WO2022138482A1 - Composition d'émulsion de type huile dans l'eau contenant un polymère - Google Patents

Composition d'émulsion de type huile dans l'eau contenant un polymère Download PDF

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WO2022138482A1
WO2022138482A1 PCT/JP2021/046706 JP2021046706W WO2022138482A1 WO 2022138482 A1 WO2022138482 A1 WO 2022138482A1 JP 2021046706 W JP2021046706 W JP 2021046706W WO 2022138482 A1 WO2022138482 A1 WO 2022138482A1
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polymer
water
mass
composition
aqueous solution
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Japanese (ja)
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真喜子 宮本
博史 山口
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住友精化株式会社
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/04—Acids, Metal salts or ammonium salts thereof
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C08K3/36—Silica
    • 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
    • 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
    • C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C08L101/12—Compositions of unspecified macromolecular compounds characterised by physical features, e.g. anisotropy, viscosity or electrical conductivity
    • C08L101/14—Compositions of unspecified macromolecular compounds characterised by physical features, e.g. anisotropy, viscosity or electrical conductivity the macromolecular compounds being water soluble or water swellable, e.g. aqueous gels

Definitions

  • the present disclosure relates to an O / W type emulsion composition containing a polymer and the like.
  • the contents of all documents described in this specification are incorporated herein by reference.
  • the O / W type emulsion composition is applied to various fields. For example, it is applied to the fields of adhesives and cosmetics.
  • an O / W type emulsion composition As, for example, a cosmetic composition, its stability is important. If the stability is poor, the active ingredient contained in the oil phase may be separated, and the effect may not be exhibited efficiently. In addition, the separation also deteriorates the appearance.
  • sunscreen compositions are O / W emulsion compositions that contain various active ingredients (eg, moisturizers and UV absorbers) and are less stable. The active ingredient separates.
  • active ingredients eg, moisturizers and UV absorbers
  • the present inventors have proceeded with studies for the development of a technique for further enhancing the emulsion stability of the O / W type emulsion composition.
  • the present inventors have conventionally developed O / by using a specific polymer (water-absorbent resin) and mixing each component in a specific order in the production of an O / W type emulsion composition.
  • a specific polymer water-absorbent resin
  • An O / W type emulsion composition containing a water-absorbent polymer has the following conditions (A), (B), and (C): (A): The particle size after water swelling is 100 to 600 ⁇ m (B): At least one of the following (B-1) and (B-2) is satisfied (B-1): 1% by mass aqueous solution of polymer.
  • compositions Item 2. Item 2. The composition according to Item 1, further comprising an organic UV protection agent. Item 3. Item 2. The composition according to Item 2, wherein the organic UV protection agent is a lipophilic organic UV protection agent. Item 4. Item 2. The composition according to any one of Items 1 to 3, wherein the water-absorbent polymer is a polymer obtained by polymerizing a water-soluble unsaturated carboxylic acid monomer (preferably (meth) acrylic acid) in the presence of a cross-linking agent. thing. Item 5. Item 4.
  • composition according to Item 4 wherein the cross-linking agent is at least one selected from the group consisting of water-soluble sucrose allyl ether, ethylene glycol diglycidyl ether, and pentaerythritol allyl ether.
  • the cross-linking agent is at least one selected from the group consisting of water-soluble sucrose allyl ether, ethylene glycol diglycidyl ether, and pentaerythritol allyl ether.
  • an O / W type emulsion composition having high stability and suppressed component separation.
  • an O / W type emulsion composition when used as a cosmetic composition, generally, oil components such as moisturizing components and ultraviolet absorbers contained in the composition can cause sliminess at the time of application, whereas those with poor emulsification are used. It is easier to get slimy than a stable one.
  • the O / W type emulsion composition provided by the present disclosure has high stability and suppresses component separation, so that the sliminess is reduced and therefore the tactile sensation is improved. Therefore, it is particularly suitable for use as an external composition such as a cosmetic composition.
  • the steady flow viscosity was measured in the range of shear rate 0.000001 to 1,000 s -1 using a rheometer, and the graph of the shear rate in the range of 0.1 to 1,000 s-1 is shown.
  • Polymer A: y 126.01x -0.736
  • Polymer B: y 110.39x -0.697
  • Polymer C: y 50.755x -0.66
  • Stress (Pa) and strain (%) when the steady flow viscosity is measured in the range of shear rate 0.000001 to 1,000s -1 using a rheometer is shown.
  • Polymer C: 15.7Pa, 2.8% The outline of the example manufacturing method and the comparative example manufacturing method is shown.
  • the present disclosure preferably includes, but is not limited to, O / W type emulsion compositions and their uses, methods for producing them, and the like, and the present disclosure is all disclosed herein and recognized by those skilled in the art. Including.
  • the O / W emulsion composition included in the present disclosure contains a specific water-absorbent polymer, and when 100 g of the composition is centrifuged at 2000 rpm at 25 ° C. for 10 minutes, the amount of the separated liquid is less than 3 g. It is a composition.
  • the O / W type emulsion composition included in the present disclosure may be referred to as "the composition of the present disclosure”.
  • the amount of the separated liquid in the first half is preferably 2.5 g or less, 2 g or less, 1.5 g or less, 1 g or less, or 0.5 g or less.
  • the specific water-absorbent polymer contained in the composition of the present disclosure is a polymer satisfying the following conditions (A), (B), and (C).
  • the specific water-absorbent polymer may be referred to as "the polymer of the present disclosure".
  • the polymer of the present disclosure is a polymer having a particle size of 100 to 600 ⁇ m when it absorbs water and swells.
  • (A) defines the particle size of the swollen water-absorbent polymer in the composition of the present disclosure. It can be said that it is doing.
  • the upper or lower limit of the particle size range (100 to 600 ⁇ m) when water is absorbed and swollen is, for example, 110, 120, 130, 140, 150, 160, 170, 180, 190, 200, 210, 220. , 230, 240, 250, 260, 270, 280, 290, 300, 310, 320, 330, 340, 350, 360, 370, 380, 390, 400, 410, 420, 430, 440, 450, 460, 470. It may be 480, 490, 500, 510, 520, 530, 540, 550, 560, 570, 580, or 590 ⁇ m.
