WO2025041399A1 - Promoteur de formation de coacervat - Google Patents

Promoteur de formation de coacervat Download PDF

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Publication number
WO2025041399A1
WO2025041399A1 PCT/JP2024/019428 JP2024019428W WO2025041399A1 WO 2025041399 A1 WO2025041399 A1 WO 2025041399A1 JP 2024019428 W JP2024019428 W JP 2024019428W WO 2025041399 A1 WO2025041399 A1 WO 2025041399A1
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group
mass
meth
acrylate
polymer
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Japanese (ja)
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正弘 中之庄
悠子 鳥羽
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Nippon Shokubai Co Ltd
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Nippon Shokubai Co Ltd
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Priority to CN202480054072.6A priority Critical patent/CN121729217A/zh
Priority to JP2025541307A priority patent/JPWO2025041399A1/ja
Publication of WO2025041399A1 publication Critical patent/WO2025041399A1/fr
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    • 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
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair

Definitions

  • the present invention relates to a coacervate formation promoter. More specifically, the present invention relates to a coacervate formation promoter useful for body wash applications.
  • cationic polymers have been suitably used as antibacterial agents (for example, Patent Document 1). It is also known that cationic polymers, when combined with anionic surfactants, produce coacervates, which are complexes of the two. When shampoos and the like containing cationic polymers and anionic surfactants are diluted by rinsing or the like, coacervates are formed in a certain concentration range, which adhere to hair and can provide conditioning effects, etc.
  • Patent Document 2 discloses a hair cleansing composition having a composition of (A) 0.1-10.0% by weight of sodium succinylarginine represented by a specific formula, (B) 0.3-0.8% by weight of a specific cationic polymer (at least one of polyquaternium-10 and guar hydroxypropyltrimonium chloride), and (C) 2.0-10.0% by weight of an amphoteric surfactant.
  • Patent Document 3 discloses a cleansing agent that contains at least an anionic surfactant, an amphoteric surfactant, and a cationic polymer, and that becomes two phases at 20-40°C and appears to be separated into two layers, and that has viscoelastic properties such that at 40°C, G' (storage modulus) is greater than G'' (loss modulus), and that G' is greater than G'' when the angular velocity is in the range of 30-100 rad/s.
  • G' storage modulus
  • G'' loss modulus
  • the present invention was made in consideration of the above-mentioned current situation, and aims to provide an agent that has excellent effects in promoting coacervate formation.
  • the inventors conducted various investigations into compounds that promote the formation of coacervates, and discovered that polymers having structural units derived from amino group-containing monomers are effective in promoting the formation of coacervates with cationic polymers and anionic surfactants. They came to the conclusion that the above-mentioned problems could be solved in an excellent manner, and thus arrived at the present invention.
  • the present invention includes the following coacervate formation promoters, etc.
  • a coacervate formation promoter comprising a polymer having a structural unit (a) derived from an amino group-containing monomer (A).
  • B a hydrophobic monomer
  • a body cleansing composition comprising the coacervate formation promoter according to any one of [1] to [3] above, an anionic surfactant, and a cationic polymer.
  • a method for imparting antibacterial properties to hair and/or skin comprising the steps of applying the coacervate formation promoter according to any one of [1] to [3] above to hair and/or skin, and rinsing the hair and/or skin after the application step.
  • the coacervate formation promoter of the present invention has the above-mentioned composition and has excellent coacervate formation promoting effects, and therefore can be suitably used in body cleansing compositions, etc.
  • FIG. 1 is a graph showing the antibacterial activity against Malassezia fungi when the concentration of the composition was changed for Example 7, Comparative Example 5, and Reference Examples 3 and 4 in Antibacterial Test 2.
  • the coacervate formation promoter of the present invention contains a polymer (hereinafter also referred to as an amino group-containing polymer) having a structural unit (a) derived from an amino group-containing monomer (A). It is presumed that the amino group-containing polymer enhances the interaction between the anionic surfactant and the cationic polymer, thereby promoting the formation of a coacervate by them.
  • the amino group-containing polymer also has excellent antibacterial properties against Malassezia fungus, which is a causative bacterium of dandruff.
  • the cationic amino group of the amino group-containing polymer is adsorbed to the negatively charged cell surface of Malassezia fungus, destroying the cell membrane, thereby exerting antibacterial properties against Malassezia fungus. It is believed that the coacervate formation promoter of the present invention forms a coacervate, and the amino group-containing polymer after dissociation acts on Malassezia fungus, thereby effectively exerting antibacterial action even in a low concentration range.
  • the use of a polymer having a structural unit (a) derived from an amino group-containing monomer (A) for promoting coacervate formation is also one aspect of the present invention.
  • the present invention also relates to a method for promoting coacervate formation, which includes a step of adding a polymer having a structural unit (a) derived from an amino group-containing monomer (A) to a composition containing an anionic surfactant and a cationic polymer.
  • the content ratio of the amino group-containing polymer in the coacervate formation accelerator of the present invention is not particularly limited, but is preferably 0.001 to 100% by mass relative to 100% by mass of the coacervate formation accelerator. It is more preferably 1 to 100% by mass, even more preferably 30 to 100% by mass, and particularly preferably 50 to 100% by mass.
  • the coacervate formation accelerator of the present invention may contain other components in addition to the amino group-containing polymer.
  • the content ratio of the other components is not particularly limited, but is preferably 0 to 99.999% by mass relative to 100% by mass of the coacervate formation accelerator. It is more preferably 0 to 99% by mass, even more preferably 0 to 70% by mass, and particularly preferably 0 to 50% by mass.
