WO2018093210A2 - Composition cosmétique comprenant du 2,3-butanediol - Google Patents

Composition cosmétique comprenant du 2,3-butanediol Download PDF

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Publication number
WO2018093210A2
WO2018093210A2 PCT/KR2017/013141 KR2017013141W WO2018093210A2 WO 2018093210 A2 WO2018093210 A2 WO 2018093210A2 KR 2017013141 W KR2017013141 W KR 2017013141W WO 2018093210 A2 WO2018093210 A2 WO 2018093210A2
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WO
WIPO (PCT)
Prior art keywords
butanediol
cosmetic composition
agent
antioxidant
group
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/KR2017/013141
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English (en)
Korean (ko)
Other versions
WO2018093210A3 (fr
Inventor
안재범
송효학
박종명
전상준
신우균
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
GS Caltex Corp
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GS Caltex Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by GS Caltex Corp filed Critical GS Caltex Corp
Publication of WO2018093210A2 publication Critical patent/WO2018093210A2/fr
Publication of WO2018093210A3 publication Critical patent/WO2018093210A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • 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

Definitions

  • the present invention relates to a cosmetic composition comprising 2,3-butanediol.
  • 2,3-butanediol can be produced industrially through a continuous chemical catalysis process using, for example, C-4 olefins, and can be used as an industrial preparation for fuel additives, antifreezes, plasticizers, and the like. Can be.
  • 2,3-butanediol has been limited in its use due to problems such as expensive manufacturing processes, causing environmental pollution, and difficulty in separating isomers.
  • Korean Patent Laid-Open No. 2012-0017504 discloses the use of 2,3-butanediol in ink toners.
  • One object of the present invention is to provide a cosmetic composition comprising 2,3-butanediol as various functional components and auxiliary components.
  • 2,3-butanediol comprises at least one of 2R, 3S-butanediol and 2R, 3R-butanediol, cosmetic composition.
  • 2R, 3S-butanediol is an antibacterial, antiseptic, moisturizing agent, detergent, wetting agent, stabilizer, softener, viscosity regulator, pH regulator, surfactant, antioxidant, dispersant, antioxidant, anti-wrinkle agent, anti-inflammatory agent and Cosmetic composition for use as at least one single component selected from the group consisting of carriers.
  • 2R, 3R-butanediol is antibacterial, antiseptic, moisturizer, detergent, wetting agent, stabilizer, emollient, viscosity regulator, pH regulator, surfactant, antioxidant, dispersant, antioxidant, anti-wrinkle agent, anti-inflammatory agent and Cosmetic composition for use as at least one single component selected from the group consisting of carriers.
  • the cosmetic composition according to the above 1, having a formulation selected from the group consisting of creams, lotions, oils, pastes, powders, essences, lotions, packs, gels, sprays, ointments and emulsions.
  • 2,3-butanediol is used as one component of the alcohol mixture, cosmetic composition.
  • the alcohol mixture further comprises at least one selected from the group consisting of 1,3-propanediol, 1,3-butanediol, hexanediol and pentanediol, cosmetic composition.
  • 2,3-butanediol includes 2R, 3S-butanediol, 2R, 3R-butanediol and 2S, 3S-butanediol, and 2R, 3S-butanediol in the total weight of 2,3-butanediol is 90 Cosmetic composition, which is at least% by weight.
  • 2,3-butanediol is derived from cassava (cassava) raw material and Klebsiella strains, cosmetic composition.
  • 2,3-butanediol including at least one of 2R, 3S-butanediol and 2R, 3R-butanediol may be utilized as various formulations of the cosmetic composition.
  • 2,3-butanediol has excellent antimicrobial, antiseptic, skin affinity, detergency and wetting ability compared to other diols and triols, and therefore, antibacterial, antiseptic, moisturizing, cleaning, wetting agents, swelling agents, It can be effectively used as a stabilizer, softener, viscosity regulator, pH regulator, surfactant, antioxidant, dispersant, carrier and the like.
  • a cosmetic composition comprising 2,3-butanediol is provided.
  • 2,3-butanediol is stereochemically classified into three isomers and specifically includes (2R, 3R), (2S, 3S), (2R, 3S) stereoisomers.
  • At least one of 2R, 3S-butanediol and 2R, 3R-butanediol of the stereoisomers may be used as various components of the cosmetic composition.