  • the range may be 110 to 590 ⁇ m.
  • the particle size is a medium particle size having a volume average particle size measured by a laser diffraction method.
  • a measuring device laser diffraction type particle size distribution measuring device
  • SALD-2300 manufactured by Shimadzu Corporation
  • the polymer of the present disclosure satisfies at least one of (B-1) and (B-2). That is, the polymer of the present disclosure satisfies at least one of the conditions (B-1) or (B-2), and preferably both of these conditions.
  • These conditions can be measured (and calculated) by measuring the steady flow viscosity of the 1% by mass aqueous solution of the polymer of the present disclosure with a rheometer. More specifically, it can be measured and calculated by measuring the steady flow viscosity using an aluminum parallel plate (diameter: 60 mm, Gap: 1000 ⁇ m). Examples of the rheometer include those manufactured by TA Instruments.
  • the slope of the steady flow viscosity is -1 or more and less than 0, preferably -1 to ⁇ 0.05 as described above.
  • the upper or lower limit of the range is, for example, -0.95, -0.9, -0.85, -0.8, -0.75, -0.7, -0.65, -0.6,- At 0.55, -0.5, -0.45, -0.4, -0.35, -0.3, -0.25, -0.2, -0.15, or -0.1 There may be.
  • the range may be ⁇ 0.9 to ⁇ 0.1.
  • the balance of yield stress / yield strain in (B-2) is as follows. Create a logarithmic graph of x-axis: stress (Pa) and y-axis: strain (%), read the stress (Pa) and strain (%) at the point where the slope of the plot changes abruptly, and calculate the stress.
  • the yield stress was defined as the yield stress
  • the yield stress (Pa) value was divided by the yield strain (%) value
  • the value was defined as the “yield stress / yield strain balance”.
  • the yield stress / yield strain balance is 10 or more, preferably 10 to 40, as described above.
  • the upper or lower limit of the range is, for example, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31. , 32, 33, 34, 35, 36, 37, 38, or 39.
  • the range may be about 11 to 30.
  • the upper limit or the lower limit of the range is not particularly limited, and for example, 105, 110, 115, 120, 125, 130, 135, 140, 145, 150, 160, 170, 180, 190, 200, 250, 300, 350, 400. , Or 450.
  • the range may be 105 to 200 Pa ⁇ s.
  • the amount of polymer remaining on the sieve is the amount of the aqueous solution-containing polymer. It is a polymer having an amount of 50% by mass or less.
  • the lower limit of the amount of polymer remaining on the sieve is not particularly limited, but for example, 1% by mass or more of the amount of polymer contained in the aqueous solution is exemplified.
  • the upper or lower limit of the range (1 to 50% by mass) is, for example, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, It may be 44, 45, 46, 47, 48, or 49% by mass.
  • the range may be 10 to 45% by mass.
  • An aqueous solution containing 1% by mass of the polymer of the present disclosure and 0.5% by mass of sodium chloride is prepared, stirred well, and then the aqueous solution is poured onto a sieve having an opening of 75 ⁇ m, and the mass of the polymer remaining on the sieve is measured. By doing so, it is possible to examine whether or not the condition (C) is satisfied.
  • the viscosity of the 1% by mass polymer and 0.5% by mass aqueous solution of sodium chloride is lower than that of the 1% by mass aqueous solution of the polymer, but the viscosity is still high. Therefore, simply pouring an aqueous solution of 1% by mass of polymer and 0.5% by mass of sodium chloride onto a sieve may require a very long time for filtration. Therefore, in such a case, filtration may be promoted by lightly tracing a 1% by mass polymer and a 0.5% by mass aqueous solution of sodium chloride on the sieve with a spatula.
  • the post-swelling polymer contained in the 1% by mass polymer and the 0.5% by mass aqueous solution of sodium chloride is partially shrunk as compared with the post-swelling polymer contained in the 1% by mass aqueous solution of the polymer (thus, the viscosity is lowered). ), A 75 ⁇ m sieve will be sieved. Therefore, both the above conditions (A) and (C) can be satisfied. From this, the condition of (C) is that when sodium chloride is added to a 1% by mass aqueous solution of the polymer so as to have 0.5% by mass of sodium chloride, it shrinks and sifts a 75 ⁇ m sieve.
  • the proportion of the polymer is 50% by mass or more of the amount of the aqueous solution-containing polymer.
  • the upper limit of the proportion of the polymer is not particularly limited, but 99% is exemplified.
  • the upper or lower limit of the range (50 to 99% by mass) is, for example, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, It may be 93, 94, 95, 96, 97, or 98% by mass.
  • the range may be 55 to 90% by mass.
  • the polymer of the present disclosure is not particularly limited as long as it satisfies the above (A), (B) and (C), but above all, a water-soluble unsaturated carboxylic acid monomer is polymerized in the presence of a cross-linking agent.
  • the polymer thus obtained is preferred.
  • the polymer can be obtained, for example, by a method including a step of polymerizing a water-soluble unsaturated carboxylic acid monomer by a suspension polymerization method in the presence of a cross-linking agent.
  • a reverse phase suspension polymerization method in which a polymerization reaction is carried out while dispersing droplets of an aqueous phase containing a water-soluble unsaturated carboxylic acid monomer, a cross-linking agent and water in a hydrophobic solvent is preferable. ..
  • the water-soluble unsaturated carboxylic acid monomer is not particularly limited, and examples thereof include acrylic acid, methacrylic acid, maleic acid, maleic anhydride, fumaric acid, crotonic acid, and itaconic acid. Of these, acrylic acid and methacrylic acid are preferable.
  • the water-soluble unsaturated carboxylic acid monomer can be used alone or in combination of two or more. Of these, (meth) acrylic acid (acrylic acid and / or methacrylic acid) is preferable.
  • cross-linking agent for example, a known cross-linking agent used in the technical field (particularly, the water-absorbent resin field) can be used. More specifically, for example, water-soluble sucrose allyl ether, ethylene glycol diglycidyl ether, pentaerythritol allyl ether and the like can be preferably used.
  • the cross-linking agent may be used alone or in combination of two or more. Specific examples of the pentaerythritol allyl ether include pentaerythritol triallyl ether and pentaerythritol tetraallyl ether.
