WO2023127773A1 - シリコーンポリウレタン - Google Patents

シリコーンポリウレタン Download PDF

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Publication number
WO2023127773A1
WO2023127773A1 PCT/JP2022/047819 JP2022047819W WO2023127773A1 WO 2023127773 A1 WO2023127773 A1 WO 2023127773A1 JP 2022047819 W JP2022047819 W JP 2022047819W WO 2023127773 A1 WO2023127773 A1 WO 2023127773A1
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WIPO (PCT)
Prior art keywords
formula
parts
silicone polyurethane
represented
dimethiconol
Prior art date
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Ceased
Application number
PCT/JP2022/047819
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English (en)
French (fr)
Japanese (ja)
Inventor
卓志 竹下
加奈子 和田
祐二 増渕
勇輔 谷口
健悟 工藤
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Kose Corp
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Kose Corp
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Publication date
Application filed by Kose Corp filed Critical Kose Corp
Priority to KR1020247024335A priority Critical patent/KR20240123375A/ko
Priority to CN202280086432.1A priority patent/CN118541407A/zh
Priority to JP2023570994A priority patent/JPWO2023127773A1/ja
Publication of WO2023127773A1 publication Critical patent/WO2023127773A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/61—Polysiloxanes
    • 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
    • A61K8/89—Polysiloxanes
    • A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
    • A61K8/898—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3203—Polyhydroxy compounds
    • C08G18/3206—Polyhydroxy compounds aliphatic
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere

Definitions

  • the present invention relates to silicone polyurethanes that can be used as gelling agents, film-forming agents, emulsifiers, surface treatment agents, and the like.
  • Polyurethanes have traditionally been applied in various fields such as electronic/electrical materials, automobile/railway vehicle materials, civil engineering and construction materials, paints/adhesives, medical materials, and clothing materials. Molecular design studies are being conducted.
  • Patent Document 1 in a urethane resin composition containing a urethane prepolymer having an isocyanate group and an ether-modified polysiloxane, by setting the molecular weight dispersity of the ether-modified polysiloxane to a predetermined value, as an industrial member, It is described that molded articles having excellent mechanical properties, chemical resistance, etc. can be obtained.
  • a prepolymer is formed by mixing a diol and an aliphatic diisocyanate that is in excess of the equivalent weight to the diol, and from this prepolymer and an alkylsilicate having an amino group or an imino group, After forming a modified prepolymer by mixing with a coupling agent, this modified prepolymer and a silanol compound are mixed to introduce siloxane, which can be used for electronic parts, gas separation membranes, etc. Siloxane-containing polyurethanes with modulus, thermal decomposition temperature, chemical resistance, etc. are disclosed.
  • a urethane-modified silicone obtained by reacting a silicone compound, an oxyalkylene compound, a diol compound, a monofunctional alcohol compound, and a diisocyanate compound, each having a specific structure, increases various types of oily components. It is disclosed that it can be used as an oil gelling agent for cosmetics because it can be viscous or gelled. In addition to compatibility with oils, these gelling agents for cosmetic oils have elasticity and resilience that can smooth uneven skin such as wrinkles and follow changes in facial expressions and movements of the skin such as blinking. etc. is required. When used as a film-forming agent, it is required to be able to follow the movement of the skin and form a film having flexibility and strength in order to maintain the cosmetic effect.
  • the present invention provides a polyurethane that can be dissolved in an oil agent to form a gel with excellent elasticity, resilience, etc., and can be formed into a film having both flexibility and strength.
  • the task is to
  • the present inventors conducted intensive studies to solve the above problems, and found that a silicone polyurethane having constitutional units based on an isocyanate compound, dimethiconol, and alkylene glycol each having a specific structure has good solubility in an oil agent.
  • the present inventors have found that a gel having high elasticity, resilience, etc. can be formed, and that a film having high strength and excellent flexibility can be obtained by using this silicone polyurethane, thus completing the present invention.
  • the present invention provides the following formula (1) OCN-R 1 -NCO (1) (Wherein, R 1 represents an alkylene group having 2 to 9 carbon atoms) A structural unit based on an isocyanate compound represented by Formula (2) below (Wherein, n represents an integer from 1 to 100) A structural unit based on dimethiconol represented by Formula (3) below HO—R 2 —OH (3) (Wherein, R 2 represents a linear or branched alkylene group having 2 to 9 carbon atoms which may have an ether bond) It is a silicone polyurethane having a structural unit based on an alkylene glycol represented by.
  • the silicone polyurethane of the present invention can be dissolved in an oil to form an oil gel with excellent elasticity and restoring force. Also, by using the silicone polyurethane of the present invention, a film having strength and flexibility can be formed.
  • FIG. 10 is a graph showing the difference in stress between the first time and the second time in a tensile test measured with a texture analyzer in Test Example 3.
  • FIG. 3 is a photograph of the state of the film after the tensile test in Test Example 3.
  • FIG. 10 is a graph showing the difference in stress between the first time and the second time in a tensile test measured with a texture analyzer in Test Example 3.
  • FIG. 3 is a photograph of the state of the film after the tensile test in Test Example 3.
  • % means “% by mass” and “part” means “part by mass” unless otherwise specified. Also, when a numerical range is expressed using “ ⁇ ”, the range includes the numerical values at both ends.
  • the silicone polyurethane of the present invention has the following formula (1) OCN-R 1 -NCO (1) (Wherein, R 1 represents an alkylene group having 2 to 9 carbon atoms) A structural unit based on an isocyanate compound (hereinafter sometimes referred to as “isocyanate compound (1)”) represented by Formula (2) below (Wherein, n represents an integer from 1 to 100) A structural unit based on dimethiconol (hereinafter sometimes referred to as “dimethiconol (2)”) represented by Formula (3) below HO—R 2 —OH (3) (Wherein, R 2 represents a linear or branched alkylene group having 2 to 9 carbon atoms which may have an ether bond) and a structural unit based on an alkylene glycol represented by (hereinafter sometimes referred to as "alkylene glycol (3)").
  • R 1 represents an alkylene group having 2 to 9 carbon atoms, and the alkylene may be linear or branched, but linear is preferred.
  • alkylene group having 2 to 9 carbon atoms include ethylene, n-propylene, n-butylene, n-pentylene, n-hexylene and the like.
  • isocyanate compound represented by the above formula (1) include 1 ,4-tetramethylene diisocyanate, 1,5-pentamethylene diisocyanate, 1,6-hexamethylene diisocyanate and the like.
  • An isocyanate is preferred from the viewpoint of the elasticity and restorability of the formed gel, the flexibility of the film, and the like.
  • n is an integer of 1 to 100, preferably 25 to 75, more preferably 40 to 75.
  • the weight average molecular weight is not particularly limited, it is preferably 1,500 to 15,000, more preferably 4,000 to 11,000, and even more preferably 6,000 to 11,000 from the viewpoint of the elasticity and restorability of the formed gel and the flexibility of the film.
  • the weight average molecular weight means a value (polystyrene conversion value) measured by gel permeation chromatography (GPC).
