WO2024004982A1 - アルコール含有粘性組成物 - Google Patents

アルコール含有粘性組成物 Download PDF

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Publication number
WO2024004982A1
WO2024004982A1 PCT/JP2023/023722 JP2023023722W WO2024004982A1 WO 2024004982 A1 WO2024004982 A1 WO 2024004982A1 JP 2023023722 W JP2023023722 W JP 2023023722W WO 2024004982 A1 WO2024004982 A1 WO 2024004982A1
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Prior art keywords
polymer
mass
viscous composition
ethanol
alcohol
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English (en)
French (fr)
Japanese (ja)
Inventor
真智子 中川
美来 田口
友佳 境
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Sumitomo Seika Chemicals Co Ltd
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Sumitomo Seika Chemicals Co Ltd
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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
    • C08F20/06—Acrylic acid; Methacrylic acid; 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
    • 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
    • C08F20/10—Esters
    • C08F20/12—Esters of monohydric alcohols or phenols
    • C08F20/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F20/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic 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
    • C08K5/04—Oxygen-containing compounds
    • C08K5/05—Alcohols; Metal alcoholates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/05—Alcohols; Metal alcoholates
    • C08K5/053—Polyhydroxylic alcohols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • 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
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/52—Natural or synthetic resins or their salts
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere

Definitions

  • the present disclosure relates to alcohol-containing viscous compositions and the like.
  • Alcohol-containing viscous compositions are widely used in various fields.
  • the present inventors conducted repeated studies in order to obtain an alcohol viscous composition that has a high alcohol content concentration and exhibits good viscosity while containing a synthetically obtained polymer as a thickener.
  • the present inventors discovered the possibility that a viscous composition containing specific amounts of a specific polymer and a specific alcohol could become an alcoholic viscous composition exhibiting good viscosity, and conducted further studies.
  • Item 1 A viscous composition containing (a) 0.5 to 25% by mass of a polymer having (meth)acrylic acid as a constituent unit, and (b) a solvent having an alcohol concentration of 82% by mass or more.
  • Item 2. The viscous composition according to item 1, which has a pH of less than 7 at 25°C.
  • the (a) polymer is (A) At least one polymer selected from the group consisting of the following (A-0), (A-1), and (A-2): (A-0) A polymer obtained by polymerizing the following (i) (A-1) A copolymer obtained by polymerizing the following (i) and (ii) (A-2) A copolymer obtained by polymerizing the following (i) ), (ii), and (iii) (i) 100 parts by mass of (meth)acrylic acid (ii) 1 part by mass or less of a compound having two or more ethylenically unsaturated groups (iii ) 5 parts by mass or less of a (meth)acrylic acid alkyl ester whose alkyl group has 10 to 30 carbon atoms; Item 2.
  • Section 7. Items 1 to 6, wherein the alcohol is at least one selected from the group consisting of monovalent or divalent alkyl alcohol having 1 to 6 carbon atoms, glycerin, 2-phenoxyethanol, benzyl alcohol, and furfuryl alcohol.
  • Section 8. The alkyl alcohol is at least one selected from the group consisting of methanol, ethanol, n-propanol, isopropanol, n-butanol, ethylene glycol, propylene glycol, 1,3-butanediol, and pentylene glycol. 7.
  • Item 9. Item 9.
  • An alcoholic viscous composition that has a high alcohol content concentration and exhibits good viscosity even though it contains a synthetically obtained polymer as a thickener.
  • the viscous composition preferably also exhibits good transparency (transmittance).
  • Ethanol solutions (I) and (II) of each polymer were prepared, and the transmittance was measured using these ethanol solutions as samples. The results are shown below.
  • the present disclosure preferably includes, but is not limited to, alcohol-containing viscous compositions, etc., and the present disclosure includes all disclosed herein and recognizable to those skilled in the art.
  • the alcohol-containing viscous composition included in the present disclosure includes (a) 0.5 to 25% by mass of a polymer having (meth)acrylic acid as a constituent unit, and (b) a solvent having an alcohol concentration of 82% by mass or more. , contains.
  • the viscous composition included in the present disclosure may be referred to as the composition of the present disclosure.
  • (meth)acrylic means acrylic and/or methacryl.
  • (meth)acrylic acid either acrylic acid or methacrylic acid may be used alone, or both may be used in combination.
  • the polymer (a) is a polymer containing (meth)acrylic acid as a constituent unit, and is more preferably a group consisting of the following (A-0), (A-1), and (A-2). At least one kind of polymer selected from the following.
