Composition containing vinyl alcohol polymer and method for separating vinyl alcohol polymer

Abstract

Provided is a composition comprising a vinyl alcohol-based polymer, the composition being homogenous when formed into an aqueous solution, and the vinyl alcohol-based polymer contained in the aqueous solution being easily separated therefrom. The composition comprises: a vinyl alcohol-based polymer (A) having a peak top retention time RT of 22 minutes or longer as measured by reversed-phase partition gradient high-performance liquid chromatography using a water-ethanol eluent; and a compound (B), the compound (B) being represented by formula (1). In formula (1), X represents an oxygen atom or the like. Y represents an atomic group having 1-10 carbon atoms. Z represents one type selected from a carboxyl group, a sulfo group, a phosphate group, salts thereof, and anions thereof. R1 represents an acyl group or a hydrocarbon group.

Description

[Technical Field]

[0001] The present invention relates to a composition containing a vinyl alcohol polymer and a method for separating a vinyl alcohol polymer. [Background technology]

[0002] Vinyl alcohol polymers (hereinafter sometimes referred to as "PVA") are widely used as thickeners, paper coating agents, adhesives, fiber processing agents, binders, emulsion stabilizers, and raw materials for films and fibers. When PVA is used for these applications, it is sometimes used in the form of an aqueous solution in which PVA is dissolved in water. While this aqueous PVA solution is generally prepared by mixing PVA with water and heating the mixture, highly hydrophobic PVA usually cannot be dissolved in water by this method. However, it is known that an aqueous solution can be prepared by adding an anionic surfactant (Patent Document 1). This is due to the formation of a complex between the highly hydrophobic PVA and the anionic surfactant in water (Non-Patent Document 1). [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Application Publication No. 53-133252 [Non-patent literature]

[0004] [Non-Patent Document 1] Shuji Saito, "Complexes of Polymeric Substances and Surfactants," Oil Chemistry, Vol. 12, No. 3, 1963, pp. 133-141 Summary of the Invention [Problem to be solved by the invention]

[0005] However, no PVA-containing composition is known that allows easy separation and extraction of PVA from a prepared aqueous PVA solution. An object of the present invention is to provide a PVA-containing composition that, when prepared as an aqueous solution, is homogeneous and allows easy separation of the PVA contained in the aqueous solution. Another object of the present invention is to provide a method for separating PVA. Note that "a homogeneous aqueous solution" may mean a state in which the PVA is uniformly dissolved. [Means for solving the problem]

[0006] As a result of intensive research to solve the above-mentioned problems, the present inventors discovered that a composition containing a specific PVA and a compound having a specific structure can solve the above-mentioned problems, and thus completed the present invention. That is, the present invention is [1] A composition comprising a vinyl alcohol polymer (A) having a peak top retention time (RT) of 22 minutes or longer as measured by reversed-phase gradient high-performance liquid chromatography using a water-ethanol eluent, and a compound (B), wherein the compound (B) is a compound represented by formula (1); [ka] [In formula (1), X represents an oxygen atom, a group represented by the following formula (2), or a group represented by the following formula (3). Y represents an atomic group having 1 to 10 carbon atoms. Z represents one selected from the group consisting of a carboxy group, a sulfo group, a phosphate group, salts thereof, and anions thereof. R 1 represents an acyl group or a hydrocarbon group.] [ka] [ka] [In formula (2) and formula (3), R 2 , R 3 and R 4 each independently represents a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or a bond bonded to Y. * represents a bond.] [2] The composition of [1], wherein, in the compound (B), Z in formula (1) is a carboxy group, a salt of a carboxy group, or an anion of a carboxy group; [3] Regarding the compound (B), X in formula (1) is a group represented by formula (2), and R 1 the composition of [1] or [2], wherein [4] The composition according to any one of [1] to [3], wherein the compound (B) is at least one selected from the group consisting of N-acylamino acid salts and acyl lactate salts; [5] The composition according to [4], wherein the compound (B) is an N-acylamino acid salt; [6] The composition according to [5], wherein the N-acylamino acid salt has an acyl group derived from a saturated or unsaturated fatty acid having 8 to 20 carbon atoms; [7] In the compound (B), R 1 any one of the compositions [1] to [6], wherein [ka] [In formula (4), R 5 represents a saturated or unsaturated hydrocarbon group having 7 to 20 carbon atoms which may have a substituent. * represents a bond.] [8] The composition according to any one of [1] to [7], wherein the degree of saponification of the vinyl alcohol polymer (A) is 20 mol % or more and 70 mol % or less; [9] The composition of any one of [1] to [8], wherein the vinyl alcohol polymer (A) consists solely of monomer units derived from vinyl acetate;

[10] Any of the compositions [1] to [9], which is at least one selected from the group consisting of agricultural product compositions, automotive product compositions, aviation product compositions, industrial product compositions, livestock product compositions, marine product compositions, pharmaceutical compositions, personal care product compositions, recreational product compositions, and water treatment agent compositions;

[11] Any of the compositions [1] to

[10] , which is an aqueous solution further containing water;

[12] A method for separating a vinyl alcohol polymer, comprising adjusting the pH of the composition according to

[11] above to precipitate at least a part of the vinyl alcohol polymer (A) contained in the composition; Regarding. [Effects of the Invention]

[0007] When the composition of the present invention is prepared as an aqueous solution, the aqueous solution is homogeneous and the PVA contained in the aqueous solution can be easily separated. DETAILED DESCRIPTION OF THE INVENTION

[0008] Hereinafter, embodiments of the present invention will be described in detail. Note that the scope of the present invention is not limited to the embodiments described here, and various modifications can be made without departing from the spirit of the present invention.

[0009] <Composition> The composition of the present invention comprises a vinyl alcohol polymer (A) (hereinafter, sometimes referred to as "PVA (A)") having a peak top retention time (RT) of 22 minutes or longer as measured by reversed-phase partition gradient high-performance liquid chromatography using a water-ethanol eluent, and a compound (B), wherein the compound (B) is a compound represented by formula (1). [ka]

[0010] In formula (1), X represents an oxygen atom, a group represented by the following formula (2), or a group represented by the following formula (3). Y represents an atomic group having 1 to 10 carbon atoms. Z represents one selected from the group consisting of a carboxy group, a sulfo group, a phosphate group, salts thereof, and anions thereof. R 1 represents an acyl group or a hydrocarbon group. [ka] [ka]

[0011] In formula (2) and formula (3), R 2 , R 3 and R 4 each independently represents a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or a bond bonded to Y. * represents a bond. R 2 , R 3 or R 4 is a bond bonded to Y, X and Y form a ring structure.

[0012] The ratio of PVA (A) to compound (B) contained in the composition is preferably 99.9:0.1 to 80:20 by mass, but may also be 99:1 to 85:15, or 97:3 to 90:10. A ratio of 50:50 to 0.1:99.9 by mass may also be preferred. By keeping the ratio within this range, a more uniform solution can be obtained, even when preparing a highly concentrated aqueous solution of PVA (A), such as one with a concentration of 30% by mass.