  • at least one of 2R, 3S-butanediol and 2R, 3R-butanediol may be used as an antimicrobial agent, preservative, moisturizer, detergent, wetting agent, swelling agent, stabilizer, softener, viscosity modifier, pH adjuster, surfactant, oxidizing agent in cosmetic compositions. It can be used as an inhibitor, dispersant, antioxidant, anti-wrinkle agent, anti-inflammatory.
  • at least one of 2R, 3S-butanediol and 2R, 3R-butanediol may be used as the solvent of the cosmetic composition.
  • embodiments of the present invention do not exclude the use of 2S, 3S-butanediol, and 2S, 3S-butanediol may also be used alone or in combination with each other, or with at least one of 2R, 3S-butanediol and 2R, 3R-butanediol. Can be used in combination.
  • 2,3-butanediol synthesized on a bio basis may be used.
  • the fermentation broth may be prepared, and the fermentation broth may be purified through separation methods such as filtration, concentration, distillation, adsorption, chromatography, ion exchange, and electrodialysis to produce 2,3-butanediol.
  • the fermentation broth may be obtained by fermenting the raw material with a strain.
  • the raw material may be a starch-based material, in one embodiment, cassava (cassava), Raw-sugar, glucose may be used.
  • microorganisms having a fermentation product production capacity can be utilized without particular limitation.
  • Klebsiella, yeast, E. coli, Bacillus and the like may be utilized as the microorganism.
  • Klebsiella may be used as the microorganism, and more specifically, Klebsiella oxytoca may be used.
  • starch-based substances such as cassava can be glycosylated and then fermented using the strain.
  • the fermentation product can then be filtered (eg microfiltration and / or ultrafiltration) and then concentrated through distillation.
  • the concentrated product can be converted to an alcohol product containing high concentrations of 2R, 3S-butanediol through purification processes such as ion exchange, electrodialysis, solvent extraction, binary extraction and the like.
  • a process using cassava and Klebsiella oxytoca may be used to obtain an alcohol product in which 2R, 3S-butanediol dominates.
  • 2R, 3S-butanediol dominates.
  • at least 90% by weight of 2R, 3S-butanediol may be included in the total weight of the total alcohol product.
  • 2,3-butanediol may be suitably formulated and used according to the formulation and use of the cosmetic composition as the functional agent described above, for example, about 0.5 to 25% by weight, preferably about 1 to 15, of the total weight of the cosmetic composition. Weight percent, more preferably about 1 to 10 weight percent, even more preferably about 1 to 5 weight percent.
  • the type of the cosmetic composition is not particularly limited and may be formulated in the form of, for example, creams, lotions, oils, pastes, powders, essences, lotions, packs, gels, sprays, ointments, emulsions, and the like.
  • the cosmetic composition may be prepared in a variety of products such as cleansers, body wash, lipstick, hair cosmetics (for example, shampoo, rinse, essence, etc.), hand cream, foundation.
  • the cosmetic composition may comprise a base material suitable for the formation of the formulation.
  • the formulation of the cosmetic composition is a paste, cream or gel, animal fibers, plant fibers, waxes, paraffins, starches, tracantes, cellulose derivatives, polyethylene glycol, silicone, bentonite, silica, talc or zinc oxide are used as base materials.
  • animal fibers animal fibers
  • plant fibers waxes, paraffins, starches, tracantes, cellulose derivatives
  • polyethylene glycol silicone, bentonite, silica, talc or zinc oxide
  • the formulation of the cosmetic composition is a powder or a spray
  • lactose, talc, silica, aluminum hydroxide, calcium silicate or polyamide powder may be used, and in the case of a spray, additionally chlorofluorohydrocarbon, propane Propellant such as butane or dimethyl ether.
  • the base material is water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1,3-butylglycol oil, glycerol Aliphatic esters, polyethylene glycols or fatty acid esters of sorbitan can be used.
  • 2,3-butanediol may be utilized as a carrier component (base material), for example a solvent, of the cosmetic composition in solution form.
  • base material for example a solvent
  • the cosmetic composition may include other active ingredients in addition to 2,3-butanediol, and the active ingredient may be appropriately modified or adjusted according to the use, purpose, and formulation of the cosmetic composition.
