WO2021200137A1 - Composition visqueuse - Google Patents

Composition visqueuse Download PDF

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Publication number
WO2021200137A1
WO2021200137A1 PCT/JP2021/010730 JP2021010730W WO2021200137A1 WO 2021200137 A1 WO2021200137 A1 WO 2021200137A1 JP 2021010730 W JP2021010730 W JP 2021010730W WO 2021200137 A1 WO2021200137 A1 WO 2021200137A1
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acid
water
composition
soluble
unsaturated carboxylic
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PCT/JP2021/010730
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Japanese (ja)
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友佳 境
山口　博史
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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
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
    • C08F22/02—Acids; Metal salts or ammonium salts thereof, e.g. maleic acid or itaconic acid
    • 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
    • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • C08K5/092—Polycarboxylic acids
    • 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
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/17—Amines; Quaternary ammonium compounds
    • 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
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or 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 of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/02—Homopolymers or copolymers of acids; Metal or ammonium salts thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L35/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers

Definitions

  • the present disclosure relates to a viscous composition or the like.
  • a polymer obtained by polymerizing a water-soluble unsaturated carboxylic acid monomer in the presence of water-soluble sucrose allyl ether is known to be useful as, for example, a thickener for cosmetics (for example, Patent Documents). 1).
  • compositions containing a polymer obtained by polymerizing a water-soluble unsaturated carboxylic acid monomer in the presence of water-soluble sucrose allyl ether loses its viscosity over time when stored for a long period of time. I found that there was a high risk of being affected. As described above, although the composition can be used as a cosmetic or the like, it is not preferable that the viscosity is lost over time.
  • the present inventors have further studied in order to find a method for providing a composition containing the polymer and in which the decrease in viscosity with time is suppressed.
  • an O / W emulsion composition containing a chelating agent in addition to the polymer may suppress a decrease in viscosity over time, and have made further improvements.
  • Item 1 An O / W emulsion composition
  • a polymer obtained by polymerizing a water-soluble unsaturated carboxylic acid monomer in the presence of water-soluble sucrose allyl ether and (B) a chelating agent.
  • the chelating agent is at least one selected from the group consisting of ethylenediamine tetraacetic acid, pentetoic acid, phytic acid, etidronic acid, citric acid, and hexametaphosphate, and salts thereof.
  • the chelating agent is at least one selected from the group consisting of ethylenediamine tetraacetic acid, pentetoic acid, phytic acid, etidronic acid, citric acid, and hexametaphosphate, and salts thereof.
  • the water-soluble unsaturated carboxylic acid monomer in (A) is at least one selected from the group consisting of acrylic acid, methacrylic acid, maleic acid, maleic anhydride, fumaric acid, crotonic acid, and itaconic acid.
  • Item 2. The composition according to Item 1 or 2.
  • Item 4. Item 2. The item 1 to 3, wherein the amount of the water-soluble sucrose allyl ether in (A) is 0.01 to 1 part by mass with respect to 100 parts by mass of the water-soluble unsaturated carboxylic acid monomer. Composition.
  • the chelating agent is at least one selected from the group consisting of ethylenediamine tetraacetic acid, pentetic acid, phytic acid, etidronic acid, citric acid, and hexametaphosphate, and salts thereof.
  • the water-soluble unsaturated carboxylic acid monomer in (A) is at least one selected from the group consisting of acrylic acid, methacrylic acid, maleic acid, maleic anhydride, fumaric acid, crotonic acid, and itaconic acid.
  • the amount of the water-soluble sucrose allyl ether in (A) is 0.01 to 1 part by mass with respect to 100 parts by mass of the water-soluble unsaturated carboxylic acid monomer.
  • Item 4. The composition according to Item 4.
  • Item 6. Item 2. The composition according to any one of Items 1 to 5, wherein the viscosity retention rate from the 7th day to the 30th day of production is 80% or more when stored at 50 ° C.
  • composition containing a polymer obtained by polymerizing a water-soluble unsaturated carboxylic acid monomer in the presence of water-soluble sucrose allyl ether, and suppressing a decrease in viscosity over time.
