Biodegradable cationic galactomannans

Abstract

The present invention generally relates to biodegradable cationic galactomannans.

Description

[0001] Biodegradable Cationic Galactomannans

[0002] This application claims priority to U.S. Provisional Patent Application 63 / 592,305, filed on October 23, 2023, the whole content of which is hereby incorporated herein by reference in its entirety for all purposes.

[0003] TECHNICAL FIELD

[0004] The present invention generally relates to biodegradable cationic galactomannans. More specifically, the present invention relates to biodegradable cationic galactomannans having certain cationic degrees of substitution (DScationic) and average molecular weights (Mw). The present invention also relates to methods for making the biodegradable cationic galactomannans, as well as compositions having the biodegradable cationic galactomannans.

[0005] BACKGROUND

[0006] Galactomannans are a type of natural polymers formed from certain sugar residues. More specifically, galactomannans are polysaccharides having |3-(1 ,4)- linked D-mannopyranosyl residues forming the main chain of the polymer, otherwise known as the backbone, with different degrees of substitution with a-(1 , 6)-linked D- galactopyranosyl residues along the same as the side chains. The ratio of mannose to galactose not only determines the physical properties of the galactomannans, but the ratio of mannose to galactose also determines the type of galactomannan. For instance, the galactomannan fenugreek has a mannose to galactose ratio of about 1 :1. Other galactomannans have different mannose to galactose ratios. Tara, locust bean, and cassia have mannose to galactose ratios of about 3:1 , about 4: 1 , and about 5: 1 , respectively. Meanwhile, native guar or guar gum typically has a mannose to galactose ratio of about 2:1 .

[0007] Naturally occurring galactomannans can be extracted from the endosperm of the respective seeds. And while the naturally occurring galactomannans can be used in their native form for certain applications without any functionalization or chemical modification, nevertheless by functionalizing galactomannans via chemical modification, the functionalized galactomannans can provide better performance properties in a number of applications. For instance, depending on the application, cationic galactomannans can be used as conditioners, stabilizers, thickeners, emulsifiers, deposition aids, rheology modifiers, and flocculants. Notably, each galactose and mannose unit in the native galactomannans have hydroxyl groups that can be chemically modified to functionalize the galactomannan. In this respect, the galactomannans can be functionalized using a number of reactive agents. For example, in order to add cationic groups to the galactomannans, one or more cationic reactive agents, also known as cationizing agents, can be used. By adding cationic functional groups, the cationic galactomannans can not only have better performance properties, but since the galactomannans are extracted from natural and renewable sources, the polymers provide a significant advantage over petroleum based or synthetic polymers.

[0008] However, while cationic galactomannans can be used in a variety of applications and the starting unmodified galactomannans are naturally derived, cationic galactomannans may not have the desired biodegradability properties in the environment, especially based on newer and more stringent biodegradability guidelines and requirements. That is, cationic galactomannans may not be considered readily biodegradable, particularly under stricter biodegradability standards. In this respect, there remains a need in the art for cationic galactomannans that not only have sufficient cationization for the desired performance, but are also sufficiently biodegradable. Simply put, there is a need in the art for biodegradable cationic galactomannans.

[0009] Further, there remains a need in the art for methods for making biodegradable cationic galactomannans, as well as compositions having biodegradable cationic galactomannans.

[0010] SUMMARY OF THE INVENTION

[0011] The present invention generally relates to biodegradable cationic galactomannans. In this respect, an embodiment of the present invention relates to a biodegradable cationic galactomannan comprising a ratio of galactose to mannose units of about 1 :1 , the cationic galactomannan having:

[0012] (a) a DScationic of lower than 0.17, preferably 0.16 or lower, more preferably 0.15 or lower; and

[0013] (b) an average molecular weight (Mw) lower than 3,500,000 g / mol. An embodiment of the present invention also relates to a biodegradable cationic galactomannan comprising a ratio of galactose to mannose units of about 1 :1 , the cationic galactomannan having:

[0014] (a) a DScationic of lower than 0.17, preferably 0.16 or lower, more preferably 0.15 or lower; and

[0015] (b) an average molecular weight (Mw) lower than 3,500,000 g / mol, wherein the cationic galactomannan has a biodegradability of 60% or greater within 28 days in accordance with OECD 301 F, and in another embodiment the cationic galactomannan has a biodegradability of 60% or greater within 60 days in accordance with OECD 301 F.

[0016] Another embodiment of the present invention relates to a biodegradable cationic galactomannan comprising a ratio of galactose to mannose units of about 1 :3 to about 1 :5, preferably about 1 :3 to about 1 :4, the cationic galactomannan having:

[0017] (a) a DScationic of lower than 0.18, preferably 0.17 or lower; and

[0018] (b) an average molecular weight (Mw) lower than 2,500,000 g / mol.

[0019] An embodiment of the present invention also relates to a biodegradable cationic galactomannan comprising a ratio of galactose to mannose units of about 1 :3 to about 1 :5, preferably about 1 :3 to about 1 :4, the cationic galactomannan having:

[0020] (a) a DScationic of lower than 0.18, preferably 0.17 or lower; and

[0021] (b) an average molecular weight (Mw) lower than 2,500,000 g / mol, wherein the cationic galactomannan has a biodegradability of 60% or greater within 28 days in accordance with OECD 301 F, and in another embodiment the cationic galactomannan has a biodegradability of 60% or greater within 60 days in accordance with OECD 301 F.

[0022] In an additional embodiment, the present invention relates to a biodegradable cationic galactomannan comprising a ratio of galactose to mannose units of about 1 :5, the cationic galactomannan having:

[0023] (a) a DScationic of lower than 0.18; and

[0024] (b) an average molecular weight (Mw) lower than 1 ,000,000 g / mol. An embodiment of the present invention also relates to a biodegradable cationic galactomannan comprising a ratio of galactose to mannose units of about 1 :5, the cationic galactomannan having:

[0025] (a) a DScationic of lower than 0.18; and

[0026] (b) an average molecular weight (Mw) lower than 1 ,000,000 g / mol, wherein the cationic galactomannan has a biodegradability of 60% or greater within 28 days in accordance with OECD 301 F, and in another embodiment the cationic galactomannan has a biodegradability of 60% or greater within 60 days in accordance with OECD 301 F.

[0027] Further, in other embodiments, the cationic galactomannans comprise cationic groups selected from primary, secondary or tertiary amino groups; quaternary ammonium groups; sulfonium groups; phosphonium groups; and combinations thereof, and preferably 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. Embodiments of the present invention also include biodegradable cationic galactomannans, wherein the galactomannan is cationized by at least one cationizing agent selected from 2,3-epoxypropyltrimethylammonium chloride, 3-chloro-2-hydroxypropyltrimethylammonium chloride, and mixtures thereof.

[0028] In yet another embodiment, the present invention relates to compositions having the biodegradable cationic galactomannans. The present invention also relates to methods for making biodegradable cationic galactomannans, including an embodiment of reacting a non-cationic galactomannan with at least one cationizing agent.

[0029] DETAILED DESCRIPTION OF THE INVENTION

[0030] The term and phrases “invention,” “present invention,” “instant invention,” and similar terms and phrases as used herein are non-limiting and are not intended to limit the present subject matter to any single embodiment, but rather encompasses all possible embodiments as described. Throughout the description, including the claims, the term “a” and the phrase “at least one” are synonymous, and likewise, the phrase "comprising one" or “comprising a" should be understood as being synonymous with the term "comprising at least one," unless otherwise specified. Additionally, "between" should be understood as being inclusive of the limits. Further, throughout the description, including the claims, the terms “comprising” and “having” can be used interchangeably, and should be understood as being synonymous.

[0031] It should be noted that in specifying any range of concentration, weight ratio or amount, any particular upper concentration, weight ratio or amount can be associated with any particular lower concentration, weight ratio or amount, respectively.

[0032] Biodegradable Cationic Galactomannans

[0033] A variety of galactomannans can be used for the present invention. As discussed above, galactomannans are natural polymers formed from mannose and galactose units, in which the mannose units form the main chain or backbone of the polymer, while the galactose units are substituted along the main chain or backbone. In this respect, galactomannans having a mannose to galactose ratio of about 1 :1 to about 5:1 can be used.

[0034] In certain embodiments, the galactomannans can have a mannose to galactose ratio of about 1 :1. The galactomannan having a mannose to galactose ratio of about 1 :1 is commonly referred to as fenugreek, but it is also known as Trigonella foenum-graecum. In other embodiments, the galactomannans can have a mannose to galactose ratio of about 3: 1 to about 5:1 . Such galactomannans are commonly known as tara (also known as Tara spinosa), locust bean or carob (also known as Parkia biglobosa), and cassia (also known as Cassia obtusifolia and Cassia tora), respectively. Cassia can also be referred to as Senna obtusifolia and Senna tora.

