Cationic galactomannans from GUAR and its process of production

Abstract

The present invention relates to a cationic galactomannan derived from guar gum and having a mannose / galactose molar ratio within the range of 2.5:1 and 5:1, a production process thereof and its performance and use in home and personal care formulations.

Description

[0001] CATIONIC GALACTOMANNANS FROM GUAR AND ITS PROCESS OF PRODUCTION

[0002] RELATED APPLICATION

[0003] This application claims priority of EP patent application 24315010.9 filed on January 12, 2024, the whole content of each of these applications being incorporated herein by reference for all purposes.

[0004] FIELD OF THE INVENTION

[0005] The present invention concerns cationic galactomannans obtained from guar gum, a process of production of such cationic galactomannans and performance properties, such as conditioner, for home and personal care applications.

[0006] TECHNICAL BACKGROUND

[0007] Galactomannans are polysaccharides consisting of a mannose backbone with galactose side groups which can be obtained from a number of Leguminosae. Cationic galactomannans are commonly used in personal care products like hair or skin. Mention can be made to US 2008 / 0112907, US 2003 / 0211952 or WO 2013 / 011122.

[0008] Cationically modified galactomannans derived from tara gum have improved conditioning properties in home and personal care products, notably products rinsed from hair and body, if compared to cationically modified galactomannans derived from guar gum, according to JP2006241330.

[0009] There is a continuous increase in the interest of better personal care products worldwide.

[0010] Guar is a polysaccharide composed of galactose and mannose as elementary sugar units. The backbone is a linear chain of P-l,4-linked mannose residues to which galactose residues are a-l,6-linked at every other mannose on average, forming short side units. Differently, tara gum is a natural additive, obtained by grinding the endosperm of the seeds of Caesalpinia spinosa. of the Leguminosae family. Structurally, it is a galactomannan polymer consisting of a main chain of P-l,4-linked mannose units with side chains of a-l,6-linked galactose approximately every third mannose unit.

[0011] In the same way, galactomannans derived from locust bean and cassia consist in a polymer having main chain of P-l,4-linked mannose units with side chains of a-1,6- linked galactose approximately every forth mannose unit and every fifth mannose unit, respectively.

[0012] However, the main drawbacks concerning tara gum use is due to the difficulty in obtaining the raw material since the latter comes from tall trees rather than bushes, which limits its wide use due to high cost, with the additional disadvantage of lower annual yields as supply trees also only grow in specific regions.

[0013] The management of galactose content in galactomannans can be modified to a certain extent by using galactosidase enzymes able to remove inherently linked galactose units from the backbone, as is described in the US patent 5,234,825.

[0014] However, such a process has some disadvantages mainly due to the difficulty in obtaining correct and broad access of the enzyme to all portions of the guar, due to its viscosity, which in the end will profoundly affect the mannose / galactose molar ratio. Furthermore, this ratio may also be affected by incomplete removal of residual galactose cleaved during the enzymatic reaction.

[0015] At the end, the residual galactose may be particularly relevant, notably when a cationization is implemented, as any residual galactose may be also cationized, impacting the final performance of cationic galactomannan.

[0016] In view of the above, there is a need to develop a method able to prepare cationic transformed galactomannans structurally similar to cationic galactomannans derived from other Leguminosae as raw material, notably natural tara gum, having good conditioning properties to be used in home and personal care compositions, cost effective preparation and thus widespread use. SUMMARY OF THE INVENTION

[0017] Pursuing research in this field, the Applicant has now developed a method of preparing an original cationic galactomannan having a precisely controlled mannose / galactose ratio similar to galactomannans from other Leguminosae but derived from guar gum using a cost effective and simple enzymatic process.

[0018] The present invention is thus, based on a cationic galactomannan comprising a mannose / galactose molar ratio within the range of 2.5 : 1 to 5 : 1 , wherein the cationic galactomannan is derived from guar gum.

[0019] Preferably, the cationic galactomannan comprises a mannose / galactose ratio from 2.5: 1 to 3.5: 1.

[0020] Furthermore, the present invention also aims to provide a process for preparing said cationic galactomannans with a precise control of the mannose / galactose ratio.

[0021] In particular, according to the invention, in a first production process step guar gum is submitted to a reaction with at least one enzyme to obtain a modified galactomannan having a controlled ratio of mannose / galactose and in a second step the modified galactomannan reacts with at least one cationic agent.

[0022] It has been demonstrated that by using the process of this invention, is not only possible to control the mannose / galactose ratio of the cationic galactomannan but also the degree of substitution (DS) and the molecular weight (Mw) of such cationic galactomannans can be controlled.

[0023] Advantageously, the cationic galactomannans with a controlled mannose / galactose ratio have not only excellent performance in personal care compositions but also high biodegradability.

[0024] Then, the present invention also concerns the use of said cationic galactomannans with a controlled mannose / galactose ratio, as conditioners, stabilizers, thickeners, film formers, surface modifiers, emulsifiers, deposition aids, rheology modifiers and flocculants. Finally, the present invention also refers to a composition, preferably a home and personal care composition, comprising at least one cationic galactomannan according to the invention.

[0025] DETAILED DESCRIPTION OF THE INVENTION

[0026] Definitions:

[0027] Throughout the description, including the claims, the term "comprising one" or “comprising a" should be understood as being synonymous with the term "comprising at least one", unless otherwise specified, "between" and “from... to...” should be understood as being inclusive of the limits.

[0028] As used herein, the term "average" refers to number average unless indicated otherwise.

[0029] As used herein, “weight percent,” “wt%,” “percent by weight,” “% by weight,” and variations thereof refer to the concentration of a substance as the weight of that substance divided by the total weight of the composition and multiplied by 100.

[0030] Throughout this application, including the claims, the term “average” refers to number average unless indicated otherwise.

[0031] Throughout the description, including the claims, all process terms should be understood as being synonymous with the term method.

[0032] It is specified that, in the continuation of the description, unless otherwise indicated, the values at the limits are included in the ranges of values which are given.

[0033] Should the disclosure of any patents, patent applications, and publications which are incorporated herein by reference conflict with the description of the present application to the extent that it may render a term unclear, the present description shall take precedence.

[0034] The present invention refers to cationic galactomannan comprising a mannose / galactose molar ratio within the range of 2.5: 1 and 5: 1, wherein the cationic galactomannan is derived from guar gum.

[0035] As used herein, the term "cationic groups" refers to positively charged groups and to partially charged groups. As used herein, the expression "partially charged groups" designates groups which may become positively charged depending on the pH of the formulation. Such groups may also be named "potentially cationic groups". As used herein, the term "cationic" means at least partially cationic. Thus, the terms "cationizing agents", "cationic groups" and "cationic moieties" include ammoniums (which have a positive charge) but also primary, secondary and tertiary amines and their precursors (which can lead to positively charged compounds).