  • R 2 represents a linear or branched alkylene group having 2 to 9 carbon atoms which may have an ether bond, specifically ethylene glycol, propylene glycol, 1,3 -butylene glycol, 1,4-butylene glycol, diethylene glycol, triethylene glycol, dipropylene glycol, tripropylene glycol and the like.
  • ethylene glycol represented by the following formula (5) is preferable from the viewpoint of the elasticity and restorability of the formed gel, the flexibility of the film, and the like.
  • the isocyanate compound (1) is reacted with the dimethiconol (2) to obtain a polyurethane prepolymer represented by the following formula (6) (hereinafter referred to as "polyurethane (sometimes referred to as “prepolymer (6)") is obtained, and then this polyurethane prepolymer (6) and alkylene glycol (3) are polyaddition-reacted.
  • polyurethane sometimes referred to as "prepolymer (6)
  • R 1 and n have the same meanings as above, R 1 represents an alkylene group having 2 to 9 carbon atoms, and n represents an integer of 1 to 100.
  • m represents an integer of 1 to 7, preferably 1 to 3, more preferably 1 to 2, from the viewpoints of the elasticity and restorability of the formed gel and the flexibility of the film.
  • the molar ratio of the dimethiconol (2) to the isocyanate compound (1) is preferably from 0.5 to 0.875, more preferably from 0.5 to 0.75, from the viewpoint of the elasticity and restorability of the formed gel and the flexibility of the film. Further, it is preferably 0.5 to 0.67.
  • the weight average molecular weight of the urethane prepolymer is preferably 2,000 to 30,000, more preferably 4,000 to 20,000, even more preferably 4,000 to 15,000.
  • the silicone polyurethane of the present invention represented by the following formula (7) is obtained.
  • the silicone polyurethane is preferably 10,000 to 300,000, more preferably 20,000 to 200,000, even more preferably 30,000 to 100,000.
  • the weight average molecular weight of the silicone polyurethane is less than 100,000, the molar ratio of dimethiconol (2) to ethylene glycol (3) (dimethiconol (2)/ethylene glycol (3)) is preferably 4 or less. is more preferably 1 or less, and more preferably 1 or less.
  • the weight average molecular weight of the silicone polyurethane is 100,000 or more
  • the molar ratio (dimethiconol (2)/ethylene glycol (3)) is preferably 6 or less, more preferably 4 or less. It is more preferably 2 or less, and the lower limit is preferably 1 or more.
  • the most preferred combination of weight average molecular weight and molar ratio is a weight average molecular weight of 30,000 to 100,000, and the molar ratio of dimethiconol (2) to ethylene glycol (3) (dimethiconol (2)/ethylene glycol (3)) is 0.3. ⁇ 0.7.
  • R 1 , R 2 , n and m have the same meanings as above.
  • r represents an integer of 1 to 3, preferably 1 to 2, more preferably 1;
  • s represents an integer of 1 to 50, preferably 2 to 10, more preferably 5 to 10.
  • Preferred embodiments of the silicone polyurethane of the present invention are represented by the following formula (8).
  • the silicone polyurethane of the present invention can also be obtained by polymerizing the isocyanate compound (1), dimethiconol (2), and alkylene glycol (3).
  • the molar ratio of each component may be the same as above.
  • the silicone polyurethane of the present invention forms a plurality of ring-shaped clusters (tufts) by associating the hydrophilic moieties within the molecule based on alkylene glycol (3), and the isocyanate compound (1) and dimethiconol (2).
  • a hydrophilic group association thickening mechanism is expressed. It is presumed that the hydrophobic portion imparts flexibility and oil-solubility, and the interaction of the polar groups of the hydrophilic portion within the molecule imparts gelling power and resilience.
  • the silicone polyurethane of the present invention has excellent compatibility with oil agents and can form a silicone polyurethane gel.
  • oil agents include hydrocarbon oils, ester oils, oils and fats, silicone oils, fluorine-based oils, and the like, regardless of their origin, such as animal oils, vegetable oils, and synthetic oils.
  • silicone oils and hydrocarbon oils are preferred because they have high compatibility, form gels with high elasticity and resilience, and are excellent in flexibility and strength of films obtained by curing.
  • silicone oils include dimethylpolysiloxane, cyclomethicone, methylphenylpolysiloxane, diphenylpolysiloxane, methyltrimethicone, caprylylmethicone, trifluoropropylcyclotetrasiloxane, and trifluoropropylcyclopentasiloxane.
  • hydrocarbon oils include liquid paraffin, squalane, polybutene, polyisobutylene, undecane, tridecane, isododecane, (C13-15) alkanes, etc., and one or more of these can be used.
  • the silicone polyurethane gel can be obtained by polymerizing a silicone polyurethane in an oil or by mixing a silicone polyurethane and an oil in advance. For example, isocyanate compound (1) and dimethiconol (2) are reacted in an oil to obtain polyurethane prepolymer (6), and then this polyurethane prepolymer (6) and alkylene glycol (3) undergo a polyaddition reaction.
  • a silicone polyurethane gel is obtained by letting the A silicone polyurethane gel can also be obtained by charging dimethiconol (2) and alkylene glycol (3), uniformly mixing them, adding isocyanate compound (1), and allowing them to react.
  • Cosmetics can be produced by using the silicone polyurethane or silicone polyurethane gel of the present invention in combination with known cosmetic ingredients according to a conventional method.
  • the content of the silicone polyurethane in the cosmetic is not particularly limited, and can be arbitrarily set according to the dosage form of the cosmetic. 01 to 10 are more preferred.
  • Cosmetic ingredients that can be used in combination with the silicone polyurethane of the present invention include, for example, volatile ingredients, surfactants, oils, powders, aqueous ingredients, alcohols, water-soluble polymers, UV absorbers, moisturizing agents, agents, gelling agents and thickeners, antifading agents, antioxidants, antifoaming agents, cosmetic ingredients (whitening agents, cell activators, anti-inflammatory agents, blood circulation promoters, skin astringents, antiseborrheic agents, etc.) , preservatives, antibacterial agents, fragrances, vitamins, amino acids, nucleic acids, hormones, and the like.