  • the degree of etherification of the water-soluble sucrose allyl ether is preferably 1.8 to 3.5, more preferably 2.0 to 3.2. This degree of etherification is the average value of the molar ratio of allyl ether groups to sucrose.
  • the degree of etherification can be calculated from the amount of acetic anhydride consumed by reacting the hydroxyl groups remaining in the sucrose allyl ether with acetic anhydride in pyridine.
  • the water-soluble sucrose allyl ether can be obtained, for example, by adding sodium hydroxide as a catalyst to an aqueous sucrose solution, converting sucrose into alkaline sucrose, and then dropping allyl bromide to carry out etherification. be able to. At this time, by adjusting the amount of allyl bromide in the range of 2 to 6 times mol, preferably 2 to 5 times mol, of sucrose, water-soluble sucrose allyl ether can be efficiently obtained. ..
  • the reaction temperature for etherification is, for example, about 80 ° C. Usually, the reaction is completed about 3 hours after the dropping of allyl bromide.
  • the water-soluble sucrose allyl ether can be recovered by adding alcohol to the aqueous phase separated from the reaction solution, filtering out the precipitated salts, and then distilling off excess alcohol and water.
  • hydrophobic solvent used for the reverse phase suspension polymerization for example, a petroleum-based hydrocarbon solvent selected from an aliphatic hydrocarbon, an alicyclic hydrocarbon and an aromatic hydrocarbon is used.
  • the aliphatic hydrocarbon include n-pentane, n-hexane and n-heptane.
  • the alicyclic hydrocarbon include cyclopentane, methylcyclopentane, cyclohexane and methylcyclohexane.
  • aromatic hydrocarbons include benzene, toluene and xylene.
  • At least one hydrophobic solvent selected from n-hexane, n-heptane, cyclohexane and toluene is preferably used as an industrial general purpose solvent.
  • the ratio of the hydrophobic solvent is, for example, 100 to 200 parts by mass with respect to 100 parts by mass of the aqueous phase containing the water-soluble unsaturated carboxylic acid monomer and the like.
  • the aqueous phase containing a water-soluble unsaturated carboxylic acid monomer or the like, or the hydrophobic solvent may contain other components such as a surfactant and a radical initiator.
  • Surfactants are mainly used to stabilize the suspension during polymerization.
  • the surfactant is not particularly limited as long as it is usually used in reverse phase suspension polymerization.
  • one or more surfactants selected from polyoxyethylene alkyl phenyl ether sulfates are used.
  • the amount of the surfactant is preferably 0.1 to 10% by mass, more preferably 0.5 to 5% by mass with respect to the water-soluble unsaturated carboxylic acid monomer.
  • the radical initiator is not particularly limited as long as it is used for ordinary radical polymerization, but potassium persulfate, ammonium persulfate, sodium persulfate, an azo-based initiator and the like are preferably used.
  • potassium persulfate, ammonium persulfate, sodium persulfate, an azo-based initiator and the like are preferably used.
  • 2,2'-azobis (2-methylpropionamidine) dihydrochloride can be used as a radical initiator.
  • the amount of the radical initiator is preferably 0.01 to 0.5% by mass, more preferably 0.02 to 0.2% by mass, based on the water-soluble unsaturated carboxylic acid monomer.
  • the amount of the radical initiator is within this range, the polymerization reaction can proceed more efficiently, and the obtained polymer is more excellent in thickening when used as a hydrophilic thickener.
  • the size of the droplets containing the water-soluble unsaturated carboxylic acid monomer and the like is closely related to the size of the obtained polymer particles.
  • a polymer of an appropriate size can be polymerized by performing reverse phase suspension polymerization at a stirring speed of 800 to 1000 rpm. It is likely that particles can be obtained.
  • the stirring speed during the polymerization reaction and controlling the size of the polymer particles (resin particles)
  • the medium particle size of the obtained resin particles can be adjusted. For example, resin particles having a size of 5 to 30 ⁇ m can be obtained.
  • the shape of the polymer particles thus obtained is spherical and is retained even in an aqueous liquid or a viscous substance such as cosmetics, for example, in cosmetics using the same, various properties, touch and usability can be obtained. It is considered to have a positive effect.
  • the medium particle size of the particles is the medium particle size of the volume average particle size measured by the laser diffraction method in which the particles are dispersed in n-hexane.
  • a measuring device laser diffraction type particle size distribution measuring device
  • SALD-2300 manufactured by Shimadzu Corporation
  • the medium particle size of the particles is preferably 5 to 30 ⁇ m, more preferably 5 to 25 ⁇ m, and even more preferably 6 to 20 ⁇ m.
  • the medium particle size of the particles By adjusting the medium particle size of the particles, the particle size when water is absorbed and swollen can also be adjusted. That is, by increasing the medium particle size of the particles, the particle size when water is absorbed and swollen can be increased, and by reducing the medium particle size of the particles, water is absorbed and swollen. The particle size can also be reduced.
  • the polymerization reaction temperature is, for example, 50 to 80 ° C.
  • the reaction time is, for example, 30 minutes to 3 hours.
  • the bath temperature can be adjusted to 60 ° C. to start the polymerization reaction.
  • the start of the polymerization reaction can be confirmed from the fact that the temperature inside the reaction vessel rises to about 70 ° C. due to the heat of polymerization.
  • the polymerization reaction is usually completed by carrying out the aging reaction for about 30 minutes to 3 hours.
  • the reaction may not be completed sufficiently and the amount of remaining water-soluble unsaturated carboxylic acid monomer may increase.
  • the product can be obtained by raising the bath temperature and distilling off the water and the petroleum-based hydrocarbon solvent in the reaction vessel.
  • the degree of neutralization of the polymer can be easily adjusted by neutralizing the carboxyl group of the water-soluble unsaturated carboxylic acid with an alkali.
  • the degree of neutralization here refers to the ratio of the number of moles of neutralized groups to the total number of moles of carboxyl groups of the water-soluble unsaturated carboxylic acid.
  • Examples of the alkali used for neutralization include sodium hydroxide, potassium hydroxide, triethanolamine, diisopropylamine and the like.