  • the amino group-containing polymer has a structural unit (a) derived from an amino group-containing monomer (A).
  • the content of the structural unit (a) in the amino group-containing polymer is not particularly limited, but is preferably 1 to 99% by mass relative to 100% by mass of all structural units, which allows the coacervate formation-promoting effect to be more fully exhibited.
  • the content of the structural unit (a) is more preferably from 10 to 97% by mass, further preferably from 36 to 96% by mass, and particularly preferably from 50 to 95% by mass.
  • the content of the structural unit (a) may be 50 to 90 mass%, preferably 50 to 85 mass%, more preferably 50 to 80 mass%, even more preferably 50 to 75 mass%, and particularly preferably 50 to 70 mass%, relative to 100 mass% of all structural units.
  • the amino group-containing polymer preferably further contains a structural unit (b) derived from a hydrophobic monomer (B). This improves the balance between hydrophilicity and hydrophobicity in the amino group-containing polymer, further improving the interaction between the anionic surfactant and the cationic polymer, and further promoting the formation of a coacervate.
  • the content of the structural unit (b) in the amino group-containing polymer is not particularly limited, but is preferably 1 to 99% by mass, more preferably 3 to 90% by mass, even more preferably 4 to 70% by mass, and particularly preferably 5 to 50% by mass, based on 100% by mass of all structural units.
  • the content of the structural unit (b) may be 10 to 50 mass%, preferably 15 to 50 mass%, more preferably 20 to 50 mass%, even more preferably 25 to 50 mass%, and particularly preferably 30 to 50 mass%, relative to 100 mass% of all structural units.
  • the amino group-containing polymer may have a structural unit (c) derived from a monomer (C) other than the amino group-containing monomer (A) and the hydrophobic monomer (B).
  • the content of the structural unit (c) is preferably 0 to 10% by mass, more preferably 0 to 5% by mass, even more preferably 0 to 1% by mass, particularly preferably 0 to 0.1% by mass, and most preferably 0% by mass, based on 100% by mass of all structural units.
  • the mass ratio of the structural unit (a) derived from the amino group-containing monomer (A) to the structural unit (b) may be 99/1 to 1/99, preferably 95/5 to 40/60, more preferably 80/20 to 50/50, and particularly preferably 70/30 to 55/45.
  • the weight average molecular weight of the amino group-containing polymer is not particularly limited, but is preferably from 4,000 to 800,000. This allows the effects of the present invention to be more fully exhibited.
  • the weight average molecular weight is more preferably 6,000 to 400,000, even more preferably 7,000 to 80,000, still more preferably 8,000 to 70,000, still more preferably 10,000 to 60,000, still more preferably 15,000 to 55,000, and particularly preferably 20,000 to 50,000.
  • the weight average molecular weight of the amino group-containing polymer can be measured by the method described in the Examples.
  • amino group-containing monomer (A) Specific examples of the amino group in the amino group-containing monomer (A) include primary to tertiary amino groups, neutralized products of primary to tertiary amino groups with acids, and quaternary ammonium bases. Examples of the primary to tertiary amino groups include those represented by the following formula (1);
  • the hydrocarbon group may have a chain structure or a ring structure, but preferably has a chain structure. When the hydrocarbon group has a chain structure, it may be linear or branched.
  • the above-mentioned hydrocarbon group is preferably an alkyl group, an alkenyl group, or an aryl group, more preferably an alkyl group or an alkenyl group, and further preferably an alkyl group.
  • the hydrocarbon group preferably has 1 to 10 carbon atoms, more preferably 1 to 8 carbon atoms, particularly preferably 1 to 5 carbon atoms, and most preferably 1 or 2 carbon atoms.
  • At least one of R1 and R2 is preferably a hydrocarbon group having 1 to 12 carbon atoms, and more preferably both R1 and R2 are hydrocarbon groups having 1 to 12 carbon atoms. In other words, among the primary to tertiary amino groups, a tertiary amino group is preferred.
  • the primary to tertiary amine bases are represented by the following formula (2);
  • R 1 and R 2 are the same or different and represent a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms; Y ⁇ represents an anion.
  • Specific examples and preferred forms of the hydrocarbon group are as described above.
  • R 3 to R 5 are the same or different and each represents a hydrocarbon group having 1 to 12 carbon atoms; and Y 1 ⁇ represents an anion.
  • the hydrocarbon group having 1 to 12 carbon atoms are preferably an alkyl group having 1 to 12 carbon atoms or an alkenyl group having 2 to 12 carbon atoms.
  • the number of carbon atoms in R 3 to R 5 is more preferably 1 to 10, further preferably 1 to 7, and particularly preferably 1 to 5.
  • As the hydrocarbon group for R 3 to R 5 a methyl group or an ethyl group is most preferable.
  • Y 1 ⁇ in the above formulas (2) and (3) is not particularly limited, and examples thereof include halide ions such as chloride ion, bromide ion, and iodine ion; alkyl sulfate ions such as methyl sulfate ion; and ions of organic acids such as acetate ion.
  • Y 1 ⁇ in the above formula (2) is preferably an ion of an organic acid.
  • Y 1 ⁇ in the above formula (3) is preferably a halide ion or an alkyl sulfate ion.
  • tertiary amino groups neutralized products of primary to tertiary amino groups with acids, and quaternary ammonium bases
  • tertiary amino groups neutralized products of tertiary amino groups with acids, and quaternary ammonium bases
  • dimethylamino groups, diethylamino groups, or neutralized products of these with acids such as hydrochloric acid and acetic acid are preferred.
