[go: up one dir, main page]

WO2025149373A1 - Galactomannanes cationiques issus de guar et leur procédé de production - Google Patents

Galactomannanes cationiques issus de guar et leur procédé de production

Info

Publication number
WO2025149373A1
WO2025149373A1 PCT/EP2024/088297 EP2024088297W WO2025149373A1 WO 2025149373 A1 WO2025149373 A1 WO 2025149373A1 EP 2024088297 W EP2024088297 W EP 2024088297W WO 2025149373 A1 WO2025149373 A1 WO 2025149373A1
Authority
WO
WIPO (PCT)
Prior art keywords
galactomannan
cationic
groups
mannose
guar
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/EP2024/088297
Other languages
English (en)
Inventor
David James Wilson
Valérie RIZZO
Marios HOPKINS-HATZOPOULOS
Minrui XU
Galder Cristobal
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 WO2025149373A1 publication Critical patent/WO2025149373A1/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
    • 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
    • C08B37/0096—Guar, guar gum, guar flour, guaran, i.e. (beta-1,4) linked D-mannose units in the main chain branched with D-galactose units in (alpha-1,6), e.g. from Cyamopsis Tetragonolobus; 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

  • the present invention concerns cationic galactomannans obtained from guar gum, a process of production of such cationic galactomannans and performance properties, such as conditioner, for home and personal care applications.
  • Galactomannans are polysaccharides consisting of a mannose backbone with galactose side groups which can be obtained from a number of Leguminosae. Cationic galactomannans are commonly used in personal care products like hair or skin. Mention can be made to US 2008/0112907, US 2003/0211952 or WO 2013/011122.
  • Cationically modified galactomannans derived from tara gum have improved conditioning properties in home and personal care products, notably products rinsed from hair and body, if compared to cationically modified galactomannans derived from guar gum, according to JP2006241330.
  • galactomannans derived from locust bean and cassia consist in a polymer having main chain of P-l,4-linked mannose units with side chains of a-1,6- linked galactose approximately every forth mannose unit and every fifth mannose unit, respectively.
  • galactose content in galactomannans can be modified to a certain extent by using galactosidase enzymes able to remove inherently linked galactose units from the backbone, as is described in the US patent 5,234,825.
  • the residual galactose may be particularly relevant, notably when a cationization is implemented, as any residual galactose may be also cationized, impacting the final performance of cationic galactomannan.
  • the present invention is thus, based on a cationic galactomannan comprising a mannose/galactose molar ratio within the range of 2.5 : 1 to 5 : 1 , wherein the cationic galactomannan is derived from guar gum.
  • the present invention also aims to provide a process for preparing said cationic galactomannans with a precise control of the mannose/galactose ratio.
  • the cationic galactomannans with a controlled mannose/galactose ratio have not only excellent performance in personal care compositions but also high biodegradability.
  • weight percent As used herein, “weight percent,” “wt%,” “percent by weight,” “% by weight,” and variations thereof refer to the concentration of a substance as the weight of that substance divided by the total weight of the composition and multiplied by 100.
  • the ratio mannose/galactose can be calculated as follows:
  • the (DScat) or (D Scationic ) relates to the cationic degree of substitution measured before the acidic methanol extraction.
  • the cationic galactomannan has a cationic degree of substitution (DS ca t)extraction for cationic substituent groups ranging from 0.01 to 1.0.
  • the cationicity of the cationic galactomannan may also be expressed in terms of charge density.
  • the cationic degree of substitution may be converted to a charge density through several methods.
  • the cationic galactomannan has a charge density after the acidic methanol extraction from about 0.06 to about 3.2 meq/g, for example from about 0.06 to about 1.8 meq/g, and for example from 0.06 to 1.2 meq/g.
  • the average molecular weight of the cationic galactomannan herein is lower than about 2,500 kDa more preferably lower than 1,900 kDa.
  • the average molecular weight of said cationic galactomannan is comprised from 600 kDa to about 1,900 kDa.
