The present invention relates to cationic inulin, in particular hydroxypropyltrimonium inulin.

Cationic inulins have been described in WO 96/34017 and WO 98/14482. Quaternary ammonium substituted fructan derivatives have been disclosed in WO 98/14482, wherein mostly inulins derived from chicory with a degree of polymerization of 2 to 60 have been used to produce hydroxypropyltrimonium inulins. Also cationic inulins with a higher DP with a high degree of substitution of cationic groups (DS well above 1) are described. Such high DS cationic inulins are well soluble in water but generally have an unsatisfactory biodegradability.

Cationic inulins are sold by Cosun under the tradename Quatin®, i.e. Quatin® 350, Quatin® 680 and Quatin® 1280. These cationic inulins are beneficially used in several applications, e.g. cosmetic compositions (in WO 2020/207642, EP 3 536 384 and FR 2 795 953), detergent compositions (in EP 3 315 593) and as a pesticide (in WO 2020/25592). There is still a need for improved properties of these cationic inulins in the various applications.

The objective of the present invention is to provide a novel hydroxypropyltrimonium inulin.

The present invention pertains to a hydroxypropyltrimonium inulin wherein at least 90% of the inulin has a degree of polymerization of at least 10, and the degree of substitution with the hydroxypropyltrimonium group is at least 0.31 and at most 0.7. The cationic inulin of the invention has improved coacervation properties compared to conventional cationic inulin having a similar degree of substitution (DS) of cationic groups. It was found that the degree of substitution of the cationic inulin of the invention which is based on longer chain cationic inulin has a coacervation property comparable or even better than conventional cationic inulin with a higher degree of substitution of cationic groups, or even a DS twice as high. Examples of such conventional cationic inulin include Quatin® 1280 and Quatin® 680. Such improved coacervation property is particularly observed in combination with surfactants, particularly anionic surfactants. This renders the inventive cationic inulin suitable for use in cosmetic compositions, and in particular those cosmetic compositions suitable for washing or cleaning. In hair cleaning or conditioning compositions, the inventive inulin enables a reduced or low combing force (through hair) and/or an improved deposition (onto hair), in particular of the cationic inulin of the invention, coacervates thereof and/or insoluble actives such as silicones. The wordings “coacervate” or “coacervation” refer to (the process of creating) an insoluble complex formed between a cationic component, in this case cationic inulin or hydroxypropyltrimonium inulin, and an anionic component such as an anionic surfactant when diluted with water. A coacervate generally contains a high level of cationic charge and is known to deposit the polymer on hair and enhance the adsorption of insoluble actives. The inulin of the invention can be easily processed, no additional handling is necessary for hydration of the cosmetic composition, and the inventive inulin can be easily rinsed off from hair or skin, and hence generally no build up of the cationic inulin of the invention is observed after multiple hair washing treatments. The inventive inulin provides an improved sensoric profile during washing, during drying and after drying of hair, including better flash foam formation, increased creaminess and improved skin feel. The lower degree of substitution allows for an improved biodegradability and/or an improved aquatic toxicity. Moreover, the cationic inulin is a bio-based product. In addition, the hydroxypropyltrimonium inulin of the invention has good film forming properties. The inventive inulin can be used in detergent compositions, and generally reduces spotting and/or filming on hard surfaces such as glass and polymer surfaces. The inventive cationic inulin can furthermore be used as pesticide, fungicide, algaecide, dessicant and/or extending the shelf life of fruits and/or vegetables.