[0036] In a preferred embodiment, the mannose / galactose ratio is of 2.5 : 1 and 3.5:1. Particularly, the mannose / galactose ratio of the cationic galactomannan of the invention is on average 3: 1.

[0037] As used herein, the ratio mannose / galactose refers to the molar ratio mannose / galactose present in the modified galactomannan or in the cationic galactomannan of the invention.

[0038] The measurement of the ratio mannose / galactose of the modified galactomannan of the invention may be made by1H NMR spectroscopy.

[0039] Once the 'H NMR spectrum is obtained, the integration of the multiplet of signals corresponding to the cleaved mannose anomeric proton, calibrated at 5.2 ppm, is normalized to 1 unity. Other 3 integrated signals of interest, the one corresponding to the anomeric proton of cleaved galactose, is usually between 5.30 and 5.29 ppm. Another signal, the one corresponding to the anomeric proton of linked mannose is usually around 4.89 ppm. The last signal of interest is usually around 4.61 and 4.60 ppm and corresponds to the anomeric proton of linked galactose.

[0040] Therefore, the ratio mannose / galactose can be calculated as follows:

[0041] I (Gl) + l (G2)

[0042] Molar ratio galactose : mannose = The cationic galactomannan of the invention has desired cationicity, conditioning performance whilst maintaining good biodegradability.

[0043] Typically, the cationicity of the cationic galactomannan can be expressed in terms of degree of substitution (DS).

[0044] The cationic degree of substitution may be determined before or after an acidic methanol extraction. The acidic methanol extraction may be considered as a washing step, allowing the removal of the other quaternary ammonium compounds present at the end of the reaction, being the residual cationizing reagent or by-products of unreacted cationizing agent.

[0045] In general, the cationic degree of substitution after acidic methanol extraction (DScat)extraction is lower than the cationic degree of substitution before said extraction (DS cat). In the present invention, the cationic degree of substitution determined after the acidic methanol extraction (DScat)extractionis more precise.

[0046] As used herein, the (DScat) or (D Scationic ) relates to the cationic degree of substitution measured before the acidic methanol extraction.

[0047] As used herein, the (DScat)extraction or (DScationic)extr action relates to the cationic degree of substitution measured after the acidic methanol extraction.

[0048] As used herein, the expression "cationic degree of substitution" (DScat) or (D Sc at) extraction means the average number of moles of cationic groups per mole of sugar unit. The (DScat) Or (DScat) extraction may be measured by means ofJH NMR.

[0049] Once theJH NMR spectrum is obtained, the integration of the multiplet of peaks corresponding to the anomeric proton of sugars usually between 5.4-4.4 ppm, is normalized to unity. The peak of interest, the one corresponding to the methyl protons of the quaternary ammonium group on cationic galactomannan, is centered around 3.1-3.2 ppm. This peak is integrated for 9 protons given that there are 3 methyl groups on the nitrogen atom to reach the ammonium function. Therefore the calculation of the (DScationic) for the case of the cationizing agent 2,3-epoxypropyltrimethylammonium chloride is as follows:

[0050] The measurement of the degree of cationic substitution was made before (DScationic) and after an extraction procedure (DScat)extraction. The true value of degree of cationic substitution is thus considered to be that measured after removal of cationic impurities.

[0051] In general, the cationic degree of substitution of the cationic galactomannans of the present invention may be determined before or after an extraction step. In certain embodiments, the extraction step is done by an acidic methanol extraction step. The ratio of methanol to acid, preferably concentrated HC1 having about 37% acid v / v, can be about 25: 1 to 100: 1, preferably about 50: 1. Further, in certain embodiments, the acidic methanol extraction step can be considered as a washing step that may remove other quaternary ammonium compounds that may be present at the end of the cationizing reaction, including but not limited to residual cationizing agent(s), by-products of any unreacted cationizing agent(s), or mixtures thereof.

[0052] The extraction step can be done in a variety of ways. As noted above, in certain embodiments, the extraction step may be carried out in acidified methanol (50: 1, MeOH / HQconcentrated 37%, v / v). Additionally, the cationic galactomannan can be to the acidic methanol in a concentration equivalent to approximately 1%, under stirring. After adding the acid methanol to the cationic galactomannan, the combination is then brought to reflux temperatures and can be held at the reflux temperature for about 45 minutes. At the end of this extraction step, the acidic methanol can be decanted and the process can be repeated. In certain embodiments, the extraction step comprises one to three, preferably three, serial steps of adding the acidic methanol to the cationic galactomannan and bringing the combination to reflux for the prescribed period of time, in which after each intermediary step the acidic methanol is removed and replaced with fresh acidic methanol. After the extraction step is fully complete, the cationic galactomannan can be filtered and washed with pure methanol, ethanol, or another suitable solvent. The so purified cationic galactomannan is then dried and ground beforeJH NMR analysis.

[0053] According to one embodiment of the invention, the cationic galactomannan has a cationic degree of substitution (DScat)extraction for cationic substituent groups ranging from 0.01 to 1.0.

[0054] In a preferred embodiment, the cationic galactomannan has a cationic degree of substitution (DScat)extraction for cationic substituent groups ranging from 0.01 to 0.4.

[0055] In a more preferred embodiment, the cationic galactomannan has a cationic degree of substitution (DScat)extraction for cationic substituent groups ranging from 0.05 to 0.2.

[0056] The cationicity of the cationic galactomannan may also be expressed in terms of charge density. The cationic degree of substitution may be converted to a charge density through several methods.

[0057] The preferred method for calculating charge density of cationic galactomannan uses a method that specifically quantifies the equivalents of quaternary ammonium groups on said galactomannan. For cationic galactomannans obtained by reacting a galactomannan with 3 -chi oro-2 -hydroxypropyltrimethylammonium chloride or 2,3- epoxypropyltrimethylammonium chloride, the cationic charge density may be calculated from the cationic degree of substitution using the following equation:

[0058] Cationic charge density in mequivalents per gram (meq / g) =

[0059] In general, the equation above depends on the group which is grafted to the galactomannan.

[0060] As used herein, the term "charge density" refers to the ratio of positive charges on a monomeric unit of which a polymer is comprised to the molecular weight of said monomeric unit. The charge density multiplied by the polymer molecular weight determines the number of positively charged sites on a given polymer chain.

[0061] According to the present invention, the cationic galactomannan has a charge density after the acidic methanol extraction from about 0.06 to about 3.2 meq / g, for example from about 0.06 to about 1.8 meq / g, and for example from 0.06 to 1.2 meq / g.

[0062] As for the average molecular weight (Mw) of cationic galactomannans of the present invention, in general the cationic galactomannans can have an average molecular weight (Mw) at least about 10,000 Da. The cationic galactomannans of the present invention can also generally have an average molecular weight (Mw) up to about 2,500 kDa. In a preferred embodiment, the cationic galactomannans of the invention may have an average molecular weight (Mw) higher than about 200,000 Da and more preferably higher than 600,000 Da.

