COMPOSITION COMPRISING VINYL ALCOHOL-BASED POLYMER AND METHOD FOR SEPARATING VINYL ALCOHOL-BASED 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

1 / 39 COMPOSITION COMPRISING VINYL ALCOHOL-BASED POLYMER AND METHOD FOR SEPARATING VINYL ALCOHOL-BASED POLYMER [TECHNICAL FIELD]

[001] The present invention relates to a composition containing a vinyl alcohol polymer and to a method for separating a vinyl alcohol polymer. [BACKGROUND OF THE TECHNIQUE]

[002] Polyvinyl alcohol polymers (hereinafter referred to as PVAs) are widely used as materials and similar substances for thickening agents, paper coating agents, adhesives, fiber coating agents, binders, emulsion stabilizers, films, fibers, and the like. In use for such intended uses, PVA can be used in an aqueous solution state containing the PVA dissolved in water. This aqueous PVA solution is generally prepared by mixing the PVA with water followed by heating. However, in the case of highly hydrophobic PVAs, dissolution in water generally fails by this process, and the addition of an anionic surfactant is known to allow the preparation of the aqueous solution (Patent Document 1). The formation of a complex of the highly hydrophobic PVA and the anionic surfactant in water results in a successful preparation (Non-Patent Document 1). [Patent Documents]

[003] Patent Document 1: Unexamined Japanese Patent Application, Publication No. S53-133252 [Non-Patent Documents]

[004] Non-patent document 1: Polymer and Surfactant Complexes, Journal of Oleo Science, 1963, vol. 12, No. 3, pp. 133-141, attributed to Shuji S AITO Petition 870250091036, dated 06 / 10 / 2025, p. 7 / 52 2 / 39 [SUMMARY OF THE INVENTION] [Problems being solved by the invention]

[005] However, no composition containing PVA is known that allows the PVA to be easily separated and extracted from an aqueous solution thereof, once produced. An object of the present invention is to provide a composition containing PVA, wherein, in the case of preparation of an aqueous solution thereof, the aqueous solution is homogeneous and the PVA contained in the aqueous solution is easily separable. Furthermore, another object of the present invention is to provide a method for separating PVA. It should be noted that the expression "the aqueous solution is homogeneous" may mean a state in which the PVA is homogeneously dissolved. [Means to Solve the Problems]

[006] Exhaustive research was conducted to resolve the above problems and, consequently, it was discovered that a composition containing a certain PVA and a compound with a certain structure solves the problems, thus concluding the present invention.

[007] Thus, the present invention relates to: (1) A composition containing: a vinyl alcohol polymer (A) having a peak retention time RT of 22 min or more, as measured by reversed-phase gradient partition high-performance liquid chromatography with a water-ethanol eluent; and a compound (B), wherein compound (B) is a compound represented by formula (1): (1) wherein, in formula (1), X represents an oxygen atom, a group represented by formula (2) or a group represented by formula (3); Y represents an atomic group with 1 to 10 carbon atoms; Z represents a selection from the group consisting of a Petition 870250091036, dated 06 / 10 / 2025, page 8 / 52 3 / 39 a carboxyl group, a sulfo group, a phosphoric acid group, a salt thereof, and an anion thereof; and R1 represents an acyl group or a hydrocarbon group, R2 A (2) R3R4<3) MT in formula (2) and in formula (3), R2' R3 and R4 each independently represent a hydrogen atom, an alkyl group with 1 to 3 carbon atoms or an atomic bond that attaches to Y; and * denotes an atomic connection;

[008] (2) The composition according to (1), wherein, with respect to compound (B), Z in formula (1) represents a carboxylic group, a salt of a carboxylic group or an anion of a carboxylic group;

[009] (3) The composition according to (1) or (2), where, with respect to compound (B), X in formula (1) represents a group represented by formula (2), and R1 represents an acyl group;

[0010] (4) The composition according to any one of (1) to (3), wherein compound (B) is at least one selected from the group consisting of an N-acyl amino acid salt and an acyl lactic acid salt;

[0011] (5) The composition according to (4), wherein compound (B) is the N-acyl amino acid salt;

[0012] (6) The composition according to (5), wherein the N-acyl amino acid salt has an acyl group derived from a saturated or unsaturated fatty acid with 8 to 20 carbon atoms;

[0013] (7) The composition according to any one of (1) to (6), where in compound (B), R1 represents a group represented by formula (4): Petition 870250091036, dated 06 / 10 / 2025, p. 9 / 52 4 / 39 O wherein, in formula (4), R5 represents a saturated or unsaturated hydrocarbon group with 7 to 20 carbon atoms that may have a substituent; and * denotes an atomic connection;

[0014] (8) The composition according to any one of (1) to (7), wherein the vinyl alcohol polymer (A) has a degree of saponification of 20 mol% or more and 70 mol% or less;

[0015] (9) The composition according to any one of (1) to (8), wherein the vinyl alcohol polymer (A) consists only of a vinyl acetate-derived monomeric unit;

[0016] (10) A composition according to any one of (1) to (9), which is at least one selected from the group consisting of a composition for agricultural supplies, a composition for automotive supplies, a composition for aeronautical supplies, a composition for industrial supplies, a composition for livestock supplies, a composition for marine supplies, a pharmaceutical composition, a composition for personal care products, a composition for recreational products and a composition for water treatment agents;

[0017] (11) The composition according to any of items (1) to (10), which is an aqueous solution containing water; and

[0018] (12) A method for separating a vinyl alcohol polymer, the method including: adjusting the pH of the composition in accordance with (11) to precipitate at least a portion of the vinyl alcohol polymer (A) contained in the composition. [Effects of the Invention]

[0019] In the case where an aqueous solution is prepared from the composition of the present invention, the aqueous solution is homogeneous and the PVA contained in the aqueous solution is easily separable. Petition 870250091036, dated 06 / 10 / 2025, p. 10 / 52 5 / 39 [DESCRIPTION OF MODALITIES]

[0020] Next, the preferred embodiments for carrying out the present invention will be presented in detail. It should be noted that the scope of the present invention is not limited to the embodiments described herein, and these may be altered in various ways within the scope without compromising the principles of the present invention. Composition

[0021] The composition of the present invention is a composition containing: a vinyl alcohol polymer (A) exhibiting a peak retention time RT of 22 min or more, as measured by reversed-phase gradient partition high-performance liquid chromatography with a water-ethanol eluent (hereinafter referred to as PVA (A)); and a compound (B), wherein compound (B) is a compound represented by formula (1).

[0022] 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 with 1 to 10 carbon atoms; Z represents a selection from the group consisting of a carboxyl group, a sulfo group, a phosphoric acid group, a salt thereof and an anion thereof; and R1 represents an acyl group or a hydrocarbon group. R2 A (2) R3 R4(3)

[0023] In formula (2) and formula (3), R2' R3 and R4 each independently represent a hydrogen atom, an al group Petition 870250091036, dated 06 / 10 / 2025, p. 11 / 52 6 / 39 carat with 1 to 3 carbon atoms or an atomic bond that attaches to Y; and * denotes an atomic connection. In a case where R2-R3 or R4 represent an atomic bond that attaches to Y, X and Y form a ring structure.

[0024] A ratio of PVA (A) to compound (B), each contained in the composition, i.e., (A):(B) in terms of mass ratio, is preferably 99.9:0.1 to 80:20, may be 99:1 to 85:15, or may be 97:3 to 90:10. Alternatively, (A):(B) may preferably be 50:50 to 0.1:99.9. When (A):(B) is within the above range, for example, in the production of a high-concentration aqueous solution of PVA (A), such as 30% by mass, a more homogeneous solution can be obtained.