  • 2R, 3S-butanediol and 2R, 3R-butanediol were commonly used biobased products obtained through fermentation products using cassava and Klebsiella oxytoca.
  • a cosmetic composition comprising 2,3-butanediol as an antimicrobial agent.
  • antibacterial as used in the present application means resistance to bacteria, fungi, and the like, and includes resistance to reproduction or reproduction against contaminating microorganisms such as bacteria and fungi.
  • microorganisms including Pseudomonas aeruginose, Escherichia coli, Staphylococcus aureus, Candida albicans, and Aspergillus niger were cultured in a medium containing various diols. After incubation for 48 hours, the antimicrobial activity was evaluated by measuring the Minimum Inhibitory Concentration (MIC) for each diol. The evaluation results are shown in Table 1 below.
  • 2,3-butanediol showed overall good antimicrobial activity compared to 1,3-butanediol and 1,3-propanediol, and 2R, 3S-butanediol showed the best antibacterial activity.
  • a cosmetic composition comprising 2,3-butanediol as a preservative.
  • the term “preservation” refers to the ability to prevent the decay of the product, as well as contaminating microorganisms, as well as the ability to suppress natural decay by exposure to the external environment.
  • 2,3-butanediol showed good overall antiseptic ability compared to 1,3-butanediol and 1,3-propanediol, and 2R, 3S-butanediol was substantially deteriorated after 8 weeks. No denaturation was observed.
  • a cosmetic composition comprising 2,3-butanediol as an agent for improving skin affinity of the cosmetic composition.
  • 2,3-butanediol may be used as an emollient, humectant, or humectant of the cosmetic composition.
  • a cosmetic composition comprising 2,3-butanediol as a cleaning agent.
  • 2,3-butanediol may be included in soaps, body washes, cleansers, and the like, thereby enhancing cleaning performance of waste products such as oil and makeup.
  • 2,3-butanediol may function not only as a direct cleaner, but also as a cleaning aid (eg, humectant, swelling agent) for promoting cleaning action.
  • a cleaning aid eg, humectant, swelling agent
  • a detergent composition was prepared by changing the type of diol while keeping the remaining components the same.
  • the remaining components included diethylene glycol (30% by weight), coconut oil ester (30% by weight) and the diol was added at 20% by weight.
  • the balance of the composition included purified water.
  • Evaluation criteria are as follows.
  • a cosmetic composition comprising 2,3-butanediol as an anti-wrinkle agent.
  • wrinkle improvement refers to a property of inhibiting the formation of wrinkles by reducing collagenase (for example, MMP-1) of the skin to inhibit degradation of interstitial collagen and the like. can do.
  • Example 1 2R, 3S-butanediol 0.05
  • Example 2 0.10
  • Example 3 0.50
  • Example 4 1.00
  • Example 5 2R, 3R-butanediol 0.05
  • Example 6 0.10
  • Example 7 0.50
  • Example 8 1.00 Comparative Example 1 1,3-butanediol 0.50 Comparative Example 2 1,3-propanediol 0.50
  • the cells CCD-986SK (ACTT CRL-6323 TM ) was dispensed in 5 x 10 4 by 1mL in a well plate and incubated for 24 hours in 37 °C, 5% CO 2 incubator.
  • the cultured cells were replaced with the medium of the Examples and Comparative Examples and incubated for 48 hours in 37 °C, 5%, CO2 incubator.
  • the cell lysate was collected and the protein content was measured using a BSA protein assay reagent kit (Thermo scientific PIERCE, USA). Table 6 shows.
  • a cosmetic composition comprising 2,3-butanediol as an antioxidant.
  • the free radical scavenging activity was measured using DPPH (2,2-diphenyl-1-picrylhydrazyl) assay. Specifically, the antioxidant rate was calculated by Equation 2 below.
  • Antioxidant rate (%) (sample absorbance-sample untreated group absorbance) / (negative control absorbance-sample untreated group absorbance) X 100
  • Sample treatment group group in which sample and DPPH reacted at each concentration
  • a cosmetic composition comprising 2,3-butanediol as an anti-inflammatory agent.
  • the anti-inflammatory effect was determined by the inhibition rate of NO (Nitiric oxide) production when LPS (Lipopolysaccharide, NO production inducer) to RAW 264.7 cells.
  • the NO production inhibition rate was measured using the Griess reagent assay. Specifically, the NO production inhibition rate was measured by Equation 3 below.
  • sample treatment group group treated with LPS and sample for each concentration diluted with culture solution
