3.0 bar, even more preferably of from 0.7 to 2.5 bar and particularly preferably of from 0.8 to 2.2 bar above atmospheric pressure. By carrying out this step v), alkylene oxide selected from the group consisting of ethylene oxide, propylene oxide and mixtures of ethylene oxide and propylene oxide introduced in the following step is diluted with the protective gas, thus that pressure-controlled dosage of alkylene oxide into the reactor is facilitated.

[0152] In step vi) the reactor is further pressurized with alkylene oxide selected from the group consisting of ethylene oxide, propylene oxide and mixtures of ethylene oxide and propylene oxide to a total internal pressure of from 1.5 to 10 bar, preferably from 2 to 8 bar, more preferably from 3 to 6 bar, even more preferably from 4 to 5 bar, above atmospheric pressure, with the proviso that the pressure in step vi) is above the pressure before step vi).

[0153] During step vii), after introduction of the intended amount of alkylene oxide selected from the group consisting of ethylene oxide, propylene oxide and mixtures of ethylene oxide and propylene oxide, the alkylene oxide inlet is closed and the reaction is allowed to proceed until the pressure in the reactor is constant.

[0154] In the sense of the invention, the pressure is considered constant, if it does not change by more than 0.05 bar over a period of 15 minutes, preferably 30 minutes, more preferably 1 hour. It is particularly preferred that the pressure in the reactor does not change by more than 0.01 bar over a period of 1 hour.

[0155] After completion of step vii), it is advisable to remove residual alkylene oxide from the reactor before isolating the mixture of glycerol ester alkoxylates of the formula (I) according to the invention, in order to prevent any unwanted reactions with alkylene oxide from taking place after isolation of the product. Preferably, residual alkylene oxide is removed from the reactor by cooling the reactor content to a temperature of from 50 to 120 °C, more preferably from 70 to 100 °C and even more preferably from 85 to 95 °C, and employing a pressure of below 0.8 bar, preferably below 0.1 bar, more preferably below 0.05 bar. The thus generated vacuum is preferably a dynamic vacuum. The vacuum pump for generating the vacuum is not particularly limited; it is, however, preferable to use an aspirator for generating the vacuum. Removal of residual alkylene oxide under these conditions is preferably carried out for at least 10 minutes, more preferably at least 30 minutes and even more preferably at least 1 hour.

[0156] The method of isolation of the mixture of glycerol ester alkoxylates of the formula (I) according to the invention is not particularly limited. However, it is preferable to isolate the product at elevated temperatures, specifically at temperatures of from 50 to 150 °C, preferably from 60 to 140 °C, more preferably from 80 to 120 °C. At these temperatures, the mixture of glycerol ester alkoxylates of the formula (I) according to the invention is typically in a liquid state and has a sufficiently low viscosity, and therefore may be transferred out of the reactor more easily than in the solid state, e.g. by pouring the product out of the reactor or via a bottom valve, thereby minimizing the amount of residues in the reactor. Thus, the subsequent cleaning and maintenance of the reactor is also facilitated. The method for preparing a mixture of glycerol ester alkoxylates of the formula (I) according to the invention using the catalyst (C) described above may be interrupted at any stage, and continued at a later point in time, without the reaction time being significantly increased.

[0157] In a preferred embodiment the sum x+y+z in the mixtures of alkoxylates of the formula (I), is, based on a molar average, a number from 90 to 200, more preferably from 90 to 190 and even more preferably from 90 to 110 or from 160 to 190. In a particularly preferred embodiment the sum x+y+z in the inventive mixtures of alkoxylates of the formula (I), is, based on a molar average, a number from 90 to 110. In another particularly preferred embodiment the sum x+y+z in the inventive mixtures of alkoxylates of the formula (I), is, based on a molar average, a number from 160 to 190. Accordingly, in a preferred embodiment of the method for preparing the inventive mixtures of alkoxylates of the formula (I), the molar ratio of the alkylene oxide selected from the group consisting of ethylene oxide, propylene oxide and mixtures of ethylene oxide and propylene oxide to the one or more glycerol esters of the formula (II) is from 90:1 to 200:1, more preferably from 90:1 to 190:1 and even more preferably from 90:1 to 110:1 or from 160:1 to 190:1. In a particularly preferred embodiment of the method for preparing the inventive mixtures of alkoxylates of the formula (I), the molar ratio of the alkylene oxide selected from the group consisting of ethylene oxide, propylene oxide and mixtures of ethylene oxide and propylene oxide to the one or more glycerol esters of the formula (II) is from 90:1 to 110:1. In another particularly preferred embodiment of the method for preparing the inventive mixtures of alkoxylates of the formula (I), the molar ratio of the alkylene oxide selected from the group consisting of ethylene oxide, propylene oxide and mixtures of ethylene oxide and propylene oxide to the one or more glycerol esters of the formula (II) is from 160:1 to 190:1. In the preferred inventive mixtures of glycerol ester alkoxylates of the formula (I) mentioned in this paragraph above, the groups R4, R5and R6are preferably selected from hydrogen, acyl groups derived from palm oil, rape seed oil, refined rapeseed oil, sunflower oil, high oleic sunflower oil, or mixtures thereof and more preferably selected from hydrogen, acyl groups derived from palm oil, rape seed oil, refined rape seed oil, high oleic sunflower oil, or mixtures thereof.

