Hair Conditioner Formulation
A dextran-based polymer with morpholine and quaternary ammonium groups addresses the need for silicone-free hair conditioners by improving hydrophobicity and combing ease, enhancing the natural origin index.
Patent Information
- Application Number
- JP2024554752
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2022-03-22
- Filing Date
- 2023-03-20
- Publication Date
- 2025-04-11
AI Technical Summary
There is a growing concern among consumers about the persistence and potential toxicity of silicone-based conditioning agents in hair care products, prompting a need for silicone-free alternatives that provide effective conditioning benefits and a high natural origin index.
A hair conditioner formulation using a dextran-based polymer functionalized with morpholine groups and quaternary ammonium groups, which are attached to pendant oxygens on the dextran backbone, offering a cationic conditioning agent with a weight average molecular weight between 10,000 to 3,000,000 Daltons, providing improved hydrophobicity and reduced combing force.
The formulation effectively restores hydrophobicity and reduces the force required to comb treated hair while enhancing the natural origin index compared to conventional agents, without using silicone-based compounds.
Smart Images
Figure 2025509550000001_ABST
Abstract
Description
[Technical field]
[0001] The present invention relates to a hair conditioner formulation. In particular, the present invention relates to a hair conditioner formulation comprising a dermatologically acceptable vehicle and a conditioning polymer, the conditioning polymer being a dextran-based polymer functionalized with morpholine groups and quaternary ammonium groups, the dextran-based polymer having a weight average molecular weight of 10,000 to 3,000,000 Daltons, the morpholine groups being of formula (II) attached to pendant oxygens on the dextran-based polymer;
[0002] [ka] The quaternary ammonium group is a quaternary ammonium group of formula (III) attached to a pendant oxygen on the dextran base polymer,
[0003] [ka] During the ceremony,
[0004] [ka] are pendant oxygens on the dextran-based polymer, A is a divalent linking group, X is a divalent linking group, and each R 2 are independently linear or branched C 1~4 alkyl group, each R 3 are independently linear or branched C 8~20 The alkyl group is selected from the group consisting of aryl, ... and alkyl groups.
[0005] Traditional hair conditioners are popular with consumers to treat hair.Silicone-based conditioning agents are the most commonly used conditioning agents in hair conditioner formulations.However, there is growing concern among some consumers about the persistence and potential toxicity of certain silicone-based conditioning agents in the environment, or trace compounds incorporated in such silicone-based conditioning agents, particularly with respect to D4 and D5 conditioners.Therefore, there is growing interest in developing silicone-free alternative conditioning agents for use in hair conditioner formulations.
[0006] In U.S. Patent No. 5,879,670, Melby et al. disclose non-silicon-containing ampholyte polymers for use as conditioning agents for the treatment of keratin-containing substrates. In particular, Melby et al. disclose a non-silicon-containing ampholyte polymer comprising (meth)acrylamidopropyltrimethylammonium chloride, meth(acrylic acid) or 2-(meth)acrylamido-2-methylpropanesulfonic acid, and optionally C 1~22 Novel conditioning polymers containing alkyl (meth)acrylates and their use in a cosmetically acceptable medium for the treatment of keratin-containing substrates, preferably mammalian hair, more preferably human hair, are disclosed.
[0007] Nonetheless, there is a continuing need for new hair conditioning agents that provide conditioning benefits. Also, there is a continuing need for new hair conditioning agents that have a high natural origin index (ISO 16128) compared to conventional hair conditioning agents.
[0008] The present invention provides a hair conditioner formulation comprising a dermatologically acceptable vehicle and a conditioning polymer, the conditioning polymer being a cationic dextran polymer comprising a dextran base polymer functionalized with morpholine groups and quaternary ammonium groups, the dextran base polymer having a weight average molecular weight of from 10,000 to 3,000,000 Daltons, the morpholine groups being morpholine groups of formula (II) attached to pendant oxygens on the dextran base polymer, and the quaternary ammonium groups being quaternary ammonium groups of formula (III) attached to pendant oxygens on the dextran base polymer;
[0009] [ka] During the ceremony,
[0010] [ka] are pendant oxygens on the dextran-based polymer, A is a divalent linking group, X is a divalent linking group, and each R 2 are independently linear or branched C 1~4 Alkyl groups (preferably linear or branched C 1~3 Alkyl groups, more preferably C 1~2 alkyl group, and most preferably a methyl group; 3 are independently linear or branched C 8~20 The alkyl group is selected from the group consisting of aryl, ... and alkyl groups.
[0011] The present invention provides a hair conditioner formulation comprising a dermatologically acceptable vehicle and a conditioning polymer, the conditioning polymer being a cationic dextran polymer comprising a dextran base polymer functionalized with morpholine groups and quaternary ammonium groups, the dextran base polymer having a weight average molecular weight of from 10,000 to 3,000,000 Daltons, the morpholine groups being morpholine groups of formula (II) attached to pendant oxygens on the dextran base polymer and the quaternary ammonium groups being quaternary ammonium groups of formula (III) attached to pendant oxygens on the dextran base polymer;
[0012] [ka] are pendant oxygens on the dextran-based polymer, A is a divalent linking group, X is a divalent linking group, and each R 2 are independently linear or branched C 1~4 Alkyl groups (preferably linear or branched C 1~3 Alkyl groups, more preferably C 1~2 alkyl group, and most preferably a methyl group; 3 are independently linear or branched C 8~20 alkyl groups; the hair conditioner formulation contains less than 0.01% by weight of octamethylcyclotetrasiloxane (D4), decamethylcyclopentasiloxane (D5), and dodecamethylcyclohexasiloxane (D6), based on the weight of the hair conditioner formulation.
