[go: up one dir, main page]

WO2025087799A1 - Compositions contenant des galactomannanes cationiques - Google Patents

Compositions contenant des galactomannanes cationiques Download PDF

Info

Publication number
WO2025087799A1
WO2025087799A1 PCT/EP2024/079457 EP2024079457W WO2025087799A1 WO 2025087799 A1 WO2025087799 A1 WO 2025087799A1 EP 2024079457 W EP2024079457 W EP 2024079457W WO 2025087799 A1 WO2025087799 A1 WO 2025087799A1
Authority
WO
WIPO (PCT)
Prior art keywords
cationic
mol
composition
dscationic
groups
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/EP2024/079457
Other languages
English (en)
Inventor
Valérie RIZZO
David James Wilson
Mickaël CREGUT
Marios HOPKINS-HATZOPOULOS
Vincent MIRALLES
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Specialty Operations France SAS
Original Assignee
Specialty Operations France SAS
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Specialty Operations France SAS filed Critical Specialty Operations France SAS
Publication of WO2025087799A1 publication Critical patent/WO2025087799A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
    • C08B37/0087—Glucomannans or galactomannans; Tara or tara gum, i.e. D-mannose and D-galactose units, e.g. from Cesalpinia spinosa; Tamarind gum, i.e. D-galactose, D-glucose and D-xylose units, e.g. from Tamarindus indica; Gum Arabic, i.e. L-arabinose, L-rhamnose, D-galactose and D-glucuronic acid units, e.g. from Acacia Senegal or Acacia Seyal; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/737—Galactomannans, e.g. guar; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00