The hydroxypropyltrimonium inulin is an inulin which comprises 2-hydroxypropyl 3- trimethylammonio propyl groups also referred to as hydroxypropyltrimonium groups. The hydroxypropyltrimonium inulin of the invention has a degree of substitution (DS) of the hydroxypropyltrimonium groups of at least 0.31 and at most 0.7. The DS is at least 0.31 to allow for a more homogenous substitution of the hydroxypropyltrimonium groups over the inulin, and therewith ensuring a suitable solubility of the resulting cationic inulin in an aqueous medium. The DS of at most 0.7 is selected to ensure an improved biodegradability compared to the cationic inulin with DS of at least 0.7, while simultaneously having good and improved coacervation properties. Preferably, the DS is at least 0.32, more preferably at least 0.33 and most preferably at least 0.35, and preferably at most 0.68, more preferably at most 0.65, even more preferably at most 0.6, even more preferably at most 0.55 and most preferably at most 0.5. The degree of substitution or DS is defined as the cationic group content, preferably hydroxypropyltrimonium group, per monosaccharide unit. A DS of 0.5 refers to a cationic inulin comprising one cationic group per two monomeric monosaccharide units. The degree of substitution can be determined using methods known in the art. For the purposes of this application, the Kjeldahl method is used to determine the nitrogen content, which is then converted to degree of substitution. The Kjeldahl is well established and well known to the person skilled in the art. In this application the Kjeldahl method is performed by hydrolyzing a sample using H2SO4 at 420°C for 2 hours, during which the proteins will be converted to ammonia. The generated ammonia is distilled off and the amount of nitrogen is measured by titration. The degree of substitution of the hydroxypropyltrimonium groups is calculated using the nitrogen content. The hydroxypropyltrimonium inulin of the invention comprises inulin of which at least 90 wt% has a degree of polymerization of at least 10, based on the total weight of the hydroxypropyltrimonium inulin. Conventional cationic inulins like Quatin® 350, Quatin® 680 and Quatin® 1280 generally have less than 70 wt% of inulin having a degree of polymerization of at least 10. Preferably, the inventive inulin comprises inulin of which at least 95 wt% has a degree of polymerization of at least 10 and most preferably at least 98 wt% has a degree of polymerization of at least 10, based on the total weight of the hydroxypropyltrimonium inulin. Alternatively or additionally, at least 90 wt% of the inulin has a degree of polymerization of at least 11, preferably at least 12 and most preferably at least 13, based on the total weight of the hydroxypropyltrimonium inulin. The degree of polymerization can be determined using methods known in the art. Preferably, the degree of polymerization is determined before the inulin is substituted with cationic groups. Examples of such methods include size exclusion chromatography and HPAEC-PAD (High Performance anion exchange chromatography coupled to pulsed amperometric detection). A preferred method is a method based on HPAEC-PAD.

The wording “inulin” has its conventional meaning and refers to polysaccharides comprising P(2, 1 ) linked fructofuranose units and a glucopyranose unit. Inulin is a natural product and can be obtained from chicory, dahlias and Jerusalem artichokes. Preferably, the inulin is obtained from chicory. Typically, the degree of polymerization of inulin (from chicory) generally ranges from 2 to 60. Commercial cationic inulin such as Quatin® 350 generally have a degree of polymerization ranging from 2 to 60. The cationic inulin of the present invention comprises inulin which at least 90 wt% has a degree of polymerization of at least 10.

In one embodiment, the hydroxypropyltrimonium inulin has an average degree of polymerization of at least 15, preferably at least 18, even more preferably at least 20, and most preferably at least 22, and preferably at most 30, more preferably at most 28 and most preferably at most 25.

In a further embodiment, the hydroxypropyltrimonium inulin comprises at most 1 wt% mono- and/or disaccharides, based on the total weight of the hydroxypropyltrimonium inulin. Preferably, the hydroxypropyltrimonium inulin comprises at most 0.5 wt% mono- and/or disaccharides, more preferably at most 0.2 wt% and most preferably at most 0.1 wt% mono- and/or disaccharides, and preferably at least 0.001 wt%, more preferably at least 0.005 wt% and most preferably at least 0.01 wt% mono- and/or disaccharides, based on the total weight of the hydroxypropyltrimonium inulin. The amount of mono- and/or disaccharide can be determined with methods known in the art. Examples of such methods include refractometry, specific gravity, high performance anion exclusion chromatography and infrared absorption techniques.