[0158] The mixture of glycerol ester alkoxylates of the formula (I) according to the invention may occur together with starting material used for its preparation, in particular glycerol ester in case the inventive mixture is prepared by alkoxylation of glycerol esters (in the following referred to as “composition A”). In case glycerol ester is present in the compositions A, the glycerol ester may be present in an amount of 0.1 wt.-% or more, or 0.25 wt.-% or more, or 0.5 wt.-% or more, or 1.0 wt.-% or more, in each case based on the total weight of the composition A. In case glycerol ester is present in the compositions A, the glycerol ester is present in an amount of preferably less than 20.0 wt.-%, more preferably less than 10.0 wt.-%, even more preferably less than 5.0 wt.-%, particularly preferably less than 2.0 wt.-% and extraordinarily preferably less than 1.0 wt- %, in each case based on the total weight of the composition A.

[0159] During the preparation of the mixture according to the invention, by-products may be formed. The formation of by-products in chemical reactions is quite normal since these reactions usually do not take place with a selectivity of 100 %. However, in case by-products are formed during the preparation of the mixture according to the invention, these by-products are formed in an amount of preferably less than 25.0 wt.-%, more preferably less than 20.0 wt.-%, even more preferably less than 15.0 wt.-%, particularly preferably less than 10.0 wt.-%, extraordinarily preferably less than 6.0 wt.-% and especially preferably less than 5.0 wt.-%, in each case based on the combined total weight of the mixture according to the invention and the by-products, and in particular in case the inventive mixture is prepared by a method according to the invention.

[0160] Starting material, and in particular glycerol ester, occurring together with the mixture according to the invention is considered to form part of the by-products.

[0161] Furthermore, the mixture according to the invention may be purified after its preparation and prior to its use, e.g. by distilling, stripping or filtering-off byproducts, but in a preferred embodiment, the mixture may be used as obtained without prior purification.

[0162] The alkoxylation product comprises a mixture of glycerol ester alkoxylates of the formula (I) according to the invention and may optionally comprise further substances such as starting materials or reactants, in particular glycerol esters of the formula (II), and / or by-products.

[0163] The inventive mixtures of glycerol ester alkoxylates of the formula (I) or the inventive alkoxylation product may also be bio-based.

[0164] Bio-based glycerol ester alkoxylates of formula (I) can, for example, be prepared from (i) glycerol esters of the formula (II) such as triglycerides and (ii) ethylene oxide, propylene oxide or mixtures of ethylene oxide and propylene oxide, wherein at least a part of one of the aforementioned alkylene oxides is bio-based. Bio-based ethylene oxide can be obtained from bio-ethanol, which can be obtained from natural sources like corn, sugarcane, or cellulosic biomass through fermentation. Bio-ethanol is then dehydrated to produce bio-ethylene. The bioethylene is then oxidized with oxygen over a silver catalyst to produce bio-based ethylene oxide.

[0165] Bio-based propylene oxide can be obtained from

[0166] 1 ) bio-glycerol, which can be obtained from biodiesel production, hydrolysis of vegetable oils, or fermentation of sugars. Bio-glycerol is then converted to acrolein via dehydration. Acrolein is hydrogenated to produce bio-propanol and subsequently dehydrated to provide biopropylene, which is epoxidized to produce propylene oxide using hydrogen peroxide; or

[0167] 2) bio-ethanol, which can be obtained from natural sources like corn, sugarcane, or cellulosic biomass through fermentation. Bio-ethanol is then dehydrated to produce bioethylene. The bio-ethylene is then catalytically dimerized to bio-butene. Bio-butene and bioethylene are then converted to biopropylene via metathesis. The bio-propylene is then catalytically converted to propylene oxide.

