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WO2025225713A1 - Polyéther polyol, véhicule cosmétique et produit cosmétique - Google Patents

Polyéther polyol, véhicule cosmétique et produit cosmétique

Info

Publication number
WO2025225713A1
WO2025225713A1 PCT/JP2025/015992 JP2025015992W WO2025225713A1 WO 2025225713 A1 WO2025225713 A1 WO 2025225713A1 JP 2025015992 W JP2025015992 W JP 2025015992W WO 2025225713 A1 WO2025225713 A1 WO 2025225713A1
Authority
WO
WIPO (PCT)
Prior art keywords
cosmetic
polyether polyol
present
residue
makeup
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/JP2025/015992
Other languages
English (en)
Japanese (ja)
Inventor
大河 村上
孝治 関口
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.)
NOF Corp
Original Assignee
NOF 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 NOF Corp filed Critical NOF Corp
Publication of WO2025225713A1 publication Critical patent/WO2025225713A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/86—Polyethers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives

Definitions

  • the present invention relates to polyether polyols, cosmetic bases, and cosmetics.
  • Polyether polyols which are produced by ring-opening addition polymerization of cyclic ethers such as ethylene oxide and propylene oxide, or by dehydration condensation of polyhydric alcohols, are used in a variety of applications, including as cosmetic bases, due to their easy control of the balance of hydrophilic and lipophilic properties and molecular weight.
  • Patent Document 1 Polyether polyols are used to improve moisturizing effects and usability.
  • Patent Document 2 discloses that a lotion containing a specific polyether polyol, 2-methacryloyloxyethyl phosphorylcholine/butyl methacrylate copolymer, and a polyhydric alcohol can improve makeup application.
  • amphiphilic polyether polyols that are highly compatible with both water and hydrocarbon oils, with the aim of improving moisturizing power and providing an excellent feel when used.
  • existing amphiphilic polyether polyols sometimes lack sufficient moisturizing power, or, despite being highly compatible with water and polar oils, sometimes exhibit insufficient compatibility with non-polar oils such as hydrocarbon oils. For this reason, no amphiphilic polyether polyols that combine excellent moisturizing effects, excellent feel when used, and high compatibility with water and hydrocarbon oils have been disclosed until now.
  • the present invention was conceived in light of the above-mentioned circumstances, and its purpose is to provide a polyether polyol that has excellent compatibility with water and hydrocarbon oils. It also aims to provide a cosmetic that has excellent moisturizing effects, is non-sticky, and provides excellent makeup application under high humidity conditions and low humidity conditions.
  • a polyether polyol having excellent compatibility with water and hydrocarbon oils can be obtained. Furthermore, the cosmetic composition of the present invention containing the polyether polyol has excellent moisturizing effects, a non-sticky feeling, and excellent makeup application under high humidity conditions and low humidity conditions.
  • the polyether polyol of the present invention is represented by the formula (1): HO- ⁇ (GL) a / (CH 2 CH 2 O) b / (C n H 2n O) c ⁇ -H (1)
  • the polyether polyol of the present invention may be used alone or in combination of two or more. The definitions of the symbols in formula (1) will be explained below.
  • GL is a glycerin residue.
  • glycocerin residue refers to a group represented by formula (2) or formula (3):
  • the glycerin residue may be a group formed from a compound other than glycerin, as long as it is a group having a structure represented by formula (2) or formula (3).
  • a group represented by formula (2) and “a group represented by formula (3)” may be abbreviated as “group (2)” and “group (3),” respectively.
  • both group (2) and group (3) may be present.
  • both group (2) and group (3) are preferably present.
  • the molar ratio of group (2)/group (3) is preferably 40/60 to 99/1, more preferably 40/60 to 90/10, and even more preferably 50/50 to 80/20, from the viewpoints of suppressing stickiness in cosmetics, and improving makeup application under high-humidity conditions and low-humidity conditions.
  • the molar ratio of group (2)/group (3) can be calculated by 13C -NMR measurement.
  • the molar ratio of group (2)/group (3) can be calculated by comparing the integral value of the signal of the methine carbon of group (2) (near 71 ppm) with the integral value of the signal of the methine carbon of group (3) (near 79 ppm).
  • C n H 2n O is an alkanediol residue having 4 to 8 carbon atoms.
  • the alkanediol may be either linear or branched.
  • alkanediol residue having 4 to 8 carbon atoms may be a group formed from a compound different from the alkanediol having 4 to 8 carbon atoms, as long as it has the above structure.
  • 1,2-butanediol residue and the like, which will be described later, also have the same meaning as “alkanediol residue having 4 to 8 carbon atoms.”
  • alkanediol residues having 4 to 8 carbon atoms examples include 1,2-butanediol residue, 1,3-butanediol residue, 1,4-butanediol residue, 1,2-pentanediol residue, 1,3-pentanediol residue, 1,4-pentanediol residue, 1,5-pentanediol residue, neopentyl glycol residue, 1,2-hexanediol residue, 1,3-hexanediol residue, 1,4-hexanediol residue, 1,5-hexanediol residue, 1,6-hexanediol residue, 3-methyl-1,5-pentanediol residue, 1,2-heptanediol residue, 1,7-heptanediol residue, and 1,8-octanediol residue.
