Synthetic fiber treatment agent and synthetic fiber

Abstract

Provided are: a synthetic fiber treatment agent that is capable of improving the flexibility of a synthetic fiber to which the synthetic fiber treatment agent is applied, particularly the flexibility of a twisted yarn or a cord using the synthetic fiber, and capable of reducing fluff; and a synthetic fiber. A synthetic fiber treatment agent according to the present invention is characterized by comprising a prescribed tertiary alkanolamine (A), a smoothing agent (B), and an organic phosphoric acid ester compound (C) which is at least one selected from organic phosphoric acid esters and salts thereof, and is characterized in that the mass ratio Ma / Mp of the content Ma of the tertiary alkanolamine (A) to the content Mp of phosphorus detected by ICP optical emission spectrometry is 6 or more.

Description

Treatment agents for synthetic fibers and synthetic fibers

[0001] The present invention relates to a synthetic fiber treatment agent and synthetic fibers having the synthetic fiber treatment agent adhered thereto.

[0002] For example, in the spinning and drawing process, finishing process, etc. of synthetic fibers, a treatment for applying a synthetic fiber treating agent to the surface of the fibers may be carried out from the viewpoint of reducing friction of the fibers, improving antistatic properties, and improving bundling properties.

[0003] For example, synthetic fiber treatment agents disclosed in Patent Documents 1 and 2 are known. The synthetic fiber treatment agent disclosed in Patent Document 1 contains a specific sulfur-containing ester compound (A1) and at least one ester compound (B) selected from the group consisting of an ester compound (B1) that is a condensation product of a polyoxyalkylene group-containing hydroxy fatty acid polyhydric alcohol ester and a dicarboxylic acid or dicarboxylic acid derivative, and an ester compound (B2) in which at least one hydroxyl group of the condensation product is blocked with a fatty acid. Patent Document 2 discloses a diluted solution of a synthetic fiber treatment agent that essentially contains a lubricating agent (L), a nonionic surfactant (N), and a straight-chain hydrocarbon having 11 to 14 carbon atoms (P), and also contains at least one selected from an oil film strengthener (H), an organic sulfonate (AS), an organic phosphate (AP), an ethylene oxide adduct of an organic amine (RA), a low-viscosity diluent (D), and an antioxidant (E).

[0004] International Publication No. WO 2015 / 186545 International Publication No. WO 2022 / 254904

[0005] However, conventional synthetic fiber treatment agents have the problem that the softness of the synthetic fibers to which the agent is applied, particularly the softness of twisted yarns or cords made from synthetic fibers, is poor and fluffing occurs.

[0006] As a result of research aimed at solving the above-mentioned problems, the present inventors have found that a synthetic fiber treatment agent containing a specified tertiary alkanolamine (A), a smoothing agent (B), and a specified organic phosphate ester compound (C) in a specified mass ratio is exactly suitable.

[0007] The following describes various aspects of the treatment agent for synthetic fibers that solve the above problems. Aspect 1 of the treatment agent for synthetic fibers contains a tertiary alkanolamine (A) represented by the following formula (1), a smoothing agent (B), and an organic phosphate ester compound (C) that is at least one selected from organic phosphate esters and salts thereof, and is characterized in that the mass ratio Ma / Mp of the content Ma of the tertiary alkanolamine (A) to the phosphorus content Mp detected by ICP atomic emission spectrometry is 6 or greater.

[0008]

[0009] In formula (1), R １ , R ２ are each a monovalent hydrocarbon group having 1 to 8 carbon atoms, and R ３ is a divalent hydrocarbon group having 1 to 4 carbon atoms. In Aspect 2, in the treating agent for synthetic fibers according to Aspect 1, the smoothing agent (B) contains an ester compound (B1) having a thioether bond in the molecule.

[0010] Aspect 3 is the synthetic fiber treatment agent according to Aspect 1 or 2, wherein the kinematic viscosity of the nonvolatile content of the synthetic fiber treatment agent is 100 mm at 25°C. ２ / s or more 500mm ２ / s or less.

[0011] Aspect 4 is the synthetic fiber treating agent according to any one of Aspects 1 to 3, wherein R １ , R ２ is a monovalent hydrocarbon group having 2 to 4 carbon atoms, and R ３ is a divalent hydrocarbon group having 1 to 4 carbon atoms.

[0012] Aspect 5 is the treatment agent for synthetic fibers according to any one of Aspects 1 to 4, wherein the organic phosphate ester compound (C) is at least one selected from the group consisting of phosphate esters of aliphatic alcohols having from 16 to 24 carbon atoms and salts thereof.

[0013] In a sixth aspect, in the treating agent for synthetic fibers according to the second aspect, the ester compound (B1) is a complete ester of an aliphatic alcohol having from 16 to 24 carbon atoms and thiodipropionic acid.

[0014] In Aspect 7, the synthetic fiber treating agent according to Aspect 2 contains, based on the non-volatile components, the tertiary alkanolamine (A), the smoothing agent (B), the smoothing agent (B1), and the organic phosphate ester compound (C) in proportions of 0.03% by mass to 5% by mass, 20% by mass to 70% by mass, 0.1% by mass to 20% by mass, and 0.1% by mass to 5% by mass, respectively.