  • the amino group-containing monomer (A) is represented by the following formulas (4-1) to (4-3);
  • R 6 to R 8 are the same or different and represent a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • X represents a direct bond or a divalent linking group.
  • R 1 and R 2 are the same as R 1 and R 2 in formula (1) above.
  • R 3 to R 5 are the same as R 3 to R 5 in formula (3) above.
  • Y ⁇ represents an anion.
  • the alkyl group having 1 to 5 carbon atoms in the above R 8 is preferably a methyl group.
  • the above R 8 is preferably a hydrogen atom or a methyl group. From the viewpoint of antibacterial properties and hydrolysis resistance, R 8 is more preferably a methyl group.
  • the above R 6 and R 7 are preferably hydrogen atoms.
  • the divalent linking group for X in the above formulas (4-1) and (4-2) is not particularly limited, but may be, for example, an alkylene group having 1 to 12 carbon atoms or the following formula (5);
  • k represents an integer of 1 to 10.
  • m is preferably 1 to 8, and more preferably 1 to 5.
  • k is preferably 1 to 8, and more preferably 1 to 5.
  • the divalent linking group for X in the above formula (4-3) is preferably an alkylene group having 1 to 12 carbon atoms.
  • amino group-containing monomer (A) examples include N,N-dialkylamino group-containing (meth)acrylates such as N,N-dimethylaminoethyl (meth)acrylate, N,N-diethylaminoethyl (meth)acrylate, N,N-dimethylaminopropyl (meth)acrylate, and N,N-diethylaminopropyl (meth)acrylate, as well as monomers obtained by adding a quaternizing agent to the above monomers, or neutralized products of these with an acid such as hydrochloric acid or acetic acid; N,N-dimethylaminoethyl (meth)acrylamide, N,N-diethylaminoethyl (meth)acrylamide, N,N-dialkylamino group-containing (meth)acrylamides such as N,N-dimethylaminopropyl (meth)acrylamide, N,N-diethylaminopropyl (
  • the amine compound having 1 to 24 carbon atoms is not particularly limited as long as it has an amino group and can react with a cyclic ether structure of an unsaturated monomer having a cyclic ether-containing group having 2 to 8 carbon atoms.
  • the number of carbon atoms in the amine compound having 1 to 24 carbon atoms is preferably 1 to 20, and more preferably 1 to 16.
  • Examples of the amine compound having 1 to 24 carbon atoms include primary amines and secondary amines, such as (di)alkylamines having 1 to 24 carbon atoms, (di)alkanolamines having 1 to 24 carbon atoms, and alkylalkanolamines having 1 to 24 carbon atoms.
  • Preferred examples of the (di)alkylamine having 1 to 24 carbon atoms include methylamine, ethylamine, propylamine, butylamine, dimethylamine, diethylamine, dipropylamine, dibutylamine, pentylamine, dipentylamine, hexylamine, dihexylamine, heptylamine, diheptylamine, octylamine, dioctylamine, dodecylamine, and didodecylamine.
  • Preferred examples of the (di)alkanolamine having 1 to 24 carbon atoms include methanolamine, ethanolamine, propanolamine, butanolamine, dimethanolamine, diethanolamine, dipropanolamine, dibutanolamine, and hexanolamine.
  • alkylalkanolamine having 1 to 24 carbon atoms methylethanolamine and the like are preferred.
  • the amino group-containing monomer (A) is preferably one in which R 8 in the above formulas (4-1) to (4-3) is a methyl group and X is a structure represented by the above formula (5).
  • the quaternizing agent is not particularly limited, but examples thereof include common alkylating agents such as alkyl halides such as methyl chloride, ethyl chloride, methyl bromide, and methyl iodide; and alkyl sulfates such as dimethyl sulfate, diethyl sulfate, and di-n-propyl sulfate.
  • alkylating agents such as alkyl halides such as methyl chloride, ethyl chloride, methyl bromide, and methyl iodide
  • alkyl sulfates such as dimethyl sulfate, diethyl sulfate, and di-n-propyl sulfate.
  • solubility parameter of the homopolymer obtained by polymerizing the hydrophobic monomer (B) alone is 15 or less, the hydrophobicity of the copolymer of the present invention will be sufficient, the affinity for the cell membrane of the microorganism will be improved, and the interaction with the cell membrane will be increased, damaging the physiological activity of the cell membrane, resulting in superior antibacterial performance.
  • the solubility parameter is preferably 14 or less, more preferably 13 or less, and even more preferably 12 or less.
  • the solubility parameter is usually 5 or more.
  • the hydrophobic monomer (B) is not particularly limited as long as the solubility parameter of the homopolymer is 15 or less, and examples thereof include esters ((meth)acrylates) of (meth)acrylic acid and alcohols which may have a substituent; unsaturated monocarboxylic acids such as (meth)acrylic acid, crotonic acid, ⁇ -allyloxyacrylic acid, and salts thereof; aromatic vinyl monomers such as styrene; olefin monomers such as ethylene and propylene; esters of unsaturated alcohols and carboxylic acids such as vinyl acetate; vinyl halides such as vinyl chloride; methyl vinyl alkyl vinyl ethers such as ether and ethyl vinyl ether; addition reaction products of unsaturated monomers having a cyclic ether-containing group having 2 to 8 carbon atoms, such as 1-allyloxy-3-butoxypropan-2-ol, with alcohols having 1 to 20 carbon atoms; alkylene oxide adduct
  • fluoro group-containing (meth)acrylates include fluoro group-containing alkyl (meth)acrylates having an ester group with 2 to 6 carbon atoms, such as trifluoroethyl (meth)acrylate, tetrafluoropropyl (meth)acrylate, and octafluoropentyl (meth)acrylate.
