WO2023286473A1 - ペースト状シリコーン組成物、その製造方法及び化粧料 - Google Patents
ペースト状シリコーン組成物、その製造方法及び化粧料 Download PDFInfo
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- WO2023286473A1 WO2023286473A1 PCT/JP2022/021861 JP2022021861W WO2023286473A1 WO 2023286473 A1 WO2023286473 A1 WO 2023286473A1 JP 2022021861 W JP2022021861 W JP 2022021861W WO 2023286473 A1 WO2023286473 A1 WO 2023286473A1
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- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
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- DQAKJEWZWDQURW-UHFFFAOYSA-N pyrrolidonecarboxylic acid Chemical compound OC(=O)N1CCCC1=O DQAKJEWZWDQURW-UHFFFAOYSA-N 0.000 description 1
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- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- GSANOGQCVHBHIF-UHFFFAOYSA-N tetradecamethylcycloheptasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 GSANOGQCVHBHIF-UHFFFAOYSA-N 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- BORJONZPSTVSFP-UHFFFAOYSA-N tetradecyl 2-hydroxypropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)C(C)O BORJONZPSTVSFP-UHFFFAOYSA-N 0.000 description 1
- DZKXJUASMGQEMA-UHFFFAOYSA-N tetradecyl tetradecanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCC DZKXJUASMGQEMA-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
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- 239000001069 triethyl citrate Substances 0.000 description 1
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- SCRSFLUHMDMRFP-UHFFFAOYSA-N trimethyl-(methyl-octyl-trimethylsilyloxysilyl)oxysilane Chemical compound CCCCCCCC[Si](C)(O[Si](C)(C)C)O[Si](C)(C)C SCRSFLUHMDMRFP-UHFFFAOYSA-N 0.000 description 1
- 229940118594 trimethylolpropane triisostearate Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
-
- 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
- A61K8/895—Polysiloxanes containing silicon bound to unsaturated aliphatic groups, e.g. vinyl dimethicone
-
- 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
- A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
-
- 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
- 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
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- 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
- 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
- C08L83/14—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/10—General cosmetic use
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/59—Mixtures
- A61K2800/594—Mixtures of polymers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
- A61K2800/805—Corresponding aspects not provided for by any of codes A61K2800/81 - A61K2800/95
Definitions
- the present invention relates to a paste-like silicone composition, its manufacturing method, and cosmetics.
- Organosiloxane polymers having a crosslinked structure have been proposed as methods for stably blending silicone oils, hydrocarbon oils, ester oils, etc. into cosmetics and personal care compositions (Patent Documents 1, 2, 3). This is already a known technique, and an organosiloxane polymer having a crosslinked structure (hereinafter referred to as a silicone crosslinked product) is mainly obtained by a hydrosilylation reaction of an organohydrogenpolysiloxane and an alkenyl group-containing organopolysiloxane, It is blended in cosmetics and personal care compositions in a state of being pre-mixed and pasted with some of the oils used.
- a silicone crosslinked product an organosiloxane polymer having a crosslinked structure
- Organohydrogenpolysiloxanes and alkenyl group-containing organopolysiloxanes are generally made from hydrolyzed dimethylchlorosilane or siloxanes whose main component is a cyclic siloxane oligomer, and are redistributed under strong acid or strong base conditions. Manufactured by reacting.
- plasticity reversion means that the viscosity of the paste-like silicone composition increases over time and the properties change. It is a phenomenon such as changing to This phenomenon is considered to be a physical phenomenon, and although it is possible to restore the original paste state by performing re-mixing or the like, it is undeniable that usability is significantly reduced. Therefore, in order to improve the quality of the paste-like silicone composition, it is necessary to control the amount of highly volatile low-molecular-weight components.
- highly volatile components are mainly those with a molecular weight of less than 300, and it is known that these can be removed by heating under reduced pressure, thin film distillation, steam distillation, fractionation using a column, or the like.
- the oil may also be removed by the above-described treatment, which may change the composition.
- some countries and regions have restricted the use and content of cyclic low-molecular-weight siloxanes. become a matter of concern.
- An object of the present invention is to provide a stable paste-like silicone composition that undergoes little change over time, such as plastic reversion, and has little offensive odor.
- Another object of the present invention is to provide a pasty silicone composition containing a low amount of cyclic low-molecular-weight siloxane components, which is regulated in some countries and regions.
- the present invention provides a paste-like silicone composition
- a paste-like silicone composition comprising the following components (A) and (B), octamethylcyclotetrasiloxane contained in the paste-like silicone composition
- a pasty silicone composition containing less than 2,000 ppm of decamethylcyclopentasiloxane and dodecamethylcyclohexasiloxane.
- the component (A-1) is preferably an organohydrogenpolysiloxane represented by the following general formula (1).
- R 1 is independently a group selected from an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, and an aralkyl group having 7 to 30 carbon atoms
- R 2 is a group independently selected from the above R 1 or a hydrogen atom, provided that two or more R 2 in one molecule are hydrogen atoms and an integer of 3 ⁇ a ⁇ 100,000 and 1 ⁇ b ⁇ 50 is.
- the component (A-2) is preferably an alkenyl group-containing organopolysiloxane represented by the following general formula (2).