  • the content of (a) is 0.5 to 25% by mass based on the viscous composition.
  • the upper and lower limits of the range are, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, It may be 22, 23, or 24% by weight.
  • the range is preferably 1 to 20% by weight.
  • the polymer (A-0), the copolymer (A-1), and the copolymer (A-2) were prepared as follows. It is sometimes called merging (A-2).
  • the polymer (a), including polymer (A-0), polymer (A-1), and polymer (A-2), is a carboxyl group-containing water-soluble polymer.
  • a carboxyl group-containing water-soluble polymer is a compound in which the carboxyl group contained in the polymer is not neutralized (unneutralized compound), or a part of the carboxyl group contained in the polymer, Alternatively, it also includes compounds that are completely neutralized (neutralized compounds).
  • the polymer (A-1) and the polymer (A-2) are polymers obtained by polymerizing (meth)acrylic acid and a compound (crosslinking agent) having two or more ethylenically unsaturated groups.
  • a compound in which (meth)acrylic acid is crosslinked with a compound having two or more ethylenically unsaturated groups are compounds in which, in addition to (meth)acrylic acid, a compound having two or more ethylenically unsaturated groups is also polymerized (in other words, ( meth)acrylic acid polymer is crosslinked with the compound).
  • the amount of the above (ii) used is 1 part by mass or less, preferably 0.01 to 1.0 parts by mass, more preferably 0.01 to 0.7 parts by mass, per 100 parts by mass of (meth)acrylic acid. preferable.
  • the amount of the above (iii) used is 5 parts by mass or less, preferably 0.01 to 5 parts by mass, and more preferably 0.01 to 4 parts by mass, based on 100 parts by mass of (meth)acrylic acid.
  • Examples of the above (ii) include pentaerythritol tetraallyl ether, N,N'-methylenebisacrylamide, ethylene glycol dimethacrylate, ethylene glycol diglycidyl ether, polyethylene glycol dimethacrylate, polyethylene glycol diglycidyl ether, and the like.
  • (ii) is a compound that can act as a crosslinking agent.
  • (ii) can be used alone or in combination of two or more.
  • the above (iii) is an ester of (meth)acrylic acid and a higher alcohol whose alkyl group has 10 to 30 carbon atoms.
  • the number of carbon atoms in the alkyl group is preferably 12 to 30, 14 to 28, 16 to 26, or 18 to 24, for example.
  • Examples of such (meth)acrylic acid alkyl esters include stearyl methacrylate, eicosanyl methacrylate, behenyl methacrylate, and tetracosanyl methacrylate. These (meth)acrylic acid alkyl esters may be used alone or in combination of two or more.
  • a commercially available product such as Bremmer VMA70 (trade name, manufactured by NOF Corporation) may be used.
  • the polymer (a) is a polymer having (meth)acrylic acid as a constituent unit, and is therefore a polymer obtained using (meth)acrylic acid as a monomer.
  • the polymer (A-0) includes polyacrylic acid, polymethacrylic acid, and a copolymer of acrylic acid and methacrylic acid.
  • polymers (A-1) and (A-2) are obtained by polymerizing at least (meth)acrylic acid and a compound having two or more ethylenically unsaturated groups. These polymerizations are preferably carried out in a polymerization solvent in the presence of a radical polymerization initiator.
  • a method for polymerizing only (i), (i) and (ii), or (i), (ii), and (iii) is a method of polymerizing these in a polymerization solvent in the presence of a radical polymerization initiator. are preferred. This will be explained in more detail below.
  • radical polymerization initiator ⁇ , ⁇ '-azobisisobutyronitrile, 2,2'-azobis-2,4-dimethylvaleronitrile, 2,2'-azobismethylisobutyrate, 2,2 Examples include '-azobis(2-methylpropionamidine) dihydrochloride, benzoyl peroxide, lauroyl peroxide, cumene hydroperoxide, and tertiary butyl hydroperoxide. These radical polymerization initiators may be used alone or in combination of two or more.
  • the amount of the radical polymerization initiator used is preferably 0.01 to 0.45 parts by mass, more preferably 0.01 to 0.4 parts by mass, per 100 parts by mass of (meth)acrylic acid.
  • any of the polymers (A-0), (A-1), and (A-2) can be preferably prepared, for example, by precipitation polymerization or reversed-phase suspension polymerization. Furthermore, the precipitation polymerization may be carried out in a polymerization solvent containing a nonionic surfactant having a polyoxyethylene chain.