[0013] There are no particular limitations on the suitable method for producing the composition, and any method can be used as long as it allows mixing of PVA (A) and compound (B). For example, PVA (A) and compound (B) may be mixed directly, or compound (B) may be added to a solution containing PVA (A), or PVA (A) may be added to a solution containing compound (B), or the composition may be produced by mixing a solution containing PVA (A) and a solution containing compound (B). For example, the composition of the present invention can be obtained by adding compound (B) to an aqueous solution of PVA (A).

[0014] (Vinyl alcohol polymer (A)) The PVA (A) contained in the composition of the present invention is a polymer having vinyl alcohol units as structural units. The lower limit of the proportion of vinyl alcohol units to all structural units in PVA (A) is preferably, for example, 10 mol%, more preferably 20 mol%, even more preferably 30 mol%, and even more preferably 40 mol% in some cases. On the other hand, the upper limit of the proportion of vinyl alcohol units is preferably, for example, 90 mol%, more preferably 80 mol%, and even more preferably 60 mol% in some cases. PVA (A) may be obtained, for example, by polymerizing a vinyl ester monomer and saponifying the obtained vinyl ester polymer, and PVA (A) may contain, for example, vinyl ester units in addition to vinyl alcohol units.

[0015] PVA (A) has a retention time (RT) of the peak top measured by reversed-phase partition gradient high-performance liquid chromatography with a water-ethanol eluent of 22 minutes or more. Here, the "peak top" is the point where the detection intensity in the chromatogram obtained by chromatographic measurement takes the maximum value and is a maximum value, and means the peak top derived from PVA (A). Such PVA has low water solubility and excellent separability from an aqueous solution. It is preferable that PVA (A) has a retention time RT exceeding 22 minutes. Also, it is preferable that PVA (A) has a retention time RT of 25 minutes or less, and PVA (A) with 22 minutes < RT < 25 minutes is more preferable. The retention time RT of PVA (A) can be adjusted by introducing a modifying group, adjusting the saponification degree, and the viscosity-average polymerization degree.

[0016] The retention time RT of the PVA (A) is measured under the following measurement conditions. <Measurement conditions> Column: Shimpack G-ODS(4) (manufactured by Shimadzu Corporation, octadecyl group-modified spherical fully porous silica gel, inner diameter 4 mm × length 10 mm, particle size 5 μm) Column temperature: 45 °C Eluent: A mixed solution of ion-exchanged water (X) and ethanol (purity 99.5%) (Y) Eluent composition for each measurement time; 0 to 5 minutes: (Y) Concentration constant at 5% by volume 5 to 25 minutes: (Y) concentration 5 to 100% by volume 25-40 min: (Y) concentration 100% by volume constant 40-41 min: (Y) concentration 100-5% by volume 41 to 55 minutes: (Y) concentration constant at 5% by volume (The (Y) concentration is gradually increased from 5% by volume to 100% by volume at a substantially constant rate between 5 and 25 minutes. The (Y) concentration is gradually decreased from 100% by volume to 5% by volume at a substantially constant rate between 40 and 41 minutes.) Mobile phase flow rate: 0.4mL / min Sample concentration: 5 mg / mL Detector: ELSD-LTII (Shimadzu Corporation, drift tube temperature 40°C, gain 6 (=32 times), N2 gas spray pressure primary 0.4 MPa, secondary 0.35 MPa, data acquisition interval: 1000 ms, filter: 1 sec.) Injection volume: 5μL Length from injection to column inlet: 900 mm Length from column outlet to nebulizer of ELSD-LTII detector: 1375 mm Pipe diameter: 0.3mm ID

[0017] The lower limit of the saponification degree of PVA (A) is preferably 20 mol%, more preferably 30 mol%, even more preferably 40 mol%, and even more preferably 45 mol%. The upper limit of the saponification degree of PVA (A) is preferably 90 mol%, more preferably 80 mol%, even more preferably 70 mol%, even more preferably 60 mol%, and particularly preferably 55 mol%. When the saponification degree of PVA (A) is within the above range, the separability from aqueous solution is more excellent. The saponification degree of PVA (A) is measured by the method described in JIS K6726:1994.

[0018] The lower limit of the viscosity-average degree of polymerization of PVA (A) is preferably 100, more preferably 200. The upper limit of the viscosity-average degree of polymerization of PVA (A) is preferably 3500, more preferably 2000, even more preferably 1000, even more preferably 500, and particularly preferably 300. When the viscosity-average degree of polymerization of PVA (A) is within the above range, the separability from the aqueous solution is more excellent. The viscosity-average degree of polymerization of PVA (A) is measured in accordance with JIS K6726:1994.

[0019] PVA (A) can be produced, for example, by saponifying a vinyl ester polymer obtained by polymerizing a vinyl ester monomer. Examples of vinyl ester monomers include vinyl formate, vinyl acetate, vinyl propionate, vinyl valerate, vinyl caprate, vinyl laurate, vinyl stearate, vinyl benzoate, vinyl butyrate, vinyl isobutyrate, vinyl pivalate, vinyl versatate, vinyl caproate, vinyl caprylate, vinyl caprate, vinyl laurate, vinyl palmitate, vinyl stearate, and vinyl oleate. Among these, vinyl acetate is preferred from the viewpoints of availability and economy. As the vinyl ester monomer, only one type may be used, or two or more types may be used in combination.

[0020] PVA (A) may be a polymer consisting solely of monomer units derived from vinyl ester monomers, or may be a polymer consisting solely of monomer units derived from vinyl acetate. However, even in this case, the terminal structure of PVA (A) may be a structure derived from a component other than vinyl ester monomers, such as a polymerization initiator or a chain transfer agent. PVA (A) may be a polymer consisting essentially solely of monomer units derived from vinyl ester monomers, or may be a polymer consisting essentially solely of monomer units derived from vinyl acetate. The monomer units derived from vinyl ester monomers may be vinyl alcohol units and vinyl ester units. The lower limit of the proportion of monomer units derived from vinyl ester monomers to all structural units in PVA (A) is preferably, for example, 90 mol%, and may be 95 mol%, 98 mol%, 99 mol%, 99.5 mol%, or 99.9 mol%. On the other hand, the upper limit of the proportion of monomer units derived from vinyl ester monomers may be 100 mol%. As described above, even if the ratio of monomer units derived from vinyl ester-based monomers to all structural units in PVA (A) is 100 mol %, the terminal structure of PVA (A) may be a structure derived from a monomer other than a vinyl ester-based monomer.

[0021] The PVA (A) may be a modified PVA into which units or functional groups other than units derived from vinyl ester monomers have been introduced by a method such as copolymerization, acetalization, or esterification.