  • CnH2nO is preferred from the viewpoints of compatibility with water or hydrocarbon oil, moisturizing effect in cosmetics, and makeup application under high or low humidity conditions.
  • it is an alkanediol residue having 4 to 6 carbon atoms, More preferably, it is a 1,2-butanediol residue, a 1,3-butanediol residue, a 1,4-butanediol residue, a 1,5-pentanediol residue, or a 1,6-hexanediol residue; More preferably, it is a 1,3-butanediol residue, a 1,4-butanediol residue, a 1,5-pentanediol residue, or a 1,6-hexanediol residue.
  • 1,3-butanediol residues 1,4-butanediol residues, and 1,6-hexanediol residues.
  • Most preferred is a 1,3-butanediol residue or a 1,4-butanediol residue.
  • c is a number from 1 to 70, preferably a number from 2 to 40, more preferably a number from 4 to 30, even more preferably a number from 4 to 20, and particularly preferably a number from 4 to 12.
  • (a+b)/c is a number from 0.2 to 8, preferably a number from 0.25 to 5, and more preferably a number from 0.3 to 4, from the viewpoints of compatibility with water or hydrocarbon oil, suppression of stickiness in cosmetics, and cosmetic application under high or low humidity conditions.
  • b/c is a number from 0.5 to 8, preferably a number from 0.75 to 5, and more preferably a number from 1.0 to 4, from the viewpoints of compatibility with water and suppression of stickiness in cosmetics. Note that, in this specification, when c is 0, (a+b)/c is interpreted as ⁇ (infinity).
  • the polyether polyol of the present invention can be produced by known methods.
  • the polyether polyol of the present invention can be produced by dehydration condensation of a polyhydric alcohol in the presence of an acid catalyst such as sulfuric acid at 80°C to 130°C and atmospheric pressure. After dehydration condensation, it is preferable to neutralize the remaining acid catalyst with a base such as potassium hydroxide and remove the resulting salt.
  • the present invention provides a cosmetic base comprising the polyether polyol of the present invention.
  • the cosmetic base of the present invention may be used alone or in combination with two or more types.
  • the present invention also provides a cosmetic containing the cosmetic base of the present invention in an amount of 0.1 to 30% by mass based on the total mass of the cosmetic.
  • the cosmetic of the present invention is not particularly limited and may be an aqueous cosmetic, a water-in-oil or oil-in-water emulsion cosmetic, or an oil-based cosmetic.
  • cosmetics include skin care cosmetics such as lotions, serums, emulsions, creams, packs, and sunscreen creams; body cosmetics; makeup removers such as cleansing oils and cleansing waters; skin cosmetics such as body soaps, hand soaps, and facial cleansing pastes; hair cosmetics such as shampoos, treatments, hair liquids, hair oils, hair tonics, and hair growth agents; and makeup cosmetics such as makeup bases, liquid foundations, and BB creams.
  • the content of the cosmetic base of the present invention is 0.1 to 30% by mass, preferably 0.5 to 15% by mass, based on the total mass of the cosmetic of the present invention.
  • the cosmetic of the present invention preferably contains water (more preferably purified water). Furthermore, the cosmetic of the present invention may contain other components different from the cosmetic base and water of the present invention, as needed, as long as the effects of the present invention are not impaired. There are no particular limitations on the other components, as long as they are components commonly used in cosmetics.
  • Examples of other components include humectants, hydrocarbons, higher alcohols, higher fatty acids and their triglycerides, ester oils, animal and vegetable oils, silicones, vitamins, UV absorbers, water-soluble polymers, antioxidants, cationic surfactants, anionic surfactants, amphoteric surfactants, nonionic surfactants, sequestering agents, ethanol, thickeners, preservatives, colorants, pigments, and fragrances. Only one type of other component may be used, or two or more types may be used in combination.
  • the total amount of the other ingredients is preferably 5 to 99% by mass, and more preferably 10 to 85% by mass, of the entire cream, liquid foundation, or sunscreen cream of the present invention, from the viewpoint of emollient effect and moisture evaporation inhibitory effect.
  • Water is the remainder of the cream, liquid foundation, or sunscreen cream of the present invention (i.e., the remainder of the cream, liquid foundation, or sunscreen cream other than the cosmetic base and other ingredients of the present invention).
  • the total amount of the other ingredients is preferably 5 to 80% by mass, and more preferably 10 to 60% by mass, based on the total amount of the shampoo or body soap of the present invention, from the viewpoint of cleansing performance.
  • Water is the remainder of the shampoo or body soap of the present invention (i.e., the remainder of the shampoo or body soap other than the cosmetic base of the present invention and other ingredients).
  • the cosmetic of the present invention is a cleansing oil and other ingredients are used
  • the total amount of the other ingredients is preferably 40 to 99.5% by mass, and more preferably 60 to 99% by mass, based on the total amount of the cleansing oil of the present invention, from the standpoint of cleansing performance.
  • Example Polyether Polyol 1 manufactured by Kyowa Chemical Industry Co., Ltd.