  • nonionic surfactant having a polyoxyethylene chain examples include polyhydric alcohol fatty acid ester ethylene oxide adducts, block copolymers of hydroxy fatty acids and ethylene oxide, and polyoxyethylene castor oil.
  • ester compounds of polyoxyethylene hydrogenated castor oil and polyhydric alcohol fatty acid are preferably mentioned.
  • polyhydric alcohol fatty acid saturated or unsaturated polyhydric (especially dihydric) alcohol fatty acids having 14 to 24 carbon atoms are preferable, and more specifically, isopalmitic acid, isostearic acid, isooleic acid etc. are preferably mentioned.
  • the average number of moles of ethylene oxide added to polyoxyethylene is about 20 to 100, or about 30 to 70.
  • a particularly preferred ester compound of polyoxyethylene hydrogenated castor oil and polyhydric alcohol fatty acid is polyoxyethylene hydrogenated castor oil isostearate.
  • the polyoxyethylene castor oil preferably has an added mole number of ethylene oxide of about 2 to 10, more preferably about 2 to 5.
  • the block copolymer of hydroxy fatty acid and ethylene oxide can be said to be a copolymer consisting of polyhydroxy fatty acid and polyoxyethylene.
  • the fatty acid of the polyhydroxy fatty acid is preferably a fatty acid having about 14 to 22 carbon atoms, and preferred examples include myristic acid, palmitic acid, stearic acid, etc., and examples of the hydroxy fatty acid include hydroxymyristic acid, hydroxypalmitic acid, hydroxystearic acid, etc. are preferred, with hydroxystearic acid being particularly preferred.
  • As the hydroxystearic acid 12-hydroxystearic acid is particularly preferred.
  • polyhydroxy fatty acid polyhydroxystearic acid is particularly preferred.
  • As the block copolymer of hydroxy fatty acid and ethylene oxide a block copolymer of 12-hydroxystearic acid and ethylene oxide is particularly preferred.
  • the nonionic surfactants having polyoxyethylene chains can be used alone or in combination of two or more.
  • the amount of the nonionic surfactant having a polyoxyethylene chain used is preferably 0.5 to 10 parts by weight, more preferably 1 to 7.5 parts by weight, based on 100 parts by weight of (meth)acrylic acid.
  • the polymerization solvent is preferably a solvent that dissolves (i), (ii), and (iii) but does not dissolve the obtained polymer.
  • Specific examples of such polymerization solvents include normal pentane, normal hexane, normal heptane, normal octane, isooctane, cyclopentane, methylcyclopentane, cyclohexane, methylcyclohexane, benzene, toluene, xylene, chlorobenzene, ethylene dichloride, and ethyl acetate. , isopropyl acetate, ethyl methyl ketone, isobutyl methyl ketone and the like.
  • polymerization solvents ethylene dichloride, n-hexane, n-heptane, and ethyl acetate are preferred from the viewpoint of stable quality and easy availability.
  • These polymerization solvents may be used alone or in combination of two or more.
  • the amount of the polymerization solvent used is preferably 200 to 10,000 parts by mass, more preferably 300 to 2,000 parts by mass, per 100 parts by mass of (meth)acrylic acid.
  • an inert gas atmosphere such as nitrogen gas or argon gas can be mentioned.
  • the reaction temperature when carrying out the above polymerization reaction is preferably 50 to 90°C, more preferably 55 to 75°C.
  • the reaction time when carrying out the above polymerization reaction is usually 2 to 10 hours.
  • the fine powder polymer can be isolated by heating the reaction solution to 80 to 120°C and removing the polymerization solvent.
  • the viscous composition of the present disclosure contains (b) a solvent with an alcohol concentration of 82% by mass or more. This means that alcohol is 82% by mass or more (that is, 82% by mass or more and 100% by mass or less) when the total amount of solvent contained in the viscous composition is 100% by mass.
  • the alcohol concentration is preferably 83% by mass or more, and may be 84% by mass or more.
  • the alcohol content in the viscous composition of the present disclosure is more than 60.75% by mass and 99.5% by mass or less, preferably 61 to 99.5% by mass.
  • the upper or lower limit of the range is, for example, 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, 93, 94, 95, 96, 97, 98, or 99% by mass.
  • the range may be 70-98% by weight.
  • the viscous composition of the present disclosure can be prepared, for example, by first preparing an alcohol aqueous solution, adding the polymer (a) to the aqueous solution, and adding a pH adjuster and other components as necessary. can.
  • alcohol preferred examples include straight chain or branched alkyl alcohols having 1 to 6 carbon atoms.
