WO2021215825A1 - Composition de polysiloxane et silicone hydrophile préparée à partir de celle-ci - Google Patents

Composition de polysiloxane et silicone hydrophile préparée à partir de celle-ci Download PDF

Info

Publication number
WO2021215825A1
WO2021215825A1 PCT/KR2021/005024 KR2021005024W WO2021215825A1 WO 2021215825 A1 WO2021215825 A1 WO 2021215825A1 KR 2021005024 W KR2021005024 W KR 2021005024W WO 2021215825 A1 WO2021215825 A1 WO 2021215825A1
Authority
WO
WIPO (PCT)
Prior art keywords
weight
hydrophilic
silicone
compound
parts
Prior art date
Application number
PCT/KR2021/005024
Other languages
English (en)
Korean (ko)
Inventor
김태우
박지윤
강경훈
이지혜
Original Assignee
주식회사 케이씨씨실리콘
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 주식회사 케이씨씨실리콘 filed Critical 주식회사 케이씨씨실리콘
Publication of WO2021215825A1 publication Critical patent/WO2021215825A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/12—Polysiloxanes containing silicon bound to hydrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/05—Alcohols; Metal alcoholates
    • C08K5/053—Polyhydroxylic alcohols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/15—Heterocyclic compounds having oxygen in the ring
    • C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
    • C08K5/1515—Three-membered rings