  • the "average molecular weight" of the cationic galactomannan means the weight average molecular mass of said galactomannan.
  • the average molecular weight of the cationic galactomannan may be measured by SEC- MALS (Size Exclusion Chromatography with Multi-Angle Light-Scattering detection). A value of 0.140 for dn/dc is used for the molecular weight measurements.
  • a Wyatt MALS detector is calibrated using a 22.5 kDa polyethylene glycol standard. All calculations of the molecular weight distributions are performed using Wyatt's ASTRA software.
  • the samples are prepared as 0.05% solutions in the mobile phase (100 mM NaNCE, 200 ppm NaNs, 20 ppm pDADMAC) and filtered through 0.45 pm PVDF filters before analysis.
  • 100 pL of the filtered solution are injected and then go through a pre-column plus 3 columns OH pak SB-806 M at 35°C.
  • the samples are prepared as 0.05% solutions in the mobile phase (100 mMNaNCh, 200 ppm NaNs) and filtered through 0.45 pm PVDF filters before analysis.
  • 100 pL of the filtered solution are injected and then go through a pre-column plus 3 columns OH pak SB-806 M at 35°C.
  • the galactomannans can be functionalized by chemical modification using a variety of cationic reactive agents, also known as cationizing agents.
  • Cationizing agents of the present invention are defined as compounds which, by reaction with the hydroxyl groups of the galactomannan can lead to galactomannan comprising at least one cationic group according to the invention.
  • 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 epoxides such as 2,3-epoxypropyltrimethylammonium chloride, 2,3- epoxypropyltrimethylammonium bromide, 2,3 -epoxypropyltrimethylammonium iodide, and mixtures thereof;
  • chlorohydrin-functional cationic nitrogen compounds such as 3-halogeno-2- hydroxypropyl trimethylammonium chloride, for example 3 -chi oro-2 - hydroxypropyl trimethylammonium chloride, and mixtures thereof;
  • cationic ethylenically unsaturated monomers or their precursors such as trimethylammoniumpropyl methacrylamide chloride salt, trimethylammoniumpropyl methacrylamide methylsulfate salt, diallyl dimethyl ammonium chloride, vinyl benzyl trimethylammonium chloride, dimethylaminopropyl methacrylamide (tertiary amine) precursors of cationic monomers, such as A-vinyl formamide, A-vinyl acetamide (whose units can be hydrolyzed after polymerization or grafted onto vinyl amine units), and mixtures thereof.
  • trimethylammoniumpropyl methacrylamide chloride salt trimethylammoniumpropyl methacrylamide methylsulfate salt
  • diallyl dimethyl ammonium chloride vinyl benzyl trimethylammonium chloride
  • dimethylaminopropyl methacrylamide (tertiary amine) precursors of cationic monomers such as A-vinyl
  • the cationizing agents, which lead to cationic galactomannan of the invention can be selected from 2,3-epoxypropyltrimethylammonium chloride, 2,3- epoxypropyltrimethylammonium bromide, 2,3 -epoxypropyltrimethylammonium iodide, 3 -halogeno-2 -hydroxypropyl trimethylammonium chloride, including for example 3- chloro-2 -hydroxypropyl trimethylammonium chloride, and combinations thereof.
  • the cationic galactomannan of the invention is cationized by at least one cationizing agent selected from 2,3-epoxypropyltrimethylammonium chloride, 3 -chi oro-2 -hydroxypropyltrimethylammonium chloride, and mixtures thereof.
  • the cationic groups may be introduced into a modified galactomannan by reacting the modified galactomannan starting material with a derivatizing agent which comprises a reactive functional group and at least one cationic moiety (or a precursor of cationic moiety).
  • a group of suitable derivatizing reagents typically contain a reactive functional group, such as an epoxy group, a halide group, an ester group, an anhydride group or an ethylenically unsaturated group, and at least one cationic moiety or a precursor of such cationic moiety.
  • the cationic galactomannan of the invention comprises cationic groups selected from amino groups selected from primary, secondary, tertiary amino groups, and combinations thereof; quaternary ammonium groups; sulfonium groups; phosphonium groups; and combinations thereof.
  • the cationic group of the galactomannan of the invention is selected from trialkylammonium groups, such as trimethylammonium groups, triethylammonium groups, or tributylammonium groups; aryldialkylammonium groups, such as benzyldimethylammonium groups; ammonium groups wherein the nitrogen atom is a member of a ring structure, such as pyridinium groups and imidazoline groups; and combinations thereof.