[0013] The present invention provides a method of conditioning hair comprising selecting a hair conditioner formulation of the present invention and applying the hair conditioner formulation to the hair. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
[0014] The inventors have surprisingly discovered a cationic dextran polymer comprising a dextran base polymer functionalized with morpholine groups and quaternary ammonium groups, the dextran base polymer having a weight average molecular weight of from 10,000 to 3,000,000 Daltons, the morpholine groups being of formula (II) attached to pendant oxygens on the dextran base polymer,
[0015] [ka] The quaternary ammonium group is a quaternary ammonium group of formula (III) attached to a pendant oxygen on the dextran base polymer,
[0016] [ka] During the ceremony,
[0017] [ka] are pendant oxygens on the dextran-based polymer, A is a divalent linking group, X is a divalent linking group, and each R 2 are independently linear or branched C 1~4 alkyl group, each R 3 are independently linear or branched C 8~20 It has been found that the alkyl groups selected from these act as conditioning polymers that effectively restore the hydrophobicity of damaged hair and reduce the force required to comb treated hair, while also providing an improved natural origin index (ISO 16128) compared to conventional hair conditioning agents.
[0018] Unless otherwise indicated, ratios, percentages, parts, etc. are by weight.
[0019] As used herein, unless otherwise indicated, "molecular weight" or M WThe phrase refers to weight average molecular weight measured in a conventional manner using gel permeation chromatography (GPC) and conventional standards such as polyethylene glycol standards. The technique of GPC is described in detail in Modern Size Exclusion Chromatography, WW Yau, JJ Kirkland, DDBly; Wiley-Interscience, 1979, and in A Guide to Materials Characterization and Chemical Analysis, JP Sibilia; VCH, 1988, p.81-84. Molecular weights are reported herein in units of Daltons, or equivalently, g / mol.
[0020] The term "dermatologically acceptable" as used in this specification and the appended claims refers to ingredients that are typically used for topical application to the skin, and is intended to emphasize that materials that are toxic when present in amounts typically found in skin care compositions are not contemplated as part of the present invention.
[0021] The term "damaged human hair" as used herein and in the appended claims refers to at least one of chemically damaged human hair (e.g., human hair damaged from chemical treatments such as dyeing, bleaching, perming, etc.), thermally damaged human hair (e.g., human hair damaged from exposure to heat by ironing, force drying, styling), and physically damaged human hair (e.g., human hair damaged from physical abuse such as rubbing, pulling, curling, etc.).
[0022] 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. More preferably, the hair conditioner formulation of the present invention is a rinse-off conditioner formulation.
[0023] Preferably, the hair conditioner formulation of the present invention comprises a dermatologically acceptable vehicle (preferably, the hair conditioner formulation comprises 25 to 99.9 wt. % (preferably, 48 to 99.85 wt. %, more preferably, 79 wt. % to 99.8 wt. %, most preferably, 84.5 to 99.75 wt. %) of a dermatologically acceptable vehicle based on the weight of the hair conditioner formulation), and a conditioning polymer (preferably, 0.05 to 5 wt. % (preferably, 0.1 wt. %, most preferably, 0.25 to 10 wt. %, based on the weight of the hair conditioner formulation). and a conditioning polymer of from 0.15% to 1% by weight, more preferably from 0.2% to 0.5% by weight, wherein the conditioning polymer is a cationic dextran polymer comprising a dextran base polymer functionalized with morpholine groups and quaternary ammonium groups, the dextran base polymer having a weight average molecular weight of from 10,000 to 3,000,000 Daltons, the morpholine groups being morpholine groups of formula (II) attached to pendant oxygens on the dextran base polymer;
[0024] [ka] The quaternary ammonium group is a quaternary ammonium group of formula (III) attached to a pendant oxygen on the dextran base polymer,
[0025] [ka] During the ceremony,
[0026] [ka] is a pendant oxygen on the dextran-based polymer, and A is a divalent linking group (preferably, A is selected from divalent alkyl groups, which may be optionally substituted with hydroxy, alkoxy, and / or ether groups, more preferably, A is -(CH2) yGroup and -CHCH(OR 4 ) CH2- group, where y is 2 to 5 (preferably 2 to 4), more preferably 2 to 3, and most preferably 2), R 4 is hydrogen and linear or branched C 1~4 and X is a divalent linking group (preferably, X is selected from a divalent alkyl group, which may optionally be substituted with a hydroxy group, an alkoxy group, and / or an ether group, more preferably, X is selected from the group consisting of a -CHCH(OH)CH- group, even more preferably, A is selected from the group consisting of a -CHCH- group and a -CHCH(OH)CH- group, most preferably, A is a -CHCH- group). 4 ) CH2- group, where R 4 is hydrogen and linear or branched C 1~4 alkyl groups), most preferably X is a -CHCH(OH)CH- group), and each R 2 are independently linear or branched C 1~4 Alkyl groups (preferably linear or branched C 1~3 Alkyl groups, more preferably C 1~2 alkyl group, and most preferably a methyl group; 3 are independently linear or branched C 8~20 Alkyl groups (preferably linear or branched C 10~16 Alkyl groups, more preferably linear or branched C 10~-14 Alkyl groups, even more preferably linear or branched C 12 Alkyl groups, most preferably linear C 12 alkyl group).