[0015] Aspect 8 is the synthetic fiber treating agent according to any one of Aspects 1 to 7, further comprising a nonionic surfactant (D). Aspect 9 is the synthetic fiber treating agent according to Aspect 2, further comprising a nonionic surfactant (D), and the synthetic fiber treating agent contains, based on the nonvolatile content, from 0.03% by mass to 5% by mass of the tertiary alkanolamine (A), from 20% by mass to 70% by mass of the smoothing agent (B), from 0.1% by mass to 20% by mass of the smoothing agent (B1), from 0.1% by mass to 5% by mass of the organic phosphate ester compound (C), and from 20% by mass to 70% by mass of the nonionic surfactant (D).

[0016] In Aspect 10, in the treatment agent for synthetic fibers according to any one of Aspects 1 to 9, the pH of an aqueous solution of the treatment agent for synthetic fibers having a nonvolatile content of 1% by mass at 25° C. is 7.5 or more and 9.0 or less.

[0017] Aspect 11 is a synthetic fiber having adhered thereto the synthetic fiber treatment agent according to any one of Aspects 1 to 10. Aspect 12 is the synthetic fiber according to Aspect 11, wherein the synthetic fiber is a polyester-based synthetic fiber.

[0018] According to the present invention, the softness of synthetic fibers to which a synthetic fiber treating agent has been applied, particularly the softness of twisted yarns or cords made from synthetic fibers, can be improved, and fluffing can be reduced.

[0019] First Embodiment A first embodiment of the synthetic fiber treatment agent (hereinafter simply referred to as the treatment agent) of the present invention will be described below. The treatment agent of this embodiment contains the following tertiary alkanolamine (A), smoothing agent (B), and organic phosphate ester compound (C) which is at least one selected from organic phosphate esters and their salts. The treatment agent may further contain a nonionic surfactant (D).

[0020] (Tertiary alkanolamine (A)) The tertiary alkanolamine (A) used in this embodiment is a tertiary alkanolamine (A) represented by the following formula (1).

[0021]

[0022] In formula (1), R １ , R ２ are each a monovalent hydrocarbon group having 1 to 8 carbon atoms, and R ３ is a divalent hydrocarbon group having 1 to 4 carbon atoms. The hydrocarbon group may be a saturated hydrocarbon group or an unsaturated hydrocarbon group. Furthermore, it may be a straight-chain hydrocarbon group or a branched-chain hydrocarbon group. Examples of the hydrocarbon group include aliphatic hydrocarbon groups.

[0023] The unsaturated hydrocarbon group may be an alkenyl group having one double bond as an unsaturated carbon bond, an alkadienyl group or an alkatrienyl group having two or more double bonds, or an alkynyl group having one triple bond as an unsaturated carbon bond, or an alkadiynyl group having two or more triple bonds.

[0024] R １ , R ２ Examples of the aliphatic hydrocarbon group constituting the formula (I) include an alkyl group, an alkenyl group, etc. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, an isobutyl group, an isopentyl group, an isohexyl group, an isoheptyl group, and an isooctyl group.

[0025] Specific examples of the alkenyl group include a butenyl group, a pentenyl group, a hexenyl group, a heptenyl group, an octenyl group, an isobutenyl group, an isopentenyl group, an isohexenyl group, an isoheptenyl group, and an isooctenyl group.

[0026] R ３ Examples of the aliphatic hydrocarbon group constituting the formula (I) include alkylene groups, etc. Specific examples of the alkylene group include methylene groups, ethylene groups, and trimethylene groups.

[0027] These tertiary alkanolamines (A) may be used singly or in combination of two or more. １ , R ２ is a monovalent hydrocarbon group having 2 to 4 carbon atoms, and R ３ is a divalent hydrocarbon group having from 1 to 4 carbon atoms. By using such a compound, the flexibility of the synthetic fiber to which the treatment agent is applied, particularly the flexibility of a twisted yarn or cord using the synthetic fiber, can be further improved.

[0028] Specific examples of the tertiary alkanolamine (A) include dibutylethanolamine, diethylethanolamine, dimethylethanolamine, and dihexylethanolamine.

[0029] The lower limit of the content of the tertiary alkanolamine (A) in the non-volatile content of the treatment agent can be set as appropriate, but is preferably 0.01% by mass or more, more preferably 0.03% by mass or more. When this content is 0.01% by mass or more, the flexibility of the synthetic fiber to which the treatment agent is applied, particularly the flexibility of a twisted yarn or cord made from the synthetic fiber, can be further improved. The upper limit of the content of the tertiary alkanolamine (A) in the non-volatile content of the treatment agent can be set as appropriate, but is preferably 10% by mass or less, more preferably 5% by mass or less. When this content is 10% by mass or less, the aforementioned effect of improving the flexibility of the synthetic fiber, particularly the flexibility of a twisted yarn or cord made from the synthetic fiber, can be efficiently obtained.