In a further embodiment, the hydroxypropyltrimonium inulin comprises at most 10 wt% oligofructose, based on the total weight of the hydroxypropyltrimonium inulin. Preferably, the hydroxypropyltrimonium inulin comprises at most 5 wt% oligofructose, more preferably at most 2 wt% and most preferably at most 1.5 wt% oligofructose, and preferably at least 0.001 wt%, more preferably at least 0.01 wt% and most preferably at least 0.05 wt% oligofructose, based on the total weight of the hydroxypropyltrimonium inulin. The oligofructose is defined as a fructan derivative with a degree of polymerization of between 3 and 10, which are coupled via p(2- 1 ) bonds. The amount of oligofructose can be determined using methods known in the art. Preferably, the degree of polymerization is determined before the inulin is substituted with cationic groups. Examples of such methods include size exclusion chromatography and HPAEC-PAD (High Performance anion exchange chromatography coupled to pulsed amperometric detection). A preferred method is a method based on HPAEC-PAD.

In one embodiment, the hydroxypropyltrimonium inulin comprises at most 10 wt% nonsubstituted inulin, based on the total weight of the hydroxypropyltrimonium inulin. Preferably, the hydroxypropyltrimonium inulin comprises at most 5 wt% non-substituted inulin, more preferably at most 2 wt% and most preferably at most 1 wt% non-substituted inulin, and preferably at least 0.001 wt%, more preferably at least 0.005 wt% and most preferably at least 0.01 wt% non-substituted inulin, based on the total weight of the hydroxypropyltrimonium inulin. With “non-substituted inulin” is meant inulin which has not been substituted with cationic groups, particularly with hydroxypropyltrimonium groups. Nonsubstituted inulin generally has a low aqueous solubility and do not contribute to the favourable properties of the cationic inulin of the invention.

In one embodiment, the hydroxypropyltrimonium inulin has a solubility in water at 25°C of at least 15 wt%. Preferably, the solubilty is at least 20 wt%, more preferably at least 30 wt%, even more preferably at least 50 wt%, even more preferably at least 60 wt% and most preferably at least 70 wt%, and preferably at most 100 wt%, more preferably at most 99 wt%, even more preferably at most 98 wt% and most preferably at most 95 wt%. The term “solubility” is defined as the maximum percentage (by weight) of a substance that will dissolve in a unit of volume of water at a certain temperature.

The innovative inulin can be in any form including liquids such as solutions and emulsions and solids such as powders, flakes and granules. In one embodiment, the moisture content of the inulin is at most 10 wt%, based on the total weight of the hydroxypropyltrimonium inulin. Preferably, the inulin comprises at most 7 wt% moisture, more preferably at most 6 wt% arabinose and most preferably at most 5 wt% moisture, and preferably at least 0.001 wt% moisture, more preferably at least 0.01 wt% moisture and most preferably at least 0.1 wt% moisture, based on the total weight of the hydroxypropyltrimonium inulin.

The invention further pertains to fructan derivative comprising a cationic group of the formula:

-A-N ⁺ R ¹ R ² R ³ or -C(=NR ⁴ )-NR ¹ R ² in which

A represents a straight or branched C2-C6 alkylene group which is optionally preceded by a carbonyl group or optionally interrupted by one or two oxygen atoms or imino or alkylamino groups and optionally substituted by one or two hydroxyl groups or amine groups or a carboxyl or carbamoyl group; or A represents the residue of a monosaccharide unit;

R ¹ and R ² each represent hydrogen methyl, carboxymethyl, phosphonomethyl, ethyl, hydroxyethyl, propyl, isopropyl, allyl, hydroxypropyl or dihydroxypropyl or, together with the nitrogen atom, from a pyrrolidino, piperidino, piperazino, N’-alkylpiperazino, N’- (hydroxyalkyl)piperazino, N’(aminoalkyl)piperazino, morpholino or hexamethyleneamino group;

R ³ represents hydrogen, C1-C18 alkyl, C3-C18 alkenyl, alkynyl or cycloalkyl, C4-C18 cycloalkylalkyl or C7-C18 aralkyl or a group of the formula -A-Fruc, where A has the above- mentioned meaning and Fruc represents fructan residue bonded via oxygen; and R ⁴ represents hydrogen, methyl, ethyl, hydroxyethyl, hydroxypropyl or dihydroxypropyl; where the amine nitrogen atoms can be uncharged or protonated or quaternised with methyl ethyl, hydroxyethyl, hydroxypropyl or dihydroxypropyl, wherein the at least 90% of the fructan derivative has a degree of polymerization of at least 10, and the degree of substitution with the cationic group is at least 0.31 and at most 0.7. The fructan derivative of the invention generally provides similar advantages and embodiments as the hydroxypropyltrimonium inulin described above. Most preferred is the hydroxypropyltrimonium inulin described above.