- R 1 is independently a group selected from an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, and an aralkyl group having 7 to 30 carbon atoms
- R 3 is independently a group selected from the above R 1 or an alkenyl group having 2 to 10 carbon atoms, provided that two or more R 3 in one molecule are alkenyl groups, and 3 ⁇ c ⁇ 100,000, 0 ⁇ d ⁇ 50 integers.
- a method for producing the paste-like silicone composition wherein the component (A-1) and the component (A-2) are subjected to a hydrosilylation reaction in the presence of a hydrosilylation reaction catalyst, including the step of obtaining the component (A), wherein the content of octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, and dodecamethylcyclohexasiloxane as the component (A-1) and the component (A-2)
- a method for producing a paste-like silicone composition using 2,000 ppm or less of each.
- this method of manufacturing a paste-like silicone composition is preferable.
- the hydrosilylation reaction is preferably carried out in the presence of 0.01 to 100% by mass of component (B) blended in the paste silicone composition.
- the present invention also provides a cosmetic containing the paste silicone composition described above.
- Such cosmetics are eco-friendly cosmetics with good stability and sensuality.
- the present invention it is possible to provide a stable paste-like silicone composition with little change over time, such as plastic reversion, and little offensive odor, by using raw materials with a reduced content of cyclic low-molecular-weight siloxane.
- it is also effective in that it can be used without concern in countries and regions that have recently restricted the use and content of cyclic siloxane.
- this paste-form silicone composition it is possible to provide environmentally friendly cosmetics with excellent stability and functionality.
- the present invention provides a paste-like silicone composition, comprising the following components (A) and (B), wherein octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, and dodecamethylcyclohexasiloxane are each less than 2,000 ppm.
- the paste-like silicone composition of the present invention contains the following components (A) and (B), and contains octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, and dodecamethylcyclohexa Each containing less than 2,000 ppm of siloxane. Each component will be described below.
- the component (A) of the present invention is the following component (A-1) and component (A-2); (A-1) an organohydrogenpolysiloxane having two or more silicon-bonded hydrogen atoms in one molecule, (A-2) an alkenyl group-containing organopolysiloxane having two or more silicon-bonded alkenyl groups having 2 to 10 carbon atoms in one molecule; is a crosslinked organopolysiloxane consisting of a hydrosilylation reactant of In the components (A-1) and (A-2) above, the contents of octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, and dodecamethylcyclohexasiloxane are respectively 2,000 ppm or less, preferably 1,000 ppm or less.
- the structure of the organohydrogenpolysiloxane (A-1) is not particularly limited, it is preferably represented by the following formula (1).
- R 1 is independently a group selected from an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, and an aralkyl group having 7 to 30 carbon atoms
- R 2 is a group independently selected from the above R 1 or a hydrogen atom, provided that two or more R 2 in one molecule are hydrogen atoms and an integer of 3 ⁇ a ⁇ 100,000 and 1 ⁇ b ⁇ 50 is.
- R 1 is a group independently selected from an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, and an aralkyl group having 7 to 30 carbon atoms. and the alkyl group preferably has 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms.
- alkyl groups include chain alkyl groups such as methyl group, ethyl group, propyl group, butyl group, lauryl group, myristyl group, palmityl group and stearyl group, and cycloalkyl groups such as cyclopentyl group and cyclohexyl group. , preferably a methyl group or an ethyl group.
- the aryl group preferably has 6 to 20 carbon atoms, more preferably 6 to 10 carbon atoms.
- Examples of the aryl group include phenyl group, tolyl group, xylyl group and the like, preferably phenyl group.
- the aralkyl group preferably has 7 to 20 carbon atoms, more preferably 7 to 10 carbon atoms. Examples of the aralkyl group include benzyl group and phenethyl group, preferably benzyl group.
- R 2 is a group independently selected from R 1 above or a hydrogen atom, and two or more R 2 in one molecule are hydrogen atoms, preferably 2 or more and 5 or less.
- a is an integer of 3 ⁇ a ⁇ 100,000, preferably 5 ⁇ a ⁇ 1,000, more preferably 10 ⁇ a ⁇ 500.
- alkenyl group-containing organopolysiloxane (A-2) is not particularly limited, it is preferably represented by the following formula (2).
- R 1 is independently a group selected from an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, and an aralkyl group having 7 to 30 carbon atoms
- R 3 is independently a group selected from the above R 1 or an alkenyl group having 2 to 10 carbon atoms, provided that two or more R 3 in one molecule are alkenyl groups, and 3 ⁇ c ⁇ 100,000, 0 ⁇ d ⁇ 50 integers.
- R 1 is as described above
- R 3 is independently a group selected from the above R 1 or an alkenyl group having 2 to 10 carbon atoms, and two One or more R 3 is an alkenyl group.
- alkenyl groups include vinyl, allyl, propenyl, butenyl, pentenyl, and hexenyl groups. It is preferably a group.
- c is an integer of 3 ⁇ c ⁇ 100,000, preferably 5 ⁇ c ⁇ 10,000, more preferably 10 ⁇ c ⁇ 1,000.