[0030] In one aspect of this embodiment, the content of tertiary alkanolamine (A) in the non-volatile content of the treatment agent is, for example, 0.01% by mass or more, 0.025% by mass or more, 0.03% by mass or more, 0.035% by mass or more, 0.5% by mass or more, or 2% by mass or more. Similarly, the content of tertiary alkanolamine (A) in the non-volatile content of the treatment agent is, for example, 0.01% by mass or less, 0.025% by mass or less, 0.03% by mass or less, 0.035% by mass or less, 0.5% by mass or less, or 2% by mass or less. Note that ranges combining the above upper and lower limits are also contemplated.

[0031] The nonvolatile content is determined from the mass of the bone-dry material obtained by heat-treating the target material at 105°C for 2 hours to thoroughly remove volatile substances (the same applies hereinafter). The lower limit of the mass ratio Ma / Mp of the content Ma of tertiary alkanolamine (A) in the treatment agent to the phosphorus content Mp detected by ICP atomic emission spectrometry (inductively coupled plasma atomic emission spectrometry) is 6 or more, preferably 10 or more, and more preferably 12 or more. By specifying this range, the flexibility of the synthetic fiber to which the treatment agent is applied can be improved, particularly the flexibility of twisted yarns or cords made from the synthetic fibers.

[0032] In one aspect of this embodiment, the mass ratio Ma / Mp is, for example, 7.2 or more, 11.4 or more, 12.8 or more, 14.8 or more, 19.1 or more, 26.8 or more, 36 or more, 38.3 or more, 1441.3 or more, or 1532 or more. Similarly, the mass ratio Ma / Mp is, for example, 7.2 or less, 11.4 or less, 12.8 or less, 14.8 or less, 19.1 or less, 26.8 or less, 36 or less, 38.3 or less, 1441.3 or less, or 1532 or less. Note that ranges combining the above upper and lower limits are also envisioned. In addition, concentration measurement using ICP optical emission spectrometry is performed by first preparing a solution of known phosphorus concentration and subjecting it to an ICP optical emission spectrometer to create a calibration curve, and the concentration can be determined from the detected value of the sample.

[0033] (Lubricant (B)) Examples of the lubricant (B) used in this embodiment include ester compounds, silicone oils, mineral oils, polyolefins, etc. Among these, ester compounds are preferred from the viewpoint of providing excellent flexibility to the synthetic fiber to which the treatment agent is applied, particularly to the twisted yarn or cord using the synthetic fiber.

[0034] (Ester Compound) The ester compound is not particularly limited as long as it can be used as a smoothing agent in the field of processing agents, and examples thereof include ester compounds produced from fatty acids and alcohols. Examples of ester compounds include ester compounds produced from fatty acids having odd or even hydrocarbon groups and alcohols, as described below. The fatty acids used as raw materials for the ester compounds are not particularly limited in terms of the number of carbon atoms, whether or not they are branched, or the valence, and may be, for example, higher fatty acids, fatty acids having a cyclic cyclo ring, or fatty acids having an aromatic ring. The alcohol used as raw material for the ester compounds is not particularly limited in terms of the number of carbon atoms, whether or not they are branched, or the valence, and may be, for example, higher alcohols, alcohols having a cyclic cyclo ring, or alcohols having an aromatic ring.

[0035] The ester compound preferably contains an ester compound (B1) having a thioether bond in the molecule. By containing the ester compound (B1), the flexibility of the synthetic fiber to which the treatment agent is applied, particularly the flexibility of a twisted yarn or cord using the synthetic fiber, can be further improved.

[0036] Specific examples of the ester compound (A1) having a thioether bond in the molecule include dioctyl thiodipropionate, diisolauryl thiodipropionate, dilauryl thiodipropionate, diisopalmityl thiodipropionate (diisocetyl thiodipropionate), diisostearyl thiodipropionate, dioleyl thiodipropionate, diisotetracosyl thiodipropionate, di(2-decyl-1-tetradecanol)thiodipropionate, di(2-dodecyl)thiodipropionate, di(2-octyl-1-decanol) thiodipropionate, di(2-ethylhexyl-1-hexadecanol) thiodipropionate, 2-ethylhexyl (lauryl thiopropionate), octyl thiodipropionate, isolauryl thiodipropionate, lauryl thiodipropionate, isopalmityl thiodipropionate, isostearyl thiodipropionate, monooleyl thiodipropionate, oleyl thiodipropionate, isotetracosyl thiodipropionate, and the like.

[0037] Among the ester compounds (B1), a complete ester of thiodipropionic acid with an aliphatic alcohol having from 16 to 24 carbon atoms is preferred. Such an ester compound can further improve the tar detergency in particular.