  • 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.
  • the obtained swollen guar gum is contacted with an enzymatic solution comprising at least one enzyme and a buffer and submitted to enzymatic reaction.
  • the enzymatic solution is obtained using a mixture of at least one enzyme and a buffer in a molar concentration of between 0.01 to 0.05 M, preferably between 0.01 to 0.03 M, based on the total weight of the enzymatic solution.
  • Buffer solutions used in the sense of the invention may be selected in a non limited way by sodium acetate, potassium acetate solution, sodium citrate solution and potassium phthalate solution.
  • the swollen guar is added to the enzymatic solution in a weight ratio of guar over total weight of the mixture between 0.01 to 0.1, preferably between 0.01 to 0.03, based on the total weight of the mixture.
  • the enzymatic reaction is conducted at a temperature of 0 to 90°C, preferably of 30 to 80°C.
  • the enzymatic reaction is preferably carried out for a duration of at least 5 hours. According to the invention, the enzymatic reaction is carried out preferably for a duration of 5 to 30 hours, more preferably of 5 to 24 hours.
  • the enzymatic reacted guar is then washed using a mixture of alcohol: water to obtain the raw fragmented galactomannan.
  • the washing mixture comprises alcohol: water in a volume ratio from 1 : 1 to 10:5 (v/v) based on the total volume of the mixture.
  • the raw fragmented galactomannan is completely dried in an oven at 50°C under atmospheric pressure for 16 hours and ground using a cryogenic grinder into fine powder.
  • the inventors have found that the additional washing process allows the complete removal of galactose units cleaved and trapped into the raw fragmented galactomannan mixture.
  • the ground powder is then washed at least four times using a mixture of alcohol: water to obtain the modified galactomannan; wherein the modified galactomannan comprises mannose/galactose molar ratio within the range of 2.5 : 1 and 5: 1.
  • the cationic galactomannan of the invention can be used in home and personal applications, for example as conditioners, stabilizers, thickeners, emulsifiers, deposition aids, rheology modifiers and flocculants.
  • Home care composition shall include general household cleaning products for example, toilet bowl cleaners, laundry detergents, fabric softeners, dishwashing liquid, bathroom cleaner and surface cleaner. These compositions may also comprise aesthetic modifiers, film-formers, chelates, emulsifiers, moisturizers, emollients, surfactants (such as anionic, cationic, nonionic, amphoteric, zwitterionic, surfactants, or combinations thereof), propellants, stabilizers, preservatives, cleansing and suspending/gelling agents, and active ingredients.
  • aesthetic modifiers for example, toilet bowl cleaners, laundry detergents, fabric softeners, dishwashing liquid, bathroom cleaner and surface cleaner.
  • chelates emulsifiers
  • moisturizers emollients
  • surfactants such as anionic, cationic, nonionic, amphoteric, zwitterionic, surfactants, or combinations thereof
  • propellants such as anionic, cationic, nonionic, amphoteric, zwitterio
  • the average molecular weight of the modified galactomannan or the cationic galactomannan was measured by SEC-MALS (Size Exclusion Chromatography with Multi-Angle Light-Scattering detection) with 3 columns Shodex Pack OH pak LB-806 M column, as described above.
  • biodegradability of the cationic galactomannans were measured in accordance with OECD 302B (modified, as discussed above), which was modified with respect to the % of biodegradability of the sample tested (i.e., at least 60%) and the sensor used to determine the biodegradation. Biodegradability was assessed based on 28 days, as well as based on 60 days. An OxiTop®-IDS sensor available from Xylem Analytics was used to determine the biodegradation. The inoculum was not pre-adapted.
  • Comparative Example 1 Synthesis of modified galactomannan In step b.
  • 150 g of ultrapure water 0.50 mL of sodium acetate buffer solution (3M, pH 5.2 ⁇ 0.1 at 25°C) and 29 pL of enzyme a-galactosidase (2.9 U of enzyme/g of guar).
  • 5 g of guar gum are added to the enzymatic solution.
  • the obtained paste is mixed with a spatula for 5 minutes every 2 hours for the first 8 hours.
  • the reaction medium is heated at 40°C for 24 hours. After 24 hours, the reaction medium is heated at 80°C for 30 minutes to denature the enzyme.