Definitions

  • compositions Having Cationic Galactomannans Compositions Having Cationic Galactomannans
  • the present invention generally relates to compositions having cationic galactomannans. More specifically, the present invention relates to compositions having cationic galactomannans, in which the cationic galactomannans have certain cationic degrees of substitution (DScationic) and average molecular weights (Mw).
  • DScationic cationic degrees of substitution
  • Mw average molecular weights
  • Galactomannans are a type of natural polymers formed from certain sugar residues. More specifically, galactomannans are polysaccharides having
  • 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.
  • 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.
  • native guar or guar gum typically has a mannose to galactose ratio of about 2:1 .
  • 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.
  • the galactomannans can be functionalized using a number of reactive agents.
  • one or more cationic reactive agents also known as cationizing agents, can be used.
  • 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.
  • cationic galactomannans can be used in a variety of applications, including in home and personal care applications, and the starting unmodified galactomannans are naturally derived, certain cationic galactomannans may not have the desired performance properties. For instance, with respect to personal care applications, especially hair care applications, the cationic galactomannans should provide sufficient benefits, such as sufficient conditioning. Further, in addition to potentially not having the desired performance properties, 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.
  • the present invention generally relates to compositions having cationic galactomannans.
  • an embodiment of the present invention relates to a composition comprising a cationic galactomannan, wherein the cationic galactomannan comprises a ratio of galactose to mannose units of about 1 :1 , the cationic galactomannan having:
  • another embodiment includes such cationic galactomannans having a DScationic of 0.20 or lower, preferably 0.17 or lower, more preferably lower than 0.17, and the cationic galactomannans have a biodegradability of 60% or greater within 60 days, preferably within 28 days, in accordance with OECD 301 F.
  • compositions comprising a cationic galactomannan, wherein the cationic galactomannan comprises 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:
  • Other embodiments in this respect include such cationic galactomannans having a DScationic of 0.20 or lower, preferably lower than 0.18, more preferably 0.17 or lower, and the cationic galactomannans have a biodegradability of 60% or greater within 60 days, preferably within 28 days, in accordance with OECD 301 F.
  • the present invention relates to a composition
  • a composition comprising a cationic galactomannan, wherein the cationic galactomannan comprises a ratio of galactose to mannose units of about 1 :5, the cationic galactomannan having:
  • other embodiments include such cationic galactomannans having a DScationic of 0.24 or lower, preferably 0.18 or lower, more preferably lower than 0.18, and the cationic galactomannans have a biodegradability of 60% or greater within 60 days, preferably within 28 days, in accordance with OECD 301 F.
  • the cationic galactomannans comprises 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.
  • 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
  • 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.
  • compositions of the present invention are personal care compositions, preferably hair care compositions.
  • any particular upper concentration, weight ratio or amount can be associated with any particular lower concentration, weight ratio or amount, respectively.
  • 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.
  • galactomannans having a mannose to galactose ratio of about 1 :1 to about 5:1 can be used.
  • 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.
  • 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.
  • galactomannans of the present invention can include those having repeating residues (/.e., units) as shown below in formula (I): 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.
  • Mw overall molecular weight
  • 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.
  • 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.
  • 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.
  • p can range from about 10 to about 35,000, including from about 100 to about 30,000.
  • 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.
  • 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.
  • 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.
  • various cationizing agents can be used.
  • the cationic galactomannans can be formed from reacting at least one galactomannan in accordance with the invention with at least one cationizing agent.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • the cationic substituent group is linked to the reactive functional group of the cationizing agent by an alkylene or oxyalkylene linking group.
  • the cationic groups or moieties can be of formula (II):
  • R 2 , R 3 , and R 4 are each independently organic groups or H in which at least one of R 2 , R 3 , and R 4 is H for the amine salt groups; for quaternary ammonium groups R 2 , R 3 , and R 4 are each independently organic groups, or any two of R 2 , R 3 , and R 4 may be fused to form with the nitrogen atom to which they are attached a heterocyclic group, and X’ is an anion.
  • 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.
  • 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
  • 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.
  • cationic galactomannans of the present invention can include those having repeating residues (/.e., units) as shown below in formula (III): wherein:
  • R 1 can have formula:
  • R 10 can be selected from -OH, an alkoxy quaternary ammonium group, or combinations thereof, preferably R 10 can be selected from -OH, -OR 1 , or combinations thereof, with the proviso that at least one R 10 is an alkoxy quaternary ammonium group, preferably -OR 1 ; 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.
  • 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.
  • 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.
  • the cationic galactomannans of the present invention can include those having repeating residues (i.e., units) as shown below in formula (V):
  • R 1 can have formula:
  • R 10 can be selected from -OH, an alkoxy quaternary ammonium group, or combinations thereof, preferably R 10 can be selected from -OH, -OR 1 , 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.
  • 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.
  • 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.
  • p can range from about 10 to about 35,000, including from about 100 to about 30,000.
  • 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.
  • the cationic galactomannans have a degree of substitution with respect to the cationic groups that are attached to the galactomannan (DScationic).
  • DScationic means the average number of the cationic groups or moieties attached per monomeric unit (/.e., each sugar unit) of the galactomannan.
  • 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.
  • the lower end of the range is greater than zero (>0).
  • the lower end of the range can be 0.000001 , 0.00001 , 0.0001 , 0.001 , 0.01 , or 0.10.
  • the cationic galactomannans of the present invention can generally have a DScationic of up to about 0.30.
  • cationic galactomannans having certain cationic degrees of substitution have improved conditioning properties.
  • cationic galactomannans having lower average molecular weights can potentially have higher cationic degrees of substitution while still having improved conditioning properties
  • cationic galactomannans having higher molecular weights usually have lower cationic degrees of substitution in order to have sufficient conditioning properties.
  • cationic galactomannans having lower average molecular weights can potentially have higher cationic degrees of substitution while having sufficient biodegradability, and cationic galactomannans having higher molecular weights can have lower cationic degrees of substitution while also having sufficient biodegradability. That is, in certain embodiments of the present invention, the cationic galactomannans can have sufficient - if not superior - conditioning properties, and in certain embodiments, the cationic galactomannans can have a combination of sufficient - if not superior - conditioning properties in combination with sufficient biodegradability.
  • the type of galactomannan - that is, the ratio of galactose to mannose units - may also affect the conditioning properties, as well as the biodegradability, along with the DScationic and average molecular weight (Mw).
  • the cationic galactomannan can generally have a DScationic of 0.20 or lower, 0.17 or lower, preferably 0.17 or lower.
  • the cationic galactomannan in certain embodiments in which the cationic galactomannan has a ratio of galactose to mannose units of about 1 :1 , can generally have a DScationic of less than 0.17, including a DScationic of 0.16 or lower, including a DScationic of 0.15 or lower. 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.
  • 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.
  • 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.
  • cationic galactomannans having a ratio of galactose to mannose units of about 1 :1 can also 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 0.20, preferably 0.12 to 0.20, more preferably 0.14 to 0.20, including from 0.10 to 0.17, 0.12 to 0.17, and 0.14 to 0.17 .
  • 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.
  • the cationic galactomannans when the cationic galactomannans have a ratio of galactose to mannose units of about 1 :1 , the cationic galactomannans can have a DScationic of lower than 0.17, preferably 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.
  • 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 0.22 or lower, preferably 0.20 or lower, more preferably 0.18 or lower, including lower than 0.18, as well as 0.17 or lower, and even more preferably 0.16 or lower.
  • 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.
  • the cationic galactomannan 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 0.20 or lower, preferably 0.18 or lower, including lower than 0.18, and more preferably 0.17 or lower.
  • the DScationic can range from 0.001 to 0.22, from 0.01 to 0.22, and from 0.10 to 0.22, as well as from 0.001 to 0.20, from 0.01 to 0.20, and from 0.10 to 0.20, and furthermore, from 0.001 to 0.19, from 0.01 to 0.19, and from 0.10 to 0.19, also including from 0.001 to 0.18, from 0.01 to 0.18, and from 0.10 to 0.18.
  • 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
  • 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.
  • 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 0.17, including 0.05 to 0.16, preferably 0.08 to 0.17, including 0.08 to 0.16, more preferably 0.10 to 0.17, including 0.10 to 0.16.
  • the cationic galactomannans 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, including 0.17 or lower, 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.
  • the cationic galactomannans when the cationic galactomannans have a ratio of galactose to mannose units of about 1 :3, the cationic galactomannans can have a DScationic of 0.20 or lower, preferably lower than 0.18, including 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.
  • the cationic galactomannan 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 0.24 or lower, preferably 0.22 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 0.21 or lower, preferably 0.20 or lower.
  • 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 0.20 or lower, including lower than 0.20, preferably 0.18 or lower, including lower than 0.18, more preferably 0.16 or lower, including lower than 0.16.
  • the DScationic can range from 0.001 to 0.24, from 0.01 to 0.24, and from 0.10 to 0.24, as well as from 0.001 to 0.22, from 0.01 to 0.22, and from 0.10 to 0.22, and furthermore, from 0.001 to 0.21 , from 0.01 to 0.21 , and from 0.10 to 0.21 , also including from 0.001 to 0.20, from 0.01 to 0.20, and from 0.10 to 0.20.
  • the DScationic can range from 0.001 to 0.18, including 0.001 to lower than 0.18, from 0.01 to 0.18, including 0.01 to lower than 0.18, and from 0.10 to 0.18, including 0.10 to lower than 0.18, and furthermore, from 0.001 to 0.16, from 0.01 to 0.16, and from 0.10 to 0.16.
  • 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.
  • 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 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 0.24, preferably from 0.14 to 0.22, more preferably from 0.14 to 0.20.
  • the cationic galactomannans when the cationic galactomannans have a ratio of galactose to mannose units of about 1 :5, the cationic galactomannans can have a DScationic of 0.24 or lower, preferably 0.18 or lower, more preferably 0.16 or lower. In other 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.