[0022] When PVA (A) is a copolymer-modified PVA, the copolymer-modified PVA can be obtained, for example, by saponifying a vinyl ester copolymer obtained by copolymerizing a vinyl ester monomer with a monomer other than the vinyl ester monomer. The monomer other than the vinyl ester monomer to be copolymerized with the vinyl ester monomer can be any monomer copolymerizable with the vinyl ester monomer, and examples thereof include α-olefins such as propylene, 1-butene, isobutene, pentene, 1-hexene, 1-octene, 1-dodecene, 1-hexadecene, and 1-octadecene; (meth)acrylic acid esters such as methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, cyclohexyl (meth)acrylate, stearyl (meth)acrylate, and octadecyl (meth)acrylate; acrylamide derivatives such as N-methylacrylamide and N-ethylacrylamide; and N-methylmethacrylic acid. Examples of suitable monomers include amides, methacrylamide derivatives such as N-ethyl methacrylamide, vinyl ethers such as methyl vinyl ether, ethyl vinyl ether, n-propyl vinyl ether, isopropyl vinyl ether, n-butyl vinyl ether, lauryl vinyl ether, and vinyl ether stearate, allyl acetate, allyl ethers such as propyl allyl ether, butyl allyl ether, and hexyl allyl ether, monomers having an oxyalkylene group, isopropenyl acetate, and monomers having a silyl group such as vinylmethyldimethoxysilane, vinyldimethylmethoxysilane, vinyltriethoxysilane, vinylmethyldiethoxysilane, vinyldimethylethoxysilane, 3-(meth)acrylamidopropyltrimethoxysilane, and 3-(meth)acrylamidopropyltriethoxysilane. These may be used alone or in combination of two or more.

[0023] When PVA (A) is a modified PVA having a modifying group introduced by acetalization, the modifying agent used for the introduction of the modifying group by acetalization is not particularly limited, and examples thereof include linear, branched, cyclic saturated, cyclic unsaturated, or aromatic aldehydes and aldoses having 1 to 19 carbon atoms. Specific examples include formaldehyde, acetaldehyde, propionyl aldehyde, n-butyl aldehyde, isobutyl aldehyde, tert-butyl aldehyde, benzaldehyde, cyclohexyl aldehyde, pentanal, hexanal, heptanal, octanal, nonanal, decanal, dodecanal, tetradecanal, hexadecanal, and octadecanal. The modifying agent may have one or more hydrogen atoms substituted with a halogen or the like. The modifying agents may be used alone or in combination.

[0024] When PVA (A) is a modified PVA having a modifying group introduced by esterification, the modifier used to introduce the modifying group by esterification is not particularly limited, and examples thereof include carboxylic acid derivatives such as linear, branched, cyclic saturated, cyclic unsaturated, or aromatic carboxylic acids having 1 to 19 carbon atoms, carboxylic acid halides, vinyl esters, and fatty acids. Specific examples include acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, lauric acid, myristic acid, palmitic acid, margaric acid, stearic acid, and acid chlorides thereof. The modifier may also be one in which one or more hydrogen atoms have been substituted with a halogen or the like. The modifiers may be used alone or in combination.

[0025] PVA (A) can be produced by a conventionally known method. For example, methods for obtaining a vinyl ester polymer from a vinyl ester monomer include bulk polymerization, solution polymerization, suspension polymerization, emulsion polymerization, and dispersion polymerization. Among these, solution polymerization is industrially preferred.

[0026] A polymerization initiator may be used in the preparation of vinyl ester polymers. The polymerization initiator may be selected from known initiators depending on the polymerization method. Specific examples include azo initiators such as 2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), and 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile); percarbonate compounds such as diisopropyl peroxydicarbonate, di-2-ethylhexyl peroxydicarbonate, and diethoxyethyl peroxydicarbonate; perester compounds such as t-butyl peroxyneodecanate, α-cumyl peroxyneodecanate, and t-butyl peroxydecanate; acetylcyclohexylsulfonyl peroxide; and peroxide initiators such as 2,4,4-trimethylpentyl-2-peroxyphenoxyacetate.

[0027] The amount of the polymerization initiator may be appropriately determined depending on the type of monomer or initiator used, the desired degree of polymerization, etc., but is preferably 0.20 to 0.33% by mass based on the total mass of the vinyl ester monomers.

[0028] A chain transfer agent may be used in the preparation of a vinyl ester polymer. The chain transfer agent may be selected from known chain transfer agents depending on the polymerization method. Specific examples include aldehydes such as acetaldehyde and propionaldehyde; ketones such as acetone and methyl ethyl ketone; halogenated hydrocarbons such as trichloroethylene and perchloroethylene; and phosphinates such as sodium phosphinate monohydrate. Among these, aldehydes and ketones are preferred. The amount of the chain transfer agent is not particularly limited, as long as it can be determined to the intended degree of polymerization of the vinyl ester polymer depending on the chain transfer constant of the chain transfer agent added. Furthermore, functional groups may be introduced using such agents. For example, a chain transfer agent having an alkyl group may be used to introduce an aliphatic hydrocarbon group at the end, or a chain transfer agent having a carboxy group may be used to introduce an ionic functional group at the end.

[0029] The polymerization conditions and the like may be appropriately determined depending on the type and amount of the monomer used, the desired physical properties, the polymerization method employed, etc. For example, the polymerization temperature is usually 0 to 150°C, and preferably 20 to 120°C.

[0030] The polymerization rate of the vinyl ester polymer may be, for example, 20 to 95%. From the viewpoint of improving the yield and controlling the degree of polymerization, the polymerization rate is preferably 30% or more, and more preferably 40% or more.

[0031] The saponification reaction of the obtained vinyl ester polymer can be carried out by alcoholysis or hydrolysis using a conventionally known basic catalyst such as sodium hydroxide, potassium hydroxide, or sodium methoxide, or an acidic catalyst such as p-toluenesulfonic acid. Examples of solvents used in the saponification reaction include alcohols such as methanol and ethanol; esters such as methyl acetate and ethyl acetate; ketones such as acetone and methyl ethyl ketone; and aromatic hydrocarbons such as benzene and toluene. These solvents may be used alone or in combination of two or more. Among these, a preferred method is to use methanol or a mixed solution of methanol and methyl acetate as the solvent and carry out the saponification reaction in the presence of sodium hydroxide as a basic catalyst.

[0032] The amount of catalyst used in the saponification reaction may be appropriately determined depending on the type of catalyst used, the desired degree of saponification, etc. For example, when sodium hydroxide is used as the catalyst for the saponification reaction, in one embodiment of the present invention, the ratio (molar ratio) of the catalyst to the vinyl ester monomer in the vinyl ester copolymer is preferably 0.0015 to 0.0095.

[0033] (Compound (B)) The compound (B) contained in the composition of the present invention is a compound represented by the following formula (1). [ka]

[0034] In formula (1), X represents an oxygen atom, a group represented by the following formula (2), or a group represented by the following formula (3). Y represents an atomic group having 1 to 10 carbon atoms. Z represents one selected from the group consisting of a carboxy group, a sulfo group, a phosphate group, salts thereof, and anions thereof. R 1 represents an acyl group or a hydrocarbon group. [ka] [ka]

[0035] In formula (2) and formula (3), R 2 , R 3 and R 4 each independently represents a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or a bond bonding to Y. * represents a bond.

[0036] As described above, when compound (B) has, as X, a group containing an electron-withdrawing atom such as an oxygen atom or a nitrogen atom, it is possible to improve the uniformity of the aqueous solution and the separability of the PVA.