[0027] Preferably, the hair conditioner formulations of the present invention are liquid formulations. More preferably, the hair conditioner formulations of the present invention are aqueous liquid formulations.
[0028] Preferably, the hair conditioner formulation of the present invention comprises 25 to 99.9% by weight (preferably 48 to 99.85% by weight, more preferably 79% to 99.8% by weight, most preferably 84.5 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 comprises 25 to 99.9% by weight (preferably 48 to 99.85% by weight, more preferably 79% to 99.8% by weight, most preferably 84.5 to 99.75% by weight) of a dermatologically acceptable vehicle based on the weight of the hair conditioner formulation, the dermatologically acceptable vehicle comprising water. Even more preferably, the hair conditioner formulation of the present invention comprises from 25 to 99.9 wt. % (preferably from 48 to 99.85 wt. %, more preferably from 79 to 99.8 wt. %, and most preferably from 84.5 to 99.75 wt. %) of a dermatologically acceptable vehicle, based on the weight of the hair conditioner formulation, the dermatologically acceptable vehicle being selected from the group consisting of water and aqueous C12C14. 1~4 Most preferably, the hair conditioner formulation of the present invention comprises from 25 to 99.9% (preferably from 48 to 99.85%, more preferably from 79% to 99.8%, most preferably from 84.5 to 99.75%) by weight of the dermatologically acceptable vehicle, based on the weight of the hair conditioner formulation, the dermatologically acceptable vehicle being water.
[0029] Preferably, the water used in the hair conditioner formulations of the present invention is at least one of distilled water and deionized water. More preferably, the water used in the hair conditioner formulations of the present invention is distilled and deionized.
[0030] Preferably, the hair conditioner formulation of the present invention comprises 0.05 to 5 wt. % (preferably 0.1 to 2 wt. %, more preferably 0.15 wt. % to 1 wt. %, most preferably 0.2 to 0.5 wt. %) of a conditioning polymer based on the weight of the hair conditioner formulation, the conditioning polymer being a cationic dextran polymer comprising a dextran base polymer functionalized with morpholine groups and quaternary ammonium groups, the dextran base polymer having a weight average molecular weight of 10,000 to 3,000,000 Daltons, the morpholine groups being morpholine groups of formula (II) attached to pendant oxygens on the dextran base polymer, and the quaternary ammonium groups being quaternary ammonium groups of formula (III) attached to pendant oxygens on the dextran base polymer.
[0031] Preferably, the dextran-based polymer has a weight average molecular weight of 10,000 to 3,000,000 daltons (preferably 50,000 to 2,500,000 daltons, more preferably 100,000 to 2,000,000 daltons, even more preferably 125,000 to 1,000,000 daltons, and most preferably 140,000 to 500,000 daltons). More preferably, the dextran-based polymer has a weight-average molecular weight of 10,000 to 3,000,000 daltons (preferably, 50,000 to 2,500,000 daltons, more preferably, 100,000 to 2,000,000 daltons, even more preferably, 125,000 to 1,000,000 daltons, and most preferably, 140,000 to 500,000 daltons), and the dextran-based polymer is a branched-chain dextran polymer containing a plurality of glucose structural units. 90 mol % to 98 mol % (preferably 92.5 mol % to 97.5 mol %, more preferably 93 mol % to 97 mol %, and most preferably 94 mol % to 96 mol %) of the glucose structural units are connected via α-1,6 bonds, and 2 mol % to 10 mol % (preferably 2.5 mol % to 7.5 mol %, more preferably 3 mol % to 7 mol %, and most preferably 4 to 6 mol %) of the glucose structural units are connected via α-1,2 bonds, α-1,3 bonds, and / or α-1,4 bonds.Most preferably, the dextran-based polymer has a weight-average molecular weight of 10,000 to 3,000,000 daltons (preferably, 50,000 to 2,500,000 daltons, more preferably, 100,000 to 2,000,000 daltons, even more preferably, 125,000 to 1,000,000 daltons, and most preferably, 140,000 to 500,000 daltons), and the dextran-based polymer is a branched-chain dextran containing a plurality of glucose structural units. A polymer in which 90 mol % to 98 mol % (preferably 92.5 mol % to 97.5 mol %, more preferably 93 mol % to 97 mol %, most preferably 94 mol % to 96 mol %) of the glucose structural units are connected by α-D-1,6 bonds and 2 mol % to 10 mol % (preferably 2.5 mol % to 7.5 mol %, more preferably 3 mol % to 7 mol %, most preferably 4 to 6 mol %) of the glucose structural units are connected by α-1,3 bonds according to formula I.
[0032] [ka] In the formula, R 1 is hydrogen, C 1~4 Alkyl and hydroxy C 1~4 The alkyl groups are selected from the dextran polymer backbone with an average branch of 1 to 3 anhydroglucose units.