- organohydrogenpolysiloxane having only one silicon-bonded hydrogen atom in one molecule or organohydrogenpolysiloxane having only one silicon-bonded alkenyl group in one molecule. It is also possible to use polysiloxane together.
- Component (B) is not particularly limited as long as it is an oil that is liquid at 25°C, but it has a kinematic viscosity of 1.0 to 10,000 mm 2 /s at 25°C in terms of ease of handling when making a paste.
- Liquid oils are preferred, and examples of preferred oils include the following silicone oils, hydrocarbon oils, ester oils, fluorine-based oils, natural animal and vegetable oils, and semi-synthetic oils.
- kinematic viscosity refers to kinematic viscosity at 25° C. according to a method using a Canon-Fenske viscometer described in JIS Z 8803:2011.
- silicone oils include alkyl-modified silicones such as dimethicone (INCI), ethyl methicone (INCI), ethyltrisiloxane (INCI), hexyl dimethicone (INCI), long-chain alkyl-modified silicones such as caprylyl methicone (INCI), phenyl Linear or branched organopolysiloxanes such as trimethicone (INCI), diphenylsiloxyphenyl trimethicone (INCI), diphenyldimethicone (INCI), tetraphenyldimethyldisiloxane (INCI), cyclotetrasiloxane (INCI), cyclopenta cyclic organopolysiloxanes such as siloxane (INCI), cyclohexasiloxane (INCI), cycloheptasiloxane (INCI), tetramethyltetraphenyl
- Hydrocarbon oils include chain and cyclic hydrocarbon oils.
- isoparaffins such as olefin oligomer (INCI), (C13,14) isoparaffin (INCI), isododecane (INCI), undecane (INCI), dodecane (INCI), isohexadecane (INCI), hydrogenated polyisobutene (INCI) : Hydrogenated Polyisobutene), squalane (INCI), mineral oil (INCI), coconut alkanes (INCI), (C13-15) alkanes such as (INCI), and the like.
- isoparaffins such as olefin oligomer (INCI), (C13,14) isoparaffin (INCI), isododecane (INCI), undecane (INCI), dodecane (INCI), isohexadecane (INCI), hydrogenated polyisobutene (INCI) : Hydrogenated Polyisobutene), squa
- ester oils include diisobutyl adipate (INCI: Diisobutyl Adipate), dihexyldecyl adipate (display name), diheptylundecyl adipate (INCI: Diheptylundecyl Adipate), isostearyl isostearate (INCI: Isostearate), isostearic acid Alkyl glycol monoisostearate such as isocetyl (INCI), trimethylolpropane triisostearate (INCI), glycol diethylhexanoate (INCI), cetyl ethylhexanoate (INCI), ⁇ (INCI:Trimethylolpropane Triethylhexanoate) ⁇ (INCI:Pentaerythrityl Tetraethylhexanoate) ⁇ (INCI:Cetyl Ethylhexanoate) ⁇ (INCI:Octyldode
- glyceride oils include triethylhexanoin (INCI), caprylic/capric triglyceride (INCI: caprylic/capric triglyceride), cocoglyceryl (INCI), caprylic/capric /succinic acid) triglyceride (INCI: Caprylic/Capric/Succinic Triglyceride), (caprylic/capric acid) glycerides (INCI), and the like.
- fluorine-based oils examples include perfluoropolyether, perfluorodecalin, and perfluorooctane.
- avocado oil (INCI: Persea Gratissima (Avocado) Oil), linseed oil (INCI: Linum Usitatissimum (Linseed) Seed Oil), almond oil (INCI: Prunus Amygdalus Dulcis (Sweet Almond) ) oil), perilla oil (indicated name), olive oil (INCI: Olea Europaea (Olive) Fruit Oil), American guava oil (INCI: Torreya California (California Nutmeg) Oil), Cymbopogon Nardull (Citadel) Oil) ), kaya seed oil (INCI: Torreya Nucifera Seed Oil), Kyonin oil (INCI: Kyonin Yu), sesame oil (INCI: Sesamum Indicum (Sesame) Seed Oil), rice bran oil (INCI: Oryza Sativa (Rice) Bran Oil), Samantha oil (INCI: Persea Gratissima (Avocad
- the above oils may be used alone or in combination.
- silicone oil, hydrocarbon oil, or ester oil is preferably used, and silicone oil or hydrocarbon oil is particularly preferred.
- the blending amount of component (B) varies depending on component (A), but is preferably 1 to 98% by mass, more preferably 10 to 95% by mass of the silicone paste composition.
- octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, and dodecamethylcyclohexasiloxane contained in the silicone paste composition of the present invention are each less than 2000 ppm, preferably less than 1500 ppm, and more preferably less than 1000 ppm. , more preferably less than 100 ppm. If any of the above cyclic siloxanes is 2000 ppm or more, there is a concern that it cannot be used in countries and regions that regulate the use and content of cyclic low-molecular-weight siloxanes.
- Cosmetics containing the paste-form silicone composition of the present invention include emulsions, creams, cleansers, packs, massage agents, serums, beauty oils, cleansers, deodorants, hand creams, lip balms, wrinkle concealers, and the like.