[0063] In still another preferred embodiment, the average molecular weight of the cationic galactomannan herein is lower than about 2,500 kDa more preferably lower than 1,900 kDa.

[0064] According to a particular preferred embodiment, the average molecular weight of said cationic galactomannan is comprised from 600 kDa to about 1,900 kDa.

[0065] As used herein, the "average molecular weight" of the cationic galactomannan means the weight average molecular mass of said galactomannan.

[0066] The average molecular weight of the cationic galactomannan may be measured by SEC- MALS (Size Exclusion Chromatography with Multi-Angle Light-Scattering detection). A value of 0.140 for dn / dc is used for the molecular weight measurements. A Wyatt MALS detector is calibrated using a 22.5 kDa polyethylene glycol standard. All calculations of the molecular weight distributions are performed using Wyatt's ASTRA software. For cationic galactomannans, the samples are prepared as 0.05% solutions in the mobile phase (100 mM NaNCE, 200 ppm NaNs, 20 ppm pDADMAC) and filtered through 0.45 pm PVDF filters before analysis. 100 pL of the filtered solution are injected and then go through a pre-column plus 3 columns OH pak SB-806 M at 35°C. For modified galactomannans, the samples are prepared as 0.05% solutions in the mobile phase (100 mMNaNCh, 200 ppm NaNs) and filtered through 0.45 pm PVDF filters before analysis. 100 pL of the filtered solution are injected and then go through a pre-column plus 3 columns OH pak SB-806 M at 35°C.

[0067] The galactomannans can be functionalized by chemical modification using a variety of cationic reactive agents, also known as cationizing agents. Cationizing agents of the present invention are defined as compounds which, by reaction with the hydroxyl groups of the galactomannan can lead to galactomannan comprising at least one cationic group according to the invention. In particular, depending on the galactomannan and the hydroxyl groups available for chemical modification, the cationizing agents can react with the available hydroxyl groups of the mannose main chain or backbone, the available hydroxyl groups of the galactose units that are substituted along the mannose main chain or backbone, or both. In this respect, various cationizing agents can be used. Additionally, the cationic galactomannans can be formed from reacting at least one galactomannan in accordance with the invention with at least one cationizing agent.

[0068] Cationizing agents of the present invention are defined as compounds which contain at least one cationic moiety. Cationizing agents comprise agents which can cationize a galactomannan leading to cationic modified galactomannan.

[0069] According to the invention, examples of cationizing agents, which lead to disclosed cationic galactomannans are:

[0070] - cationic epoxides, such as 2,3-epoxypropyltrimethylammonium chloride, 2,3- epoxypropyltrimethylammonium bromide, 2,3 -epoxypropyltrimethylammonium iodide, and mixtures thereof;

[0071] - chlorohydrin-functional cationic nitrogen compounds, such as 3-halogeno-2- hydroxypropyl trimethylammonium chloride, for example 3 -chi oro-2 - hydroxypropyl trimethylammonium chloride, and mixtures thereof;

[0072] - cationic ethylenically unsaturated monomers or their precursors, such as trimethylammoniumpropyl methacrylamide chloride salt, trimethylammoniumpropyl methacrylamide methylsulfate salt, diallyl dimethyl ammonium chloride, vinyl benzyl trimethylammonium chloride, dimethylaminopropyl methacrylamide (tertiary amine) precursors of cationic monomers, such as A-vinyl formamide, A-vinyl acetamide (whose units can be hydrolyzed after polymerization or grafted onto vinyl amine units), and mixtures thereof.

[0073] Particularly, the cationizing agents, which lead to cationic galactomannan of the invention can be selected from 2,3-epoxypropyltrimethylammonium chloride, 2,3- epoxypropyltrimethylammonium bromide, 2,3 -epoxypropyltrimethylammonium iodide, 3 -halogeno-2 -hydroxypropyl trimethylammonium chloride, including for example 3- chloro-2 -hydroxypropyl trimethylammonium chloride, and combinations thereof.

[0074] In a preferred embodiment, the cationic galactomannan of the invention is cationized by at least one cationizing agent selected from 2,3-epoxypropyltrimethylammonium chloride, 3 -chi oro-2 -hydroxypropyltrimethylammonium chloride, and mixtures thereof.

[0075] According to the invention, the cationic groups may be introduced into a modified galactomannan by reacting the modified galactomannan starting material with a derivatizing agent which comprises a reactive functional group and at least one cationic moiety (or a precursor of cationic moiety).

[0076] A group of suitable derivatizing reagents typically contain a reactive functional group, such as an epoxy group, a halide group, an ester group, an anhydride group or an ethylenically unsaturated group, and at least one cationic moiety or a precursor of such cationic moiety.

[0077] As used herein, the term "derivatizing agent" means an agent containing at least a cationic moiety, which is grafted to a galactomannan. The term "derivatizing agent" encompasses the term "cationizing agent". In one embodiment of the invention, the cationic moi eties may be linked to the reactive functional group of the derivatizing agent by a bivalent linking group, such as an alkylene or oxyalkylene group. Suitable cationic moieties include, but are not limited to, primary, secondary, or tertiary amino groups or quaternary ammonium, sulfonium, or phosphonium groups, and combinations thereof.

[0078] The derivatizing agent can comprise a cationic moiety, or a precursor of a cationic moiety, that contains a cationic nitrogen moiety, more typically, a quaternary ammonium moiety. Typical quaternary ammonium moieties are trialkylammonium moieties, such as trimethylammonium moieties, triethylammonium moieties, or tributylammonium moieties, aryldialkylammonium moieties, such as benzyldimethylammonium moieties, and ammonium moieties in which the nitrogen atom is a member of a ring structure, such as pyridinium moieties and imidazoline moieties, each in combination with a counterion, typically a chloride, bromide, iodide counterion or acetate counterion. In one embodiment, the cationic substituent group is linked to the reactive functional group of the cationizing agent by an alkylene or oxyalkylene linking group.

[0079] In a preferred embodiment, the cationic galactomannan of the invention comprises cationic groups selected from amino groups selected from primary, secondary, tertiary amino groups, and combinations thereof; quaternary ammonium groups; sulfonium groups; phosphonium groups; and combinations thereof.

[0080] In still another preferred embodiment, the cationic group of the galactomannan of the invention is selected from trialkylammonium groups, such as trimethylammonium groups, triethylammonium groups, or tributylammonium groups; aryldialkylammonium groups, such as benzyldimethylammonium groups; ammonium groups wherein the nitrogen atom is a member of a ring structure, such as pyridinium groups and imidazoline groups; and combinations thereof.

