Treatment agent for synthetic fiber and synthetic fiber

Abstract

The objective of this invention is to provide a synthetic fiber treatment agent capable of simultaneously improving the heat resistance of the treatment agent and its stability during storage, as well as synthetic fibers treated with the treatment agent. The synthetic fiber treatment agent of this invention comprises a smoothing agent (A), a nonionic surfactant (B), an ionic surfactant (C) comprising a phosphate ester compound (C1), and an alcohol compound (D). The phosphate ester compound (C1) comprises at least one selected from phosphate esters P1, P2, P3, and P4, each represented by a defined chemical formula, wherein when the total percentage of the NMR integral of the P-nuclei attributable to phosphate esters P1 to P4 is set to 100%, the percentage of the NMR integral of the P-nuclei attributable to phosphate ester P1 is 7% or less.

Description

Technical Field

[0001] The present invention includes a synthetic fiber treatment agent containing a specified phosphate ester compound, etc., and synthetic fibers to which the synthetic fiber treatment agent is attached. Background Technology

[0002] Typically, in the spinning and stretching process of synthetic fibers, in order to reduce friction and fiber damage such as breakage, a synthetic fiber treatment agent is sometimes applied to the surface of the synthetic fibers.

[0003] Previously known treatment agents for synthetic fibers were disclosed in Patent Documents 1 and 2. Patent Document 1 discloses a treatment agent for synthetic fibers containing a specified phosphate ester or its organic amine salt, a nonionic surfactant, etc., in a smoothing agent. Patent Document 2 discloses a treatment agent for synthetic fibers containing a specified organic sulfonic acid compound, an organic phosphate ester compound, a nonionic surfactant, etc.

[0004] Existing technical documents

[0005] Patent documents

[0006] Patent Document 1: Japanese Patent Application Publication No. 2015-038260

[0007] Patent Document 2: Japanese Patent Application Publication No. 2016-084566 Summary of the Invention

[0008] The problem that the invention aims to solve

[0009] However, existing synthetic fiber treatment agents suffer from reduced storage stability due to issues such as the precipitation of foreign matter over time. In particular, it is difficult to simultaneously improve both the heat resistance and storage stability of the treatment agent.

[0010] Methods for solving problems

[0011] In order to solve the above-mentioned problems, the inventors conducted research and found that it is appropriate to mix a smoothing agent, a nonionic surfactant, an alcohol compound, and a specific phosphate ester compound in the treatment agent for synthetic fibers.

[0012] To address the aforementioned issues, one aspect of the synthetic fiber treatment agent of the present invention is that it contains a smoothing agent (A), a nonionic surfactant (B), an ionic surfactant (C) comprising the following phosphate ester compound (C1), and an alcohol compound (D).

[0013] The phosphate compound (C1) includes at least one selected from phosphate ester P1 represented by chemical formula (1), phosphate ester P2 represented by chemical formula (2), phosphate ester P3 represented by chemical formula (3), and phosphate ester P4 represented by chemical formula (4), wherein when the total proportion of the P-nuclear NMR integrals attributable to the above-mentioned phosphate ester P1, the above-mentioned phosphate ester P2, the above-mentioned phosphate ester P3, and the above-mentioned phosphate ester P4 is set to 100%, the proportion of the P-nuclear NMR integrals attributable to the above-mentioned phosphate ester P1 is 7% or less.

[0014] [Chemistry 1]

[0015]

[0016] In chemical formula (1),

[0017] R 1 The residue obtained by removing the hydroxyl group from a substance formed by adding 8 or more but less than 24 carbon atoms to an alkyl group, an alkenyl group, or an epoxy alkane with 2 or more but less than 3 carbon atoms in a total of 1 or more but less than 20 moles of aliphatic alcohols with 8 or more but less than 24 carbon atoms.

[0018] M 1 and M 2 These are, respectively, hydrogen atoms, alkali metals, alkaline earth metals (1 / 2), organic amine salts, ammonium, or phosphonium.

[0019] m is an integer of 2 or 3.

[0020] [Chemistry 2]

[0021]

[0022] In chemical formula (2),

[0023] R 2 and R 3 The residues obtained by removing hydroxyl groups from substances formed by adding alkyl groups with 8 or more and 24 or fewer carbon atoms, alkenyl groups with 8 or more and 24 or fewer carbon atoms, or epoxides with 2 or more and 3 or fewer carbon atoms in a total of 1 or more and 20 moles of aliphatic alcohols with 8 or more and 24 or fewer carbon atoms relative to 1 mole.

[0024] M 3 It can be hydrogen atom, alkali metal, alkaline earth metal (1 / 2), organic amine salt, ammonium, or phosphonium.

[0025] n is an integer of 2 or 3.

[0026] [Chemistry 3]

[0027]

[0028] In chemical formula (3),

[0029] R 4 The residue obtained by removing the hydroxyl group from a substance formed by adding 8 or more but less than 24 carbon atoms to an alkyl group, an alkenyl group, or an epoxy alkane with 2 or more but less than 3 carbon atoms in a total of 1 or more but less than 20 moles of aliphatic alcohols with 8 or more but less than 24 carbon atoms.

[0030] M 4 and M 5 These are hydrogen atoms, alkali metals, alkaline earth metals (1 / 2), organic amine salts, ammonium, or phosphorus.

[0031] [Chemistry 4]

[0032]

[0033] In chemical formula (4),

[0034] R 5 and R 6 The residues obtained by removing hydroxyl groups from substances formed by adding alkyl groups with 8 or more and 24 or fewer carbon atoms, alkenyl groups with 8 or more and 24 or fewer carbon atoms, or epoxides with 2 or more and 3 or fewer carbon atoms in a total of 1 or more and 20 moles of aliphatic alcohols with 8 or more and 24 or fewer carbon atoms relative to 1 mole.

[0035] M 6 It can be hydrogen atom, alkali metal, alkaline earth metal (1 / 2), organic amine salt, ammonium, or phosphorus.

[0036] In the above-mentioned synthetic fiber treatment agent, the above-mentioned phosphate compound (C1) includes the above-mentioned phosphate ester P2. When the total proportion of the P-nucleus NMR integral of the above-mentioned phosphate ester P1, the above-mentioned phosphate ester P2, the above-mentioned phosphate ester P3, and the above-mentioned phosphate ester P4 is set to 100%, the proportion of the P-nucleus NMR integral of the above-mentioned phosphate ester P2 can be 5% or more and 50% or less.

[0037] In the above-mentioned synthetic fiber treatment agent, the above-mentioned phosphate compound (C1) includes the above-mentioned phosphate ester P2. When the total proportion of the P-nucleus NMR integral of the above-mentioned phosphate ester P1, the above-mentioned phosphate ester P2, the above-mentioned phosphate ester P3, and the above-mentioned phosphate ester P4 is set to 100%, the proportion of the P-nucleus NMR integral of the above-mentioned phosphate ester P1 can be 5% or less, and the proportion of the P-nucleus NMR integral of the above-mentioned phosphate ester P2 can be 10% or more and 45% or less.

[0038] In the above-mentioned synthetic fiber treatment agent, the alcohol compound (D) may include at least one selected from monohydric alcohols and dihydric alcohols.

[0039] In the above-mentioned synthetic fiber treatment agent, the alcohol compound (D) includes a monohydric alcohol, and the content of the monohydric alcohol in the above-mentioned synthetic fiber treatment agent can be more than 0.0001% by mass and less than 3% by mass.

[0040] In the above-mentioned synthetic fiber treatment agent, the alcohol compound (D) includes diol, and the proportion of diol in the above-mentioned synthetic fiber treatment agent can be more than 0.001% by mass and less than 5% by mass.

[0041] In the above-mentioned synthetic fiber treatment agent, the smoothing agent (A) may contain at least one selected from the following complete ester compound (A1), sulfur-containing ester compound (A2), and the following partial ester compound (A3).

[0042] The complete ester compound (A1) is selected from at least one of a complete ester compound of a polyol having a chain structure with 3 or more and 6 or fewer carbon atoms and a monobasic fatty acid having 8 or more and 24 or fewer carbon atoms, and a complete ester compound of a monobasic alcohol having 8 or more and 24 or fewer carbon atoms and a polybasic fatty acid having 3 or more and 10 or fewer carbon atoms.

[0043] Ester compounds (A3) are ester compounds of polyols with a chain structure having 3 or more but less than 6 carbon atoms and monobasic fatty acids having 8 or more but less than 24 carbon atoms.

[0044] In the above-mentioned synthetic fiber treatment agent, the smoothing agent (A) contains the above-mentioned complete ester compound (A1), and the content of the above-mentioned complete ester compound (A1) in the above-mentioned synthetic fiber treatment agent can be more than 30% by mass and less than 70% by mass.

[0045] In the above-mentioned synthetic fiber treatment agent, the above-mentioned smoothing agent (A) may contain the above-mentioned sulfur-containing ester compound (A2).

[0046] In the above-mentioned synthetic fiber treatment agent, the content ratio of the above-mentioned complete ester compound (A1) and the above-mentioned sulfur-containing ester compound (A2) by mass ratio can be more than 1 / 1 and less than 100 / 1.

[0047] In the above-mentioned synthetic fiber treatment agent, the above-mentioned smoothing agent (A) may contain the above-mentioned ester compound (A3).

[0048] In the above-mentioned synthetic fiber treatment agent, the content ratio of the above-mentioned complete ester compound (A1) and the above-mentioned partial ester compound (A3) by mass ratio can be more than 1 / 1 and less than 10000 / 1.

[0049] In the above-mentioned synthetic fiber treatment agent, the concentration of phosphate ions detected by ion chromatography in the synthetic fiber treatment agent can be below 200 ppm.

[0050] To address the aforementioned issues, another aspect of the synthetic fiber of the present invention is that it is coated with the aforementioned synthetic fiber treatment agent.

[0051] The effects of the invention

[0052] According to the present invention, it is possible to achieve both improved heat resistance and improved stability during storage of the treatment agent for synthetic fibers. Detailed Implementation

[0053] <First Implementation>

[0054] The following describes a first embodiment of the synthetic fiber treatment agent (hereinafter referred to as the treatment agent) of the present invention. The treatment agent of this embodiment contains a smoothing agent (A), a nonionic surfactant (B), an ionic surfactant (C) comprising a phosphate ester compound (C1), and an alcohol compound (D). Unlike the acrylic fiber treatment agent for carbon fiber manufacturing disclosed, for example, in International Publication No. 2013 / 129115, the treatment agent is preferably used for treating synthetic fibers other than acrylic fibers for carbon fiber manufacturing.