[0037] X is preferably a group represented by the formula (2) or a group represented by the formula (3), and more preferably a group represented by the formula (2). When X is a group represented by the formula (2), R 2 is preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, more preferably a hydrogen atom, a methyl group or an ethyl group, and even more preferably a methyl group. When X is a group represented by the formula (3), R 3 and R 4 are each independently preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, more preferably a hydrogen atom, a methyl group or an ethyl group, and even more preferably a hydrogen atom or a methyl group. X is preferably a secondary amine, tertiary amine or quaternary amine, and more preferably a secondary amine or tertiary amine.

[0038] Y is an atomic group having 1 to 10 carbon atoms, preferably an atomic group having 1 to 8 carbon atoms, and more preferably an atomic group having 1 to 5 carbon atoms. Y may contain an atom other than carbon. When Y contains an atom other than carbon, there are no particular restrictions on the atom other than carbon, but it is preferable that it is at least one selected from the group consisting of oxygen, nitrogen, and hydrogen. Y may bond with X to form a ring structure. In this case, when X is a group represented by the formula (2), R 2 is a bond bonded to Y, and when X is a group represented by the formula (3), R 3 and R 4 At least one of the groups is a bond bonded to Y. In one embodiment, it is preferred that Y does not bond to X to form a ring structure. In another preferred embodiment, Y is a substituted or unsubstituted hydrocarbon group. The hydrocarbon group represented by Y is more preferably a hydrocarbon group having 1 to 5 carbon atoms, and is preferably -(CH2) n More preferably, it is a group represented by - (n is an integer of 1 to 5), and -(CH2) n It is even more preferable that Y is a group represented by - (n is an integer of 1 to 3), and it is particularly preferable that Y is a methylene group (-CH2-) or an ethylene group (-CH2-CH2-). When Y is a relatively small group, X, which contains an electron-withdrawing atom such as an oxygen atom or a nitrogen atom, is located in the vicinity of Z, which can further improve the uniformity of the aqueous solution and the separability of the PVA. Some or all of the hydrogen atoms of the hydrocarbon group represented by Y may be substituted with a substituent. The substituent is preferably a carboxy group, a salt of a carboxy group, or an anion of a carboxy group.

[0039] Z is preferably a salt of a carboxy group, a salt of a sulfo group, or a salt of a phosphate group. In one embodiment, Z is also preferably a carboxy group, a salt of a carboxy group, or an anion of a carboxy group, and more preferably a salt of a carboxy group. In particular, when compound (B) is present in a solution, particularly an aqueous solution, Z is an anion of a carboxy group (-COO - ), sulfo group anion (-SO3 - ) or the anion of the phosphate group (-HPO4- or -PO4 2- When Z is a sulfo group (SO3H-) or a phosphate group (H2PO4-), compound (B) may be a phosphate ester or a sulfonate ester.

[0040] When Z is a salt of a carboxy group, a salt of a sulfo group, or a salt of a phosphate group, the type of salt is not particularly limited and includes alkali metal salts such as sodium, potassium, and lithium; alkaline earth metal salts such as calcium and magnesium; aluminum salts; zinc salts; ammonium salts; organic amine salts such as monoethanolamine, diethanolamine, triethanolamine (TEA), and triisopropanolamine; and basic salts such as arginine and lysine, with alkali metal salts being preferred, and sodium salts being more preferred. For example, compound (B) can be obtained as a salt thereof by adding an alkali or an aqueous solution thereof to compound (B) which is a carboxylic acid, sulfonic acid, or phosphoric acid. For example, to convert the N-long-chain acyl amino acid described below into an amine salt or alkali metal salt, an alkali or an aqueous solution thereof can be added to the N-long-chain acyl amino acid.

[0041] R 1 is preferably an acyl group. 1 is an acyl group, R 1 is preferably a group represented by the following formula (4): 5 represents a saturated or unsaturated hydrocarbon group having 7 to 20 carbon atoms which may have a substituent. [ka]

[0042] R 5is preferably a saturated or unsaturated hydrocarbon group having 7 to 20 carbon atoms, more preferably a linear saturated or unsaturated hydrocarbon group having 7 to 20 carbon atoms, even more preferably a linear saturated hydrocarbon group having 7 to 20 carbon atoms, and even more preferably a linear saturated hydrocarbon group having 9 to 13 carbon atoms. In one embodiment, the acyl group is preferably derived from coconut oil.

[0043] Also R 1 When R is a hydrocarbon group, the hydrocarbon group is preferably a saturated or unsaturated hydrocarbon group having 7 to 21 carbon atoms, more preferably a linear saturated or unsaturated hydrocarbon group having 7 to 21 carbon atoms, and even more preferably a linear saturated hydrocarbon group having 7 to 21 carbon atoms. 1 is preferably an n-octyl group, an n-decyl group, a lauryl group or an n-tetradecyl group.

[0044] In one embodiment, compound (B) is a compound represented by formula (1), wherein X is a group represented by formula (2), and R 1 In one embodiment, X is a group represented by the formula (2), Y is a hydrocarbon group having 1 to 5 carbon atoms, Z is a salt of a carboxy group, and R 1 is a group represented by formula (4), and R 2 is an alkyl group having 1 to 3 carbon atoms, and R 5 is more preferably a linear saturated hydrocarbon group having 9 to 13 carbon atoms.

[0045] In one embodiment, compound (B) is preferably at least one selected from the group consisting of acylamino acid salts and acyllactates. The acylamino acid salt is preferably an N-acylamino acid salt. The N-acylamino acid salt preferably has an acyl group derived from a saturated or unsaturated fatty acid having 8 to 20 carbon atoms.

[0046] In one embodiment, compound (B) is preferably at least one selected from the group consisting of phosphate ester salts, acylamino acid salts, acyl lactates, acyltaurate salts, soaps (higher fatty acids), alkyl sulfosuccinates, acyl hydrolyzed collagen salts, and acyl isethionates, more preferably at least one selected from the group consisting of acyl lactates and acylamino acid salts, even more preferably an acylamino acid salt, and even more preferably an N-acylamino acid salt.

[0047] Preferred N-acylamino acid salts are salts of N-acylamino acids in which an acyl group derived from a saturated or unsaturated fatty acid having 8 to 20 carbon atoms has been introduced into the amino group of the amino acid (hereinafter, sometimes referred to as "N-long-chain acylamino acid salts"). The amino acid residue of the N-acylamino acid salt may be any of various amino acids such as α-amino acids, β-amino acids, γ-amino acids, or ω-amino acids, and the amino group may be N-methyl or N-ethyl. Furthermore, the optical isomer, i.e., D-, L-, or racemic form, may be used. Examples of the amino acid residue of the N-acylamino acid salt include glutamic acid, aspartic acid, glycine, sarcosine, alanine, leucine, isoleucine, serine, threonine, cysteine, cystine, methionine, lysine, arginine, phenylalanine, tyrosine, histidine, tryptophan, proline, oxyproline, β-aminopropionic acid, γ-aminobutyric acid, anthranilic acid, m-aminobenzoic acid, p-aminobenzoic acid, lanthionine, β-methyllanthionine, cystathionine, dienecholic acid, phenylalanine, and aminomethylpropionic acid. Examples of the amino acid include sarcosine, β-oxyaspartic acid, α-amino-α-methylsuccinic acid, β-oxyglutamic acid, γ-oxyglutamic acid, γ-methylglutamic acid, γ-methyleneglutamic acid, γ-methyl-γ-oxyglutamic acid, α-aminoadipic acid, α,α'-diaminoadipic acid, β,β'-diaminoadipic acid, α-amino-γ-oxyadipic acid, α-aminopimelic acid, α-amino-γ-oxypimelic acid, β-aminopimelic acid, α-aminosuberic acid, and α-aminosebacic acid, and preferably sarcosine.