- Skin care cosmetics makeup base, concealer, white powder, liquid foundation, oily foundation, blusher, eyeshadow, mascara, eyeliner, eyebrow, lipstick and other makeup cosmetics, shampoo, rinse, treatment, hair setting agents, etc.
- Cosmetics, sunscreen oils, sunscreen milky lotions, sunscreen creams and other UV protective cosmetics, and antiperspirants are examples of sunscreen oils, sunscreen milky lotions, sunscreen creams and other UV protective cosmetics, and antiperspirants.
- shapes of these cosmetics include various shapes such as liquid, emulsion, cream, solid, paste, gel, powder, press, multilayer, mousse, spray, and stick. can be selected.
- the forms of these cosmetics include various forms such as aqueous, oily, water-in-oil emulsions, oil-in-water emulsions, non-aqueous emulsions, and multi-emulsions such as W/O/W and O/W/O. can be selected.
- the paste-form silicone composition of the present invention is used in applications such as sealants, coating agents, greases, adhesives, antifoaming agents, pharmaceuticals, insecticides and herbicides. It can also be used to adjust viscosity and improve rheological properties.
- the method for producing the paste-like silicone composition of the present invention comprises subjecting the component (A-1) and the component (A-2) to a hydrosilylation reaction in the presence of a hydrosilylation reaction catalyst to produce the component (A). wherein the contents of octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, and dodecamethylcyclohexasiloxane are each 2,000 ppm or less as the component (A-1) and the component (A-2). It is not particularly limited as long as it is a manufacturing method using a material.
- the above component (A) obtained in the step of obtaining the component (A) and the above component (B) are kneaded by a conventional method to produce a silicone paste A composition can be obtained.
- a conventional method to produce a silicone paste A composition
- the discomfort can be reduced. odor and plasticity reversion can be suppressed.
- the method for producing the organohydrogenpolysiloxane (A-1) or the alkenyl group-containing organopolysiloxane (A-2) is not particularly limited. It is obtained by using siloxanes mainly composed of cyclic and/or acyclic siloxane oligomers cracked in the presence of an alkali catalyst such as potassium hydroxide and performing an equilibration reaction in the presence of an acid catalyst or an alkali catalyst.
- an alkali catalyst such as potassium hydroxide
- Octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, and dodecamethylcyclohexasiloxane can each be reduced to 2,000 ppm or less by subjecting the obtained polysiloxane to a treatment such as stripping under reduced pressure.
- the reaction between the component organohydrogenpolysiloxane (A-1) and the alkenyl group-containing organopolysiloxane (A-2) can be carried out by a hydrosilylation reaction in the presence of a hydrosilylation reaction catalyst.
- Component (A) is thus produced.
- the hydrosilylation reaction catalyst is not particularly limited, but for example, the presence of a hydrosilylation reaction catalyst such as a platinum compound such as chloroplatinic acid, alcohol-modified chloroplatinic acid, chloroplatinic acid-vinylsiloxane complex, or a rhodium compound.
- the organohydrogenpolysiloxane (A-1) and the alkenyl group-containing organopolysiloxane (A-2) may be reacted below.
- the reaction temperature is not particularly limited, but it is preferably 40 to 120°C.
- the amount of the hydrosilylation reaction catalyst to be added may be a well-known effective amount. 500 ppm, preferably 0.5-200 ppm, more preferably 1-100 ppm.
- the molar ratio of all alkenyl groups/total hydrosilyl groups is not particularly limited, but is preferably 1/10 to 10/1, more preferably 8/10 to 3/1. be.
- the above hydrosilylation reaction may be carried out without a solvent, or an organic solvent or volatile dimethylsilicone may be used as necessary.
- organic solvents include aliphatic alcohols such as methanol, ethanol, 2-propanol and butanol; aromatic hydrocarbons such as benzene, toluene and xylene; Cyclic hydrocarbons; halogenated hydrocarbons such as dichloromethane, chloroform and carbon tetrachloride; ketone solvents such as acetone and methyl ethyl ketone; Among them, solvent-free ethanol or 2-propanol is preferable from the viewpoint of use in cosmetics.
- volatile dimethylsilicone examples include dimethylpolysiloxane having a kinematic viscosity of 5 mm 2 /s or less. These organic solvents and volatile dimethylsilicone can be removed by heating under reduced pressure after the reaction, if necessary. Moreover, this method may be carried out in the presence of a liquid oil component (B), and since no other solvent is used, this method is most preferable in terms of usability and production.
- the amount of component (B) blended in the paste-like silicone composition of the present invention is preferably 0.01 to 100% by mass, more preferably 0.1 to 90% by mass. preferable.
- the hydrosilylation reaction can be carried out in the presence of 0.01 to 100% by mass of component (B) blended in the paste silicone composition.
- Cyclic siloxane content 0.5 g of the sample was mixed with 10 ml of acetone containing 20 mass ppm of tetradecane as an internal standard (shaking for 6 hours), centrifuged, and the acetone layer was collected and analyzed by gas chromatography. and quantified each cyclic siloxane component. The results are listed in Table 1.
- - Consistency Measured according to the method described in JIS K 2220:2013.