[0168] Preferably, the materials used to prepare the inventive mixture of glycerol ester alkoxylates of the formula (I) or the inventive alkoxylation product are bio-based and derived from natural sources. More preferably, the inventive mixture of glycerol ester alkoxylates of the formula (I) or the inventive alkoxylation product has at least 25 wt.-%, preferably at least 50 wt.-%, more preferably at least 75 wt.-%, even more preferably at least 90 wt.-% and particularly preferably 100 wt.-% bio-based carbon content, in each case relative to the total mass of carbon in the mixture of alkoxylates of the formula (I) or relative to the total mass of carbon in the alkoxylation product, respectively.

[0169] Preferably, the hydroxyl number of the alkoxylation product according to the invention is smaller than 15 mg KOH / g, more preferably smaller than 10 mg KOH / g and even more preferably smaller than 5 mg KOH / g. The hydroxyl number is measured according to DIN EN ISO 4629-2.

[0170] Mixtures of glycerol ester alkoxylates of the formula (I) which have been prepared via insertion alkoxylation as described above or the inventive alkoxylation products show an advantageous biodegradability. Perfume

[0171] The compositions described herein comprise 0.1 to 20 wt.% perfume. Preferably the compositions comprise 0.5 to 15 wt.% perfume and most preferably 1 to 10 wt.% perfume.

[0172] Perfume is considered to be any non-encapsulated perfume in the composition.

[0173] Particularly preferred perfume components are blooming perfume components and substantive perfume components. Blooming perfume components are defined by a boiling point less than 250°C and a LogP or greater than 2.5. Substantive perfume components are defined by a boiling point greater than 250°C and a LogP greater than 2.5. Boiling point is measured at standard pressure (760 mm Hg). Preferably a perfume composition will comprise a mixture of blooming and substantive perfume components. The perfume composition may comprise other perfume components.

[0174] It is commonplace for a plurality of perfume components to be present in a free oil perfume composition. In the compositions for use in the present invention it is envisaged that there will be three or more, preferably four or more, more preferably five or more, most preferably six or more different perfume components. An upper limit of 300 perfume components may be applied.

[0175] Preferably the perfume comprises at least one ingredient selected from: Aldehyde C12 MNA, verdyl acetate, cyclamen aldehyde, beta ionone, hexyl salicylate, tonalid, and combinations thereof. These ingredients show a particular benefit on wet fabrics.

[0176] In addition to the perfume, the compositions may comprise perfume microcapsules, in other words encapsulated perfume. The encapsulating materials, preferably comprise, but are not limited to; aminoplasts, proteins, polyvinyl acetates, polyurethanes, polyacrylates, polymethacrylates, polysaccharides, polyamides, polyolefins, gums, silicones, lipids, modified cellulose, polyphosphate, polystyrene, polyesters or combinations thereof. More preferably the encapsulating materials comprise polyvinyl acetate, proteins, polysaccharides or combinations thereof.

[0177] If encapsulated perfume is present it is preferably present at a level of from 0.01 to 2 percent by weight of the total weight of the fabric conditioning composition, more preferably from 0.02 to 1.5% and most preferably from 0.03 to 1 percent by weight of the total weight of the fabric conditioning composition.

[0178] Viscosity

[0179] The viscosity of fabric conditioning compositions according to the invention is driven by consumer preference. Consumers prefer products that have an appreciable viscosity, as this connotes efficacy. It further helps consumers to dose accurately as unintended splashes are then minimized when dosing the composition.

[0180] Viscosity can be measured by many methods known to those skilled in the art, for example using a cone and plate rheometer. A suitable method is to use an MCR 302 rheometer ex. Anton Paar, at 20°C, with a cone and plate geometry (CP-50) and a 2 degree cone angle.

[0181] When measured using such a method the viscosity of a composition according to the invention is at least 100mPa.s when measured at a shear rate of 20s-1, more preferably the viscosity is at least 200mPa.s and no greater than 500mPa.s and most preferably the viscosity is at least 300mPa.s and no greater than 400mPa.s when measured at a shear rate of 20s-1.