[0025] A suitable method for producing the composition is not particularly limited and, provided that PVA (A) and compound (B) can be mixed, production of the composition is possible using an arbitrary method. For example, PVA (A) and compound (B) can be mixed directly; compound (B) can be added to a solution containing PVA (A); PVA (A) can be added to a solution containing compound (B); or a solution containing PVA (A) and a solution containing compound (B) can be mixed, thus producing the composition. For example, by adding compound (B) to an aqueous solution of PVA (A), the composition of the present invention can be obtained. Vinyl alcohol polymer (A)

[0026] The PVA (A) contained in the composition of the present invention is a polymer that has a vinyl alcohol unit as its structural unit. The lower limit of the proportion of the vinyl alcohol unit relative to the total structural units in PVA (A) is, for example, preferably 10 mol%, more preferably 20 mol%, even more preferably 30 mol%, and may be even higher. Petition 870250091036, dated 06 / 10 / 2025, page 12 / 52 7 / 39 preferably 40%. On the other hand, the upper limit of the proportion of the vinyl alcohol unit is, for example, preferably 90 mol%, more preferably 80 mol%, and may be even more preferably 60%. PVA (A) can be obtained, for example, by polymerizing a vinyl ester monomer, followed by saponification of a vinyl ester polymer thus obtained, and PVA (A) may include, for example, a vinyl ester unit in addition to the vinyl alcohol unit.

[0027] PVA(A) has a peak retention time (RT) of 22 min or more, measured by high-performance liquid chromatography with reversed-phase partition gradient and water-ethanol eluent. It should be noted that the peak as referred to herein is, in a chromatogram obtained by chromatographic determination, a point at which the detection strength is maximal and exhibits a maximum value; and the peak means a peak top derived from PVA(A). Such PVA is poorly soluble in water and is superior in separability from an aqueous solution. PVA(A) exhibiting a retention time RT of more than 22 min is preferred. In addition, PVA(A) exhibiting a retention time RT of 25 min or less is preferred, and PVA(A) of 22 min < RT < 25 min is most preferred. The retention time RT of PVA (A) can be adjusted by introducing a modifying group or by regulating a degree of saponification and / or a degree of medium viscosity polymerization.

[0028] The retention time RT of PVA (A) is measured under the following measurement conditions. Measurement Conditions

[0029] column: Shimpack G-ODS (4) (manufactured by Shimadzu Corporation, fully porous spherical silica gel modified with octadecyl group; inner diameter 4 mm x length 10 mm; particle diameter: 5 μm)

[0030] column temperature: 45°C Petition 870250091036, dated 06 / 10 / 2025, page 13 / 52 8 / 39

[0031] eluent: a liquid mixture of ion-exchanged water (X) and ethanol (purity: 99.5%) (Y)

[0032] composition of the eluent for each measurement time; 0 to 5 min: concentration of (Y) being 5% by volume, constant

[0033] 5 to 25 min: concentration of (Y) being 5 to 100% by volume

[0034] 25 to 40 min: concentration of (Y) being 100% by volume, constant

[0035] 40 to 41 min: concentration of (Y) being 100 to 5% by volume

[0036] 41 to 55 min: concentration of (Y) being 5% by volume, constant

[0037] (The concentration of (Y) from 5 min to 25 min is gradually increased from 5% by volume to 100% by volume at a substantially constant rate. The concentration of (Y) from 40 to 41 min is gradually decreased from 100% by volume to 5% by volume at a substantially constant rate.)

[0038] Mobile phase flow rate: 0.4 m L / min

[0039] Sample concentration: 5 mg / mL

[0040] detector: ELSD-LTII (manufactured by Shimadzu Corporation, bypass tube temperature 40°C; gain 6 (= 32 times); N2 gas primary spray pressure 0.4 MPa and secondary spray pressure 0.35 MPa; data acquisition interval 1,000 m sec; filter: 1 sec.)

[0041] Injection quantity: 5 μL

[0042] Injection length to column inlet: 900 mm

[0043] Length from column outlet to nebulizer of ELSD-LTII detector: 1.375 mm

[0044] tube diameter: 0.3 mm ID

[0045] The lower limit of the degree of saponification of PVA (A) is pre Petition 870250091036, dated 06 / 10 / 2025, p. 14 / 52 9 / 39 preferably 20% by mole, more preferably 30% by mole, even more preferably 40% by mole and even more preferably 45% by mole. Furthermore, the upper limit of the degree of saponification of PVA (A) is preferably 90% by mole, more preferably 80% by mole, even more preferably 70% by mole, even more preferably 60% by mole and particularly preferably 55% by mole. When the degree of saponification of PVA (A) falls within the above range, the separability of the aqueous solution may be greater. The degree of saponification of PVA (A) can be determined according to a method disclosed in JIS K 6726: 1994.

[0046] The lower limit of the average degree of polymerization of PVA (A) viscosity is preferably 100, and more preferably 200. Furthermore, the upper limit of the average degree of polymerization of PVA (A) viscosity is preferably 3,500, more preferably 2,000, even more preferably 1,000, even more preferably 500, and particularly preferably 300. When the average degree of polymerization of PVA (A) viscosity is within the above range, the separability of the aqueous solution may be higher. The average degree of polymerization of PVA (A) viscosity can be determined according to JIS K 6726: 1994.

[0047] 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, vinyl oleate, and the like. Among these, vinyl acetate is preferred due to its availability and economic efficiency. Only one type of monomer Petition 870250091036, dated 06 / 10 / 2025, page 15 / 52 10 / 39 ro of vinyl ester can be used, or two or more types thereof can be used in combination.

[0048] PVA(A) may be a polymer consisting only of a monomeric unit derived from a vinyl ester monomer, or it may be a polymer consisting only of a monomeric unit derived from vinyl acetate. However, in this case as well, a terminal structure of PVA(A) may be a structure derived from, for example, a polymerization initiator, a chain transfer agent, or similar, which is different from the vinyl ester monomer. PVA(A) may be a polymer consisting substantially only of a monomeric unit derived from a vinyl ester monomer, or it may be a polymer consisting substantially only of a monomeric unit derived from vinyl acetate. The monomeric unit derived from a vinyl ester monomer may be a vinyl alcohol unit and a vinyl ester unit.The lower limit of a proportion of the monomeric unit derived from a vinyl ester monomer relative to the total structural units in PVA(A) is, for example, preferably 90 mol%, and may be 95 mol%, 98 mol%, 99 mol%, 99.5 mol%, or 99.9 mol%. Conversely, the upper limit of the proportion of the monomeric unit derived from a vinyl ester monomer may be 100 mol%. It should be noted that even when the proportion of the monomeric unit derived from a vinyl ester monomer relative to the total structural units in PVA(A) is 100 mol%, as described above, the terminal structure of PVA(A) may be a structure derived from a structure other than the vinyl ester monomer.

[0049] PVA (A) can be a modified PVA obtained by introducing: a unit other than a unit derived from the vinyl ester monomer; or a functional group, using a process Petition 870250091036, dated 06 / 10 / 2025, page 16 / 52 11 / 39 ment as copolymerization, acetalization, esterification or similar.