  • the viscosity and viscosity retention of an O / W emulsion composition containing a polymer obtained by polymerizing a water-soluble unsaturated carboxylic acid monomer in the presence of water-soluble sucrose allyl ether and various chelating agents are shown.
  • the viscosity and viscosity retention of an aqueous composition containing a polymer obtained by polymerizing a water-soluble unsaturated carboxylic acid monomer in the presence of water-soluble sucrose allyl ether and various chelating agents are shown.
  • the present disclosure describes a composition containing a polymer obtained by polymerizing a water-soluble unsaturated carboxylic acid monomer in the presence of water-soluble sucrose allyl ether, and suppressing a decrease in viscosity over time, and its use.
  • a composition containing a polymer obtained by polymerizing a water-soluble unsaturated carboxylic acid monomer in the presence of water-soluble sucrose allyl ether, and suppressing a decrease in viscosity over time and its use.
  • And methods for producing the same, etc. but are not limited thereto, and the present disclosure includes all disclosed in the present specification and recognized by those skilled in the art.
  • the composition included in the present disclosure is (A) a polymer obtained by polymerizing a water-soluble unsaturated carboxylic acid monomer in the presence of water-soluble sucrose allyl ether (“polymer (A)” in the present specification. It is an O / W emulsion composition containing (sometimes referred to as) and (B) a chelating agent.
  • the composition included in the present disclosure may be referred to as "the composition of the present disclosure”.
  • the chelating agent is contained in the aqueous phase (W phase) and / or oil (O phase) of the O / W emulsion.
  • the polymer (A) is contained in the aqueous phase (W phase) of the O / W emulsion.
  • the composition of the present disclosure also includes water.
  • the polymer (A) is a polymer obtained by polymerizing a water-soluble unsaturated carboxylic acid monomer in the presence of water-soluble sucrose allyl ether.
  • 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 water-soluble sucrose allyl ether.
  • suspension polymerization methods a reverse phase suspension in which a polymerization reaction is carried out while dispersing aqueous phase droplets containing a water-soluble unsaturated carboxylic acid monomer, a water-soluble sucrose allyl ether and water in a hydrophobic solvent.
  • the polymerization method is preferable.
  • the water-soluble sucrose allyl ether can act as a water-soluble cross-linking agent.
  • the polymer (A) can be used alone or in combination of two or more.
  • 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 may be used alone or in combination of two or more.
  • 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 for etherification. can. 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 allyl bromide is added dropwise.
  • 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 reverse phase suspension polymerization for example, a petroleum hydrocarbon solvent selected from aliphatic hydrocarbons, alicyclic hydrocarbons and aromatic hydrocarbons is used.
  • aliphatic hydrocarbon include n-pentane, n-hexane and n-heptane.
  • 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 state 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, based on the water-soluble unsaturated carboxylic acid monomer.
  • a small amount of surfactant may cause some problems in the stability of the suspension state during polymerization, and a large amount of surfactant tends to be economically disadvantageous.
  • 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 the 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. Therefore, cosmetics using the polymer particles are good in various properties, touch and usability. It is thought to have an 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-2000A 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 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 to distill off water and a 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 (A) is not particularly limited, but for example, 50% or less is preferable, 45% or less is more preferable, and 40% or less is further preferable.
  • the amount of the water-soluble sucrose allyl ether used is not particularly limited, but is preferably 0.01 to 1 part by mass, preferably 0.05 to 0.8 parts by mass with respect to 100 parts by mass of the water-soluble unsaturated carboxylic acid monomer. Parts are more preferable, and 0.1 to 0.6 parts by mass are even more preferable.
  • the particles of the polymer (A) 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 that before compounding. ..
  • the medium particle size of the absorbed particles is preferably about 40 to 300 ⁇ m, more preferably about 50 to 250 ⁇ 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-2000A manufactured by Shimadzu Corporation
  • the chelating agent (B) is not particularly limited as long as the effect of the composition of the present disclosure (suppression of viscosity decrease over time) is not impaired, and a known chelating agent can be used. More specifically, for example, ethylenediamine tetraacetic acid (EDTA), diethylenetriaminepentacetic acid, ethylenediaminehydroxyethyltriacetic acid, hydroxyethanediphosphonic acid, gluconic acid, dihydroxyethylglycine, dicarboxymethylglutamic acid, hydroxyethyliminodiacetic acid, 1, Examples thereof include 3-propanediamine tetraacetic acid, triethylenetetraamine hexaacetic acid, hydroxyethylenediamine triacetic acid, L-glutamate diacetic acid, pentetoic acid, phytic acid, etidroic acid, citric acid, hexametaphosphate, and salts thereof.