[0033] Preferably, the dextran-based polymer contains less than 0.01% by weight of alternan, based on the weight of the dextran-based polymer. More preferably, the dextran-based polymer contains less than 0.001% by weight of alternan, based on the weight of the dextran-based polymer. Most preferably, the dextran-based polymer contains less than the detectable limit of alternan.
[0034] Preferably, less than 0.1 mol % (preferably less than 0.01 mol %, more preferably less than 0.001 mol %, most preferably below the detection limit) of the glucose structural units in the dextran-based polymer are connected by β-1,4 bonds.
[0035] Preferably, less than 0.1 mol % (preferably less than 0.01 mol %, more preferably less than 0.001 mol %, most preferably below the detection limit) of the glucose structural units in the dextran-based polymer are connected by β-1,3 bonds.
[0036] Preferably, the hair conditioner formulation of the present invention comprises 0.05 to 5 wt. % (preferably 0.1 to 2 wt. %, more preferably 0.15 wt. % to 1 wt. %, most preferably 0.2 to 0.5 wt. %) of a conditioning polymer based on the weight of the hair conditioner formulation, the conditioning polymer being a cationic dextran polymer comprising a dextran base polymer functionalized with morpholine groups and quaternary ammonium groups, the morpholine groups being morpholine groups of formula (II) attached to pendant oxygens on the dextran base polymer and the quaternary ammonium groups being quaternary ammonium groups of formula (III) attached to pendant oxygens on the dextran base polymer;
[0037] [ka] During the ceremony,
[0038] [ka] is a pendant oxygen on the dextran-based polymer, and A is a divalent linking group (preferably, A is selected from divalent alkyl groups, which may be optionally substituted with hydroxy, alkoxy, and / or ether groups, more preferably, A is -(CH2) y Group and -CHCH(OR 4) CH2- groups, where y is 2 to 5 (preferably 2 to 4), more preferably 2 to 3, and most preferably 2); R 4 is hydrogen and linear or branched C 1~4 and X is a divalent linking group (preferably, X is selected from a divalent alkyl group, which may optionally be substituted with a hydroxy group, an alkoxy group, and / or an ether group, more preferably, X is selected from the group consisting of a -CHCH(OH)CH- group, even more preferably, A is selected from the group consisting of a -CHCH- group and a -CHCH(OH)CH- group; most preferably, A is a -CHCH- group). 4 ) CH2- group, where R 4 is hydrogen and linear or branched C 1~4 alkyl groups), most preferably X is a -CHCH(OH)CH- group), and each R 2 are independently linear or branched C 1~4 Alkyl groups (preferably linear or branched C 1~3 Alkyl groups, more preferably C 1~2 alkyl groups, and most preferably methyl groups; 3 are independently linear or branched C 8~20 Alkyl groups (preferably linear or branched C 10~16 Alkyl groups, more preferably linear or branched C 10~14 Alkyl groups, even more preferably linear or branched C 12 Alkyl groups, most preferably linear C 12 alkyl group) (preferably the degree of substitution DS of the morpholine group of formula (II) on the cationic dextran polymer) (II) is selected from 0.01 to 0.2 (preferably 0.02 to 0.175, more preferably 0.03 to 0.16, and most preferably 0.04 to 0.14), and the degree of substitution DS of the quaternary ammonium group of formula (III) on the cationic dextran polymer (III)is greater than 0 and equal to or less than 2 (preferably 0.1 to 2, more preferably 0.2 to 1.75, even more preferably 0.25 to 1.5, most preferably 0.3 to 1.2). More preferably, the hair conditioner formulation of the present invention comprises 0.05 to 5 wt. % (preferably 0.1 to 2 wt. %, more preferably 0.15 wt. % to 1 wt. %, most preferably 0.2 to 0.5 wt. %) of a conditioning polymer based on the weight of the hair care formulation, the conditioning polymer being a cationic dextran polymer comprising a dextran base polymer functionalized with a morpholine group and a quaternary ammonium group, the morpholine group being of formula (IIa) attached to a pendant oxygen on the dextran base polymer,
[0039] [ka] (ii) a quaternary ammonium group of formula (IIIa) attached to a pendant oxygen on a dextran base polymer;
[0040] [ka] During the ceremony,
[0041] [ka] are the pendant oxygens on the dextran-based polymer, and R 4 is hydrogen and linear or branched C 1~4 An alkyl group (preferably R 4 is hydrogen; 2 are independently linear or branched C 1~4 Alkyl groups (preferably C 1~3 Alkyl groups, more preferably C 1~2 alkyl group, and most preferably a methyl group; 3 are independently linear or branched C 8~20Alkyl groups (preferably linear or branched C 10~16 Alkyl groups, more preferably linear or branched C 10~14 Alkyl groups, even more preferably linear or branched C 12 Alkyl groups, most preferably linear C 1~12 alkyl group), and the degree of substitution DS of the morpholine group of formula (II) on the cationic dextran polymer II(II) is 0.01 to 0.2 (preferably 0.02 to 0.175, more preferably 0.03 to 0.16, and most preferably 0.04 to 0.14), and the substitution degree DS of the quaternary