[0022]

[0050] In the case where PVA (A) is copolymerized and PVA modified, the copolymerized and modified PVA can be obtained by, for example, saponification of a vinyl ester copolymer obtained by copolymerizing a vinyl ester monomer with a monomer other than the vinyl ester monomer. As the monomer other than the vinyl ester monomer to be copolymerized with the vinyl ester monomer, any monomer that is copolymerizable with the vinyl ester monomer can be used. Examples of such other monomers include: α-olefins, such as propylene, 1-butene, isobutene, pentene, 1-hexene, 1-octene, 1-dodecene, 1-hexadecene and 1-octadecene; methacrylic acid; esters of (meth)acrylic acid, 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; methacrylamide derivatives, such as N-methylmethacrylamide and N-ethylmethacrylamide; 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 stearate ether; allyl acetate; allylic ethers, such as allyl propyl ether, allyl butyl ether and allyl hexyl ether; monomers, each with an oxyalkylene group; isopropenyl acetate; Monomers, each with a silyl group, such as vinylmethyldimethoxysilane, vinyldimethylmethoxysilane, vinyltriethoxysilane, vinylmethyldiethoxysilane, vinyldimethylethoxysilane, 3(meth)acrylamidepropyltrimethoxysilane and 3(meth)acrylamidepropyltriethoxysilane; and the like. One type may be used alone, or two or more types thereof may be used in combination. Petition 870250091036, dated 06 / 10 / 2025, page 17 / 52 12 / 39

[0051] In the case where PVA (A) is modified PVA obtained by introducing the modifying group by acetalization, a modifying agent used to introduce the modifying group by acetalization is not particularly limited and is exemplified by linear, branched, saturated cyclic, unsaturated cyclic or aromatic aldehyde or aldose having from 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, octadecanal and the like. Furthermore, the modifying agent may, for example, have halogen and / or similar components replaced by one or more hydrogen atoms of the modifying agent. The modifying agent may be used alone, or two or more types of the same may be used in combination.

[0052] In the case where PVA (A) is modified PVA obtained by introducing the modifying group by esterification, a modifying agent used to introduce the modifying group by esterification is not particularly limited and is exemplified by linear, branched, saturated cyclic, unsaturated cyclic or aromatic carboxylic acids, each having from 1 to 19 carbon atoms, and carboxylic acid derivatives, each having from 1 to 19 carbon atoms, such as 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, or an acid chloride thereof, and the like.Furthermore, the modifying agent may, for example, have halogen and / or similar components replaced by one or more hydrogen atoms of the modifying agent. The modifying agent may be used alone, or two or more types of the same agent may be used. Petition 870250091036, dated 06 / 10 / 2025, page 18 / 52 13 / 39 can be used in combination.

[0053] PVA (A) can be produced according to a conventionally known procedure. For example, as a procedure for obtaining vinyl ester polymer from vinyl ester monomer, one can adopt a bulk polymerization procedure, a solution polymerization procedure, a suspension polymerization procedure, an emulsion polymerization procedure, a dispersion polymerization procedure or similar procedures. Among these, the solution polymerization procedure is the industrially preferred one.

[0054] In the preparation of vinyl ester polymer, a polymerization initiator may be used. The polymerization initiator may be selected from well-known initiators, depending on the polymerization method. Specific examples of polymerization initiators include: azo-type 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 dietoxyethyl peroxydicarbonate; perester compounds, such as tert-butyl peroxyneodecanate, α-cumyl peroxyneodecanate and tert-butyl peroxyneodecanate; acetylcyclohexylsulfonyl peroxide; Peroxide-type initiators, such as 2,4,4-trimethylpentyl-2-peroxyphenoxyacetate; and the like.

[0055] The amount of polymerization initiator can be predetermined ad libitum, depending on the type of monomer and / or initiator to be used, as well as the desired degree of polymerization and the like, and the amount of polymerization initiator in relation to the total mass of the vinyl ester monomer is preferably 0.20 to 0.33 % by mass.

[0056] In the preparation of vinyl ester polymer, an agent of Petition 870250091036, dated 06 / 10 / 2025, page 19 / 52 14 / 39 Chain transfer can be used. The chain transfer agent can be selected from among well-known chain transfer agents, depending on the polymerization process. Specific examples of chain transfer agents include: aldehydes, such as acetaldehyde and propionaldehyde; ketones, such as acetone and methyl ethyl ketone; halogenated hydrocarbons, such as trichloroethylene and perchloroethylene; and phosphinic acid salts, such as sodium hypophosphite monohydrate. Among these, aldehydes and ketones are suitably used. The amount of chain transfer agent is not particularly limited, provided it can be predetermined to provide a desired degree of polymerization of the vinyl ester polymer, depending on the chain transfer constant of the chain transfer agent to be added.Furthermore, a functional group can be introduced using a chain transfer agent; a chain transfer agent having an alkyl group can be used to introduce an aliphatic hydrocarbon group at one end, or a chain transfer agent having a carboxyl group can be used to introduce an ionic functional group at one end.

[0057] Polymerization conditions and the like can be predetermined ad libitum, depending on the type and quantity of monomer to be used, the desired physical properties, the polymerization method adopted, and the like. For example, the polymerization temperature is typically 0 to 150°C, and preferably 20 to 120°C.

[0058] A degree of polymerization in the vinyl ester polymer can be, for example, from 20 to 95%. The degree of polymerization is preferably 30% or more, and more preferably 40% or more, taking into account improved yield, control of the degree of polymerization and the like. Petition 870250091036, dated 06 / 10 / 2025, page 20 / 52 15 / 39

[0059] For the saponification reaction of vinyl ester polymer obtained by means of an alcoholysis or hydrolysis reaction in which a basic catalyst is used, such as sodium hydroxide, potassium hydroxide or sodium methoxide, or an acid catalyst, such as ptoluenesulfonic acid, both conventionally known. 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; aromatic hydrocarbons, such as benzene and toluene; and the like. One type of these may be used alone, or two or more types of these may be used in combination. Among these, for the saponification reaction, a procedure is preferred for carrying out a saponification reaction in the presence of sodium hydroxide, which is a basic catalyst, using methanol or a mixed solution of methanol with methyl acetate as solvent.

[0060] The amount of catalyst used in the saponification reaction can be predetermined ad libitum, depending on the type of catalyst to be used, the desired degree of saponification, and the like. For example, in the case where sodium hydroxide is used as a catalyst for the saponification reaction, in one embodiment of the present invention, a ratio (molar ratio) of catalyst to vinyl ester monomer in the vinyl ester copolymer is preferably 0.0015 to 0.0095. Compound (B)

[0061] The compound (B) contained in the composition of the present invention is a compound represented by the following formula (1). IR^ XZ

[0062] 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 with 1 Petition 870250091036, dated 06 / 10 / 2025, page 21 / 52 16 / 39 to 10 carbon atoms; Z represents a selection from the group consisting of a carboxyl group, a sulfo group, a phosphoric acid group, a salt thereof, and an anion thereof; and R1 represents an acyl group or a hydrocarbon group. R2 Â (2) R3R4(3)

[0063] In formula (2) and formula (3), R2' R3 and R4 each independently represent a hydrogen atom, an alkyl group with 1 to 3 carbon atoms or an atomic bond that attaches to Y; and * denotes an atomic bond.

[0064] As described above, by including, for example, an oxygen atom or a group that includes an electron-attracting atom, such as a nitrogen atom, in compound (B) as X, it is possible to improve the homogeneity of the aqueous solution and the separability of the PVA.

[0065] X preferably represents the group represented by formula above (2), or the group represented by formula above (3), and more preferably the group represented by formula above (2). In the case where X represents the group represented by formula above (2), R2 preferably represents a hydrogen atom or an alkyl group with 1 to 3 carbon atoms, more preferably a hydrogen atom, a methyl group or an ethyl group, and even more preferably a methyl group. Furthermore, in the case where X represents the group represented by formula above (3), R3 and R4 each independently represent preferably a hydrogen atom or an alkyl group with 1 to 3 carbon atoms, more preferably a hydrogen atom, a methyl group or an ethyl group, and even more preferably a hydrogen atom. Petition 870250091036, dated 06 / 10 / 2025, page 22 / 52 17 / 39 or a methyl group. Alternatively, X preferably represents a secondary amine, a tertiary amine, or a quaternary amine, and most preferably a secondary amine or a tertiary amine.

