Hair conditioner ingredients

Abstract

A hair conditioner formulation comprising a dermatologically acceptable vehicle and a conditioning polymer, the conditioning polymer being a dextran polymer crosslinked with a dextran crosslinker of formula (I), wherein X is a halogen and each R 1 is independently substituted or unsubstituted C 1~6 alkyl group, each R2 being independently selected from 1~6 wherein Y is selected from the group consisting of alkanediyl groups and Y is a divalent bridging group. [Formula 1] JPEG2024511311000019.jpg19170

Description

Technical Field

[0001] The present invention relates to hair conditioner formulations. Specifically, the present invention is a hair conditioner formulation comprising a dermatologically acceptable vehicle and a conditioning polymer, wherein the conditioning polymer is a dextran polymer crosslinked with a dextran crosslinking agent of formula (I),

[0002]

Chemical Formula

[0003] Conventional hair conditioners are popular among consumers for treating hair. Silicone-based conditioning agents are the most commonly used conditioning agents in hair conditioner formulations. However, there is growing concern among some consumers regarding the persistence and potential toxicity of certain silicone-based conditioning agents in the environment, particularly D4 and D5 conditioners. Therefore, there is increasing interest in the development of alternative conditioning agents that do not contain silicone for use in hair conditioner formulations.

[0004] In U.S. Patent No. 5,879,670, Melby et al. disclose non-silicone-containing amphoteric polymers for use as conditioning agents for the treatment of keratin-containing substrates. Specifically, Melby et al. disclose (meth)acrylamidopropyltrimethylammonium chloride, meth(acrylic acid) or 2-(meth)acrylamido-2-methylpropanesulfonic acid, and optionally, C 1~22Disclosed are novel conditioning polymers containing alkyl (meth)acrylate and their use in a cosmetically acceptable medium for the treatment of keratin-containing substrates.

[0005] Nevertheless, there is a continuing need for novel hair conditioning agents that provide conditioning benefits. There is also a continuing need for novel hair conditioning agents that have an increased natural origin index (ISO 16128) compared to conventional hair conditioning agents.

[0006] The present invention provides a hair conditioner formulation comprising a dermatologically acceptable vehicle and a conditioning polymer, wherein the conditioning polymer is a dextran polymer crosslinked with a dextran crosslinking agent of formula (I),

[0007]

Chemical formula

[0008] The present invention provides a hair conditioner formulation comprising a dermatologically acceptable vehicle and a conditioning polymer, wherein the conditioning polymer is a dextran polymer crosslinked with a dextran crosslinking agent of formula (I),

[0009]

Chemical formula

[0010] The present invention relates to a hair conditioner formulation comprising a dermatologically acceptable vehicle and a conditioning polymer, wherein the conditioning polymer is a dextran polymer crosslinked with a dextran crosslinking agent of formula (I).

[0011] [ka] In the formula, X is a halogen, and each R 1 However, independently, substitution or non-substitution C 1~6 Selected from alkyl groups, each R 2 However, independently, C 1~6 The present invention provides a hair conditioner formulation in which Y is a divalent crosslinking group selected from the group consisting of alkanediyl groups, and the hair conditioner formulation contains less than 0.1% by weight of silicone-containing molecules based on the weight of the hair conditioner formulation.

[0012] The present invention relates to a hair conditioner formulation comprising a dermatologically acceptable vehicle and a conditioning polymer, wherein the conditioning polymer is a dextran polymer crosslinked with a dextran crosslinking agent of formula (I).

[0013] [ka] In the formula, X is a halogen, and each R 1 However, independently, substitution or non-substitution C 1~6 Selected from alkyl groups, each R 2 However, independently, C 1~6The present invention provides a hair conditioner formulation comprising a group selected from the group consisting of alkanediyl groups, wherein Y is a divalent crosslinking group, the hair conditioner formulation contains less than 0.01% by weight of dermatologically acceptable oils based on the weight of the hair conditioner formulation, and the hair conditioner formulation contains less than 0.1% by weight of silicone-containing molecules based on the weight of the hair conditioner formulation.