[0038] Other ester compounds include (B2) completely esterified compounds of a trivalent or greater and a tetravalent or less polyhydric alcohol with a fatty acid. Specific examples of the trivalent or greater and a tetravalent or less polyhydric alcohol that can be used as a raw material for the completely esterified compound (B2) include glycerin, pentaerythritol, trimethylolpropane, 2-methyl-2-hydroxymethyl-1,3-propanediol, 1,2,3-butanetriol, 1,2,4-butanetriol, erythritol, 1,2,3-pentatriol, and 1,2,4-pentatriol.

[0039] As the fatty acid used as the raw material for the completely esterified compound (B2), any known fatty acid can be appropriately used, and may be a saturated fatty acid or an unsaturated fatty acid. Furthermore, it may be a linear fatty acid or a branched fatty acid. Furthermore, it may be a monovalent fatty acid or a polycarboxylic acid (polybasic acid). Specific examples of fatty acids include, for example, (1) linear alkyl fatty 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, icosanoic acid, henicosanoic acid, docosanoic acid, and tetracosanoic acid; (2) 2-ethylhexanoic acid, isododecanoic acid, isotridecanoic acid, isotetradecanoic acid, and isohexadecanoic acid; (3) straight-chain alkenyl fatty acids such as crotonic acid, myristoleic acid, palmitoleic acid, oleic acid, vaccenic acid, eicosenoic acid, linoleic acid, α-linolenic acid, γ-linolenic acid, and arachidonic acid; and (4) naturally occurring fatty acids such as castor oil fatty acid, sesame oil fatty acid, tall oil fatty acid, soybean oil fatty acid, rapeseed oil fatty acid, palm oil fatty acid, palm kernel fatty acid, and coconut oil fatty acid.

[0040] Specific examples of the completely esterified compound (B2) include glycerin trioleate, trimethylolpropane trilaurate, trimethylolpropane trioleate, pentaerythritol tetraoctate, a triester of trimethylolpropane and a mixed acid (a mixture of palm kernel fatty acid and vegetable oleic acid), a triester of trimethylolpropane and rapeseed oil fatty acid, a triester of trimethylolpropane and coconut oil fatty acid, a tetraester of pentaerythritol and palm oil fatty acid, coconut oil, rapeseed oil, sunflower oil, soybean oil, castor oil, sesame oil, and animal and vegetable oils such as fish oil.

[0041] Specific examples of the ester compounds other than the ester compound (B1) and the completely esterified compound (B2) include, for example, (1) ester compounds of aliphatic monoalcohols and aliphatic monocarboxylic acids, such as butyl stearate, octyl stearate, oleyl laurate, oleyl oleate, isopentacosanyl isostearate, octyl palmitate, oleyl erucinate, and isotridecyl stearate, and ester compounds of aliphatic monocarboxylic acids with (poly)oxyalkylene adducts in which alkylene oxides having from 2 to 4 carbon atoms are added to aliphatic monoalcohols; (2) 1,(3) Complete ester compounds of aliphatic monoalcohols and aliphatic monocarboxylic acids, such as 6-hexanediol didecanoate, (4) (5) (6) (7) (8) (9) (10) (11) (12) (13) (14) (15) (16) (17) (18) (19) (20) (21) (22) (23) (24) (25) (26) (27) (28) (29) (30) (31) (32) (33) (34) (35) (40) Ester compounds of aliphatic polyalcohols and aliphatic monocarboxylic acids, such as 6-hexanediol didecanoate, (35) (46) (47) (58) Ester compounds of aromatic monoalcohols and aliphatic monocarboxylic acids, such as benzyl oleate, benzyl laurate, and polyoxypropylene benzyl stearate, and aromatic monoalcohols. (5) ester compounds of aliphatic monocarboxylic acids with (poly)oxyalkylene adducts in which alkylene oxides having from 2 to 4 carbon atoms are added to an aromatic polyhydric alcohol, such as bisphenol A dilaurate and polyoxyethylene bisphenol A dilaurate; complete ester compounds of aliphatic monocarboxylic acids with (poly)oxyalkylene adducts in which alkylene oxides having from 2 to 4 carbon atoms are added to an aromatic polyhydric alcohol; (6) complete ester compounds of aliphatic monoalcohols with aromatic polycarboxylic acids, such as bis 2-ethylhexyl phthalate, diisostearyl isophthalate and trioctyl trimellitate; and complete ester compounds of aromatic polycarboxylic acids with (poly)oxyalkylene adducts in which alkylene oxides having from 2 to 4 carbon atoms are added to an aliphatic monoalcohol.

[0042] (Other Lubricating Agents (B)) Specific examples of silicone oils include, but are not limited to, dimethyl silicone, phenyl-modified silicone, amino-modified silicone, amide-modified silicone, polyether-modified silicone, aminopolyether-modified silicone, alkyl-modified silicone, alkylaralkyl-modified silicone, alkylpolyether-modified silicone, ester-modified silicone, epoxy-modified silicone, carbinol-modified silicone, mercapto-modified silicone, polyoxyalkylene-modified silicone, and the like.

[0043] Examples of mineral oils include aromatic hydrocarbons, paraffinic hydrocarbons, naphthenic hydrocarbons, etc. More specifically, examples include spindle oil, liquid paraffin, etc. Commercially available products of these mineral oils can be used as appropriate.