[0066] Y represents an atomic group with 1 to 10 carbon atoms, preferably an atomic group with 1 to 8 carbon atoms, and most preferably an atomic group with 1 to 5 carbon atoms. In addition, Y may include an atom other than carbon. In the case where Y includes an atom other than carbon, the atom other than carbon is not particularly limited and is preferably at least one selected from the group consisting of oxygen, nitrogen, and hydrogen. Alternatively, Y and X may bond to form a ring structure. Here, in a case where X represents a group represented by formula (2) above, R2 represents an atomic bond that bonds to Y, while in a case where X represents a group represented by formula (3) above, at least one of R3 and R4 represents an atomic bond that bonds to Y. It should be noted that, in one mode, Y and X preferably do not form a ring structure by means of bonding.Alternatively, in a preferred mode, Y preferably represents a substituted or unsubstituted hydrocarbon group. The hydrocarbon group that can be represented by Y is most preferably a hydrocarbon group with 1 to 5 carbon atoms, even more preferably a group represented by -(CH2)n- (where n is an integer from 1 to 5), even more preferably a group represented by (CH2)n- (where n is an integer from 1 to 3), and particularly preferably a methylene group (-CH2-) or an ethylene group (-CH2-CH2-). In a case where Y represents a comparatively small group, X, which includes an oxygen atom or a nitrogen atom, each being an electron-attracting atom, is positioned in the neighborhood of Y. Petition 870250091036, dated 06 / 10 / 2025, page 23 / 52 18 / 39 Z, so that the homogeneity of the aqueous solution and the separability of the PVA can be improved. Some or all of the hydrogen atoms of the hydrocarbon group, which can be represented by Y, can be replaced by a substituent. The substituent is preferably a carboxyl group, a salt of a carboxyl group, or an anion of a carboxyl group.

[0067] Z preferably represents a salt of a carboxyl group, a salt of a sulfo group, or a salt of a phosphoric acid group. Alternatively, in one mode, Z is also preferably a carboxyl group, a salt of a carboxyl group, or an anion of a carboxyl group, and most preferably a salt of a carboxyl group. In particular, in the case where compound (B) is present in a solution, particularly in an aqueous solution, Z may represent an anion (-COO-) of a carboxyl group, an anion (-SO3-) of a sulfo group, or an anion (-HPO4- or -PO42-) of a phosphoric acid group. Furthermore, in the case where Z represents a sulfo group (SO3H-) or a phosphoric acid group (H2PO4-), compound (B) may be a phosphoric acid ester or a sulfonic acid ester.

[0068] In the case where Z represents a salt of a carboxyl group, a salt of a sulfo group, or a salt of a phosphoric acid group, the type of salt is not particularly limited. Examples of the salt include: alkali metal salts of sodium, potassium, lithium, and the like; alkaline earth metal salts of calcium, magnesium, and the like; aluminum salts; zinc salts; ammonium salts; organic amine salts of monoethanolamine, diethanolamine, triethanolamine (TEA), triisopropanolamine, and the like; basic salts of arginine, lysine, and the like. The salt is preferably an alkali metal salt and, more preferably, a sodium salt. For example, by adding an alkali or an aqueous solution thereof to compound (B), which is a carboxylic acid, a sulfonic acid, or a phosphoric acid, compound (B), which is a salt of Petition 870250091036, dated 06 / 10 / 2025, page 24 / 52 19 / 39 The same can be obtained. For example, when an amine salt or an alkali metal salt of a subsequently described N-(long-chain acyl)amino acid needs to be obtained, an alkali or an aqueous solution thereof can be added to the N-(long-chain acyl)amino acid.

[0069] R1 preferably represents an acyl group. In the case where R1 represents an acyl group, R1 preferably represents a group represented by the following formula (4). Here, in formula (4), R5 represents a saturated or unsaturated hydrocarbon group with 7 to 20 carbon atoms, which may have a substituent. THE

[0070] R5 preferably represents a saturated or unsaturated hydrocarbon group with 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 addition, in one mode, the acyl group is preferably derived from coconut oil.

[0071] Furthermore, in the case where R1 represents a hydrocarbon group, the hydrocarbon group is preferably a saturated or unsaturated hydrocarbon group with 7 to 21 carbon atoms, more preferably a saturated or unsaturated linear hydrocarbon group with 7 to 21 carbon atoms, and even more preferably a saturated linear hydrocarbon group having 7 to 21 carbon atoms. It is preferable that R1 represents an n-octyl group, an n-decyl group, a lauryl group, or an n-tetradecyl group.

[0072] In one way, compound (B) is preferably a compound represented by formula (1), where X represents the group Petition 870250091036, dated 06 / 10 / 2025, page 25 / 52 20 / 39 represented by the above formula (2), and R1 represents an acyl group. In one mode, it is more preferred that: X represents the group represented by the above formula (2); Y represents a hydrocarbon group with 1 to 5 carbon atoms; Z represents a salt of a carboxylic group; R1 represents a group represented by the formula (4); R2 represents an alkyl group with 1 to 3 carbon atoms; and R5 represents a linear saturated hydrocarbon group having 9 to 13 carbon atoms.

[0073] Furthermore, in one embodiment, compound (B) is preferably at least one selected from the group consisting of an N-acyl amino acid salt and an acyl lactic acid salt. The acyl amino acid salt is preferably an N-acyl amino acid salt. The N-acyl amino acid salt preferably has an acyl group derived from a saturated or unsaturated fatty acid with 8 to 20 carbon atoms.

[0074] Furthermore, in one embodiment, compound (B) is preferably at least one selected from the group consisting of a phosphoric acid ester salt, an N-acyl amino acid salt, an acyl lactic acid salt, an acyl taurine salt, soap (a higher fatty acid), an alkyl sulfosuccinic acid salt, an acyl hydrolyzed collagen salt and an acyl isethionic acid salt, more preferably at least one selected from the group consisting of an acyl lactic acid salt and an acyl amino acid salt, even more preferably an acyl amino acid salt and even more preferably an N-acyl amino acid salt.

[0075] As a salt of an N-acyl amino acid salt, a salt of an N-acyl amino acid (hereinafter referred to as a long-chain N-(acyl)amino acid salt) is preferred, obtained by introducing into an amino group of an amino acid an acyl group derived from a saturated or unsaturated fatty acid with 8 to 20 carbon atoms. Petition 870250091036, dated 06 / 10 / 2025, p. 26 / 52 21 / 39 An amino acid residue of the N-acyl amino acid salt can be any of several types of amino acids, such as an α-amino acid, a β-amino acid, a γ-amino acid, or an ω-amino acid, and the amino group can be an N-methylamino group or an N-ethylamino group. Furthermore, the optical isomer, that is, whether it is a D form, an L form, or a racemic form, is not restricted.Examples of amino acid residues of N-acyl amino acid salts 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-methyl lanthionine, cystathionine, djenkolic acid, felinine, aminomalonic acid, β-oxyaspartic acid, α-amino-α-methylsuccinic acid, β-oxyglutamic acid, γ-oxyglutamic acid, γ-methylglutamic acid, γ-methyleneglutamic acid, acid γ-methyl-γoxyglutamic 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, α-aminosebacic acid and the like, sarcosine being preferred.