[0081] According to an embodiment of the invention, the cationic galactomannan may optionally contain other derivatizing groups, such as cationic hydrophobic group or hydrophobic group. Suitable hydrophobic groups include hydroxyalkyl groups, preferably hydroxypropyl groups.

[0082] Advantageously, the cationic galactomannan of the invention is biodegradable.

[0083] The term biodegradable means when a compound / product or any article is naturally degraded and returns to nature without having a harmful impact on the environment. As used herein, biodegradability is measured according to the inherent biodegradability test OECD 302, and in particular the compound / product is considered biodegradable under OECD 302B, as modified and discussed. Specifically, OECD 302B provides testing guidelines for determining whether a chemical substance is considered biodegradable, including inherently biodegradable. The test method OECD 302B means, and as used herein refers to this method without any pre-adaption of the inoculum (z.e., inherent ultimate biodegradable without inoculum pre-adaption), as modified in the following respects: (i) with respect to the % of biodegradability of the sample tested, a sample is considered biodegradable if at least 60% of the tested sample is biodegradable within the tested time period; and (ii) an OxiTop®-IDS sensor available from Xylem Analytics was used to determine the biodegradation. So, for example, in accordance with the above and as used herein, if at least 60% of a material is biodegradable within 60 days, which is the time period tested, then this material is considered to be biodegradable under OECD 302B. As used herein, the inoculum used in OECD 302B, as modified and described above, means that the inoculum was sampled from the environment and was not cultivated to specifically increase the biodegradability of the cationic galactomannans (z.e., the inoculum was not pre-adapted).

[0084] In one embodiment, the cationic galactomannan of the invention is obtained by reacting a modified galactomannan derived from guar gum having a controlled ratio mannose / galactose with at least one cationizing agent.

[0085] According to the invention, in the first step guar gum is submitted to a reaction with at least one enzyme to obtain the modified galactomannan as defined above.

[0086] In Figure 1 the enzymatic process of the invention is depicted.

[0087] The obtained modified galactomannans have controlled mannose / galactose ratio as shown for example in Figure 1.

[0088] By the process of the invention, it is possible not only to allow extensive cleavage by the enzyme through its access to all necessary sites of the guar, but also by the complete removal of the galactose residue cleaved from the guar.

[0089] For enzymatic reactions, guar gum is first swollen with water.

[0090] The swelling of guar gum with water results after grinding in swollen guar in the form of “grated parmesan”. In order to control the swollen state of guar gum, the weight ratio of the total water content to the guar is between 1.5: 1 g / g, preferably between 1 : 1 g / g. If the amount of water is too high a paste or slurry is formed and should be avoided the enzymatic contact with guar during enzymatic reaction is not favored. If the water content is too low, insufficient swelling of the guar is obtained and the resulting enzymatic reaction is deeply affected by the lack of contact between enzyme and guar. In both cases, accessibility of the guar is not good enough for the reaction to occur properly.

[0091] Afterwards, the obtained swollen guar gum is contacted with an enzymatic solution comprising at least one enzyme and a buffer and submitted to enzymatic reaction. Particularly, the enzymatic solution is obtained using a mixture of at least one enzyme and a buffer in a molar concentration of between 0.01 to 0.05 M, preferably between 0.01 to 0.03 M, based on the total weight of the enzymatic solution.

[0092] Buffer solutions used in the sense of the invention may be selected in a non limited way by sodium acetate, potassium acetate solution, sodium citrate solution and potassium phthalate solution.

[0093] Through the enzymatic fragmentation, it is possible to cleave galactose moiety of guar gum to obtain the modified galactomannan.

[0094] The inventors found that the addition of swollen guar portion by portion to the enzymatic solution comprising the enzyme and the buffer allows both good wetting of guar gum by the enzymatic solution and impregnation of enzyme on guar gum. Particularly, the mixture of guar and enzymatic solution is submitted to rigorous stirring and a macroscopically homogeneous gel is formed.

[0095] Preferably, the swollen guar is added to the enzymatic solution in a weight ratio of guar over total weight of the mixture between 0.01 to 0.1, preferably between 0.01 to 0.03, based on the total weight of the mixture.

[0096] The enzymatic reaction is conducted at a temperature of 0 to 90°C, preferably of 30 to 80°C.

[0097] The enzymatic reaction is preferably carried out for a duration of at least 5 hours. According to the invention, the enzymatic reaction is carried out preferably for a duration of 5 to 30 hours, more preferably of 5 to 24 hours. The enzymatic reacted guar is then washed using a mixture of alcohol: water to obtain the raw fragmented galactomannan. The washing mixture comprises alcohol: water in a volume ratio from 1 : 1 to 10:5 (v / v) based on the total volume of the mixture.

[0098] By the use of a washing solution, it is possible to remove galactose residues from the interface of the reaction mixture and the raw galactomannan is obtained.

[0099] Afterwards, the raw fragmented galactomannan is completely dried in an oven at 50°C under atmospheric pressure for 16 hours and ground using a cryogenic grinder into fine powder.

[0100] The inventors have found that the additional washing process allows the complete removal of galactose units cleaved and trapped into the raw fragmented galactomannan mixture.

[0101] In a particular preferred embodiment, the ground powder is then washed at least four times using a mixture of alcohol: water to obtain the modified galactomannan; wherein the modified galactomannan comprises mannose / galactose molar ratio within the range of 2.5 : 1 and 5: 1.

[0102] Particularly, the washing mixture comprises alcohol: water in a volume ratio from 1 : 1 to 10:5 based on the total volume of the mixture.

[0103] Particularly, extra washings after grinding a raw modified galactomannan are unavoidable to get an accurate control of mannose / galactose ratio.

[0104] Furthermore, by using the process of the invention, it is possible to obtain a modified galactomannan having a controlled average ratio of mannose / galactose, which is essential to obtain a desired cationicity of the cationic galactomannan.

[0105] According to a particular preferred embodiment, the process of obtaining a modified galactomannan as described above from guar gum follows the steps: a. the guar gum is swollen with water; b. the obtained swollen guar gum is contacted with an enzyme solution comprising at least one enzyme and a buffer and the obtained mixture is heated at a temperature of 30 to 80°C for a duration of 5 to 30 hours to obtain the enzymatic reacted guar; c. the enzymatic reacted guar is washed at least four times using a mixture of alcohol: water to obtain the raw fragmented galactomannan; d. the raw fragmented galactomannan is ground into fine powder after complete drying and washed at least four times using a mixture of alcohol: water to obtain the modified galactomannan; wherein the modified galactomannan comprises mannose / galactose molar ratio within the range of 2.5 : 1 and 5: 1.

[0106] According to the invention, the alcohol may be selected from, not limited to, isopropanol, methanol and ethanol. According to a preferred embodiment, the selected alcohol is isopropanol.