  • the cationic degree of substitution of the cationic galactomannans of the present invention may be determined before or after an extraction step.
  • 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.
  • 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.
  • 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 by 1 H-NMR (solvent : D2O). Once the 1 H 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:
  • 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 the 1 H-NMR spectra at lower field than the peak of interest, which is centered at about 3-3.5 ppm.
  • 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.
  • acidified methanol 50:1 , MeOH/ H Ciconcentrated 37%, v/v.
  • 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
  • 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.
  • 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 before 1 H-NMR analysis.
  • cationization of the galactomannan can also be expressed in terms of charge density.
  • 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.
  • 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.
  • the cationic charge density may be calculated from the cationic degree of substitution using the following equation:
  • 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.
  • the cationic galactomannans of the present invention 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.
  • 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.
  • Mw average molecular weight
  • 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.
  • the cationic galactomannan 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.
  • Mw average molecular weight
  • the cationic galactomannan 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, including 2,000,000 g/mol or lower. 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.
  • Mw average molecular weight
  • the cationic galactomannan 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, 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.
  • Mw average molecule weight
  • the cationic galactomannan 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.
  • Mw average molecular weight
  • the cationic galactomannan 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.
  • Mw average molecular weight
  • 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.
  • the cationic galactomannans of the present invention surprisingly and unexpectedly have sufficient - if not superior - conditioning properties, especially in home and personal care compositions, and preferably in hair care compositions.
  • the compositions of the present invention comprising the cationic galactomannans can have conditioning properties that are at least about 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, or better than compositions that do not have the present cationic galactomannans.
  • composition of the present invention comprising the cationic galactomannans can have conditioning properties that are at least about 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, or better compared to compositions that do not have the claimed cationic galactomannans alone or in combination with other component(s) or additive(s).
  • compositions of the present invention comprising the cationic galactomannans in combination with at least one other component or additive, as discussed further below (such as at least one surfactant, emulsifier, emollient, moisturizer, etc.) have conditioning properties, including with respect to hair conditioning properties, that are at least about 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, or better.
  • at least one surfactant such as at least one surfactant, emulsifier, emollient, moisturizer, etc.
  • conditioning properties including with respect to hair conditioning properties, that are at least about 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, or better.
  • compositions preferably home and personal care compositions, and more preferably hair care compositions
  • a cationic galactomannan having a ratio of galactose to mannose units of about 1 :1 , a DScationic of 0.20 or lower, preferably 0.17 or lower, more preferably lower than 0.17, and an average molecular weight (Mw) lower than 3,500,000 g/mol
  • the compositions can have conditioning properties that are at least 30%, preferably at least 40%, more preferably at least 50% better.
  • the compositions preferably home and personal care compositions, and more preferably hair care compositions, have a cationic galactomannan having a ratio of galactose to mannose units of about 1 : 1 , a DScationic of 0.20 or lower, preferably 0.17 or lower, more preferably lower than 0.17, and an average molecular weight (Mw) lower than 3,500,000 g/mol, the compositions can have conditioning properties that are at least 55% better, preferably at least 60% better.
  • compositions preferably home and personal care compositions, and more preferably hair care compositions
  • a 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, a DScationic of 0.20 or lower, preferably lower than 0.18, more preferably 0.17 or lower, and an average molecular weight (Mw) lower than 2,500,000 g/mol
  • the compositions can have conditioning properties that are at least 30%, preferably at least 40%, more preferably at least 50% better.
  • the compositions preferably home and personal care compositions, and more preferably hair care compositions, have a 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, a DScationic of 0.20 or lower, preferably lower than 0.18, more preferably 0.17 or lower, and an average molecular weight (Mw) lower than 2,500,000 g/mol, the compositions can have conditioning properties that are at least 55% better, preferably at least 60% better.
  • compositions preferably home and personal care compositions, and more preferably hair care compositions
  • a cationic galactomannan having a ratio of galactose to mannose units of about 1 :5, a DScationic of 0.24 or lower, preferably 0.18 or lower, more preferably lower than 0.18, and an average molecular weight (Mw) lower than 1 ,000,000 g/mol
  • the compositions can have conditioning properties that are at least 30%, preferably at least 40%, more preferably at least 50% better.
  • the compositions preferably home and personal care compositions, and more preferably hair care compositions, have a cationic galactomannan having a ratio of galactose to mannose units of about 1 :5, a DScationic of 0.24 or lower, preferably 0.18 or lower, more preferably lower than 0.18, and an average molecular weight (Mw) lower than 1 ,000,000 g/mol, the compositions can have conditioning properties that are at least 50% better, preferably at least 60% better.