  • the neutralization method is not particularly limited, and examples thereof include a method of neutralizing a water-soluble unsaturated carboxylic acid monomer in advance, a method of neutralizing a polymer obtained by polymerization, and the like.
  • the degree of neutralization of the polymer of the present disclosure is not particularly limited, but may be, for example, 95% or less. For example, 90% or less is preferable, 85% or less or 80% or less is more preferable, and 75% or less is further preferable.
  • the lower limit of the degree of neutralization is not particularly limited, and examples thereof include 0% or more or 5% or more.
  • the upper or lower limit of the neutralization degree range (0% to 95%) is, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, It may be 91, 92, 93, or 94%.
  • the range may be 20 to 80%, and more preferably about 40 to 75%.
  • the amount of the cross-linking agent used is not particularly limited, but is preferably 0.01 to 1 part by mass, more preferably 0.05 to 0.8 parts by mass with respect to 100 parts by mass of the water-soluble unsaturated carboxylic acid monomer. , 0.1-0.6 parts by mass is more preferable.
  • the polymer particles of the present disclosure absorb water and swell in the composition of the present disclosure, so that the medium particle size thereof is preferably about 8 to 10 times larger than that before compounding. ..
  • the medium particle size of the absorbed particles is 100 to 600 ⁇ m.
  • the medium particle size is the medium particle size of the volume average particle size measured by the laser diffraction method.
  • a measuring device laser diffraction type particle size distribution measuring device
  • SALD-2300 manufactured by Shimadzu Corporation
  • composition of the present disclosure may contain various components other than the polymer of the present disclosure.
  • the composition of the present disclosure when used as an external composition (particularly a pharmaceutical composition or a cosmetic composition), it may contain a known ingredient used in the art.
  • composition of the present disclosure when used as a cosmetic composition (particularly a sunscreen composition), an ultraviolet protective agent can be preferably used.
  • the UV protection agent is not particularly limited, but is preferably an organic compound (that is, an organic UV protection agent).
  • the ultraviolet protective agent means an agent capable of protecting the influence of ultraviolet rays on the skin, and includes, for example, an ultraviolet absorber and an ultraviolet scattering agent.
  • the UV protection agent there are a lipophilic UV protection agent and a hydrophilic UV protection agent, but since the composition of the present disclosure is an O / W type emulsion composition, any UV protection agent can be used. , Either one or both can be used.
  • the lipophilic UV protection agent may be contained in the oil phase (O phase) and the hydrophilic UV protection agent may be contained in the aqueous phase (W phase).
  • UV protection agent those known in the art can be used.
  • the lipophilic organic UV protection agent and the hydrophilic organic UV protection agent are illustrated below.
  • oil-based organic ultraviolet protective agent examples include paraaminobenzoic acid derivatives, salicylic acid derivatives, silicic acid derivatives, benzophenone or aminobenzophenone, anthranyl acid derivatives, dibenzoylmethane derivatives, ⁇ , ⁇ -diphenylacrylate derivatives, benzilidencanfer derivatives, and phenyl.
  • Benzoimidazole derivative benzotriazole derivative, triazine derivative, bisresorcinyl triazine, imidazoline derivative, benzalmaronate derivative, 4,4-diarylbutadiene derivative, benzoxazole derivative, merocyanine, diphenylbutadiene malonate or diphenylbutadiene malonitrile derivative , Calcon and the like are exemplified.
  • Examples of the lipophilic UV-A protective agent capable of absorbing UV rays of 320 to 400 nm include the following.
  • dibenzoylmethane derivatives include 4-isopropyldibenzoylmethane, 1- (4-methoxy-1-benzofuran-5-yl) -3-phenylpropane-l, 3-dione, 1- (4- (tert-butyl). ) Phenyl) -3- (2-Hydroxyphenyl) Propane-1,3-dione, butylmethoxydibenzoylmethane (t-butylmethoxydibenzoylmethane), aminobenzophenone, and 2- (4-diethylamino-2-hydroxybenzoyl) ) N-hexyl benzoate, etc.
  • anthranilic acid derivative examples include anthranilic acid menthyl and the like.
  • 4,4-diarylbutadiene derivative include 1,1-dicarboxy- (2,2'-dimethylpropyl) -4,4-diphenylbutadiene.
  • Examples of the lipophilic UV-B protective agent capable of absorbing UV rays of 280 to 320 nm include the following.
  • PABA indicates "para-aminobenzoic acid”.
  • para-aminobenzoate examples include ethyl PABA, ethyldihydroxypropyl PABA, and ethylhexyldimethyl PABA.
  • salicylic acid derivative examples include homosalate, ethylhexyl salicylate, dipropylene glycol salicylate, TEA salicylic acid and the like.
  • Examples of the cinnamic acid derivative include ethylhexyl methoxycinnamate, isopropyl methoxycinnamate, isoamyl methoxycinnamate, diisopropyl methoxycinnamate, cinoxate, and glyceryl hexaneate ethyl methoxycinnamate.
  • Examples of the ⁇ , ⁇ -diphenylacryllate derivative include octocrylene and ethocrylene.
  • Examples of the benzylidene camphor derivative include 3-benzylidene camphor, methyl benzylidene camphor, polyacrylamide methyl benzylidene camphor and the like.
  • triazine derivatives for example, ethylhexyltriazone, diethylhexylbutamidotriazone, 2,4,6-tris (4'-dineopentyl aminobenzalmaronate) -s-triazine, 2,4,6-tris (4') -Diisobutyl aminobenzoate)-s-triazine, 2,4-bis (4'-dineopentyl aminobenzoate) -6- (4'-n-butyl aminobenzoate)-s-triazine, 2, Examples thereof include 4-bis (4'-aminobenzoic acid n-butyl) -6- (aminopropyl-trisiloxane) -s-triazine.
  • Examples of the imidazoline derivative include ethylhexyl dimethoxybenzylidendioxoimidazoline propionate.
  • Examples of the benzalmalonate derivative include polyorganosiloxane containing a benzalmalonate functional group such as polysilicone-15, dineopentyl 4'-methoxybenzalmalonate and the like.
  • Examples of the merocyanine derivative include octyl 5-N, N-diethylamino-2-phenylsulfonyl-2,4-pentadiene.