  • monovalent or divalent alkyl alcohols are preferred. More specifically, for example, methanol, ethanol, n-propanol, isopropanol, n-butanol, ethylene glycol, propylene glycol, 1,3-butanediol, and pentylene glycol are preferred, and ethanol is particularly preferred.
  • glycerin, 2-phenoxyethanol, benzyl alcohol, furfuryl alcohol, etc. can also be preferably used. One kind of alcohol can be used alone or two or more kinds can be used in combination.
  • the pH of the viscous composition of the present disclosure is preferably less than 7, more preferably 2 to 6.9.
  • the upper or lower limit of the range is, for example, 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2.9, 3, 3.1, 3.2, 3.3, 3.4, 3.5, 3.6, 3.7, 3.8, 3.9, 4, 4.1, 4.2, 4.3, 4.4, 4.5, 4.6, 4.7, 4.8, 4.9, 5, 5.1, 5.2, 5.3, 5.4, 5.5, 5.6, 5.7, It may be 5.8, 5.9, 6, 6.1, 6.2, 6.3, 6.4, 6.5, 6.6, 6.7, or 6.8.
  • the range is preferably 2.5 to 5.5.
  • the pH is a value measured with a pH meter at 25° C. (a displayed value when measured with a pH meter at 25° C. in the same manner as the pH measurement of an aqueous solution).
  • a viscous composition having a pH of 7 or higher can also be prepared by further adding, for example, a pH adjuster or the like to the viscous composition of the present disclosure having a pH within this range. Even if the pH is set to 7 or more, the effects of the viscous composition of the present disclosure are not likely to be impaired, and therefore, the viscous composition of the present disclosure having a pH within this range is also preferable for preparing a viscous composition having a pH of 7 or more. Can be used.
  • the transmittance of ethanol solution (II) is lower than that of ethanol solution (I), but the transmittance of ethanol solution (II) is It can be said that it is not extremely low.
  • the transmittance of the ethanol solution (I) is high, not only when the slope of the straight line is a positive number, but also when the slope of the straight line is about -1 to 0. It can be said that the transmittance of II) is also sufficiently high.
  • the transmittance of ethanol solution (I) is 80% or more (more preferably 85% or more, even more preferably 90% or more), if the slope of the straight line is -1 or more, ethanol (II) It can be said that the transmittance of is also sufficiently high. In this case, it is particularly preferable that the slope of the straight line is, for example, about -1 to 1.
  • the transmittance is the value obtained by placing the ethanol solution (I) or (II) in a cell with an optical path length of 1 cm and measuring the transmittance at a measurement wavelength of 425 nm using a spectrophotometer (the transmittance of distilled water is assumed to be 100%). ratio).
  • both ethanol solutions (I) and (II) can be prepared, and the transmittance of ethanol solution (II) is lower than that of ethanol solution (I). ), it can be said that it needs to be a polymer that has a high transmittance.
  • the ⁇ is preferably 0.5 to 10.
  • the upper and lower limits of the range are, for example, 1, 1.5, 2, 2.5, 3, 3.5, 4, 4.5, 5, 5.5, 6, 6.5, 7, 7.5, It may be 8, 8.5, 9, or 9.5.
  • ⁇ is more preferably from 1 to 10, and even more preferably from 1.5 to 8.
  • ⁇ is not particularly limited, but is preferably a positive number, for example, preferably from 10 to 90, more preferably from 15 to 80.
  • the viscous composition of the present disclosure may contain a pH adjuster, as described above.
  • Preferred examples of the pH adjuster include organic amines.
  • Preferred organic amines include di-(2-ethylhexyl)amine, triamylamine, diisopropanolamine, 2-amino-2-methyl-1-propanol (AMP), and triethanolamine.
  • Such pH adjusters can be used alone or in combination of two or more.
  • organic acids e.g. citric acid, etc.
  • salts thereof e.g. alkali metal salts
  • inorganic acids e.g. phosphoric acid
  • salts thereof e.g. alkali metal salts
  • the composition of the present disclosure does not contain organic acids and their salts and/or inorganic acids and their salts.
  • the viscous composition of the present disclosure may contain components other than the above-mentioned components as long as the effects are not impaired.
  • examples of such other components include various components used in the field of external compositions.
  • the viscous composition of the present disclosure preferably has a viscosity of 1000 mPa ⁇ s or more, more preferably about 1000 to 150000 mPa ⁇ s.