[0044] The polyolefin used is a poly-α-olefin used as a smoothing component. Specific examples of polyolefins include poly-α-olefins obtained by polymerizing 1-butene, 1-hexene, 1-decene, etc. Commercially available poly-α-olefins can be used as appropriate.

[0045] These smoothing agents (B) may be used alone or in appropriate combination of two or more. The lower limit of the content of the smoothing agent (B) in the non-volatile content of the treatment agent can be set appropriately, but is preferably 20% by mass or more, more preferably 25% by mass or more. When this content is 20% by mass or more, the smoothness of the synthetic fiber to which the treatment agent is applied can be improved. The upper limit of the content of the smoothing agent (B) in the non-volatile content of the treatment agent can be set appropriately, but is preferably 70% by mass or less, more preferably 65% ​​by mass or less. When this content is 70% by mass or less, the smoothness of the synthetic fiber to which the treatment agent is applied can be efficiently improved.

[0046] In one aspect of this embodiment, the content of the smoothing agent (B) in the non-volatile content of the treatment agent is, for example, 41.5% by mass or more, 45% by mass or more, 48% by mass or more, 48.05% by mass or more, or 55% by mass or more. Similarly, the content of the smoothing agent (B) in the non-volatile content of the treatment agent is, for example, 41.5% by mass or less, 45% by mass or less, 48% by mass or less, 48.05% by mass or less, or 55% by mass or less. Note that ranges combining the above upper and lower limits are also contemplated.

[0047] The lower limit of the content of the ester compound (B1) in the non-volatile content of the treatment agent can be set as appropriate, but is preferably 0.05% by mass or more, more preferably 0.1% by mass or more. When this content is 0.05% by mass or more, the flexibility of the synthetic fiber to which the treatment agent is applied, particularly the flexibility of a twisted yarn or cord using the synthetic fiber, can be further improved. The upper limit of the content of the ester compound (B1) in the non-volatile content of the treatment agent can be set as appropriate, but is preferably 20% by mass or less, more preferably 15% by mass or less. When this content is 20% by mass or less, the flexibility of the synthetic fiber to which the treatment agent is applied, particularly the flexibility of a twisted yarn or cord using the synthetic fiber, can be efficiently further improved.

[0048] In one aspect of this embodiment, the content of the ester compound (B1) in the non-volatile content of the treatment agent is, for example, 0.05% by mass or more, 2% by mass or more, or 5% by mass or more. Similarly, the content of the ester compound (B1) in the non-volatile content of the treatment agent is, for example, 0.05% by mass or less, 2% by mass or less, or 5% by mass or less. Note that ranges obtained by arbitrarily combining the above upper and lower limits are also contemplated.

[0049] (Organophosphate Compound (C)) The treatment agent of this embodiment contains an organophosphate compound (C). By containing the organophosphate compound (C), the treatment agent can reduce fuzz of synthetic fibers to which the treatment agent is applied, particularly fuzz of twisted yarns.

[0050] Examples of the substituent constituting the organic phosphate ester compound (C) include an aliphatic hydrocarbon group, an aromatic hydrocarbon group, etc. Examples of the organic phosphate ester compound (C) include alkyl phosphate esters, alkenyl phosphate esters, aryl phosphate esters, alkyl phosphate esters, alkenyl phosphate esters, or aryl phosphate esters to which a (poly)alkylene oxide chain has been added, and salts thereof, etc. The alkyl group or alkenyl group constituting the alkyl phosphate ester is not particularly limited and may be, for example, linear or branched.

[0051] The aromatic hydrocarbon group is not particularly limited as long as it is a hydrocarbon group having a single ring or a condensed ring as an aromatic ring, and examples thereof include aryl groups such as a phenyl group, a naphthyl group, a tolyl group, a xylyl group, and an alkylphenyl group.

[0052] Examples of alcohols that can be used as raw materials for the organic phosphate ester compound (C) include aliphatic alcohols. Specific examples of aliphatic alcohols include (1) linear alkyl alcohols such as methanol, ethanol, propanol, butanol, pentanol, hexanol, octanol, nonanol, decanol, undecanol, dodecanol, tridecanol, tetradecanol, pentadecanol, hexadecanol, heptadecanol, octadecanol, nonadecanol, eicosanol, heneicosanol, docosanol, tricosanol, tetracosanol, pentacosanol, hexacosanol, heptacosanol, octacosanol, nonacosanol, and triacontanol; and (2) isopropanol, isobutanol, isohexanol, 2-ethylhexanol, isononanol, isodecanol, isododecanol, isotridecanol, and isotetradecanol. (2) branched alkyl alcohols such as isopentadecanol, isohexadecanol, isoheptadecanol, isooctadecanol, isononadecanol, isoeicosanol, isoheneicosanol, isodocosanol, isotricosanol, isotetracosanol, 2-decyltetradecanol, isopentacosanol, isohexacosanol, isoheptacosanol, isooctacosanol, isononacosanol, and isotriacontanol; (3) linear alkenyl alcohols such as tetradecenol, hexadecenol, heptadecenol, octadecenol, oleyl alcohol, and nonadecenol; (4) branched alkenyl alcohols such as isohexadecenol and isooctadecenol; and (5) cyclic alkyl alcohols such as cyclopentanol and cyclohexanol.