[0055] (Smoothing Agent (A))

[0056] Examples of smoothing agents (A) include silicone oil, mineral oil, polyolefins, and ester oils. Smoothing agents (A) impart smoothness to synthetic fibers.

[0057] There are no particular limitations on specific examples of silicone oils, such as dimethyl silicone, phenyl-modified silicone, amino-modified silicone, amide-modified silicone, polyether-modified silicone, amino-polyether-modified silicone, alkyl-modified silicone, alkylaralkyl-modified silicone, alkyl-polyether-modified silicone, ester-modified silicone, epoxy-modified silicone, methanol-modified silicone, mercapto-modified silicone, and polyoxyalkylene-modified silicone. Commercially available silicone oils may be suitable.

[0058] Examples of mineral oils include aromatic hydrocarbons, alkane hydrocarbons, and cycloalkanes. More specifically, examples include spindle oils and liquid paraffin. Commercially available mineral oils may be suitable. The kinematic viscosity of the mineral oil used is 5 mm at 40°C. 2 Substances with a density of more than / s.

[0059] Polyolefins can be used as smoothing agents, such as poly-α-olefins. Specific examples of polyolefins include poly-α-olefins obtained by polymerizing 1-butene, 1-hexene, 1-decene, etc. Commercially available poly-α-olefins are suitable.

[0060] There are no particular limitations on ester oils; examples can be made from fatty acids and alcohols. For instance, ester oils made from fatty acids having an odd or even number of hydrocarbon groups, as described later, can be cited as examples.

[0061] The fatty acids used as raw materials for ester oils are not particularly restricted in terms of their number of carbon atoms, whether they have branches or not, or their number of atoms. For example, they can be higher fatty acids, cyclic fatty acids, or aromatic fatty acids. Similarly, the alcohols used as raw materials for ester oils are not particularly restricted in terms of their number of carbon atoms, whether they have branches or not, or their number of atoms. For example, they can be higher alcohols, cyclic alcohols, or aromatic alcohols.

[0062] The ester oil preferably contains at least one selected from a complete ester compound (A1), a sulfur-containing ester compound (A2), and a metaester compound (A3). Furthermore, the sulfur-containing ester compound (A2) is more preferably included as the ester oil. This configuration allows for the suppression of tension variations by improving heat resistance. Additionally, the metaester compound (A3) is more preferably included as the ester oil. This configuration allows for the suppression of tar by improving compatibility.

[0063] The complete ester compound (A1) is selected from at least one of the following: a complete ester compound of a polyol having a chain structure with 3 or more and 6 or fewer carbon atoms and a monobasic fatty acid having 8 or more and 24 or fewer carbon atoms; and a complete ester compound of a monobasic alcohol having 8 or more and 24 or fewer carbon atoms and a polybasic fatty acid having 3 or more and 10 or fewer carbon atoms. Dicarboxylic acids containing sulfur atoms in their molecules, such as thiodipropionic acid or dithiodipropionic acid, are not included in the polybasic fatty acids of the ester compound (A1).

[0064] Ester compounds (A3) are ester compounds consisting of polyols with a chain structure having 3 or more but less than 6 carbon atoms and monobasic fatty acids having 8 or more but less than 24 carbon atoms.

[0065] Polyols with a chain structure can include those without a cyclic structure. The chain structure can be linear or branched. Specific examples of polyols with a chain structure having 3 to 6 carbon atoms include glycerol, diglycerol, pentaerythritol, sorbitol, trimethylolethane, trimethylolpropane, glycerol, pentanetriol, and hexanetriol.

[0066] As a monobasic fatty acid with 8 or more but less than 24 carbon atoms, it can be any known substance and can be either a saturated or unsaturated fatty acid. Furthermore, it can be linear or branched. Specific examples of the aforementioned saturated fatty acids include caprylic acid (caprylic acid), nonanoic acid, capric acid (capric acid), lauryl acid (lauric acid), myristic acid (tetradecanoic acid), palmitic acid (palmitic acid), stearic acid (stearic acid), eicosanoic acid (arachidic acid), behenic acid (behenic acid), and tetracosanoic acid. Specific examples of the aforementioned unsaturated fatty acids include myristoleic acid, palmitoleic acid, oleic acid, isoleic acid, eicosenoic acid, linoleic acid, alpha-linolenic acid, gamma-linolenic acid, and arachidonic acid.

[0067] As a monohydric alcohol with 8 or more but less than 24 carbon atoms, a known substance may be used, and it may be a saturated aliphatic monohydric alcohol or an unsaturated aliphatic monohydric alcohol. In addition, it may be a straight-chain monohydric alcohol or a monohydric alcohol with a branched structure. Specific examples of monohydric alcohols with 8 or more carbon atoms but less than 24 include straight-chain alkyl alcohols such as octanol, nonanol, decanol, undecaneol, dodecaneol, tridecaneol, tetradecaneol, pentadecaneol, hexadecaneol, heptadecanol, octadecaneol, nonadecanol, eicosaneol, dodecaneol, tridecaneol, and tetradecaneol; branched-chain alkyl alcohols such as isooctanol, isononanol, isodecanol, isododecaneol, isotridecaneol, isotetradecaneol, isopentadecanol, isohexadecanol, isooctadecaneol, isononadecanol, isoeicosaneol, isoeicosaneol, isotridecaneol, and isoecosaneol; and straight-chain alkenyl alcohols such as tetradecenol, hexadecenol, heptadecanol, octadecenol, and nonadecanenol.

[0068] As a polyfatty acid with 3 or more but less than 10 carbon atoms, it can be any known substance, including saturated fatty acids, unsaturated fatty acids, and aromatic carboxylic acids. Specific examples of polyfatty acids with 3 or more but less than 10 carbon atoms include aliphatic carboxylic acids such as malonic acid, succinic acid, glutaric acid, adipic acid, fumaric acid, maleic acid, and aconitic acid, as well as aromatic carboxylic acids such as terephthalic acid, isophthalic acid, and trimellitic acid.

[0069] Specific examples of complete ester compounds (A1) include trimethylolpropane trioleate, diisostearyl adipate, and natural oils such as coconut oil, rapeseed oil, sunflower oil, soybean oil, castor oil, sesame oil, palm oil, fish oil, and tallow.

[0070] Specific examples of sulfur-containing ester compounds (A2) include dioctyl thiodipropionate, diisolauryl thiodipropionate, dilauryl thiodipropionate, diisohexadecyl thiodipropionate, diisostearyl thiodipropionate, dioleyl thiodipropionate, octyl thiodipropionate, isolauryl thiodipropionate, lauryl thiodipropionate, isohexadecyl thiodipropionate, isostearyl thiodipropionate, oleyl thiodipropionate, octyl mercaptopropionate, stearyl mercaptopropionate, trimethylolpropane tris(mercaptopropionate), dioctyl dithiodipropionate, etc.

[0071] Specific examples of ester compounds (A3) include trimethylolpropane monooleate, glyceryl monooleate, diglyceryl dilaurate, trimethylolpropane dioleate, and glyceryl dioleate.

[0072] The lower limit of the content ratio of the complete ester compound (A1) in the treatment agent can be suitably selected, preferably 30% by mass or more, more preferably 35% by mass or more. The upper limit of this content ratio can be suitably selected, preferably 70% by mass or less, more preferably 65% ​​by mass or less. A range formed by any combination of the above upper and lower limits can also be set. By limiting it to this range, the effect of the present invention can be further improved.

[0073] The ratio of complete ester compound (A1) and sulfur-containing ester compound (A2) in the treatment agent, by mass ratio, is preferably 1 / 1 or more and 100 / 1 or less. By limiting it to this range, tension fluctuations can be suppressed.

[0074] The ratio of complete ester compound (A1) and partial ester compound (A3) in the treatment agent, by mass ratio, is preferably 1 / 1 or more and 10,000 / 1 or less. By limiting it to this range, the accumulation of tar can be suppressed.

[0075] Other ester oils besides those mentioned above may also be used. Specific examples of such ester oils include: (1) ester compounds of aliphatic monools and aliphatic monocarboxylic acids such as octyl palmitate, oleic acid ester, oleic acid ester, isotriadecyl stearate, and isotetracosyl oleate; and (2) ester compounds of aromatic alcohols and aliphatic carboxylic acids such as benzyl oleate, benzyl laurate, and bisphenol A dilaurate.

[0076] These smoothing agents (A) can be used alone or in combination of two or more suitable smoothing agents.

[0077] (Nonionic surfactant (B))

[0078] Examples of nonionic surfactants (B) include substances formed by adding epoxides to alcohols or carboxylic acids, ether-ester compounds formed by adding epoxides to ester compounds of carboxylic acids and polyols, substances formed by adding epoxides to alkylamines (which are amine compounds), and ester compounds of carboxylic acids and polyols with a cyclic structure having 3 or more but less than 6 carbon atoms. These nonionic surfactants (B) can be used alone, or two or more nonionic surfactants can be suitably combined.

[0079] Specific examples of alcohols used as raw materials for nonionic surfactants (B) include: (1) straight-chain alkyl alcohols such as methanol, ethanol, propanol, butanol, pentanol, hexanol, octanol, nonanol, decanol, undecanol, dodecanol, tridecanol, tetradecanol, pentadecanol, hexadecanol, heptadecanol, octadecanol, nonadecanol, eicosane, dodecanol, dodecanol, tridecanol, tetradecanol, pentadecanol, hexadecanol, heptadecanol, octadecanol, nonadecanol, and triadecanol; (2) isopropanol, isobutanol, isohexanol, 2-ethylhexanol, isononol, isodecanol, isodecanol, isodecanol, isodecanol, isodecanol, and isodecanol. Branched alkyl alcohols such as alcohols, isohexadecanol, isohexadecanol, isohexadecanol, isohexadecanol, isohexadecanol, isohexadecanol, isohexadecanol, isohexadecanol, isohexadecanol, isohexadecanol, isohexadecanol, isohexadecanol, isohexadecanol, isohexadecanol, isohexadecanol, isohexadecanol, isohexadecanol, isohexadecanol, etc.; (3) Straight-chain alkenyl alcohols such as tetradecenol, hexadecenol, heptadecenol, octadecenol, and nonadecenol; (4) Branched alkenyl alcohols such as isohexadecanol and isohexadecanol; (5) Cyclic alkyl alcohols such as cyclopentanol and cyclohexanol; (6) Aromatic alcohols such as phenol, nonylphenol, benzyl alcohol, monostyrene phenol, stilbene phenol, and tristyrene phenol.