- ⁇ Absolute viscosity Measured by a method using a B-type rotational viscometer (apparatus name: TVB-10M type viscometer manufactured by Toki Sangyo Co., Ltd.) described in JIS K 7117-1:1999.
- ⁇ Kinematic viscosity Measured at 25°C by the method using a Canon-Fenske viscometer described in JIS Z 8803:2011.
- Offensive odor The odor was sensory evaluated by 9 panelists, and the result with the most responses in the following judgment criteria was described.
- Absent, (2) Slightly, (3) Reverted to plasticity The properties and the properties the next day were confirmed visually and by hand-mixing with a spatula, and described in the following expressions.
- Example 1 In a reaction vessel, 40.9 parts by mass of organohydrogenpolysiloxane (1) listed in Table 1 below and 10.8 parts by mass of alkenyl group-containing organopolysiloxane (6) listed in Table 1 below were added at 25°C. 51.8 parts by mass of dimethylsiloxane (kinetic viscosity of 2 mm 2 /s) as a liquid oil agent and 0.02 parts by mass of a divinyltetramethyldisiloxane solution containing 1% by mass of chloroplatinic acid as a hydrosilylation reaction catalyst were added, and 70 parts by mass were added. The reaction was allowed to proceed at ⁇ 80°C for 2 hours.
- organohydrogenpolysiloxane (1) listed in Table 1 below 10.8 parts by mass of alkenyl group-containing organopolysiloxane (6) listed in Table 1 below were added at 25°C. 51.8 parts by mass of dimethylsiloxane (kinetic viscosity of 2 mm 2
- a smooth paste-like silicone composition with a consistency of 270 was obtained. There was no offensive odor, and the properties on the next day were unchanged.
- the content of octamethylcyclotetrasiloxane and decamethylcyclopentasiloxane in the paste silicone composition was less than 100 ppm, respectively, and the content of dodecamethylcyclohexasiloxane was 100 ppm.
- Example 2 In a reaction vessel, 40.9 parts by mass of the organohydrogenpolysiloxane (1) listed in Table 1 below and 10.0 parts by mass of the alkenyl group-containing organopolysiloxane (7) listed in Table 1 below were added at 25°C. 50.9 parts by mass of dimethylsiloxane (kinetic viscosity of 2 mm 2 /s) as a liquid oil agent and 0.02 parts by mass of a divinyltetramethyldisiloxane solution containing 1% by mass of chloroplatinic acid as a hydrosilylation reaction catalyst were added. The reaction was allowed to proceed at ⁇ 80°C for 2 hours.
- organohydrogenpolysiloxane (1) listed in Table 1 below 10.0 parts by mass of the alkenyl group-containing organopolysiloxane (7) listed in Table 1 below were added at 25°C. 50.9 parts by mass of dimethylsiloxane (kinetic viscosity of 2 mm 2 /s) as
- a smooth paste-like silicone composition with a consistency of 273 was obtained at a weight ratio of 80. There was no offensive odor, and the properties on the next day were unchanged.
- the content of octamethylcyclotetrasiloxane and decamethylcyclopentasiloxane in the paste silicone composition was less than 100 ppm, respectively, and the content of dodecamethylcyclohexasiloxane was 180 ppm.
- Example 3 In a reaction vessel, 8.0 parts by mass of organohydrogenpolysiloxane (3) listed in Table 1 below, 96.5 parts by mass of alkenyl group-containing organopolysiloxane (9) listed in Table 1 below, and hydrosilylation were added. As a reaction catalyst, 0.03 parts by mass of a divinyltetramethyldisiloxane solution containing 1% by mass of chloroplatinic acid was added and reacted at 70 to 80° C. for 2 hours.
- Example 4 In a reaction vessel, 7.2 parts by mass of the organohydrogenpolysiloxane (5) listed in Table 1 below and 21.5 parts by mass of the alkenyl group-containing organopolysiloxane (9) listed in Table 1 below were added at 25°C. 114.6 parts by mass of diphenylsiloxyphenyl trimethicone (display name: KF-56A manufactured by Shin-Etsu Chemical Co., Ltd.) as a liquid oil, and 1% by mass of chloroplatinic acid divinyltetramethyl dimethicone as a hydrosilylation reaction catalyst. 0.02 part by mass of a siloxane solution was added and reacted at 70 to 80° C. for 2 hours.
- organohydrogenpolysiloxane (5) listed in Table 1 below 21.5 parts by mass of the alkenyl group-containing organopolysiloxane (9) listed in Table 1 below were added at 25°C. 114.6 parts by mass of diphenyl
- Example 5 In a reaction vessel, 8.6 parts by mass of organohydrogenpolysiloxane (4) listed in Table 1 below, 103.1 parts by mass of alkenyl group-containing organopolysiloxane (10) listed in Table 1 below, and hydrosilylation were added. As a reaction catalyst, 0.03 parts by mass of a divinyltetramethyldisiloxane solution containing 1% by mass of chloroplatinic acid was added and reacted at 70 to 80° C. for 2 hours.