The hydroxypropyltrimonium inulin can be produced by reacting inulin and 3-chloro-2- hydroxypropyl trimethyl ammonium (CHPTA) in the desired amounts to obtain the hydroxypropyltrimonium inulin of the invention. For the fructan derivative described above a similar inulin can be used to react with a wide variety of components. Further details of the production of the fructan derivative and the hydroxypropyltrimonium inulin can be gleaned from WO 98/14482. The inulin that can be suitably used in the process of the invention is an inulin which is obtained by low temperature crystallization. Further details can be found in WO 96/01849. Such inulins are also sold by Cosun under the tradename Fruitafit® TEX.

The invention further pertains to a cosmetic composition comprising the hydroxypropyltrimonium inulin of the invention and a cosmetic excipient. The cosmetic composition can be any cosmetic composition known in the art. The cosmetic compositions of the invention include compositions that are intended to be placed in contact with portions of the human body (skin, hair, nails, mucosa, etc.) or with teeth and the mucous membranes of the oral cavity with a view exclusively or mainly to cleaning them, perfuming them, changing their appearance, protecting them, keeping them in good condition or modifying odors, and skin care, sun care, hair care or nail care applications. Preferred cosmetic compositions are hair care products. Examples of such hair care products include shampoos, hair conditioners, hair damage repairing products, hair color protecting products, hair coloring products, after-shampoos, two-in-one products, hair lotions or skin care products such as soaps, hand soaps and body washes.

The cosmetic composition comprises the hydroxypropyltrimonium inulin of the invention. In one embodiment, the cosmetic composition may comprise the hydroxypropyltrimonium inulin in an amount of at most 90 % by weight (wt%), based on the total weight of the cosmetic composition. Preferably, the hydroxypropyltrimonium inulin is present in an amount of at most 70 wt%, more preferably at most 50 wt%, even more preferably at most 40 wt% and most preferably at most 30 wt%, and preferably at least 0.01 wt%, more preferably at least 0.05 wt%, even more preferably at least 0.1 wt% and most preferably at least 0.5 wt%, based on the total weight of the cosmetic composition.

The cosmetic composition comprises a cosmetic excipient. The cosmetic excipient can be any excipient known in the art that can be suitably used in cosmetic compositions. Examples of such cosmetic excipients include surfactants, solvents, fragrances, color additives, pigments, humectants, emollients, vitamins and provitamins, salts, foam boosters, solubilizers, anti-oxidants, pH adjusting agents, sequestering agents, viscosity modifiers, anti-dandruff agents, seborrhoeic agents, preservation agents, and agents that prevent hair loss and/or promoting hair (re)growth. It is contemplated to use two or more cosmetic excipients.

In one embodiment, the cosmetic composition may comprise the cosmetic excipient in an amount of at most 90 % by weight (wt%), based on the total weight of the cosmetic composition. Preferably, the cosmetic excipient is present in an amount of at most 70 wt%, more preferably at most 50 wt%, even more preferably at most 40 wt% and most preferably at most 30 wt%, and preferably at least 0.01 wt%, more preferably at least 0.05 wt%, even more preferably at least 0.1 wt% and most preferably at least 0.5 wt%, based on the total weight of the cosmetic composition.

In one embodiment, the cosmetic excipient is a surfactant. The surfactant can be any surfactant known in the art. Examples of such surfactants include anionic, cationic, non-ionic and amphoteric surfactants. Preferably, the cosmetic excipient is an anionic surfactant. An anionic surfactant is defined as a surfactant comprising at least one anionic functional group. Examples of anionic surfactants include alkyl sulfates such as ammonium lauryl sulfate, and sodium lauryl sulfates (SLS) or sodium dodecyl sulfate (SDS); alkyl ether sulfates such as sodium lauryl ether sulfate (SLES) and sodium myreth sulfate; alkyl benzene sulfonates such as sodium linear alkyl benzene sulfonate; alkyl ester sulfonates such as methyl ester sulfonate (MES) and alfa olefin sulfonate (AOS); alkyl carboxylates such as sodium stearate and sodium lauroyl sarcosinate; and alkyl-aryl phosphates. It is contemplated to use two or more anionic surfactants in the cosmetic composition of the invention. It is further envisaged to use a combination of an anionic surfactant and a second surfactant, wherein the second surfactant is preferably selected from an amphoteric surfactant, a cationic surfactant and a non-ionic surfactant.