[0107] In a particular embodiment of the invention, at least one enzyme is selected from galactosidase, preferably alpha-galactosidase, even more preferably alpha-galactosidase of CAZy Family GH27 (glycoside hydrolase 27), which can be obtained from guar seed and Aspergillus niger for example. Typically, GH27 alpha-galactosidases are "endo enzymes" that enable random fragmentation.

[0108] Without being bound to any theory, it is assumed that the nature of alpha-galactosidase (GH27 or GH36) has an impact on the final galactose / mannose distribution of modified guar. Particularly, GH27 alpha-galactosidases may promote random fragmentation while GH36 alpha-galactosidases may only cleave galactose units at the end of the polymeric chain.

[0109] By the process according to the invention, it is possible to accurately control the ratio mannose / galactose in the modified galactomannan and, in the end, to properly target the molecular weight (Mw) and cationicity (DS) of the cationic galactomannan as described above.

[0110] Afterwards, in a second step, the modified galactomannan reacts with at least one cationizing agent to produce the cationic galactomannan as described above. The cationization of galactomannans can be easily made by a skilled person using methods commonly known in the art. Various methods for providing galactomannans with cationic functionality are known in the art, for example as disclosed in U.S. Pat. Pub. No. 2008 / 0112907. Various methods for cross-linking galactomannans with and without cationic modification of the galactomannans are also known, see for example U.S. Pat. No. 5,532,350, U.S. Pat. No. 5,801,116 and U.S. Pat. No. 5,473,059.

[0111] According to the invention, the modified galactomannan with a controlled mannose / galactose ratio obtained by enzymatic treating of guar gum is derivatized or modified so as to contain a cationic group. The resulting compound is the cationic galactomannan of the invention.

[0112] The cationic galactomannan of the invention can be used in home and personal applications, for example as conditioners, stabilizers, thickeners, emulsifiers, deposition aids, rheology modifiers and flocculants.

[0113] Home and personal care compositions such as conditioning shampoos, shower gel and fabric care compositions containing conditioning agents of various types have been disclosed before and are well known by the man skilled in the art to allow for the cleaning and conditioning of hair, skin and fabric, the repair of damaged hair and the styling of hair.

[0114] Personal care compositions mean anything done that is of a personal nature. This may include compositions used for bathing and showering, including bed-baths, lotions and creams notably for skin care, oral hygiene, make-up, and hair care. Specifically composition of the invention may be a skin care composition, such as shower gel, soap, hydrogel, cream, lotion or balm, or a hair care composition, such as shampoo, rinse off conditioner, leave-in conditioner, gel, pomade or cuticle coat.

[0115] Home care composition shall include general household cleaning products for example, toilet bowl cleaners, laundry detergents, fabric softeners, dishwashing liquid, bathroom cleaner and surface cleaner. These compositions may also comprise aesthetic modifiers, film-formers, chelates, emulsifiers, moisturizers, emollients, surfactants (such as anionic, cationic, nonionic, amphoteric, zwitterionic, surfactants, or combinations thereof), propellants, stabilizers, preservatives, cleansing and suspending / gelling agents, and active ingredients.

[0116] Notably these compositions, preferably personal care compositions of the present invention comprises one or more “benefit agents” that is, materials that provide a care benefit, such as moisturizing or conditioning, such as, for example, emollients, oils, moisturizers, humectants, conditioners, polymers, vitamins, abrasives, UV absorbers, antimicrobial agents, anti-dandruff agents, fragrances, and / or appearance modifying additives, such as, for example, colored particles or reflective particles, which may be in the form of a solid, liquid, or gas and may be insoluble or are only partly soluble in the composition. Mixtures of the benefit agents may be used.

[0117] Throughout the description, including the claims, all process terms should be understood as being synonymous with the term method.

[0118] The following examples are included to illustrate embodiments of the invention, but are not limited to described examples.

[0119] EXAMPLES

[0120] All materials are commercially available.

[0121] Enzyme alpha-galactosidase GH27 (glycoside hydrolase 27) purified from guar seed (product code E-AGLGU) was obtained from MEGAZYME.

[0122] Guar gum: Jaguar® S from Solvay.

[0123] Sodium acetate buffer solution (pH 5.2±0.1 at 25°C, for molecular biology, 3 M, 0.2 pm filtered) wasobtained from Sigma-Aldrich (product code S7899-500ML).

[0124] Test methods:

[0125] Molar ratio galactose / mannose Molar ratio galactose:mannose of one modified galactomannan or cationic galactomannan was measured by 'H NMR spectroscopy after acidic hydrolysis (solvent:TFA-d + D2O) at 90°C for 2 hours as described above.

[0126] Molecular weight

[0127] The average molecular weight of the modified galactomannan or the cationic galactomannan was measured by SEC-MALS (Size Exclusion Chromatography with Multi-Angle Light-Scattering detection) with 3 columns Shodex Pack OH pak LB-806 M column, as described above.

[0128] Cationic Degree of Substitution

[0129] The cationic degree of substitution of the cationic galactomannans was measured by 'H NMR after acidic hydrolysis (solvent: TFA-d + D2O) at 90°C for 2 hours, as described above.

[0130] Biodegradability

[0131] The biodegradability of the cationic galactomannans were measured in accordance with OECD 302B (modified, as discussed above), which was modified with respect to the % of biodegradability of the sample tested (i.e., at least 60%) and the sensor used to determine the biodegradation. Biodegradability was assessed based on 28 days, as well as based on 60 days. An OxiTop®-IDS sensor available from Xylem Analytics was used to determine the biodegradation. The inoculum was not pre-adapted.

[0132] A series of enzymatic reactions were performed according to the present invention at the same temperature but varying enzyme loading (U / g of guar, enzymatic activity per gram of guar) and guar concentration in the reaction medium. The modified galactomannans obtained (MG4 to MG7) are summarized at TABLE 1.

[0133] To perform a comparative enzymatic reaction, comparative examples were performed and the obtained comparative modified galactomannans (CMG1 to CMG3) are summarized at TABLE 1.

[0134] Part I: Synthesis of modified galactomannan

[0135] Comparative Example 1: Synthesis of modified galactomannan In step b. In a 500 mL round bottom flask with a magnetic stirrer and a condenser are introduced 150 g of ultrapure water, 0.50 mL of sodium acetate buffer solution (3M, pH 5.2 ± 0.1 at 25°C) and 29 pL of enzyme a-galactosidase (2.9 U of enzyme / g of guar). 5 g of guar gum are added to the enzymatic solution. The obtained paste is mixed with a spatula for 5 minutes every 2 hours for the first 8 hours. The reaction medium is heated at 40°C for 24 hours. After 24 hours, the reaction medium is heated at 80°C for 30 minutes to denature the enzyme. After cooling to room temperature, 200 mL of isopropanol are added into the flask to reduce the viscosity and obtain the reaction medium with enzymatic reacted guar.