- Comparative example 1 In a reaction vessel, 45.2 parts by mass of the organohydrogenpolysiloxane (2) listed in Table 1 below and 11.0 parts by mass of the alkenyl group-containing organopolysiloxane (8) listed in Table 1 below were added at 25°C. 56.3 parts by mass of dimethylsiloxane (kinetic viscosity of 2 mm 2 /s) as a liquid oil agent and 0.02 parts by mass of a divinyltetramethyldisiloxane solution containing 1% by mass of chloroplatinic acid as a catalyst for hydrosilylation reaction were added. The reaction was allowed to proceed at ⁇ 80°C for 2 hours.
- organohydrogenpolysiloxane (2) listed in Table 1 below 11.0 parts by mass of the alkenyl group-containing organopolysiloxane (8) listed in Table 1 below were added at 25°C. 56.3 parts by mass of dimethylsiloxane (kinetic viscosity of 2 mm 2 /s
- the content of octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane and dodecamethylcyclohexasiloxane in the paste silicone composition was 170 ppm, 2800 ppm and 1900 ppm, respectively.
- organopolysiloxanes used in Examples 1 to 5 and Comparative Example 1 are shown in Table 1 below, and the results of Examples 1 to 5 and Comparative Example 1 are shown in Table 2 below.
- Organopolysiloxanes (1) to (10) were used as samples for determining the cyclic siloxane content.
- D4 Octamethylcyclotetrasiloxane
- D5 Decamethylcyclopentasiloxane
- D6 Dodecamethylcyclohexasiloxane
- the paste-like silicone composition of the present invention was a stable paste-like silicone composition with little change over time, such as plastic reversion, and little offensive odor.
- Examples 1 to 4 had no offensive odor.
- Comparative Example 1 which is a paste-like silicone composition in which the content of any one of octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, and dodecamethylcyclohexasiloxane exceeded 2,000 ppm, plastic reversion and other problems occurred over time. There was a change, there was a strange smell, and a stable paste-like silicone composition was not obtained.
- the present invention is not limited to the above embodiments.
- the above-described embodiment is an example, and any device having substantially the same configuration as the technical idea described in the claims of the present invention and exhibiting the same effect is the present invention. included in the technical scope of
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Abstract
Description
ここで、可塑戻りとは、経時でペースト状シリコーン組成物の粘度が増加し、性状が変化することであり、具体的には、なめらかで流動性のある液状ペーストが、流動性のないゼリー状に変化する等の現象である。この現象は物理現象と考えられ、再混合等を行うことにより元のペースト状態に戻すことが可能であるが、使用性が著しく低下することは否めない。よって、ペースト状シリコーン組成物の品質向上のためには、揮発性の高い低分子成分量を管理する必要がある。
また、近年、特に環状の低分子シロキサンに関して使用や含有量を規制する国や地域もあるため、これらの地域においても、低分子シロキサンが高含有率で残存していることは、使用する上で懸念材料となる。