[0076] The acyl group in the acyl lactic acid salt and in the acyl amino acid salt is preferably derived from saturated or unsaturated fatty acids with 8 to 20 carbon atoms, as described above, and its linear, branched, or cyclic form is not restricted. Examples of fatty acids 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 arachidic acid; branched fatty acids, such as 2-butyl-5-methylpentanoic acid, 2-isobutyl-5-methylpentanoic acid, dimethylocta Petition 870250091036, dated 06 / 10 / 2025, page 27 / 52 22 / 39 nicotinic 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, 2-butyl-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, butylpentylheptanoic acid, trimethyltridecanoic acid, methylhexadecanoic acid, ethylpentadecanoic acid, propyltetradecanoic acid, butyltridecanoic acid, pentyldodecanoic acid, hexylundecanoic acidheptyldecanoic acid, methylheptylnonanoic acid, dipentylheptanoic acid, methylheptadecanoic acid, ethylhexadecanoic acid, ethylhexadecanoic acid, propylpentadecanoic acid, butyltetradecanoic acid, pentyltridecanoic acid, hexyldodecanoic acid, heptylundecanoic acid, octyldecanoic acid, dimethylhexadecanoic acid, methyloctadecanoic acid, ethylheptadecanoic acid, dimethylheptadecanoic acid, methyloctadecanoic acid, methylnonadecanoic acid, methylnonadecanoic acid, methylnonadecanoic acid, dimethyloctadecanoic acid and butylheptylnonanoic acid; linear monoenoic acids, such as octenoic acid, nonenoic acid, decenoic acid, caproleic acid, undecylenic acid, linderic acid, obtusilic acid, lauroleic acid, tridecenoic acid, tsuzuic acid, myristoleic acid, pentadecenoic acid, hexadecenoic acid, palmitoleic acid, heptadecenoic acid, octadecenoic acid, oleic acid,nonadecenoic acid and gondoic acid; branched monoenoic acids, such as methylheptenoic acid, methylheptenoic acid. Petition 870250091036, dated 06 / 10 / 2025, page 28 / 52, 23 / 39 Inonenoic acid, methylundecenoic acid, dimethyldecenoic acid, methyldodecenoic acid, methyltridecenoic acid, dimethyldodecenoic acid, dimethyltridecenoic acid, methyloctadecenoic acid, dimethylheptadecenoic acid and ethyloctadecenoic acid; dienoic or trienoic acids, such as linoleic acid, linoelaidic acid, eleostaric acid, linolenic acid, linolenaic acid, pseudoeleostaric acid, parinaric acid and arachidonic acid; acetylenic acids, such as octinoic acid, noninoic acid, decinoic acid, undecinoic acid, dodecinoic acid, tridecinoic acid, tetradecinoic acid, pentadecinoic acid, heptadecinoic acid, octadecinoic acid, nonadecinoic acid and dimethyloctadecinoic acid; and cyclic acids, such as methylene octadecenoic acid, methylene octadecanoic acid, aleprolic acid, alepristic acid, alepric acid, hydnocarpic acid, chaulmoogric acid, gorlic acid, α-cyclopentylic acid,α-cyclohexyl acid and α-cyclopentylethylic acid, from which the acyl group is derived, with lauric acid being preferred. Alternatively, the acyl group may be derived from a fatty acid obtained from a natural fat or oil, preferably an acyl group derived from mixed fatty acids containing 80% or more of saturated or unsaturated fatty acid(s) with 8 to 20 carbon atoms as described above. Examples include acyl groups derived from fatty acids of coconut oil, fatty acids of palm oil, fatty acids of linseed oil, fatty acids of sunflower oil, fatty acids of soybean oil, fatty acids of sesame oil, fatty acids of castor oil, fatty acids of olive oil, or fatty acids of camellia oil.

[0077] In the case where compound (B) is the acyl amino acid salt, examples of 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 sarcosinate, TEA sarcosinate, Petition 870250091036, dated 06 / 10 / 2025, page 29 / 52 24 / 39 cocoyl, potassium cocoyl sarcosinate, sodium lauroyl sarcosinate, TEA-lauroyl sarcosinate, potassium lauroyl sarcosinate, sodium cocoyl aspartate, TEA-cocoyl aspartate, potassium cocoyl aspartate, sodium lauroyl aspartate, TEA-lauroyl aspartate, potassium lauroyl aspartate, sodium cocoyl methyl alaninate, TEA-cocoyl methyl alaninate, potassium methyl cocoyl alaninate, sodium methyl lauroyl alaninate, TEA-cocoyl methyl alaninate, potassium methyl lauroyl alaninate, sodium cocoyl glycinate, TEA-cocoyl glycinate, potassium cocoyl glycinate, sodium lauroyl glycinate, TEA-lauroyl glycinate, potassium lauroyl glycinate, myristoyl sodium sarcosinate, TEA-myristoyl sarcosinate, potassium myristoyl sarcosinate, sodium lauroyl methyl-β-alaninate, TEA-lauroyl methyl-p-alaninate, potassium lauroyl methyl-β-alaninate, sodium cocoyl methyl-p-alaninate, TEA-cocoyl methyl-β-alaninate,Potassium cocoyl methyl-p-alaninate and similar compounds are available, and sodium lauroyl sarcosinate is more preferred.

[0078] In the case where compound (B) is the acyl lactic acid salt, preferred examples of acyl lactic acid salts include sodium cocoyl lactate, TEA-cocoyl lactate, potassium cocoyl lactate, sodium lauroyl lactate, TEA-lauroyl lactate, potassium lauroyl lactate, sodium stearoyl lactate, TEA-stearoyl lactate, potassium stearoyl lactate, sodium isostearolyl lactate, TEA-isostearoyl lactate, potassium isostearolyl lactate and the like.

[0079] Furthermore, in one mode, compound (B) is preferably at least one selected from the group consisting of an acid with an acid dissociation constant (pKa) in water of 0 or more and 6.0 or less, a salt thereof, and an anion thereof. The lower limit of the pKa is preferably 0, more preferably 1.0, and even more preferably 1.5. Furthermore, the upper limit of the pKa is preferably 6.0, more preferably 5.5, and even more preferably 5.0. When compound (B) is an acid with pKa Petition 870250091036, dated 06 / 10 / 2025, p. 30 / 52 25 / 39 within the above range, or a salt thereof, the solubility of PVA (A) in the composition being in the form of an aqueous solution containing PVA (A) and compound (B) may be higher, and the separation of PVA (A) in the aqueous solution under weakly acidic conditions may be higher.

[0080] The composition of the present invention may contain two or more types of compound (B) described above.

[0081] The composition of the present invention may consist only of PVA (A) and compound (B), or it may also contain other component(s) in addition to PVA (A) and compound (B). The other component is exemplified by polymers other than PVA (A), surfactants other than compound (B), solvents such as water and the like. Furthermore, optional components that may be contained in the composition for each intended use described below may also be involved in the other component(s). The composition may be a liquid, a paste, or a solid, such as a powder or a film. The lower limit of the total content of PVA (A) and compound (B) in the composition may be 1% by mass, or it may be 5% by mass, 10% by mass, 20% by mass, 30% by mass, 40% by mass, 50% by mass, 60% by mass, 70% by mass, 80% by mass, 90% by mass, 95% by mass, 97% by mass 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 it may be 99% by mass, 95% by mass, 90% by mass, 80% by mass, 70% by mass, 60% by mass, 50% by mass, 40% by mass, 30% by mass, 20% by mass, 10% by mass or 5% by mass.

[0082] The composition of the present invention may be, as described below, an aqueous solution containing water as another component. The lower limit of the total content of PVA (A), compound (B) and water in the composition is preferably 70% by mass, more preferably Petition 870250091036, dated 06 / 10 / 2025, page 31 / 52 26 / 39 Preferably 80% by mass and even more preferably 90% by mass, or it may be 95% by mass, 97% by mass, 99% by mass 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, or it may be 99.9% by mass or 99% by mass. In the case where the composition is an aqueous solution, the content of PVA (A) may be, for example, 1% by mass or more and 40% by mass or less, it may be 5% by mass or more and 35% by mass or less, or it may be 10% by mass or more and 30% by mass or less.