ammonium group of formula (III) on the cationic dextran polymer is (III) is greater than 0 and equal to or less than 2 (preferably 0.1 to 2, more preferably 0.2 to 1.75, even more preferably 0.25 to 1.5, and most preferably 0.3 to 1.2). Most preferably, the hair conditioner formulation of the present invention comprises 0.05 to 5 wt. % (preferably 0.1 to 2 wt. %, more preferably 0.15 wt. % to 1 wt. %, and most preferably 0.2 to 0.5 wt. %) of a conditioning polymer, based on the weight of the hair conditioner formulation, the conditioning polymer being a cationic dextran polymer comprising a dextran base polymer functionalized with a morpholine group and a quaternary ammonium group, the morpholine group being a morpholine group of formula (IIa) attached to a pendant oxygen on the dextran base polymer and the quaternary ammonium group being a quaternary ammonium group of formula (IIIa) attached to a pendant oxygen on the dextran base polymer, 2 is a methyl group, and each R 3 are independently linear or branched C 8~20 Alkyl groups (preferably linear or branched C 10~16 Alkyl groups, more preferably linear or branched C 10~14 Alkyl groups, even more preferably linear or branched C 12 Alkyl groups, most preferably linear C 1~12 alkyl group), each R 4 is hydrogen, and the degree of substitution DS of the morpholine group of formula (II) on the cationic dextran polymerII(II) is 0.01 to 0.2 (preferably 0.02 to 0.175, more preferably 0.03 to 0.16, and most preferably 0.04 to 0.14), and the substitution degree DS of the quaternary ammonium group of formula (III) on the cationic dextran polymer is (III) is greater than 0 and equal to or less than 2 (preferably 0.1 to 2, more preferably 0.2 to 1.75, even more preferably 0.25 to 1.5, and most preferably 0.3 to 1.2).
[0042] Preferably, the deposition aid polymer has a Kjeldahl nitrogen content TKN of 0.5 to 2.5 wt. % (preferably, 0.55 to 2.2 wt. %, more preferably, 0.6 wt. % to 2 wt. %, and most preferably, 0.65 to 1.75 wt. %) measured using a Buchi KjelMaster K-375 automated analyzer, corrected for volatile matter and ash content measured as described in ASTM method D-2364.
[0043] Preferably, the conditioning polymer contains less than 0.001 meq / gram (preferably less than 0.0001 meq / gram, more preferably less than 0.00001 meq / gram, most preferably below the limit of detectability) aldehyde functional groups.
[0044] Preferably, the conditioning polymer contains less than 0.1% (preferably less than 0.01%, more preferably less than 0.001%, and most preferably below the detectable limit) of linkages between individual glucose units in the conditioning polymer, which are β-1,4 linkages.
[0045] Preferably, the conditioning polymer contains less than 0.1% (preferably less than 0.01%, more preferably less than 0.001%, and most preferably below the detectable limit) of linkages between individual glucose units in the conditioning polymer, which are β-1,3 linkages.
[0046] Preferably, the conditioning polymer contains less than 0.001 meq / gram (preferably less than 0.0001 meq / gram, more preferably less than 0.00001 meq / gram, most preferably below the limit of detectability) of silicone-containing functional groups.
[0047] Preferably, the hair conditioner formulations of the present invention optionally contain antimicrobial agents / preservatives (e.g., benzoic acid, sorbic acid, phenoxyethanol, methylisothiazolinone, ethylhexylglycerin), rheology modifiers (e.g., PEG-150 pentaerythrityl tetrastearate), 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), diol analogs, triols, triols, etc. and at least one additional ingredient selected from the group consisting of: aromatic hydrocarbons, ... More preferably, the hair conditioner formulations of the present invention optionally further comprise at least one additional ingredient selected from the group consisting of antimicrobial / preservatives (e.g., benzoic acid, sorbic acid, phenoxyethanol, methylisothiazolinone, ethylhexylglycerin), rheology modifiers (e.g., PEG-150 pentaerythrityl tetrastearate), and chelating agents (e.g., tetrasodium ethylenediaminetetraacetate).Most preferably, the hair conditioner formulations of the present invention optionally further comprise at least one additional ingredient selected from the group consisting of a mixture of phenoxyethanol and methylisothiazolinone, a mixture of phenoxyethanol and ethylhexylglycerin, PEG-150 pentaerythrityl tetrastearate, and tetrasodium ethylenediaminetetraacetate.
[0048] Preferably, the hair conditioner formulation of the present invention further comprises a thickening agent. More preferably, the hair conditioner formulation of the present invention further comprises a thickening agent, 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 a thickening agent, preferably selected to increase the viscosity of the hair conditioner formulation without substantially altering other properties of the hair conditioner formulation, the thickening agent comprising 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) based on the weight of the hair conditioner formulation.