[0080] Specific examples of carboxylic acids used as raw materials for nonionic surfactants (B) include: (1) straight-chain alkyl carboxylic acids such as octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, dodecanoic acid, etc.; (2) branched-chain alkyl carboxylic acids such as 2-ethylhexanoic acid, isododecanoic acid, isotridecanoic acid, isotetradecanoic acid, isohexadecanoic acid, etc.; (3) straight-chain alkenyl carboxylic acids such as octadecenoic acid, octadecadienoic acid, octadectrienoic acid, etc.; and (4) aromatic carboxylic acids such as benzoic acid.

[0081] Specific examples of epoxides used as raw materials for nonionic surfactants (B) include ethylene oxide and propylene oxide. The molar addition of the epoxide can be suitably set, preferably 0.1 moles or more and 60 moles or less, more preferably 1 mole or more and 40 moles or less, and even more preferably 2 moles or more and 30 moles or less. A range formed by any combination of the above upper and lower limits can also be set. It should be noted that the molar addition of the epoxide represents the number of moles of epoxide relative to 1 mole of alcohol or carboxylic acid added to the raw material. When using multiple epoxides, they can be block adducts or random adducts.

[0082] Specific examples of polyols used as raw materials for nonionic surfactants (B) include ethylene glycol, propylene glycol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 2-methyl-1,2-propanediol, 1,5-pentanediol, 1,6-hexanediol, 2,5-hexanediol, 2-methyl-2,4-pentanediol, 2,3-dimethyl-2,3-butanediol, glycerol, 2-methyl-2-hydroxymethyl-1,3-propanediol, trimethylolpropane, sorbitan, pentaerythritol, sorbitol, etc.

[0083] Specific examples of alkylamines used as raw materials for nonionic surfactants (B) include methylamine, ethylamine, butylamine, octylamine, laurylamine, octadecylamine, octadecylamine, and cocoylamine.

[0084] Specific examples of nonionic surfactants (B) include: substances obtained by adding 10 moles of ethylene oxide (hereinafter referred to as EO) to 1 mole of oleyl alcohol; substances obtained by adding 10 moles of EO to 1 mole of isotretinoin; substances obtained by randomly adding 10 moles of EO and 10 moles of propylene oxide (hereinafter referred to as PO) to 1 mole of isotretinoin; substances obtained by adding 10 moles of EO to 1 mole of hydrogenated castor oil; and compounds obtained by adding 20 moles of EO to 1 mole of hydrogenated castor oil and then esterifying it with 3 moles of oleate. Compounds obtained by adding 25 moles of EO to 1 mole of hydrogenated castor oil, then crosslinking with adipic acid and terminal esterifying with stearic acid (average molecular weight 5000); sorbitan monooleate, sorbitan trioleate, diester of polyethylene glycol (average molecular weight 600) and oleic acid, diester of polyethylene glycol (average molecular weight 400) and lauric acid, monoester of polyethylene glycol (average molecular weight 600) and oleic acid, substances obtained by adding 3 moles of EO relative to 1 mole of laurylamine; substances obtained by adding 10 moles of EO relative to 1 mole of laurylamine; and so on.

[0085] The content of nonionic surfactant (B) in the treatment agent can be suitably set, preferably 5% by mass or more and 70% by mass or less, more preferably 10% by mass or more and 65% by mass or less, and even more preferably 20% by mass or more and 60% by mass or less. A range formed by any combination of the above upper and lower limits can also be set. By limiting the values ​​within this range, the effects of the present invention can be further improved.

[0086] (Phosphate ester compounds (C1))

[0087] The phosphate compound (C1) comprises at least one selected from the following chemical formula (1) representing phosphate P1, the following chemical formula (2) representing phosphate P2, the following chemical formula (3) representing phosphate P3, and the following chemical formula (4) representing phosphate P4.

[0088] [Chemistry 5]

[0089]

[0090] In chemical formula (1),

[0091] R 1 The residue obtained by removing the hydroxyl group from a substance formed by adding 8 or more but less than 24 carbon atoms to an alkyl group, an alkenyl group, or an epoxy alkane with 2 or more but less than 3 carbon atoms in a total of 1 or more but less than 20 moles of aliphatic alcohols with 8 or more but less than 24 carbon atoms.

[0092] M 1 and M 2 These are, respectively, hydrogen atoms, alkali metals, alkaline earth metals (1 / 2), organic amine salts, ammonium, or phosphonium.

[0093] m is an integer of 2 or 3.

[0094] These phosphate esters P1 may contain only one type of phosphate ester P1, or they may contain two or more types of phosphate ester P1.

[0095] As a component of R 1 The alkyl group can be a straight-chain alkyl group or an alkyl group with a branched structure. As a constituent of R 1 The alkenyl group can be a straight-chain alkenyl group or an alkenyl group with a branched structure.

[0096] As a component of R 1 Specific examples of straight-chain alkyl groups include, for example, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, eicosyl, dodecyl, tridecyl, tetradecyl, etc.

[0097] As a component of R 1 Specific examples of alkyl groups with branched structures include isooctyl, isononyl, isodecyl, isoundecyl, isoundecyl, isotridecyl, isotetradecyl, isopentadecanyl, isohexadecyl, isoheptadecyl, isooctadecyl, isoeicosyl, isoicosyldidecyl, isotridecyl, isotetradecyl, etc.

[0098] As a component of R 1 Specific examples of straight-chain alkenyl groups include octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, icosyl, icosyl, tridecenyl, and tetradecenyl.

[0099] As a component of R 1 Specific examples of alkenyl groups with branched structures include isooctenyl, isononenyl, isodelenyl, isodecenyl, isoundecenyl, isododecenyl, isotridecenyl, isotetradecenyl, isopentadecanenyl, isohexadecenyl, isoheptadecenyl, isooctadecenyl, isoeicosenoenyl, isododecenyl, isodotadecanenyl, and isodotadecanenyl.

[0100] As a specific example of an aliphatic alcohol with 8 or more carbon atoms and 24 or less residue obtained by removing hydroxyl groups from a substance formed by adding 1 or more moles of aliphatic alcohols with 8 or more and 24 or less carbon atoms to an epoxide with 2 or more and 3 or less carbon atoms relative to 1 mole, aliphatic monohydric alcohols that are used as raw materials for the above-mentioned ester oil can be cited.

[0101] Specific examples of epoxides include ethylene oxide and propylene oxide. It should be noted that the molar number of epoxides added represents the number of moles of epoxide relative to 1 mole of aliphatic alcohol in the feedstock. When using two or more epoxides, they can be either block adducts or random adducts.

[0102] As a component of R 1Specific examples of residues obtained by removing hydroxyl groups from a substance formed by adding 1 mole or more but less than 20 moles of an epoxide with 2 or more but less than 3 carbon atoms relative to 1 mole of an aliphatic alcohol having 8 or more but less than 24 carbon atoms can be cited as follows: a substance obtained by adding 2 moles of EO to 2-ethylhexanol; a substance obtained by randomly adding 2 moles of EO and 2 moles of PO to n-octanol; a substance obtained by adding 3 moles of EO to lauryl alcohol; a substance obtained by adding 3 moles of E to isolarin. The substance obtained by adding 3 moles of EO and 3 moles of PO to isolaric acid by random addition; the substance obtained by adding 3 moles of EO to cetyl alcohol; the substance obtained by adding 3 moles of EO to isocetyl alcohol; the substance obtained by adding 4 moles of EO to oleyl alcohol; the substance obtained by adding 4 moles of EO to isostearyl alcohol; the substance obtained by adding 3 moles of EO to oleyl alcohol; the substance obtained by random addition of 4 moles of EO and 4 moles of PO to oleyl alcohol; the substance obtained by adding 5 moles of EO to isotetradecenol; and so on.

[0103] M 1 and M 2 These represent hydrogen atoms, alkali metals, alkaline earth metals (1 / 2), organic amine salts, ammonium, or phosphonium, respectively. It should be noted that since alkaline earth metals are divalent, "alkaline earth metal (1 / 2)" indicates that in M... 1 Or M 2 The addition of 1 / 2 mole. Specific examples of alkali metals include sodium, potassium, and lithium. Specific examples of alkaline earth metals include magnesium and calcium.

[0104] Specific examples of organic amines include: (1) aliphatic amines such as methylamine, dimethylamine, trimethylamine, ethylamine, diethylamine, triethylamine, N-N-diisopropylethylamine, butylamine, dibutylamine, 2-methylbutylamine, tributylamine, octylamine, laurylamine, and dimethyllaurylamine; (2) aromatic amines or heterocyclic amines such as aniline, N-methylbenzylamine, pyridine, morpholine, piperazine, and their derivatives; (3) alkanolamines such as monoethanolamine, N-methylethanolamine, diethanolamine, triethanolamine, isopropanolamine, diisopropanolamine, triisopropanolamine, dibutylethanolamine, butyl diethanolamine, octyl diethanolamine, and lauryl diethanolamine; (4) arylamines such as 3-aminopropene; and (5) polyoxyethylene lauryl amino ethers such as polyoxyethylene stearyl amino ether.

[0105] Specific examples of phosphorus include tetramethylphosphonium, tetraethylphosphonium, tetrabutylphosphonium, tetraoctylphosphonium, dibutyldihexylphosphonium, trihexyltetradecylphosphonium, triethyloctylphosphonium, triphenylmethylphosphonium, and other quaternary phosphorus.

[0106] Phosphate P2 is represented by the following chemical formula (2).