Definitions

  • the present invention relates to a polysiloxane composition comprising a hydrophilic compound, and a hydrophilic silicone having excellent hydrophilicity prepared therefrom.
  • Silicon is used as a raw material in various fields because of its excellent stability and feeling of use.
  • the silicone applied to the cosmetic composition is typically prepared by reacting an alkenyl group-containing polysiloxane with a Si—H group-containing hydrogen polysiloxane.
  • the silicone prepared as described above lacks hydrophilicity, and there is a limitation in reducing the storage stability and fairness of cosmetics including the same.
  • Patent Document 1 discloses (A) a gelling agent for an oil-based raw material, including a co-modified organopolysiloxane having a hydrophilic group and a group having a siloxane dendron structure. wherein the co-modified organopolysiloxane is obtained by reacting (a) an organohydrogensiloxane, (b) a hydrophilic derivative having a reactive unsaturated group, and (c) a siloxane dendron having a reactive unsaturated group.
  • silicone modified with polyglycerol or glucose has a problem of phase separation and unpleasant odor due to residual unreacted glycerol or raw glucose generated during manufacture.
  • the polymerization degree of glycerol is high, workability is deteriorated due to the high viscosity of the manufactured silicone, and stickiness occurs when applied to the skin, so that there is a problem that a moist and smooth feeling cannot be obtained.
  • the degree of improvement in hydrophilicity due to the use of glycerol or glucose, which is a hydrophilic raw material was insufficient, and the storage property of the manufactured silicone was low, resulting in yellowing.
  • Patent Document 1 Korean Patent Registration No. 1833959 (published on August 8, 2012)
  • the present invention provides a composition capable of producing an eco-friendly silicone having excellent hydrophilicity, stability, workability and feeling, and less odor, and a hydrophilic silicone prepared therefrom.
  • the present invention includes a hydrophilic compound, an organopolysiloxane and an organohydrogenpolysiloxane,
  • the hydrophilic compound is prepared by reacting a glycidyl compound and a polyhydric alcohol compound in a weight ratio of 1: 1.0 to 1.5,
  • the organopolysiloxane provides a polysiloxane composition comprising an alkenyl group.
  • the present invention provides a hydrophilic silicone prepared from the polysiloxane composition.
  • the polysiloxane composition according to the present invention may include a hydrophilic compound to prepare a silicone having excellent hydrophilicity.
  • the silicone prepared from the composition has excellent hydrophilicity, stability, workability and feel, and is less odorous and environmentally friendly, so it can be used as an emulsifier in a cosmetic composition.
  • weight average molecular weight is measured by a conventional method known in the art, for example, it can be measured by a GPC (gel permeation chromatograph) method.
  • the polysiloxane composition according to the present invention includes a hydrophilic compound, an organopolysiloxane and an organohydrogenpolysiloxane.
  • the hydrophilic compound serves to improve the hydrophilicity of the prepared silicone.
  • the hydrophilic compound is prepared by reacting a glycidyl compound with a polyhydric alcohol compound.
  • the hydrophilic compound is prepared by reacting a glycidyl compound and a polyhydric alcohol compound in a weight ratio of 1:1.0 to 1.5, and may be represented by the following Chemical Formula 1.
  • R 1 is C 2-10 alkenyl
  • R 2 and R 3 are each independently C 1-10 alkylene
  • n is an integer from 1 to 3.
  • R 1 may be C 2-8 alkenyl or C 2-5 alkenyl
  • R 2 and R 3 may each independently be C 1-7 alkylene or C 1-4 alkylene.
  • the alkylene and alkenyl may be linear or branched.
  • the alkylene refers to a branched or straight chain or cyclic divalent radical derived by the removal of one hydrogen atom from a carbon atom of an alkyl group.
  • the alkylene is methylene (-CH 2 -), 1,1-ethylene (-CH(CH 3 )-), 1,2-ethylene (-CH 2 CH 2 -), 1,1-propylene (-CH(CH 2 CH 3 )-), 1,2-propylene (-CH 2 CH(CH 3 )-), 1,3-propylene (-CH 2 CH 2 CH 2 -), 1,4-butyl ene (-CH 2 CH 2 CH 2 CH 2 -), 2,4-butylene (-CH 2 (CH 3 )CH 2 CH 2 -), and the like, but are not limited thereto.
  • the hydrophilic compound is prepared by reacting a glycidyl compound and a polyhydric alcohol compound in a weight ratio of 1: 1.0 to 1: 1.5, specifically, a glycidyl compound and a polyhydric alcohol compound 1: 1.01 to 1: 1.45, or It may be prepared by reacting in a weight ratio of 1: 1.10 to 1: 1.40.
  • the weight ratio is less than 1:1.0, the crosslinking density is high and the viscosity is high, so the problem of insufficient performance such as the feeling of use of silicone, for example, softness and spreadability, and unreacted substances remain, which may cause a problem in poor workability.