[0049] Preferably, the hair conditioner formulations of the present invention further comprise an antimicrobial / antiseptic agent. More preferably, the hair conditioner formulations of the present invention further comprise an antimicrobial / antiseptic agent, the antimicrobial / antiseptic agent being selected from the group consisting of phenoxyethanol, ethylhexylglycerin, benzoic acid, benzyl alcohol, sodium benzoate, DMDM hydantoin, 2-ethylhexylglyceryl ether, isothiazolinones (e.g., methylchloroisothiazolinone, methylisothiazolinone), and mixtures thereof. Most preferably, the hair conditioner formulations of the present invention further comprise an antimicrobial / preservative, wherein the antimicrobial / preservative is a mixture selected from the group consisting of (a) phenoxyethanol and ethylhexylglycerin, and (b) phenoxyethanol and an isothiazolinone. (More preferably, the antimicrobial / preservative is a mixture selected from the group consisting of (a) phenoxyethanol and ethylhexylglycerin, and (b) phenoxyethanol and methylisothiazolinone; most preferably, the antimicrobial / preservative is a mixture of phenoxyethanol and ethylhexylglycerin.)
[0050] Preferably, the hair conditioner formulation of the present invention optionally further comprises a pH adjusting agent. More preferably, the hair conditioner formulation of the present invention further comprises a pH adjusting agent 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).
[0051] Preferably, the pH adjuster 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 adjuster 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 adjuster contains citric acid. Most preferably, the pH adjuster is citric acid.
[0052] Preferably, the hair conditioner formulations of the present invention contain less than 0.01% by weight (preferably less than 0.001% by weight, more preferably less than 0.0001% by weight, most preferably below the detectable limit) of dermatologically acceptable non-silicone oils, based on the weight of the hair conditioner formulation. More preferably, the hair conditioner formulations of the present invention contain less than 0.01 wt. % (preferably less than 0.001 wt. %, more preferably less than 0.0001 wt. %, most preferably below the detectable limit) of a dermatologically acceptable non-silicone oil, based on the weight of the hair conditioner formulation, wherein the dermatologically acceptable non-silicone oil is 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), and mixtures thereof.
[0053] Preferably, the hair conditioner formulations of the present invention contain less than 0.01% (preferably less than 0.001%, more preferably less than 0.0001%, and most preferably below the limit of detection) of a combination of octamethylcyclotetrasiloxane (D4), decamethylcyclopentasiloxane (D5), and dodecamethylcyclohexasiloxane (D6) based on the weight of the hair conditioner formulation.
[0054] Preferably, the hair conditioner formulations of the present invention contain less than 0.01% (preferably less than 0.001%, more preferably less than 0.0001%, and most preferably below the detectable limit) by weight of conditioning silicones (e.g., polydimethylsiloxane, dimethicone) based on the weight of the hair conditioner formulation.
[0055] Preferably, hair conditioner formulations of the present invention contain less than 0.1 wt.% (preferably less than 0.001 wt.%, more preferably less than 0.0001 wt.%, most preferably below the detectable limit) of silicon (Si) containing molecules based on the weight of the hair conditioner formulation.
[0056] Preferably, the hair conditioner formulation is selected from the group consisting of leave-on hair conditioners or rinse-off hair care conditioners, and the hair conditioner formulation contains less than 0.1 wt. % (preferably less than 0.001 wt. %, more preferably less than 0.0001 wt. %, most preferably below the detectable limit) of hair care cleansing surfactant based on the weight of the hair conditioner formulation. More preferably, the hair conditioner formulation is selected from the group consisting of leave-on hair conditioners or rinse-off conditioners, and the hair conditioner formulation contains less than 0.1 wt. % (preferably less than 0.001 wt. %, more preferably less than 0.0001 wt. %, most preferably below the detectable limit) of hair care cleansing surfactant based on the weight of the hair conditioner formulation. Hair cleansing surfactants include alkyl polyglucosides (e.g., lauryl glucoside, coco-glucoside, decyl glucoside), glycinates (e.g., sodium cocoyl glycinate), betaines (e.g., alkyl betaines such as cetyl betaine, and amido betaines such as cocamidopropyl betaine), taurates (e.g., sodium methyl cocoyl taurate), glutamates (e.g., sodium cocoyl glutamate), sarcosinates (e.g., sodium lauroyl sarcosinate), isethionates (e.g., sodium cocoyl isethionate, sodium lauroyl methyl isethionate), sulfoacetates (e.g., sodium lauryl sulfoacetate), alaninates (e.g., sodium cocoyl alaninate), amphoacetates (e.g., sodium cocoamphoacetate), sulfates (e.g., sodium lauryl ether sulfate (SLES)), sulfonates (e.g., sodium lauryl ether sulfate (SLES)), and sulfonates (e.g., sodium lauryl ether sulfate (SLES)). 14~16sodium olefin sulfonate), succinates (e.g., disodium lauryl sulfosuccinate), fatty alkanolamines (e.g., cocamide monoethanolamine, cocamide diethanolamine, soyamide diethanolamine, lauramide diethanolamine, oleamide monoisopropanolamine, stearamide monoethanolamine, myristamide monoethanolamine, lauramide monoethanolamine, capramide diethanolamine, ricinoleamide diethanolamine, myristamide diethanolamine, stearamide diethanolamine, oleylamide diethanolamine, tallowamide diethanolamine, lauramide monoisopropanolamine, tallowamide monoethanolamine, isostearoamide diethanolamine, isostearoamide diethanolamine, isostearoamide monoethanolamine), and mixtures thereof.