[0035] For example, galactomannans of the present invention can include those having repeating residues (7.e. , units) as shown below in formula (I):

[0036] wherein n can be 0 to 5, preferably n can be 0 to 4; m can be 0 to 5, preferably m can be 0 to 4; with the proviso that n+m is not greater than about 5, preferably with the proviso that n+m is not greater than about 4. The value p in formula (I) is based on the overall molecular weight (Mw) of the galactomannans, as further described below. In certain preferred embodiments, n+m can be equal to about 0, 2, 3, 4, or 5, preferably n+m can be equal to about 0, 2, 3, or 4. Also, in certain embodiments, p can be up to about 35,000, up to about 30,000, up to about 25,000, further up to about 20,000, and p can be at least about 10, at least about 100, and at least about 500. In alternative embodiments, p can be lower than about 10, including at least about 5 when n+m is not greater than about 5, preferably when n+m is not greater than about 4, and in certain preferred alternative embodiments, p can be at least about 5 when n+m is equal to about 0, 2, 3, 4, or 5, preferably about 0, 2, 3, or 4. For instance, in certain embodiments, p can range from about 10 to about 35,000, including from about 100 to about 30,000. In certain embodiments, p can be about 500 to about 10,000, especially when n+m is about 0; p can be about 2,500 to about 5,000 when n+m is about 2 to 4, and in particular about 2 to 3; and p can be about 100 to about 1 ,200 when n+m is about 5, and in particular about 4.

[0037] The galactomannans can be functionalization by chemical modification using a variety of cationic reactive agents, also known as cationizing agents. The cationizing agents can react with the available hydroxyl groups of the galactomannan. 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.

[0038] As used herein, the term “cationic” and “cationizing” means at least partially cationic. Therefore, the terms “cationizing agent,” “cationic group,” “cationic moiety,” or the plurals thereof can include for example ammoniums, which have a positive charge, as well as primary, secondary, and tertiary amines and precursors thereof that can lead to or can result in positively charged compounds.

[0039] Since the cationizing agents can react with the available hydroxyl groups of the galactomannan to produce the cationic galactomannans, the cationizing agents can have at least one functional group (or moiety) that can react with the same. Such functional groups include, but are not limited to, at least one epoxy, halide, ester, anhydride, ethylenically unsaturated group, or combinations thereof, as well as salts and radicals thereof. In one embodiment, the cationizing agents can have a bivalent linking group, such as an alkylene or oxyalkylene group, between or linking the cationic group(s) or moiety(ies) and the functional or reactive group(s) or moiety(ies) of the cationizing agent. For example, cationic groups or moieties can include, but are not limited to, amino groups, such as primary, secondary, and / or tertiary amino groups, quaternary ammonium groups, sulfonium groups, phosphonium groups, and combinations thereof.

[0040] In one embodiment, the cationizing agents can have a cationic group or moiety that comprises a cationic nitrogen group, more typically, a quaternary ammonium group. Typical quaternary ammonium groups include but are not limited to are trialkylammonium groups, such as trimethylammonium groups, triethylammonium groups, tributylammonium groups, aryldialkylammonium groups, such as benzyldimethylammonium groups, and ammonium groups in which the nitrogen atom is a member of a ring structure, such as pyridinium groups and imidazoline groups, each in combination with a counterion, typically a chloride, bromide, iodide, 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.

[0041] In certain embodiments, the cationic groups or moieties can be of formula (II):

[0042] -N+R2R3R4X- (II) wherein for amine salt groups R2, R3, and R4are each independently organic groups or H in which at least one of R2, R3, and R4is H for the amine salt groups; for quaternary ammonium groups R2, R3, and R4are each independently organic groups, or any two of R2, R3, and R4may be fused to form with the nitrogen atom to which they are attached a heterocyclic group, and X’ is an anion.

[0043] In other embodiments, the cationizing agents can be cationic epoxides, such as epoxy-functional cationic nitrogen compounds, as well as chlorohydrin-functional cationic nitrogen compounds, cationic ethylenically unsaturated monomers or their precursors, and combinations thereof. For example, cationic epoxides of the present invention can include, but are not limited to 2,3-epoxypropyltrimethylammonium chloride, 2,3-epoxypropyltrimethylammonium bromide, 2,3- epoxypropyltrimethylammonium iodide, and mixtures thereof; chlorohydrin- functional cationic nitrogen compounds can include, but are not limited to 3- halogeno-2-hydroxypropyl trimethylammonium chloride, including for example 3- chloro-2-hydroxypropyl trimethylammonium chloride, 3-chloro-2-hydroxypropyl dodecyldimethylammonium chloride, 3-chloro-2-hydroxypropyl lauryldimethylammonium chloride, 3-chloro-2-hydroxypropyl cocoalkyldimethylammonium chloride, 3-chloro-2-hydroxypropyl stearyldimethylammonium chloride, and mixtures thereof; and cationic ethylenically unsaturated monomers or their precursors can include, but are not limited to trimethylammoniumpropyl methacrylamide chloride salt, methacrylamidopropyl trimethylammonium chloride (MAPTAC), trimethylammoniumpropyl methacrylamide methylsulfate salt, diallyl dimethyl ammonium chloride, vinyl benzyl trimethylammonium chloride, dimethylaminopropyl methacrylamide (tertiary amine) precursors of cationic monomers, such as N-vinyl formamide, and N-vinylacetamide (which can be hydrolyzed after polymerization or grafted onto vinyl amine units), and combinations thereof.

[0044] In certain preferred embodiments, the cationizing agents 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. For example, cationic galactomannans of the present invention can include those having repeating residues (i.e., units) as shown below in formula (III): wherein:

[0045] R1can have formula:

[0046] R5N+R2R3R4X- (IV); wherein for amine salt groups R2, R3, and R4are each independently organic groups or H, preferably each are independently a C1-C32 alkyl group or H, more preferably each are independently a C1-C18 alkyl group or H, and in certain preferred embodiments R2, R3, and R4are each independently a C1-C10 alkyl group or H, including each are independently a C1-C5 alkyl group or H, and in which at least one of R2, R3, and R4is H for the amine salt groups; for quaternary ammonium groups R2, R3, and R4are each independently organic groups, preferably each are independently a C1-C32 alkyl group, more preferably each are independently a C1- C alkyl group, and in certain preferred embodiments R2, R3, and R4are each independently a C1-C10 alkyl group, including each are independently a C1-C5 alkyl group, or any two of R2, R3, and R4may be fused to form with the nitrogen atom to which they are attached a heterocyclic group; and X’ is an anion, preferably CI-, Br- , I, or mixtures thereof, more preferably CI-;

[0047] R5is a C1-C5 hydrocarbon group, optionally substituted with at least one group selected from (-OH), (=0), (-NH3), or mixtures thereof, preferably a C1-C5 alkyl group, optionally substituted with at least one group selected from (-0H), (=0), (- NH3), or mixtures thereof;

[0048] R10can be selected from -OH, an alkoxy quaternary ammonium group, or combinations thereof, preferably R10can be selected from -OH, -OR1, or combinations thereof, with the proviso that at least one R10is an alkoxy quaternary ammonium group, preferably -OR1; and n can be 0 to 5, preferably n can be 0 to 4; m can be 0 to 5, preferably m can be 0 to 4; with the proviso that n+m is not greater than about 5, preferably n+m is not greater than about 4, and preferably n+m can be equal to about 0, 2, 3, 4, or 5, preferably n+m can be equal to about 0, 2, 3, or 4. The value p in formula (III) is based on the overall molecular weight (Mw) of the galactomannans, as further described below. Further, in certain embodiments, p can be up to about 35,000, up to about 30,000, up to about 25,000, further up to about 20,000, and p can be at least about 10, at least about 100, and at least about 500. In alternative embodiments, p can be lower than about 10, including at least about 5 when n+m is not greater than about 5, preferably when n+m is not greater than about 4, and in certain preferred alternative embodiments, p can be at least about 5 when n+m is equal to about 0, 2, 3, 4, or 5, preferably about 0, 2, 3, or 4. In certain embodiments, p can range from about 10 to about 35,000, including from about 100 to about 30,000. In certain embodiments, p can be about 500 to about 10,000, especially when n+m is about 0; p can be about 2,500 to about 5,000 when n+m is about 2 to 4, and in particular about 2 to 3; and p can be about 100 to about 1 ,200 when n+m is about 5, and in particular about 4.