  • EDTA ethylenediamine te
  • a metal salt is preferable, and an alkali metal salt or an alkaline earth metal salt is more preferable. More specifically, for example, sodium salt, potassium salt and calcium salt can be mentioned.
  • 5 sodium pentatetoate is preferably used as the salt of pentetic acid
  • sodium hexametaphosphate is preferably used as the salt of hexametaphosphate.
  • pentetic acid or a salt thereof is particularly preferable.
  • the chelating agent may be used alone or in combination of two or more.
  • the polymer (A) can be used alone or in combination of two or more, and even if the polymer (A) is used alone or in combination of two or more.
  • the chelating agent may be used alone or in combination of two or more.
  • the present disclosure includes any combination of any use of the polymer (A) (one or more) and any use of the chelating agent (B) (one or more).
  • composition of the present disclosure is useful, for example, as a cosmetic composition.
  • composition of the present disclosure may contain a component other than the above components as long as the effect is not impaired, and may contain, for example, a component known in the cosmetics field.
  • a thickener may be contained as long as the effect is not impaired.
  • the thickener include polysaccharide-based water-soluble polymers such as hydroxyethyl cellulose and xanthan gum, carboxyvinyl polymers, and alkyl-modified carboxyvinyl polymers.
  • powder components liquid fats and oils, solid fats and oils, waxes, hydrocarbon oils, higher fatty acids, higher alcohols, ester oils, silicone oils, surfactants (anionic surfactants, cationic surfactants, amphoteric surfactants).
  • Nonionic surfactant moisturizer, water-soluble polymer, film agent, ultraviolet absorber, metal ion sequestering agent, lower alcohol, polyhydric alcohol, sugar, amino acid, organic amine, polymer emulsion, pH adjuster, It may contain skin nutrients, vitamins, antioxidants, antioxidant aids, fragrances and the like. Such components can be used alone or in combination of two or more.
  • composition of the present disclosure When the composition of the present disclosure is used in the field of cosmetics, its form is not particularly limited, but for example, a lotion, a milky lotion, a beauty essence, a cream (medicinal cream, massage cream, cleansing cream, gel cream, etc.), a gel (cleansing gel, etc.) , Hair setting gel, moisturizing gel, styling gel, etc.), cream pack, facial cleansing foam, sunscreen, eyeliner, mascara, lipstick, foundation, etc.
  • a lotion a milky lotion, a beauty essence, a cream (medicinal cream, massage cream, cleansing cream, gel cream, etc.), a gel (cleansing gel, etc.) , Hair setting gel, moisturizing gel, styling gel, etc.), cream pack, facial cleansing foam, sunscreen, eyeliner, mascara, lipstick, foundation, etc.
  • composition of the present disclosure is an O / W emulsion composition
  • a surfactant for preparation.
  • Preferred surfactants include, for example, surfactants usually used in cosmetics (for example, nonionic surfactants, anionic surfactants, cationic surfactants, amphoteric surfactants) and the like.
  • sorbitan fatty acid ester polyglycerin fatty acid ester, sucrose fatty acid ester, sorbitol fatty acid ester, modified polyethylene wax, modified polypropylene wax, polyvinyl alcohol, polyethylene oxide, cellulose ether (hydroxyethyl cellulose, ethyl cellulose, etc.), sodium alkylbenzene sulfonate, and Polyoxyethylene alkyl phenyl ether sulfate and the like are preferably mentioned.
  • a fat component liquid fat, solid fat, wax, hydrocarbon oil, higher fatty acid, higher alcohol, ester oil, silicone oil, etc.
  • a fat component liquid fat, solid fat, wax, hydrocarbon oil, higher fatty acid, higher alcohol, ester oil, silicone oil, etc.