  • 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.
  • the cationic galactomannans of the present invention are considered biodegradable under OECD 301 , and in particular are considered biodegradable under OECD 301 F.
  • OECD 301 F provides testing guidelines for determining whether a chemical substance is considered biodegradable, including readily biodegradable.
  • 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.
  • 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.
  • the cationic galactomannans of the present invention are not only biodegradable, but also provide conditioning properties, especially for home and personal care compositions, and preferably hair care compositions.
  • the cationic galactomannans can be made in a number of ways.
  • 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.
  • the galactomannans can be extracted from the endosperm of the seeds.
  • the galactomannans can be cationically functionalized by reacting the galactomannans with at least one cationizing agents.
  • 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.
  • the cationic galactomannan of the present invention can be made by reacting a chemically unmodified galactomannan with at least one cationizing agent.
  • the galactomannans can be in their respective native forms (/.e., gum forms).
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • the cationic galactomannans can undergo at least one chemical posttreatment step.
  • 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.
  • 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.
  • the cationic galactomannans can be chemically post-treated with borates, washed with water, or both.
  • the cationic galactomannans can be chemically post-treated with an alkali treatment step, washed with water, or both.
  • alkali metal hydroxides such as sodium hydroxide, ammonium hydroxide, and combinations thereof can be used.
  • 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.
  • the cationic galactomannan 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.
  • the cationic galactomannans of the present invention can be used in a variety of compositions and applications, and in preferred embodiments are biodegradable in addition to providing conditioning properties.
  • the cationic galactomannans in addition to being a conditioning agent, can be used as a suspending agent, thickener or rheology modifier, film forming agent, or combinations thereof.
  • the cationic galactomannans can be used in home and personal care compositions, such as hair care compositions, as well as in cleaning and disinfectant compositions.
  • the 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, make-up, lotions, skin creams, skin conditioners, balms, hair gels, sunscreen compositions, and similar compositions.
  • the 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.
  • the composition may contain various other convention components and additives known in the respective art.
  • the compositions having the 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 tannin
  • compositions of the present invention can have, in addition to the cationic galactomannan, surfactants selected from anionic surfactants, nonionic surfactants, zwitterionic surfactants, amphoteric surfactants, cationic surfactants, and combinations thereof.
  • the compositions of the present invention can have, in addition to the cationic galactomannan, anionic surfactants, amphoteric surfactants, or combinations thereof.
  • the surfactants can be sulfated or sulfate- free.
  • Non-limiting examples of sulfated surfactants include, but are not limited to sodium lauryl sulfate (SLS), sodium laureth sulfate (SLES), ammonium lauryl sulfate, ammonium laureth sulfate, potassium lauryl sulfate, sodium pareth sulfate, and combinations thereof.
  • SLS sodium lauryl sulfate
  • SLES sodium laureth sulfate
  • ammonium lauryl sulfate ammonium laureth sulfate
  • potassium lauryl sulfate potassium lauryl sulfate
  • sodium pareth sulfate and combinations thereof.
  • Non-limiting examples of sulfate-free surfactants include, but are not limited to sodium cocoyl isethionates (SCI), lauramidopropyl betaines (LAPB), alpha olefin sulfonates (AOS), lauryl hydroxysultaines (LHS), sodium methyl cocoyl taurates (SMCT), sodium cocoyl sarcosinates, sodium lauroyl sarcosinates, lauroamphoacetates, cocam idopropyl betaines (CAPB), and combinations thereof.
  • SCI sodium cocoyl isethionates
  • LAPB lauramidopropyl betaines
  • AOS alpha olefin sulfonates
  • LHS lauryl hydroxysultaines
  • SMCT sodium methyl cocoyl taurates
  • sodium cocoyl sarcosinates sodium lauroyl sarcosinates
  • lauroamphoacetates
  • composition percentages are based on totals equal to 100% by weight, unless otherwise specified.
  • 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.
  • 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.
  • the hair tresses were hand combed to remove major tangles, and then combed ten (10) times at 300 mm/min using a MTT 175 Miniature Tensile Tester (Dia-Stron Ltd) equipped with an ACE hard rubber fine tooth comb.
  • a MTT 175 Miniature Tensile Tester Dia-Stron Ltd
  • the hair was immersed in water to keep it wet between each combing cycle.
  • the excess water was removed by hand in 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.
  • each 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. Excess water from the tress was removed by hand. This second step is repeated once more.
  • the shampooed hair tresses were then hand combed to remove major tangles and then combed for ten (10) times at 300 mm/min using the 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.
  • control tresses were only wetted with water in accordance with above and tested for combining work also in accordance with the above. Using the total combing work of each hair tress before and after shampoo application, as described in the steps above, the percent combing improvement was calculated.
  • 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.
  • 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. 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 (i.e., passed). Additionally, the cationic fenugreek demonstrated a significant combing improvement.
  • 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.
  • 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.