[0014] The present invention provides a method for conditioning mammalian hair, comprising selecting a hair conditioner formulation of the present invention and applying the hair conditioner formulation to mammalian hair. [Modes for carrying out the invention]

[0015] Surprisingly, the present inventors have found a dextran polymer crosslinked with a dextran crosslinking agent of formula (I),

[0016] [ka] In the formula, X is a halogen, and each R 1 However, independently, substitution or non-substitution C 1~6 Selected from alkyl groups, each R 2 However, independently, C 1~6 We found that a dextran polymer, selected from the group consisting of alkanediyl groups, in which Y is a divalent crosslinking group, acts as a conditioning polymer that effectively restores hydrophobicity to damaged hair and reduces the force required to comb treated hair.

[0017] Unless otherwise specified, ratios, percentages, and parts are expressed by weight.

[0018] As used herein, unless otherwise indicated, "molecular weight" or M WThe term refers to weight-average molecular weight measured in the conventional manner using gel permeation chromatography (GPC) and conventional standards such as polyethylene glycol standards. The GPC technique is discussed in detail in *Modern Size Exclusion Chromatography*, WWYau, JJ Kirkland, DDBly; Wiley-Interscience, 1979, and *A Guide to Materials Characterization and Chemical Analysis*, JPSibilia; VCH, 1988, pp. 81-84. Molecular weight is reported herein in units of Daltons or equivalently in g / moles.

[0019] As used herein and in the appendices, the term “dermatologically acceptable” refers to ingredients typically used for topical application to the skin, and it is intended to emphasize that materials that are toxic when present in amounts typically found in skincare compositions are not intended as part of the present invention.

[0020] Preferably, the hair conditioner formulation of the present invention is selected from the group consisting of conditioning shampoo formulations, rinse-off conditioner formulations, and leave-on conditioner formulations. More preferably, the hair conditioner formulation of the present invention is selected from the group consisting of rinse-off conditioner formulations and leave-on conditioner formulations. Most preferably, the hair conditioner formulation of the present invention is a rinse-off conditioner formulation.

[0021] Preferably, the hair conditioner formulation of the present invention comprises a dermatologically acceptable vehicle (preferably, the hair conditioner formulation contains 50 to 99.9% by weight (preferably 75 to 99.85% by weight, more preferably 80 to 99.8% by weight, most preferably 90 to 99.75% by weight) of a dermatologically acceptable vehicle based on the weight of the hair conditioner formulation) and a conditioning polymer (preferably, the hair conditioner formulation contains 0.1 to 1% by weight (preferably 0.15 to 0.75% by weight, more preferably 0.2 to 0.5% by weight, most preferably 0.25 to 0.4% by weight) of a tertiary amine-functionalized dextran polymer based on the weight of the hair conditioner formulation), wherein the conditioning polymer is a dextran polymer crosslinked with a dextran crosslinking agent of formula (I).

[0022] [ka] In the formula, X is a halogen, and each R 1 These are independently substituted or non-substituted C 1~6 Selected from alkyl groups, each R 2 Independently, C 1~6 Selected from the group consisting of alkanediyl groups, Y is a divalent crosslinking group, and the conditioning polymer improves the adhesion of dermatologically acceptable silicones from hair conditioner formulations to mammalian hair.

[0023] Preferably, the hair conditioner formulation of the present invention is a liquid formulation. More preferably, the hair conditioner formulation of the present invention is an aqueous liquid formulation.

[0024] Preferably, the hair conditioner formulation of the present invention contains 50 to 99.9% by weight (preferably 75 to 99.85% by weight, more preferably 80 to 99.8% by weight, most preferably 90 to 99.75% by weight) of a dermatologically acceptable vehicle, based on the weight of the hair conditioner formulation. More preferably, the hair conditioner formulation of the present invention contains 50 to 99.9% by weight (preferably 75 to 99.85% by weight, more preferably 80 to 99.8% by weight, most preferably 90 to 99.75% by weight) of a dermatologically acceptable vehicle, based on the weight of the hair conditioner formulation, wherein the dermatologically acceptable vehicle includes water. More preferably, the hair conditioner formulation of the present invention contains 50 to 99.9% by weight (preferably 75 to 99.85% by weight, more preferably 80 to 99.8% by weight, most preferably 90 to 99.75% by weight) of a dermatologically acceptable vehicle, based on the weight of the hair conditioner formulation, wherein the dermatologically acceptable vehicle is water and aqueous C 1~4 The alcohol mixture is selected from the group consisting of alcohol mixtures. Most preferably, the hair conditioner formulation of the present invention contains 50 to 99.9% by weight (preferably 75 to 99.85% by weight, more preferably 80 to 99.8% by weight, most preferably 90 to 99.75% by weight) of a dermatologically acceptable vehicle, based on the weight of the hair conditioner formulation, wherein the dermatologically acceptable vehicle is water.