  • epoxy group-containing (meth)acrylates examples include glycidyl (meth)acrylate, ⁇ -methylglycidyl (meth)acrylate, and glycidyl allyl ether.
  • carbonyl group-containing (meth)acrylates examples include acetonyl (meth)acrylate, diacetone (meth)acrylate, 2-hydroxypropyl (meth)acrylate acetylacetate, butanediol-1,4-acrylate acetylacetate, 2-(acetoacetoxy)ethyl (meth)acrylate, and (meth)acryloyloxyalkylpropenal.
  • the hydrophobic monomer (B) preferably contains at least one (meth)acrylic acid ester.
  • the (meth)acrylic acid ester may be a compound represented by the following formula (8):
  • R 9 represents a hydrogen atom or a methyl group
  • R 10 represents a hydrocarbon group having 1 to 30 carbon atoms
  • the number of carbon atoms in the hydrocarbon group is preferably 1 to 20. More preferably, it is 2 to 16, further preferably 2 to 12, and particularly preferably 2 to 8. In one embodiment, it may be 2 to 4, or may be 2. If the carbon number of the hydrocarbon group is 1 to 20, the water solubility and viscosity of the polymer can be within a suitable range, and the polymer is easy to handle. If the carbon number of the hydrocarbon group is 1 to 12, the polymer is easy to produce, and the polymer is excellent in safety in addition to antibacterial properties. Furthermore, if the carbon number of the hydrocarbon group is 2 to 8, the polymer is not only easy to produce, but also excellent in safety, and has increased affinity with bacterial cell membranes, resulting in further improved antibacterial properties.
  • the above-mentioned hydrocarbon group is not particularly limited, and examples thereof include chain-like hydrocarbon groups such as alkyl groups, alkenyl groups, and alkynyl groups, and aromatic hydrocarbon groups, and cyclic hydrocarbon groups such as cycloalkyl groups and cycloalkenyl groups.
  • the above-mentioned hydrocarbon group may have a branch, and the number of carbon atoms in the hydrocarbon group when it has a branch means the total number of carbon atoms in the main chain and the branched chains.
  • alkyl group examples include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group (amyl group), an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, an n-decyl group, an n-undecyl group, an n-dodecyl group, an n-tridecyl group, an n-tetradecyl group, an n-pentadecyl group, an n-hexadecyl group, an n-heptadecyl group, an n-octadecyl group, an n-nonadecyl group, an n-icosyl group, an i-propyl group, a sec-butyl group, an i-butyl group, i
  • aliphatic alkyl groups such as a 2-ethylbutyl group, a 2-ethyl-2-methylpropyl group, a 1-methylheptyl group, a 2-ethylhexyl group, a 1,5-dimethylhexyl group, a t-octyl group, a branched nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, a stearyl group, or an icosyl group; and alicyclic alkyl groups such as a cyclopropyl group, a cyclopropylmethyl group, a cyclobutyl group, a cyclobutylmethyl group, a cyclopentyl group,
  • alkenyl group examples include vinyl, allyl, 1-butenyl, 2-butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, dodecenyl, octadecenyl, and icosenyl groups.
  • alkynyl group examples include ethynyl, 1-propynyl, 2-propynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl, nonynyl, decynyl, dodecynyl, octadecynyl, and icosynyl groups.
  • Examples of the aromatic hydrocarbon group include a phenyl group, a benzyl group, a tolyl group, and an o-xylyl group.
  • Examples of the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.
  • Examples of the cycloalkenyl group include a cyclopropenyl group, a cyclobutenyl group, a cyclopentenyl group, and a cyclohexenyl group.
  • the above-mentioned hydrocarbon group is preferably an alkyl group or an alkenyl group, and more preferably an alkyl group. That is, the (meth)acrylic acid ester is preferably an alkyl (meth)acrylic acid ester (alkyl (meth)acrylate).
  • Preferred alkyl (meth)acrylates are methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, sec-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, and n-octyl (meth)acrylate, and more preferably methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, sec-butyl (meth)acrylate, and 2-ethylhexyl (me
  • ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, and sec-butyl (meth)acrylate are preferred, ethyl (meth)acrylate and n-butyl (meth)acrylate are more preferred, and ethyl (meth)acrylate is particularly preferred.
  • the amino group-containing polymer may have a structural unit (c) derived from another monomer (C) other than the amino group-containing monomer (A) and the hydrophobic monomer (B), and the other monomer (C) is not particularly limited as long as it can be copolymerized with the amino group-containing monomer (A) and the hydrophobic monomer (B), and for example, the solubility parameter of the other monomer in a homopolymer may be 15 or less or more than 15. Whether the solubility parameter of the other monomer is 15 or less or more than 15, as long as the hydrophobic monomer (B) is polymerized in a preferred ratio, the hydrophobicity of the copolymer is sufficiently maintained.
  • a monomer having two or more ethylenically unsaturated groups may be included regardless of the value of the solubility parameter.