[0057] Preferably, the method of conditioning hair of the present invention comprises selecting a hair conditioner formulation of the present invention and applying the hair conditioner formulation to hair (preferably mammalian hair, more preferably human hair, most preferably damaged human hair). More preferably, the method of conditioning hair of the present invention comprises selecting a hair conditioner formulation of the present invention, wetting the hair (preferably mammalian hair, more preferably human hair, most preferably damaged human hair) with water and applying the selected hair conditioner formulation to the wet hair. Most preferably, the method of conditioning hair of the present invention comprises selecting a hair conditioner formulation of the present invention, wetting the hair (preferably mammalian hair, more preferably human hair, most preferably damaged human hair), applying the selected hair conditioner formulation to the wet hair and then rinsing the hair with water.
[0058] Some embodiments of the present invention will now be described in detail in the following examples.
[0059] Synthesis S1: Synthesis of cationic conditioning polymer A 1 ounce vial was charged with dextran polymer (2 g; Sigma-Aldrich product D4876) and deionized water (7.4 g). A stir bar was added to the vial and the vial was capped. The vial was then placed on a stir plate and heated to 70° C. After the dextran was completely dissolved, 50% aqueous sodium hydroxide (0.5 g) was added to the vial contents. The vial contents were stirred continuously for 10 minutes at 70° C., after which a 40% aqueous solution of 3-chloro-2-hydroxypropyl-lauryl-dimethylammonium chloride (0.5 g; QUAB® 342 (available from SKW QUAB Chemicals) was added to the vial contents. The vial contents were then stirred for 30 minutes, after which 2-chloroethylmorpholine hydrochloride (0.9 g) was added to the vial contents. The vial contents were then stirred for 180 minutes at 70° C. Then the vial contents were cooled to room temperature. When the vial contents reached room temperature, glacial acetic acid (0.4 g) was added to the vial contents. The vial contents were then stirred for 10 minutes. The polymer products were then isolated by non-solvent precipitation in methanol and characterized by 1H NMR for structural analysis to determine the degree of substitution of the morpholino moiety, DS, as reported in Table 2. (II) and DS of the dimethyldodecylammonium moiety (III) The total Kjeldahl nitrogen, TKN, in the product conditioned polymer is also reported in Table 2.
[0060] Synthesis S2-S3: Synthesis of cationic dextran polymers In syntheses S2-S3, conditioning polymers were prepared essentially as described in synthesis S1, but with varying reagent supplies as shown in Table 1. The degree of substitution of the morpholino moiety in the product conditioning polymers, DS, as measured by NMR, was (II) and DS of QUAB® 342 part (III) is reported in Table 2. The total Kjeldahl nitrogen, TKN, in the product conditioned polymer is also reported in Table 2.
[0061] [Table 1]
[0062] [Table 2]
[0063] Comparative Examples CF1-CF4 and Examples F1-F2: Hair Conditioner Formulations Hair conditioner formulations having the formulations set forth in Table 3 were prepared in each of Comparative Examples CF1-CF4 and Examples F1-F2.
[0064] [Table 3]
[0065] Hair conditioning performance A test to evaluate the wet and dry ease of combing of hair treated with the rinse-off conditioner formulations of Comparative Examples CF1-CF4 and Example F1 was conducted as follows: Bleached Caucasian hair (8 hour bleached hair from International Hair Importers) was used to test the conditioners. Each tress weighed 2 grams. Each tress was rinsed for 30 seconds under running tap water at 40° C. A pipette was used to apply 0.4 grams of a solution containing 9 percent sodium lauryl sulfate and lathered throughout each tress for 30 seconds. The tress was then rinsed for 1 minute under running water. Excess water was removed from each tress by passing the tress between the index and middle fingers of the hand. The tresses were then treated with rinse-off conditioner formulations of Comparative Examples CF1-CF4 and Examples F1-F2 at 0.4 g of formulation / g of hair by massaging the formulation into the wet / damp hair for 1 minute. The tresses were rinsed under running water for 30 seconds and allowed to dry at room temperature overnight.
[0066] An INSTRON Model 3342 Single Column Tension running BlueHill 2 software was also used to measure conditioning performance by wet ease of combing and dry ease of combing. The test used an INSTRON strain gauge equipped 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 as measured by the INSTRON strain gauge. The force was reported as the average comb load (ACL). The lower the ACL number, the greater the conditioning benefit imparted by the rinse-off conditioner formulation tested.
[0067] According to the INSTRON wet comb method, the hair was first wetted by immersion in distilled water, then the tress was detangled by combing it three times. The tress was then re-detangled by immersing it three times in distilled water. Excess water was removed from the tress by passing it between the index and middle fingers of the hand twice. The tress was placed on a hanger and combed with an INSTRON comb. The average wet comb force of the three tresses was measured for each rinse-off conditioner formulation. The average wet comb results are listed in Table 4.
[0068] Dry hair was detangled by combing the tress three times according to the INSTRON dry comb method. The tress was then re-detangled by rotating it three times clockwise and three times counterclockwise. The tress was placed on a hanger and combed with an INSTRON comb. The average dry comb force of the three tresses was measured for each rinse-off conditioner formulation. The average dry comb results are listed in Table 4.