[0025] Preferably, the water used in the hair conditioner formulation of the present invention is at least one of distilled water and deionized water. More preferably, the water used in the hair conditioner formulation of the present invention is distilled and deionized.

[0026] Preferably, the hair conditioner formulation of the present invention contains 0.1 to 1% by weight (preferably 0.15 to 0.75% by weight, more preferably 0.2 to 0.5% by weight, most preferably 0.25 to 0.4% by weight) of a conditioning polymer based on the weight of the hair conditioner formulation, wherein the conditioning polymer is a dextran polymer crosslinked with a dextran crosslinking agent of formula (I). More preferably, the hair conditioner formulation of the present invention comprises 0.1 to 1% by weight (preferably 0.15 to 0.75% by weight, more preferably 0.2 to 0.5% by weight, most preferably 0.25 to 0.4% by weight) of a conditioning polymer based on the weight of the hair conditioner formulation, wherein the conditioning polymer is a dextran polymer crosslinked with a dextran crosslinking agent of formula (I), and the conditioning polymer has a Kjeldahl nitrogen content, TKN (measured using a Buchi KjelMaster K-375 automated analyzer, as described in ASTM Method D-2364, and corrected for volatile substances and ash) of 0.5 to 5.0% by weight (preferably 0.75 to 4% by weight, more preferably 1 to 3.5% by weight, most preferably 1.5 to 3.0% by weight), corrected for ash and volatile substances.

[0027] Preferably, the dextran polymer has a weight-average molecular weight of 50,000 to 3,000,000 daltons (preferably 100,000 to 2,000,000 daltons, more preferably 125,000 to 1,000,000 daltons, even more preferably 130,000 to 650,000 daltons, and most preferably 145,000 to 525,000 daltons). More preferably, the dextran polymer has a weight-average molecular weight of 50,000 to 3,000,000 daltons (preferably 100,000 to 2,000,000 daltons, more preferably 125,000 to 1,000,000 daltons, even more preferably 130,000 to 650,000 daltons, and most preferably 145,000 to 525,000 daltons), and the dextran polymer contains multiple glucose structural units. The branched dextran polymer is such that 90-98 mol% (preferably 92.5-97.5 mol%, more preferably 93-97 mol%, most preferably 94-96 mol%) of glucose structural units are linked by α-D-1,6 bonds, and 2-10 mol% (preferably 2.5-7.5 mol%, more preferably 3-7 mol%, most preferably 4-6 mol%) of glucose structural units are linked by α-1,3 bonds. Most preferably, the dextran polymer has a weight-average molecular weight of 50,000 to 3,000,000 daltons (preferably 100,000 to 2,000,000 daltons, more preferably 125,000 to 1,000,000 daltons, even more preferably 130,000 to 650,000 daltons, most preferably 145,000 to 525,000 daltons), and the dextran polymer contains multiple glucose structural units. It is a branch-chain dextran polymer in which 90-98 mol% (preferably 92.5-97.5 mol%, more preferably 93-97 mol%, most preferably 94-96 mol%) of glucose structural units are linked by α-D-1,6 bonds, and 2-10 mol% (preferably 2.5-7.5 mol%, more preferably 3-7 mol%, most preferably 4-6 mol%) of glucose structural units are linked by α-1,3 bonds according to formula II.

[0028] [ka] In the formula, R is hydrogen, C 1~4 Alkyl alkyl groups, and hydroxy C 1~4 Selected from alkyl groups, the average branching from the dextran polymer backbone is less than or equal to 3 anhydrous glucose units.

[0029] Preferably, the dextran polymer contains less than 0.01% by weight of alternans based on the weight of the dextran polymer. More preferably, the dextran polymer contains less than 0.001% by weight of alternans based on the weight of the dextran polymer. Most preferably, the dextran polymer contains alternans below the detectable limit.