  • RAW 264.7 cell culture samples containing 1% by weight of 2R, 3S-butanediol and 2R, 3R-butanediol were prepared, and the absorbance was measured by treating LPS with each sample, and the calculated NO production inhibition rates are shown in Table 8 below. .
  • 2,3-butanediol may be utilized as a stabilizer or dispersant of the cosmetic composition.
  • the cosmetic composition includes pigment particles, functional inorganic particles, or various natural particles
  • 2,3-butanediol may be utilized as an agent for improving dispersibility and solubility of the particles.
  • 2,3-butanediol may be utilized as a surfactant of the cosmetic composition.
  • 2,3-butanediol may be used alone or in combination with other known surfactant components.
  • Known surfactants may include nonionic surfactants, anionic surfactants, cationic surfactants, amphoteric surfactants, and the like.
  • nonionic surfactant examples include self-emulsifying monoglycerate, propylene glycol fatty acid ester, glycerin fatty acid ester, polyglycerol fatty acid ester, sorbitan fatty acid ester, POE (polyoxyethylene) sorbitan fatty acid ester, POE sorbitan fatty acid ester, POE glycerin fatty acid ester, POE alkyl ether, POE fatty acid ester, POE hardened castor oil, POE castor oil, POEPOP (polyoxyethylene polyoxypropylene) copolymer, POEPOP alkyl ether, polyether modified silicone, laurin Acid alkanolamide, alkylamine oxide, hydrogenated soybean phospholipid, etc. are mentioned.
  • anionic surfactant fatty acid soap, (alpha)-acyl sulfonate, alkyl sulfonate, alkyl allyl sulfonate, alkyl naphthalene sulfonate, alkyl sulfate, POE alkyl ether sulfate, alkylamide sulfate, alkyl phosphate, POE alkyl phosphorus salt, alkylamide Phosphates, alkyloylalkyltaurine salts, N-acylamino acid salts, POE alkyl ether carboxylate salts, alkyl sulfosuccinate salts, sodium alkyl sulfo acetates, acylated hydrolyzed collagen peptide salts, perfluoroalkyl phosphate esters, and the like. have.
  • amphoteric surfactants include the carboxybetaine type, the amide betain type, the sulfobetain type, the hydroxysulfobetain type, the amide sulfobetain type, the phosphobetaine type, the aminocarboxylate type, the imidazoline derivative type, and the amideamine type.
  • An amphoteric surfactant etc. are mentioned.
  • 2,3-butanediol may be used as a regulator for controlling the physical properties of the cosmetic composition.
  • it can be utilized as a component or agent for adjusting the viscosity or pH of the cosmetic composition to the desired range.
  • 2,3-butanediol since 2,3-butanediol is utilized in various formulations of the cosmetic composition, it may be used in combination with other diols.
  • the other diol may include, for example, 1,3-propanediol, 1,3-butanediol, hexanediol, pentanediol, and the like.
  • 2,3-butanediol may be used in combination with other polyhydric alcohols such as triols.
  • 2,3-butanediol may be included in the largest amount.
  • 2R, 3S-butanediol may be included in the highest amount (eg, at least 90% by weight of the total weight of the alcohol mixture).
  • At least one of 2,3-butanediol is an antimicrobial, preservative, moisturizer, detergent, wetting agent, stabilizer, softener, viscosity modifier, pH
  • an antimicrobial, preservative moisturizer, detergent, wetting agent, stabilizer, softener, viscosity modifier, pH
  • surfactant, antioxidant, dispersant, carrier, anti-wrinkle agent, antioxidant or anti-inflammatory agent it may be included as a single component.
  • At least one of 2R, 3S-butanediol and 2R, 3R-butanediol may be utilized as the sole preservative, sole antibacterial agent, sole moisturizer, sole cleaner, sole wrinkle improvement agent, sole antioxidant, sole anti-inflammatory agent, etc. of the cosmetic composition. have.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne une composition cosmétique comprenant du 2,3-butanediol. Le 2,3-butanediol peut être utilisé en tant que composant d'un agent antimicrobien, d'un conservateur, d'un agent hydratant, d'un agent de nettoyage, d'un agent mouillant, d'un agent stabilisant, d'un adoucissant, d'un agent d'ajustement de la viscosité, d'un agent d'ajustement du pH, d'un tensioactif, d'un agent de prévention de l'oxydation, d'un agent de dispersion, d'un support, d'un agent d'atténuation des rides, d'un antioxydant ou d'un agent anti-inflammatoire et d'agents analogues dans une composition cosmétique.
PCT/KR2017/013141 2016-11-18 2017-11-17 Composition cosmétique comprenant du 2,3-butanediol Ceased WO2018093210A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2016-0154463 2016-11-18
KR20160154463 2016-11-18