[0049] In certain embodiments, the cationic galactomannans of the present invention can include those having repeating residues (7.e. , units) as shown below in formula (V): wherein:

[0050] R1can have formula:

[0051] R5N+R2R3R4X- (VI); wherein for amine salt groups R2, R3, and R4are each independently organic groups or H, preferably each are independently a C1-C32 alkyl group or H, more preferably each are independently a C1-C18 alkyl group or H, and in certain preferred embodiments R2, R3, and R4are each independently a C1-C10 alkyl group or H, including each are independently a C1-C5 alkyl group or H, and in which at least one of R2, R3, and R4is H for the amine salt groups; for quaternary ammonium groups R2, R3, and R4are each independently organic groups, preferably each are independently a C1-C32 alkyl group, more preferably each are independently a C1- C alkyl group, and in certain preferred embodiments R2, R3, and R4are each independently a C1-C10 alkyl group, including each are independently a C1-C5 alkyl group, or any two of R2, R3, and R4may be fused to form with the nitrogen atom to which they are attached a heterocyclic group; and X’ is an anion, preferably CI-, Br- , I, or mixtures thereof, more preferably CI-;

[0052] R5is a C1-C5 hydrocarbon group, optionally substituted with at least one group selected from (-OH), (=0), (-NH3), or mixtures thereof, preferably a C1-C5 alkyl group, optionally substituted with at least one group selected from (-0H), (=0), (- NH3), or mixtures thereof;

[0053] R10can be selected from -OH, an alkoxy quaternary ammonium group, or combinations thereof, preferably R10can be selected from -OH, -OR1, or combinations thereof; and n can be 0 to 5, preferably n can be 0 to 4; m can be 0 to 5, preferably m can be 0 to 4; with the proviso that n+m is not greater than about 5, preferably n+m is not greater than about 4, and preferably n+m can be equal to about 0, 2, 3, 4, or 5, preferably n+m can be equal to about 0, 2, 3, or 4. The value p in formula (V) is based on the overall molecular weight (Mw) of the galactomannans, as further described below. Further, in certain embodiments, p can be up to about 35,000, up to about 30,000, up to about 25,000, further up to about 20,000, and p can be at least about 10, at least about 100, and at least about 500. In alternative embodiments, p can be lower than about 10, including at least about 5 when n+m is not greater than about 5, preferably when n+m is not greater than about 4, and in certain preferred alternative embodiments, p can be at least about 5 when n+m is equal to about 0, 2, 3, 4, or 5, preferably about 0, 2, 3, or 4. In certain embodiments, p can range from about 10 to about 35,000, including from about 100 to about 30,000. In certain embodiments, p can be about 500 to about 10,000, especially when n+m is about 0; p can be about 2,500 to about 5,000 when n+m is about 2 to 4, and in particular about 2 to 3; and p can be about 100 to about 1 ,200 when n+m is about 5, and in particular about 4.

[0054] Once the galactomannans are reacted with at least one cationizing agent to form the cationic galactomannans of the present invention, the cationic galactomannans have a degree of substitution with respect to the cationic groups that are attached to the galactomannan (DScationic). In particular, the DScationic means the average number of the cationic groups or moieties attached per monomeric unit (i.e., each sugar unit) of the galactomannan. For clarity, cationic galactomannans of the present invention have some cationic degree of substitution. That is, the cationic galactomannans of the present invention cannot have zero or no cationic degree of substitution. In this respect, for ranges of DScationic in which only an upper limit is specified, such as for example lower than 0.24, lower than 0.23, lower than 0.22, lower than 0.21 , lower than 0.20, lower than 0.19, lower than 0.18, lower than 0.17, lower than 0.16, and lower than 0.15, and similarly 0.24 or lower, 0.23 or lower, 0.22 or lower, 0.21 or lower, 0.20 or lower, 0.19 or lower, 0.18 or lower, 0.17 or lower, 0.16 or lower, 0.15 or lower, and similar ranges, the lower end of the range is greater than zero (>0). In such embodiments, the lower end of the range can be 0.000001 , 0.00001 , 0.0001 , 0.001 , 0.01 , or 0.10.

[0055] Depending on the type and average molecular weight (Mw) of galactomannan, in certain embodiments the cationic galactomannans of the present invention can generally have a DScationic of up to about 0.30. However, in one aspect of the present invention, it has been surprisingly and unexpectedly found that while cationic galactomannans having lower average molecular weights can potentially have higher cationic degrees of substitution while still maintaining sufficient biodegradability, cationic galactomannans having higher molecular weights usually have lower cationic degrees of substitution in order to have sufficient biodegradability. In another aspect of the present invention, it has been surprisingly and unexpectedly found that the type of galactomannan - that is, the ratio of galactose to mannose units - may also affect the biodegradability, along with the DScationic and average molecular weight (Mw). Accordingly, in certain embodiments in which the cationic galactomannan has a ratio of galactose to mannose units of about 1 :1 , which is commonly referred to as fenugreek, the cationic galactomannan can generally have a DScationic of lower than 0.17, including 0.16 or lower, as well as 0.15 or lower. For example, in certain embodiments in which the cationic galactomannan has a ratio of galactose to mannose units of about 1 :1 , the cationic galactomannan can generally have a DScationic of less than 0.17. In additional embodiments, when the cationic galactomannan has a ratio of galactose to mannose units of about 1 :1 , the cationic galactomannan can have a DScationic of 0.15 or lower, preferably 0.14 or lower. In this respect, the DScationic can range from 0.001 to 0.16, from 0.01 to 0.16, and from 0.10 to 0.16, as well as from 0.001 to 0.15, from 0.01 to 0.15, and from 0.10 to 0.15, and furthermore, from 0.001 to 0.14, from 0.01 to 0.14, and from 0.10 to 0.14. In further embodiments, the cationic galactomannan having a ratio of galactose to mannose units of about 1 :1 , the cationic galactomannan can have a DScationic ranging from 0.05 to 0.16, preferably from 0.08 to 0.16, more preferably from 0.10 to 0.16. Similarly, in other embodiments, the cationic galactomannan having a ratio of galactose to mannose units of about 1 :1 , the cationic galactomannan can have a DScationic ranging from 0.05 to less than 0.17, preferably from 0.08 to less than 0.17, more preferably from 0.10 to less than 0.17, and the cationic galactomannans having a ratio of galactose to mannose units of about 1 : 1 can further have a DScationic ranging from 0.10 to 0.16, preferably from 0.12 to 0.16, more preferably from 0.14 to 0.16. In certain embodiments when the cationic galactomannans have a ratio of galactose to mannose units of about 1 :1 , the cationic galactomannans can have a DScationic of 0.16 or lower and the cationic galactomannans can have a biodegradability of 60% or greater within 60 days, preferably within 28 days, in accordance with OECD 301 F.

[0056] In other embodiments in which the cationic galactomannan has a ratio of galactose to mannose units of about 1 :3 to about 1 :5, which are commonly referred to as tara, locust bean or carob, and cassia, and an average molecular weight lower than 2,500,000 g / mol, the cationic galactomannan can generally have a DScationic of 0.18 or lower, preferably lower than 0.18, more preferably 0.17 or lower. In certain preferred embodiments, the cationic galactomannan has a ratio of galactose to mannose units of about 1 :3 to about 1 :4, preferably about 1 :3 or about 1 :4. In additional embodiments, when the cationic galactomannan has a ratio of galactose to mannose units of about 1 :3 to about 1 :5, preferably about 1 :3 to about 1 :4, more preferably about 1 :3 or about 1 :4, and an average molecular weight lower than 2,500,000 g / mol, the cationic galactomannan can have a DScationic of 0.19 or lower, preferably 0.18 or lower. In other embodiments, when the cationic galactomannan has a ratio of galactose to mannose units of about 1 :3 to about 1 :5, preferably about 1 :3 to about 1 :4, including about 1 :3 or about 1 :4, and an average molecular weight lower than 2,500,000 g / mol, the cationic galactomannan can have a DScationic of 0.18 or lower, preferably lower than 0.18, more preferably 0.17 or lower. In this respect, the DScationic can range from 0.001 to 0.18, from 0.01 to 0.18, and from 0.10 to 0.18, as well as from 0.001 to lower than 0.18, from 0.01 to lower than 0.18, and from 0.10 to lower than 0.18, and furthermore, from 0.001 to 0.17 or lower, from 0.01 to 0.17 or lower, and from 0.10 to 0.17 or lower. The DScationic range for when the cationic galactomannan has a ratio of galactose to mannose units of about 1 :3 to about 1 :5, preferably about 1 :3 to about 1 :4, including about 1 :3 or about 1 :4, can also range from 0.001 to 0.16, from 0.01 to 0.16, and from 0.1 O to 0.16. In further embodiments, the cationic galactomannan having a ratio of galactose to mannose units of about 1 :3 to about 1 :5, preferably about 1 :3 to about 1 :4, including about 1 :3 or about 1 :4, and an average molecular weight lower than 2,500,000 g / mol, the cationic galactomannan can have a DScationic ranging from 0.05 to 0.20, preferably 0.08 to 0.20, more preferably from 0.10 to 0.20, and in certain embodiments the cationic galactomannan can have a DScationic ranging from 0.10 to 0.20, preferably 0.12 to 0.20, more preferably from 0.14 to 0.20. In other embodiments, the cationic galactomannan having a ratio of galactose to mannose units of about 1 :3 to about 1 :5, preferably about 1 :3 to about 1 :4, including about 1 :3 or about 1 :4, and an average molecular weight lower than 2,500,000 g / mol, the cationic galactomannan can have a DScationic preferably ranging from 0.05 to 0.18, preferably 0.08 to 0.18, more preferably from 0.10 to 0.18. In yet other embodiments, the cationic galactomannan having a ratio of galactose to mannose units of about 1 :3 to about 1 :5, preferably about 1 :3 to about 1 :4, including about 1 :3 or about 1 :4, and an average molecular weight lower than 2,500,000 g / mol, the cationic galactomannan can have a DScationic ranging from 0.05 to 0.16, preferably 0.08 to 0.16, more preferably 0.10 to 0.16. In certain embodiments when the cationic galactomannans have a ratio of galactose to mannose units of about 1 :3 to about 1 :5, and preferably have a ratio of galactose to mannose units of about 1 :3 to about 1 :4, including about 1 :3 or about 1 :4, the cationic galactomannans can have a DScationic of 0.18 or lower, preferably lower than 0.18, more preferably lower than 0.16, and the cationic galactomannans can have a biodegradability of 60% or greater within 60 days, preferably within 28 days, in accordance with OECD 301 F.