[0030] Preferably, the conditioning polymer is a dextran polymer crosslinked with a dextran crosslinking agent of formula (I),

[0031] [ka] In the formula, X is a halogen (preferably, each X is independently selected from the group consisting of -Cl, -Br, and -I, and more preferably, each X is -Cl), and each R 1 These are independently substituted or non-substituted C 1~6 Selected from alkyl groups ("substitution" means that the group in question contains at least one portion selected from halogen, hydroxyl, amino, or carboxyl groups) (preferably, each R 1 Independently, non-substituted C 1~6 Selected from alkyl groups, more preferably each R 1 R is independently selected from the group consisting of methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, sec-butyl group, pentyl group, isopentyl group, neopentyl group, hexyl group, and isohexyl group, and more preferably each R 1R is independently selected from the group consisting of methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, and sec-butyl group, and more preferably each R 1 R is independently selected from the group consisting of methyl, ethyl, propyl, and isopropyl groups, and more preferably each R 1 These are independently selected from the group consisting of methyl groups and ethyl groups, most preferably each R 1 ( is a methyl group), and each R 2 Independently, C 1~6 Alkanediyl group (preferably C 1~4 Alkanediyl group, more preferably C 1~2 Y is selected from the group consisting of an alkanediyl group, most preferably a -CH2- group, and Y is a divalent crosslinking group (preferably C 1~6 Alkanediyl group and -R 3 -OR 4 -Base (more preferably, -R 3 -OR 4 -Base) and R 3 and R 4 Independently, C 1~6 Alkanediyl group (preferably C 1~4 Alkanediyl group, more preferably C 1~3 Selected from the group consisting of an alkanediyl group, most preferably a -CH2CH2- group (preferably R 3 and R 4 (These are the same). More preferably, the conditioning polymer is a dextran polymer crosslinked with a dextran crosslinking agent of formula (I), and the dextran crosslinking agent of formula (I) is of formula (II),

[0032] [ka] In the formula, X is a halogen (preferably, each X is independently selected from the group consisting of -Cl, -Br, and -I, and more preferably, each X is -Cl), and each R 1 These are independently substituted or non-substituted C 1~6Selected from alkyl groups ("substitution" means that the group in question contains at least one portion selected from halogen, hydroxyl, amino, or carboxyl groups) (preferably, each R 1 Independently, non-substituted C 1~6 Selected from alkyl groups, more preferably each R 1 R is independently selected from the group consisting of methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, sec-butyl group, pentyl group, isopentyl group, neopentyl group, hexyl group, and isohexyl group, and more preferably each R 1 R is independently selected from the group consisting of methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, and sec-butyl group, and more preferably each R 1 R is independently selected from the group consisting of methyl, ethyl, propyl, and isopropyl groups, and more preferably each R 1 These are independently selected from the group consisting of methyl groups and ethyl groups, most preferably each R 1 ( is a methyl group), and each R 2 Independently, C 1~6 Alkanediyl group (preferably C 1~4 Alkanediyl group, more preferably C 1~2 Selected from the group consisting of an alkanediyl group, most preferably a -CH2- group, R 3 and R 4 Independently, C 1~6 Alkanediyl group (preferably C 1~4 Alkanediyl group, more preferably C 1~3 Selected from the group consisting of an alkanediyl group, most preferably a -CH2CH2- group (preferably R 3 and R 4 (These are the same). Most preferably, the conditioning polymer is

[0033] [ka] The dextran polymer is crosslinked with a dextran crosslinking agent of formula (I) selected from the group consisting of and mixtures thereof.

[0034] Preferably, the conditioning polymer contains less than 0.001 meg / gram (preferably less than 0.0001 meq / gram, more preferably less than 0.00001 meq / gram, most preferably less than the detection limit) of aldehyde functional groups.

[0035] Preferably, the conditioning polymer contains less than 0.1% (preferably less than 0.01%, more preferably less than 0.001%, most preferably less than the detection limit) of β-1,4 bonds between individual glucose units in the conditioning polymer.

[0036] Preferably, the conditioning polymer contains less than 0.1% (preferably less than 0.01%, more preferably less than 0.001%, most preferably less than the detection limit) of β-1,3 bonds between individual glucose units in the conditioning polymer.

[0037] Preferably, the conditioning polymer contains silicone-containing functional groups in amounts of less than 0.001 meq / gram (preferably less than 0.0001 meq / gram, more preferably less than 0.00001 meq / gram, and most preferably less than the detection limit).