[0182] Further ingredients

[0183] The compositions described herein may comprise further ingredients suitable for use in fabric conditioners and known to the person skilled in the art. A non-limiting list of such ingredients include: non-ionic surfactants, fatty acids, fatty esters, solvents, antifoams, anti-malodour ingredients, insect repellents, shading or hueing dyes, preservatives (e.g. bactericides), pH buffering agents, perfume carriers, hydrotropes, anti-redeposition agents, soil-release agents, dye transfer inhibitors, polyelectrolytes, anti-shrinking agents, anti-wrinkle agents, anti-oxidants, dyes, colorants, sunscreens, anti-corrosion agents, drape imparting agents, anti-static agents, oils (e.g. plant based oils and mineral oils), plant extracts, waxes, sugar-esters, silicones, sequestrants, ironing aids, pearlisers or opacifiers.

[0184] The fabric conditioner composition is preferably in an aqueous form. The compositions preferably comprise at least 75 wt.% water. The compositions may be opaque, translucent, or transparent.

[0185] The fabric conditioner compositions are preferably used in the rinse stage of the laundry cycle. The laundry cycle or laundry process may be machine washing or hand washing. In one aspect is provided a method whereby the glycerol ester alkoxylate is added sequentially after the free oil perfume when the ingredients to manufacture the composition according to the first aspect of the invention are mixed together.

[0186] In one aspect there is provided a method of treating fabrics, wherein a fabric conditioner composition as described herein is delivered to the fabric in the rinse stage of a laundry process.

[0187] In the method of treating fabrics, the fabric conditioner composition as described herein is typically present in the rinse liquor of a laundry process from 0.01 g / l to 20g / l, more preferably from 0.05g / l to 20g / l, more preferably from 0.1 g / l to 15g / l, more preferably from 0.5g / l to 15g / l, more preferably from 1 g / l to 10g / I and most preferably from 1 g / l to 10g / I.

[0188] In a further aspect is provided a use of a fabric conditioner as described herein to provide conditioning to a fabric surface whilst not significantly compromising said fabric’s wettability, wherein a composition as described herein is delivered to the fabric in the rinse stage of a laundry process. Not significantly comprising said fabric’s wettability means that the wettability of a treated fabric compared to an untreated fabric is within 20% when measured according to the AATCC 97-2007 test method. : Synthesis of inventive glycerol ester alkoxylates

[0189] The following procedure was used to synthesize inventive examples of glycerol ester alkoxylates (from high oleic sunflower oil, palm oil and refined rapeseed oil).

[0190] Preparation of calcium catalyst:

[0191] A mixture of 1047.0 g of a carboxylic acid under the trade name “Emulsogen™ COL 050” marketed by Clariant Produkte (Deutschland) GmbH, 55.8 g of calcium hydroxide and 360.6 g of propan-2-ol was agitated at ambient temperature for 5 minutes with a batch disperser (Ultra Turrax from I KA Werke GmbH & Co KG). After this, 44.2 g of concentrated sulfuric acid were added over two minutes and the mixture was again agitated for 5 minutes with the batch disperser, providing a catalyst with a Ca2+content of 2.00 wt.-%. Alkoxylation procedure:

[0192] The glycerol ester of the corresponding oil and the catalyst were placed into a glass autoclave, which was then flushed with nitrogen by alternatingly applying vacuum and introducing nitrogen (3 cycles). The mixture was dried under aspirator vacuum at 120°C for 15 minutes. The pressure in the autoclave was restored to ambient with nitrogen and heated to 160°C. At this temperature the autoclave was pressurized with nitrogen to a pressure of 1.0 bar above atmospheric pressure, after which pressure-controlled dosage of alkylene oxide, preferably ethylene oxide, took place up to a maximum pressure of 5.5 bar above atmospheric pressure.

[0193] The alkoxylation is carried out in a semi-batch process with automated dosage of additional alkylene oxide within a given temperature window and up to the specified maximum pressure. The pressure is adjusted according to the increased filling volume of the vessel. After introduction of the intended amount of alkylene oxide and closing the alkylene oxide inlet, the reaction was continued until the pressure became constant.

[0194] The reactor content was cooled to 100°C and aspirator vacuum was applied for 60 minutes to remove residual alkylene oxide. The temperature was reduced to 80°C and the final product was transferred into storage vessels and analyzed. The typical batch scale was 400g to 2000 g. The uptake of the intended amount of alkylene oxide is assured by gravimetry and by determination of the saponification value according to DIN EN ISO 3681.

[0195] The materials that were produced are shown in table 1 (molar equivalents):

[0196] Table 1: Synthesis of inventive glycerol ester alkoxylates: Example 2: Compositions produced using glycerol ester alkoxylates

[0197] Table 1: Summary of compositions prepared

[0198] 1= Triethanolamine quaternary ammonium compound.