[0053] The alkylene oxide used as a raw material for forming the (poly)oxyalkylene structure is preferably an alkylene oxide having 2 to 4 carbon atoms. Specific examples of alkylene oxide include ethylene oxide, propylene oxide, and butylene oxide. The number of moles of alkylene oxide added is set appropriately, but is preferably 0.1 to 60 moles, more preferably 1 to 40 moles, and even more preferably 2 to 30 moles. Ranges combining the above upper and lower limits are also contemplated. The number of moles of alkylene oxide added indicates the number of moles of alkylene oxide per mole of the compound to be added in the charged raw material. As the alkylene oxide, one type of alkylene oxide may be used alone, or two or more types of alkylene oxides may be used in appropriate combination. When two or more types of alkylene oxide are used, the addition form may be any of block addition, random addition, and a combination of block addition and random addition, and is not particularly limited.

[0054] The phosphoric acid constituting the organic phosphate ester compound (C) is not particularly limited and may be orthophosphoric acid or a polyphosphoric acid such as diphosphoric acid. When an organic phosphate ester salt is used as the organic phosphate ester compound (C), examples of the salt include a phosphate ester amine salt and a phosphate ester metal salt.

[0055] Examples of metal salts include alkali metal salts and alkaline earth metal salts. Specific examples of alkali metals constituting alkali metal salts include sodium, potassium, and lithium. Examples of alkaline earth metals constituting alkaline earth metal salts include metals belonging to Group 2 elements, such as calcium, magnesium, beryllium, strontium, and barium.

[0056] The amine constituting the amine salt may be any of a primary amine, a secondary amine, and a tertiary amine. Specific examples of amines constituting the amine salt include: (1) aliphatic amines such as methylamine, dimethylamine, trimethylamine, ethylamine, diethylamine, triethylamine, N-N-diisopropylethylamine, butylamine, dibutylamine, 2-methylbutylamine, tributylamine, octylamine, and dimethyllaurylamine; (2) aromatic amines or heterocyclic amines such as aniline, N-methylbenzylamine, pyridine, morpholine, piperazine, and derivatives thereof; (3) alkanolamines such as monoethanolamine, N-methylethanolamine, diethanolamine, triethanolamine, isopropanolamine, diisopropanolamine, triisopropanolamine, diethylethanolamine, dibutylethanolamine, butyldiethanolamine, octyldiethanolamine, and lauryldiethanolamine; (4) arylamines such as N-methylbenzylamine; (5) polyoxyalkylene alkylamino ethers such as polyoxyethylene laurylamino ether and polyoxyethylene sterylamino ether; and (6) ammonia.

[0057] These organic phosphate ester compounds (C) may be used singly or in appropriate combination of two or more. Among these organic phosphate ester compounds (C), at least one selected from phosphate esters of aliphatic alcohols having from 16 to 24 carbon atoms and salts thereof is preferred. By using such a compound, it is possible to further reduce the fuzz of synthetic fibers to which the treatment agent is applied, particularly the fuzz of twisted yarns.

[0058] Specific examples of the organic phosphate ester compound (C) include, for example, oleyl phosphate or a salt thereof, isocetyl phosphate or a salt thereof, lauryl phosphate or a salt thereof, an alkylene oxide adduct of oleyl alcohol or a salt thereof, and isocetyl phosphate or a salt thereof.

[0059] The lower limit of the content of the organic phosphate ester compound (C) in the non-volatile content of the treatment agent can be set as appropriate, but is preferably 0.01% by mass or more, more preferably 0.1% by mass or more. When this content is 0.01% by mass or more, the fuzz of the synthetic fiber to which the treatment agent is applied, particularly the fuzz of twisted yarns, can be further reduced. The upper limit of the content of the organic phosphate ester compound (C) in the non-volatile content of the treatment agent can be set as appropriate, but is preferably 10% by mass or less, more preferably 5% by mass or less. When this content is 10% by mass or less, the fuzz of the synthetic fiber to which the treatment agent is applied, particularly the fuzz of twisted yarns, can be efficiently reduced.

[0060] In one aspect of this embodiment, the content of the organic phosphate ester compound (C) in the non-volatile content of the treatment agent is, for example, 0.05% by mass or more, 0.095% by mass or more, 1.5% by mass or more, or 2% by mass or more. Similarly, the content of the organic phosphate ester compound (C) in the non-volatile content of the treatment agent is, for example, 0.05% by mass or less, 0.095% by mass or less, 1.5% by mass or less, or 2% by mass or less. Note that ranges combining the above upper and lower limits are also contemplated.