[0038] Preferably, the hair conditioner formulation of the present invention contains less than 0.01% by weight (preferably less than 0.001% by weight, more preferably less than 0.0001% by weight, and most preferably less than the detection limit) of dermatologically acceptable oils based on the weight of the hair conditioner formulation. More preferably, the hair conditioner formulation of the present invention contains less than 0.01% by weight (preferably less than 0.001% by weight, more preferably less than 0.0001% by weight, most preferably less than the detection limit) of dermatologically acceptable oils based on the weight of the hair conditioner formulation, and the dermatologically acceptable oils are selected from the group consisting of hydrocarbon oils (e.g., mineral oil, petrolatum, polyisobutene, hydrogenated polyisobutene, hydrogenated polydecene, polyisohexadecane, natural oils (e.g., caprylic and capric triglycerides, sunflower oil, soybean oil, coconut oil, argan oil, olive oil, almond oil)), fragrance oils (e.g., limonene), and mixtures thereof.

[0039] Preferably, the hair conditioner formulation of the present invention contains less than 0.1% by weight (preferably less than 0.001% by weight, more preferably less than 0.0001% by weight, most preferably less than the detection limit) of silicone (e.g., polydimethylsiloxane, dimethicone, cyclodimethicone, aminosilicone) based on the weight of the hair conditioner formulation.

[0040] Preferably, the hair conditioner formulation of the present invention contains less than 0.1% by weight (preferably less than 0.001% by weight, more preferably less than 0.0001% by weight, and most preferably less than the detection limit) of silicon (Si)-containing molecules based on the weight of the hair conditioner formulation.

[0041] Preferably, the hair conditioner formulation of the present invention optionally contains antimicrobial agents / preservatives (e.g., benzoic acid, sorbic acid, phenoxyethanol, methylisothiazolinone), rheological modifiers (e.g., hydroxyethylcellulose, PEG-150 pentaerythrityl tetrastearate), soap, colorants, pH adjusters, antioxidants (e.g., butylated hydroxytoluene), humectants (e.g., glycerin, sorbitol, monoglycerides, lecithin, glycolipids, fatty alcohols, fatty acids, polysaccharides, sorbitan esters, polysorbates (e.g., polysorbate 20, polysorbate 40, polysorbate 60, and polysorbate 80), diols (e.g., propylene glycol), triols, cationic polymers) The product further comprises at least one additional ingredient selected from the group consisting of polyols, waxes, foaming agents, emulsifiers, colorants, fragrances, chelating agents (e.g., tetrasodium ethylenediaminetetraacetate), preservatives (e.g., benzoic acid, sorbic acid, phenoxyethanol, methylisothiazolinone), bleaching agents, lubricants, sensory modifiers, sunscreen additives, vitamins, proteins / amino acids, plant extracts, natural ingredients, bioactives, degradation inhibitors, pigments, acids, penetrating agents, antistatic agents, anti-frizzy agents, anti-dandruff agents, hair weaving / straightening agents, hair styling agents, absorbents, hard particles, soft particles, conditioning agents (e.g., guar hydroxypropyltrimonium chloride, PQ-10, PQ-7), slip agents, opacifiers, pearlescent agents, and salts. More preferably, the hair conditioner formulation of the present invention further optionally comprises at least one additional component selected from the group consisting of antimicrobial agents / preservatives (e.g., benzoic acid, sorbic acid, phenoxyethanol, methylisothiazolinone), rheological modifiers (e.g., hydroxyethylcellulose, PEG-150 pentaerythrityl tetrastearate), and chelating agents (e.g., tetrasodium ethylenediaminetetraacetate). Most preferably, the hair conditioner formulation of the present invention further optionally comprises at least one additional component selected from the group consisting of hydroxyethylcellulose, tetrasodium ethylenediaminetetraacetate, combinations of phenoxyethanol and methylisothiazolinone, and mixtures thereof.