  • 200 mL of isopropanol are added into the flask to reduce the viscosity and obtain the reaction medium with enzymatic reacted guar.
  • step c The reaction medium is filtered under vacuum and washed four times with a solution composed of isopropanol and water (200 mL). A white gel is obtained and it is dried in an oven at 50°C under atmospheric pressure for 16 hours to obtain the raw fragmented galactomannan solid. The raw fragmented galactomannan solid is ground into a fine powder resulting in a comparative modified galactomannan.
  • the resulting comparative modified galactomannan CMG1 showed a mannose/galactose molar ratio equal to 1.88: 1.
  • step b In a 500 mL round bottom flask with a magnetic stirrer and a condenser are introduced 145 g of ultrapure water, 0.50 mL of sodium acetate buffer solution (3M, pH 5.2 ⁇ 0.1 at 25°C) and 29 pL of enzyme a-galactosidase (2.9 U of enzyme/g of guar). The swollen guar is added to the enzymatic solution portion by portion under stirring (200 rpm). After addition, the reaction medium is heated at 40°C for 24 hours. After 24 hours, the reaction medium is heated at 80°C for 30 minutes to denature the enzyme.
  • sodium acetate buffer solution 3M, pH 5.2 ⁇ 0.1 at 25°C
  • enzyme a-galactosidase 2.9 U of enzyme/g of guar
  • step c After cooling to room temperature, 200 mL of isopropanol are added into the flask to reduce the viscosity and obtain the reaction medium with enzymatic reacted guar.
  • step c The reaction medium is filtered under vacuum and washed four times with a solution composed of isopropanol and water (200 mL). A white gel is obtained and it is dried in an oven at 50°C under atmospheric pressure for 16 hours to obtain the raw fragmented galactomannan solid.
  • the raw fragmented galactomannan solid is ground into a fine powder resulting in a comparative modified galactomannan.
  • the resulting comparative modified galactomannan CMG2 showed a mannose/galactose molar ratio equal to 2.3 : 1
  • step c The reaction medium is filtered under vacuum and washed four times with a solution composed of isopropanol and water (200 mL). A white gel is obtained and it is dried in an oven at 50°C under atmospheric pressure for 16 hours to obtain the raw fragmented galactomannan solid.
  • the resulting comparative modified galactomannan CMG3 showed a mannose/galactose molar ratio equal to 1.95: 1.
  • step b In an 1 L round bottom flask with a magnetic stirrer and a condenser are introduced 435 g of ultrapure water, 1.50 mL of sodium acetate buffer solution (3M, pH 5.2 ⁇ 0.1 at 25°C) and 78 pL of the enzyme a-galactosidase (2.60 U of enzyme/g of guar). The swollen guar is added to the enzymatic solution portion by portion under stirring (200 rpm). After addition, the reaction medium is heated at 40°C for 24 hours. After 24 hours, the reaction medium is heated at 80°C for 30 minutes to denature the enzyme. After cooling to room temperature, 200 mL of isopropanol are added into the flask to reduce the viscosity and obtain the reaction medium with enzymatic reacted guar.
  • sodium acetate buffer solution 3M, pH 5.2 ⁇ 0.1 at 25°C
  • 78 pL of the enzyme a-galactosidase 2
  • step a In a mortar, 15 g of guar gum and 15 g of ultrapure water are introduced. The mixture is mixed with a pestle to obtain a swollen guar powder.
  • step c The reaction medium is filtered under vacuum and washed four times with a solution composed of isopropanol and water (200 mL). A white gel is obtained and it is dried in an oven at 50°C under atmospheric pressure for 16 hours to obtain the raw fragmented galactomannan solid.
  • step d The raw fragmented galactomannan solid is ground into a fine powder and further washed by four times with a solution composed of isopropanol and water (200 mL) to obtain modified galactomannan.
  • step a In a mortar, 15 g of guar gum and 15 g of ultrapure water. The mixture is mixed with a pestle to obtain a swollen guar powder.
  • step b In an 1 L round bottom flask with a magnetic stirrer and a condenser are introduced 435 g of ultrapure water, 1.50 mL of sodium acetate buffer solution (3M, pH 5.2 ⁇ 0.1 at 25°C) and 87 pL of enzyme a-galactosidase (2.90 U of enzyme/g of guar). The swollen guar is added to the enzymatic solution portion by portion under stirring (200 rpm). After addition, the reaction medium is heated at 40°C for 24 hours. After 24 hours, the reaction medium is heated at 80°C for 30 minutes to denature the enzyme. After cooling to room temperature, 200 mL of isopropanol are added into the flask to reduce the viscosity and obtain the reaction medium with enzymatic reacted guar.