(A):下記成分(A-1)と成分(A-2);
(A-1)1分子中にケイ素原子に結合した水素原子を2個以上有するオルガノハイドロジェンポリシロキサン、
(A-2)1分子中にケイ素原子に結合した炭素数2~10のアルケニル基を2個以上有するアルケニル基含有オルガノポリシロキサン、
のヒドロシリル化反応物からなる架橋型オルガノポリシロキサン、
(B):25℃で液状の油剤
(A):下記成分(A-1)と成分(A-2);
(A-1)1分子中にケイ素原子に結合した水素原子を2個以上有するオルガノハイドロジェンポリシロキサン、
(A-2)1分子中にケイ素原子に結合した炭素数2~10のアルケニル基を2個以上有するアルケニル基含有オルガノポリシロキサン、
のヒドロシリル化反応物からなる架橋型オルガノポリシロキサン、
(B):25℃で液状の油剤
本発明のペースト状シリコーン組成物は、下記成分(A)および成分(B)を含み、前記ペースト状シリコーン組成物中に含まれるオクタメチルシクロテトラシロキサン、デカメチルシクロペンタシロキサン、及びドデカメチルシクロヘキサシロキサンがそれぞれ2,000ppm未満のものである。以下各成分について説明する。
本発明の成分(A)は、下記成分(A-1)と成分(A-2);
(A-1)1分子中にケイ素原子に結合した水素原子を2個以上有するオルガノハイドロジェンポリシロキサン、
(A-2)1分子中にケイ素原子に結合した炭素数2~10のアルケニル基を2個以上有するアルケニル基含有オルガノポリシロキサン、
のヒドロシリル化反応物からなる架橋型オルガノポリシロキサンである。
また、上記成分(A-1)並びに成分(A-2)において、オクタメチルシクロテトラシロキサン、デカメチルシクロペンタシロキサン、及びドデカメチルシクロヘキサシロキサンの含有量がそれぞれ2,000ppm以下、好ましくは1,000ppm以下であるオルガノポリシロキサンであることが好ましい。上記成分(A-1)並びに成分(A-2)において、オクタメチルシクロテトラシロキサン、デカメチルシクロペンタシロキサン、及びドデカメチルシクロヘキサシロキサンの含有量は低ければ低いほど好ましく、下限値は特に決められないが例えば0ppmとすることができる。
上記アラルキル基は、好ましくは炭素数7~20、より好ましくは炭素数7~10のアラルキル基である。アラルキル基の例としては、ベンジル基、フェネチル基などが挙げられ、好ましくはベンジル基である。
成分(B)は、25℃で液状の油剤であれば特に限定されないが、ペースト化の際の取り扱い性が良い点で、25℃における動粘度が1.0~10,000mm2/sである液状の油剤が好ましく、好ましい油剤としては、以下のシリコーン油、炭化水素油、エステル油、フッ素系油剤、天然動植物油、半合成油があげられる。なお、本明細書中で動粘度とは、JIS Z 8803:2011に記載のキャノン-フェンスケ粘度計を用いた方法による25℃での動粘度を指すものとする。
また、本発明におけるペースト状シリコーン組成物を含む化粧料としては、乳液、クリーム、クレンジング、パック、マッサージ料、美容液、美容オイル、洗浄剤、脱臭剤、ハンドクリーム、リップクリーム、しわ隠し等のスキンケア化粧料、メークアップ下地、コンシーラー、白粉、リキッドファンデーション、油性ファンデーション、頬紅、アイシャドウ、マスカラ、アイライナー、アイブロウ、口紅等のメークアップ化粧料、シャンプ-、リンス、トリートメント、セット剤等の毛髪化粧料、日焼け止めオイルや日焼け止め乳液、日焼け止めクリームなどの紫外線防御化粧料、制汗剤等が挙げられる。
本発明のペースト状シリコーン組成物の製造方法は、前記成分(A-1)と前記成分(A-2)をヒドロシリル化反応用触媒存在下でヒドロシリル化反応を行って、前記成分(A)を得る工程を含み、前記成分(A-1)並びに前記成分(A-2)として、オクタメチルシクロテトラシロキサン、デカメチルシクロペンタシロキサン、及びドデカメチルシクロヘキサシロキサンの含有量がそれぞれ2,000ppm以下のものを用いる製造方法であれば、特に限定されず、例えば、前記成分(A)を得る工程により得られる上記成分(A)と上記成分(B)を常法により混錬することによってペースト状シリコーン組成物を得ることができる。架橋物の原料となるオルガノハイドロジェンポリシロキサンやアルケニル基含有オルガノポリシロキサン中に残存するオクタメチルシクロテトラシロキサン、デカメチルシクロペンタシロキサン、及びドデカメチルシクロヘキサシロキサンの量を予め低減することで、不快な臭気や可塑戻りを抑制することができる。
上記オルガノハイドロジェンポリシロキサン(A-1)や、アルケニル基含有オルガノポリシロキサン(A-2)の製造方法は、特に限定されないが、一般には、ジメチルジクロルシランの加水分解、或いは更にこの加水分解物を水酸化カリウム等のアルカリ触媒存在下でクラッキングした環状及び/または非環状シロキサンオリゴマーを主成分とするシロキサン類を原料とし、酸触媒やアルカリ触媒下で平衡化反応を行うことで得られる。得られたポリシロキサンに減圧ストリッピング等の処理を施すことで、オクタメチルシクロテトラシロキサン、デカメチルシクロペンタシロキサン、及びドデカメチルシクロヘキサシロキサンをそれぞれ2,000ppm以下に低減させることができる。
構成要素であるオルガノハイドロジェンポリシロキサン(A-1)と、アルケニル基含有オルガノポリシロキサン(A-2)の反応は、ヒドロシリル化反応用触媒存在下でヒドロシリル化反応により行うことができる。これにより成分(A)が製造される。ヒドロシリル化反応用触媒としては、特に制限はないが、例えば、塩化白金酸、アルコール変性塩化白金酸、塩化白金酸-ビニルシロキサン錯体等の白金化合物、又はロジウム化合物等のヒドロシリル化反応用触媒の存在下で、(A-1)のオルガノハイドロジェンポリシロキサンと、(A-2)のアルケニル基含有オルガノポリシロキサンを反応させればよい。この際、反応温度は特に限定されないが、40~120℃であることが好ましい。前記ヒドロシリル化反応用触媒の添加量は周知の有効量でよく、上記(A-1)及び(A-2)の合計量に対して、白金族金属の換算量で、通常、0.1~500ppm、好ましくは0.5~200ppm、より好ましくは、1~100ppmである。また、このヒドロシリル化反応において、全アルケニル基/全ヒドロシリル基のモル比は、特に限定されないが、好ましくは、1/10~10/1であり、より好ましくは、8/10~3/1である。