  • the monomer having two or more ethylenically unsaturated groups include esters of di- or more substituted hydroxyl groups of polyols such as ethylene glycol, propylene glycol, polyoxyethylene glycol, polyoxypropylene glycol, glycerin, polyglycerin, trimethylolpropane, pentaerythritol, saccharose, sorbitol, and 1,4-butanediol with (meth)acrylic acid; di- or more substituted methacrylic acid esters of the above polyols; ethers of di- or more substituted hydroxyl groups of the above polyols with unsaturated alcohols such as allyl alcohol and vinyl alcohol; diallyl phthalate, triallyl phosphate, allyl methacrylate,
  • the amino group-containing polymer may be copolymerized with a polymerizable metal salt as another monomer, such as a heavy metal salt of an unsaturated carboxylic acid, such as zinc acrylate, zinc methacrylate, or zinc ⁇ -allyloxyacrylate.
  • a polymerizable metal salt such as a heavy metal salt of an unsaturated carboxylic acid, such as zinc acrylate, zinc methacrylate, or zinc ⁇ -allyloxyacrylate.
  • the present invention also relates to a body wash composition comprising the coacervate formation promoter of the present invention, an anionic surfactant, and a cationic polymer.
  • the present invention also relates to use of a composition comprising a polymer having structural units (a) derived from the amino group-containing monomer (A), an anionic surfactant, and a cationic polymer for body washing.
  • the coacervate formation between the anionic surfactant and the cationic polymer is promoted by the coacervate formation promoter.
  • the amino group-containing polymer is incorporated into the coacervate.
  • the coacervate is formed as described above when the hair and/or skin is rinsed.
  • the body wash composition is further diluted with water, the coacervate is destroyed.
  • the amino group-containing polymer in the coacervate is released, so that the antibacterial effect of the amino group-containing polymer can be effectively exerted even when the body wash composition is diluted.
  • the body cleansing composition can be suitably used for various applications.
  • Specific examples include hair cleansing compositions such as shampoos, rinses, and hair treatments; skin cleansing compositions such as face wash foams, liquid soaps, hand soaps, body soaps, liquid cleansers for babies, pet shampoos, cleansing creams, cleansing milks, cleansing lotions, bath additives for bubble baths, massage creams, and body shampoos.
  • Hair cleansing compositions are preferred.
  • the proportion of the coacervate formation promoter in the body cleansing composition is not particularly limited, but is preferably 0.01 to 10% by mass, more preferably 0.05 to 8% by mass, even more preferably 0.1 to 6% by mass, and particularly preferably 0.5 to 5% by mass, relative to 100% by mass of the body cleansing composition.
  • the proportion of the amino group-containing polymer in the body cleansing composition is preferably 0.01 to 10% by mass, more preferably 0.05 to 8% by mass, even more preferably 0.1 to 6% by mass, and particularly preferably 0.5 to 5% by mass, based on 100% by mass of the body cleansing composition.
  • the proportion of the anionic surfactant in the body cleansing composition is not particularly limited, but is preferably 1 to 50% by mass, more preferably 2 to 40% by mass, even more preferably 3 to 30% by mass, and particularly preferably 5 to 25% by mass, based on 100% by mass of the body cleansing composition.
  • the ratio of the anionic surfactant is preferably 20 to 500,000% by mass relative to 100% by mass of the amino group-containing polymer. More preferably, it is 100 to 250,000% by mass, even more preferably, it is 1,000 to 100,000% by mass, and particularly preferably, it is 10,000 to 50,000% by mass.
  • the ratio of the anionic surfactant may be 200 to 10,000% by mass relative to 100% by mass of the amino group-containing polymer, preferably, it is 500 to 5,000% by mass, more preferably, it is 700 to 3,000% by mass, and even more preferably, it is 800 to 2,000% by mass.
  • the proportion of the cationic polymer in the body cleansing composition is not particularly limited, but is preferably 0.01 to 3 mass %, more preferably 0.02 to 2.5 mass %, even more preferably 0.05 to 2 mass %, and particularly preferably 0.1 to 1.5 mass %, relative to 100 mass % of the body cleansing composition.
  • the proportion of the cationic polymer is preferably 10 to 5000% by mass relative to 100% by mass of the amino group-containing polymer. More preferably, it is 10 to 4000% by mass, even more preferably, it is 10 to 3000% by mass, and particularly preferably, it is 10 to 2000% by mass.
  • the proportion of the cationic polymer may be 10 to 1000% by mass relative to 100% by mass of the amino group-containing polymer, preferably, it is 20 to 800% by mass, more preferably, it is 30 to 600% by mass, even more preferably, it is 40 to 500% by mass, even more preferably, it is 50 to 300% by mass, and particularly preferably, it is 50 to 250% by mass.
  • the embodiment in which the cationic polymer is hydroxyethyl cellulose hydroxypropyl trimethyl ammonium chloride ether (cationized cellulose, PQ-10) is one of the preferred embodiments of the present invention, and when the cationic polymer is PQ-10, the content ratio thereof is preferably 0.01 to 3 mass% relative to 100 mass% of the body cleansing composition, more preferably 0.02 to 2.5 mass%, even more preferably 0.05 to 2 mass%, and particularly preferably 0.05 to 1.5 mass%.
  • the content of PQ-10 is preferably 10 to 1000% by mass, more preferably 20 to 800% by mass, even more preferably 30 to 600% by mass, particularly preferably 40 to 500% by mass, even more preferably 50 to 300% by mass, still more preferably 50 to 250% by mass, and particularly preferably 55 to 200% by mass, based on 100% by mass of the amino group-containing polymer.
  • the cationic polymer is O-[2-hydroxy-3-(trimethylammonio)propyl]guar gum chloride (cationized guar) is also one of the preferred embodiments of the present invention, and when the cationic polymer is cationized guar, the content ratio thereof is preferably 0.01 to 3 mass% relative to 100 mass% of the body cleansing composition, more preferably 0.02 to 2.5 mass%, even more preferably 0.05 to 2 mass%, and particularly preferably 0.1 to 1.5 mass%.