  • various dosage forms such as liquid, milky lotion, cream, solid, paste, gel, powder, press, multi-layer, mousse, etc. It can be used to manufacture cosmetics in the form of sprays, sticks, etc., and cosmetics intended for various areas of application, such as make-up cosmetics, skin care cosmetics, hair cosmetics, and cosmetics. It can be used in the production of perspiration agents, UV protection cosmetics, and the like.
  • cosmetic items such as lotion, milky lotion, beauty essence, pack, all-in-one gel, cream, body milk, oil cleansing, cleansing cream, basic cosmetics such as sunscreen, styling water, hair such as hair wax.
  • Cosmetics for makeup, mascara, lip gloss, lipstick, eye shadow, eyeliner, foundation, face color, concealer, and make-up cosmetics such as makeup base are exemplified.
  • the weight average molecular weight of the silicone polyurethane in the obtained silicone polyurethane gel was 25,364 by GPC measurement (converted to polystyrene).
  • the silicone polyurethane gels of Examples 1 to 7 were evaluated excellent in terms of solubility and gelling power. This is thought to be because the dimethiconol portion of the silicone polyurethane gel exhibits a high affinity for silicone and hydrocarbon solvents, and the ethylene glycol portion acts as a pseudo-crosslinking point to form a highly elastic gel. be done.
  • Comparative Examples 1 and 2 although uniform dissolution is possible, unlike the gelation mechanism by ethylene glycol and dimethiconol in Examples 1 to 7, Comparative Example 1 has a polysaccharide gelation mechanism, and Comparative Example 2 has a gelation mechanism. is a gelation mechanism by silicone wax, so sufficient gelling power is not obtained.
  • the silicone polyurethane gels of Examples 8 and 9 have high film flexibility because they are composed of a pseudo-crosslinked structure even when a tensile stress is applied. As a result, the difference in the magnitude of the stress applied to the film was very small, and the flexibility of the film was excellent.
  • the film-forming agents of Comparative Examples 3 to 6 all of them have a crosslinked network structure in the molecule, and the film itself has a hard property, so when tensile stress is applied for the first time, However, when the film was destroyed and the second tensile stress was applied, the film was already destroyed by the first tension, so the stress in the film was not detected in the second time. The result was that the difference in tensile stress in the second cycle was large, and Comparative Examples 3 to 6 were all inferior in flexibility.
  • Oil-based solid concealer According to the formulation shown in Table 5 below, an oil-based solid concealer was prepared according to the following method. The obtained oily solid cosmetics were evaluated for firmness, non-stressfulness, and makeup lasting effect by the following evaluation methods. The results are also shown in Table 5.
  • the oil-based solid concealers of Examples 10 to 15 were oil-based concealers that were excellent in firmness, no burden, and makeup lasting effects.
  • the oily solid concealers of Comparative Examples 7 to 9 were inferior in the following points.
  • the oil-based solid concealer of Comparative Example 7 has low elasticity and adhesion to the skin of the cross-linked silicone gel, and thus is particularly inferior in firmness and makeup lasting effect.
  • the saccharide gel has a relatively high cosmetic lasting effect due to its adhesiveness to the skin, it has a sticky feeling peculiar to saccharides, and because of its low elasticity, it does not spread well and is inferior in firmness and lack of burden.
  • the oil-based solid concealer of Comparative Example 9 was inferior in the elastic feeling of the wax oil gel, so that the firmness was low and the makeup lasting effect was also inferior.
  • W/O type liquid foundation A W/O type liquid foundation was prepared according to the following manufacturing method according to the formulation shown in Table 6 below. The obtained W/O type liquid foundation was evaluated for firmness, non-stressfulness, and makeup lasting effect by the same evaluation method as for the oil-based solid concealer. The results are also shown in Table 6.
  • the W/O type liquid foundations of Examples 16 to 19 were excellent in firmness, no burden, and makeup lasting effect.
  • the W/O type liquid foundations of Comparative Examples 10 to 12 were inferior in the following points.
  • the W/O type liquid foundation of Comparative Example 10 has low flexibility of trimethylsiloxysilicate, so it is particularly inferior in feeling of no burden.
  • the agent has a relatively good firmness, it has a tight feeling peculiar to acrylate resins and has low makeup durability, so it does not feel burdensome and is inferior in makeup lasting effect.
  • the W/O type liquid foundation of Comparative Example 12 which is a fluorine-modified silicone resin, has high water and oil repellency and relatively high makeup lasting effect, but has low flexibility and does not feel burdensome. .
  • the silicone polyurethane of the present invention can be dissolved in an oil agent to form an oil gel having excellent elasticity, restoring force, etc., and can also form a film having strength and flexibility. It can be used as an agent, film-forming agent, emulsifier, surface treatment agent, and the like.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
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  • Wood Science & Technology (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
PCT/JP2022/047819 2021-12-28 2022-12-26 シリコーンポリウレタン Ceased WO2023127773A1 (ja)

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KR1020247024335A KR20240123375A (ko) 2021-12-28 2022-12-26 실리콘 폴리우레탄
CN202280086432.1A CN118541407A (zh) 2021-12-28 2022-12-26 硅酮聚氨基甲酸酯
JP2023570994A JPWO2023127773A1 (https=) 2021-12-28 2022-12-26

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JP2011225729A (ja) * 2010-04-20 2011-11-10 Adeka Corp 珪素含有ウレタン化合物及びその製造方法、並びにその化合物を含有する組成物
US20170029554A1 (en) * 2015-07-27 2017-02-02 Hyundai Motor Company Thermoplastic polyurethane composition for injection molding and method of manufacturing the same
KR20170053806A (ko) * 2015-11-06 2017-05-17 한국콜마주식회사 혼합성 및 안정성이 우수한 메이크업 화장료 조성물

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