[0048] As described above, the acyl group in the acyl lactate salt and the acyl amino acid salt is preferably derived from a saturated or unsaturated fatty acid having 8 to 20 carbon atoms, whether linear, branched, or cyclic. Examples of the fatty acid include linear fatty acids such as caprylic acid, pelargonic acid, capric acid, undecanoic acid, lauric acid, tridecanoic acid, myristic acid, pentadecanoic acid, palmitic acid, margaric acid, stearic acid, nonadecanoic acid, and arachic acid; 2-butyl-5-methylpentanoic acid, 2-isobutyl-5-methylpentanoic acid, dimethyloctanoic acid, dimethylnonanoic acid, 2-butyl-5-methylhexanoic acid, methylundecanoic acid, dimethyldecanoic acid, 2-ethyl-3-methylnonanoic acid, 2,2-dimethyl-4-ethyloctanoic acid, methyldocosanoic acid, 2-propyl-3-methylnonanoic acid, methyltridecanoic acid, dimethyldodecanoic acid, and 2-butyl-5-methylhexanoic acid; 3-methylnonanoic acid, methyltetradecanoic acid, ethyltridecanoic acid, propyldodecanoic acid, butylundecanoic acid, pentyldecanoic acid, hexylnonanoic acid, 2-(3-methylbutyl)-3-methylnonanoic acid, 2-(2-methylbutyl)-3-methylnonanoic acid, butylethylnonanoic acid, methylpentadecanoic acid, ethyltetradecanoic acid, propyltridecanoic acid, butyldodecanoic acid, pentylundecanoic acid, hexyldecanoic acid, heptylnonanoic acid, dimethyltetradecanoic acid carboxylic acid, butylpentylheptanoic acid, trimethyltridecanoic acid, methylhexadecanoic acid, ethylpentadecanoic acid, propyltetradecanoic acid, butyltridecanoic acid, pentyldodecanoic acid, hexylundecanoic acid, heptyldecanoic acid, methylheptylnonanoic acid, dipentylheptanoic acid, methylheptadecanoic acid, ethylhexadecanoic acid, ethylhexadecanoic acid, propylpentadecanoic acid, butyltetradecanoic acid, pentyltridecanoic acid, hexyldodecanoic acid, heptylun Branched fatty acids such as decanoic acid, octyldecanoic acid, dimethylhexadecanoic acid, methyloctylnonanoic acid, methyloctadecanoic acid, ethylheptadecanoic acid, dimethylheptadecanoic acid, methyloctyldecanoic acid, methylnonadecanoic acid, methylnonadecanoic acid, dimethyloctadecanoic acid, and butylheptylnonanoic acid, octenoic acid, nonenoic acid, decenoic acid, caproleic acid, undecylenic acid, lindelic acid, cinnamic acid, lauroleic acid, tridecenoic acid, tsuzuic acid, and myristoleic acid,Straight-chain monoenoic acids such as pentadecenoic acid, hexedecenoic acid, palmitoleic acid, heptadecenoic acid, octadecenoic acid, oleic acid, nonadecenoic acid, and gondoic acid; branched monoenoic acids such as methylheptenoic acid, methylnonenoic acid, methylundecenoic acid, dimethyldecenoic acid, methyldodecenoic acid, methyltridecenoic acid, dimethyldodecenoic acid, dimethyltridecenoic acid, methyloctadecenoic acid, dimethylheptadecenoic acid, and ethyloctadecenoic acid; linoleic acid, linoelaidic acid, eleostearic acid, linolenic acid, linoleneelaidic acid, pseudoeleostearic acid, parinaric acid, and arachidonic acid. Examples of acyl groups include acyl groups derived from di- or trienoic acids, acetylenic acids such as octynoic acid, nonynoic acid, decynoic acid, undecynoic acid, dodecynoic acid, tridecynoic acid, tetradecynoic acid, pentadecynoic acid, heptadecynoic acid, octadecynoic acid, nonadecynoic acid, and dimethyloctadecynoic acid, and cyclic acids such as methyleneoctadecenoic acid, methyleneoctadecanoic acid, aleprolic acid, areprestic acid, aleprilic acid, alepuric acid, hydnocarpic acid, schormuglic acid, golric acid, α-cyclopentylic acid, α-cyclohexylic acid, and α-cyclopentylethyl acid, with lauric acid being preferred. Acyl groups derived from fatty acids obtained from natural fats and oils are also acceptable, and are preferably acyl groups derived from mixed fatty acids containing 80% or more of the aforementioned saturated or unsaturated fatty acids having 8 to 20 carbon atoms. Examples of the acyl groups include those derived from coconut oil fatty acid, palm oil fatty acid, linseed oil fatty acid, sunflower oil fatty acid, soybean oil fatty acid, sesame oil fatty acid, castor oil fatty acid, olive oil fatty acid, and camellia oil fatty acid.

[0049] When compound (B) is an acyl amino acid salt, preferred acyl amino acid salts include sodium cocoyl glutamate, TEA cocoyl glutamate, potassium cocoyl glutamate, sodium lauroyl glutamate, TEA lauroyl glutamate, potassium lauroyl glutamate, sodium cocoyl sarcosine, TEA cocoyl sarcosine, potassium cocoyl sarcosine, sodium lauroyl sarcosine, TEA lauroyl sarcosine, potassium lauroyl sarcosine, sodium cocoyl aspartate, TEA cocoyl aspartate, potassium cocoyl aspartate, sodium lauroyl aspartate, TEA lauroyl aspartate, potassium lauroyl aspartate, sodium cocoyl methyl alanine, and TE cocoyl methyl alanine. Examples include cocoyl methyl alanine A, potassium cocoyl methyl alanine, sodium lauroyl methyl alanine, TEA lauroyl methyl alanine, potassium lauroyl methyl alanine, sodium cocoyl glycine, TEA cocoyl glycine, potassium cocoyl glycine, sodium lauroyl glycine, TEA lauroyl glycine, potassium lauroyl glycine, sodium myristoyl sarcosine, TEA myristoyl sarcosine, potassium myristoyl sarcosine, sodium lauroyl methyl-β-alanine, TEA lauroyl methyl-β-alanine, potassium cocoyl methyl-β-alanine, sodium cocoyl methyl-β-alanine, TEA cocoyl methyl-β-alanine, and potassium cocoyl methyl-β-alanine, with sodium lauroyl sarcosine being more preferred.