  • sodium acetate buffer solution 3M, pH 5.2 ⁇ 0.1 at 25°C
  • enzyme a-galactosidase 2.90 U of enzyme/g of
  • step c The reaction medium is filtered under vacuum and washed four times with a solution composed of isopropanol and water (200 mL). A white gel is obtained and it is dried in an oven at 50 °C under atmospheric pressure for 16 hours to obtain the raw fragmented galactomannan solid.
  • step d The raw fragmented galactomannan is ground into a fine powder and further washed four times with a solution composed of isopropanol and water (200 mL) to obtain modified galactomannan.
  • step a In a mortar, 17 g of guar gum and 17 g of ultrapure water were introduced. The mixture is mixed with a pestle to obtain a swollen guar powder.
  • step b In an 1 L round bottom flask with a magnetic stirrer and a condenser are introduced 133 g of ultrapure water, 0.50 mL of sodium acetate buffer solution (3M, pH 5.2 ⁇ 0.1 at 25°C) and 99 pL of enzyme a-galactosidase (2.90 U of enzyme/g of guar). The swollen guar is added to the enzymatic solution portion by portion under stirring (200 rpm). After addition, the reaction medium is heated at 40°C for 24 hours. After 24 hours, the reaction medium is heated at 80°C for 30 minutes to denature the enzyme. After cooling to room temperature, 200 mL of isopropanol are added into the flask to reduce the viscosity and obtain the reaction medium with enzymatic reacted guar.
  • sodium acetate buffer solution 3M, pH 5.2 ⁇ 0.1 at 25°C
  • enzyme a-galactosidase 2.90 U of enzyme/g of
  • step c The reaction medium is filtered under vacuum and washed four times with a solution composed of isopropanol and water (200 mL). A white gel is obtained and it is dried in an oven at 50°C under atmospheric pressure for 16 hours to obtain the raw fragmented galactomannan solid.
  • step d The raw fragmented galactomannan is ground into a fine powder and further washed four times with a solution composed of isopropanol and water (200 mL) to obtain modified galactomannan.
  • the cationic degree of substitution (DS ca tionic) was 0.17 and the (DS ca t)extraction was 0.14.
  • the average molecular weight (Mw) was 1037 kDa.
  • the cationic galactomannan was evaluated according to the OECD 302B procedure. The biodegradation expressed was 64% after 28 days. The cationic galactomannan is considered as inherently ultimately biodegradable.
  • the hair tresses were then gently hand combed to remove major tangles and then combed ten times at 300 mm/min using a MTT 175 Miniature Tensile Tester (Dia- Stron Ltd) equipped with an ACE hard rubber fine tooth comb.
  • the hair was immersed in water and wrung through between the index and middle finger to keep it wet between each combing cycle.
  • the tresses were hung vertically and stored overnight in a climatic room at about 21°C ⁇ 5°C and about 50% relative humidity.
  • each of the aforementioned hair tress was rewetted under running water for 60 seconds and shampooed by applying 0.2 gram of shampoo per gram of hair along the hair length.
  • the tress was kneaded for 45 seconds and then it was rinsed under 30°C running water for 30 seconds and then wrung through between the index and middle finger. This second step is repeated once more.
  • the shampooed hair tresses whilst still being wet were then gently hand combed to remove major tangles and then combed for ten times at 300 mm/min using a MTT 175 Miniature Tensile Tester (Dia-Stron Ltd) equipped with an ACE hard rubber fine tooth comb. Between each combing cycle, the hair was rewetted with water to keep it wet. Combing force versus displacement curves were obtained in the process. Total combing works (corresponding to the integral of this signal) are extracted. From the 10 combing cycle data, the average wet combing work was calculated for each hair tress. For each formulation, a minimum of three hair tresses were assigned and used to determine the average total combing work for the formulation. The lower the total work is, the higher the wet conditioning efficiency of the formulation is. Using the total combing work of each hair tress before and after shampoo application, as described in the steps above, the percent combing improvement is calculated and reported in TABLE 2.
  • cationic galactomannan according to the invention could significantly reduce the combing force, comparable to commercially cationic guar.