[0057] Additionally, in certain embodiments when the cationic galactomannans have a ratio of galactose to mannose units of about 1 :3, the cationic galactomannans can have a DScationic of lower than 0.18, preferably 0.17 or lower. Further, in certain embodiments when the cationic galactomannans have a ratio of galactose to mannose units of about 1 :4, the cationic galactomannans can have a DScationic of lower than 0.16, preferably 0.15 or lower.

[0058] In another embodiment, in which the cationic galactomannan has a ratio of galactose to mannose units of about 1 :5, which is commonly referred to as cassia, and an average molecular weight lower than 1 ,000,000 g / mol, the cationic galactomannan can generally have a DScationic of lower than 0.18, preferably 0.16 or lower. In additional embodiments, when the cationic galactomannan has a ratio of galactose to mannose units of about 1 :5 and an average molecular weight lower than 1 ,000,000 g / mol, the cationic galactomannan can have a DScationic of 0.15 or lower, as well as 0.14 or lower. In certain embodiments, cationic galactomannans having a ratio of galactose to mannose units of about 1 :5 and an average molecular weight lower than 1 ,000,000 g / mol, the cationic galactomannan can generally have a DScationic of lower than 0.18, including 0.17 or lower. In this respect, the DScationic can range from 0.001 to lower than 0.18, from 0.01 to lower than 0.18, and from 0.10 to lower than 0.18, as well as from 0.001 to 0.17 or lower, from 0.01 to 0.17 or lower, and from 0.10 to 0.17 or lower, and furthermore, from 0.001 to 0.16 or lower, from 0.01 to 0.16 or lower, and from 0.10 to 0.16 or lower, also including from 0.001 to 0.15 or lower, from 0.01 to 0.15 or lower, and from 0.10 to 0.15 or lower. In other embodiments, the DScationic can range from 0.001 to 0.18, from 0.01 to 0.18, and from 0.10 to 0.18, and furthermore, from 0.001 to 0.16, from 0.01 to 0.16, and from 0.10 to 0.16. In yet other embodiments, the cationic galactomannan having a ratio of galactose to mannose units of about 1 :5 and an average molecular weight lower than 1 ,000,000 g / mol, the cationic galactomannan can have a DScationic ranging from 0.05 to 0.16, including 0.05 to lower than 0.16, preferably 0.08 to 0.16, including 0.08 to lower than 0.16, more preferably 0.10 to 0.16, including 0.10 to lower than 0.16. The DScationic can also range from 0.10 to lower than 0.18, preferably from 0.12 to lower than 0.18 when the cationic galactomannan has a ratio of galactose to mannose units of about 1 :5. In further embodiments, the cationic galactomannan having a ratio of galactose to mannose units of about 1 :5 and an average molecular weight lower than 1 ,000,000 g / mol, the cationic galactomannan can have a DScationic ranging from 0.05 to 0.24, preferably from 0.08 to 0.22, more preferably from 0.10 to 0.20, and in other embodiments the cationic galactomannan having a ratio of galactose to mannose units of about 1 :5 and an average molecular weight lower than 1 ,000,000 g / mol, the cationic galactomannan can have a DScationic ranging from 0.10 to lower than 0.24, preferably from 0.14 to 0.22, more preferably from 0.14 to 0.20. In certain embodiments when the cationic galactomannans have a ratio of galactose to mannose units of about 1 :5, the cationic galactomannans can have a DScationic of lower than 0.18, preferably lower than 0.16, and the cationic galactomannans can have a biodegradability of 60% or greater within 60 days, preferably within 28 days, in accordance with OECD 301 F.

[0059] 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 HCI 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.

[0060] As used herein, the terms “cationic degree of substitution” and “DScationic” are interchangeable and are synonymous, and refer to the cationic degree of substitution measured after an acidic methanol extraction step. Additionally, the DScationic means the average number of moles of cationic groups or moieties per mole of sugar unit, which can be measured by1H-NMR (solvent: D2O). Once the1H NMR spectrum is obtained, the integration of the multiplet of peaks corresponding to the anomeric proton on all the galactomannan units, usually between about 3.5- 5.5 ppm, is normalized to unity. The peak of interest, the one corresponding to the methyl protons of the quaternary ammonium group on the galactomannan units, is centered at about 3-3.5 ppm. This peak is integrated for 9 protons given that there are 3 methyl groups on the ammonium function. Therefore, as an example, the calculation of the (DScationic) for the case of the cationizing agent 2,3- epoxypropyltrimethylammonium chloride is as follows:

[0061] Any presence of residual cationizing agent(s), by-products of any unreacted cationizing agent(s), or mixtures thereof may be evidenced by smaller peaks in the1H-NMR spectra at lower field than the peak of interest, which is centered at about 3-3.5 ppm.

[0062] 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 / H Ciconcentrated 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 brining 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 non-cellulosic polysaccharide derivative is then dried and ground before1H-NMR analysis.

[0063] In other embodiments, cationization of the galactomannan can also be expressed in terms of charge density. As used herein, the term “charge density” refers to the ratio of positive charges on the monomeric unit of which the galactomannan is comprised of to the molecular weight of the monomeric unit. The charge density multiplied by the polymer molecular weight determines the number of positively charged sites on a given polymer chain. The cationic degree of substitution may be converted to charge density through several methods. In a particular embodiment, the method for calculating charge density of cationic galactomannans uses a method that specifically quantifies the equivalents of the cationic groups or moieties, preferably the quaternary ammonium groups, on the galactomannan. In an non-limiting example, for cationic galactomannans obtained by reacting a galactomannan with 3-chloro-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:

[0064] Cationic charge density in mequivalents per gram (meq / g) = - -x 1ooo 162 + 151 x DS U„d„ti

[0065] In general, the equation above depends on the group that is grafted to the galactomannan.

[0066] In certain embodiments, the galactomannan has a charge density after the acidic methanol extraction step of from about 1 .0 to about 2 meq / g, preferably from about 1 .1 to about 1 .8 meq / g, more preferably from 1 .2 to 1 .5 meq / g.

[0067] 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) of at least about 3,500 g / mol, including at least about 5,000 g / mol, and in certain embodiments at least about 10,000 g / mol. The cationic galactomannans of the present invention can also generally have an average molecular weight (Mw) up to about 10,000,000 g / mol, up to about 7,500,000 g / mol, including up to about 5,000,000 g / mol. In certain embodiments, the cationic galactomannans can generally have an average molecular weight (Mw) ranging from 20,000 g / mol to 10,000,000 g / mol, preferably from 50,000 g / mol to 7,500,000 g / mol, more preferably from 100,000 g / mol to 5,000,000 g / mol. In certain embodiments in which the cationic galactomannan has a ratio of galactose to mannose units of about 1 :1 , which is commonly referred to as fenugreek, the cationic galactomannan can generally have an average molecular weight (Mw) lower than 3,500,000 g / mol, including 3,000,000 g / mol or lower. In other embodiments, when the cationic galactomannan has a ratio of galactose to mannose units of about 1 :1 , the cationic galactomannan can have an average molecular weight (Mw) ranging from 200,000 g / mol to 3,000,000 g / mol, more preferably ranging from 250,000 g / mol to 2,500,000 g / mol, and even more preferably ranging from 500,000 g / mol to 2,500,000 g / mol.

[0068] In further embodiments, when the cationic galactomannan has a ratio of galactose to mannose units of about 1 :3 to about 1 :5, which are commonly referred to as tara, locust bean or carob, and cassia, the cationic galactomannans can generally have an average molecular weight (Mw) lower than 2,500,000 g / mol. In certain preferred embodiments, the cationic galactomannans can have a ratio of galactose to mannose units of about 1 :3 to about 1 :4, including about 1 :3 or about 1 :4, with an average molecular weight (Mw) lower than 2,500,000 g / mol, including 2,000,000 g / mol or lower. In yet other embodiments in which the cationic galactomannan have a ratio of galactose to mannose units of about 1 :3 to about 1 :5, the cationic galactomannan can have an average molecule weight (Mw) ranging from 200,000 g / mol to 2,000,000 g / mol, more preferably ranging from 250,000 g / mol to 2,000,000 g / mol, even more preferably ranging from 300,000 g / mol to 2,000,000 g / mol.

[0069] Additionally, in another embodiment when the cationic galactomannan has a ratio of galactose to mannose units of about 1 :5, which as noted above is commonly referred to as cassia, the cationic galactomannan can generally have an average molecular weight (Mw) lower than 1 ,000,000 g / mol. Moreover, when the cationic galactomannan has a ratio of galactose to mannose units of about 1 :5, the cationic galactomannan can generally have an average molecular weight (Mw) ranging from 900,000 g / mol or lower, preferably from about 100,000 g / mol to 900,000 g / mol, more preferably about 150,000 g / mol to 800,000 g / mol, including more preferably about 150,000 g / mol to 750,000 g / mol.