[0050] When compound (B) is an acyl lactate, preferred acyl lactate include sodium cocoyl lactiate, TEA cocoyl lactiate, potassium cocoyl lactiate, sodium lauroyl lactiate, TEA lauroyl lactiate, potassium lauroyl lactiate, sodium stearoyl lactiate, TEA stearoyl lactiate, potassium stearoyl lactiate, sodium isostearoyl lactiate, TEA isostearoyl lactiate, potassium isostearoyl lactiate, and the like.

[0051] In one embodiment, compound (B) is preferably at least one selected from the group consisting of acids, their salts, and their anions, each having an acid dissociation constant (pKa) in water of 0 to 6.0. The lower limit of pKa is preferably 0, more preferably 1.0, and even more preferably 1.5. The upper limit of pKa is preferably 6.0, more preferably 5.5, and even more preferably 5.0. When compound (B) is an acid or a salt thereof within the above pKa range, in a composition in the form of an aqueous solution containing PVA (A) and compound (B), the solubility of PVA (A) is superior, and separation of PVA (A) from the aqueous solution under weakly acidic conditions is superior.

[0052] The composition of the present invention may contain two or more of the above-mentioned compounds (B).

[0053] The composition of the present invention may consist solely of PVA (A) and compound (B), or may further contain other components in addition to PVA (A) and compound (B). Examples of other components include polymers other than PVA (A), surfactants other than compound (B), and solvents such as water. The optional components that may be included in compositions for specific applications, as described below, also fall under the category of other components. The composition may be in the form of a liquid, a slurry, or a solid such as a powder or film. The lower limit of the total content of PVA (A) and compound (B) in the composition may be 1% by mass, 5%, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, 95%, 97%, or 99% by mass. The upper limit of the total content of PVA (A) and compound (B) in the composition may be 100% by mass, or may be 99%, 95%, 90%, 80%, 70%, 60%, 50%, 40%, 30%, 20%, 10%, or 5% by mass.

[0054] The composition of the present invention may be an aqueous solution containing water as another component, as described below. The lower limit of the total content of PVA (A), compound (B), and water in the composition is preferably 70% by mass, more preferably 80% by mass, and even more preferably 90% by mass, and may be 95%, 97%, 99%, or 99.9% by mass. The upper limit of the total content of PVA (A), compound (B), and water in the composition may be 100% by mass, 99.9%, or 99% by mass. When the composition is an aqueous solution, the content of PVA (A) may be, for example, 1% to 40% by mass, 5% to 35% by mass, or 10% to 30% by mass.

[0055] The composition of the present invention may consist essentially of PVA (A) and compound (B). Aqueous solutions containing such compositions and water, and mixtures of such compositions with other components, are also suitable embodiments of the present invention. The mixtures also include aqueous solutions.

[0056] (Application) One embodiment of the composition of the present invention is at least one composition selected from the group consisting of an agricultural composition, an automotive composition, an aviation composition, an industrial composition, a livestock composition, a marine composition, a pharmaceutical composition, a personal care composition, a recreational composition, and a water treatment composition.

[0057] Agricultural products refer to products and materials used in agriculture and horticulture. Typical examples of agricultural product compositions include pesticide compositions, such as insecticides, fungicides, insecticides and fungicides, herbicides, rodenticides, plant growth regulators, attractants, spreaders, repellents, defoliants, fertilizers, trace element and trace nutrient agents, etc.

[0058] When the composition is an agricultural chemical composition, the composition may contain, in addition to PVA (A) and compound (B), a medium such as water and an active ingredient for imparting a desired action or function, such as an insecticide or herbicide.

[0059] Automotive products refer to products and materials used in the automotive industry. Examples of automotive product compositions include car wash detergents and windshield washer fluids.

[0060] Aviation supplies refer to supplies and materials used in the aviation industry. Examples of aviation supply compositions include aircraft detergents.

[0061] Industrial products refer to products and materials used in manufacturing. Examples of industrial product compositions include machine cleaners and dispersants for the polymerization of vinyl compounds. As the dispersant for the polymerization of vinyl compounds, a dispersant for the suspension polymerization of vinyl chloride is preferred.

[0062] Livestock products refer to products and materials used in dairy farming and livestock breeding. Examples of livestock product compositions include cleaners for livestock barns and cleaners for agricultural machinery.

[0063] Marine products refer to supplies and materials used in fishing, marine products, shipbuilding, marine exploration, etc. Examples of marine product compositions include ship detergents, ship equipment detergents, and seafood processing equipment detergents.

[0064] Pharmaceutical compositions include pharmaceuticals, quasi-drugs, and the like.

[0065] Personal care products refer to products that can be applied to the body of a human or non-human animal, including skin, teeth, nails, and hair. Examples of personal care products include cosmetics, shampoos, body washes, facial cleansers, toothpastes, etc.

[0066] When the composition is a personal care product, the composition may contain, in addition to the PVA (A) and the compound (B), for example, water, a thickener, a fragrance, a colorant, a dispersant, a scrubbing agent, an emulsifier, a moisturizer, a bleaching agent, etc.

[0067] The recreational product refers to products and materials used in recreation. Examples of recreational product compositions include foam sprays, bath additives, and pool foaming agents.

[0068] A water treatment agent refers to an agent that is added to water or a liquid containing water as its main component (containing 50% by mass or more of water relative to the total mass) for the purpose of preventing the growth of microorganisms, corrosion, scale, etc. Examples of water treatment agent compositions include water treatment agents for drinking water, industrial water treatment agents, sewage treatment agents, industrial wastewater treatment agents, and pool water purifying agents.

[0069] When the composition is a water treatment agent composition, the composition can contain, in addition to the PVA (A) and the compound (B), a medium such as water, and a polymer flocculant or an inorganic flocculant composed of a water-soluble (co)polymer having a water-soluble monomer as a constituent unit.

[0070] <Aqueous solution> The composition of the present invention may be an aqueous solution further containing water. In such an aqueous solution, PVA (A), which has low solubility in water and is difficult to dissolve in water by itself, is solubilized in water by the action of compound (B). Conventionally, separating and extracting dissolved PVA from a PVA aqueous solution once prepared has been difficult, as it requires the use of a large amount of salt or poor solvent. In the present invention, since the solubilizing ability of compound (B) decreases under weakly acidic conditions, it is possible to separate at least a portion of the PVA (A) contained in the aqueous solution from the aqueous solution by placing the aqueous solution (composition) under weakly acidic conditions.

[0071] The aqueous solution (composition) preferably separates into two phases, a clear supernatant and a resin precipitate, when the pH of the aqueous solution is adjusted to 3.0 at room temperature. Such an aqueous solution makes it easier to filter the PVA (A) contained in the aqueous solution. The resin precipitate obtained by filtration is preferably dried at 105°C for 24 hours, and the mass of the resin precipitate is preferably 70% by mass or more of the PVA (A) originally contained in the aqueous solution.