  • the weight ratio is more than 1:1.5, the crosslinking density is lowered, the hydrophilicity is insufficient, and the emulsification performance is lowered, which may cause phase separation of the product later.
  • the hydrophilic compound may have a hydroxyl group (-OH) content of 10 to 40 wt%, or 15 to 35 wt%, based on the total weight of the compound.
  • a hydroxyl group (-OH) content of 10 to 40 wt%, or 15 to 35 wt%, based on the total weight of the compound.
  • the hydroxyl group content of the hydrophilic compound is within the above range, it functions as an emulsification auxiliary, improves compatibility with an aqueous system, and provides an excellent moisturizing effect.
  • the hydrophilic group content of the hydrophilic compound is less than 10% by weight, the hydrophilic group content may be lowered, resulting in poor emulsification performance and lower emulsion stability.
  • the hydroxyl group content of the hydrophilic compound is more than 40% by weight, the lipophilicity of the prepared silicone is relatively low, so that the emulsification performance may be deteriorated and the emulsion stability may be lowered.
  • the hydrophilic compound may have a weight average molecular weight (Mw) of 100 to 500 g/mol and 200 to 400 g/mol.
  • Mw weight average molecular weight
  • the weight average molecular weight of the hydrophilic compound is less than 100 g/mol, unreacted substances in the polyhydric alcohol compound or the glycidyl compound remain to suppress the silicone crosslinking reaction and may cause phase separation of the product later.
  • the weight average molecular weight of the hydrophilic compound is more than 500 g/mol, the hydroxyl group of the polyhydric alcohol compound causes an additional ring-opening reaction, and the hydrophilic group content of the prepared hydrophilic compound is lowered, thereby reducing the emulsification performance.
  • the hydrophilic compound may be included in the composition in an amount of 0.1 to 5 parts by weight, or 0.5 to 3 parts by weight based on 5 to 20 parts by weight of the organopolysiloxane.
  • the content of the hydrophilic compound is less than 0.1 parts by weight, the emulsification performance of the prepared silicone is lowered and compatibility with the aqueous system is lowered. This insufficient problem and the high viscosity of silicone may result in poor workability.
  • the organopolysiloxane is the main resin of the polysiloxane composition.
  • the organopolysiloxane may include an alkenyl group, for example, an alkenyl group at both terminals.
  • the organopolysiloxane may be represented by Formula 2 below.
  • R 5 to R 8 are each independently a substituted or unsubstituted C 1-10 alkyl group or C 2-10 alkenyl group,
  • R 9 and R 10 are each independently a substituted or unsubstituted C 2-10 alkenyl group
  • m 50 to 600.
  • R 5 to R 8 may each independently be a substituted or unsubstituted C 1-6 alkyl group or C 1-3 alkyl group, or a C 2-8 alkenyl group or a C 2-4 alkenyl group.
  • R 9 and R 10 may each independently be a substituted or unsubstituted C 2-8 alkenyl group, or a C 2-4 alkenyl group.
  • m may be 50 to 600 or 100 to 500.
  • the alkyl group and the alkenyl group may be linear or branched.
  • the organopolysiloxane may have an alkenyl group content of 0.05 to 0.2 mmol/g, or 0.1 to 0.2 mmol/g.
  • the alkenyl group may be a vinyl group.
  • the alkenyl group content of the organopolysiloxane is less than 0.05 mmol/g, the cross-linking density of the prepared silicone is lowered, so that the thickener effect is not satisfactory when applied to a cosmetic formulation. is excessively increased, the oil absorption power may be lowered and it may be inferior in terms of usability.
  • the organopolysiloxane may be included in the composition in an amount of 5 to 20 parts by weight, or 10 to 15 parts by weight based on 0.1 to 5 parts by weight of the hydrophilic compound.
  • the content of the organopolysiloxane is less than 5 parts by weight, the crosslinking density of the prepared silicone is lowered and the viscosity is low, and when it is applied to a cosmetic formulation, the thickener effect is unsatisfactory. This drops, the emulsion stability is lowered, and the cross-linking density of the manufactured silicone is excessively increased, resulting in lower oil absorption and inferior feeling in use.
  • the organohydrogenpolysiloxane is a material that cross-reacts with the organopolysiloxane.
  • the organohydrogenpolysiloxane may include a hydrogen group (SiH) directly bonded to silicon in a side chain.
  • the organohydrogenpolysiloxane may be represented by the following formula (3).
  • R 12 to R 20 are a substituted or unsubstituted C 1-10 alkyl group or C 2-10 alkenyl group,
  • a 1 to 50
  • b is 1 to 100;
  • R 12 to R 20 may be a substituted or unsubstituted C 1-6 alkyl group or C 1-3 alkyl group, a may be 1 to 30 or 3 to 20, and b may be 5 to 80 or 10 to 70 .