[0083] The composition of the present invention may consist substantially only of PVA (A) and compound (B). An aqueous solution containing such composition and water, a mixture of such composition and other component(s), and the like, are also suitable for an embodiment of the present invention. The mixture also involves an aqueous solution and the like. Intended uses

[0084] One embodiment of the composition of the present invention is at least one composition selected from the group consisting of a composition for agricultural supplies, a composition for automotive supplies, a composition for aeronautical supplies, a composition for industrial supplies, a composition for livestock supplies, a composition for marine supplies, a pharmaceutical composition, a composition for personal care products, a composition for recreational products and a composition for water treatment agents.

[0085] The term agricultural supplies herein refers to supplies and materials used in agriculture and horticulture. The typical composition of agricultural supplies is exemplified by agrochemical compositions, and examples thereof include insecticides, fungicides, insecticidal fungicides, herbicides, rodenticides, growth regulators, Petition 870250091036, dated 06 / 10 / 2025, page 32 / 52 27 / 39 Plant cement, attractants, spreaders, repellents, defoliants, fertilizers, trace elements and micronutrients and similar products.

[0086] In the case where the composition is an agrochemical composition, the composition may contain, in addition to PVA (A) and compound (B), a medium such as water, as well as active ingredient(s) to confer the desired action(s) and / or function(s). The active ingredient is exemplified by insecticides, herbicides and the like.

[0087] The term automotive supplies, as used herein, means supplies and materials used in the automotive industry. Examples of the composition of automotive supplies include car wash detergents, windshield washer fluids, and the like.

[0088] The term aeronautical supplies, as used herein, means supplies and materials used in the aeronautical industry. Examples of the composition of aeronautical supplies include fuselage cleaners and similar items.

[0089] The term industrial supplies, as used herein, means supplies and materials used in the manufacturing industry. Examples of the composition of industrial supplies include machine cleaning agents, dispersants for the polymerization of vinyl compounds and the like. Preferred dispersants for the polymerization of vinyl compounds include dispersants for the suspension polymerization of vinyl chloride.

[0090] The term livestock supplies, as used herein, means supplies and materials used in the production of milk and livestock. Examples of livestock supplies include barn cleaners, farm equipment cleaners, and similar items.

[0091] The term maritime supplies, as referred to herein, means supplies and materials used in fishing, in fishing, in Petition 870250091036, dated 06 / 10 / 2025, page 33 / 52 28 / 39 shipbuilding, ocean exploration and similar. Examples of composition for maritime supplies include cleaning agents for ships, cleaning agents for ship equipment, cleaning agents for marine processing equipment and similar.

[0092] Pharmaceutical compositions include pharmaceutical products, near-drugs and the like.

[0093] The term personal care products, as used herein, means products that can be applied to the bodies of humans or non-human animals. It should be noted that the body referred to herein includes skin, teeth, nails and hair. Examples of personal care products include cosmetics, shampoos, liquid soaps, facial cleansers, toothpaste and the like.

[0094] In the case of the composition being for personal hygiene products, the composition may contain, in addition to PVA (A) and compound (B), for example, water, a thickening agent, a flavoring ingredient, a colorant, a dispersant, an exfoliating agent, an emulsifying agent, a moisturizer, a bleaching agent, etc.

[0095] The term recreational goods referred to here means Products and materials used in recreational activities. Examples of compositions for recreational products include foam sprays, bath additives, foaming agents for swimming pools and the like.

[0096] The term water treatment agents, as referred to herein, means agents used by addition to water or a liquid containing water as a principal component (containing at least 50% water by mass relative to the total mass) for the purpose of preventing the generation of microorganisms, preventing corrosion, preventing scaling and the like. Examples of composition for water treatment agents include water treatment agents for water supply, industrial water treatment agents, agents Petition 870250091036, dated 06 / 10 / 2025, page 34 / 52 29 / 39 sewage treatment, industrial wastewater treatment agents, swimming pool water purification agents and similar products.

[0097] In the case where the composition is a composition for water treatment agents, the composition may contain, in addition to PVA (A) and compound (B), a medium such as water, as well as a polymeric coagulant and / or an inorganic coagulant composed of a water-soluble (co)polymer having a water-soluble monomer as a constituent unit, and the like. Aqueous solution

[0098] The composition of the present invention may be an advanced aqueous solution containing water. Such an aqueous solution is an aqueous solution in which PVA (A), which is sparingly soluble in water and difficult to dissolve in water alone, is solubilized in water by the action of compound (B). Conventionally, it has been difficult to separate and extract dissolved PVA from an aqueous PVA solution once prepared, as this requires the use of a large amount of a salt and a weak solvent. In the present invention, since the solubilizing capacity 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.

[0099] It is preferable that the aqueous solution (composition) can be separated into two phases, a clear supernatant liquid and a resin precipitate, in which case the pH of the aqueous solution is adjusted to 3.0 at room temperature. Such an aqueous solution facilitates the filtration of the PVA (A) contained in the aqueous solution. The mass of the resin precipitate after drying the resin precipitate obtained by filtration at 105°C for 24 hours is preferably 70% by mass or more relative to the PVA (A) originally contained in the aqueous solution. Petition 870250091036, dated 06 / 10 / 2025, p. 35 / 52 30 / 39

[00100] In a state prior to the separation operation of the PVA (A) contained in the aqueous solution, that is, a state in which the PVA (A) and the compound (B) are dissolved in water, the aqueous solution, such as the composition of the present invention, is preferably a clear and homogeneous liquid at room temperature. The aqueous solution, such as the composition of the present invention, has a pH preferably of 4.0 to 11.0, but may be 5.0 to 10.0, 5.5 to 9.0 or 6.0 to 8.0.

[00101] Method for separating vinyl alcohol polymer

[00102] The method for separating a vinyl alcohol polymer of the present invention is a method including: adjusting the pH of the composition described above, which is an aqueous solution, to precipitate at least part of the PVA(A) contained in the aqueous solution (composition). In one embodiment, it is preferable that the pH of the aqueous solution be adjusted to 3.0 or less to precipitate a resin precipitate containing the PVA(A). Furthermore, it is preferable that the mass of resin precipitated after drying the filtered resin precipitate at 105°C for 24 hours accounts for 70% by mass or more of the PVA(A) originally contained in the aqueous solution. EXAMPLES

[00103] The present invention is described in more detail below by means of Examples, but the present invention is in no way limited by the Examples.

[00104] Next, RT, the mean degree of polymerization of viscosity and the degree of saponification of PVA (A) in the composition were measured and calculated for compositions used in the Examples and Comparative Examples according to the methods described below. PVA retention time RT