In one embodiment, the cosmetic composition may comprise the surfactant, preferably the anionic surfactant in an amount of at most 90 % by weight (wt%), based on the total weight of the cosmetic composition. Preferably, the surfactant, preferably the anionic surfactant, is present in an amount of at most 70 wt%, more preferably at most 50 wt%, even more preferably at most 40 wt% and most preferably at most 30 wt%, and preferably at least 0.01 wt%, more preferably at least 0.05 wt%, even more preferably at least 0.1 wt% and most preferably at least 0.5 wt%, based on the total weight of the cosmetic composition.

In one embodiment, the molar ratio between the cosmetic excipient, preferably the anionic surfactant, and the hydroxypropyltrimonium inulin is at least 0.01. Preferably, the ratio is at least 0.05, more preferably at least 0.1 , even more preferably at least 0.2, even more preferably at least 0.5, and most preferably at least 1 , and preferably at most 100, more preferably at most 75, even more preferably at most 50, even more preferably at most 40, even more preferably at most 20, even more preferably at most 10 and most preferably at most 5.

In one embodiment, the weight ratio between the cosmetic excipient, preferably the anionic surfactant, and the hydroxypropyltrimonium inulin is at least 0.01. Preferably, the ratio is at least 1, more preferably at least 2, even more preferably at least 5, even more preferably at least 10, and most preferably at least 20, and preferably at most 100, more preferably at most 90, even more preferably at most 80, even more preferably at most 70, even more preferably at most 60, even more preferably at most 50 and most preferably at most 40.

The cosmetic composition may further comprise a solvent. The solvent may be any solvent suitable for use in cosmetic compositions. Examples of such solvents include water, ethanol, propanol, isopropanol, acetone, methoxyethanol, diethylene glycol, propylene glycol and dipropylene glycol. It is contemplated to use two or more solvents. The most preferred solvent is water.

In one embodiment, the cosmetic composition may comprise the solvent, preferably water, in an amount of at most 90 % by weight (wt%), based on the total weight of the cosmetic composition. Preferably, the solvent, preferably water, is present in an amount of at most 70 wt%, more preferably at most 50 wt%, even more preferably at most 40 wt% and most preferably at most 30 wt%, and preferably at least 0.01 wt%, more preferably at least 0.05 wt%, even more preferably at least 0.1 wt% and most preferably at least 0.5 wt%, based on the total weight of the cosmetic composition.

The remaining part of the cosmetic composition may be comprised of other components commonly used in cosmetic compositions. With the hydroxypropyltrimonium inulin, surfactant and water, the other components add up to 100 wt% of the total weight of the cosmetic composition.

The invention further pertains to a detergent composition comprising the hydroxypropyltrimonium inulin of the invention and a surfactant. The detergent composition can be any detergent composition known in the art. Examples of such detergent compositions include laundry detergent and dish detergent. Preferably, the detergent composition is a dish detergent or an automatic dishwashing detergent.

The detergent composition comprises the hydroxypropyltrimonium inulin of the invention. In one embodiment, the detergent composition may comprise the hydroxypropyltrimonium inulin in an amount of at most 5 % by weight (wt%), based on the total weight of the detergent composition. Preferably, the hydroxypropyltrimonium inulin is present in an amount of at most 2 wt%, more preferably at most 1.5 wt%, even more preferably at most 1 wt% and most preferably at most 0.5 wt%, and preferably at least 0.01 wt%, more preferably at least 0.02 wt%, even more preferably at least 0.05 wt% and most preferably at least 0.1 wt%, based on the total weight of the detergent composition.