  • lipophilic wide-area UV protection agents capable of absorbing UV-A and UV-B rays include the following.
  • benzophenone derivative examples include benzophenone-1 (oxybenzone-1), benzophenone-2 (oxybenzone-2), benzophenone-3 (oxybenzone-3), benzophenone-8 (oxybenzone-8), and benzophenone-10 (oxybenzone-10).
  • benzophenone-11 examples include benzophenone-11
  • benzophenone-12 examples include benzotriazole derivative
  • benzotriazole derivative examples include drometrizoletrisiloxane and bumetrizole.
  • bisresorcinyltriazine derivative examples include bisethylhexyloxyphenol methoxyphenyltriazine and the like.
  • benzoxazole derivative examples include 2,4-bis [5-1 (dimethylpropyl) benzoxazole-2-yl- (4-phenyl) imino] -6- (2-ethylhexyl) imino-1,3,5-triazine and the like. Can be mentioned.
  • Derivatives of the family of diphenylbutadiene malonate or diphenylbutadiene malonitrile are compounds represented by the following general formulas.
  • R 3 represents a C1-C2 alkyl group or a C1-C2 alkoxy group, where n is equal to 0, 1 or 2;
  • diphenylbutadiene malonate or diphenylbutadiene malonitrile derivative for example, 2- (3,3-diphenylprop-2-enylidene) dimethyl malonate, 2- (3,3-diphenylprop-2-enylidene) diisobutyl malonic acid, 2- (3,3-diphenylprop-2-enylidene) bis-malonate (1,3-dimethylbutyl), 2- (3,3-diphenylprop-2-enylidene) dineopentyl malonic acid, (2Z) -2-cyano-5,5-diphenylpenta-2,4-methyl dieneate, (2Z) -2- (3,3-diphenylprop-2-enylidene) ethyl malonate (trimethylsilyl) methyl, (2E) -2-cyano-5,5-diphenyl-N- (3- ⁇ 1,3,3,3-tetramethyl-1-[(trimethyl)
  • European Patent No. 0 916 335 describes carbon derivatives and methods for their preparation
  • No. 1 535 925 describes siloxane and silane derivatives, respectively.
  • Derivatives of the chalcone family are, for example, compounds represented by the following general formulas.
  • the R 7 and R 8 groups are independent of each other, a hydrogen atom, a hydroxy group, a linear or branched C1-C12 alkyl or alkenyl group, and a linear or branched C1-C12 alkoxy group.
  • p and q mean the same or different 0, 1, 2, 3, 4, or 5
  • chalcone derivatives for example 2'-Hydroxy chalcone, 4'-Hydroxy chalcone, 4'-Methoxychalcone, 2'-Hydroxy-4-methoxychalcone, 2'-Hydroxy-4-hexyloxychalcone, 2'-Hydroxy-4-methyl chalcone, 2'-Hydroxy-3-hexyloxychalcone, 2'-Hydroxy-4'-Hexyloxy-4-methylchalcone, 2'-Hydroxy-4'-hexanoyloxy-4-methoxychalcone, 2', 4', 4-trihydroxy-3,3'-diallyl chalcone (known as Kazonol), 2', 4', 4-trihydroxy-5'-(3-methylbut-2-) Enil) Chalcone (known as Broussochalcone B), 2', 3', 4', 6', 4-pentahydroxy
  • Carthamin The corresponding 2', 3', 4', 6', 4-pentahydroxychalcones (known as Carthamin) can be preferably used.
  • Salicylic acid derivatives specifically homosalate or ethylhexyl salicylate, Cinnamic acid derivatives such as ethylhexyl methoxycinnamate, ⁇ , ⁇ -diphenylacryllate derivatives such as octocrylene, Dibenzoylmethane derivatives such as butylmethoxydibenzoylmethane, Triazine derivatives such as ethylhexyltriazone or diethylhexylbutamidotriazone, Benzotriazole derivatives such as drometrizoletrisiloxane, And their mixtures can be selected.
  • hydrophilic UV protection agents that can be used according to the present invention Telephthalylidenedic camphor sulfonic acid, Bisbenzoxazolyl derivatives, more specifically phenyldivene imidazole tetrasulfonate disodium, etc.
  • P-aminobenzoic acid (PABA) derivatives such as PABA, glyceryl PABA, PEG-25 PABA, phenylbenzimidazole sulfonic acid, Ferulic acid, Salicylic acid, Ocyl methoxycinnamate DEA, Benzylidene camphorsulfonic acid, Camphor Benzalkonium Methosulfate Benzophenone-4, Benzophenone-5, benzophenone-9 and the like can be particularly preferred.
  • an ingredient capable of forming an aqueous phase for example, an ingredient known in the cosmetics field can be used.
  • a hydrophilic organic solvent includes linear or branched lower monoalcohols having 1 to 8 carbon atoms such as ethanol, propanol, butanol, isopropanol or isobutanol, as well as propylene.
  • examples thereof include polyols such as glycol, isoprene glycol, butylene glycol, propylene glycol, glycerol (glycerin), sorbitol, polyethylene glycol, and derivatives thereof.
  • hydrophilic ultraviolet light is also a component that can form an aqueous phase. These components can be used alone or in combination of two or more.
  • the component capable of forming the oil phase for example, a component known in the field of cosmetics can be used.
  • a component known in the field of cosmetics can be used.
  • hydrocarbon oils, vegetable oils and fats, fatty acids, fatty acid esters and the like can be mentioned.
  • the following components are exemplified.
  • Hydrocarbon oils of animal or plant origin such as squalane, perhydrosqualene; Triglyceride of heptanic acid or octanoic acid, or, for example, sunflower oil, corn oil, soybean oil, cucumber oil, grapeseed oil, sesame oil, hazelnut oil, apricot oil, macadamia oil, arara oil, sunflower oil or avocado oil, capric acid / Plant-derived hydrocarbon oils such as capric acid triglycerides, jojoba oil or shea butter oil, fatty acid liquid triglycerides containing 4-10 carbon atoms; Pure serine oil, isononyl isononanoate, isopropyl myristate, 2-ethylhexyl palmitate, 2-octyldodecyl stearate, 2-octyldodecyl erucate or isostearyl isostearate; isostearyl lactic acid, octyl hydroxyste
  • Hydrolated esters such as dodecyl, diisostearyl malate, triisocetyl citrate or heptanate of fatty alcohols, octanate or decanoate; polyol esters such as propylene glycol dioctanoate, neopentyl glycol diheptate and diethylene glycol diisononanoate; and pentaisostearate penta Oils or formulas RaCOORb and RaORb, such as pentaerythritol esters such as erythrityl (where Ra represents a residue of a fatty acid containing 8 to 29 carbon atoms and Rb contains 3 to 30 carbon atoms.