[0107] [Chemistry 6]

[0108]

[0109] In chemical formula (2),

[0110] R 2 and R 3 The residues obtained by removing hydroxyl groups from substances formed by adding alkyl groups with 8 or more and 24 or fewer carbon atoms, alkenyl groups with 8 or more and 24 or fewer carbon atoms, or epoxides with 2 or more and 3 or fewer carbon atoms in a total of 1 or more and 20 moles of aliphatic alcohols with 8 or more and 24 or fewer carbon atoms.

[0111] M 3 It can be hydrogen atom, alkali metal, alkaline earth metal (1 / 2), organic amine salt, ammonium, or phosphonium.

[0112] n is an integer of 2 or 3.

[0113] Regarding these phosphate esters P2, one phosphate ester P2 can be used alone, or two or more phosphate esters P2 can be used in a suitable combination.

[0114] As a component of R 2 Or R 3 The alkyl group can be a straight-chain alkyl group or an alkyl group with a branched structure. As a constituent of R 2 Or R 3 The alkenyl group can be a straight-chain alkenyl group or an alkenyl group with a branched structure.

[0115] As a component of R 2 Or R 3 Specific examples of alkyl groups can be given by R as a constituent of chemical formula (1). 1 The alkyl group is exemplified. As a constituent of R 2 Or R 3 Specific examples of alkenyl groups can be given by R as a constituent of chemical formula (1). 1 Examples are given by the alkenyl group.

[0116] As a component of R 2 Or R 3 A specific example of a residue obtained by removing a hydroxyl group from a substance formed by adding 1 mole or more but 20 moles of an epoxide having 2 or more but 3 fewer carbon atoms relative to 1 mole of an aliphatic alcohol having 8 or more but 24 fewer carbon atoms can be found in R of chemical formula (1). 1 The specific examples listed are as follows.

[0117] As M 3A specific example can be given by M in chemical formula (1). 1 Or M 2 Example shown in .

[0118] Phosphate P3 is represented by the following chemical formula (3).

[0119] [Chemistry 7]

[0120]

[0121] In chemical formula (3),

[0122] R 4 A residue obtained by removing a hydroxyl group from a substance formed by adding 8 or more but less than 24 carbon atoms to an alkyl group, or an alkenyl group, or an epoxy group with 2 or more but less than 3 carbon atoms in a total of 1 or more but less than 20 moles of aliphatic alcohols with 8 or more but less than 24 carbon atoms.

[0123] M 4 and M 5 These are hydrogen atoms, alkali metals, alkaline earth metals (1 / 2), organic amine salts, ammonium, or phosphorus.

[0124] Regarding these phosphate esters P3, one phosphate ester P3 can be used alone, or two or more phosphate esters P3 can be used in a suitable combination.

[0125] As a component of R 4 The alkyl group can be a straight-chain alkyl group or an alkyl group with a branched structure. As a constituent of R 4 The alkenyl group can be a straight-chain alkenyl group or an alkenyl group with a branched structure.

[0126] As a component of R 4 Specific examples of alkyl groups can be given by R as a constituent of chemical formula (1). 1 The alkyl group is exemplified. As a constituent of R 4 Specific examples of alkenyl groups can be given by R as a constituent of chemical formula (1). 1 The alkenyl group is an example of the group.

[0127] As a component of R 4 A specific example of a residue obtained by removing a hydroxyl group from a substance formed by adding 1 mole or more but 20 moles of an epoxide having 2 or more but 3 fewer carbon atoms relative to 1 mole of an aliphatic alcohol having 8 or more but 24 fewer carbon atoms can be found in R of chemical formula (1). 1 The specific examples listed are as follows.

[0128] As M 4 Or M 5A specific example can be given by M of chemical formula (1). 1 Or M 2 Example shown in .

[0129] Phosphate P4 is represented by the following chemical formula (4).

[0130] [Chemistry 8]

[0131]

[0132] In chemical formula (4),

[0133] R 5 and R 6 The residues obtained by removing hydroxyl groups from substances formed by adding alkyl groups with 8 or more and 24 or fewer carbon atoms, alkenyl groups with 8 or more and 24 or fewer carbon atoms, or epoxides with 2 or more and 3 or fewer carbon atoms in a total of 1 or more and 20 moles of aliphatic alcohols with 8 or more and 24 or fewer carbon atoms.

[0134] M 6 It can be hydrogen atom, alkali metal, alkaline earth metal (1 / 2), organic amine salt, ammonium, or phosphorus.

[0135] Regarding these phosphate esters P4, one phosphate ester P4 can be used alone, or two or more phosphate esters P4 can be used in a suitable combination.

[0136] As a component of R 5 Or R 6 The alkyl group can be a straight-chain alkyl group or an alkyl group with a branched structure. As a constituent of R 5 Or R 6 The alkenyl group can be a straight-chain alkenyl group or an alkenyl group with a branched structure.

[0137] As a component of R 5 Or R 6 Specific examples of alkyl groups can be given by R as a constituent of chemical formula (1). 1 The alkyl group is exemplified. As a constituent of R 5 Or R 6 Specific examples of alkenyl groups can be given by R as a constituent of chemical formula (1). 1 The alkenyl group is an example of the group.

[0138] As a component of R 5 Or R 6 A specific example of a residue obtained by removing a hydroxyl group from a substance formed by adding 1 mole or more but 20 moles of an epoxide having 2 or more but 3 fewer carbon atoms relative to 1 mole of an aliphatic alcohol having 8 or more but 24 fewer carbon atoms can be found in R of chemical formula (1).1 The specific examples listed are as follows.

[0139] As M 6 A specific example can be given by M in chemical formula (1). 1 Or M 2 Example shown in .

[0140] Phosphate compounds (C1) can be used in the following manner: in the P-nuclear NMR determination after alkaline neutralization pretreatment, when the total P-nuclear NMR integral of the above-mentioned phosphate ester P1, the above-mentioned phosphate ester P2, the above-mentioned phosphate ester P3, and the above-mentioned phosphate ester P4 is set to 100%, the P-nuclear NMR integral of the above-mentioned phosphate ester P1 is 7% or less.

[0141] The aforementioned "base over-neutralization pretreatment" refers to the pretreatment of alkyl phosphate compounds by adding an excess of base. It should be noted that there is no particular limitation on the specific examples of the base; for example, organic amines, alkali metals, or alkaline earth metal hydroxides can be mentioned. Furthermore, the base used in the synthesis of the phosphate salt can be the same as or different from that used in the synthesis. Specific examples of organic amines include substances listed among the organic amines that constitute the phosphate salts described above. Specific examples of alkali metal or alkaline earth metal hydroxides include, for example, sodium hydroxide, potassium hydroxide, and magnesium hydroxide.

[0142] exist 31 In the P-NMR determination, by performing this "alkaline over-neutralization pretreatment", the peaks belonging to phosphate esters P1 to P4 can be clearly separated, and the P-nucleus integral ratio belonging to each compound can be calculated using the following mathematical formulas (1) to (4). Furthermore, in the examples section described later... 31 In the P-NMR determination, an alkaline overneutralization treatment was performed by adding a base to the phosphate ester compound to the extent that the observed peaks were separated.

[0143] The P-nuclear NMR integral ratio belonging to the aforementioned phosphate ester P1 is represented by the following mathematical formula (1). The P-nuclear NMR integral ratio belonging to the aforementioned phosphate ester P2 is represented by the following mathematical formula (2). The P-nuclear NMR integral ratio belonging to the aforementioned phosphate ester P3 is represented by the following mathematical formula (3). The P-nuclear NMR integral ratio belonging to the aforementioned phosphate ester P4 is represented by the following mathematical formula (4).

[0144] [Number 1]

[0145] P1_P%={P1_P / (P1_P+P2_P+P3_P+P4_P)}×100 (1)

[0146] In mathematical expression (1),

[0147] P1_P% represents the proportion of P-nucleus NMR integrals attributable to phosphate ester P1.

[0148] P1_P represents the P-nucleus NMR integral value attributed to phosphate ester P1.

[0149] P2_P represents the P-nucleus NMR integral value attributed to phosphate ester P2.

[0150] P3_P represents the P-nucleus NMR integral value attributed to phosphate ester P3.

[0151] P4_P represents the P-nucleus NMR integral value attributed to phosphate ester P4.

[0152] [Number 2]

[0153] P2_P%={P2_P / (P1_P+P2_P+P3_P+P4_P)}×100 (2)

[0154] In mathematical expression (2),

[0155] P2_P% represents the proportion of P-nucleus NMR integrals attributable to phosphate ester P2.

[0156] P1_P represents the P-nucleus NMR integral value attributed to phosphate ester P1.

[0157] P2_P represents the P-nucleus NMR integral value attributed to phosphate ester P2.

[0158] P3_P represents the P-nucleus NMR integral value attributed to phosphate ester P3.

[0159] P4_P represents the P-nucleus NMR integral value attributed to phosphate ester P4.

[0160] [Number 3]

[0161] P3_P%={P3_P / (P1_P+P2_P+P3_P+P4_P)}×100 (3)

[0162] In mathematical expression (3),

[0163] P3_P% represents the proportion of P-nucleus NMR integrals attributable to phosphate ester P3.

[0164] P1_P represents the P-nucleus NMR integral value attributed to phosphate ester P1.

[0165] P2_P represents the P-nucleus NMR integral value attributed to phosphate ester P2.

[0166] P3_P represents the P-nucleus NMR integral value attributed to phosphate ester P3.

[0167] P4_P represents the P-nucleus NMR integral value attributed to phosphate ester P4.

[0168] [Number 4]

[0169] P4_P%={P4_P / (P1_P+P2_P+P3_P+P4_P)}×100 (4)

[0170] In mathematical expression (4),

[0171] P4_P% represents the proportion of P-nucleus NMR integrals attributable to phosphate ester P4.

[0172] P1_P represents the P-nucleus NMR integral value attributed to phosphate ester P1.

[0173] P2_P represents the P-nucleus NMR integral value attributed to phosphate ester P2.

[0174] P3_P represents the P-nucleus NMR integral value attributed to phosphate ester P3.

[0175] P4_P represents the P-nucleus NMR integral value attributed to phosphate ester P4.