  • Preferred oil and fat components include, for example, those that can be usually used in cosmetics.
  • Specific examples thereof include natural oils, hydrocarbons, silicone oils, ester oils and the like in consideration of texture, familiarity, appearance, slipperiness and the like on the skin.
  • natural oil include olive oil, macadamia nut oil, castor oil, jojoba oil, orange raffy oil, beeswax, lanolin, squalane and the like.
  • the hydrocarbon include squalane, liquid paraffin, hydrogenated polyisobutene, hydrogenated polybutene, isododecane, polyethylene wax, polypropylene wax and the like.
  • silicone-based oil examples include modified silicone oils such as methylpolysiloxane, methylphenylpolysiloxane, cyclic methylsiloxane, and silicone polyether copolymers.
  • ester oil examples include various fatty acid esters, such as octyldodecyl ester and glycerin ester (for example, triethylhexanoin) of each fatty acid such as oleic acid, erucic acid, myristic acid, and ricinoleic acid. Be done.
  • an oil-soluble ultraviolet absorber, an oil-soluble agent, and the like can be mentioned.
  • the composition of the present disclosure also preferably contains a polyhydric alcohol, especially when used in the cosmetics field.
  • a polyhydric alcohol for example, a 1, 2, or trihydric alcohol is preferable. Further, alcohols having 1 to 6 carbon atoms (1, 2, 3, 4, 5, or 6) are preferable. More specifically, for example, glycerin, butylene glycol, pentylene glycol and the like are preferably mentioned.
  • composition of the present disclosure can be prepared, for example, by a known method for preparing an O / W emulsion composition or a method that can be easily conceived from a known method.
  • a method of mixing the components contained in the oil phase, separately mixing the components contained in the aqueous phase, and further mixing the two mixtures together can be mentioned.
  • the composition of the present disclosure is preferably an O / W composition containing an oil / fat component and a surfactant (emulsifier) in addition to the polymer (A) and a chelating agent, and an O / W composition further containing a polyhydric alcohol in addition to these.
  • the W composition is more preferred.
  • the fat and oil component is preferably contained in an amount of about 4 to 30% by mass based on the total amount of the composition.
  • the surfactant (emulsifier) is preferably contained in an amount of about 0.3 to 3% by mass based on the total amount of the composition.
  • the polyhydric alcohol is preferably contained in an amount of about 0 to 12% based on the total amount of the composition.
  • the viscosity of the composition of the present disclosure is measured using a BH type rotational viscometer. Specifically, it is measured by reading the viscosity value 1 minute after the start of rotation of the rotor at 25 ° C., assuming that the rotation speed of the spindle rotor is 20 rotations per minute.
  • the rotor can be appropriately set according to the viscosity, and as a guide, when the rotor is less than 2000 mPa ⁇ s, the rotor No. In the case of 3, 2000 mPa ⁇ s or more and less than 5000 mPa ⁇ s, the rotor No.
  • each viscous composition can be defoamed by centrifuging (for example, 2000 rpm ⁇ 10 to 20 minutes) before the viscosity measurement, and then used for the measurement.
  • the viscosity of the composition of the present disclosure can be appropriately set according to the composition of the components of the composition and the intended use, and is not particularly limited. For example, about 5000 to 35000 mPa ⁇ s is exemplified.
  • the composition of the present disclosure is excellent in viscosity retention over time.
  • the viscosity retention rate from the 7th day to the 30th day is preferably 80% or more, and more preferably 85% or more.
  • the viscosity retention rate is a relative value of the viscosity on the 30th day of storage when the viscosity on the 7th day of storage and the viscosity on the 30th day of storage are measured and the viscosity on the 7th day of production is 100%.
  • a stirrer, a reflux condenser and a dropping funnel were attached to a 500 mL separable flask.
  • 72 g of acrylic acid and water were put therein to prepare 90 g of an 80 mass% acrylic acid aqueous solution.
  • 54 g of a 30 mass% sodium hydroxide aqueous solution was added dropwise to prepare an acrylic acid neutralized aqueous solution having a neutralization degree of 40%.