Landscapes

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

Abstract

La présente invention concerne un galactomannane cationique issu de gomme de guar et ayant un rapport molaire mannose/galactose situé dans la plage de 2,5:1 et 5:1, un procédé pour le produire et ses performances et son utilisation dans des formulations de soins personnels et domestiques.
PCT/EP2024/088297 2024-01-12 2024-12-23 Galactomannanes cationiques issus de guar et leur procédé de production Pending WO2025149373A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP24315010 2024-01-12
EP24315010.9 2024-01-12

Publications (1)

Publication Number Publication Date
WO2025149373A1 true WO2025149373A1 (fr) 2025-07-17

Family

ID=89843726

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2024/088297 Pending WO2025149373A1 (fr) 2024-01-12 2024-12-23 Galactomannanes cationiques issus de guar et leur procédé de production

Country Status (1)

Country Link
WO (1) WO2025149373A1 (fr)

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5234825A (en) 1983-03-11 1993-08-10 Unilever Patent Holdings, B.V. Process of polysaccharides
US5473059A (en) 1993-03-10 1995-12-05 Rhone-Poulenc Inc. Modified hydrophobic cationic thickening compositions
US5532350A (en) 1994-02-15 1996-07-02 Rhone-Poulenc Inc. Crosslinked polysaccharides useful as absorbent materials
US5801116A (en) 1995-04-07 1998-09-01 Rhodia Inc. Process for producing polysaccharides and their use as absorbent materials
US20030211952A1 (en) 2002-05-06 2003-11-13 Paquita Erazo-Majewicz Cationic polymer composition and its use in conditioning applications
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
EP1739095A1 (fr) * 2004-01-30 2007-01-03 Toho Chemical Industry Co., Ltd. Polysaccharide galacto-mannane purifie modifie et composition cosmetique contenant la substance
US20080112907A1 (en) 2006-11-03 2008-05-15 Chan Anita N Dispersible cationic polygalactomannan polymers for use in personal care and household care applications
WO2012170171A1 (fr) * 2011-06-10 2012-12-13 Lubrizol Advanced Materials, Inc. Dérivés de cannelle
WO2013011122A1 (fr) 2011-07-21 2013-01-24 Rhodia Operations Chlorure de guar hydroxypropyltriméthylammonium et ses utilisations dans des compositions de traitement capillaire

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5234825A (en) 1983-03-11 1993-08-10 Unilever Patent Holdings, B.V. Process of polysaccharides
US5473059A (en) 1993-03-10 1995-12-05 Rhone-Poulenc Inc. Modified hydrophobic cationic thickening compositions
US5532350A (en) 1994-02-15 1996-07-02 Rhone-Poulenc Inc. Crosslinked polysaccharides useful as absorbent materials
US5801116A (en) 1995-04-07 1998-09-01 Rhodia Inc. Process for producing polysaccharides and their use as absorbent materials
US20030211952A1 (en) 2002-05-06 2003-11-13 Paquita Erazo-Majewicz Cationic polymer composition and its use in conditioning applications
EP1739095A1 (fr) * 2004-01-30 2007-01-03 Toho Chemical Industry Co., Ltd. Polysaccharide galacto-mannane purifie modifie et composition cosmetique contenant la substance
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
US20080112907A1 (en) 2006-11-03 2008-05-15 Chan Anita N Dispersible cationic polygalactomannan polymers for use in personal care and household care applications
WO2012170171A1 (fr) * 2011-06-10 2012-12-13 Lubrizol Advanced Materials, Inc. Dérivés de cannelle
WO2013011122A1 (fr) 2011-07-21 2013-01-24 Rhodia Operations Chlorure de guar hydroxypropyltriméthylammonium et ses utilisations dans des compositions de traitement capillaire

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PAI V B ET AL: "Gelation and rheology of xanthan/enzyme-modified guar blends", CARBOHYDRATE POLYMERS, APPLIED SCIENCE PUBLISHERS , LTD BARKING, GB, vol. 49, no. 2, 1 August 2002 (2002-08-01), pages 207 - 216, XP004349648, ISSN: 0144-8617, DOI: 10.1016/S0144-8617(01)00328-9 *

Similar Documents

Publication Publication Date Title
KR102108215B1 (ko) 구아 하이드록시프로필트리메틸암모늄 클로라이드 및 모발 처리용 조성물에서의 그 용도
RU2568133C2 (ru) Полисахаридный продукт с улучшенными характеристиками и прозрачностью в водных композициях на основе пав и способ его получения (варианты)
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
KR101131674B1 (ko) 셀룰로스 에테르
RU2528915C2 (ru) Моющие составы, включающие нецеллюлозные полисахариды со смешанными катионными заместителями
CN105517632B (zh) 美容和家用护理组合物
US8568701B2 (en) Cationic synthetic polymers with improved solubility and performance in phosphate surfactant-based systems and use in personal care and household applications
JPH07173029A (ja) 化粧品基材
WO2025149373A1 (fr) Galactomannanes cationiques issus de guar et leur procédé de production
US9561166B2 (en) Polysaccharide products with improved performance and clarity in phosphate ester surfactant-based aqueous formulations and process for preparation
WO2025087800A1 (fr) Compositions présentant des galactomannanes cationiques
WO2025087799A1 (fr) Compositions contenant des galactomannanes cationiques

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: 24850237

Country of ref document: EP

Kind code of ref document: A1