[0070] As used herein, the terms “average molecular weight,” “molecular weight,” and “(Mw),” are interchangeable and are synonymous and all mean the same thing as weight average molecular weight. The average molecular weight is measured by SEC-MALS (Size Exclusion Chromatography with detection by Multi-Angle Light- Scattering detection) with a Shodex Pack SB-806 M HQ column. A value of 0.140 for dn / dc is used for the molecular weight measurements. An Agilent Refractive Index Detector and WYATT miniDawn is calibrated using a 22.5 KDa polyethylene glycol standard. All calculations of the molecular weight distributions are performed using Wyatt’s ASTRA software. The samples are prepared as 0.05% solutions in the mobile phase (100 mM Na2NO3, 200 ppm NaNs, 20 ppm pDADMAC, 100 ppm sodium azide) and filtered through 0.45 pm PVDF filters before analysis. The average molecular weights are expressed by weight.

[0071] As discussed above, the cationic galactomannans of the present invention are biodegradable. And to this point, it has been unexpectedly found that cationic galactomannans having certain DScationic values in combination with certain average molecular weights (Mw) can demonstrate sufficient biodegradability properties. In this respect, the cationic galactomannans of the present invention are considered biodegradable under OECD 301 , and in particular are considered biodegradable under OECD 301 F. Specifically, OECD 301 F provides testing guidelines for determining whether a chemical substance is considered biodegradable, including readily biodegradable. In certain embodiments, the cationic galactomannan has a biodegradability of 60% or greater within 60 days in accordance with OECD 301 F. In further embodiments, the cationic galactomannan has a biodegradability of 60% or greater within 28 days in accordance with OECD 301 F. In other embodiments, the cationic galactomannan has a biodegradability of 70% or greater within 60 days, and more preferably within 28 days, when tested in accordance with the methodology of OECD 301 F. That is, in certain embodiments, the cationic galactomannans can have a biodegradability that is higher than 60%, including 70% or greater, within 60 days of testing, including within 28 days of testing, in accordance with the testing methodology of OECD 301 F.

[0072] The cationic galactomannans can be made in a number of ways. To begin, the galactomannans in their unmodified native (or gum forms), which are used to make the chemically modified and functionalized cationic galactomannans can be sourced from their respective seeds. For instance, the galactomannans can be extracted from the endosperm of the seeds. Thereafter, the galactomannans can be cationically functionalized by reacting the galactomannans with at least one cationizing agents. In general, the cationic galactomannans of the present invention can be made by reacting a non-cationic galactomannan with at least one cationizing agent. Noncationic galactomannans include galactomannans in their respective native form, as well as galactomannans that may have undergone a chemical pre-treatment step. In certain embodiments, the cationic galactomannan of the present invention can be made by reacting a chemically unmodified galactomannan with at least one cationizing agent. In such embodiments, the galactomannans can be in their respective native forms ( / .e., gum forms). As a non-limiting example, galactomannans having repeating residues of formula (I), as shown above, can be used to make cationic galactomannans having repeating residues of formula (III), formula (V), or combinations thereof, as shown above. In other embodiments, the cationic galactomannans can be made by reacting a non-cationic galactomannan with at least one cationizing agent, in which the non-cationic galactomannan is optionally chemically modified prior to being cationized.

[0073] In general, the cationization process can be carried out in a reaction medium having an aqueous solution, at least one cationizing agent, the galactomannan, and at least one base. Preferred bases include, but are not limited to alkali metal hydroxides, such as sodium hydroxide, ammonium hydroxide, and combinations thereof. The base can be present in excess, which can catalyze the reaction. In certain embodiments, the base can be present from about 0.01 to about 25 wt. %, more preferably from about 0.05 to about 20 wt. %, based on the galactomannan wt. % in the reaction.

[0074] The aqueous solution can have at least one solvent, including at least one organic water-miscible solvent. The organic water-miscible solvent can be selected from alkanols, glycols, cyclic and acylic alkyl ethers, alkanones, dialkylformamide, and mixtures thereof. Non-limiting organic water-miscible solvents include methanol, ethanol, propanol, including isopropanol, butanol, pentanol, including secondary pentanol, ethyleneglycol, acetone, methylethylketone, diethylketone, tetrahydrofuran, dioxane, dimethylformamide, and mixtures thereof. In certain embodiments, the amount of the organic water-miscible solvent can be present from about 1 to about 20 wt. %, preferably from about 1 to about 10 wt. %. In other embodiments, the weight ratio of the organic water-miscible solvent to the galactomannan is about 10 to 1 , preferably about 5 to 1 . The cationization process can be conducted at a temperature ranging from about 10° C to about 100° C, preferably ranging from about 20° C to about 80° C. The reaction time can range from about 1 to about 8 hours, and preferably from about 1 to about 6 hours. The cationizing process can be conducted in a variety of equipment and vessels, including open or closed vessels or reactors equipped with stirrers in batch or continuous operation.

[0075] Further, after functionalizing the galactomannans by reacting the unmodified native galactomannan ( / .e., the galactomannan gum) with at least one cationizing agent, the cationic galactomannans can undergo at least one chemical posttreatment step. In certain embodiments, after the cationization process, the cationic galactomannans can be chemically post-treated to remove and / or neutralize any unreacted reactants, including any unreacted or partially reacted cationizing agents, and to remove any water-miscible solvents. Non-limiting examples of chemical posttreatments including at least one washing step (with water), crosslinking with borates, at least one alkaline treatment step, at least one acid addition step, and combinations thereof. For example, after functionalizing the galactomannans by reacting the unmodified native galactomannan with at least one cationizing agent, the cationic galactomannans can be chemically post-treated with borates, washed with water, or both. In another embodiment, the cationic galactomannans can be chemically post-treated with an alkali treatment step, washed with water, or both. In embodiments using an alkali treatment step, alkali metal hydroxides, such as sodium hydroxide, ammonium hydroxide, and combinations thereof can be used. Further, in embodiments using an alkali treatment step, the pH can be adjusted as needed to a neutral or acid pH using at least one acid, including at least one inorganic acid, at least one organic acid, and mixtures thereof. Non-limiting acids include, but are not limited to hydrochloric acid, sulfuric acid, acetic acid, lactic acid, citric acid, carbon dioxide, fumaric acid, and mixtures thereof.

[0076] After the cationic galactomannan is obtained from the cationization process, including any chemical post-treatment steps, the cationic galactomannan can be dried and further processed mechanically, such as milling the cationic galactomannan.

[0077] The biodegradable cationic galactomannans of the present invention can be used in a variety of compositions and applications. For instance, the biodegradable cationic galactomannans can be used as a conditioning agent, suspending agent, thickener or rheology modifier, film forming agent, or combinations thereof. In certain embodiments, the biodegradable cationic galactomannans can be used in home and personal care compositions, as well as in cleaning and disinfectant compositions. In certain embodiments, the biodegradable cationic galactomannans can be used in hair care, skin care, and cosmetic compositions, such as but not limited to shampoos, hair conditioners, body washes, soaps, facial washes, makeup, lotions, skin creams, skin conditioners, balms, hair gels, sunscreen compositions, and similar compositions. In other embodiments, the biodegradable cationic galactomannan can be used in laundry or fabric detergents, softeners, and conditioners, as well as in hard surface cleaning compositions, such as sprays, wipes, aerosols, gels, bars, and similar compositions.

[0078] Depending on the composition and application, in addition to the biodegradable cationic galactomannan, the composition may contain various other convention components and additives known in the respective art. For example, the compositions having the biodegradable cationic galactomannans can further have at least one surfactant, emulsifier, emollient, moisturizer, hair conditioning agent, hair fixative, film-former, skin protectant, binder, chelating agent, disinfectant, insecticide, fungicide, deodorant, pest repellant, odoriferous material, antimicrobial agent, antifungal agent, antibiotic, antidandruff agent, abrasive, adhesive, absorbent, colorant, deodorant, antiperspirant agent, humectant, oil (such as a mineral oil, a vegetable oil, an animal oil, a synthetic oil, a silicone oil and mixtures thereof), opacifying and pearlescing agent, antioxidant, preservative, propellant, spreading agent, exfoliant, keratolytic agent, blood coagulant, vitamin, sunscreen agent, artificial tanning accelerator, ultraviolet light absorber, pH adjusting agent, botanical, hair colorant, dye, preservative, inorganic particles, buffers, preservatives, oxidizing agents, reducing agent, rheology modifier, skin bleaching agent, pigment, anti-inflammatory agent, thickening agent, topical anesthetic, fragrance, fragrance solubilizer, particulate, microabrasive, and combinations thereof.

[0079] EXAMPLES The following examples are illustrative of preferred embodiments of cationic galactomannans and methods for making the same, and are not intended to be limitations thereon. All composition percentages are based on totals equal to 100% by weight, unless otherwise specified.

[0080] Test Methods

[0081] Molecular Weight

[0082] The average molecular weight of the cationic galactomannans were measured by SEC-MALS (Size Exclusion Chromatography with Multi-Angle Light- Scattering detection) with a Shodex Pack SB-806 M HQ column, as described above. The measurements were conducted at ambient temperature with a run time of 50 minutes, and the flow rate was 1 .0 mL / min.