[00105] The retention time (RT) of PVA is the peak retention time, measured by high-performance liquid chromatography with a grid. Petition 870250091036, dated 06 / 10 / 2025, p. 36 / 52 31 / 39 reversed-phase partitioning, using a liquid mixture of water / ethanol with ion exchange as eluent. The measurement was performed under the following conditions. It should be noted that the peak is the point where the detection intensity is maximum and exhibits a maximum value in a chromatogram obtained by chromatographic determination. Measurement Conditions column: Shimpack G-ODS (4) (manufactured by Shimadzu Corporation, fully porous spherical silica gel modified by octadecyl group; internal diameter of 4 mm χ length of 10 mm; particle diameter: 5 μm) column temperature: 45°C eluent: a liquid mixture of water exchanged by ions (X) and ethanol (purity: 99.5%) (Y) eluent composition for each measurement time; at 5 min: concentration of (Y) being 5% by volume, constant at 25 min: concentration of (Y) being 5% to 100% by volume at 40 min: concentration of (Y) being 100% by volume, constant at 41 min: concentration of (Y) being 100% to 5% by volume at 55 min: concentration of (Y) being 5% by volume, constant (The concentration of (Y) from 5 min to 25 min was gradually increased from 5% by volume to 100% by volume at a substantially constant rate. The concentration of (Y) from 40 to 41 min was gradually decreased from 100% by volume to 5% by volume at a substantially constant rate.) Mobile phase flow rate: 0.4 mL / min Petition 870250091036, dated 06 / 10 / 2025, p. 37 / 52 Sample concentration: 5 mg / mL; detector: ELSD-LTII (manufactured by Shimadzu Corporation; bypass tube temperature: 40°C; gain: 6 (= 32 times); primary N2 gas spray pressure: 0.4 MPa; secondary spray pressure: 0.35 MPa; data acquisition interval: 1000 ms; filter: 1 s); injection quantity: 5 μL; length h from injection to column inlet: 900 mm; length from column outlet to ELSD-LTII detector nebulizer: 1375 mm; tube diameter: 0.3 mm ID Viscosity - Average Degree of Polymerization of PVA

[00106] The average degree of polymerization of PVA viscosity was determined according to JIS K 6726: 1994. Specifically, in a case where the PVA has a degree of saponification less than 99.5 mol%, saponification was carried out until the degree of saponification became 99.5 mol% or more, and the PVA thus obtained was subjected to the determination of the average degree of polymerization of viscosity by the following equality, using an intrinsic viscosity [η] (liter / g) measured in water at 30°C.

[00107] viscosity-average degree of polymerization = ([η] x 104 / 8.29)(1 / °.62)

[00108] Degree of saponification of PVA

[00109] The degree of saponification (mol%) of PVA was measured according to JIS K 6726: 1994.

[0079] Production example 1

[00110] In a 3 L reaction tank equipped with a stirrer, a nitrogen feed port, an additive feed port, and an initiator addition port, 480 g of vinyl acetate and 1,120 g of methanol were loaded and after the temperature was raised Petition 870250091036, dated 06 / 10 / 2025, page 38 / 52 33 / 39 of the reaction tank was heated to 60°C, and the interior of the system was replaced with nitrogen by bubbling nitrogen for 30 min. The internal temperature of the reaction tank was adjusted to 60°C, and 1.2 g of 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile) was added to initiate polymerization. During polymerization, the polymerization temperature was maintained at 60°C, and after 5 hours, when the degree of polymerization reached 70%, polymerization was stopped by cooling. Then, the unreacted vinyl acetate was removed under reduced pressure, resulting in a polyvinyl acetate solution in methanol. Saponification was enabled by adding a 10% by mass concentration of NaOH in methanol to the polyvinyl acetate solution in methanol. adjusted to 30%, so that the alkaline molar ratio (number of moles of NaOH / number of moles of vinyl ester unit in polyvinyl acetate) was 0.0025, obtaining PVA 1 as PVA (A).The degree of saponification, the average degree of polymerization in terms of viscosity, and the retention time (RT) of the PVA 1 thus obtained are shown in Table 1. Production Example 2

[00111] In a 3 L reaction tank equipped with a stirrer, a nitrogen feed port, an additive feed port, and an initiator addition port, 1.284 g of vinyl acetate, 316 g of methanol, and 0.107 g of 3-mercaptopropionic acid were loaded. After the temperature was raised to 60°C, the interior of the system was replaced with nitrogen by bubbling nitrogen for 30 min. The internal temperature of the reaction tank was adjusted to 60°C, and 4.58 g of methanol containing 0.51 g of 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile) were added to initiate polymerization. Immediately, 23.30 g of methanol containing 2.33 g of 3-mercaptopropionic acid were added homogeneously over 4 hours. During polymerization, the polymerization temperature of Petition 870250091036, dated 06 / 10 / 2025, page 39 / 52 34 / 39 A temperature of 60°C was maintained, and after 4 hours, when the degree of polymerization reached 65%, the polymerization was stopped by cooling. Then, the unreacted vinyl acetate was removed under reduced pressure to provide a polyvinyl acetate solution in methanol. Saponification was enabled by adding a NaOH solution in methanol (10% by mass concentration) to the polyvinyl acetate solution in methanol adjusted to 50%, so that an alkaline molar ratio (number of moles of NaOH / number of moles of vinyl ester unit in polyvinyl acetate) became 0.009, obtaining PVA 2 as PVA (A). The degree of saponification, the degree of polymerization viscosity-average, and the retention time RT of the PVA 2 thus obtained are shown in Table 1. Production Example 3

[00112] In a 3 L reaction tank equipped with a stirrer, a nitrogen feed port, an additive feed port, and an initiator addition port, 720 g of vinyl acetate and 880 g of methanol were loaded and, after the temperature was raised to 60°C, the interior of the system was replaced with nitrogen by bubbling nitrogen for 30 min. The internal temperature of the reaction tank was adjusted to 60°C and 1.2 g of 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile) was added to initiate polymerization. During polymerization, the polymerization temperature of 60°C was maintained and, after 5 hours, when the degree of polymerization reached 70%, the polymerization was stopped by cooling. Then, the unreacted vinyl acetate was removed under reduced pressure to generate a solution of polyvinyl acetate in methanol.Saponification was achieved by adding a solution of NaOH in methanol (concentration of 10% by mass) to a solution of polyvinyl acetate in methanol, adjusted to 30%, so that the alkaline molar ratio (number of moles of NaOH / number of moles of vinyl ester unit in polyvinyl acetate) was 10%. Petition 870250091036, dated 06 / 10 / 2025, pages 40 / 52 35 / 39 livinyl) was 0.0037, obtaining PVA 3. The degree of saponification, the degree of polymerization in relation to the average viscosity, and the retention time (RT) of the PVA 3 thus obtained are presented in Table 1. Table 1 Degree of saponification (mol%) Average viscosity - degree of polymerization RT (min) PVA 1 50 250 23 PVA 2 40 250 24 PVA 3 75 500 21 Compound (B)

[00113] The surfactants used in the Examples and Comparative Examples, such as compound (B), are shown in Table 2. Table 2 Component Designation | Surfactant Category | 1 (SOYPON SLP) | Anionic sodium lauroyl sarcosinate surfactant | 2 (Aminosurfact ACDS-L) | Anionic sodium cocoyl glutamate surfactant | 3 (ALANON ALE) | Anionic sodium lauroyl methyl alaninate surfactant | 4 (EMAL 10G) | Anionic sodium lauryl sulfate surfactant | 5 (QUARTAMIN 86P CONC.) | Cationic stearyl trimethyl ammonium chloride surfactant | 6 (EMULGEN 150) | Nonionic polyoxyethylene (47) lauryl ether Example 1

[00114] To 79 parts by mass of ion-exchanged water were added 20 parts by mass of PVA 1 and, as a surfactant, 1 part by mass of SOYPON SLP (manufactured by Kawaken Fine Chemicals Co., Ltd., where SOYPON is a registered trademark), surfactant 1 being described above, and the mixture was heated with stirring. Petition 870250091036, dated 06 / 10 / 2025, pages 41 / 52 36 / 39 resulted in an aqueous solution, with the following composition. Example 2

[00115] To 76 parts by mass of ion-exchanged water were added 20 parts by mass of PVA 1 and as a surfactant, 4 parts by mass of Aminosurfact ACDS-L (manufactured by Asahi Kasei Finechem Co., Ltd., active ingredient: 25%, where Aminosurfact is a registered trademark.), the surfactant being described above 2, and heating with stirring of the mixture gave an aqueous solution, the composition being. Example 3