  • the alkyl group and the alkenyl group may be linear or branched.
  • the content of a hydrogen group (SiH) directly bonded to silicon may be 0.1 to 4.5 mmol/g, or 0.5 to 4.0 mmol/g.
  • SiH content of the organohydrogenpolysiloxane is within the above range, the crosslinking density of the prepared silicone is appropriately adjusted, so that mixing with the diluent is good and a uniform paste can be prepared.
  • the organohydrogenpolysiloxane may have a weight average molecular weight (Mw) of 2,000 to 40,000 g/mol, or 3,000 to 38,000 g/mol.
  • Mw weight average molecular weight
  • the viscosity of the prepared silicone may be appropriate, and the spreadability may be light and less sticky in terms of feeling of use.
  • the organohydrogenpolysiloxane may be included in the composition in an amount of 0.1 to 5 parts by weight, or 1 to 3 parts by weight based on 0.1 to 5 parts by weight of the hydrophilic compound.
  • the content of the organohydrogenpolysiloxane is within the above range, the amount of unreacted substances with the organopolysiloxane is small, and the crosslinking density of the prepared silicone is appropriate, so that the physical properties and feeling of use of the silicone may be good.
  • the polysiloxane composition according to the present invention may further include a diluent.
  • the diluent is not particularly limited as long as it can be added as a diluent to the polysiloxane composition, and for example, an organic solvent, silicone oil, and the like may be mentioned.
  • organic solvent examples include ethanol, isopropanol, sorbitol, maltose, cholesterol, sitosterol, phytosterol, lanosterol, butylene glycol, propylene glycol, dibutylene glycol, and pentyl glycol.
  • the silicone oil is dimethylpolysiloxane, methylphenylpolysiloxane, methylhydrogenpolysiloxane, dimethylsiloxane/methylphenylsiloxane copolymer, organopolysiloxane, octamethylcyclotetrasiloxane (D4), decamethylcyclopentasiloxane (D5), dodecamethyl Cyclohexasiloxane (D6), tetramethyltetrahydrogencyclotetrasiloxane (H4), tetramethyltetraphenylcyclotetrasiloxane, tristrimethylsiloxysilane (M3T), tetrakistrimethylsiloxysilane (M4Q), tristrimethylsiloxy Phenylsilane, steaoxy silicone, alkyl-modified silicone, amino-modified silicone, fluorine-modified silicone, etc. are mentioned.
  • D4
  • the diluent may be included in the composition in an amount of 60 to 95 parts by weight, or 70 to 90 parts by weight based on 0.1 to 5 parts by weight of the hydrophilic compound. If the content of the diluent is less than 60 parts by weight or exceeds 95 parts by weight, a uniform composition may not be obtained, which is not preferable in terms of viscosity or feeling of use of the prepared silicone.
  • the diluent may be added in two divided doses when preparing the hydrophilic silicone, and in this case, the first input amount and the second input amount may be added in a weight ratio of 1: 1.2 to 3.0, or 1: 1.5 to 2.5.
  • the polysiloxane composition according to the present invention may further comprise a catalyst.
  • the catalyst is not particularly limited as long as it can be added to the polysiloxane composition, and for example, a hydrosilylation catalyst, specifically, chloroplatinic acid, platinum metal, platinum supported on alumina, platinum supported on silica, platinum supported on carbon black, platinum-vinylsiloxane complexes, platinum phosphorus complexes, platinum-phosphite complexes, platinum alcoholate catalysts, and the like.
  • a hydrosilylation catalyst specifically, chloroplatinic acid, platinum metal, platinum supported on alumina, platinum supported on silica, platinum supported on carbon black, platinum-vinylsiloxane complexes, platinum phosphorus complexes, platinum-phosphite complexes, platinum alcoholate catalysts, and the like.
  • the catalyst may be included in the composition in an amount of 0.001 to 1 parts by weight, or 0.005 to 0.1 parts by weight based on 0.1 to 5 parts by weight of the hydrophilic compound. If the content of the catalyst is less than 0.001 parts by weight, the reaction may not occur and silicone may not be produced.
  • the polysiloxane composition according to the present invention may include a hydrophilic compound prepared by reacting a polyhydric alcohol compound with a glycidyl compound to prepare a silicone having excellent hydrophilicity.
  • hydrophilic silicone according to the present invention is prepared from the polysiloxane composition.
  • the hydrophilic silicone may have a solid content of 10 to 30% by weight or 10 to 20% by weight based on the total weight, and a viscosity of 50,000 to 600,000 cP or 100,000 to 500,000 cP at 25°C.
  • the hydrophilic silicone according to the present invention has excellent hydrophilicity, emulsion stability, and compatibility, and has little odor, so it can be used as an emulsifier in a cosmetic composition.
  • DMSO dimethyl sulfoxide
  • pentaerythritol a polyhydric alcohol compound