[0042] Preferably, the hair conditioner formulation of the present invention further comprises a thickening agent. More preferably, the hair conditioner formulation further comprises a thickening agent, which is preferably selected to increase the viscosity of the hair conditioner formulation without substantially altering other properties of the hair conditioner formulation. Preferably, the hair conditioner formulation of the present invention further comprises 0 to 5.0% by weight (preferably 0.1 to 5.0% by weight, more preferably 0.2 to 2.5% by weight, most preferably 0.5 to 2.0% by weight) of a thickening agent based on the weight of the hair conditioner formulation, which is preferably selected to increase the viscosity of the hair conditioner formulation without substantially altering other properties of the hair conditioner formulation. More preferably, the hair conditioner formulation of the present invention further comprises 0.1 to 5.0% by weight (preferably 0.2 to 2.5% by weight, more preferably 0.5 to 2.0% by weight) of a thickening agent based on the weight of the hair conditioner formulation, wherein the thickening agent comprises hydroxyethylcellulose. Most preferably, the hair conditioner formulation of the present invention further comprises 0.1 to 5.0% by weight (preferably 0.2 to 2.5% by weight, more preferably 0.5 to 2.0% by weight) of a thickening agent based on the weight of the hair conditioner formulation, wherein the thickening agent is hydroxyethylcellulose.

[0043] Preferably, the hair conditioner formulation of the present invention further comprises an antimicrobial agent / preservative. More preferably, the hair conditioner formulation of the present invention further comprises an antimicrobial agent / preservative, the antimicrobial agent / preservative being selected from the group consisting of phenoxyethanol, benzoic acid, benzyl alcohol, sodium benzoate, DMDM ​​hydantoin, 2-ethylhexylglyceryl ether, isothiazolinone (e.g., methylchloroisothiazolinone, methylisothiazolinone), and mixtures thereof. Even more preferably, the hair conditioner formulation of the present invention further comprises an antimicrobial agent / preservative, the antimicrobial agent / preservative being a mixture of phenoxyethanol and isothiazolinone (more preferably, the antimicrobial agent / preservative being a mixture of phenoxyethanol and methylisothiazolinone).

[0044] Preferably, the hair conditioner formulation of the present invention further optionally comprises a pH adjuster. More preferably, the hair conditioner formulation of the present invention further comprises a pH adjuster, and the hair conditioner formulation has a pH of 4 to 9 (preferably 4.25 to 8, more preferably 4.5 to 7, most preferably 4.75 to 6).

[0045] Preferably, the pH adjusting agent is selected from the group consisting of at least one of citric acid, lactic acid, hydrochloric acid, aminoethylpropanediol, triethanolamine, monoethanolamine, sodium hydroxide, potassium hydroxide, and amino-2-methyl-1-propanol. More preferably, the pH adjusting agent is selected from the group consisting of at least one of citric acid, lactic acid, sodium hydroxide, potassium hydroxide, triethanolamine, and amino-2-methyl-1-propanol. Even more preferably, the pH adjusting agent includes citric acid. Most preferably, the pH adjusting agent is citric acid.

[0046] Preferably, the method for conditioning mammalian hair according to the present invention comprises selecting a hair conditioner formulation according to the present invention and applying the hair conditioner formulation to the mammalian hair. Preferably, the method for conditioning mammalian hair according to the present invention further comprises wetting the hair with water before applying the hair conditioner. Most preferably, the method for conditioning mammalian hair according to the present invention comprises selecting a hair conditioner formulation according to the present invention, wetting the mammalian hair, and applying the hair conditioner formulation to the wet mammalian hair.

[0047] Herein, several embodiments of the present invention will be described in detail by the following examples.

[0048] Example S1: Synthesis of dextran crosslinking agent Bis[2-(N,N-dimethylamino)ethyl] ether (10.84 g) and water (23.12 g) were mixed together in a container. The pH of the contents of the container was adjusted to 8.5 with concentrated hydrochloric acid. 99.9% epichlorohydrin (20.84 g) was added to the container over 60 minutes while maintaining the setpoint temperature of the contents at 25°C. After maintaining the setpoint temperature of the contents at 25°C for another 2 hours, the setpoint temperature was raised to 50°C and maintained at that temperature for 2 hours. Next, the pH of the contents of the container was lowered to less than 2.0 with concentrated hydrochloric acid, the setpoint temperature was raised to 70°C and maintained at that temperature for 1 hour. Then, the contents of the container were cooled. Once the temperature of the contents of the container fell below 50°C, the pH of the contents was adjusted to 4-6 with a 50% sodium hydroxide solution. Next, the contents of the container were extracted seven times with methylene chloride (1 volume:1 volume), and then the residual methylene chloride was removed by the conventional method. The recovered material contained 39.4% by weight of product solids. The product solids were then removed. 13 The product was analyzed via 13C NMR,

[0049] [ka] It was confirmed to be N,N'-(oxybis(ethane-2,1-diyl))bis(3-chloro-2-hydroxy-N,N-dimethylpropane-1-aminium)chloride.