[0176] When the phosphate compound (C1) includes the aforementioned phosphate ester P2, and the total percentage of the P-nuclear NMR integrals attributable to the aforementioned phosphate ester P1, phosphate ester P2, phosphate ester P3, and phosphate ester P4 is set to 100%, the percentage of the P-nuclear NMR integral attributable to the aforementioned phosphate ester P2 is preferably 5% or more and 50% or less. By limiting it to this range, the effects of the present invention can be further improved.

[0177] When the phosphate compound (C1) includes the aforementioned phosphate ester P2, and the total percentage of the P-nuclear NMR integrals belonging to the aforementioned phosphate esters P1, P2, P3, and P4 is set to 100%, it is preferable that the percentage of the P-nuclear NMR integral belonging to the aforementioned phosphate ester P1 is 5% or less, and the percentage of the P-nuclear NMR integral belonging to the aforementioned phosphate ester P2 is 10% or more and 45% or less. By limiting the range to this range, the effects of the present invention can be further improved.

[0178] When the phosphate compound (C1) includes the aforementioned phosphate ester P2, and the total percentage of the P-core NMR integrals belonging to the aforementioned phosphate esters P1, P2, P3, and P4 is set to 100%, it is more preferable that the percentage of the P-core NMR integral belonging to the aforementioned phosphate ester P1 is 5% or less, and the percentage of the P-core NMR integral belonging to the aforementioned phosphate ester P2 is 15% or more and 40% or less. By limiting this range, tension variation can be further reduced. It should be noted that a range formed by arbitrarily combining the aforementioned upper and lower limits can also be set.

[0179] Phosphate compounds (C1) are obtained by reacting, for example, phosphorus pentoxide with a saturated or unsaturated aliphatic alcohol having 8 or more but less than 24 carbon atoms as a starting alcohol to obtain alkyl phosphates. The alkyl phosphates are then neutralized or over-neutralized using bases such as potassium hydroxide or amines, as needed. In the above-described synthetic method, the phosphate compound is typically a mixture of phosphate P1 (represented by chemical formula (1), phosphate P2 (represented by chemical formula (2), phosphate P3 (represented by chemical formula (3), and phosphate P4 (represented by chemical formula (4)). Among these mixtures, phosphate P1 is particularly prone to decomposition during storage, readily generating inorganic phosphates and their salts. This is especially pronounced when the treatment agent contains water. The precipitation of inorganic phosphates and their salts from the treatment agent reduces its heat resistance, thus adversely affecting ribbon production. To ensure that the NMR integral of the P-core belonging to the aforementioned phosphate ester P1 is 7% or less, it is preferable to avoid contact with moisture by dehydrating the raw material before the phosphorylation process or by using an inert gas atmosphere during the phosphorylation process. It is particularly preferable to avoid using hygroscopic phosphorus pentoxide. Regarding the aforementioned phosphate ester P1, its content can be reduced by adding water to the phosphate ester compound (C1) and heating it to approximately 100°C to decompose it. In this case, inorganic phosphate and its salts are generated by the thermal decomposition of phosphate ester P1. From the perspective of improving heat resistance, it is preferable to remove the inorganic phosphate and its salts from the treatment agent. Their removal can be achieved using known purification techniques, such as adsorption treatment. Furthermore, the phosphate ester compound (C1) can be prepared by mixing phosphate ester P1 represented by chemical formula (1), phosphate ester P2 represented by chemical formula (2), phosphate ester P3 represented by chemical formula (3), and phosphate ester P4 represented by chemical formula (4).

[0180] The content of the phosphate ester compound (C1) in the treatment agent can be suitably set, preferably 0.1% by mass or more and 10% by mass or less, more preferably 0.3% by mass or more and 5% by mass or less, without the formation of a salt using a neutralizing agent. A range formed by arbitrarily combining the above-mentioned upper and lower limits can also be set. By limiting the value to this range, the effects of the present invention can be further improved. Furthermore, by limiting the value to this range, the functions of the treatment agent, such as antistatic properties, can be effectively utilized.

[0181] (Ionic surfactant (C))

[0182] The treatment agent may contain an ionic surfactant (C) other than a phosphate ester compound (C1). Known substances may be suitably used as the ionic surfactant (C) other than a phosphate ester compound (C1). Examples of ionic surfactants include anionic surfactants, cationic surfactants, and amphoteric surfactants.

[0183] Specific examples of anionic surfactants include: (1) aliphatic or aromatic sulfonates such as lauryl sulfonate, myristyl sulfonate, cetyl sulfonate, oleyl sulfonate, stearyl sulfonate, tetradecane sulfonate, α-olefin sulfonic acid, dodecylbenzene sulfonate, and secondary alkyl sulfonate; (2) sulfates of aliphatic alcohols such as lauryl sulfate, oleyl sulfate, and stearyl sulfate; (3) sulfates of substances formed by the addition of at least one epoxide selected from EO and PO to aliphatic alcohols, such as polyoxyethylene lauryl ether sulfate, polyoxyethylene (polyoxyethylene, polyoxypropylene) lauryl ether sulfate, and polyoxyethylene oleyl ether sulfate; (4) castor oil fatty acid sulfates, Sulfated esters of fatty acids such as sesame fatty acid sulfate, tall oil fatty acid sulfate, soybean oil fatty acid sulfate, rapeseed oil fatty acid sulfate, palm oil fatty acid sulfate, lard fatty acid sulfate, tallow fatty acid sulfate, and whale oil fatty acid sulfate; (5) Sulfated esters of oils such as castor oil sulfate, sesame oil sulfate, tall oil sulfate, soybean oil sulfate, rapeseed oil sulfate, palm oil sulfate, lard sulfate, tallow sulfate, and whale oil sulfate; (6) Fatty acid salts such as laurate, oleate, stearate, and dodecenyl succinate; (7) Sulfonated succinate salts of aliphatic alcohols such as dioctyl sulfonated succinate. Counterions for anionic surfactants include, for example, alkali metal salts such as potassium salts and sodium salts, ammonium salts, and alkylamine salts such as triethanolamine.

[0184] Specific examples of cationic surfactants include lauryltrimethylammonium chloride, hexadecyltrimethylammonium chloride, stearyltrimethylammonium chloride, docosyltrimethylammonium chloride, and dialcyldimethylammonium chloride.

[0185] Specific examples of amphoteric surfactants include betaine-type amphoteric surfactants.

[0186] Regarding these ionic surfactants (C), one ionic surfactant can be used alone, or two or more ionic surfactants can be used in a suitable combination.

[0187] (Alcohol compound (D))

[0188] The alcohol compound (D) further improves the stability of the treatment agent during storage. It also further improves the heat resistance of the treatment agent. Examples of alcohol compounds (D) include monohydric alcohols and polyhydric alcohols. Preferably, alcohol compound (D) contains at least one selected from monohydric alcohols and dihydric alcohols. This compound can suppress the shedding of treatment agent precipitates onto the heating roller and suppress tar accumulation. Examples of monohydric alcohols include lower alcohols and higher alcohols. Furthermore, examples of higher alcohols include monohydric aliphatic alcohols with 8 or more but 24 or fewer carbon atoms.

[0189] As a monohydric alcohol, there are no particular restrictions on the presence or absence of unsaturated bonds; it can be an alcohol with straight-chain or branched hydrocarbon groups, or an alcohol with rings. In the case of an alcohol with branched hydrocarbon groups, there are no particular restrictions on the branching position. Furthermore, it can be a primary alcohol, a secondary alcohol, or a tertiary alcohol. Specific examples of monohydric alcohols include methanol, ethanol, propanol, octyl alcohol, nonanol, decyl alcohol, undecyl alcohol, lauryl alcohol, tridecyl alcohol, myristol, pentadecyl alcohol, cetyl alcohol, stearyl alcohol, eicosyl alcohol, behenyl alcohol, tetracosyl alcohol, oleyl alcohol, isopropanol, 2-ethylhexanol, isododecyl alcohol, isotridecyl alcohol, isomyristyl alcohol, isocetyl alcohol, isostearyl alcohol, isotetracosyl alcohol, etc.

[0190] Specific examples of diols include ethylene glycol, propylene glycol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 2-methyl-1,2-propanediol, 1,5-pentanediol, 1,6-hexanediol, 2,5-hexanediol, 2-methyl-2,4-pentanediol, 2,3-dimethyl-2,3-butanediol, diethylene glycol, polyethylene glycol, dipropylene glycol, polypropylene glycol, and copolymers of polyethylene glycol and polypropylene glycol. Regarding these alcohol compounds (D), a single alcohol compound can be used, or two or more alcohol compounds can be suitably combined. Among these, (poly)epoxides are preferred from the perspective of improving stability.

[0191] The proportion of monohydric alcohol in the treatment agent can be suitably set, preferably 0.0001% by mass or more and 3% by mass or less, more preferably 0.001% by mass or more and 2.5% by mass or less, and even more preferably 0.01% by mass or more and 2% by mass or less. A range formed by any combination of the above upper and lower limits can also be set. By limiting it to this range, stability can be further improved and tar accumulation can be further suppressed.

[0192] The proportion of diol in the treatment agent can be suitably set, preferably 0.001% by mass or more and 5% by mass or less, more preferably 0.01% by mass or more and 4% by mass or less. A range formed by any combination of the above upper and lower limits can also be set. By limiting it to this range, stability can be further improved and tar accumulation can be further suppressed.

[0193] (other)

[0194] In the treatment agent, the concentration of phosphate ions detected by ion chromatography is preferably 200 ppm or less, more preferably 150 ppm or less. By limiting this range, the accumulation of treatment agent or tar on the heating roller can be suppressed.

[0195] <Second Implementation Method>

[0196] Next, a second embodiment embodying the synthetic fiber of the present invention will be described. The synthetic fiber of this embodiment is coated with the treatment agent of the first embodiment. The treatment agent used to coat the synthetic fiber can be a diluted solution obtained by diluting with a diluent, such as a low-viscosity mineral oil solution, an organic solvent solution, or an aqueous solution. According to the treatment agent of the first embodiment, the storage stability of the treatment agent, such as low-viscosity mineral oil diluted with a non-polar solvent, is particularly improved. The synthetic fiber is obtained by coating the synthetic fiber with a diluted solution of the treatment agent, such as an aqueous solution, in processes such as spinning or stretching. The diluted solution coated on the synthetic fiber can be evaporated by a stretching process or a drying process. Regarding the coating of the treatment agent onto the synthetic fiber, there are no particular restrictions on the timing, as long as it is performed during the spinning process. Further effects of the invention can be expected by using manufacturing equipment that allows the material to pass through rollers at temperatures of 150°C or higher, or by using such equipment in stretching or heat treatment processes.