In a further embodiment, the detergent composition is a concentrate or concentrated detergent composition comprising hydroxypropyltrimonium inulin in an amount of at most 50 wt%, based on the total weight of the detergent composition. Preferably, the hydroxypropyltrimonium inulin is present in an amount of at most 40 wt%, more preferably at most 35 wt%, even more preferably at most 30 wt% and most preferably at most 25 wt%, and preferably at least 0.1 wt%, more preferably at least 0.2 wt%, even more preferably at least 0.5 wt% and most preferably at least 1 wt%, based on the total weight of the detergent composition.

In one embodiment, the detergent composition comprises a surfactant. The surfactant can be any surfactant known in the art. Examples of such surfactants include anionic, cationic, non-ionic and amphoteric surfactants. Examples of anionic surfactants include alkyl sulfates such as ammonium lauryl sulfate, and sodium lauryl sulfates (SLS) or sodium dodecyl sulfate (SDS); alkyl ether sulfates such as sodium lauryl ether sulfate (SLES) and sodium myreth sulfate; alkyl benzene sulfonates such as sodium linear alkyl benzene sulfonate; alkyl ester sulfonates such as methyl ester sulfonate (MES) and alfa olefin sulfonate (AOS); alkyl carboxylates such as sodium stearate, sodium N-lauroyl glutamate, sodium lauroyl sarcosinate and sodium myristoyl sarcosinate; and alkyl-aryl phosphates.

Examples of cationic surfactants include quaternary ammonium compounds such as cetyl trimethylammonium bromide (CTAB), benzalkonium chloride (BAG), didecyldimethyl ammonium chloride (DDAC), dimethyldioctadecylammonium chloride, dimethyldioctadecylammonium bromide (DODAB), 1,2-dioleoyl-3-trimethylammonium propane (DOTAP), dimethyldodecylbenzyl ammonium bromide, benzethonium chloride (BZT), cetalkonium chloride (CKC), stearalkonium chloride and thonzonium bromide.

Examples of non-ionic surfactants include ethoxylates such as octaethylene glycol monododecyl ether, pentaethylene glycol monododecyl ether and polyethylene glycol nonyl phenyl ether; ethoxylated amines such as polyethoxylated tallow amine, cocamide monoethanolamine and cocamide diethanolamine; poloxamer; and fatty acid esters such as glycerol monostearate, glycerol monolaurate, sorbitan monolaurate, sorbitan monostearate, soribitan tristearate, decyl glucoside, lauryl glucoside and octyl glucoside.

Examples of amphoteric surfactants include sulfonates such as sultaines CHAPS and cocamidopropyl hydroxysultaine; betaines such as cocamidopropyl betaine; and amine oxides such as lauryldimethylamine oxide and myristamine oxide.

Amino acid surfactants are also contemplated. Examples of such amino acid surfactants include N’-acyl-arginine-methyl ester hydrochloride, amino acid glyceride conjugates and dilauroylated derivative of glutamine.

It is contemplated to use two or more surfactants in the detergent composition of the invention. In one embodiment, the detergent composition may comprise the surfactant, preferably the anionic surfactant in an amount of at most 90 % by weight (wt%), based on the total weight of the detergent composition. Preferably, the surfactant, preferably the anionic surfactant, is present in an amount of at most 70 wt%, more preferably at most 50 wt%, even more preferably at most 40 wt% and most preferably at most 30 wt%, and preferably at least 0.01 wt%, more preferably at least 0.05 wt%, even more preferably at least 0.1 wt% and most preferably at least 0.5 wt%, based on the total weight of the detergent composition.

In one embodiment, the molar ratio between the surfactant and the hydroxypropyltrimonium inulin is at least 0.01. Preferably, the ratio is at least 0.05, more preferably at least 0.1 , even more preferably at least 0.2, even more preferably at least 0.5, and most preferably at least 1 , and preferably at most 100, more preferably at most 75, even more preferably at most 50, even more preferably at most 40, even more preferably at most 20, even more preferably at most 10 and most preferably at most 5.

In one embodiment, the weight ratio between the surfactant and the hydroxypropyltrimonium inulin is at least 0.01. Preferably, the ratio is at least 1 , more preferably at least 2, even more preferably at least 5, even more preferably at least 10, and most preferably at least 20, and preferably at most 100, more preferably at most 90, even more preferably at most 80, even more preferably at most 70, even more preferably at most 60, even more preferably at most 50 and most preferably at most 40.