  • the upper and lower limits of the range are, for example, 1500, 2000, 2500, 3000, 3500, 4000, 4500, 5000, 5500, 6000, 6500, 7000, 7500, 8000, 8500, 9000, 9500, 10000, 15000, 20000, 25000, 30000, 35000, 40000, 45000, 50000, 55000, 60000, 65000, 70000, 75000, 80000, 85000, 90000, 95000, 100000, 110000, 120000, 130000, or 140000mPa ⁇ It may be s.
  • the range may be 1500 to 140000 mPa ⁇ s.
  • the viscosity value was determined by measuring the viscosity of the viscous composition at 25° C. after 1 minute using a BrookField viscometer (model number: DV1MRVTJ0) at a rotational speed of 20 revolutions per minute.
  • the viscous composition of the present disclosure preferably has a transmittance of 30% or more, more preferably 40, 50, or 60% or more, and even more preferably 70% or more.
  • a transmittance is a value obtained by placing the viscous composition in a cell with an optical path length of 1 cm and measuring the transmittance at a measurement wavelength of 425 nm using a spectrophotometer (ratio when the transmittance of distilled water is taken as 100%).
  • the viscous composition of the present disclosure can be used, for example, as an adhesive, a pressure-sensitive adhesive, a binder, a friction reducing agent, a film forming agent, a cleaning agent, a polishing liquid, an antiviral agent, a disinfectant, a disinfectant, and an insect repellent.
  • various coating fluids paints, inks, etc.
  • various sheet materials cosmetic packs, cosmetic gel sheets, medical gel sheets, moisturizing gel sheets, various pads, etc.
  • house cleaning agents paint film strippers, etc.
  • Cosmetics include hair cosmetics, and more specifically, they can be used as astringent lotions, sensitizers, antiperspirants, hair styling products, perfumes, nail products, sunscreens, peeling gels, and the like. It can also be preferably used, for example, for the preparation and manufacture of building materials, gas separation membranes, medical devices, diagnostic agents, and the like. Alternatively, it can also be preferably used as a composition for external use.
  • the present disclosure also provides (b) a thickener for thickening a solvent having an alcohol concentration of 82% by mass or more to prepare a viscous composition preferably having a pH of less than 7 at 25°C, (a) Thickeners including polymers having (meth)acrylic acid as a constituent unit are also preferably included.
  • the explanations regarding the viscous composition of the present disclosure also apply to the (b) solvent and (a) polymer in the thickener.
  • the term “comprising” includes “consisting essentially of” and “consisting of.” Additionally, the present disclosure encompasses any and all combinations of the features described herein.
  • Polymer production example 1 In a 500 mL four-necked flask equipped with a stirrer, thermometer, nitrogen blowing tube, and condenser, 45 g of acrylic acid, 0.13 g of pentaerythritol tetraallyl ether, 150 g of n-hexane, and 2,2'-azobismethyl were added. 0.153 g of isobutyrate was added to prepare a reaction solution. After the solution was stirred to mix uniformly, nitrogen gas was blown into the solution to remove oxygen present in the head space of the reaction vessel, the raw materials, and the solvent. Next, the reaction solution was maintained at 60 to 65° C. and reacted for 4 hours under a nitrogen atmosphere.
  • the resulting slurry was heated to 90°C to distill off n-hexane, and then dried under reduced pressure at 110°C and 10 mmHg for 8 hours to form a (meth)acrylic acid-based water-soluble polymer. 42 g of a certain acrylic acid polymer was obtained.
  • the polymer may be referred to as Production Example 1 polymer.
  • the resulting slurry was heated to 90°C to distill off n-hexane, and further dried under reduced pressure at 110°C and 10 mmHg for 8 hours to obtain a white fine powder containing alkyl-modified carboxyl groups. 43 g of copolymer was obtained.
  • the copolymer may be referred to as Production Example 3 polymer.
  • the preparation was carried out under the following conditions using a beaker with a capacity of 200 mL, a bottom diameter of 6 cm, and a stirrer with 4 paddles of 5 cm diameter.
  • a viscous composition with a polymer concentration of 5% was prepared by stirring at 500 rpm to 850 rpm for 1 hour (can be extended to 2 hours if not dissolved).
  • a viscous composition with a polymer concentration of 10% was prepared by stirring for 1 hour at 1200 rpm (the rotation speed may be lowered if the composition wraps around the shaft due to high viscosity).
  • a lid or the like was used to prevent evaporation of the solvent. More specifically, it was performed as follows.