  • KOH potassium hydroxide
  • a reaction vessel 64.99 parts by weight of dimethyl sulfoxide (DMSO), 17.70 parts by weight of pentaerythritol, a polyhydric alcohol compound, and 0.06 parts by weight of potassium hydroxide (KOH) were put in a reaction vessel, and the temperature was raised to 80° C. and maintained for 30 minutes. did. Thereafter, 13.35 parts by weight of a glycidyl compound, 2-(prop-2-enoxymethyl)oxirane (AGE), was added dropwise to react. After completion of the dropwise addition, the reaction was further carried out for 3 hours, 3.90 parts by weight of a neutralizing agent (Kyowa Chemical Industry Co., Ltd., KYOWAAD-600) was added, followed by stirring for 1 hour. Thereafter, it was filtered with a filter paper and distilled under reduced pressure at 120° C. for 3 hours to remove the solvent
  • the prepared hydrophilic compound was represented by the following Chemical Formula 4, and had a weight average molecular weight (Mw) of about 250 g/mol and a hydroxyl group content of 28 ⁇ 2 wt%.
  • a hydrophilic compound was prepared in the same manner as in Preparation Example 1, except that the content of 2-(prop-2-enoxymethyl)oxirane, a glycidyl compound, as a reaction material was adjusted as shown in Table 1.
  • the prepared hydrophilic silicone had a viscosity of 270,000 cP at 25°C, and had a milky white appearance.
  • a silicone was prepared in the same manner as in Example 1, except that the components having the same content as in Tables 2 and 3 were used.
  • Example 1 Example 2
  • Example 3 Example 4
  • Hydrophilic compound of Preparation Example 1 1.93 1.26 1.26 1.26 4.01
  • Hydrophilic compound of Preparation Example 2 - - - - - Hydrophilic compound of Preparation Example 3 - - - - - Organopolysiloxane 11.2 12.42 22.1 12.42 11.2
  • Organohydrogenpolysiloxane 2.45 1.83 1.83 7.40 2.45
  • IPA 10.85 10.85 10.85 10.85 10.85 10.85 10.85 10.85 10.85 10.85 catalyst 0.01 0.01 0.01 0.01 0.01 0.01 0.01 dimethicone 73.56 73.63 63.95 68.06 71.48 total amount 100.00 100.00 100.00 100.00 100.00 100.00 100.00
  • Exterior milky paste milk white paste milk white paste milky paste milk white paste Solid content (wt%) 15.50 15.50 25.20 21.05 17.70 Viscosity at 25°C (cP) 270,000 270,000 75,000 82,000 420,000
  • organo polysiloxane Vinyl group content 0.2 mmol/g, viscosity at 25°C: 400 mPa s, Mw: 10,000 g/mol catalyst PT-VTSC-1.0PS (Platinum and (0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane, Platinum-(0)-1,3-divinyl-1,1,3 ,3-tetramethyldisiloxane) (platinum content: 1% by weight)
  • silicone compounds of Examples and Comparative Examples were prepared as water-in-oil emulsions corresponding to the following formulations, and emulsification performance was evaluated.
  • phase A 3 parts by weight of the silicone compound and 15 parts by weight of decamethylcyclopentasiloxane (D5) were stirred to prepare a phase A. Further, 72.9 parts by weight of ionized water, 8 parts by weight of glycerin, 0.8 parts by weight of sodium chloride, and 0.3 parts by weight of phenoxyethanol were stirred to prepare phase B. Thereafter, a water-in-oil emulsion was prepared by adding the B phase in small amounts while stirring the A phase.
  • D5 decamethylcyclopentasiloxane
  • the evaluation criteria are 5 steps, very good when silicone and ionized water are emulsified without phase separation and dissolves easily in water, excellent when emulsified without phase separation or takes some time to dissolve in water.
  • silicone and ionized water are not partially emulsified, slightly insufficient, and silicone and ionized water remain in a state of not mixing at all. In this case, it was evaluated as very insufficient.
  • OMC octylmethoxyxinnamate
  • Example 1 very good No clumping and oil separation Transparency very good
  • Example 2 very good No clumping and oil separation very transparent very good
  • Example 3 Great No clumping and oil separation Transparency Great
  • Example 4 Great No clumping and oil separation Transparency Great
  • Example 5 Great No clumping and oil separation Transparency commonly Comparative Example 1 lack oil separation opacity lack Comparative Example 2 very lacking oil separation opacity lack Comparative Example 3 lack oil separation opacity lack Comparative Example 4 commonly oil separation opacity lack Comparative Example 5 commonly oil separation opacity lack
  • the silicones of Examples 1 to 5 were excellent in hydrophilicity, stability, compatibility, and feeling of use.
  • the silicones of Comparative Examples 1 to 3 containing a hydrophilic compound prepared using a small amount or an excess of a glycidyl compound, and Comparative Examples 4 and 5 containing a small amount or an excessive amount of the hydrophilic compound lack hydrophilicity and stability. Due to this lack, oil separation occurred, and compatibility and feeling of use were insufficient.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Cosmetics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