[0083] Cationic Degree of Substitution

[0084] The cationic degree of substitution of the cationic galactomannans were measured by1H-NMR (solvent: D2O), as described above.

[0085] Biodegradability

[0086] The biodegradability of the cationic galactomannans were measured in accordance with OECD 301 F. 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 in accordance with OECD 301 F.

[0087] Example 1 - Biodegradable Cationic Fenugreek

[0088] In a 1 Liter stirred reactor, 280.0 g of isopropanol solvent mixed with 110.0 g of de-ionized water were introduced at room temperature, under a blanket of inert nitrogen gas. 125.0 g of fenugreek powder was then loaded at room temperature and under vigorous stirring. After a few minutes of stirring to allow for homogenization, 47.1 g of 3-chloro-2-hydroxypropyltrimethyl ammonium chloride (Quat188, 65% in water) was added. This reagent was left to mix at room temperature with the fenugreek dispersion for 30 minutes, after which 18.0 g of sodium hydroxide (50% in water) was slowly added. This reagent was left to mix at room temperature with the fenugreek 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.

[0089] A reaction mixture obtained as described in the paragraph above was dispersed under stirring with 158.0 g of isopropanol (99%) and 44.0 g of water. The pH was adjusted to approximately 9-10 using 1 .4 g of glacial acetic acid. The mixture was then left under stirring for 30 minutes and then discharged from the reactor after settling. This dispersion was then filtered under vacuum through qualitative filter paper. This washing and filtering procedure was repeated one more time for 30 minutes with 356 g of isopropanol (99%) and 145 g of water. The obtained solid was then let dry overnight for 6 hours in an oven at 60°C.

[0090] The cationic degree of substitution (DScationic) was 0.12 and the average molecular weight (Mw) was 1 ,626,000 g / mol. The cationic fenugreek was tested for biodegradability and it demonstrated that it was readily biodegradable within 28 and within 60 days (7.e. , passed).

[0091] Example 2 - Biodegradable Cationic Fenugreek

[0092] In a 1 Liter stirred reactor, 196.7 g of isopropanol solvent mixed with 75.2 g of de-ionized water were introduced at room temperature, under a blanket of inert nitrogen gas. 87.5 g of fenugreek powder was then loaded at room temperature and under vigorous stirring. After a few minutes of stirring to allow for homogenization, 45.0 g of 3-chloro-2-hydroxypropyltrimethyl ammonium chloride (Quat188, 65% in water) was added. This reagent was left to mix at room temperature with the fenugreek dispersion for 30 minutes, after which 15.4 g of sodium hydroxide (50% in water) was slowly added. This reagent was left to mix at room temperature with the fenugreek 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.

[0093] A reaction mixture obtained as described in the paragraph above was dispersed under stirring with 112.0 g of isopropanol (99%) and 23.0 g of water. The pH was adjusted to approximately 9-10 using 4.1 g of glacial acetic acid. The mixture was then left under stirring for 30 minutes and then discharged from the reactor after settling. This dispersion was then filtered under vacuum through qualitative filter paper. This washing and filtering procedure was repeated one more time for 30 minutes with 250 g of isopropanol (99%) and 100 g of water. The obtained solid was then let dry overnight for 6 hours in an oven at 60°C.

[0094] The cationic degree of substitution (DScationic) was 0.13 and the average molecular weight (Mw) was 2,020,000 g / mol. The cationic fenugreek was tested for biodegradability and it demonstrated that it was readily biodegradable within 60 days ( / .e., passed).

[0095] Example 3 - Biodegradable Cationic Fenugreek

[0096] In a 1 Liter stirred reactor, 195.5 g of isopropanol solvent mixed with 74.8 g of de-ionized water were introduced at room temperature, under a blanket of inert nitrogen gas. 87.8 g of fenugreek powder was then loaded at room temperature and under vigorous stirring. After a few minutes of stirring to allow for homogenization, 45.0 g of 3-chloro-2-hydroxypropyltrimethyl ammonium chloride (Quat188, 65% in water) was added. This reagent was left to mix at room temperature with the fenugreek dispersion for 30 minutes, after which 15.4 g of sodium hydroxide (50% in water) was slowly added. This reagent was left to mix at room temperature with the fenugreek 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.

[0097] A reaction mixture obtained as described in the paragraph above was dispersed under stirring with 110.5 g of isopropanol (99%) and 22.9 g of water. The pH was adjusted to approximately 9-10 using 4.1 g of glacial acetic acid. The mixture was then left under stirring for 30 minutes and then discharged from the reactor after settling. This dispersion was then filtered under vacuum through qualitative filter paper. This washing and filtering procedure was repeated one more time for 30 minutes with 250 g of isopropanol (99%) and 100 g of water. The obtained solid was then let dry overnight for 6 hours in an oven at 60°C.

[0098] The cationic degree of substitution (DScationic) was 0.15 and the average molecular weight (Mw) was 1 ,384,000 g / mol. The cationic fenugreek was tested for biodegradability and it demonstrated that it was readily biodegradable within 60 days ( / .e., passed). Comparative Example 1 - Non-biodegradable Cationic Fenugreek

[0099] In a 1 Liter stirred reactor, 195.5 g of isopropanol solvent mixed with 74.8 g of de-ionized water were introduced at room temperature, under a blanket of inert nitrogen gas. 87.8 g of fenugreek powder was then loaded at room temperature and under vigorous stirring. After a few minutes of stirring to allow for homogenization, 45.0 g of 3-chloro-2-hydroxypropyltrimethyl ammonium chloride (Quat188, 65% in water) was added. This reagent was left to mix at room temperature with the fenugreek dispersion for 30 minutes, after which 17.0 g of sodium hydroxide (50% in water) was slowly added. This reagent was left to mix at room temperature with the fenugreek 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.

[0100] A reaction mixture obtained as described in the paragraph above was dispersed under stirring with 110.5 g of isopropanol (99%) and 22.7 g of water. The pH was adjusted to approximately 9-10 using 2.0 g of glacial acetic acid. The mixture was then left under stirring for 30 minutes and then discharged from the reactor after settling. This dispersion was then filtered under vacuum through qualitative filter paper. This washing and filtering procedure was repeated one more time for 30 minutes with 250 g of isopropanol (99%) and 100 g of water. The obtained solid was then let dry overnight for 6 hours in an oven at 60°C.

[0101] The cationic degree of substitution (DScationic) was 0.17 and the average molecular weight (Mw) was 1 ,696,000 g / mol. The cationic fenugreek was tested for biodegradability and it demonstrated that it was not readily biodegradable within 60 days ( / .e., failed).

[0102] The results for Examples 1 - 3 and Comparative Example 1 are shown below in Table 1 .

[0103] Table 1 : Cationic Fenugreeks

[0104] As shown above in Table 1 , cationic fenugreeks having a cationic degree of substitution lower than 0.17 demonstrate superior biodegradability versus cationic fenugreeks having a cationic degree of substitution of 0.17 or higher.

[0105] Example 4 - Biodegradable Cationic Tara

[0106] In a 1 Liter stirred reactor, 98.7 g of isopropanol solvent mixed with 37.4 g of de-ionized water were introduced at room temperature, under a blanket of inert nitrogen gas. 43.8 g of tara gum powder was then loaded at room temperature and under vigorous stirring. After a few minutes of stirring to allow for homogenization, 18.5 g of 3-chloro-2-hydroxypropyltrimethyl ammonium chloride (Quat188, 65% in water) was added. This reagent was left to mix at room temperature with the tara gum dispersion for 30 minutes, after which 7.1 g of sodium hydroxide (50% in water) was slowly added. This reagent was left to mix at room temperature with the tara gum 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.

[0107] A reaction mixture obtained as described in the paragraph above was dispersed under stirring with 55.2 g of isopropanol (99%) and 12.0 g of water. The pH was adjusted to approximately 9-10 using 1 .0 g of glacial acetic acid. The mixture was then left under stirring for 30 minutes and then discharged from the reactor after settling. This dispersion was then filtered under vacuum through qualitative filter paper. This washing and filtering procedure was repeated one more time for 30 minutes with 125 g of isopropanol (99%) and 50 g of water. The obtained solid was then let dry overnight for 6 hours in an oven at 60°C.

[0108] The cationic degree of substitution (DScationic) was 0.14 and the average molecular weight (Mw) was 1 , 167,000 g / mol. The cationic tara was tested for biodegradability and it demonstrated that it was readily biodegradable within 28 and within 60 days ( / .e., passed).

[0109] Example 5 - Biodegradable Cationic Tara

[0110] In a 1 Liter stirred reactor, 195.9 g of isopropanol solvent mixed with 74.8 g of de-ionized water were introduced at room temperature, under a blanket of inert nitrogen gas. 87.6 g of tara gum powder was then loaded at room temperature and under vigorous stirring. After a few minutes of stirring to allow for homogenization, 45.3 g of 3-chloro-2-hydroxypropyltrimethyl ammonium chloride (Quat188, 65% in water) was added. This reagent was left to mix at room temperature with the tara gum dispersion for 30 minutes, after which 16.2 g of sodium hydroxide (50% in water) was slowly added. This reagent was left to mix at room temperature with the tara gum 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.