  • adsorbent manufactured by Kyowa Chemical Industry Co., Ltd.
  • the temperature was 90 ° C.
  • the pressure was -0.097 MPa (gauge pressure) or less
  • the mixture was subjected to adsorption treatment for 1 hour under nitrogen bubbling, followed by filtration to obtain Example Polyether Polyol 1.
  • Example Polyether Polyol 5 The molar ratio of group (2) / group (3) of Example Polyether Polyol 5 was calculated using the following method and was found to be 67/33.
  • glycerin was used as the raw polyhydric alcohol forming GL in formula (1), and the raw polyhydric alcohols forming CH 2 CH 2 O (hereinafter referred to as “raw material for CH 2 CH 2 O”) and the raw polyhydric alcohols forming C n H 2n O (hereinafter referred to as “raw material for C n H 2n O”) shown in Table 1 or Table 2 below were used.
  • Tables 1 and 2 show a to c, n, raw materials for CH 2 CH 2 O, raw materials for C n H 2n O, a+b, (a+b)/c, and Mw of the obtained Example Polyether Polyols 1 to 9 and Comparative Example Polyether Polyols 1 to 7.
  • Mw was calculated using gel permeation chromatography (GPC) under the following conditions.
  • GPC was performed using a SHODEX (registered trademark) GPC101 dedicated GPC system, a SHODEX RI-71s differential refractometer, a SHODEX KF-G guard column, and three SHODEX KF804L columns connected in series.
  • the column temperature was 40°C, and tetrahydrofuran was used as the developing solvent at a flow rate of 1 mL/min.
  • Example Cosmetics 1 to 9 and Comparative Cosmetics 1 to 9 were produced by mixing and stirring the Example polyether polyol or Comparative polyether polyol, common ingredients, and purified water in the amounts shown in Tables 4 or 5.
  • the composition of the common ingredients is shown in Table 6.
  • "BG" in Table 6 is the cosmetic name indicated by the Japan Cosmetic Industry Association, and stands for 1,3-butylene glycol.
  • Example Polyether Polyols 1 to 9 had excellent compatibility with hydrocarbon oils and water. Furthermore, as is clear from Table 4, Example Cosmetics 1 to 9 had excellent moisturizing effects, lack of stickiness, and makeup application under high humidity and low humidity conditions.
  • Comparative Example Polyether Polyols 1 to 9 and Comparative Example Cosmetics 1 to 9 were inferior in one of the above evaluation items.
  • Comparative Example Polyether Polyol 1 which has an (a+b)/c ratio of greater than 8, had low compatibility with hydrocarbon oils. Furthermore, Comparative Cosmetic 1, which contained Comparative Example Polyether Polyol 1, was poor in terms of lack of stickiness, makeup application under high humidity conditions, and makeup application under low humidity conditions.
  • Comparative Example Polyether Polyol 2 in which (a + b)/c is less than 0.2, had poor compatibility with water. Furthermore, Comparative Example Cosmetic 2, which contained Comparative Example Polyether Polyol 2, separated and could not be evaluated.
  • Comparative Example Polyether Polyol 3 in which n is less than 4, had low compatibility with hydrocarbon oils. Furthermore, Comparative Cosmetic 3, which contained Comparative Example Polyether Polyol 3, had poor moisturizing effect, makeup application under high humidity conditions, and makeup application under low humidity conditions.
  • Comparative example polyether polyol 4 in which b exceeded 80 and a + b exceeded 90, had low compatibility with hydrocarbon oils. Furthermore, comparative cosmetic preparation 4, which contained comparative example polyether polyol 4, was poor in terms of lack of stickiness, makeup application under high humidity conditions, and makeup application under low humidity conditions.
  • Comparative Example Polyether Polyol 5 in which (a + b)/c was greater than 8 and c was less than 1, had poor compatibility with hydrocarbon oils. Furthermore, Comparative Cosmetic 5, which contained Comparative Example Polyether Polyol 5, was inferior in terms of lack of stickiness, makeup application under high humidity conditions, and makeup application under low humidity conditions.
  • Comparative Example Polyether Polyol 8 a copolymer of ethylene oxide and propylene oxide with a different structure from the polyether polyol of the present invention, exhibited low compatibility with hydrocarbon oils. Furthermore, Comparative Cosmetic 8, which contained Comparative Example Polyether Polyol 8, exhibited poor non-stickiness and poor makeup application under high and low humidity conditions.
  • Comparative Polyether Polyol 9 a copolymer of glycidol and propylene oxide with a different structure from the polyether polyols of the present invention, exhibited low compatibility with hydrocarbon oils. Furthermore, Comparative Cosmetic 9, which contained Comparative Polyether Polyol 9, exhibited poor makeup application under both high-humidity and low-humidity conditions.
  • Formulation examples of cosmetics containing the polyether polyol of the present invention are shown in Tables 7 to 20 below.
  • the amounts of ingredients shown in Tables 7 to 20 are values based on the entire cosmetic.
  • the cosmetic name indicated by the Japan Cosmetic Industry Association has been used as the name of each ingredient listed in Tables 7 to 20 below, as appropriate. It should be noted that the present invention is not limited to the following formulation examples.
  • the polyether polyol of the present invention has excellent compatibility with water and hydrocarbon oils, making it useful as a cosmetic base, etc.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Cosmetics (AREA)