[0136] In step c. The reaction medium is filtered under vacuum and washed four times with a solution composed of isopropanol and water (200 mL). A white gel is obtained and it is dried in an oven at 50°C under atmospheric pressure for 16 hours to obtain the raw fragmented galactomannan solid. The raw fragmented galactomannan solid is ground into a fine powder resulting in a comparative modified galactomannan.

[0137] The resulting comparative modified galactomannan CMG1 showed a mannose / galactose molar ratio equal to 1.88: 1.

[0138] Comparative Example 2: Synthesis of modified galactomannan

[0139] In step a. In a mortar, 5 g of guar gum and 5 g of ultrapure water are introduced. The mixture is mixed with a pestle to obtain a swollen guar powder.

[0140] In step b. In a 500 mL round bottom flask with a magnetic stirrer and a condenser are introduced 145 g of ultrapure water, 0.50 mL of sodium acetate buffer solution (3M, pH 5.2 ± 0.1 at 25°C) and 29 pL of enzyme a-galactosidase (2.9 U of enzyme / g of guar). The swollen guar is added to the enzymatic solution portion by portion under stirring (200 rpm). After addition, the reaction medium is heated at 40°C for 24 hours. After 24 hours, the reaction medium is heated at 80°C for 30 minutes to denature the enzyme. After cooling to room temperature, 200 mL of isopropanol are added into the flask to reduce the viscosity and obtain the reaction medium with enzymatic reacted guar. In step c. The reaction medium is filtered under vacuum and washed four times with a solution composed of isopropanol and water (200 mL). A white gel is obtained and it is dried in an oven at 50°C under atmospheric pressure for 16 hours to obtain the raw fragmented galactomannan solid. The raw fragmented galactomannan solid is ground into a fine powder resulting in a comparative modified galactomannan.

[0141] The resulting comparative modified galactomannan CMG2 showed a mannose / galactose molar ratio equal to 2.3 : 1

[0142] Comparative Example 3: Synthesis of modified galactomannan

[0143] In step b. In a 500 mL round bottom flask with a magnetic stirrer and a condenser are introduced 150 g of ultrapure water, 0.50 mL of sodium acetate buffer solution (3M, pH 5.2 ± 0.1 at 25°C) and 29 pL of enzyme a-galactosidase (2.9 U of enzyme / g of guar). 5 g of guar gum are added to the enzymatic solution. The obtained paste is mixed with a spatula for 5 minutes every 2 hours for the first 8 hours. The reaction medium is heated at 40°C for 24 hours. After 24 hours, the reaction medium is heated at 80°C for 30 minutes to denature the enzyme. After cooling to room temperature, 200 mL of isopropanol are added into the flask to reduce the viscosity and obtain the reaction medium with enzymatic reacted guar.

[0144] In step c. The reaction medium is filtered under vacuum and washed four times with a solution composed of isopropanol and water (200 mL). A white gel is obtained and it is dried in an oven at 50°C under atmospheric pressure for 16 hours to obtain the raw fragmented galactomannan solid.

[0145] In step d. The raw fragmented galactomannan solid is ground into a fine powder and further washed four times with a solution composed of isopropanol and water (200 mL) to obtain comparative modified galactomannan.

[0146] The resulting comparative modified galactomannan CMG3 showed a mannose / galactose molar ratio equal to 1.95: 1.

[0147] Example 4: Synthesis of modified galactomannan In step a. In a mortar, 15 g of guar gum and 15 g of ultrapure water are introduced. The mixture is mixed with a pestle to obtain a swollen guar powder.

[0148] In step b. In an 1 L round bottom flask with a magnetic stirrer and a condenser are introduced 435 g of ultrapure water, 1.50 mL of sodium acetate buffer solution (3M, pH 5.2 ± 0.1 at 25°C) and 78 pL of the enzyme a-galactosidase (2.60 U of enzyme / g of guar). The swollen guar is added to the enzymatic solution portion by portion under stirring (200 rpm). After addition, the reaction medium is heated at 40°C for 24 hours. After 24 hours, the reaction medium is heated at 80°C for 30 minutes to denature the enzyme. After cooling to room temperature, 200 mL of isopropanol are added into the flask to reduce the viscosity and obtain the reaction medium with enzymatic reacted guar.

[0149] In step c. The reaction medium is filtered under vacuum and washed four times with a solution composed of isopropanol and water (200 mL). A white gel is obtained and it is dried in an oven at 50°C under atmospheric pressure for 16 hours to obtain the raw fragmented galactomannan solid.

[0150] In step d. The raw fragmented galactomannan solid is ground into a fine powder and further washed by four times with a solution composed of isopropanol and water (200 mL) to obtain modified galactomannan.

[0151] The resulting modified galactomannan MG4 showed a mannose / galactose molar ratio equal to 2.82: 1 and the average molar weight of Mw = 1782 kDa.

[0152] Example 5: Synthesis of modified galactomannan

[0153] In step a. In a mortar, 15 g of guar gum and 15 g of ultrapure water are introduced. The mixture is mixed with a pestle to obtain a swollen guar powder.

[0154] In step b. In an 1 L round bottom flask with a magnetic stirrer and a condenser are introduced 435 g of ultrapure water, 1.50 mL of sodium acetate buffer solution (3M, pH 5.2 ± 0.1 at 25°C) and 82 pL of enzyme a-galactosidase (2.70 U of enzyme / g of guar). The swollen guar is added to the enzymatic solution portion by portion under stirring (200 rpm). After addition, the reaction medium is heated at 40°C for 24 hours. After 24 hours, the reaction medium is heated at 80°C for 30 minutes to denature the enzyme. After cooling to room temperature, 200 mL of isopropanol are added into the flask to reduce the viscosity and obtain the reaction medium with enzymatic reacted guar.

[0155] In step c. The reaction medium is filtered under vacuum and washed four times with a solution composed of isopropanol and water (200 mL). A white gel is obtained and it is dried in an oven at 50°C under atmospheric pressure for 16 hours to obtain the raw fragmented galactomannan solid.

[0156] In step d. The raw fragmented galactomannan solid is ground into a fine powder and further washed by four times with a solution composed of isopropanol and water (200 mL) to obtain modified galactomannan.

[0157] The resulting modified galactomannan MG5 showed a mannose / galactose molar ratio equal to 2.98: 1 and the average molar weight of Mw = 1853 kDa.

[0158] Example 6: Synthesis of modified galactomannan

[0159] In step a. In a mortar, 15 g of guar gum and 15 g of ultrapure water. The mixture is mixed with a pestle to obtain a swollen guar powder.