  • Synthetic esters and ethers of especially fatty acids such as (representing branched or unbranched hydrocarbon chains); Liquid paraffins that may or may not be volatile and their derivatives, such as petrolatum, polydecene, isohexadecane, isododecane or hydropolyisobutene such as Parleam® oil, substantially direct from minerals or synthetics.
  • Chain or branched hydrocarbons such as cetyl alcohol, stearyl alcohol and mixtures thereof (cetearyl alcohol), octyldodecanol, 2-butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol, oleyl alcohol or linoleyl alcohol.
  • Fat alcohol with atoms Alkoxy fatty alcohols, specifically ethoxylated fatty alcohols such as oleth-12, ceteales-12 and ceteares-20; Fluorinated oils (perfluoromethylcyclopentane, perfluoro-1,3-dimethylcyclohexane; perfluoro-1,2-dimethylcyclobutane, dodecafluoropentane, tetradecafluorohexane, perfluoroalkanes such as bromoperfluorooctyl, nonafluoromethoxybutane, nona Fluoroethoxyisobutane, 4- (trifluoromethyl) perfluoromorpholin, etc .; Silicone oil, specifically cyclopolydimethylsiloxane (cyclomethicone) such as cyclohexadimethylsiloxane and cyclooentadimethylsiloxane; including pendant alkyl, alkoxy or phen
  • Polydimethylsiloxanes these groups are polydimethylsiloxanes with 2 to 24 carbon atoms; or phenyltrimethicone, phenyldimethicone, phenyl (trimethylsiloxy) diphenylsiloxane, diphenyldimethicone, diphenyl (methyldiphenyl) -tri.
  • Phenylated silicones such as siloxane, (2-phenylethyl) trimethylsiloxysilate and polymethylphenylsiloxane; Fatty acids containing 8-30 carbon atoms such as stearic acid, lauric acid, palmitic acid and oleic acid; Lanolin, beeswax, carnauba wax or candelilla wax, paraffin, lignite wax or microcrystalline wax, synthetic wax and / or lipophilic UV protection agents are also components that can form an oil phase. These components can be used alone or in combination of two or more.
  • the composition of the present disclosure preferably contains an emulsifier.
  • an emulsifier for example, an ingredient known in the field of cosmetics can be used. More specifically, for example, glycerin fatty acid ester, organic acid monoglyceride (particularly fatty acid monoglyceride), polyglycerin fatty acid ester, propylene glycol fatty acid ester, polyglycerin condensed ricinoleic acid ester, sorbitan fatty acid ester, sucrose fatty acid ester, lecithin, enzymatic decomposition. Recitin and the like can be preferably used.
  • fatty acid monoglycerides are preferable, and linear or branched chain fatty acids having 8 to 20 carbon atoms (8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20) are preferable.
  • a monoester of (straight chain fatty acid) and glycerin is preferable.
  • composition of the present disclosure is not particularly limited, but preferably contains 5 to 30% by mass of an ultraviolet protective agent.
  • the upper or lower limit of the range is, for example, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26. , 27, 28, or 29% by weight.
  • the range may be 6 to 29% by mass.
  • composition of the present disclosure is not particularly limited, but the aqueous phase (W phase) is preferably 70% by mass or more, and more preferably 71, 72, 73, 74, or 75% by mass or more.
  • composition of the present disclosure may contain silica.
  • silica When silica is contained, the content thereof is preferably about 0.1 to 5 parts by mass with respect to 100 parts by mass of the polymer of the present disclosure contained in the composition.
  • the upper or lower limit of the range may be, for example, 0.5, 1, 1.5, 2, 2.5, 3, 3.5, 4, or 4.5 parts by mass.
  • the range may be 0.5 to 4 parts by mass.
  • the composition of the present disclosure has significantly improved emulsion stability as compared with the conventional O / W type emulsion composition.
  • the amount of liquid separated is less than 3 g, 2.5 g or less, 2 g or less, 1.5 g or less, 1 g or less, or 0. It is more preferably 5.5 g or less, and further preferably 0.1 g or less.
  • the composition of the present disclosure preferably has a viscosity of, for example, 8000 mPa ⁇ s or more, and more preferably about 8000 to 35000 mPa ⁇ s.
  • the upper or lower limit of the range is, for example, 9000, 10000, 11000, 12000, 13000, 14000, 15000, 16000, 17000, 18000, 19000, 20000, 21000, 22000, 23000, 24000, 25000, 26000, 27000, 28000, It may be 29000, 30000, 31000, 32000, 33000, or 34000 mPa ⁇ s.
  • the range may be 10,000 to 30,000 mPa ⁇ s.
  • the viscosity is a value measured at room temperature (25 ° C.) at a rotation speed of 20 rpm using a B-type viscometer manufactured by BrookField.
  • composition of the present disclosure exhibiting such excellent emulsion stability (particularly the effect of suppressing separation) can be obtained by preparing by the following preparation method.
  • a component to be contained in the oil phase (oil phase component) and the polymer of the present disclosure are mixed to prepare a polymer dispersion composition, and a component to be further contained in the aqueous phase (water phase component).
  • an emulsifier is added and further mixed to prepare an O / W type emulsion composition, whereby the composition of the present disclosure can be obtained.
  • the mixing can be performed by a known method, and may be heated and mixed if necessary. In the case of heating, for example, it may be heated to a temperature of about 50 to 90 ° C, more preferably about 60 to 80 ° C. Further, particularly when the composition of the present disclosure contains silica, it is preferable to mix the oil phase component and the polymer together with each other, and the polymer and silica are mixed in advance and then mixed with the oil phase component. It is more preferable to do so.