[00116] To 67.6 parts by mass of ion-exchanged water were added 30 parts by mass of PVA 1 and, as a surfactant, 2.4 parts by mass of ALANON ALE (manufactured by Kawaken Fine Chemicals Co., Ltd., active ingredient: 30%, where ALANON is a registered trademark), the surfactant being described above 3, and heating with stirring of the mixture resulted in an aqueous solution, the composition being. Example 4

[00117] To 79 parts by mass of ion-exchanged water were added 20 parts by mass of PVA 2 and, as a surfactant, 1 part by mass of SOYPON SLP (manufactured by Kawaken Fine Chemicals Co., Ltd.), the surfactant being described above 1, and heating with stirring of the mixture resulted in an aqueous solution, the composition being. Comparative Example 1

[00118] An aqueous solution, the composition being, was obtained in a manner similar to Example 1, except that the PVA used was changed to PVA 3. Comparative Example 2

[00119] An aqueous solution, with the composition, was obtained from Petition 870250091036, dated 06 / 10 / 2025, pages 42 / 52 37 / 39 form similar to Example 1, except that the surfactant has been changed to EMAL 10G (manufactured by Kao Corporation, where EMAL is a registered trademark), the surfactant being described above 4.

[0091] Comparative Example 3

[00120] An aqueous solution, with the composition, was obtained by: adding 20 parts by mass of PVA 1 to 80 parts by mass of ion-exchanged water; and heating the mixture with stirring. Comparative Example 4

[00121] To 78.4 parts by mass of ion-exchanged water were added 20 parts by mass of PVA 1 and, as a surfactant, 1.6 parts by mass of QUARTAMIN 86P CONC. (manufactured by Kao Corporation, active ingredient: 63%, where QUARTAMIN is a registered trademark), the surfactant being described above 5, and heating with stirring of the mixture resulted in an aqueous solution, the composition being. Comparative Example 5

[00122] An aqueous solution, the composition being, was obtained similarly to Example 1, except that the surfactant was changed to EMULGEN 150 (manufactured by Kao Corporation, where EMULGEN is a registered trademark), the surfactant being described above 6.

[0094] Evaluation of the liquid state of an aqueous solution.

[00123] In each aqueous solution thus obtained, the state of the liquid at normal temperature was visually observed. The aqueous solution was evaluated as: homogeneous in the case where the composition became a transparent and homogeneous liquid; or separated in the case where the composition was separated into two or more phases, or was suspended. Evaluation of separability after addition of acid. Petition 870250091036, dated 06 / 10 / 2025, pp. 43 / 52 38 / 39

[00124] Among the aqueous solutions prepared, the compositions evaluated as homogeneous in the Liquid State Assessment of the Aqueous Solution above were subjected to a separability assessment by adding an acid. After adjusting the liquid pH of the aqueous solution, as a subject, to 3.0 by adding 0.25 mol / L sulfuric acid, the state of the aqueous solution at normal temperature was visually observed. In this procedure, the aqueous solution was evaluated as: A in a case where the aqueous solution immediately separated into two phases of a clear supernatant liquid and a resin precipitate, so that filtration of the resin precipitate was permitted; or B in a case where the composition did not separate into a clear supernatant liquid phase and a resin precipitate phase, so that filtration of the resin precipitate was impossible.It should be noted that the phrase "the case in which filtration of the resin precipitate was permitted, as mentioned herein" means a case in which the mass of the resin precipitate, relative to the PVA originally contained in the composition, was 70% by mass or more after the resin precipitate obtained by filtration was dried at 105°C for 24 hours. It should be noted that the pH of the aqueous solution was measured using a pH meter (F-51, manufactured by HORIBA, Ltd.).

[00125] In relation to Example 1 and Comparative Examples 1 to 5, the results of the evaluation of the liquid state of the aqueous solution and the results of the evaluation of separability after the addition of acid are summarized in Table 3. The aqueous solution of Example 1 was a transparent and homogeneous aqueous solution, and the separation of PVA was possible under a weakly acidic condition. Petition 870250091036, dated 06 / 10 / 2025, pages 44 / 52 39 / 39 Table 3 PVA Surfactant Liquid State Separability after Acid Addition Example 1 PVA 1 surfactant 1 homogeneous A Example 2 PVA 1 surfactant 2 homogeneous A Example 3 PVA 1 surfactant 3 homogeneous A Example 4 PVA 2 surfactant 1 homogeneous A Comparative Example 1 PVA 3 surfactant 1 homogeneous B Comparative Example 2 PVA 1 surfactant 4 homogeneous B Comparative Example 3 PVA 1 - separated - Comparative Example 4 PVA 1 surfactant 5 separated - Comparative Example 5 PVA 1 surfactant 6 separated - Petition 870250091036, dated 06 / 10 / 2025, pages 45 / 52

Claims

1 / 3 CLAIMS 1. Composition, characterized in that it comprises: a vinyl alcohol polymer (A) having a peak retention time RT of 22 min or more, measured by high-performance liquid chromatography with reversed-phase gradient partitioning with a water-ethanol eluent; and a compound (B), wherein compound (B) is a compound represented by formula (1): IR^ m XZU) wherein, in formula (1), X represents an oxygen atom, a group represented by formula (2) or a group represented by formula (3); Y represents an atomic group with 1 to 10 carbon atoms; Z represents a selection of the group consisting of a carboxyl group, a sulfo group, a phosphoric acid group, a salt thereof and an anion thereof;and R1 represents an acyl group or a hydrocarbon group, R2 N (2) R3 R4 X <3> In formula (2) and formula (3), R2, R3 and R4 each independently represent a hydrogen atom, an alkyl group with 1 to 3 carbon atoms or an atomic bond that attaches to Y; and * denotes an atomic bond.

2. Composition according to claim 1, characterized in that, as for compound (B), Z in formula (1) represents a carboxylic group, a salt of a carboxylic group or an anion of a carboxylic group.

3. Composition according to claim 1, characterized in that, with respect to compound (B), X in formula (1) represents a group represented by formula (2), and R1 represents an acyl group.

4. Composition according to claim 1, characterized in that compound (B) is at least one selected from the group consisting of an N-acyl amino acid salt and an acyl lactic acid salt.

5. Composition according to claim 4, characterized in that compound (B) is the N-acyl amino acid salt.

6. Composition according to claim 5, characterized in that the N-acyl amino acid salt has an acyl group derived from a saturated or unsaturated fatty acid with 8 to 20 carbon atoms.

7. Composition according to claim 1, characterized in that in compound (B), R1 represents a group represented by formula (4): O wherein, in formula (4), R5 represents a saturated or unsaturated hydrocarbon group with 7 to 20 carbon atoms that may have a substituent; and * denotes an atomic bond.

8. Composition according to claim 1, characterized in that the vinyl alcohol polymer (A) has a degree of saponification of 20 mol% or more and 70 mol% or less.

9. Composition according to claim 1, characterized in that the vinyl alcohol polymer (A) consists only of a vinyl acetate-derived monomeric unit.

10. Composition, according to claim 1, characterized by the fact that it is at least one selected from the group consisting of a composition for agricultural supplies, a composition for automotive supplies, a composition for aeronautical supplies, a composition for industrial supplies, a composition for livestock supplies, a composition for marine supplies, a pharmaceutical composition, a composition for personal hygiene products, a composition for recreational products and a composition for water treatment agents.

11. Composition according to any one of claims 1 to 10, characterized in that it is an aqueous solution further comprising water.

12. Method for separating a vinyl alcohol polymer, the method characterized in that it comprises: adjusting the pH of the composition, as defined in claim 11, to precipitate at least a portion of the vinyl alcohol polymer (A) comprised in the composition. Petition 870250091036, dated 06 / 10 / 2025, pp. 48 / 52