  • the cationic degree of substitution 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 (i.e., passed).
  • Example 3 Cationic Fenugreek
  • 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.
  • 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.
  • 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.
  • the cationic degree of substitution 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). Additionally, the cationic fenugreek demonstrated a significant combing improvement.
  • 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.
  • 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.
  • the cationic degree of substitution was 0.17 and the average molecular weight (Mw) was 1 ,696,000 g/mol. While the cationic fenugreek was tested for biodegradability and it demonstrated that it was not readily biodegradable within 60 days (/.e., failed), nevertheless, the cationic fenugreek demonstrated a significant combing improvement.
  • 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.
  • a reaction mixture obtained as described in the paragraph above was dispersed under stirring with 158.5 g of isopropanol (99%) and 36.2 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 357 g of isopropanol (99%) and 146 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 was 0.20 and the average molecular weight (Mw) was 1 ,819,000 g/mol.
  • the cationic fenugreek was not tested for biodegradability; however, the cationic fenugreek demonstrated a significant combing improvement.
  • cationic fenugreeks having a cationic degree of substitution of 0.20 or lower, including a cationic degree of substitution of 0.17 or lower, such as a cationic degree of substitution lower than 0.17 demonstrate superior conditioning performance.
  • cationic fenugreeks having a cationic degree of substitution lower than 0.17, such as for example a cationic degree of substitution of 0.16 or lower, including 0.15 or lower demonstrate a superior combination of both conditioning (/.e., combing improvement) and biodegradability.
  • 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.
  • a reaction mixture obtained as described in the paragraph above was dispersed under stirring with 112.6 g of isopropanol (99%) and 22.9 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 249 g of isopropanol (99%) and 101 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 was 0.13 and the average molecular weight (Mw) was 1 ,378,000 g/mol.
  • the cationic tara demonstrated a significant combing improvement.
  • 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.
  • 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.
  • the cationic degree of substitution 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 60 days (/.e., passed). Additionally, the cationic tara demonstrated a significant combing improvement.
  • 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.
  • 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 1.1 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 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.
  • 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.
  • 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.
  • the cationic degree of substitution 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). The cationic tara also demonstrated significant combing improvement.
  • 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.
  • a reaction mixture obtained as described in the paragraph above was dispersed under stirring with 113.0 g of isopropanol (99%) and 24.0 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.
  • the cationic degree of substitution was 0.18 and the average molecular weight (Mw) was 1 ,387,000 g/mol.
  • the cationic tara demonstrated a significant combing improvement.
  • 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.
  • 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.
  • the cationic degree of substitution 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); however, the cationic tara demonstrated a significant combing improvement.
  • 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.
  • 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.
  • the cationic degree of substitution 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).
  • the cationic tara demonstrated a significant combing improvement.
  • 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.
  • 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.
  • the cationic degree of substitution 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). Further, the cationic tara demonstrated reduced combining performance versus cationic taras having DScationic ranges at 0.20 or below.
  • 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.
  • 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.
  • 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 (/.e., failed).
  • cationic taras having a cationic degree of substitution of 0.20 or lower demonstrate superior conditioning performance.
  • cationic taras having a cationic degree of substitution of lower than 0.18, including 0.17 or lower demonstrate a combination of superior conditioning performance and biodegradability versus cationic taras having a cationic degree of substitution of 0.18 or higher.
  • 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.
  • 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.
  • the cationic degree of substitution 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 (/.e., passed), while also demonstrating improved combing performance.
  • 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.
  • 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.
  • the cationic degree of substitution was 0.18 and the average molecular weight (Mw) was 743,000 g/mol. While the cationic cassia was tested for biodegradability and it demonstrated that it was not readily biodegradable within 60 days (/.e., failed), nevertheless, the cationic cassia demonstrated improved combing performance.
  • 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.
  • 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.
  • the cationic degree of substitution 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 (/.e., failed), nevertheless, the cationic cassia demonstrated improved combing performance.
  • cationic cassias having a cationic degree of substitution of 0.24 or lower demonstrate superior conditioning performance, while cationic cassias having a cationic degree of substitution lower than 0.18 demonstrate a superior combination of both conditioning and biodegradability.