  • an emulsified composition is prepared by mixing an oil phase component and an aqueous phase component, and a polymer is added thereto to thicken the emulsion.
  • the method for preparing the composition of the present disclosure described above is more excellent in emulsification stability (particularly separation suppressing effect) than the above-mentioned usual manufacturing method.
  • a W-type emulsion composition can be prepared.
  • n-heptane 356 g was placed in a 2 L separable flask equipped with a stirrer, a reflux cooling tube, a dropping funnel and a nitrogen gas introduction tube, and as a polymer-based dispersant, both maleic anhydride-modified ethylene and propylene were added.
  • a polymer-based dispersant both maleic anhydride-modified ethylene and propylene were added.
  • 0.736 g of a polymer manufactured by Mitsui Kagaku Co., Ltd., high wax 1105A
  • sucrose stearic acid ester (surfactant, manufactured by Mitsubishi Chemical Foods Co., Ltd., Ryoto Sugar Ester) is added to 6.62 g of n-heptane. S-370, HLB value: 3)
  • a surfactant solution obtained by heating and dissolving 0.736 g was added to a separable flask. Then, in order to remove the atmosphere in the reaction vessel, the raw materials, and the oxygen present in the solvent, nitrogen gas is blown into the solution to replace the nitrogen in the system, and the bath temperature is maintained at 70 ° C. Polymerization was carried out over time.
  • a water-absorbent resin which is a polymer of acrylic acid and a sodium salt thereof and which is a polymer crosslinked with ethylene glycol diglycidyl ether.
  • a sieve having an opening of 850 ⁇ m
  • 2.0% by mass of amorphous silica (Tokuseal NP-S manufactured by Oriental Silicas Corporation) based on the total mass of the water-absorbent resin is applied.
  • 90.3 g of a water-absorbent resin composition containing amorphous silica was obtained.
  • the average particle size of the obtained water-absorbent resin after swelling with water was 200 ⁇ m.
  • the average particle size is a medium particle size of the volume average particle size measured by a laser diffraction method (using a laser diffraction type particle size distribution measuring device: SALD-2300 (manufactured by Shimadzu Corporation)). The same applies to the following.
  • Aqueous ethylenically unsaturated carboxylic acid monomer was prepared by adding 0.04 g of amidin) dihydrochloride (V-50 manufactured by Wako Pure Chemical Industries, Ltd.).
  • n-heptane 330 g was placed in a 2 L separable flask equipped with a stirrer, a reflux condenser, a dropping funnel and a nitrogen gas introduction tube, and the surfactant sorbitan monostearate (Nichiyu Co., Ltd.) , Nonion SP-60R) 2.7 g was added, and this was dispersed and dissolved in n-heptane.
  • the previously prepared ethylenically unsaturated carboxylic acid monomer aqueous solution was added thereto. The bath temperature was maintained at 60 ° C.
  • a water-absorbent resin which is a polymer of acrylic acid and a sodium salt thereof and which is a polymer crosslinked with water-soluble sucrose allyl ether. ..
  • the average particle size of the obtained water-absorbent resin after swelling with water was 120 ⁇ m.
  • n-heptane 356 g was placed in a 2 L separable flask equipped with a stirrer, a reflux cooling tube, a dropping funnel and a nitrogen gas introduction tube, and as a polymer-based dispersant, both maleic anhydride-modified ethylene and propylene were added.
  • a polymer-based dispersant both maleic anhydride-modified ethylene and propylene were added.
  • 0.736 g of a polymer manufactured by Mitsui Kagaku Co., Ltd., High Wax 1105A
  • sucrose stearic acid ester (surfactant, manufactured by Mitsubishi Chemical Foods Co., Ltd., Ryoto Sugar Ester) is added to 6.62 g of n-heptane. S-370, HLB value: 3)
  • a surfactant solution obtained by heating and dissolving 0.736 g was added to a separable flask. Then, in order to remove the atmosphere in the reaction vessel, the raw materials, and the oxygen present in the solvent, nitrogen gas is blown into the solution to replace the nitrogen in the system, and the bath temperature is maintained at 70 ° C.
  • the first-stage polymerized slurry liquid was obtained over time.
  • a water-absorbent resin which is a polymer of acrylic acid and a sodium salt thereof and which is a polymer crosslinked with ethylene glycol diglycidyl ether.
  • a sieve having an opening of 850 ⁇ m
  • 2.0% by mass of amorphous silica (Tokuseal NP-S manufactured by Oriental Silicas Corporation) based on the total mass of the water-absorbent resin is applied.
  • 218.3 g of a water-absorbent resin composition containing amorphous silica was obtained.
  • the average particle size of the obtained water-absorbent resin after swelling with water was 660 ⁇ m.
  • a 1% by mass aqueous solution was prepared for the polymers A, B, or C, and the steady flow viscosity was measured with a rheometer. More specifically, a rheometer manufactured by TA Instruments is used, and an aluminum parallel plate (diameter: 60 mm, Gap: 1000 ⁇ m) is used to obtain a steady flow viscosity in the range of a shear rate of 0.000001 to 1,000 s -1 . It was measured.
  • an aqueous solution containing 1% by mass of the polymer A, B or C and 0.5% by mass of sodium chloride was prepared and sieved with an opening of 75 ⁇ m. The mass of polymer remaining on the sieve was measured. Then, it was calculated how much the mass of the polymer remaining on the sieve was the mass% of the mass of the polymer contained in the aqueous solution. It can be said that the calculation result indicates the salt tolerance of each polymer (the smaller the value, the lower the salt tolerance).
  • the calculation results (salt tolerance) and the results of the above examination are summarized in the following table. It should be noted that when the polymer is applied to the skin, the one having low salt tolerance has a sharp decrease in viscosity due to the influence of salt on the skin, and a refreshing tactile sensation can be obtained.
  • O / W type emulsion composition 1 According to the composition shown in Table 2, the oil phase component (UV absorber) and the polymer composition are mixed at 75 ° C. to prepare a polymer dispersion composition, which is further mixed with a polyhydric alcohol, an emulsifier, and ion-exchanged water. Was mixed at 75 ° C. and emulsified, and allowed to cool to room temperature with stirring to prepare an O / W type emulsion composition (sunscreen composition). The unit of the numerical value of each component in Table 2 is g (gram).