・稠度:JIS K 2220:2013に記載の方法に準じて測定した。
・絶対粘度:JIS K 7117-1:1999に記載のB型回転粘度計(装置名:東機産業社製TVB-10M型粘度計)を用いた方法によって測定した。
・動粘度:JIS Z 8803:2011に記載のキャノン-フェンスケ粘度計を用いた方法により25℃で測定した。
・異臭:臭気を9人のパネラーによる官能評価を行い、下記判断基準において最も回答の多い結果を記載した。
(1)なし、(2)ややあり、(3)あり
・可塑戻り:性状,翌日の性状を目視および、ヘラによる手混ぜ撹拌で状態を確認し、下記の表現にて記載した。
(1)なし、(2)ややあり、(3)あり
反応容器に、下記表1に記載の(1)のオルガノハイドロジェンポリシロキサン40.9質量部、下記表1に記載の(6)のアルケニル基含有オルガノポリシロキサン10.8質量部、25℃で液状の油剤としてジメチルシロキサン(動粘度2mm2/s)51.8質量部、及びヒドロシリル化反応用触媒として、塩化白金酸1質量%のジビニルテトラメチルジシロキサン溶液0.02質量部を加え、70~80℃にて2時間反応させた。
反応容器に、下記表1に記載の(1)のオルガノハイドロジェンポリシロキサン40.9質量部、下記表1に記載の(7)のアルケニル基含有オルガノポリシロキサン10.0質量部、25℃で液状の油剤としてジメチルシロキサン(動粘度2mm2/s)50.9質量部、及びヒドロシリル化反応用触媒として、塩化白金酸1質量%のジビニルテトラメチルジシロキサン溶液0.02質量部を加え、70~80℃にて2時間反応させた。
反応容器に、下記表1に記載の(3)のオルガノハイドロジェンポリシロキサン8.0質量部、下記表1に記載の(9)のアルケニル基含有オルガノポリシロキサン96.5質量部、およびヒドロシリル化反応用触媒として、塩化白金酸1質量%のジビニルテトラメチルジシロキサン溶液0.03質量部を加え、70~80℃にて2時間反応させた。
反応容器に、下記表1に記載の(5)のオルガノハイドロジェンポリシロキサン7.2質量部、下記表1に記載の(9)のアルケニル基含有オルガノポリシロキサン21.5質量部、25℃で液状の油剤としてジフェニルシロキシフェニルトリメチコン(表示名称;信越化学工業(株)社製 KF-56A)114.6質量部、およびヒドロシリル化反応用触媒として、塩化白金酸1質量%のジビニルテトラメチルジシロキサン溶液0.02質量部を加え、70~80℃にて2時間反応させた。
反応容器に、下記表1に記載の(4)のオルガノハイドロジェンポリシロキサン8.6質量部、下記表1に記載の(10)のアルケニル基含有オルガノポリシロキサン103.1質量部、およびヒドロシリル化反応用触媒として、塩化白金酸1質量%のジビニルテトラメチルジシロキサン溶液0.03質量部を加え、70~80℃にて2時間反応させた。
反応容器に、下記表1に記載の(2)のオルガノハイドロジェンポリシロキサン45.2質量部、下記表1に記載の(8)のアルケニル基含有オルガノポリシロキサン11.0質量部、25℃で液状の油剤としてジメチルシロキサン(動粘度2mm2/s)56.3質量部、及びヒドロシリル化反応用触媒として、塩化白金酸1質量%のジビニルテトラメチルジシロキサン溶液0.02質量部を加え、70~80℃にて2時間反応させた。
D4:オクタメチルシクロテトラシロキサン
D5:デカメチルシクロペンタシロキサン
D6:ドデカメチルシクロヘキサシロキサン
D4:オクタメチルシクロテトラシロキサン
D5:デカメチルシクロペンタシロキサン
D6:ドデカメチルシクロヘキサシロキサン
Claims (7)
- ペースト状シリコーン組成物であって、下記成分(A)および成分(B)を含み、前記ペースト状シリコーン組成物中に含まれるオクタメチルシクロテトラシロキサン、デカメチルシクロペンタシロキサン、及びドデカメチルシクロヘキサシロキサンがそれぞれ2,000ppm未満のものであることを特徴とするペースト状シリコーン組成物。
(A):下記成分(A-1)と成分(A-2);
(A-1)1分子中にケイ素原子に結合した水素原子を2個以上有するオルガノハイドロジェンポリシロキサン、
(A-2)1分子中にケイ素原子に結合した炭素数2~10のアルケニル基を2個以上有するアルケニル基含有オルガノポリシロキサン、
のヒドロシリル化反応物からなる架橋型オルガノポリシロキサン、
(B):25℃で液状の油剤 - 前記一般式(2)において、d=0であることを特徴とする請求項3に記載のペースト状シリコーン組成物。
- 請求項1から請求項4のいずれか1項に記載のペースト状シリコーン組成物の製造方法であって、前記成分(A-1)と前記成分(A-2)をヒドロシリル化反応用触媒存在下でヒドロシリル化反応を行って、前記成分(A)を得る工程を含み、前記成分(A-1)並びに前記成分(A-2)として、オクタメチルシクロテトラシロキサン、デカメチルシクロペンタシロキサン、及びドデカメチルシクロヘキサシロキサンの含有量がそれぞれ2,000ppm以下のものを用いることを特徴とするペースト状シリコーン組成物の製造方法。
- 請求項5に記載のペースト状シリコーン組成物の製造方法において、前記ヒドロシリル化反応を、前記ペースト状シリコーン組成物に配合される成分(B)の配合量の0.01~100質量%の存在下で行うことを特徴とするペースト状シリコーン組成物の製造方法。
- 請求項1から請求項4のいずれか1項に記載のペースト状シリコーン組成物を含むものであることを特徴とする化粧料。
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- 2022-05-30 EP EP22841820.8A patent/EP4372054A1/en active Pending
- 2022-05-30 CN CN202280047083.2A patent/CN117597400A/zh active Pending
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