  • the content of the cationized guar is preferably 10 to 5000% by mass, more preferably 20 to 4000% by mass, even more preferably 30 to 3000% by mass, still more preferably 40 to 2000% by mass, still more preferably 50 to 1000% by mass, still more preferably 60 to 500% by mass, and particularly preferably 70 to 300% by mass, based on 100% by mass of the amino group-containing polymer.
  • the body cleansing composition may contain other ingredients in addition to the coacervate formation promoter, the anionic surfactant, and the cationic polymer.
  • the content ratio of the other components is not particularly limited, but is preferably 0 to 95% by mass, more preferably 10 to 95% by mass, even more preferably 20 to 95% by mass, and particularly preferably 30 to 95% by mass, relative to 100% by mass of the body cleansing composition.
  • the anionic surfactant is not particularly limited, but examples thereof include higher fatty acids such as lauric acid and stearic acid, fatty acid soaps such as sodium palmitate and sodium laureth-4 carboxylate, higher alkyl sulfates such as sodium lauryl sulfate, alkyl ether sulfates such as POE triethanolamine lauryl sulfate, N-acyl sarcosinates such as sodium lauroyl sarcosine, higher fatty acid amide sulfonates such as sodium coconut oil fatty acid methyl taurate, phosphates such as POE stearyl ether phosphoric acid, sulfosuccinates such as sodium di-2-ethylhexyl sulfosuccinate, N-acyl glutamates such as monosodium N-lauroyl glutamate, and higher fatty acid ester sulfates such as sodium hydrogenated coconut oil fatty acid
  • fatty acid soaps such as sodium laureth-4 carboxylate, higher alkyl sulfates such as sodium lauryl sulfate, and higher fatty acid amide sulfonates such as sodium coconut oil fatty acid methyl taurate are preferred.
  • the cationic polymer is not particularly limited as long as it has a cationic group and is a polymer other than the amino group-containing polymer.
  • Examples of the cationic polymer include dimethyldiallylammonium chloride polymers such as polydimethylmethylenepiperidinium chloride (Polyquaternium-6); dimethyldiallylammonium chloride-acrylamide copolymers (Polyquaternium-7), dimethyldiallylammonium chloride-acrylic acid copolymers (Polyquaternium-22), acrylic acid amide-acrylic acid-dimethyldiallylammonium chloride copolymers (Polyquaternium-39), and vinylpyrrolidone-methacrylamide chloride.
  • dimethyldiallylammonium chloride polymers such as polydimethylmethylenepiperidinium chloride (Polyquaternium-6); dimethyldiallylammonium chloride-acrylamide copolymers (Polyquaternium-7), dimethyldiallylammonium chloride-acryl
  • Acrylic cationic copolymers such as propyltrimethylammonium copolymer (Polyquaternium-28), quaternary ammonium salt obtained from vinylpyrrolidone-dimethylaminoethyl methacrylate copolymer and diethyl sulfate (Polyquaternium-11), vinylpyrrolidone-dimethylaminopropyl methacrylate amide-methacrylic acid amide propyl lauryl dimethylammonium chloride copolymer (Polyquaternium-55); methylvinylimidazolinium chloride-vinylpyrrolidone copolymer (Polyquaternium-16), vinylpyrrolidone-3-methyl-1-vinylimidazolium methylsulfate cationic copolymers containing vinylpyrrolidone and vinylimidazolium as monomer units, such as vinylcaprolactam-vinylpyrrolidone-methylvinylimidazolium methyls
  • cationic cellulose such as polyquaternium-10 and polyquaternium-67
  • cationic guar gum such as O-[2-hydroxy-3-(trimethylammonio)propyl]guar gum chloride
  • polyquaternium-10 and O-[2-hydroxy-3-(trimethylammonio)propyl]guar gum chloride are preferred.
  • the weight average molecular weight of the cationic polymer is not particularly limited, but is preferably from 100,000 to 2,500,000, more preferably from 150,000 to 2,000,000, further preferably from 500,000 to 2,000,000, and particularly preferably from 600,000 to 2,000,000.
  • the weight average molecular weight of the cationic polymer can be measured by the method described in the Examples.
  • the cationic polymer preferably has a nitrogen element content of 0.2 to 3 mass %, more preferably 0.4 to 2.5 mass %, further preferably 0.4 to 2.0 mass %, and particularly preferably 0.5 to 2.0 mass %, based on 100 mass % of the cationic polymer.
  • the nitrogen element content of the above cationic polymer can be easily calculated if the chemical structure is clear, but even if the chemical structure such as the monomer ratio is unknown, it can be calculated from the measured nitrogen content by the Kjeldahl method or the like.
  • the proportion of cationic cellulose in the body cleansing composition is preferably 10 to 5000% by mass, more preferably 10 to 4000% by mass, even more preferably 10 to 3000% by mass, still more preferably 20 to 2000% by mass, still more preferably 30 to 1000% by mass, still more preferably 40 to 500% by mass, and particularly preferably 50 to 300% by mass, relative to 100% by mass of the amino group-containing polymer.
  • the proportion of cationic guar gum in the body cleansing composition is preferably 10 to 1000% by mass, more preferably 10 to 800% by mass, even more preferably 20 to 600% by mass, still more preferably 30 to 500% by mass, still more preferably 40 to 300% by mass, and particularly preferably 40 to 250% by mass, based on 100% by mass of the amino group-containing polymer.