[0197] There are no particular limitations on specific examples of synthetic fibers to which the treatment agent of this embodiment is applied. Examples include: (1) polyester fibers such as polyethylene terephthalate (PET), polyethylene terephthalate, polyethylene terephthalate, polyethylene naphthalate, polylactic acid, and composite fibers containing these polyester resins; (2) polyamide fibers such as nylon 6 and nylon 66; (3) polyacrylic acid fibers such as polyacrylic acid and modified acrylic acid; and (4) polyolefin fibers such as polyethylene and polypropylene. Among these, polyester fibers and polyamide fibers are preferred. In addition, synthetic fibers other than acrylic fibers for carbon fiber manufacturing are preferred.

[0198] There are no particular limitations on the proportion of the treatment agent adhering to the synthetic fiber, but it is preferable to adhere it at a ratio of 0.1% to 3% by mass (excluding solvents such as water) relative to the synthetic fiber. This configuration further enhances the effectiveness of the present invention. Furthermore, there are no particular limitations on the method of adhering the treatment agent; for example, known methods such as roller oiling, guided oiling using a metering pump, impregnation oiling, and spray oiling can be employed.

[0199] The effects and functions of the treatment agent and synthetic fibers in this embodiment will be explained.

[0200] The treatment agent of this embodiment contains a smoothing agent, a nonionic surfactant, an alcohol compound, and a specific phosphate ester compound. This improves the heat resistance and storage stability of the treatment agent. Furthermore, it particularly suppresses the formation of precipitates, sediments, and tar generated during textile spinning, resulting from the decomposition of phosphate ester P1.

[0201] In addition, it can reduce the tension (i.e., frictional variation) caused by friction between the moving yarn and the roller that has been treated with the agent, as well as the generation of tar.

[0202] It should be noted that the above implementation methods can also be modified as follows. The above implementation methods and the following modifications can be combined with each other to implement them within the scope of technical inconsistency.

[0203] • In the treatment agent of the above embodiments, stabilizers, charge control agents, binders, antioxidants, ultraviolet absorbers and other components commonly used in treatment agents may be further mixed in to maintain the quality of the treatment agent, without affecting the effect of the present invention.

[0204] The treatment agent described in the above embodiments may further contain water to a extent that does not impair the effects of the present invention. From the viewpoint of improving the stability of the treatment agent, the water content is preferably greater than 0% by mass and less than 4% by mass.

[0205] Example

[0206] To illustrate the structure and effects of the present invention more specifically, embodiments are given below, but the present invention is not limited to these embodiments. It should be noted that in the following descriptions of embodiments and comparative examples, parts refer to parts by mass, and % refers to percentages by mass.

[0207] Experimental Group 1 (Synthesis of Phosphate Ester Compounds (C1))

[0208] The phosphate ester compounds used in the treatment agents of each embodiment and comparative example were synthesized by the method shown below.

[0209] Synthesis of phosphate ester compounds (P-1)

[0210] Isoceritol, used as the starting alcohol, was a substance dehydrated under reduced pressure at 105°C. Isoceritol was added to a four-necked flask, and phosphorus pentoxide was slowly added under a nitrogen atmosphere. The mixture was stirred at 70±5°C for 3 hours to induce phosphorylation. The phosphate was purified by column chromatography and then mixed with dibutylethanolamine as a neutralizing agent. The mixture was stirred at 50°C for 1 hour to synthesize the phosphate ester compound (P-1). The amount of dibutylethanolamine added was calculated based on the amount of phosphate, its acid value (obtained by titration with 1 mol / L KOH solution at a titration point of approximately pH 11), and the base value of dibutylethanolamine (amount of dibutylethanolamine = amount of phosphate × acid value / base value).

[0211] Phosphate ester compounds (P-2~P-6, rP-1, rP-2)

[0212] Regarding the phosphate ester compounds (P-2 to P-6), the starting alcohols listed in Table 1 were used as the starting materials, and the synthesis was carried out using the same method as for P-1. Furthermore, the phosphorylation reaction of the phosphate ester compounds (rP-1, rP-2) was carried out under atmospheric conditions. Regarding the starting material phosphorus pentoxide, the reagent bottle was opened and placed under atmospheric conditions (room temperature: approximately 27°C, relative humidity: approximately 80%) until the total amount was added (approximately 30 minutes from the start to the end of the addition). The neutralization of the phosphate ester compound (rP-1) was carried out by adding the phosphate to an aqueous potassium hydroxide solution and stirring, allowing it to dry naturally, and then providing it as a treatment agent.

[0213] The alkyl raw material alcohols that constitute the phosphate ester compounds (P-1 to P-6, rP-1, rP-2) mixed in the treatment agent, and the neutralizing agents (bases) used to form the salts are shown in the "Raw Material Alcohols" column and "Neutralizing Agents" column of Table 1, respectively.

[0214] • P-nuclear NMR determination method

[0215] Pretreatment was performed by adding 0.15 g of laurylamine as a base to 0.10 g of each phosphate ester compound (C1) synthesized as described above, followed by stirring. Then, using... 31 P-NMR was used to determine the NMR integral values ​​of each P nucleus belonging to the phosphate esters P1 to P4.

[0216] It should be noted that the P-core NMR integration ratio uses 31The measured values ​​were obtained using P-NMR (mercuryplus NMR Spectrometor System manufactured by VALIAN, 300MHz). It should be noted that deuterated chloroform was used as the solvent. The percentage of each P-core NMR component belonging to phosphate esters P1 to P4 was calculated based on the above mathematical formulas (1) to (4). The values ​​calculated using mathematical formulas (1) to (4) for each phosphate ester compound (C1) were equal to the percentage of the P-core NMR component of the treatment agent containing these phosphate ester compounds (C1).

[0217] The P-nuclear NMR integral percentages (%) of phosphate esters P1 to P4, obtained by P-nuclear NMR determination of phosphate esters, are shown in the "P-nuclear NMR integral percentage (%)" column of Table 1.

[0218] [Table 1]

[0219]

[0220] Experimental Group 2 (Preparation of the Treatment Agent)

[0221] Regarding the treatment agents used in each embodiment and comparative example, they were prepared using the components shown in Tables 2 and 3 by the following preparation methods.

[0222] The following components were thoroughly mixed to obtain a homogeneous mixture, thereby preparing the treatment agent of Example 1: 30 parts (%) of trimethylolpropane trioleate (L-1) as a smoothing agent (A); 30 parts (%) of rapeseed oil (L-3); 2 parts (%) of diisostearyl thiodipropionate (LS-1); 1 part (%) of trimethylolpropane dioleate (pL-1); 5 parts (%) of a substance (N-3) formed by random addition of 10 moles of EO and 10 moles of PO relative to 1 mole of isotretinoin as a nonionic surfactant; 14 parts (%) of a substance (N-4) formed by adding 10 moles of EO relative to 1 mole of hydrogenated castor oil; 14 parts (%) of compound (N-5) formed by adding 20 moles of EO to 1 mole of hydrogenated castor oil and then esterifying it with 3 moles of oleic acid; 1 part (%) of substance (N-12) formed by adding 3 moles of EO to 1 mole of laurylamine; 1.5 parts (%) of phosphate ester compound (P-1) as an ionic surfactant; 1.2 parts (%) of sodium secondary alkyl sulfonate (C=14-17) (S-1); 0.04 parts (%) of isocetyl alcohol (AL-1) as an alcohol compound (D); 0.01 parts (%) of polyethylene glycol (average molecular weight 200) (D-1); and 0.25 parts (%) of ethylene glycol (D-5).

[0223] In Examples 2-18 and Comparative Examples 1-4, the smoothing agent (A), nonionic surfactant (B), ionic surfactant (C), and alcohol compound (D) were mixed in the proportions shown in Tables 2 and 3, as in Example 1, thereby preparing the treatment agent. However, in Examples 3, 4, 5, 6, 7, and 9, in addition to the raw materials in Table 2, 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)isocyanuric acid as an antioxidant was added at a ratio of 0.8 parts relative to 100 parts of the treatment agent.

[0224] In addition, phosphate ions in the treatment agent were determined by ion chromatography under the following conditions. The results are shown in the "Phosphate Ion Concentration" column of Tables 2 and 3.

[0225] Accurately measure 1 g of the sample (including volatile components), and add 10% 2-propanol aqueous solution little by little while stirring to prepare a solution that is diluted to 100 mL in a volumetric flask. Pass 1 mL of the prepared aqueous solution through an ODS (octadecyl group chemically bonded to silica gel) pretreatment kit for ion chromatography analysis. Detection is performed under the following ion chromatography conditions. The detection amount is determined by comparing the peak area ratio with a standard solution of known concentration, and converted to phosphate ions (PO42-). 3- The amount of ).

[0226] <Ion Chromatography Conditions>

[0227] Device: Uses Tosoh IC2001 Suppressor

[0228] Analytical column: TSKgel SuperIC-AZ manufactured by Tosoh Corporation, inner diameter 4.6mm × length 75mm.

[0229] Guard column: TSKgel guardcolumn SuperIC-AZ manufactured by Tosoh Corporation, inner diameter 4.0mm × length 10mm.

[0230] Eluent: 23% volumetric aqueous methanol solution containing 4.8 mmol Na2CO3 and 2.8 mmol NaHCO3, flow rate: 0.6 mL / min.

[0231] In addition, the types and proportions of smoothing agents (A), nonionic surfactants (B), ionic surfactants (C), and alcohol compounds (D) in each example are shown in the "Smoothing Agent (A)", "Nonionic Surfactant (B)", "Ionic Surfactant (C)" and "Alcohol Compound (D)" columns of Tables 2 and 3, respectively.

[0232] In addition, the mass ratio of complete ester compound (A1) to sulfur-containing ester compound (A2) and the mass ratio of complete ester compound (A1) to partial ester compound (A3) in the treatment agents of each example are shown in the "Containing ratio (A1) / (A2)" column and "Containing ratio (A1) / (A3)" column of Table 2 and Table 3, respectively.