[0061] The nonvolatile content of the treatment agent preferably contains 0.03% by mass or more and 5% by mass or less of tertiary alkanolamine (A), 20% by mass or more and 70% by mass or less of smoothing agent (B), 0.1% by mass or more and 20% by mass or less of smoothing agent (B1), and 0.1% by mass or more and 5% by mass or less of organic phosphate ester compound (C). By specifying these ranges, the effects of the present invention can be further improved. It should be noted that ranges obtained by arbitrarily combining the above upper and lower limits are also contemplated.

[0062] (Nonionic Surfactant (D)) The treatment agent of this embodiment may further contain a nonionic surfactant (D) from the viewpoint of improving the formulation stability.

[0063] Examples of the nonionic surfactant (D) include compounds having a (poly)oxyalkylene structure in which alkylene oxide is added to alcohols or carboxylic acids, ether / ester compounds having a (poly)oxyalkylene structure in which alkylene oxide is added to an ester compound of carboxylic acids and polyhydric alcohol, compounds obtained by esterifying an ether / ester compound having a (poly)oxyalkylene structure in which alkylene oxide is added to an ester compound of carboxylic acids and polyhydric alcohol with a carboxylic acid, and (poly)oxy in which alkylene oxide is added to an ester compound of carboxylic acids and polyhydric alcohol. Examples of suitable amine compounds include compounds in which an ether / ester compound having an alkylene structure is crosslinked with a polycarboxylic acid and the terminal is esterified with a monocarboxylic acid; amine compounds such as compounds having a (poly)oxyalkylene structure in which an alkylene oxide is added to a primary organic amine; partial ester compounds of carboxylic acids and polyhydric alcohols; amide compounds in which an amine compound is condensed with a carboxylic acid; compounds having a (poly)oxyalkylene structure in which an alkylene oxide is added to a fatty acid amide; and compounds having a polyoxyalkylene structure such as a block copolymer having a polyoxyethylene chain and a polyoxypropylene chain.

[0064] Specific examples of alcohols used as raw materials for the nonionic surfactant (D) include: (1) linear alkyl alcohols such as methanol, ethanol, propanol, butanol, pentanol, hexanol, octanol, nonanol, decanol, undecanol, dodecanol, tridecanol, tetradecanol, pentadecanol, hexadecanol, heptadecanol, octadecanol, nonadecanol, eicosanol, heneicosanol, docosanol, tricosanol, tetracosanol, pentacosanol, hexacosanol, heptacosanol, octacosanol, nonacosanol, and triacontanol; (2) isopropanol, isobutanol, isohexanol, 2-ethylhexanol, isononanol, isodecanol, isododecanol, isotridecanol, isotetradecanol, isopentadecanol, and isohexanol; (3) linear alkenyl alcohols such as tetradecenol, hexadecenol, heptadecenol, octadecenol, and nonadecenol; (4) branched alkenyl alcohols such as isohexadecenol and isooctadecenol; (5) cyclic alkyl alcohols such as cyclopentanol and cyclohexanol; and (6) aromatic alcohols such as phenol, nonylphenol, benzyl alcohol, monostyrenated phenol, distyrenated phenol, and tristyrenated phenol.

[0065] Specific examples of carboxylic acids used as raw materials for the nonionic surfactant (D) include: (1) linear alkyl carboxylic acids such as octylic 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, heneicosanoic acid, and docosanoic acid; (2) branched alkyl carboxylic acids such as 2-ethylhexanoic acid, isododecanoic acid, isotridecanoic acid, isotetradecanoic acid, isohexadecanoic acid, and isooctadecanoic acid; (3) linear alkenyl carboxylic acids such as octadecenoic acid, octadecadienoic acid, and octadecatrienoic acid; (4) aromatic carboxylic acids such as benzoic acid; (5) hydroxycarboxylic acids such as lactic acid, citric acid, and ricinoleic acid; and (6) polycarboxylic acids such as adipic acid, sebacic acid, and tricarbaryl.

[0066] The alkylene oxide used as a raw material for forming the (poly)oxyalkylene structure of the nonionic surfactant (D) is preferably an alkylene oxide having 2 to 4 carbon atoms. Specific examples of alkylene oxide include ethylene oxide, propylene oxide, and butylene oxide. The number of moles of alkylene oxide added is set appropriately, but is preferably 0.1 to 200 moles, more preferably 1 to 150 moles, and even more preferably 2 to 100 moles. Any combination of the above upper and lower limits is also possible. The number of moles of alkylene oxide added indicates the number of moles of alkylene oxide per mole of the compound to be added in the charged raw material. As the alkylene oxide, one type of alkylene oxide may be used alone, or two or more types of alkylene oxides may be used in appropriate combination. When two or more types of alkylene oxide are used, the addition form may be any of block addition, random addition, and a combination of block addition and random addition, and is not particularly limited.

[0067] Specific examples of polyhydric alcohols used as raw materials for the nonionic surfactant (D) 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, glycerin, 2-methyl-2-hydroxymethyl-1,3-propanediol, trimethylolpropane, sorbitan, pentaerythritol, and sorbitol.