  • amphoteric surfactants include imidazoline-based amphoteric surfactants such as 2-cocoyl-2-imidazolinium hydroxide-1-carboxyethyloxy disodium salt, and betaine-based surfactants such as 2-heptadecyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine, lauryl dimethylaminoacetic acid betaine, alkyl betaine, amido betaine, and sulfobetaine.
  • imidazoline-based amphoteric surfactants such as 2-cocoyl-2-imidazolinium hydroxide-1-carboxyethyloxy disodium salt
  • betaine-based surfactants such as 2-heptadecyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine, lauryl dimethylaminoacetic acid betaine, alkyl betaine, amido betaine, and sulfobetaine.
  • esters include esters, POE fatty acid esters such as POE monooleate, POE alkyl ethers such as POE 2-octyldodecyl ether, Pluronic (registered trademark) types such as Pluronic (registered trademark), POE-POP alkyl ethers such as POE-POP cetyl ether, tetraPOE-tetraPOP ethylenediamine condensates such as Tetronic, POE castor oil derivatives such as POE castor oil, POE hydrogenated castor oil, POE hydrogenated castor oil derivatives such as POE hydrogenated castor oil monoisostearate, sucrose fatty acid esters, alkyl glucosides, etc.
  • esters such as POE monooleate
  • POE alkyl ethers such as POE 2-octyldodecyl ether
  • Pluronic (registered trademark) types such as Pluronic (registered trademark)
  • the transmittance (%) of the compositions of the Examples, Reference Examples, and Comparative Examples, and solutions obtained by diluting these compositions with tap water 2-fold, 4-fold, 8-fold, 10-fold, 16-fold, 50-fold, and 100-fold, at 25° C. and 600 nm was measured using an ultraviolet-visible spectrophotometer (Ultrospec 3100 pro (manufactured by Biochrom)).
  • the turbidity (%) was calculated from the transmittance using the following formula and evaluated as the amount of coacervate produced.
  • pH Measurement Conditions The pH was measured at 25° C. using a pH meter (HORIBA, Ltd.; model LAQUA pH/ION METER F-72).
  • Viscosity measurement conditions The initial viscosity (unit: mPa ⁇ s) was measured using a Brookfield viscometer (model BMII, manufactured by Toki Sangyo Co., Ltd.) under the conditions of rotor: No. 3, rotation speed: 6 rpm, measurement time: 60 seconds, and temperature: 25° C.
  • a monomer solution 1 consisting of 65.0 g of 2-(dimethylamino)ethyl methacrylate (N,N-dimethylaminoethyl methacrylate) (manufactured by Kyoeisha Chemical Co., Ltd., hereinafter referred to as DAM), a monomer solution 2 consisting of 35.0 g of ethyl methacrylate (manufactured by Kyoeisha Chemical Co., Ltd., hereinafter referred to as EMA), and an initiator aqueous solution consisting of 18.3 g of a 10% aqueous solution of 2,2′-azobis(2-methylpropionamidine) dihydrochloride (manufactured by Fujifilm Wako Pure Chemical Co., Ltd., hereinafter referred to as V-50) were each dropped from separate dropping nozzles.
  • DAM 2-(dimethylamino)ethyl methacrylate
  • EMA monomer solution 2 consisting of 35.0 g of
  • the monomer solutions 1 and 2 and the aqueous initiator solution were dropped at the same time, and the monomer solution 1 was dropped for 180 minutes, the monomer solution 2 for 170 minutes, and the aqueous initiator solution for 210 minutes.
  • the reaction solution was kept at 80°C for another 30 minutes to mature and complete the polymerization, and then 209.6 g of pure water and 522.0 g of 1,3-butanediol were added to obtain copolymer 1.
  • the solid content of the obtained copolymer was 10.0%, pH was 9.0, and weight average molecular weight was 34,000.
  • ⁇ Shampoo Formulation 1 Examples 1-2, Comparative Example 1>
  • a composition was prepared according to the following shampoo formulation 1 so as to have the composition shown in Table 1 below.
  • A. After components 1 to 4 are uniformly dissolved, component 5 is added and mixed uniformly. (80°C, 10 minutes, paddle: 300 rpm)
  • B. Add component 6 to A and dissolve uniformly (80°C, 5 minutes, paddle: 200 rpm).
  • D. Add ingredients 7 to 9, which have already been uniformly mixed, to C and mix uniformly.
  • E. Add ingredients 10, 11, and 12 in order to D and mix uniformly.
  • pH measurement, viscosity measurement, and evaluation of promotion of coacervate formation were carried out.
  • ⁇ Shampoo Formulation 2 Examples 3 to 5, Comparative Examples 2 to 3>
  • a composition was prepared according to the following shampoo formulation 2 so as to have the composition shown in Table 2 below.
  • A. After components 1 to 3 are uniformly dissolved, component 4 is added and mixed uniformly. (80°C, 10 minutes, paddle: 300 rpm) B. Cool A to 40°C. C. Add component 5 to B and mix uniformly. D. Add ingredients 6 and 7 to C in order and mix uniformly.
  • the composition obtained by shampoo formulation 2 was subjected to pH measurement, viscosity measurement, and evaluation of the promotion of coacervate formation. The viscosity measurement was performed as described above, except that the rotor was changed to No. 4 and the rotation speed was changed to 12 rpm.
  • Example 6, Reference Example 1, Comparative Example 4> A composition was prepared according to the following shampoo formulation 3 so as to have the composition shown in Table 3 below.