[0050] Example S2: Synthesis of crosslinked dextran polymer A 500 mL four-necked round-bottom flask equipped with a rubber septum cap, a nitrogen inlet, a pressure equalization funnel, a stirring paddle and motor, a subsurface thermocouple connected to a J-KEM controller, and a Friedrich condenser connected to a mineral oil bubbler was charged with dextran (23.23 g; Aldrich product number D4876) and deionized water (120 g). The weight-average molecular weight of dextran was 100,000–200,000 Daltons. While stirring the contents, the apparatus was purged with nitrogen to remove any oxygen introduced into the system. The nitrogen flow rate was approximately 1 bubble per second. The mixture was purged with nitrogen while stirring for 1 hour. Using a plastic syringe, a 50% sodium hydroxide aqueous solution (14.9 g) was added to the contents of the flask over several minutes while stirring under nitrogen. The contents of the flask were then stirred under nitrogen for 30 minutes. Next, a 47% aqueous solution (74.45 g) of the dextran crosslinking agent prepared according to Example S1 was added to the contents of the flask and stirred for 5 minutes before heating. Then, the contents of the flask were heated using a heating mantle controlled by a J-KEM controller set to 55°C. The contents of the flask were heated to 55°C and maintained at that temperature for 90 minutes. Then, the contents of the flask were cooled to room temperature while maintaining a positive nitrogen pressure inside the flask. Once the contents of the flask reached room temperature, the contents of the flask were neutralized by adding glacial acetic acid (3.0 g) and stirred for 10 minutes. Then, the contents of the flask were diluted and transferred without purification for use, and the content of the diluted product solids was 11.1% by weight. Aliquots of the solution were precipitated from methanol and dried under vacuum at 50°C. The total Kjeldahl nitrogen content (TKN) of the dried precipitate was measured at 2.72% by weight using a Buchi KjelMaster K-375 automated analyzer.

[0051] Comparative Examples CF1-CF3 and Example F1: Rinse-off Conditioner Formulations Rinse-off conditioner formulations were prepared in each of the Comparative Examples CF1 to CF3 and Example F1, which have the formulations listed in Table 1.

[0052] [Table 1]

[0053] Hair conditioning performance A study to evaluate the ease of combing hair treated with the rinse-off conditioner formulations of Comparative Examples CF1-CF3 and Example F1, both wet and dry, was conducted as follows. Slightly bleached Caucasian hair from International Hair Importers was used to test the conditioners. Each hair section weighed 2 grams. Each hair section was rinsed for 30 seconds under running tap water at 40°C. Using a pipette, 0.4 grams of a solution containing 9% sodium lauryl sulfate was applied and lathered over the entire hair section for 30 seconds. The hair section was then rinsed under running water for 1 minute. Excess water was removed from each hair section by passing it between the index and middle fingers of the hand. The hair sections were then treated with the rinse-off conditioner formulations of Comparative Examples CF1-CF3 and Example F1 by massaging the formulation into wet / moist hair at a ratio of 0.4 g formulation / 1 g of hair for 1 minute. Next, rinse the hair with 40°C tap water for 30 seconds. Remove excess water by pulling the hair through your index and middle fingers. Place the hair on a tray covered with paper towels and let it dry at room temperature overnight.

[0054] The coefficient of friction is an industry-standard method for measuring the reduction of frictional properties in hair processing and correlates with the subjective attributes of smoothness and softness. For testing in a temperature and humidity-controlled room, a Diastron MTT175 tensile testing machine with a rubber probe fitted with a 50g normal force was used. Two hair strands were tested per processing stage, and five measurements were taken from each strand to generate the average friction data reported in Table 2. The coefficient of friction (COF) = F / N, where F is the externally applied force and N is the normal force.

[0055] [Table 2]

[0056] An INSTRON Model 4464 running BlueHill2 software was also used to determine conditioning performance based on the ease of combing when wet and when dry. The tests utilized INSTRON strain gauges to measure the force required to comb the hair. Conditioning performance was based on the ability of the rinse-off conditioner formulation to reduce the force required to comb the hair using the INSTRON strain gauges. The force was reported as Average Combing Load (ACL). A lower ACL value indicates a greater conditioning effect provided by the rinse-off conditioner formulation being tested.