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Birds (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Emergency Medicine (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Materials Engineering (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)

Abstract

La présente invention concerne de manière générale des compositions contenant des galactomannanes cationiques.
PCT/EP2024/079457 2023-10-23 2024-10-18 Compositions contenant des galactomannanes cationiques Pending WO2025087799A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202363592315P 2023-10-23 2023-10-23
US63/592,315 2023-10-23

Publications (1)

Publication Number Publication Date
WO2025087799A1 true WO2025087799A1 (fr) 2025-05-01

Family

ID=93212080

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2024/079457 Pending WO2025087799A1 (fr) 2023-10-23 2024-10-18 Compositions contenant des galactomannanes cationiques

Country Status (1)

Country Link
WO (1) WO2025087799A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4753659A (en) * 1983-12-29 1988-06-28 Diamalt Aktiengesellschaft Derivatives of cassia tora polysaccarides and their use
JP2006241330A (ja) * 2005-03-03 2006-09-14 Toho Chem Ind Co Ltd カチオン変性精製タラガム及び該物質を含む化粧料組成物
US9782609B2 (en) * 2013-10-07 2017-10-10 Hercules Llc Dihydroxyalkyl substituted polygalactomannan, and methods for producing and using the same
US10993900B2 (en) * 2013-09-04 2021-05-04 Lamberti Spa Cosmetic and household care compositions

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4753659A (en) * 1983-12-29 1988-06-28 Diamalt Aktiengesellschaft Derivatives of cassia tora polysaccarides and their use
JP2006241330A (ja) * 2005-03-03 2006-09-14 Toho Chem Ind Co Ltd カチオン変性精製タラガム及び該物質を含む化粧料組成物
US10993900B2 (en) * 2013-09-04 2021-05-04 Lamberti Spa Cosmetic and household care compositions
US9782609B2 (en) * 2013-10-07 2017-10-10 Hercules Llc Dihydroxyalkyl substituted polygalactomannan, and methods for producing and using the same

Similar Documents

Publication Publication Date Title
KR101131674B1 (ko) 셀룰로스 에테르
JP6262131B2 (ja) グアーヒドロキシプロピルトリメチルアンモニウムクロリドおよびヘアトリートメント組成物でのその使用
EP2449079B1 (fr) Polymères cationiques synthétiques ayant une solubilité et performance améliorées dans des systèmes tensioactifs et leur utilisation pour l'hygiène personnelle et dans des applications domestiques
EP2088994B2 (fr) Guar cationique rendue dispersible par reticulation avec du glyoxal
EP3488899B1 (fr) Composition de soins des cheveux
EP2109441B1 (fr) Copolymères séquencés de polysiloxane
MX2011009922A (es) Polimeros aminados y sus uso en composiciones llevadas por agua.
WO2025087799A1 (fr) Compositions contenant des galactomannanes cationiques
WO2025087800A1 (fr) Compositions présentant des galactomannanes cationiques
JP2025121916A (ja) 毛髪修復組成物
WO2025087798A1 (fr) Galactomannanes cationiques biodégradables
WO2025087797A1 (fr) Galactomannanes cationiques biodégradables
WO2012130997A1 (fr) Utilisation de galactomannanes modifiés pour protéger une couleur de cheveux teintés contre la décoloration
WO2025149373A1 (fr) Galactomannanes cationiques issus de guar et leur procédé de production
WO2015176671A1 (fr) Arabinoxylanes cationiques, leurs produits modifiés de façon hydrophobe et leur procédé de préparation et application
WO2017109067A1 (fr) Procédé de traitement de fibres de kératine, comprenant l'application d'une composition contenant de l'urée ou un dérivé d'urée, un polyol et une silicone aminée

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 24793800

Country of ref document: EP

Kind code of ref document: A1