Abstract

La présente invention concerne un polyéther polyol représenté par la formule (1) : HO-{(GL)a/(CH2CH2O)b/(CnH2nO)c}-H, les symboles étant tels que définis dans la description ; un véhicule cosmétique comprenant le polyéther polyol ; et un produit cosmétique comprenant le véhicule. Le polyéther polyol selon la présente invention est excellent en termes de compatibilité avec l'eau et de compatibilité avec une huile hydrocarbonée. Le produit cosmétique selon la présente invention est excellent en termes d'effet hydratant, d'absence d'effet collant, de fixation du maquillage dans des conditions de forte humidité et de fixation du maquillage dans des conditions de faible humidité.
PCT/JP2025/015992 2024-04-26 2025-04-25 Polyéther polyol, véhicule cosmétique et produit cosmétique Pending WO2025225713A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2024072812 2024-04-26
JP2024-072812 2024-04-26

Publications (1)

Publication Number Publication Date
WO2025225713A1 true WO2025225713A1 (fr) 2025-10-30

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006282539A (ja) * 2005-03-31 2006-10-19 Nof Corp 化粧料用基剤およびそれを配合してなる化粧料
JP2010530887A (ja) * 2007-06-21 2010-09-16 ダウ グローバル テクノロジーズ インコーポレイティド パーソナルケア組成物における疎水性成分のための安定剤
JP2017088517A (ja) * 2015-11-05 2017-05-25 株式会社ダイセル ポリグリセリン誘導体、及びこれを含有する皮膚外用剤
JP2018177732A (ja) * 2017-04-19 2018-11-15 日油株式会社 油性化粧料
JP2023131115A (ja) * 2022-03-08 2023-09-21 日油株式会社 化粧用基剤およびそれを含む化粧料
WO2024053560A1 (fr) * 2022-09-05 2024-03-14 株式会社 資生堂 Base de produit cosmétique

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006282539A (ja) * 2005-03-31 2006-10-19 Nof Corp 化粧料用基剤およびそれを配合してなる化粧料
JP2010530887A (ja) * 2007-06-21 2010-09-16 ダウ グローバル テクノロジーズ インコーポレイティド パーソナルケア組成物における疎水性成分のための安定剤
JP2017088517A (ja) * 2015-11-05 2017-05-25 株式会社ダイセル ポリグリセリン誘導体、及びこれを含有する皮膚外用剤
JP2018177732A (ja) * 2017-04-19 2018-11-15 日油株式会社 油性化粧料
JP2023131115A (ja) * 2022-03-08 2023-09-21 日油株式会社 化粧用基剤およびそれを含む化粧料
WO2024053560A1 (fr) * 2022-09-05 2024-03-14 株式会社 資生堂 Base de produit cosmétique

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