[0057] Following INSTRON's wet combing method, the hair was first wet by immersing it in distilled water, and then detangled by combining the hair strands three times. The hair strands were then tangled again by immersing them in distilled water three more times. Excess water was removed from the hair strands by passing the index and middle fingers of the hand twice. The hair strands were placed on a hanger and combed with an INSTRON comb. The average wet combing force from the three hair strands was measured for each rinse-off conditioner formulation. The average wet combing results are shown in Table 3.

[0058] Following INSTRON's drying combination method, hair strands were detangled by combining them three times. The hair was then re-tangled by rotating the strands three times clockwise and three times counterclockwise. The strands were then placed on hangers and combed with an INSTRON comb. The average drying combination force from the three strands was measured for each rinse-off conditioner formulation. The average drying combination results are shown in Table 3.

[0059] [Table 3]

[0060] Hydrophobicity of hair Rinse-off hair conditioners prepared according to Comparative Example CF2 and Example F1 were tested on two separate 3g hair samples (lightly bleached Caucasian hair, International Hair Importers, Inc.). The hair samples were first rinsed with water for 30 seconds. Then, a 9% (wt / wt) aqueous solution of sodium lauryl sulfate was massaged into the hair samples for 60 seconds. The hair samples were then rinsed with water for 30 seconds. Next, the hair samples were treated with 0.4g / g or the hair's dose of rinse-off hair conditioner and massaged into the hair for 30 seconds. The hair samples were then rinsed with water for 30 seconds and dried before the hydrophobicity test.

[0061] To measure the hydrophobicity of the hair, strands of hair were combed straight and held firmly at both ends with a holder. Ten drops of water were placed at different locations on each strand of hair, from root to tip. It was observed that the water immediately dissipated from the strands of hair treated with the formulation of Comparative Example CF2, while the water remained beaded on the strands of hair treated with the formulation of Example F1 even after 20 minutes, indicating that the rinse-off conditioner formulation of Example F1 successfully restored the hydrophobic benefit to slightly bleached Caucasian hair.

Claims

1. A hair conditioner formulation, The hair conditioner formulation comprises 50 to 99.9% by weight of a dermatologically acceptable vehicle and 0.1 to 1% by weight of a conditioning polymer, based on the weight of the hair conditioner formulation. The dermatologically acceptable vehicle is water. The conditioning polymer is of formula (I): 【Chemistry 1】 (In the formula, X is a halogen, and each R) １ These are independently substituted or non-substituted C １～６ Selected from alkyl groups, each R ２ Independently, C １～６ (Selected from the group consisting of alkanediyl groups, where Y is a divalent bridging group.) It is a dextran polymer crosslinked with a dextran crosslinking agent, A hair conditioner formulation wherein the hair conditioner formulation contains less than 0.001% by weight of dermatologically acceptable oils based on the weight of the hair conditioner formulation, and also contains less than 0.001% by weight of silicone-containing molecules based on the weight of the hair conditioner formulation.

2. The hair conditioner formulation according to claim 1, wherein the hair conditioner formulation contains less than 0.0001% by weight of dermatologically acceptable oils based on the weight of the hair conditioner formulation.

3. The hair conditioner formulation according to claim 2, wherein the hair conditioner formulation contains less than 0.0001% by weight of silicone-containing molecules based on the weight of the hair conditioner formulation.

4. The hair conditioner formulation according to claim 3, wherein the hair conditioner formulation is selected from the group consisting of rinse-off conditioner formulations and leave-in conditioner formulations.

5. The hair conditioner formulation according to claim 4, wherein the hair conditioner formulation is a rinse-off conditioner formulation.

6. The hair conditioner formulation according to claim 5, wherein the dextran polymer crosslinked with the dextran crosslinking agent of formula (I) has a Kjeldahl nitrogen content (TKN) of 0.5 to 5.0% by weight, and the Kjeldahl nitrogen content is corrected for ash and volatile substances.

7. The dextran crosslinking agent of formula (I) is 【Chemistry 2】 A hair conditioner formulation according to claim 6, selected from the group consisting of and mixtures thereof.

8. The hair conditioner formulation according to claim 7, further comprising a thickening agent.

9. The hair conditioner formulation according to claim 8, further comprising a preservative.

10. A method for conditioning mammalian hair, Selecting the hair conditioner formulation described in claim 1, and A method comprising applying the hair conditioner formulation to the hair of a mammal.

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