[0072] The aqueous solution as the composition of the present invention is preferably a transparent, homogeneous liquid at room temperature before the operation of separating the PVA (A) contained in the aqueous solution, i.e., in a state in which the PVA (A) and the compound (B) are dissolved in water. The pH of the aqueous solution as the composition of the present invention is preferably 4.0 to 11.0, and may be 5.0 to 10.0, 5.5 to 9.0, or 6.0 to 8.0.

[0073] <Method for separating vinyl alcohol polymer> The method for separating a vinyl alcohol polymer of the present invention is a method for precipitating at least a portion of the PVA (A) contained in the aqueous solution (composition) by adjusting the pH of the composition, which is an aqueous solution. In one embodiment, it is preferable to adjust the pH of the aqueous solution to 3.0 or less to precipitate a resin precipitate containing the PVA (A). Furthermore, it is preferable that the mass of the resin precipitate collected by filtration and dried at 105°C for 24 hours is 70% by mass or more of the PVA (A) originally contained in the aqueous solution. [Example]

[0074] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples in any way.

[0075] For the compositions used in the following Examples and Comparative Examples, the RT, viscosity average degree of polymerization, and degree of saponification of the PVA (A) in the composition were measured and calculated according to the methods described below.

[0076] [PVA holding time RT] The retention time RT of PVA is the peak top retention time measured by reversed-phase gradient high-performance liquid chromatography using a mixture of ion-exchanged water and ethanol as the eluent. The measurement was carried out under the following conditions. The "peak top" is the point where the detectable level in the chromatogram obtained by the chromatography measurement is the maximum and is also the local maximum. <Measurement conditions> Column: Shimpack G-ODS (4) (Shimadzu Corporation, octadecyl-modified spherical fully porous silica gel, inner diameter 4 mm × length 10 mm, particle size 5 μm) Column temperature: 45℃ Eluent: A mixture of ion-exchanged water (X) and ethanol (purity 99.5%) (Y) Eluent composition at each measurement time; 0 to 5 minutes: (Y) Concentration 5% by volume 5 to 25 minutes: (Y) concentration 5 to 100% by volume 25-40 min: (Y) concentration 100% by volume constant 40-41 min: (Y) concentration 100-5% by volume 41 to 55 minutes: (Y) concentration constant at 5% by volume (The (Y) concentration was gradually increased from 5% by volume to 100% by volume at a substantially constant rate between 5 and 25 minutes. The (Y) concentration was gradually decreased from 100% by volume to 5% by volume at a substantially constant rate between 40 and 41 minutes.) Mobile phase flow rate: 0.4mL / min Sample concentration: 5 mg / mL Detector: ELSD-LTII (Shimadzu Corporation, drift tube temperature 40°C, gain 6 (=32 times), N2 gas spray pressure primary 0.4 MPa, secondary 0.35 MPa, data acquisition interval: 1000 ms, filter: 1 sec.) Injection volume: 5μL Length from injection to column inlet: 900 mm Length from column outlet to nebulizer of ELSD-LTII detector: 1375 mm Pipe diameter: 0.3mm ID

[0077] [Viscosity average degree of polymerization of PVA] The viscosity-average degree of polymerization of PVA was measured in accordance with JIS K6726: 1994. Specifically, when the degree of saponification of PVA was less than 99.5 mol%, it was saponified until the degree of saponification reached 99.5 mol% or more, and the viscosity-average degree of polymerization of the resulting PVA was calculated by the following formula using the intrinsic viscosity [η] (liter / g) measured in water at 30°C. Viscosity average degree of polymerization=([η]×10 4 / 8.29) (1 / 0.62)

[0078] [Saponification degree of PVA] The degree of saponification (mol %) of PVA was measured in accordance with JIS K 6726:1994.

[0079] [Manufacturing Example 1] A 3-L reactor equipped with a stirrer, nitrogen inlet, additive inlet, and initiator inlet was charged with 480 g of vinyl acetate and 1,120 g of methanol. The temperature was raised to 60°C, and the system was purged with nitrogen by nitrogen bubbling for 30 minutes. The temperature inside the reactor was adjusted to 60°C, and 1.2 g of 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile) was added to initiate polymerization. The polymerization temperature was maintained at 60°C during polymerization, and after 5 hours, when the conversion reached 70%, the system was cooled and terminated. Unreacted vinyl acetate was then removed under reduced pressure to obtain a methanol solution of polyvinyl acetate. A 10% NaOH methanol solution was added to the 30% polyvinyl acetate methanol solution to obtain PVA (A) and saponification at an alkali molar ratio (moles of NaOH / moles of vinyl ester units in polyvinyl acetate) of 0.0025, yielding PVA1. The degree of saponification, viscosity average degree of polymerization, and retention time RT of the obtained PVA1 are shown in Table 1.

[0080] [Manufacturing Example 2] A 3-L reactor equipped with a stirrer, nitrogen inlet, additive inlet, and initiator inlet was charged with 1284 g of vinyl acetate, 316 g of methanol, and 0.107 g of 3-mercaptopropionic acid. The temperature was raised to 60°C, and the system was purged with nitrogen by bubbling with nitrogen for 30 minutes. The temperature inside the reactor was adjusted to 60°C, and polymerization was initiated by adding 4.58 g of methanol containing 0.51 g of 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile). Immediately, 23.30 g of methanol containing 2.33 g of 3-mercaptopropionic acid was added uniformly over 4 hours. The polymerization temperature was maintained at 60°C throughout the polymerization, and after 4 hours, the polymerization was terminated by cooling when the conversion reached 65%. Unreacted vinyl acetate was then removed under reduced pressure to obtain a methanol solution of polyvinyl acetate. A 50% solution of polyvinyl acetate in methanol was saponified by adding a 10% NaOH solution in methanol to an alkali molar ratio (moles of NaOH / moles of vinyl ester units in polyvinyl acetate) of 0.009, to obtain PVA (A) PVA2. The degree of saponification, viscosity-average degree of polymerization, and retention time RT of the resulting PVA2 are shown in Table 1.

[0081] [Manufacturing Example 3] A 3-L reactor equipped with a stirrer, nitrogen inlet, additive inlet, and initiator inlet was charged with 720 g of vinyl acetate and 880 g of methanol. The temperature was raised to 60°C, and the system was purged with nitrogen by nitrogen bubbling for 30 minutes. The temperature inside the reactor was adjusted to 60°C, and 1.2 g of 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile) was added to initiate polymerization. The polymerization temperature was maintained at 60°C throughout the polymerization, and after 5 hours, when the conversion reached 70%, the polymerization was terminated by cooling. Unreacted vinyl acetate was then removed under reduced pressure to obtain a methanol solution of polyvinyl acetate. A 30% methanol solution of polyvinyl acetate was saponified by adding a 10% by weight NaOH methanol solution to an alkali molar ratio (moles of NaOH / moles of vinyl ester units in polyvinyl acetate) of 0.0037, yielding PVA3. The degree of saponification, viscosity-average degree of polymerization, and retention time (RT) of the resulting PVA3 are shown in Table 1.