The detergent composition may further comprise a second excipient known in the art that can be suitably used in detergent compositions. Examples of such second excipients include builders, bleaching agents, bleach activators, bleach catalysts, dyes, polymers, corrosion inhibitors, complexing agents, anti-redeposition agents, perfumes, process aids and enzymes. It is contemplated to use two or more second excipients.

In one embodiment, the detergent composition may comprise the second excipient in an amount of at most 90 % by weight (wt%), based on the total weight of the detergent composition. Preferably, the second excipient is present in an amount of at most 70 wt%, more preferably at most 50 wt%, even more preferably at most 40 wt% and most preferably at most 30 wt%, and preferably at least 0.01 wt%, more preferably at least 0.05 wt%, even more preferably at least 0.1 wt% and most preferably at least 0.5 wt%, based on the total weight of the detergent composition.

The remaining part of the detergent composition may be comprised of other components commonly used in detergent compositions. With the hydroxypropyltrimonium inulin and surfactant, the other components add up to 100 wt% of the total weight of the cosmetic composition.

The invention further pertains to the use of the hydroxypropyltrimonium inulin of the invention as a pesticide, fungicide, algaecide, dessicant and/or extending the shelf life of fruits and/or vegetables. Alternatively, the invention pertains to a hydroxypropyltrimonium inulin wherein at least 90% of the inulin has a degree of polymerization of at least 10, and the degree of substitution with the hydroxypropyltrimonium group is at least 0.31 and at most 0.7, for use as a pesticide, fungicide, algaecide, dessicant and/or extending the shelf life of fruits and/or vegetables. In a preferred embodiment, the inulin of the invention is used as a fungicide, in particular its use to control Ascomycota, and even more preferably to control powdery mildew.

The invention further pertains to an agrochemical composition comprising a hydroxypropyltrimonium inulin wherein at least 90% of the inulin has a degree of polymerization of at least 10, and the degree of substitution with the hydroxypropyltrimonium group is at least 0.31 and at most 0.7.

The agrochemical composition of the invention can be in any form or formulation known in the art. Examples of such formulations include solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine capsules in polymeric substances in coating compositions of seed, and also ULV cold- and warm-fogging formulations. These formulations are produced in a known matter.

In one embodiment, the agrochemical composition may comprise the hydroxypropyltrimonium inulin in an amount of at most 5 % by weight (wt%), based on the total weight of the agrochemical composition. Preferably, the hydroxypropyltrimonium inulin is present in an amount of at most 2 wt%, more preferably at most 1.5 wt%, even more preferably at most 1.2 wt% and most preferably at most 1 wt%, and preferably at least 0.01 wt%, more preferably at least 0.05 wt%, even more preferably at least 0.1 wt% and most preferably at least 0.2 wt%, based on the total weight of the agrochemical composition.

The hydroxypropyltrimonium inulin of the invention can be used in a wide range of applications. The invention pertains to the use of the hydroxypropyltrimonium inulin in paints, construction applications, textiles e.g. fiber treatment, leather lubrication, household care compositions, softening, fabric care in laundry applications, healthcare applications, release agents, water-based coatings, personal care or cosmetic applications, emulsion polymerizations, carpeting, automobile parts, window frames, kitchen worktops, container closures, lunch boxes, closures, medical devices, household articles, food containers, dishwashers, outdoor furniture, blow-molded bottles, disposable non-woven fabrics, cables and wires, packaging, coil coating applications, can coatings, car refinish, mining, oil drilling, fuel additive and automotive applications. Each of these uses is separately contemplated and is meant to be explicitly and individually disclosed.

The invention is exemplified in the following Examples.

Examples

Example 1 : hydroxypropyltrimonium inulin (DS of 0.31)

90 g 3-chloro-2-hydroxypropyl-trimethylammonium chloride (CHPTA) is dissolved in 470 ml demineralized water. Subsequently, 130 g of inulin having 95% of the inulin with a degree of polymerization of at least 10 is added to the solution over a period of 15 minutes while stirring the solution. The resulting solution is heated to 45°C while adding 49 g of a 50 wt% aqueous sodium hydroxide solution and maintained at 45 °C for 3 hours. The solution is subsequently heated to 75°C and kept at 75°C for 90 minutes. The resulting solution is cooled to room temperature and the pH is adjusted to between 5 and 5.5 using a 6 M hydrogen chloride solution. The average degree of substitution of hydroxypropyltrimonium groups was determined to be 0.31 using the Kjeldahl method.