[0233] [Table 2]

[0234]

[0235] [Table 3]

[0236]

[0237] The details of the smoothing agents (A), nonionic surfactants (B), ionic surfactants (C), and alcohol compounds (D) listed in Tables 2 and 3 are as follows.

[0238] (Smoothing Agent (A))

[0239] L-1: Trimethylolpropane trioleate

[0240] L-2: Diisostearyl adipate

[0241] L-3: Rapeseed oil

[0242] LS-1: Diisostearylthiodipropionate

[0243] LS-2: Dioleothiodipropionate

[0244] pL-1: Trimethylolpropane dioleate

[0245] pL-2: Diglyceride

[0246] eL-1: Octyl palmitate

[0247] (Nonionic surfactant (B))

[0248] N-1: The substance obtained by adding 10 moles of EO to 1 mole of oleyl alcohol.

[0249] N-2: The substance obtained by adding 10 moles of EO to 1 mole of isotretinoin.

[0250] N-3: The substance obtained by the random addition of 1 mole of isotretinoin to 10 moles of EO and 10 moles of PO.

[0251] N-4: The substance obtained by adding 10 moles of EO to 1 mole of hydrogenated castor oil.

[0252] N-5: A compound formed by adding 20 moles of EO to 1 mole of hydrogenated castor oil, followed by esterification with 3 moles of oleic acid.

[0253] N-6: A compound (average molecular weight 5000) formed by adding 25 moles of EO to 1 mole of hydrogenated castor oil, then crosslinking with adipic acid and terminal esterifying with stearic acid.

[0254] N-7: Sorbitan monooleate

[0255] N-8: Sorbitan trioleate

[0256] N-9: Diester of polyethylene glycol (average molecular weight 600) and oleic acid

[0257] N-10: Diester of polyethylene glycol (average molecular weight 400) and lauric acid

[0258] N-11: Monoester of polyethylene glycol (average molecular weight 600) and oleic acid

[0259] N-12: The substance obtained by adding 3 moles of EO to 1 mole of laurylamine.

[0260] N-13: The substance obtained by adding 10 moles of EO to 1 mole of laurylamine.

[0261] (Ionic surfactant (C))

[0262] S-1: Sodium secondary alkyl sulfonate (C = 14–17)

[0263] S-2: Sodium dioctylsulfonate

[0264] S-3: Potassium dodecylbenzenesulfonate

[0265] S-4: Sodium α-olefin sulfonate

[0266] (Alcohol compound (D))

[0267] AL-1: Isocetyl

[0268] AL-2: Isostearol

[0269] AL-3: oleyl alcohol

[0270] AL-4: Isotetracosanol

[0271] D-1: Polyethylene glycol (average molecular weight 200)

[0272] D-2: Polyethylene glycol (average molecular weight 400)

[0273] D-3: Polypropylene glycol (average molecular weight 400)

[0274] D-4: Polyethylene glycol-propylene glycol (PO1 mol, EO4 mol)

[0275] D-5: Ethylene glycol

[0276] D-6: Propylene glycol

[0277] D-7: Diethylene glycol

[0278] Experimental Group 3 (Evaluation of Treatment Agents and Synthetic Fibers)

[0279] Stability evaluation

[0280] The treatment agent of Example 1 was prepared, as well as a treatment agent prepared by replacing the phosphate ester compound (P-1) in the treatment agent of Example 1 with other phosphate ester compounds (P-2 to 6, rP-1, rP-2) listed in Table 1. It should be noted that the mixing amount of the phosphate compound was adjusted in the same manner as when mixing the phosphate compound (P-1) with the amount of phosphorus contained in the treatment agent. 100g of each compound was placed in a vial. Next, 1g of distilled water was added. The vials were incubated at 70°C for 3 days, and the presence of any new precipitation of particulate matter from the inorganic phosphate source at the bottom of the vial was observed. Stability was determined according to the following criteria. The results are shown in the "Stability" column of Table 1.

[0281] ○ (Pass): No precipitation occurred.

[0282] × (Defective): Precipitation occurred.

[0283] Evaluation of tension variations

[0284] Each treatment agent is uniformly diluted with ion-exchanged water or organic solvent as needed to prepare a 15% solution. The above solution is applied to 1000 dtex, 192 filaments, and 0.93 intrinsic viscosity polyethylene terephthalate fiber (un-oiled filament) using an oiling roller application method at an application amount of 3.0% by mass based on non-volatile components. The diluent is then dried to prepare test yarn.

[0285] Under initial tension of 1.5 kg and a yarn speed of 1.0 m / min, the test yarn was brought into contact with a chrome-plated support bar with a surface temperature of 250 °C and moved. The tension value of the yarn after contact with the chrome-plated support bar was measured. The movement time from the point where the tension value increased by 10% after 20 minutes of movement was recorded, and the results were evaluated according to the following criteria. The results are shown in the "Tension Variation" column of Tables 2 and 3.

[0286] ○○ (Good): More than 6 hours

[0287] ○ (Qualified): 3 hours or more but less than 6 hours

[0288] × (Poor): Less than 3 hours

[0289] • Evaluation of tar

[0290] As an evaluation of the heat resistance of the treatment agent, the tar accumulated on the chrome-plated support after 6 hours in the tension variation test was observed and evaluated according to the following criteria. The results are shown in the "Tar" column of Tables 2 and 3.

[0291] ○○ (Good): Tar was basically not observed.

[0292] ○ (Pass): Slight observation of brown tar was observed.

[0293] × (Poor): Dark brown or black tar was observed.

[0294] As can be seen from the evaluation results of the various embodiments in Tables 1 to 3, the treatment agent according to the present invention has been confirmed to have excellent storage stability, tension variation, and tar reduction.

[0295] The present invention also includes the following methods.

[0296] (Postscript 1)

[0297] A synthetic fiber treatment agent, characterized in that it contains a smoothing agent (A), a nonionic surfactant (B), an ionic surfactant (C) comprising the following phosphate ester compound (C1), and an alcohol compound (D) (excluding an acrylic fiber treatment agent for carbon fiber manufacturing).

[0298] The phosphate compound (C1) comprises phosphate P4 represented by the following chemical formula (4), and optionally further comprises at least one selected from phosphate P1 represented by the following chemical formula (1), phosphate P2 represented by the following chemical formula (2), and phosphate P3 represented by the following chemical formula (3). When the total proportion of the P-nuclear NMR integrals attributable to the above-mentioned phosphate P1, phosphate P2, phosphate P3, and phosphate P4 is set to 100%, the proportion of the P-nuclear NMR integrals attributable to the above-mentioned phosphate P1 is 7% or less.

[0299] [Chemistry 9]

[0300]

[0301] In chemical formula (1),

[0302] R 1 The residue obtained by removing the hydroxyl group from a substance formed by adding 8 or more but less than 24 carbon atoms to an alkyl group, an alkenyl group, or an epoxy alkane with 2 or more but less than 3 carbon atoms in a total of 1 or more but less than 20 moles of aliphatic alcohols with 8 or more but less than 24 carbon atoms.

[0303] M 1and M 2 These are, respectively, hydrogen atoms, alkali metals, alkaline earth metals (1 / 2), organic amine salts, ammonium, or phosphonium.

[0304] m is an integer of 2 or 3.

[0305] [Chemistry 10]

[0306]

[0307] In chemical formula (2),

[0308] R 2 and R 3 The residues obtained by removing hydroxyl groups from substances formed by adding alkyl groups with 8 or more and 24 or fewer carbon atoms, alkenyl groups with 8 or more and 24 or fewer carbon atoms, or epoxides with 2 or more and 3 or fewer carbon atoms in a total of 1 or more and 20 moles of aliphatic alcohols with 8 or more and 24 or fewer carbon atoms relative to 1 mole.

[0309] M 3 It can be hydrogen atom, alkali metal, alkaline earth metal (1 / 2), organic amine salt, ammonium, or phosphonium.

[0310] n is an integer of 2 or 3.

[0311] [Chemistry 11]

[0312]

[0313] In chemical formula (3),

[0314] R 4 The residue obtained by removing the hydroxyl group from a substance formed by adding 8 or more but less than 24 carbon atoms to an alkyl group, an alkenyl group, or an epoxy alkane with 2 or more but less than 3 carbon atoms in a total of 1 or more but less than 20 moles of aliphatic alcohols with 8 or more but less than 24 carbon atoms.

[0315] M 4 and M 5 These are, respectively, hydrogen atoms, alkali metals, alkaline earth metals (1 / 2), organic amine salts, ammonium, or phosphonium.

[0316] [Chemistry 12]

[0317]

[0318] In chemical formula (4),

[0319] R 5 and R 6The residues obtained by removing hydroxyl groups from substances formed by adding alkyl groups with 8 or more and 24 or fewer carbon atoms, alkenyl groups with 8 or more and 24 or fewer carbon atoms, or epoxides with 2 or more and 3 or fewer carbon atoms in a total of 1 or more and 20 moles of aliphatic alcohols with 8 or more and 24 or fewer carbon atoms relative to 1 mole.

[0320] M 6 It can be hydrogen atom, alkali metal, alkaline earth metal (1 / 2), organic amine salt, ammonium, or phosphorus.

[0321] (Postscript 2)

[0322] According to the synthetic fiber treatment agent described in Appendix 1, wherein the phosphate compound (C1) further comprises the phosphate P2, and when the total percentage of the P-nuclear NMR integrals attributable to the phosphate P1, the phosphate P2, the phosphate P3, and the phosphate P4 is set to 100%, the percentage of the P-nuclear NMR integrals attributable to the phosphate P2 is 5% or more and 50% or less.

[0323] (Note 3)

[0324] According to the synthetic fiber treatment agent described in Appendix 1 or 2, wherein the phosphate compound (C1) further comprises the phosphate P2, and when the total P-nuclear NMR integral ratio of the phosphate P1, the phosphate P2, the phosphate P3, and the phosphate P4 is set to 100%, the P-nuclear NMR integral ratio of the phosphate P1 is 5% or less, and the P-nuclear NMR integral ratio of the phosphate P2 is 10% or more and 45% or less.