[0111] A reaction mixture obtained as described in the paragraph above was dispersed under stirring with 119.0 g of isopropanol (99%) and 23.0 g of water. The pH was adjusted to approximately 9-10 using 4.1 g of glacial acetic acid. The mixture was then left under stirring for 30 minutes and then discharged from the reactor after settling. This dispersion was then filtered under vacuum through qualitative filter paper. This washing and filtering procedure was repeated one more time for 30 minutes with 250 g of isopropanol (99%) and 100 g of water. The obtained solid was then let dry overnight for 6 hours in an oven at 60°C.

[0112] The cationic degree of substitution (DScationic) was 0.17 and the average molecular weight (Mw) was 1 ,057,000 g / mol. The cationic tara was tested for biodegradability and it demonstrated that it was readily biodegradable within 60 days ( / .e., passed). Comparative Example 2 - Non-biodeqradable Cationic Tara

[0113] In a 1 Liter stirred reactor, 97.4 g of isopropanol solvent mixed with 39.0 g of de-ionized water were introduced at room temperature, under a blanket of inert nitrogen gas. 43.8 g of tara gum powder was then loaded at room temperature and under vigorous stirring. After a few minutes of stirring to allow for homogenization, 27.8 g of 3-chloro-2-hydroxypropyltrimethyl ammonium chloride (Quat188, 65% in water) was added. This reagent was left to mix at room temperature with the tara gum dispersion for 30 minutes, after which 11.0 g of sodium hydroxide (50% in water) was slowly added. This reagent was left to mix at room temperature with the tara gum 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.

[0114] A reaction mixture obtained as described in the paragraph above was dispersed under stirring with 110.0 g of isopropanol (99%) and 23.0 g of water. The pH was adjusted to approximately 9-10 using 1 .6 g of glacial acetic acid. The mixture was then left under stirring for 30 minutes and then discharged from the reactor after settling. This dispersion was then filtered under vacuum through qualitative filter paper. This washing and filtering procedure was repeated one more time for 30 minutes with 250 g of isopropanol (99%) and 100 g of water. The obtained solid was then let dry overnight for 6 hours in an oven at 60°C.

[0115] The cationic degree of substitution (DScationic) was 0.20 and the average molecular weight (Mw) was 1 ,020,000 g / mol. The cationic tara was tested for biodegradability and it demonstrated that it was not readily biodegradable within 60 days ( / .e., failed).

[0116] Comparative Example 3 - Non-biodeqradable Cationic Tara

[0117] In a 1 Liter stirred reactor, 140.1 g of isopropanol solvent mixed with 55.2 g of de-ionized water were introduced at room temperature, under a blanket of inert nitrogen gas. 63.0 g of tara gum powder was then loaded at room temperature and under vigorous stirring. After a few minutes of stirring to allow for homogenization, 32.5 g of 3-chloro-2-hydroxypropyltrimethyl ammonium chloride (Quat188, 65% in water) was added. This reagent was left to mix at room temperature with the tara gum dispersion for 30 minutes, after which 12.5 g of sodium hydroxide (50% in water) was slowly added slowly. This reagent was left to mix at room temperature with the tara gum 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.

[0118] A reaction mixture obtained as described in the paragraph above was dispersed under stirring with 79.8 g of isopropanol (99%) and 16.8 g of water. The pH was adjusted to approximately 9-10 using 1 .9 g of glacial acetic acid. The mixture was then left under stirring for 30 minutes and then discharged from the reactor after settling. This dispersion was then filtered under vacuum through qualitative filter paper. This washing and filtering procedure was repeated one more time for 30 minutes with 180 g of isopropanol (99%) and 72 g of water. The obtained solid was then let dry overnight for 6 hours in an oven at 60°C.

[0119] The cationic degree of substitution (DScationic) was 0.18 and the average molecular weight (Mw) was 1 ,490,000 g / mol. The cationic tara was tested for biodegradability and it demonstrated that it was not readily biodegradable within 60 days ( / .e., failed).

[0120] Comparative Example 4 - Non-biodeqradable Cationic Tara

[0121] In a 1 Liter stirred reactor, 195.9 g of isopropanol solvent mixed with 74.8 g of de-ionized water were introduced at room temperature, under a blanket of inert nitrogen gas. 87.8 g of tara gum powder was then loaded at room temperature and under vigorous stirring. After a few minutes of stirring to allow for homogenization, 65.8 g of 3-chloro-2-hydroxypropyltrimethyl ammonium chloride (Quat188, 65% in water) was added. This reagent was left to mix at room temperature with the tara gum dispersion for 30 minutes, after which 23.5 g of sodium hydroxide (50% in water) was slowly added. This reagent was left to mix at room temperature with the tara gum dispersion and the cationic etherifying agent for 15 m inutes. 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 in the paragraph above was dispersed under stirring with 110.0 g of isopropanol (99%) and 23.0 g of water. The pH was adjusted to approximately 9-10 using 2.5 g of glacial acetic acid. The mixture was then left under stirring for 30 minutes and then discharged from the reactor after settling. This dispersion was then filtered under vacuum through qualitative filter paper. This washing and filtering procedure was repeated one more time for 30 minutes with 250 g of isopropanol (99%) and 100 g of water. The obtained solid was then let dry overnight for 6 hours in an oven at 60°C.

[0122] The cationic degree of substitution (DScationic) was 0.25 and the average molecular weight (Mw) was 1 , 195,000 g / mol. The cationic tara was tested for biodegradability and it demonstrated that it was not readily biodegradable within 60 days ( / .e., failed).

[0123] Comparative Example 5 - Non-biodeqradable Cationic Tara

[0124] In a 1 Liter stirred reactor, 97.8 g of isopropanol solvent mixed with 37.3 g of de-ionized water were introduced at room temperature, under a blanket of inert nitrogen gas. 43.4 g of tara gum powder was then loaded at room temperature and under vigorous stirring. After a few minutes of stirring to allow for homogenization, 45.1 g of 3-chloro-2-hydroxypropyltrimethyl ammonium chloride (Quat188, 65% in water) was added. This reagent was left to mix at room temperature with the tara gum dispersion for 30 minutes, after which 11.1 g of sodium hydroxide (50% in water) was slowly added. This reagent was left to mix at room temperature with the tara gum 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.

[0125] A reaction mixture obtained as described in the paragraph above was dispersed under stirring with 110.0 g of isopropanol (99%) and 23.0 g of water. The pH was adjusted to approximately 9-10 using 1 .0 g of glacial acetic acid. The mixture was then left under stirring for 30 minutes and then discharged from the reactor after settling. This dispersion was then filtered under vacuum through qualitative filter paper. This washing and filtering procedure was repeated one more time for 30 minutes with 250 g of isopropanol (99%) and 100 g of water. The obtained solid was then let dry overnight for 6 hours in an oven at 60°C.

[0126] The cationic degree of substitution (DScationic) was 0.29. The cationic tara was tested for biodegradability and it demonstrated that it was not readily biodegradable within 60 days (7.e. , failed).

[0127] The results for Examples 4 and 5, and Comparative Examples 2 - 5 are shown below in Table 2.

[0128] Table 2: Cationic Taras

[0129] As shown above in Table 2, cationic taras having a cationic degree of substitution lower than 0.18 demonstrate superior biodegradability versus cationic fenugreeks having a cationic degree of substitution of 0.18 or higher.

[0130] Example 6 - Biodegradable Cationic Cassia

[0131] In a 1 Liter stirred reactor, 195.1 g of isopropanol solvent mixed with 74.0 g of de-ionized water were introduced at room temperature, under a blanket of inert nitrogen gas. 87.6 g of cassia powder was then loaded at room temperature and under vigorous stirring. After a few minutes of stirring to allow for homogenization, 28.1 g of 3-chloro-2-hydroxypropyltrimethyl ammonium chloride (Quat188, 65% in water) was added. This reagent was left to mix at room temperature with the cassia dispersion for 30 minutes, after which 15.1 g of sodium hydroxide (50% in water) was slowly added. This reagent was left to mix at room temperature with the cassia 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.

[0132] A reaction mixture obtained as described in the paragraph above was dispersed under stirring with 110.0 g of isopropanol (99%) and 23.0 g of water. The pH was adjusted to approximately 9-10 using 3.9 g of glacial acetic acid. The mixture was then left under stirring for 30 minutes and then discharged from the reactor after settling. This dispersion was then filtered under vacuum through qualitative filter paper. This washing and filtering procedure was repeated one more time for 30 minutes with 250 g of isopropanol (99%) and 100 g of water. The obtained solid was then let dry overnight for 6 hours in an oven at 60°C.

[0133] The cationic degree of substitution (DScationic) was 0.13 and the average molecular weight (Mw) was 563,000 g / mol. The cationic cassia was tested for biodegradability and it demonstrated that it was readily biodegradable within 28 and within 60 days (7.e. , passed).