La présente invention concerne une composition de polysiloxane et une silicone hydrophile préparée à partir de celle-ci, la composition comprenant un composé hydrophile, un organopolysiloxane, et un organohydrogénopolysiloxane, le composé hydrophile étant préparé par réaction d'un composé glycidylique avec un composé d'alcool polyhydrique dans un rapport pondéral de 1 : 1,0 à 1 : 1,5, et l'organopolysiloxane comprenand un groupe alcényle.
PCT/KR2021/005024 2020-04-21 2021-04-21 Composition de polysiloxane et silicone hydrophile préparée à partir de celle-ci WO2021215825A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020200048340A KR102340546B1 (ko) 2020-04-21 2020-04-21 폴리실록산 조성물 및 이로부터 제조된 친수성 실리콘
KR10-2020-0048340 2020-04-21

Publications (1)

Publication Number Publication Date
WO2021215825A1 true WO2021215825A1 (fr) 2021-10-28

Family

ID=78231507

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2021/005024 WO2021215825A1 (fr) 2020-04-21 2021-04-21 Composition de polysiloxane et silicone hydrophile préparée à partir de celle-ci

Country Status (2)

Country Link
KR (1) KR102340546B1 (fr)
WO (1) WO2021215825A1 (fr)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6265480B1 (en) * 1999-04-14 2001-07-24 Dow Corning Toray Silicone Company, Ltd. Silicone gel composition
KR20140106745A (ko) * 2011-12-27 2014-09-03 다우 코닝 도레이 캄파니 리미티드 동시-개질된 유기폴리실록산, 이를 이용한 유중수 에멀젼용 유화제, 외용 제제, 및 화장 조성물
KR20140127231A (ko) * 2011-12-27 2014-11-03 다우 코닝 도레이 캄파니 리미티드 다이글리세린 유도체-개질된 실리콘, 이를 이용한 유중수 에멀젼용 유화제, 외용 제제, 및 화장 조성물
WO2015162906A1 (fr) * 2014-04-21 2015-10-29 東レ・ダウコーニング株式会社 Procédé de production d'une silicone liquide de haute pureté modifiée par un dérivé de polyol ou d'une composition la contenant
KR102058417B1 (ko) * 2011-12-27 2019-12-24 다우 코닝 도레이 캄파니 리미티드 신규한 액상 오르가노폴리실록산 및 이의 용도

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102648264B (zh) 2009-10-23 2015-08-19 道康宁东丽株式会社 用于基于油的原料的增稠剂或胶凝剂

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6265480B1 (en) * 1999-04-14 2001-07-24 Dow Corning Toray Silicone Company, Ltd. Silicone gel composition
KR20140106745A (ko) * 2011-12-27 2014-09-03 다우 코닝 도레이 캄파니 리미티드 동시-개질된 유기폴리실록산, 이를 이용한 유중수 에멀젼용 유화제, 외용 제제, 및 화장 조성물
KR20140127231A (ko) * 2011-12-27 2014-11-03 다우 코닝 도레이 캄파니 리미티드 다이글리세린 유도체-개질된 실리콘, 이를 이용한 유중수 에멀젼용 유화제, 외용 제제, 및 화장 조성물
KR102058417B1 (ko) * 2011-12-27 2019-12-24 다우 코닝 도레이 캄파니 리미티드 신규한 액상 오르가노폴리실록산 및 이의 용도
WO2015162906A1 (fr) * 2014-04-21 2015-10-29 東レ・ダウコーニング株式会社 Procédé de production d'une silicone liquide de haute pureté modifiée par un dérivé de polyol ou d'une composition la contenant

Also Published As

Publication number Publication date
KR20210130050A (ko) 2021-10-29
KR102340546B1 (ko) 2021-12-20

Similar Documents

Publication Publication Date Title
AU725519B2 (en) Elastomer gels containing volatile, low molecular weight silicones
US5236997A (en) Curable fluorosilicone rubber composition
JP5353357B2 (ja) カルボキシル基を有するオルガノポリシロキサン
US6881416B2 (en) Alkyl group-substituted organopolysiloxane gels
JPH0623255B2 (ja) パーフルオロアルキル基含有オルガノポリシロキサンの製造方法
US6197914B1 (en) Method for preparing polyorganosiloxane resins that contain mono-and tetrafunctional units
JPH02262503A (ja) 印象材組成物
US5059668A (en) Fluorosilicone rubber composition
US5447997A (en) Silicone polyether carboxylic acids
JPH0363994B2 (fr)
JP3212492B2 (ja) シリコーンオイル組成物
WO2021215825A1 (fr) Composition de polysiloxane et silicone hydrophile préparée à partir de celle-ci
EP2966114A1 (fr) Resines de silicone resistantes a la temperature
EP0490523B1 (fr) Compositions de polysiloxanes à un composant durcissables à la chaleur
JP2632607B2 (ja) 硬化性オルガノポリシロキサン組成物
GB2118960A (en) Process for producing fluorosilicone polymers
WO2023195626A1 (fr) Composition de polysiloxane et silicone hydrophile préparée à partir de celle-ci
WO2020184814A1 (fr) Émulsion de silicone et son procédé de production
JP2004231607A (ja) 毛髪化粧料
AU573873B2 (en) Terminal cluster acrylate silicones
US4683320A (en) Novel organopolysiloxane, method for the preparation thereof and composition containing the same
EP2551291B1 (fr) Composé de polysiloxane à modification dihydroxypropylamide
JP3084200B2 (ja) 化粧料
WO2022114490A1 (fr) Composition cosmétique et sa méthode de préparation
JP2850753B2 (ja) シリコーン化合物並びにその製造方法及び化粧料

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 21793806

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 21793806

Country of ref document: EP

Kind code of ref document: A1