[0069] [Table 4]
[0070] Hair hydrophobicity Hair conditioner formulations prepared according to each of Comparative Examples CF1-CF4 and Examples F1-F2 were tested on two separate 3 g hair samples (Caucasian hair bleached for 8 hours, International Hair Importers, Inc.). The hair samples were first rinsed with water for 30 seconds. A 9% (wt / wt) aqueous solution of sodium lauryl sulfate was then massaged into the hair sample for 30 seconds. The hair samples were then rinsed with water for 60 seconds. The hair samples were then treated with a rinse-off hair conditioner in the amount of 0.4 g per gram of hair and massaged into the hair for 30 seconds. The hair samples were then rinsed with water for 30 seconds and allowed to dry before hydrophobicity testing.
[0071] To measure the hydrophobicity of hair, hair tresses were combed straight and then both ends were held tightly with a holder. Ten 30 μL water droplets were placed on each tress at different locations from root to tip and a recovery hydrophobicity score of 1 to 5 was applied for each hair conditioner formulation as reported in Table 5. A score of 1 means that the water droplet was observed to dissipate into the hair in less than 1 minute after application. A score of 2 means that the water droplet was observed to remain on the hair for at least 1 minute but less than 2 minutes after application before dissipating into the hair. A score of 3 means that the water droplet was observed to remain on the hair for at least 2 minutes but less than 5 minutes after application before dissipating into the hair. A score of 4 means that the water droplet was observed to remain on the hair for at least 5 minutes but less than 10 minutes after application before dissipating into the hair. A score of 5 means that the water droplet was observed to remain on the hair for at least 10 minutes after application before dissipating into the hair.
[0072] [Table 5]
Claims
1. 1. A hair conditioner formulation comprising: A dermatologically acceptable vehicle; a conditioning polymer, said conditioning polymer being a cationic dextran polymer comprising a dextran base polymer functionalized with morpholine groups and quaternary ammonium groups, said dextran base polymer having a weight average molecular weight of 10,000 to 3,000,000 Daltons, said morpholine groups being of formula (II) attached to pendant oxygens on said dextran base polymer; 【Chemistry 1】 The quaternary ammonium group is a quaternary ammonium group of formula (III) attached to a pendant oxygen on the dextran base polymer, 【Chemistry 2】 During the ceremony, 【Chemistry 3】 are pendant oxygens on the dextran-based polymer, A is a divalent linking group, X is a divalent linking group, and each R ２ are independently linear or branched C １～４ alkyl group, each R ３ are independently linear or branched C ８～２０ A hair conditioner formulation, wherein the alkyl group is selected from the group consisting of aryl, aryl, aryl and alkyl groups.
2. 10. The hair conditioner formulation of claim 1, wherein the hair conditioner formulation is selected from the group consisting of leave-on conditioners and rinse-off conditioners.
3. A hair conditioner formulation according to claim 2, wherein the conditioning polymer has a Kjeldahl nitrogen content, TKN, corrected for ash and volatile matter, of 0.5 to 2.5% by weight.
4. 4. The hair conditioner formulation of claim 3, wherein the hair conditioner formulation contains less than 0.01% by weight of a combination of octamethylcyclotetrasiloxane (D4), decamethylcyclopentasiloxane (D5), and dodecamethylcyclohexasiloxane (D6), based on the weight of the hair conditioner formulation.
5. 5. The hair conditioner formulation of claim 4, wherein the hair conditioner formulation contains less than 0.01% by weight of a dermatologically acceptable oil, based on the weight of the hair conditioner formulation.
6. said morpholine group of formula (II) is a morpholine group of formula (IIa) 【Chemistry 4】 said quaternary ammonium group of formula (III) is a quaternary ammonium group of formula (IIIa) 【Chemistry 5】 In the formula, each R ４ are independently hydrogen and linear or branched C １～４ 6. The hair conditioner formulation of claim 5, wherein the alkyl group is selected from the group consisting of alkyl groups.
7. In the formula, R ２ is a methyl group, R ３ Linear or branched C １２ is an alkyl group, R ４ 7. A hair conditioner formulation according to claim 6, wherein is hydrogen.
8. The degree of substitution DS of the morpholine group of formula (II) on the cationic dextran polymer （ＩＩ） is 0.01 to 0.2, and the degree of substitution DS of the quaternary ammonium group of formula (III) on the cationic dextran polymer （ＩＩＩ） 8. A hair conditioner formulation according to claim 7, wherein is greater than 0 and equal to or less than 2.
9. 9. The hair conditioner formulation of claim 8, further comprising at least one additional ingredient selected from the group consisting of antimicrobials / preservatives, rheology modifiers, soaps, colorants, pH adjusters, antioxidants, moisturizers, waxes, foaming agents, emulsifiers, colorants, fragrances, chelating agents, preservatives, bleaching agents, lubricants, sensory modifiers, sunscreen additives, vitamins, proteins / amino acids, botanical extracts, natural ingredients, bioactive agents, anti-degradation additives, pigments, acids, penetrating agents, antistatic agents, anti-frizz agents, anti-dandruff agents, hair waving / straightening agents, hair styling agents, absorbents, hard particles, soft particles, conditioning agents, slip agents, opacifying agents, pearlescent agents, and salts.
10. 1. A method of conditioning hair, comprising: Selecting a hair conditioner formulation according to claim 1; applying said hair conditioner formulation to hair.