[0199] 2= Copolymer of acrylamide and 2-(dimethylamino)ethyl methacrylate chloride, available from SNF as Flosoft555

[0200] The compositions were prepared by the following methods:

[0201] Comparative composition:

[0202] The water was heated to a temperature of 45°C, minors were then added. The fabric softening active was heated to ~ 65°C and added into the solution. The copolymer was then added. The mixture was then cooled to ~37°C and the perfume oil and perfume microcapsules were then added. The mixture was then cooled to room temperature.

[0203] Inventive composition:

[0204] The water was heated to a temperature of 45°C, minors were then added. The glycerol ester alkoxylate was then added and stirred until fully mixed in. The fabric softening active was heated to ~ 65°C and added into the solution. The mixture was then cooled to ~37°C and the perfume oil and perfume microcapsules were then added. The mixture was then cooled to room temperature. Example 3: Wetting data

[0205] Wetting experiments were performed using a Terg-O-Tometer v2 under the following conditions:

[0206] Fabric: 40g knitted cotton

[0207] Water volume: 1 litre

[0208] Water type: demineralised

[0209] Rinse time: 10 mins

[0210] Spin: 30 seconds

[0211] Temperature: Ambient (~20°C)

[0212] The fabric was pre wet in the Terg-O-Tometer, removed and lightly squeezed to remove excess water. The composition to be tested (composition A or 1) was then pre-dispersed in the Terg-O- Tometer to provide 0.1 % active. The pre-wetted fabric was added back into the Terg-O- Tometer and rinsed for 10 minutes. The rinsed fabric wash then spun for 30 seconds prior to line drying in air for 24 hours.

[0213] Water absorbency was measured according to the AATCC 97-2007 method using 50ul droplets of water. The results obtained are recorded below in table 4.

[0214] Table 4: results

[0215] Compositions comprising glycerol ester alkoxylates according the invention have increased water absorbency. Example 4: Rheological data

[0216] The following compositions were made up to compare the performance of a composition according to the invention with one comprising a glycerol ester alkoxylate not according to the invention.

[0217] Table 5: compositions produced:

[0218] 3 = Lutensol AT25, available from BASF.

[0219] 4 = Premix of 85.8wt% palm-based triethanolamine ester quaternary ammonium compound and 14.2wt% C16-18 fatty alcohol.

[0220] 5 = Levenol C201 - Glycerol ester alkoxylate with x+y+z = 17 (as per formula (I)), available from Kao Chemicals.

[0221] The compositions were produced according to the following method: i. The conditioning premix was produced by melting the ingredients and stirring together at 65°C in a first vessel. ii. In a second vessel the demineralized water was added, heated to 45°C and stirred at approximately 140rpm. iii. The encapsulated perfume, non-ionic surfactant, anti-foam, editronic acid and organic acid were added and the mixture mixed until it appeared homogeneous. iv. The conditioning premix was then added to the second vessel. v. The dye was added. vi. The mixture was further mixed for 6 minutes and held at 45°C. vii. The glycerol ester alkoxylate was added. viii. The mixture was mixed and simultaneously reduced in temperature to 37°C. ix. The free oil perfume was added and the mixture mixed for a further minute at 37°C. x. The mixture was cooled at a rate of 1°C per minute to 35°C. xi. Stirring was then stopped and the mixture left to cool to room temperature.

[0222] An alternative process was also trialed, whereby the glycerol ester alkoxylate was added at the very end of the process, i.e. step vii was moved after step x. This is referred to as “end of batch process” in table 6.

[0223] Table 6: performance testing of compositions B and 2

[0224] The viscosity of the compositions was measured at 20°C using an MCR 302 cone and plate rheometer ex. Anton Paar, using a cone and plate geometry (CP-50) with a 2 degree cone angle.

[0225] The following measurements were recorded:

[0226] It can clearly be observed that compositions according to the invention are superior with a significantly greater viscosity when measured at multiple shear rates and time points after the composition was produced. This is in comparison with a composition not according to the invention, where that the sum of x+y+z in the glycerol ester alkoxylate is outside the scope of claim 1.

[0227] It can further be concluded that the alternative process of incorporating the glycerol ester alkoxylate according to the invention at the end of the batch process leads to increased viscosity values.