[0082] [Table 1]

[0083] [Compound (B)] Table 2 shows the surfactants used as compound (B) in the examples and comparative examples.

[0084] [Table 2]

[0085] [Example 1] To 79 parts by mass of ion-exchanged water, 20 parts by mass of PVA1 and 1 part by mass of surfactant 1, "SOYPON SLP" (manufactured by Kawaken Fine Chemicals Co., Ltd., "SOYPON" is a registered trademark), were added, and the mixture was heated and stirred to obtain an aqueous solution, which was the composition.

[0086] [Example 2] To 76 parts by mass of ion-exchanged water, 20 parts by mass of PVA1 and 4 parts by mass of surfactant 2, "Aminosurfact ACDS-L" (manufactured by Asahi Kasei Finechem Corporation, active ingredient 25%, "Aminosurfact" is a registered trademark), were added, and the mixture was heated and stirred to obtain an aqueous solution, which was the composition.

[0087] [Example 3] To 67.6 parts by mass of ion-exchanged water, 30 parts by mass of PVA1 and 2.4 parts by mass of surfactant 3, "Alanon ALE" (manufactured by Kawaken Fine Chemicals Co., Ltd., active ingredient 30%, "Alanon" is a registered trademark), were added, and the mixture was heated and stirred to obtain an aqueous solution, which was the composition.

[0088] [Example 4] To 79 parts by mass of ion-exchanged water, 20 parts by mass of PVA2 and 1 part by mass of surfactant 1, "Soypon SLP" (manufactured by Kawaken Fine Chemicals Co., Ltd.), were added, and the mixture was heated and stirred to obtain an aqueous solution of the composition.

[0089] [Comparative Example 1] An aqueous solution, which is a composition, was obtained in the same manner as in Example 1, except that the PVA used was changed to PVA3.

[0090] Comparative Example 2 An aqueous solution, which is a composition, was obtained in the same manner as in Example 1, except that the surfactant used was changed to surfactant 4, "EMAL 10G" (manufactured by Kao Corporation, "EMAL" is a registered trademark).

[0091] Comparative Example 3 20 parts by mass of PVA1 was added to 80 parts by mass of ion-exchanged water, and the mixture was heated and stirred to obtain an aqueous solution that was a composition.

[0092] Comparative Example 4 To 78.4 parts by mass of ion-exchanged water, 20 parts by mass of PVA1 and 1.6 parts by mass of surfactant 5, "Cortamin 86P Concentrate" (manufactured by Kao Corporation, active ingredient 63%, "Cortamin" is a registered trademark), were added, and the mixture was heated and stirred to obtain an aqueous solution, which was the composition.

[0093] Comparative Example 5 An aqueous solution, which is a composition, was obtained in the same manner as in Example 1, except that the surfactant used was changed to surfactant 6, "Emulgen 150" (manufactured by Kao Corporation, "Emulgen" is a registered trademark).

[0094] [Evaluation of the liquid state of aqueous solutions] The state of each aqueous solution obtained was visually observed at room temperature. If the composition was a transparent, uniform liquid, it was judged as "uniform," and if the composition separated into two or more phases or was suspended, it was judged as "separated."

[0095] [Evaluation of separation by adding acid] Among the prepared aqueous solutions, compositions that were judged to be "homogeneous" in the "Evaluation of the aqueous solution state" were evaluated for separability upon addition of acid. The pH of the aqueous solution was adjusted to 3.0 by adding 0.25 mol / L sulfuric acid, and the state of the aqueous solution was visually observed at room temperature. A case in which the aqueous solution immediately separated into two phases, a clear supernatant and a resin precipitate, and the resin precipitate could be filtered was rated "A." A case in which the composition did not separate into a clear supernatant and a resin precipitate, and the resin precipitate could not be filtered was rated "B." "A case in which the resin precipitate could be filtered" refers to a case in which the mass of the resin precipitate obtained by filtration, after drying at 105°C for 24 hours, was 70% by mass or more of the PVA originally contained in the composition. The pH of the aqueous solution was measured using a pH meter (Horiba, Ltd. F-51).

[0096] For Example 1 and Comparative Examples 1 to 5, the results of evaluating the state of the aqueous solutions and the feasibility of separation by adding acid are summarized in Table 3. The aqueous solution of Example 1 was a transparent, uniform solution, and PVA could be separated under weakly acidic conditions.

[0097] [Table 3]

Claims

1. The polymer (A) has a peak top retention time (RT) of 22 minutes or longer as measured by reversed-phase gradient high-performance liquid chromatography using a water-ethanol eluent, and the compound (B) is included, the content of vinyl ester-derived monomer units relative to all monomer units in the vinyl alcohol polymer (A) is 90 mol% or more, The composition, wherein the compound (B) is a compound represented by formula (1): 【Chemical 1】 [In formula (1), X represents an oxygen atom, a group represented by the following formula (2), or a group represented by the following formula (3). Y represents a hydrocarbon group having 1 to 5 carbon atoms in which some or all of the hydrogen atoms may be substituted with a carboxy group, a salt of a carboxy group, or an anion of a carboxy group. Z represents one selected from the group consisting of a carboxy group, a sulfo group, a salt thereof, and an anion thereof. R １ represents an acyl group represented by the following formula (4) or derived from coconut oil. 【Chemistry 2】 【Chemistry 3】 [In formula (2) and formula (3), R ２ , R ３ and R ４ each independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. * represents a bond. 【Chemistry 4】 [In formula (4), R ５ represents a saturated or unsaturated hydrocarbon group having 7 to 20 carbon atoms which may have a substituent. * represents a bond.]

2. The composition according to claim 1, wherein Z in formula (1) of compound (B) is a carboxy group, a salt of a carboxy group, or an anion of a carboxy group.

3. The composition according to claim 1, wherein, for the compound (B), X in formula (1) is a group represented by formula (2).

4. 2. The composition according to claim 1, wherein the compound (B) is at least one selected from the group consisting of N-acylamino acid salts and acyl lactate salts.

5. The composition according to claim 4, wherein the compound (B) is an N-acylamino acid salt.

6. 6. The composition according to claim 5, wherein the N-acylamino acid salt has an acyl group derived from a saturated or unsaturated fatty acid having 8 to 20 carbon atoms.

7. The composition according to claim 1, wherein the degree of saponification of the vinyl alcohol polymer (A) is 20 mol % or more and 70 mol % or less.

8. The composition according to claim 1, wherein the vinyl alcohol polymer (A) consists solely of monomer units derived from vinyl acetate.

9. 10. The composition of claim 1, which is at least one selected from the group consisting of an agricultural product composition, an automotive product composition, an aviation product composition, an industrial product composition, a livestock product composition, a marine product composition, a pharmaceutical composition, a personal care product composition, a recreational product composition, and a water treatment composition.

10. The composition according to any one of claims 1 to 9, which is an aqueous solution further comprising water.

11. A method for separating a vinyl alcohol polymer, comprising adjusting the pH of the composition according to claim 10 to precipitate at least a part of the vinyl alcohol polymer (A) contained in the composition.

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