  • compositions of Example 1a, Example 2a, and Comparative Example 3a When the viscosities of the compositions of Example 1a, Example 2a, and Comparative Example 3a were measured, they were 22800 mPa ⁇ s, 24600 mPa ⁇ s, and 7700 mPa ⁇ s, respectively. Further, the compositions of Examples 1a and 2a have higher emulsification stability than the composition of Comparative Example 3a, and the compositions of Examples 1b and 2b have higher emulsification stability than the composition of Comparative Example 3a. it was high. The emulsification stability was examined by visually confirming whether layer separation had occurred.
  • the viscosity is a value measured at room temperature (25 ° C.) using a B-type viscometer manufactured by BrookField with a rotation speed of 20 rpm.
  • O / W type emulsion composition 2 [Example manufacturing method] According to the composition shown in Table 3, the oil phase component (UV absorber) and the polymer composition are mixed at 75 ° C. to prepare a polymer dispersion composition, which is further mixed with a polyhydric alcohol, an emulsifier, and ion-exchanged water. Was mixed at 75 ° C. and emulsified, and allowed to cool to room temperature with stirring to prepare an O / W type emulsion composition (sunscreen composition).
  • An emulsified composition was prepared by mixing an oil phase component (UV absorber) and an aqueous phase component (ion-exchanged water and an emulsifier) at 75 ° C. according to the composition shown in Table 3. Separately, the polymer composition and the polyhydric alcohol were mixed to prepare a polymer dispersion composition. Then, the polymer dispersion composition was added to the emulsified composition, mixed, and allowed to cool to room temperature with stirring to prepare an O / W type emulsion composition (sunscreen composition).
  • an oil phase component UV absorber
  • an aqueous phase component ion-exchanged water and an emulsifier
  • Figure 3 shows the outline of the above manufacturing method.
  • the unit of the numerical value of each component in Table 3 is g (gram).
  • the compositions prepared by the production methods of Examples 6, 7, 8 and 9 in Table 3 are the same as the compositions of Example 1a, Example 2a, Example 1b and Example 2b in Table 2, respectively. Is.
  • Each O / W type emulsion composition (100 g) obtained was transferred to a 100 ml centrifuge, centrifuged at 2000 rpm at 25 ° C. for 10 minutes, and then the weight of the separated liquid was measured. Further, when the panelists applied each O / W type emulsion composition to their own skin, the composition prepared by the comparative example manufacturing method felt slimy, while the composition prepared by the example manufacturing method was slimy. There was no (that is, it was refreshing), and it was a good feeling to feel the freshness. These results are also shown in Table 3.

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Abstract

L'invention concerne une composition d'émulsion de type huile dans l'eau ayant une excellente stabilité à l'émulsion.　Plus spécifiquement, l'invention concerne une composition d'émulsion de type huile dans l'eau qui contient un polymère absorbant l'eau, le polymère absorbant l'eau satisfaisant les conditions suivantes (A), (B) et (C). (A) : la taille des particules après gonflement à l'eau est de 100 à 600 µm. (B) : au moins un élément parmi (B-1) et (B-2) est satisfait. (B-1) : la pente dans le tracé bilogarithmique de la viscosité à écoulement constant d'une solution aqueuse de 1 % en masse du polymère est de -1 à 0 (à l'exclusion de 0, dans la plage de vitesse de cisaillement de 0,1 à 1 000 s-1). (B-2) : le rapport limite d'élasticité / contrainte d'élasticité d'une solution aqueuse de 1 % en masse du polymère est d'au moins 10. (C) : lorsqu'une solution aqueuse de 1 % en masse du polymère et 0,5 % en masse de chlorure de sodium est tamisée avec une ouverture de 75 µm, la quantité de polymère restant sur le tamis est de maximum 50 % en masse par rapport à la quantité de la solution aqueuse contenant le polymère, et lorsque 100 g de ladite composition est centrifugé à 2 000 tr/min pendant 10 minutes à 25 °C, un volume de liquide de séparation est inférieur à 3 g.
PCT/JP2021/046706 2020-12-25 2021-12-17 Composition d'émulsion de type huile dans l'eau contenant un polymère WO2022138482A1 (fr)

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2015224240A (ja) * 2014-05-29 2015-12-14 住友精化株式会社 紫外線吸収剤と紫外線散乱剤を含有する組成物
WO2016002751A1 (fr) * 2014-06-30 2016-01-07 株式会社 資生堂 Composition de type émulsion huile dans l'eau
JP2016023143A (ja) * 2014-07-17 2016-02-08 住友精化株式会社 紫外線吸収剤を含有する組成物
JP2016147813A (ja) * 2015-02-10 2016-08-18 住友精化株式会社 紫外線吸収剤を含有する組成物
JP2017081875A (ja) * 2015-10-30 2017-05-18 花王株式会社 皮膚化粧料
JP2018095637A (ja) * 2016-12-07 2018-06-21 花王株式会社 水中油型紫外線防御化粧料
WO2018198737A1 (fr) * 2017-04-27 2018-11-01 株式会社 資生堂 Composition cosmétique d'écran solaire mélangé à une poudre poreuse

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2015224240A (ja) * 2014-05-29 2015-12-14 住友精化株式会社 紫外線吸収剤と紫外線散乱剤を含有する組成物
WO2016002751A1 (fr) * 2014-06-30 2016-01-07 株式会社 資生堂 Composition de type émulsion huile dans l'eau
JP2016023143A (ja) * 2014-07-17 2016-02-08 住友精化株式会社 紫外線吸収剤を含有する組成物
JP2016147813A (ja) * 2015-02-10 2016-08-18 住友精化株式会社 紫外線吸収剤を含有する組成物
JP2017081875A (ja) * 2015-10-30 2017-05-18 花王株式会社 皮膚化粧料
JP2018095637A (ja) * 2016-12-07 2018-06-21 花王株式会社 水中油型紫外線防御化粧料
WO2018198737A1 (fr) * 2017-04-27 2018-11-01 株式会社 資生堂 Composition cosmétique d'écran solaire mélangé à une poudre poreuse

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