Claims

CLAIMS1. A fabric conditioner composition comprising: a. 1 to 30 wt.% ester-linked quaternary ammonium compound; b. 0.01 to 5wt.% glycerol ester alkoxylate; and c. 0.1 to 20 wt.% perfume, wherein the glycerol ester alkoxylate is selected from substances of the following formula (I):wherein R1, R2and R3are, independent from each other, selected from linear or branched alkylene groups (CmH2m) with m being 2 or 3 or mixtures thereof; x, y and z are, independent from each other, integer numbers from 0 to 300, where at least one of the variables x, y and z is 1 or an integer number greater than 1 , preferably are, independent from each other, integer numbers from 1 to 250, more preferably from 2 to 200, even more preferably from 5 to 150, particularly preferably from 10 to 120, extraordinarily preferably from 15 to 110 and especially preferably from 20 to 100;R4, R5and R6are, independent from each other, selected from hydrogen, linear or branched, preferably linear, saturated or unsaturated acyl groups comprising from 8 to 30 carbon atoms or mixtures thereof, preferably are, independent from each other, selected from hydrogen, linear or branched, preferably linear, saturated or unsaturated acyl groups comprising from 12 to 30 carbon atoms or mixtures thereof, more preferably are, independent from each other, selected from hydrogen, linear or branched, preferably linear, saturated or unsaturated acyl groups comprising from 12 to 24 carbon atoms or mixtures thereof, even more preferably are,independent from each other, selected from hydrogen, linear or branched, preferably linear, saturated or unsaturated acyl groups comprising from 12 to 20 carbon atoms or mixtures thereof, and particularly preferably are, independent from each other, selected from hydrogen, linear or branched, preferably linear, saturated or unsaturated acyl groups comprising from 14 to 20 carbon atoms or mixtures thereof, and wherein in the definitions of R4, R5and R6above, at least one of R4, R5and R6is an acyl group characterized in that x+y+z is, based on a molar average, a number from 50 to 300, preferably from 60 to 300, more preferably from 70 to 280, even more preferably from 85 to 250 and particularly preferably from 90 to 250; at least 70 mol%, preferably at least 75 mol%, more preferably at least 80 mol% and even more preferably at least 85 mol% of the glycerol ester alkoxylates of the formula (I) in the mixture, in each case based on the total amount of the glycerol ester alkoxylates of the formula (I) in the mixture, are glycerol ester alkoxylates of the formula (I), wherein all of the groups R4, R5and R6are acyl groups; and at least 30 mol%, preferably at least 40 mol%, more preferably at least 50 mol%, even more preferably at least 60 mol% and particularly preferably at least 70 mol% of those groups R4, R5and R6, are linear or branched, preferably linear, saturated or unsaturated acyl groups comprising 16 to 20 carbon atoms or mixtures thereof and preferably are linear or branched, preferably linear, saturated or unsaturated acyl groups comprising 16 to 18 carbon atoms or mixtures thereof, in each case based on the total amount of the linear or branched, preferably linear, saturated or unsaturated acyl groups R4, R5and R6. and wherein the viscosity of the composition is at least 100mPa.s when measured at a shear rate of 20s_1at 20°C using a cone and plate rheometer with a 2 degree cone angle.

2. The fabric conditioner composition according to claim 1 , characterized in that at least 20 mol%, preferably at least 25 mol%, more preferably at least 30 mol%, even more preferably at least 35 mol% and particularly preferably at least 40 mol% of those groups R4, R5and R6, are linear or branched, preferably linear, unsaturated acyl groups comprising 16 to 20 carbon atoms or mixtures thereof and preferably are linear or branched, preferably linear, unsaturated acyl groups comprising 16 to 18 carbon atoms or mixtures thereof, in each case based on the total amount of the acyl groups R4, R5and R6.

3. The fabric conditioner composition according to any preceding claim, characterized in that the groups R4, R5and R6are selected from hydrogen, acyl groups derived from palm oil, rape seed oil, refined rape seed oil, sunflower oil, high oleic sunflower oil, or mixtures thereof.

4. The fabric conditioner composition according to any preceding claim, characterized in that the composition further comprises encapsulated perfume.

5. A method of manufacturing the fabric conditioner composition of any preceding claim, wherein the glycerol ester alkoxylate is added sequentially after the free oil perfume, more preferably directly after the free oil perfume.

6. A method of treating fabrics, wherein a fabric conditioner composition according to any of claims 1-4 is delivered to the fabric in the rinse stage of a laundry process.

7. A use of a fabric conditioner according to any of claims 1 to 4 to provide conditioning to a fabric surface whilst not significantly compromising said fabric’s wettability, wherein a composition as described herein is delivered to the fabric in the rinse stage of a laundry process.

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