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WO2018093210A2 true WO2018093210A2 (fr) 2018-05-24
WO2018093210A3 WO2018093210A3 (fr) 2018-08-09

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3760195A4 (fr) * 2018-02-27 2022-03-02 GS Caltex Corporation Composition comprenant du 2,3-butanediol en tant que principe actif
CN115427006A (zh) * 2020-04-22 2022-12-02 Gs加德士 包含2,3-丁二醇的分散剂或分散介质组合物以及包含其的化妆品组合物
CN115590795A (zh) * 2021-07-09 2023-01-13 株式会社Lg生活健康（Kr） 包含虎杖根提取物的皮肤弹性增强或皱纹改善用化妆料组合物

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20220039115A (ko) * 2020-09-21 2022-03-29 지에스칼텍스 주식회사 2,3-부탄다이올을 포함하는 조성물
KR102597745B1 (ko) * 2021-04-19 2023-11-03 코스맥스 주식회사 냉장 온도에서 어는 제형을 갖는 화장료 조성물
KR102439976B1 (ko) * 2021-09-13 2022-09-06 (주)닥터솔루션 천연 항산화 물질인 신양벚나무열매 추출물과 멜라토닌을 함유한 천연 항산화 항균 화장료 조성물

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GB9010525D0 (en) * 1990-05-10 1990-07-04 Unilever Plc Cosmetic composition
JP2002212021A (ja) * 2001-01-12 2002-07-31 Naris Cosmetics Co Ltd 化粧料
JP3874273B2 (ja) * 2002-09-24 2007-01-31 株式会社マンダム 毛髪処理剤
JP6141671B2 (ja) * 2013-04-08 2017-06-07 株式会社Adeka β−１，３−１，６−グルカンを含有する組成物
KR102272901B1 (ko) * 2014-10-21 2021-07-02 지에스칼텍스 주식회사 메조-2,3-부탄디올을 방부제로서 함유하는 피부 외용제 조성물

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3760195A4 (fr) * 2018-02-27 2022-03-02 GS Caltex Corporation Composition comprenant du 2,3-butanediol en tant que principe actif
CN115427006A (zh) * 2020-04-22 2022-12-02 Gs加德士 包含2,3-丁二醇的分散剂或分散介质组合物以及包含其的化妆品组合物
JP2023523421A (ja) * 2020-04-22 2023-06-05 ジーエス カルテックス コーポレイション ２，３－ブタンジオールを含む分散剤又は分散媒組成物、及びこれを含む化粧料組成物
EP4140469A4 (fr) * 2020-04-22 2023-11-01 GS Caltex Corporation Dispersant ou composition de milieu de dispersion comprenant du 2,3-butanediol, et composition cosmétique la comprenant
JP2024123151A (ja) * 2020-04-22 2024-09-10 ジーエス カルテックス コーポレイション ２，３－ブタンジオールを含む分散剤又は分散媒組成物、及びこれを含む化粧料組成物
CN115590795A (zh) * 2021-07-09 2023-01-13 株式会社Lg生活健康（Kr） 包含虎杖根提取物的皮肤弹性增强或皱纹改善用化妆料组合物

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WO2018093210A3 (fr) 2018-08-09

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