  • Ethanol manufactured by Kishida Chemical Co., Ltd., ethanol (99.5) (purity 99.5%) is measured into a 200 ml beaker and stirred at 500 rpm using a stirrer with 4 paddles of ⁇ 5 cm. Polymer was added to. After adding the polymer, the mixture was stirred at 700 rpm for 60 minutes to prepare a viscous composition.
  • Example 2 Ethanol was measured into a beaker with a capacity of 200 ml, and the polymer was added while stirring at 500 rpm using a stirrer with 4 paddles of ⁇ 5 cm. After adding the polymer, the mixture was stirred at 1200 rpm for 60 minutes to prepare a viscous composition.
  • Example 3 Ethanol and ion-exchanged water were placed in a 200 ml beaker to prepare an ethanol aqueous solution. This was stirred at 500 rpm using a stirrer with 4 paddles of ⁇ 5 cm, and each polymer was added thereto. After adding the polymer, the mixture was stirred at 1200 rpm for 60 minutes to prepare a viscous composition.
  • Ethanol or IPA manufactured by Nacalai Tex Co., Ltd., 2-propanol (purity 99.7%) was measured into a 200 ml beaker, and the mixture was stirred at 500 rpm using a stirrer with 4 paddles of ⁇ 5 cm.
  • a viscous composition was prepared by adding the polymer and stirring for 60 minutes.
  • Example 6, 7 In a beaker with a capacity of 200 ml, add 1,3-butanediol (manufactured by Kanto Kagaku Co., Ltd., 1,3-butanediol (purity 98.0%)) or propylene glycol (manufactured by Kanto Kagaku Co., Ltd., propylene glycol (purity 99.0%)). )) was weighed and stirred at 500 rpm using a stirrer with 4 paddles of ⁇ 5 cm, and the polymer was added thereto. After adding the polymer, the mixture was stirred at 1000 rpm for 120 minutes to prepare a viscous composition.
  • 1,3-butanediol manufactured by Kanto Kagaku Co., Ltd., 1,3-butanediol (purity 98.0%)
  • propylene glycol manufactured by Kanto Kagaku Co., Ltd., propylene glycol (purity 99.0%)
  • Example 8 Ethanol was measured into a beaker with a capacity of 200 ml, and the polymer was added while stirring at 500 rpm using a stirrer with 4 paddles of ⁇ 5 cm. After adding the polymer, the mixture was stirred at 750 rpm for 60 minutes to prepare a viscous composition.
  • Example 13 Ethanol was measured into a beaker with a capacity of 200 ml, and the polymer was added while stirring at 500 rpm using a stirrer with 4 paddles of ⁇ 5 cm. After adding the polymer, the mixture was stirred at 850 rpm for 90 minutes to prepare a viscous composition.
  • a viscous composition was prepared in the following manner. That is, ethanol and ion-exchanged water were placed in a 200 ml beaker to prepare an ethanol aqueous solution. While this was being stirred at 500 rpm using a stirrer with 4 paddles each having a diameter of 5 cm, 0.5 g of the polymer of Production Example 1 was added. After the polymer was added, the mixture was stirred at 900 rpm for 60 minutes.
  • AMP manufactured by ANGUS CHEMICAL, 2-amino-2-methyl-1-propanol (purity 99.5)
  • ethanol diluted with ethanol to make a 25% AMP ethanol solution
  • the mixture was stirred for several minutes to prepare a viscous composition.
  • the viscous composition was analyzed in the same manner as above, it was found to have a pH of 11.0, a viscosity of 6120 mPa ⁇ s, and a transmittance of 93.7%.

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010047554A (ja) * 2008-08-25 2010-03-04 Niitaka:Kk アルコールジェル消毒剤組成物
JP2017088679A (ja) * 2015-11-05 2017-05-25 エステー株式会社 アルコール系ゲル状組成物およびその製造法
WO2020179602A1 (ja) * 2019-03-01 2020-09-10 住友精化株式会社 ポリマー水分散組成物
WO2020226040A1 (ja) * 2019-05-09 2020-11-12 住友精化株式会社 粘性組成物

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010047554A (ja) * 2008-08-25 2010-03-04 Niitaka:Kk アルコールジェル消毒剤組成物
JP2017088679A (ja) * 2015-11-05 2017-05-25 エステー株式会社 アルコール系ゲル状組成物およびその製造法
WO2020179602A1 (ja) * 2019-03-01 2020-09-10 住友精化株式会社 ポリマー水分散組成物
WO2020226040A1 (ja) * 2019-05-09 2020-11-12 住友精化株式会社 粘性組成物

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