  • A. Add component 2 to component 1 and mix uniformly (80°C, 10 minutes, paddle: 300 rpm)
  • B. Add components 3, 4, and 5 to A in that order and dissolve uniformly (80°C, 5 minutes, paddle: 200 rpm).
  • C. Add ingredients 6, 7, 8, and 9 to B in that order, dissolve uniformly, and then cool to 60°C.
  • D. Add ingredients 10 and 11 to C in order, dissolve uniformly, and then cool to 50°C.
  • E. Add ingredients 12 and 13 to D in that order, dissolve uniformly, and then cool to room temperature.
  • the composition obtained according to shampoo formulation 3 was subjected to pH measurement, viscosity measurement, and evaluation of promotion of coacervate formation. The viscosity measurement was performed as described above, except that the rotation speed was changed to 12 rpm.
  • Shampoo formulation 4 Example 7, Reference Example 2, Comparative Example 5
  • a composition was prepared according to the following shampoo formulation 4 so as to have the composition shown in Table 4 below.
  • A. Add components 2 and 3 to component 1 and mix uniformly (80°C, 10 minutes, paddle: 300 rpm).
  • B. Add ingredients 4, 5, and 6 to A in that order and dissolve uniformly (80°C, 5 minutes, paddle: 200 rpm).
  • C. Add ingredients 7, 8, and 9 to B in that order, dissolve uniformly, and then cool to 60°C.
  • D. Add ingredients 10 and 11 to C in order, dissolve uniformly, and then cool to 50°C.
  • E. Add ingredients 12 and 13 to D in that order, dissolve uniformly, and then cool to room temperature.
  • the composition obtained according to shampoo formulation 4 was subjected to pH measurement, viscosity measurement, and evaluation of promotion of coacervate formation. The viscosity measurement was performed as described above, except that the rotation speed was changed to 12 rpm.
  • the commercially available shampoo A (hereinafter also referred to as commercially available product A) (Reference Example 3) containing zinc pyrithione as an active ingredient
  • the commercially available shampoo B (hereinafter also referred to as commercially available product B) (Reference Example 4) containing piroctone olamine as an active ingredient
  • the shampoo formulation of Example 6 was also carried out at the same time.
  • the dish was left to stand for 4 days at 25°C, and the range in which colony growth could not be confirmed was confirmed.
  • the criteria for judgment are as follows: +++: Completely inhibited proliferation. ++: Bacterial growth was observed in a very small area. +: Bacterial growth was observed over a relatively wide area. -: No inhibitory effect on bacteria. The results are shown in Table 5.
  • Example 7 Comparative Example 5, Reference Examples 3 and 4>
  • the perforations were filled with the shampoo compositions of Example 7 and Comparative Example 5, commercial product A (Reference Example 3), and commercial product B (Reference Example 4), and the dilution ratios when filling were changed to 10, 16, 25, and 50 times, respectively, and the same procedure as in antibacterial test 1 was repeated, and the effect against Malassezia fungus was confirmed based on the diameter of the inhibition zone.
  • the results are shown in Table 6.
  • Example 7 which contained Copolymer 1. It was suggested that Copolymer 1 was released with the formation and destruction of coacervates, and that it may act efficiently on Malassezia fungi even in the low concentration range.

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Abstract

Le but de la présente invention est de fournir un agent présentant un effet exceptionnel pour favoriser la formation de coacervat. La présente invention concerne un promoteur de formation de coacervat contenant un polymère comportant un motif structural (a) dérivé d'un monomère contenant un groupe amino (A).
PCT/JP2024/019428 2023-08-18 2024-05-27 Promoteur de formation de coacervat Pending WO2025041399A1 (fr)

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007284459A (ja) * 1999-06-25 2007-11-01 Procter & Gamble Co 局所用抗菌組成物
JP2014528456A (ja) * 2011-10-07 2014-10-27 ザ プロクター アンド ギャンブルカンパニー 毛髪感触の改善を達成する方法
US20150306014A1 (en) * 2013-10-09 2015-10-29 The Procter & Gamble Company Personal Cleansing Compositions and Methods
JP2016210775A (ja) * 2010-08-31 2016-12-15 大塚製薬株式会社 頭皮頭髪洗浄用組成物
JP2018172338A (ja) * 2017-03-31 2018-11-08 株式会社コーセー シャンプー組成物
JP2022076796A (ja) * 2020-11-10 2022-05-20 株式会社日本触媒 常在菌抗菌剤
JP2023088829A (ja) * 2021-12-15 2023-06-27 株式会社日本触媒 身体用洗浄剤組成物

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007284459A (ja) * 1999-06-25 2007-11-01 Procter & Gamble Co 局所用抗菌組成物
JP2016210775A (ja) * 2010-08-31 2016-12-15 大塚製薬株式会社 頭皮頭髪洗浄用組成物
JP2014528456A (ja) * 2011-10-07 2014-10-27 ザ プロクター アンド ギャンブルカンパニー 毛髪感触の改善を達成する方法
US20150306014A1 (en) * 2013-10-09 2015-10-29 The Procter & Gamble Company Personal Cleansing Compositions and Methods
JP2018172338A (ja) * 2017-03-31 2018-11-08 株式会社コーセー シャンプー組成物
JP2022076796A (ja) * 2020-11-10 2022-05-20 株式会社日本触媒 常在菌抗菌剤
JP2023088829A (ja) * 2021-12-15 2023-06-27 株式会社日本触媒 身体用洗浄剤組成物

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