  • 0.32 g of sucrose allyl ether obtained above and 0.04 g of 2,2′-azobis (2-methylpropionamidine) dihydrochloride (“V-50” manufactured by Wako Pure Chemical Industries, Ltd.) were added.
  • V-50 2,2′-azobis (2-methylpropionamidine) dihydrochloride
  • n-heptane 330 g was placed in a 2000 mL separable flask equipped with a stirrer, a reflux cooling tube, a dropping funnel and a nitrogen gas introduction tube, and a maleic anhydride-modified ethylene-propylene copolymer (Mitsui Kagaku).
  • High Wax Co., Ltd. 1105A 1.0 g and HLB3 sucrose stearic acid ester (Mitsubishi Chemical Foods Co., Ltd., Ryoto Sugar Ester S-370) 1.0 g were added as a surfactant, and this was added to n-heptane. Dissolved and dissolved in ester.
  • the previously prepared aqueous ethylenically unsaturated carboxylic acid monomer solution was added.
  • the bath temperature was maintained at 60 ° C. and the stirring speed was increased while nitrogen gas was blown into the solution to replace the nitrogen in the system in order to remove the atmosphere in the reaction vessel, the raw materials and the oxygen present in the solvent.
  • water and n-heptane were distilled off to obtain a polymer of acrylic acid and a sodium salt thereof.
  • the polymer may be referred to as polymer 1.
  • a moisturizing cream containing various study ingredients was prepared as follows. First, aqueous solutions of various study components were prepared. 2.50 g of the aqueous solution, 3.00 g of polysolvate 60 melted in a water bath at 60 ° C., and 64.16 g of ion-exchanged water were stirred using a stirrer while heating in a water bath at 60 ° C. until uniform. (Aqueous phase component mixture).
  • each of the obtained compositions was stored at 50 ° C., and the viscosity was measured on the 7th and 30th days. Further, the viscosity retention rate (relative value of the viscosity on the 30th day when the viscosity on the 7th day was 100%) was calculated from the viscosity.
  • the viscosity was measured using a BH type rotational viscometer. Assuming that the rotation speed of the spindle rotor was 20 rotations per minute, the viscosity value 1 minute after the start of rotation of the rotor was read at 25 ° C. Rotor No. 5, No. 6 or No. 7 was used. Before the viscosity measurement, each viscous composition was defoamed by centrifugation (2000 rpm ⁇ 10 to 20 minutes) before use.
  • a viscosity retention rate of 80% or more was evaluated as ⁇ , 70% or more and less than 80% was evaluated as ⁇ , and a viscosity retention rate of less than 70% was evaluated as ⁇ .
  • the evaluation is also shown in Table 1.
  • ⁇ Preparation and evaluation of chelating agent-containing composition Preparation of aqueous chelating agent Using a precision balance in a 100 ml plastic bottle, measure various chelating agents and ion-exchanged water so that the concentration of the chelating agent is 0.1% by mass, and stir with a stirrer until uniform. A 0.1% aqueous chelating agent solution was obtained.
  • the chelating agents used were pentetic acid, phytic acid, etidronic acid, citric acid, sodium pentetate, and sodium hexametaphosphate.
  • viscous compositions contain 25 ppm of a chelating agent.
  • the same operation was carried out using ion-exchanged water instead of the 0.1 mass% chelating agent aqueous solution to obtain 100 g of a viscous composition (Comparative Example 1a: blank).
  • compositions of the obtained compositions are summarized in Tables 2 and 3.
  • Each viscous composition was stored at 50 ° C. and the viscosity was measured every few days. Further, the viscosity retention rate (relative value of the viscosity on the 30th day when the viscosity on the 7th day was 100%) was calculated from the viscosity.
  • the viscosity was measured using a BH type rotational viscometer. Assuming that the rotation speed of the spindle rotor was 20 rotations per minute, the viscosity value 1 minute after the start of rotation of the rotor was read at 25 ° C. Rotor No. 5, No. 6 or No. 7 was used. Before the viscosity measurement, each viscous composition was defoamed by centrifugation (2000 rpm ⁇ 10 to 20 minutes) before use. The results are shown in FIG.
  • a viscosity retention rate of 80% or more was evaluated as ⁇
  • 70% or more and less than 80% was evaluated as ⁇
  • a viscosity retention rate of less than 70% was evaluated as ⁇ .