Example 2: hydroxypropyltrimonium inulin (DS of 0.68)

230 g 3-chloro-2-hydroxypropyl-trimethylammonium chloride (CHPTA) is dissolved in 350 ml demineralized water. Subsequently, 130 g of inulin having 95% of the inulin with a degree of polymerization of at least 10 is added to the solution over a period of 15 minutes while stirring the solution. The resulting solution is heated to 45°C while adding 49 g of a 50 wt% aqueous sodium hydroxide solution and maintained at 45 °C for 3 hours. The solution is subsequently heated to 75°C and kept at 75°C for 90 minutes. The resulting soliution is cooled to room temperature and the pH is adjusted to between 5 and 5.5 using a 6 M hydrogen chloride solution. The average degree of substitution of hydroxypropyltrimonium groups was determined to be 0.68 using the Kjeldahl method.

Example 3: Shampoo and coacervation behaviour

A shampoo is prepared according to Table 1 using the following steps:

1. Add the components in the indicated order (stir until homogeneity).

2. Adjust the pH to 4.5 - 5.0 by using citric acid.

3. Add Sodium Chloride using the above concentrations. Table 1: Basic shampoo composition

The resulting transparent shampoos were diluted with water in separate transparent cups according to the dilution sequence as tabulated in Table 2.

Table 2: Dilution of the basic shampoos The shampoo becomes a milky suspension as the coacervate turns into an insoluble complex and flocculates. The shampoo of Comparative Example A reveals non-transparent milky suspensions in cups 4 to 8 and somewhat less non-transparent milky suspensions in cups 9 and 10. The shampoo of Example 3 reveals non-transparent milky suspensions in cups 3 to 10 and somewhat less non-transparent milky suspensions in cups 2 and 11. These results show that the shampoo in according with the invention has better coacervation properties than the shampoo of Comparative Example A.

Example 4: Shampoo and coacervation behaviour

Similar shampoos were prepared as in Example 3 except that sodium lauroyl sarcosinate (Pureact LSR) is used instead of sodium laureth ether sulfate. The shampoo according to the invention is referred to as Example 4 and the shampoo of Comparative Example B comprises Quatin® 680. The shampoo of Comparative Example B reveals non-transparent milky suspensions in cups 9 to 10 and somewhat less non-transparent milky suspensions in cups 8, 11 and 12. The shampoo of Example 4 reveals non-transparent milky suspensions in cups 5 to 10 and somewhat less non-transparent milky suspensions in cups 1 to 4, 11 and 12. These results show that the shampoo in according with the invention has better coacervation properties than the shampoo of Comparative Example B.

Example 5: Hair properties

A shampoo is prepared according to Table 3 using the following steps:

1. Add the components in the indicated order (stir until homogeneity).

2. Adjust the pH to 4.5 - 5.0 by using citric acid.

3. Add Sodium Chloride using the above concentrations.

Table 3: Basic shampoo composition

60 volunteers with slightly punished hair washed their hair for a week with the control shampoo. During the experiment, one half of the hair was treated with the control shampoo (i.e “Control”) and the other half was treated with the shampoo comprising cationic inulin. Three groups of 20 volunteers were treated with shampoo containing Quatin 350 (Comparative Example B), shampoo containing Quatin 680 (Comparative Example C) and shampoo containing the cationic inulin of Example 1 (Example 5). During treatment, the test parameters were assessed by an experienced hair stylist (expert grading) consecutively. The assessment was done using a 5-point classification scale comparable to school marks (1 : "insufficient" to 5: "very good") with the possibility to assign half marks. In the Table below the test parameters are shown as differences with the Control.

Table 4: Test parameters of Comparative Examples B and C and Example 5 From Table 4 it can be deduced that the overall performance is better for the shampoo of Example 5 compared to the shampoos of Comparative Examples B and C. All shampoos comprising cationic inulin perform better than the control shampoo.