[0325] (Note 4)

[0326] According to any one of the appendices 1 to 3, the synthetic fiber treatment agent, wherein the alcohol compound (D) comprises at least one selected from monohydric alcohols and dihydric alcohols.

[0327] (Note 5)

[0328] According to Appendix 4, the synthetic fiber treatment agent contains a monohydric alcohol, and the monohydric alcohol content in the synthetic fiber treatment agent is 0.0001% by mass or more and 3% by mass or less.

[0329] (Note 6)

[0330] According to Appendix 4 or 5, the synthetic fiber treatment agent contains a diol, and the diol content in the synthetic fiber treatment agent is 0.001% by mass or more and 5% by mass or less.

[0331] (Note 7)

[0332] According to any one of the appendices 1 to 6, the synthetic fiber treatment agent, wherein,

[0333] The smoothing agent (A) described above comprises at least one selected from the following complete ester compound (A1), sulfur-containing ester compound (A2), and partial ester compound (A3).

[0334] The complete ester compound (A1) is selected from at least one of a complete ester compound of a polyol having a chain structure with 3 or more and 6 or fewer carbon atoms and a monobasic fatty acid having 8 or more and 24 or fewer carbon atoms, and a complete ester compound of a monobasic alcohol having 8 or more and 24 or fewer carbon atoms and a polybasic fatty acid having 3 or more and 10 or fewer carbon atoms.

[0335] Ester compounds (A3) are ester compounds of polyols with a chain structure having 3 or more but less than 6 carbon atoms and monobasic fatty acids having 8 or more but less than 24 carbon atoms.

[0336] (Postscript 8)

[0337] According to Appendix 7, the synthetic fiber treatment agent contains the complete ester compound (A1), and the proportion of the complete ester compound (A1) in the synthetic fiber treatment agent is 30% by mass or more and 70% by mass or less.

[0338] (Note 9)

[0339] According to Appendix 8, the synthetic fiber treatment agent, wherein the smoothing agent (A) comprises the sulfur-containing ester compound (A2).

[0340] (Postscript 10)

[0341] According to the synthetic fiber treatment agent described in Appendix 9, the content ratio of the above-mentioned complete ester compound (A1) and the above-mentioned sulfur-containing ester compound (A2) is, by mass ratio, more than 1 / 1 and less than 100 / 1 of the above-mentioned complete ester compound (A1) / the above-mentioned sulfur-containing ester compound (A2).

[0342] (Postscript 11)

[0343] The synthetic fiber treatment agent according to any one of Appendices 8 to 10, wherein the smoothing agent (A) comprises the aforementioned ester compound (A3).

[0344] (Postscript 12)

[0345] According to the synthetic fiber treatment agent described in Appendix 11, the content ratio of the above-mentioned complete ester compound (A1) and the above-mentioned partial ester compound (A3) is, by mass ratio, more than 1 / 1 and less than 10000 / 1.

[0346] (Postscript 13)

[0347] According to any one of the appendices 1 to 12, the concentration of phosphate ions detected by ion chromatography in the synthetic fiber treatment agent is less than 200 ppm.

[0348] (Postscript 14)

[0349] A synthetic fiber, characterized in that it is coated with a synthetic fiber treatment agent as described in any one of Appendices 1 to 13 (excluding acrylic fibers for carbon fiber manufacturing).

Claims

1. A treatment agent for synthetic fibers, wherein the treatment agent for synthetic fibers does not include acrylic fiber treatment agents for carbon fiber manufacturing, characterized in that, It contains a smoothing agent (A), a nonionic surfactant (B), an ionic surfactant (C) comprising the following phosphate ester compound (C1), and an alcohol compound (D). The phosphate compound (C1) comprises phosphate P4 represented by chemical formula (4) and at least one selected from phosphate P1 represented by chemical formula (1), phosphate P2 represented by chemical formula (2), and phosphate P3 represented by chemical formula (3), wherein when the total percentage of the P-nuclear NMR integrals attributable to phosphate P1, phosphate P2, phosphate P3, and phosphate P4 is set to 100%, the percentage of the P-nuclear NMR integral attributable to phosphate P1 is 7% or less. [Chemistry 1] In chemical formula (1), R 1 The residue obtained by removing the hydroxyl group from a substance formed by adding 8 or more but less than 24 carbon atoms to an alkyl group, an alkenyl group, or an epoxy alkane with 2 or more but less than 3 carbon atoms in a total of 1 or more but less than 20 moles of aliphatic alcohols with 8 or more but less than 24 carbon atoms. M 1 and M 2 These are, respectively, hydrogen atoms, alkali metals, alkaline earth metals (1 / 2), organic amine salts, ammonium, or phosphonium. m is an integer of 2 or 3. [Chemistry 2] In chemical formula (2), R 2 and R 3 The residues obtained by removing hydroxyl groups from substances formed by adding alkyl groups with 8 or more and 24 or fewer carbon atoms, alkenyl groups with 8 or more and 24 or fewer carbon atoms, or epoxides with 2 or more and 3 or fewer carbon atoms in a total of 1 or more and 20 moles of aliphatic alcohols with 8 or more and 24 or fewer carbon atoms relative to 1 mole. M 3 It can be hydrogen atom, alkali metal, alkaline earth metal (1 / 2), organic amine salt, ammonium, or phosphonium. n is an integer of 2 or 3. [Chemistry 3] In chemical formula (3), R 4 The residue obtained by removing the hydroxyl group from a substance formed by adding 8 or more but less than 24 carbon atoms to an alkyl group, an alkenyl group, or an epoxy alkane with 2 or more but less than 3 carbon atoms in a total of 1 or more but less than 20 moles of aliphatic alcohols with 8 or more but less than 24 carbon atoms. M 4 and M 5 These are, respectively, hydrogen atoms, alkali metals, alkaline earth metals (1 / 2), organic amine salts, ammonium, or phosphonium. [Chemistry 4] In chemical formula (4), R 5 and R 6 The residues obtained by removing hydroxyl groups from substances formed by adding alkyl groups with 8 or more and 24 or fewer carbon atoms, alkenyl groups with 8 or more and 24 or fewer carbon atoms, or epoxides with 2 or more and 3 or fewer carbon atoms in a total of 1 or more and 20 moles of aliphatic alcohols with 8 or more and 24 or fewer carbon atoms relative to 1 mole. M 6 It can be hydrogen atom, alkali metal, alkaline earth metal (1 / 2), organic amine salt, ammonium, or phosphorus.

2. The synthetic fiber treatment agent according to claim 1, wherein, The phosphate compound (C1) further comprises the phosphate P2, wherein when the total percentage of the P-nuclear NMR integrals attributable to the phosphate P1, the phosphate P2, the phosphate P3, and the phosphate P4 is set to 100%, the percentage of the P-nuclear NMR integrals attributable to the phosphate P2 is 5% or more and 50% or less.

3. The synthetic fiber treatment agent according to claim 1, wherein, The phosphate compound (C1) further comprises the phosphate P2, wherein when the total percentage of the P-nuclear NMR integrals attributable to the phosphate P1, the phosphate P2, the phosphate P3, and the phosphate P4 is set to 100%, the percentage of the P-nuclear NMR integral attributable to the phosphate P1 is less than 5%, and the percentage of the P-nuclear NMR integral attributable to the phosphate P2 is more than 10% and less than 45%.

4. The synthetic fiber treatment agent according to any one of claims 1 to 3, wherein, The alcohol compound (D) comprises at least one selected from monohydric alcohols and dihydric alcohols.

5. The synthetic fiber treatment agent according to claim 4, wherein, The alcohol compound (D) comprises a monohydric alcohol, and the monohydric alcohol content in the synthetic fiber treatment agent is 0.0001% by mass or more and 3% by mass or less.

6. The synthetic fiber treatment agent according to claim 4, wherein, The alcohol compound (D) comprises a diol, and the diol content in the synthetic fiber treatment agent is 0.001% by mass or more and 5% by mass or less.

7. The synthetic fiber treatment agent according to any one of claims 1 to 3, wherein, The smoothing agent (A) comprises at least one selected from the following complete ester compounds (A1), sulfur-containing ester compounds (A2), and partial ester compounds (A3). The complete ester compound (A1) is selected from at least one of a complete ester compound of a polyol having a chain structure with 3 or more and 6 or fewer carbon atoms and a monobasic fatty acid having 8 or more and 24 or fewer carbon atoms, and a complete ester compound of a monobasic alcohol having 8 or more and 24 or fewer carbon atoms and a polybasic fatty acid having 3 or more and 10 or fewer carbon atoms. Ester compounds (A3) are ester compounds of polyols with a chain structure having 3 or more but less than 6 carbon atoms and monobasic fatty acids having 8 or more but less than 24 carbon atoms.

8. The synthetic fiber treatment agent according to claim 7, wherein, The smoothing agent (A) contains the complete ester compound (A1), and the proportion of the complete ester compound (A1) in the synthetic fiber treatment agent is 30% by mass or more and 70% by mass or less.

9. The synthetic fiber treatment agent according to claim 8, wherein, The smoothing agent (A) comprises the sulfur-containing ester compound (A2).

10. The synthetic fiber treatment agent according to claim 9, wherein, The proportion of the complete ester compound (A1) and the sulfur-containing ester compound (A2) is, by mass ratio, more than 1 / 1 and less than 100 / 1 of the complete ester compound (A1) / the sulfur-containing ester compound (A2).

11. The synthetic fiber treatment agent according to claim 8, wherein, The smoothing agent (A) comprises the ester compound (A3).

12. The synthetic fiber treatment agent according to claim 11, wherein, The proportion of the complete ester compound (A1) and the partial ester compound (A3) is, by mass ratio, more than 1 / 1 and less than 10,000 / 1 of the complete ester compound (A1) / the partial ester compound (A3).

13. The synthetic fiber treatment agent according to any one of claims 1 to 3, wherein, The concentration of phosphate ions detected in the synthetic fiber treatment agent by ion chromatography is below 200 ppm.

14. A synthetic fiber, wherein the synthetic fiber does not include acrylic fiber for carbon fiber manufacturing, characterized in that, It is coated with the synthetic fiber treatment agent as described in any one of claims 1 to 13.

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