[0160] In step b. In an 1 L round bottom flask with a magnetic stirrer and a condenser are introduced 435 g of ultrapure water, 1.50 mL of sodium acetate buffer solution (3M, pH 5.2 ± 0.1 at 25°C) and 87 pL of enzyme a-galactosidase (2.90 U of enzyme / g of guar). The swollen guar is added to the enzymatic solution portion by portion under stirring (200 rpm). After addition, the reaction medium is heated at 40°C for 24 hours. After 24 hours, the reaction medium is heated at 80°C for 30 minutes to denature the enzyme. After cooling to room temperature, 200 mL of isopropanol are added into the flask to reduce the viscosity and obtain the reaction medium with enzymatic reacted guar.

[0161] In step c. The reaction medium is filtered under vacuum and washed four times with a solution composed of isopropanol and water (200 mL). A white gel is obtained and it is dried in an oven at 50 °C under atmospheric pressure for 16 hours to obtain the raw fragmented galactomannan solid.

[0162] In step d. The raw fragmented galactomannan is ground into a fine powder and further washed four times with a solution composed of isopropanol and water (200 mL) to obtain modified galactomannan. The resulting modified galactomannan MG6 showed a mannose / galactose molar ratio equal to 3.06: 1 and the average molar weight of Mw = 1698 kDa.

[0163] Example 7: Synthesis of modified galactomannan

[0164] In step a. In a mortar, 17 g of guar gum and 17 g of ultrapure water were introduced. The mixture is mixed with a pestle to obtain a swollen guar powder.

[0165] In step b. In an 1 L round bottom flask with a magnetic stirrer and a condenser are introduced 133 g of ultrapure water, 0.50 mL of sodium acetate buffer solution (3M, pH 5.2 ± 0.1 at 25°C) and 99 pL of enzyme a-galactosidase (2.90 U of enzyme / g of guar). The swollen guar is added to the enzymatic solution portion by portion under stirring (200 rpm). After addition, the reaction medium is heated at 40°C for 24 hours. After 24 hours, the reaction medium is heated at 80°C for 30 minutes to denature the enzyme. After cooling to room temperature, 200 mL of isopropanol are added into the flask to reduce the viscosity and obtain the reaction medium with enzymatic reacted guar.

[0166] In step c. The reaction medium is filtered under vacuum and washed four times with a solution composed of isopropanol and water (200 mL). A white gel is obtained and it is dried in an oven at 50°C under atmospheric pressure for 16 hours to obtain the raw fragmented galactomannan solid.

[0167] In step d. The raw fragmented galactomannan is ground into a fine powder and further washed four times with a solution composed of isopropanol and water (200 mL) to obtain modified galactomannan.

[0168] The resulting modified galactomannan MG7 showed a mannose / galactose molar ratio equal to 2.53: 1 and the average molar weight of Mw = 1652 kDa..

[0169] TABLE 1: modified galactomannan obtained from enzymatic reaction of guar gum.

[0170] As shown in TABLE 1, comparative examples CMG1 to CMG3 demonstrated not only the importance of the correct enzymatic cleavage, but also the complete removal of the galactose residue cleaved from the guar. All examples of the invention, MG4 to MG7 showed precise control of mannose / galactose molar ratio similar to average mannose / galactose molar ratio of galactomannans derived from tara gum.

[0171] Part II: Synthesis of cationic galactomannan

[0172] Example 8: Synthesis of cationic galactomannan

[0173] In a 100 mL round flask, 11.2 g of isopropanol solvent mixed with 4.3 g of deionized water were introduced at room temperature, under a blanket of inert nitrogen gas. Then, 5.01 g of modified galactomannan powder with a mannose / galactose ratio of 2.82: 1 were then loaded at room temperature and under vigorous stirring. After a few minutes of stirring to allow for homogenization, 2.15 g of 3-chloro-2 -hydroxypropyltrimethyl ammonium chloride (Quatl88, 65% in water) was added. This reagent was left to mix at room temperature with the modified galactomannan dispersion for 30 minutes, after which 0.82 g of sodium hydroxide (50% in water) were added slowly. This reagent was left to mix at room temperature with the modified galactomannan dispersion and the cationic etherifying agent for 15 minutes. The dispersion was then heated to 60°C and held at this temperature for 60 minutes, after which the temperature was lowered to at least 50°C in order to start the washing procedure. A reaction mixture obtained as described above was dispersed under stirring with 6.3 g of isopropanol (99%) and 1.3 g of water. The pH was adjusted to approximately 9-10 using glacial acetic acid. The mixture was then left under stirring for 30 minutes. This dispersion was then filtered under vacuum. This washing and filtering procedure was repeated two more times for 30 minutes with 14.4 g of isopropanol (99%) and 5.8 g of water. The obtained solid was then let dry overnight for 6 hours in an oven at 60°C.

[0174] The cationic degree of substitution (DScationic) was 0.17 and the (DScat)extraction was 0.14. The average molecular weight (Mw) was 1037 kDa. The cationic galactomannan was evaluated according to the OECD 302B procedure. The biodegradation expressed was 64% after 28 days. The cationic galactomannan is considered as inherently ultimately biodegradable.

[0175] Example 9: Synthesis of cationic galactomannan

[0176] In a 100 mL round flask, 22.5 g of isopropanol solvent mixed with 8.6 g of deionized water were introduced at room temperature, under a blanket of inert nitrogen gas. Then, 10.05 g of modified galactomannan powder with a mannose / galactose ratio of2.53: l were then loaded at room temperature and under vigorous stirring. After a few minutes of stirring to allow for homogenization, 4.29 g of 3-chloro-2-hydroxypropyltrimethyl ammonium chloride (Quatl88, 65% in water) was added. This reagent was left to mix at room temperature with the modified galactomannan dispersion for 30 minutes, after which 1.74 g of sodium hydroxide (50% in water) were added slowly. This reagent was left to mix at room temperature with the modified galactomannan dispersion and the cationic etherifying agent for 15 minutes. The dispersion was then heated to 60°C and held at this temperature for 60 minutes, after which the temperature was lowered to at least 50°C in order to start the washing procedure.

[0177] A reaction mixture obtained as described above was dispersed under stirring with 13.0 g of isopropanol (99%) and 2.9 g of water. The pH was adjusted to approximately 9-10 using glacial acetic acid. The mixture was then left under stirring for 30 minutes. This dispersion was then filtered under vacuum. This washing and filtering procedure was repeated two more times for 30 minutes with 28.6 g of isopropanol (99%) and 11.4 g of water. The obtained solid was then let dry overnight for 6 hours in an oven at 60°C. The cationic degree of substitution (DScationic) was 0.19 and the (DScat)extraction was 0.16. The average molecular weight (Mw) was 1336 kDa. The cationic galactomannan was evaluated according to the OECD 302B procedure. The biodegradation expressed was 65% after 41 days. The cationic galactomannan is considered as inherently ultimately biodegradable.

[0178] Part III: Conditioning performance

[0179] In the study below we compared standard shampoo formulation including cationic galactomannan versus standard shampoo formulation including Jaguar® C17 (commercial product from Solvay). The conditioning performance was assessed by a combing procedure.