[0134] Comparative Example 6 - Non-biodeqradable Cationic Cassia

[0135] In a 1 Liter stirred reactor, 144.0 g of isopropanol solvent mixed with 55.0 g of de-ionized water were introduced at room temperature, under a blanket of inert nitrogen gas. 62.5 g of cassia powder was then loaded at room temperature and under vigorous stirring. After a few minutes of stirring to allow for homogenization, 32.0 g of 3-chloro-2-hydroxypropyltrimethyl ammonium chloride (Quat188, 65% in water) was added. This reagent was left to mix at room temperature with the cassia dispersion for 30 minutes, after which 11.8 g of sodium hydroxide (50% in water) was slowly added. This reagent was left to mix at room temperature with the cassia 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.

[0136] A reaction mixture obtained as described in the paragraph above was dispersed under stirring with 90.0 g of isopropanol (99%) and 15.0 g of water. The pH was adjusted to approximately 9-10 using 3.9 g of glacial acetic acid. The mixture was then left under stirring for 30 minutes and then discharged from the reactor after settling. This dispersion was then filtered under vacuum through qualitative filter paper. This washing and filtering procedure was repeated one more time for 30 minutes with 180 g of isopropanol (99%) and 70 g of water. The obtained solid was then let dry overnight for 6 hours in an oven at 60°C.

[0137] The cationic degree of substitution (DScationic) was 0.18 and the average molecular weight (Mw) was 743,000 g / mol. The cationic cassia was tested for biodegradability and it demonstrated that it was not readily biodegradable within 60 days (7.e. , failed).

[0138] Comparative Example 7 - Non-biodeqradable Cationic Cassia

[0139] In a 1 Liter stirred reactor, 195.6 g of isopropanol solvent mixed with 74.9 g of de-ionized water were introduced at room temperature, under a blanket of inert nitrogen gas. 87.7 g of cassia powder was then loaded at room temperature and under vigorous stirring. After a few minutes of stirring to allow for homogenization, 65.0 g of 3-chloro-2-hydroxypropyltrimethyl ammonium chloride (Quat188, 65% in water) was added. This reagent was left to mix at room temperature with the cassia dispersion for 30 minutes, after which 12.6 g of sodium hydroxide (50% in water) was slowly added. This reagent was left to mix at room temperature with the cassia 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.

[0140] A reaction mixture obtained as described in the paragraph above was dispersed under stirring with 100.0 g of isopropanol (99%) and 25.0 g of water. The pH was adjusted to approximately 9-10 using 2.0 g of glacial acetic acid. The mixture was then left under stirring for 30 minutes and then discharged from the reactor after settling. This dispersion was then filtered under vacuum through qualitative filter paper. This washing and filtering procedure was repeated one more time for 30 minutes with 250 g of isopropanol (99%) and 100 g of water. The obtained solid was then let dry overnight for 6 hours in an oven at 60°C.

[0141] The cationic degree of substitution (DScationic) was 0.24 and the average molecular weight (Mw) was 757,000 g / mol. The cationic cassia was tested for biodegradability and it demonstrated that it was not readily biodegradable within 60 days (i.e., failed).

[0142] The results for Example 6 and Comparative Examples 6 and 7 are shown below in Table 3.

[0143] Table 3: Cationic Cassia

[0144] As shown above in Table 3, cationic cassias having a cationic degree of substitution of lower than 0.18 demonstrate superior biodegradability versus cationic cassias having a cationic degree of substitution of 0.18 or higher.

[0145] The present subject matter being thus described, it will be apparent that the same may be modified or varied in many ways. Such modifications and variations are not to be regarded as a departure from the spirit and scope of the present subject matter, and all such modifications and variations are intended to be included within the scope of the following claims.

Claims

CLAIMS1. A biodegradable cationic galactomannan comprising a ratio of galactose to mannose units of about 1 :1 , the cationic galactomannan having:(a) a DScationic of lower than 0.17, preferably 0.16 or lower, more preferably 0.15 or lower; and(b) an average molecular weight (Mw) lower than 3,500,000 g / mol, wherein the cationic galactomannan has a biodegradability of 60% or greater within 60 days in accordance with OECD 301 F.

2. The biodegradable cationic galactomannan of claim 1 , wherein the cationic galactomannan comprises cationic fenugreek (Trigonella foenum-graecum).

3. The biodegradable cationic galactomannan of any of the preceding claims, wherein the DScationic ranges from 0.10 to 0.16, preferably from 0.12 to 0.16, more preferably from 0.14 to 0.16.

4. The biodegradable cationic galactomannan of any of the preceding claims, wherein the Mw is 3,000,000 g / mol or lower, preferably ranges from 200,000 g / mol to 3,000,000 g / mol, more preferably ranges from 250,000 g / mol to 2,500,000 g / mol, even more preferably ranges from 500,000 g / mol to 2,500,000 g / mol.

5. A biodegradable cationic galactomannan comprising a ratio of galactose to mannose units of about 1 :3 to about 1 :5, preferably about 1 :3 to about 1 :4, the cationic galactomannan having:(a) a DScationic of lower than 0.18, preferably 0.17 or lower; and(b) an average molecular weight (Mw) lower than 2,500,000 g / mol, wherein the cationic galactomannan has a biodegradability of 60% or greater within 60 days in accordance with OECD 301 F.

6. The biodegradable cationic galactomannan of claim 5, wherein the cationic galactomannan comprises cationic tara (Tara spinosa), cationic locust bean (Parkia biglobosa), or combinations thereof.

7. The biodegradable cationic galactomannan of claim 5, wherein the cationic galactomannan comprises a ratio of galactose to mannose units of about 1 :4 having a DScationic of lower than 0.16, preferably 0.15 or lower.

8. The biodegradable cationic galactomannan of claim 5, wherein the cationic galactomannan comprises a ratio of galactose to mannose units of about 1 :3 having a DScationic of lower than 0.18, preferably 0.17 or lower.

9. The biodegradable cationic galactomannan of claims 5 or 6, wherein the DScationic ranges from 0.10 to 0.20, preferably 0.12 to 0.20, more preferably from 0.14 to 0.20.

10. The biodegradable cationic galactomannan of claims 5 - 9, wherein the Mw is 2,000,000 g / mol or lower, preferably ranges from 200,000 g / mol to 2,000,000 g / mol, more preferably ranges from 250,000 g / mol to 2,000,000 g / mol, even more preferably ranges from 300,000 g / mol to 2,000,000 g / mol.

11. A biodegradable cationic galactomannan comprising a ratio of galactose to mannose units of about 1 :5, the cationic galactomannan having:(a) a DScationic of lower than 0.18; and(b) an average molecular weight (Mw) lower than 1 ,000,000 g / mol, wherein the cationic galactomannan has a biodegradability of 60% or greater within 60 days in accordance with OECD 301 F.

12. The biodegradable cationic galactomannan of claim 11 , wherein the cationic galactomannan comprises cationic cassia (Senna tora / Senna obtusifolia).

13. The biodegradable cationic galactomannan of claims 11 or 12, wherein the DScationic ranges from 0.10 to lower than 0.18, preferably from 0.12 to lower than 0.18.

14. The biodegradable cationic galactomannan of claims 11 - 13, wherein the cationic galactomannan has a Mw of 900,000 g / mol or lower, preferably from about100,000 g / mol to 900,000 g / mol, more preferably about 150,000 g / mol to 750,000 g / mol.

15. The biodegradable cationic galactomannan of any of the preceding claims, wherein the cationic galactomannan is cationized by at least one cationizing agent selected from 2,3-epoxypropyltrimethylammonium chloride, 3-chloro-2- hydroxypropyltrimethylammonium chloride, and mixtures thereof.

16. The biodegradable cationic galactomannan of any 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; phosphinium groups; and combinations thereof.

17. The biodegradable cationic galactomannan of any 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.

18. The biodegradable cationic galactomannan of any of the preceding claims, wherein the cationic galactomannan has a biodegradability of 60% or greater within 28 days in accordance with OECD 301 F.

19. A composition comprising the biodegradable cationic galactomannan of any of the preceding claims.

20. The composition of claim 19, wherein the composition further comprises at least one surfactant, emulsifier, emollient, moisturizer, hair conditioning agent, hair fixative, film-former, skin protectant, binder, chelating agent, disinfectant, insecticide, fungicide, deodorant, pest repellant, odoriferous material, antimicrobial agent, antifungal agent, antibiotic, antidandruff agent, abrasive, adhesive,absorbent, colorant, deodorant, antiperspirant agent, humectant, oil (such as a mineral oil, a vegetable oil, an animal oil, a synthetic oil, a silicone oil and mixtures thereof), opacifying and pearlescing agent, antioxidant, preservative, propellant, spreading agent, exfoliant, keratolytic agent, blood coagulant, vitamin, sunscreen agent, artificial tanning accelerator, ultraviolet light absorber, pH adjusting agent, botanical, hair colorant, dye, preservative, inorganic particles, buffers, preservatives, oxidizing agents, reducing agent, rheology modifier, skin bleaching agent, pigment, anti-inflammatory agent, thickening agent, topical anesthetic, fragrance, fragrance solubilizer, particulate, microabrasive, abrasive, and combinations thereof.

21. A method of making the biodegradable cationic galactomannan of any of the preceding claims, wherein the method comprises reacting a non-cationic galactomannan with at least one cationizing agent.

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