  • the evaluation is also shown in Tables 2 and 3.
  • the types of chelating agents shown in Tables 2 and 3 and the types of chelating agents shown in FIG. 1 are the same. By comparing these types, each graph in FIG. 1 can be used in any of the examples or comparative examples. Understand if this is the case.
  • the composition contains a polymer obtained by polymerizing a water-soluble unsaturated carboxylic acid monomer in the presence of water-soluble sucrose allyl ether, O / W further containing a chelating agent. It was found that the emulsion composition suppressed the decrease in viscosity over time.
  • aqueous composition containing various chelating agents (pentetic acid, phytic acid, etidronic acid, citric acid, 5 sodium pentetate, or sodium hexametaphosphate) was prepared as follows.
  • the obtained aqueous dispersion composition of Polymer 1 and the aqueous chelating agent composition were stirred using a stirrer until uniform to obtain an aqueous solution composition for study.
  • the concentration of various chelating agents in the aqueous solution composition for study was adjusted to 25 ppm.
  • the obtained aqueous solution compositions for examination were stored at 50 ° C., and the viscosities were measured on the 0th and 30th days. Further, the viscosity retention rate (relative value of the viscosity on the 30th day when the viscosity on the 0th day was 100%) was calculated from the viscosity.
  • the viscosity was measured using a BH type rotational viscometer. Assuming that the rotation speed of the spindle rotor was 20 rotations per minute, the viscosity value 1 minute after the start of rotation of the rotor was read at 25 ° C. Rotor No. 5, No. 6 or No. 7 was used. Before the viscosity measurement, each viscous composition was defoamed by centrifugation (2000 rpm ⁇ 10 to 20 minutes) before use.

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  • Health & Medical Sciences (AREA)
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  • Polymers & Plastics (AREA)
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Abstract

L'invention concerne une composition dans laquelle la réduction de la viscosité au cours du temps est supprimée, la composition contenant un polymère obtenu par polymérisation d'un monomère d'acide carboxylique insaturé soluble dans l'eau en présence d'un éther d'allyle de saccharose soluble dans l'eau. Plus particulièrement, l'invention concerne une composition d'émulsion d'huile dans l'eau contenant : (A) un polymère obtenu par polymérisation d'un monomère d'acide carboxylique insaturé soluble dans l'eau en présence d'un éther d'allyle de saccharose soluble dans l'eau et (B) un agent chélatant.
PCT/JP2021/010730 2020-03-31 2021-03-17 Composition visqueuse WO2021200137A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS62289505A (ja) * 1986-05-27 1987-12-16 ザ　ブ−ツ　カンパニ−　ピ−エルシ− 昆虫防除用組成物
JPH08245348A (ja) * 1995-02-22 1996-09-24 Wella Ag 毛髪染色剤
JPH10513199A (ja) * 1995-02-10 1998-12-15 ザ、プロクター、エンド、ギャンブル、カンパニー パーソナルケア組成物および該組成物を含有する拭い製品
JP2001516704A (ja) * 1997-09-17 2001-10-02 ザ、プロクター、エンド、ギャンブル、カンパニー 陰イオン性光学的明色化剤を含むヘアスタイリング組成物
JP2015224326A (ja) * 2014-05-29 2015-12-14 住友精化株式会社 超音波媒体用組成物

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS62289505A (ja) * 1986-05-27 1987-12-16 ザ　ブ−ツ　カンパニ−　ピ−エルシ− 昆虫防除用組成物
JPH10513199A (ja) * 1995-02-10 1998-12-15 ザ、プロクター、エンド、ギャンブル、カンパニー パーソナルケア組成物および該組成物を含有する拭い製品
JPH08245348A (ja) * 1995-02-22 1996-09-24 Wella Ag 毛髪染色剤
JP2001516704A (ja) * 1997-09-17 2001-10-02 ザ、プロクター、エンド、ギャンブル、カンパニー 陰イオン性光学的明色化剤を含むヘアスタイリング組成物
JP2015224326A (ja) * 2014-05-29 2015-12-14 住友精化株式会社 超音波媒体用組成物

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