[0180] Example 10 - Conditioning - Combing Improvement test Protocol

[0181] To assess the conditioning via wet combing and dry hair look properties of the shampoos, flat calibrated tresses of bleached Caucasian hair weighing about 4.0 grams were used. The hair tresses were purchased from SP Equation, Quartier Fariguriere, 138 rue Marius Bourrelly, 83470 Pourcieux, France. Prior to being actually shampooed, the hair tresses were first cleansed with a 14% active sodium laureth sulfate (SLES) solution. For this cleansing step, the hair tresses were wetted with 30°C running water for 60 seconds, washed for 60 seconds with 2.0 mL of the SLES solution, and then the hair tresses were rinsed under 30°C running water for 60 seconds. This process was repeated a second time.

[0182] At this point the hair tresses were then gently hand combed to remove major tangles and then combed ten times at 300 mm / min using a MTT 175 Miniature Tensile Tester (Dia- Stron Ltd) equipped with an ACE hard rubber fine tooth comb. The hair was immersed in water and wrung through between the index and middle finger to keep it wet between each combing cycle. The tresses were hung vertically and stored overnight in a climatic room at about 21°C ± 5°C and about 50% relative humidity.

[0183] In a second step, each of the aforementioned hair tress was rewetted under running water for 60 seconds and shampooed by applying 0.2 gram of shampoo per gram of hair along the hair length. The tress was kneaded for 45 seconds and then it was rinsed under 30°C running water for 30 seconds and then wrung through between the index and middle finger. This second step is repeated once more.

[0184] The shampooed hair tresses whilst still being wet were then gently hand combed to remove major tangles and then combed for ten times at 300 mm / min using a MTT 175 Miniature Tensile Tester (Dia-Stron Ltd) equipped with an ACE hard rubber fine tooth comb. Between each combing cycle, the hair was rewetted with water to keep it wet. Combing force versus displacement curves were obtained in the process. Total combing works (corresponding to the integral of this signal) are extracted. From the 10 combing cycle data, the average wet combing work was calculated for each hair tress. For each formulation, a minimum of three hair tresses were assigned and used to determine the average total combing work for the formulation. The lower the total work is, the higher the wet conditioning efficiency of the formulation is. Using the total combing work of each hair tress before and after shampoo application, as described in the steps above, the percent combing improvement is calculated and reported in TABLE 2.

[0185] TABLE 2. Combing improvements of cationic galactomannan and Jaguar® Cl 7.

[0186] As shown in TABLE 2, cationic galactomannan according to the invention could significantly reduce the combing force, comparable to commercially cationic guar.

[0187] Therefore, it was demonstrated a process able to develop a cationic galactomannan starting from guar gum, having not only a controlled molar ratio mannose / galactose similar to a natural tara gum, but also controlled molecular weight and cationicity, with the additional advantage of being biodegradable.

Claims

C L A I M S1. A cationic galactomannan comprising a mannose / galactose molar ratio within the range of 2.5: 1 and 5: 1, wherein the cationic galactomannan is derived from guar gum, wherein the cationic galactomannan exhibits a (DScat)extraction for cationic substituent groups ranging from 0.01 to 1.0, preferably from 0.01 to 0.4, more preferably from 0.05 to 0.2.

2. The cationic galactomannan according to claim 1, wherein the mannose / galactose ratio is on average 3:1.

3. The cationic galactomannan according to any one of the claims 1 to 3, wherein the cationic galactomannan has a molecular weight distribution ranging from 600 kDa to 1900 kDa.

4. The cationic galactomannan according to any one of the preceding claims, wherein the cationic galactomannan is cationized by at least one cationizing agent selected from 2,3- epoxypropyltrimethylammonium chloride, 3 -chi oro-2 - hydroxypropyltrimethylammonium chloride, and mixtures thereof.

5. The cationic galactomannan according to any one of the preceding claims, wherein the cationic galactomannan comprises cationic groups selected from amino groups selected from primary, secondary, tertiary amino groups, and combinations thereof; quaternary ammonium groups; sulfonium groups; phosphonium groups; and combinations thereof.

6. The cationic galactomannan according to any one of the preceding claims, wherein the cationic group is selected from trialkylammonium groups, such as trimethylammonium groups, triethylammonium groups, or tributylammonium groups; aryldialkylammonium groups, such as benzyldimethylammonium groups; ammonium groups wherein the nitrogen atom is a member of a ring structure, such as pyridinium groups and imidazoline groups; and combinations thereof.

7. The cationic galactomannan according to any one of the preceding claims, wherein the cationic galactomannan optionally further comprises at least one nonionic group selected from hydroxy alkyl group, preferably a hydroxypropyl group.

8. The cationic galactomannan according to any one of the preceding claims, wherein the cationic galactomannan is biodegradable.

9. A process of preparing a cationic galactomannan as defined in any of the claims 1 to 8, by reacting a modified galactomannan derived from guar gum and comprising a mannose / galactose molar ratio within the range of 2.5:1 and 5:1 with at least one cationizing agent.

10. The process according to claim 9, wherein in a first step guar gum is submitted to a reaction with at least one enzyme to obtain the modified galactomannan comprising mannose / galactose molar ratio within the range of 2.5: 1 and 5: 1 and in a second step the modified galactomannan reacts with at least one cationizing agent, wherein in the first step: a. the guar gum is swollen with water; b. the obtained swollen guar gum is contacted with an enzyme solution comprising at least one enzyme and a buffer and the obtained mixture is heated at a temperature of 30 to 80°C for a duration of 5 to 30 hours to obtain the enzymatic reacted guar; c. the enzymatic reacted guar is washed at least four times using a mixture of alcohol: water to obtain the raw fragmented galactomannan; d. the raw fragmented galactomannan is ground into fine powder after complete drying and washed at least four times using a mixture of alcohol: water to obtain the modified galactomannan; wherein the modified galactomannan comprises mannose / galactose molar ratio within the range of 2.5 : 1 and 5: 1.

11. The process according to claim 10, wherein the mixture alcohokwater comprises a volume ratio from 1 : 1 to 10:5, based on the total volume of the mixture.

12. The process according to claims 10 or 11, wherein the alcohol is selected from isopropanol, methanol and ethanol.

13. The process according to any one of the claims 10 to 12, wherein at least one enzyme is selected from galactosidase, preferably alpha-galactosidase.

14. Use of the cationic galactomannan as defined in any of the claims 1 to 8, as conditioners, stabilizers, thickeners, emulsifiers, deposition aids, rheology modifiers, hair repair agents, hair straightening formulation components, hair split end repair agents and flocculants.

15. A composition comprising at least a cationic galactomannan as defined in any of the claims 1 to 8.

16. The composition according to claim 15, wherein it is a home and personal care composition.

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