[0068] Specific examples of the aliphatic amine used as a raw material for the nonionic surfactant (D) include methylamine, ethylamine, butylamine, octylamine, laurylamine, octadecylamine, octadecenylamine, and coconut amine.

[0069] Specific examples of fatty acid amides used as raw materials for the nonionic surfactant (D) include octylic acid amide, lauric acid amide, palmitic acid amide, stearic acid amide, oleic acid amide, behenic acid amide, lignoceric acid amide, amides of fatty acids and diethanolamine, and amides of fatty acids and ethyleneamine.

[0070] Specific examples of the nonionic surfactant (D) include a compound obtained by adding an alkylene oxide to oleic acid, a compound obtained by adding an alkylene oxide to hydrogenated castor oil, a compound obtained by esterifying a compound obtained by adding an alkylene oxide to hydrogenated castor oil with oleic acid, a compound obtained by esterifying a compound obtained by adding an alkylene oxide to hydrogenated castor oil with maleic acid, a compound obtained by esterifying a compound obtained by adding an alkylene oxide to hydrogenated castor oil with adipic acid and further esterifying it with stearic acid, and a compound obtained by esterifying tetradecyl alcohol with ethyl methyl ester. Examples of the alkylene oxide include a compound in which alkylene oxide and propylene oxide are randomly added, a compound in which alkylene oxide is added to laurylamine, a compound in which alkylene oxide is added to stearylamine, an ester compound of oleic acid with a compound in which alkylene oxide is added to glycerin, an ester compound of palmitic acid with a compound in which alkylene oxide is added to glycerin, an ester compound of maleic acid with a compound in which alkylene oxide is added to hydrogenated castor oil, and an ester compound of polyethylene glycol and oleic acid.

[0071] These nonionic surfactants (D) may be used singly or in appropriate combination of two or more. The lower limit of the content of the nonionic surfactant (D) in the nonvolatile content of the treatment agent may be appropriately set, but is preferably 20% by mass or more, more preferably 25% by mass or more. When the content is 20% by mass or more, the effects of the present invention can be further improved. The upper limit of the content of the nonionic surfactant (D) may be appropriately set, but is preferably 70% by mass or less, more preferably 60% by mass or less. When the content is 70% by mass or less, the effects of the present invention can be efficiently improved.

[0072] In one aspect of this embodiment, the content of the nonionic surfactant (D) in the nonvolatile content of the treatment agent is, for example, 40.5% by mass or more, 48% by mass or more, 49.9% by mass or more, 51% by mass or more, 51.825% by mass or more, 51.89% by mass or more, 52.5% by mass or more, 52.95% by mass or more, 54.915% by mass or more, or 54.925% by mass or more. Similarly, the content of the nonionic surfactant (D) in the nonvolatile content of the treatment agent is, for example, 40.5% by mass or less, 48% by mass or less, 49.9% by mass or less, 51% by mass or less, 51.825% by mass or more, 51.89% by mass or less, 52.5% by mass or less, 52.95% by mass or less, 54.915% by mass or less, or 54.925% by mass or less. Note that ranges combining the above upper and lower limits are also envisioned.

[0073] The nonvolatile content of the treatment agent preferably contains 0.03% by mass or more and 5% by mass or less of tertiary alkanolamine (A), 20% by mass or more and 70% by mass or less of smoothing agent (B), 0.1% by mass or more and 20% by mass or less of smoothing agent (B1), 0.1% by mass or more and 5% by mass or less of organic phosphate ester compound (C), and 20% by mass or more and 70% by mass or less of nonionic surfactant (D). By specifying these ranges, the effects of the present invention can be further improved. It should be noted that ranges obtained by arbitrarily combining the above upper and lower limits are also contemplated.

[0074] (Kinematic viscosity) The kinematic viscosity of the nonvolatile content of the treatment agent at 25°C is preferably 100 mm ２ / s or more 500mm ２ / s or less, more preferably 200 mm ２ / s or more 400mm ２ By specifying the kinematic viscosity at 25°C of the non-volatile content of the treatment agent within this range, it is possible to reduce fuzzing of synthetic fibers to which the treatment agent has been applied, particularly fuzzing of twisted yarns.

[0075] In one aspect of this embodiment, the kinematic viscosity (mm ２ / s) is, for example, 92 or more, 94 or more, 146 or more, 153 or more, 174 or more, 182 or more, 205 or more, 225 or more, 230 or more, 232 or more, 249 or more, 257 or more, 259 or more, 394 or more, 443 or more, or 539 or more. ２ / s) is, for example, 92 or less, 94 or less, 146 or less, 153 or less, 174 or less, 182 or less, 205 or less, 225 or less, 230 or less, 232 or less, 249 or less, 257 or less, 259 or less, 394 or less, 443 or less, or 539 or less. Ranges combining any of the above upper and lower limits are also contemplated.

[0076] The kinematic viscosity of the nonvolatile content of the treatment agent at 25°C was measured by the Cannon-Fenske method. (pH) The lower limit of the pH of a 1% by mass aqueous solution of the treatment agent at 25°C can be set as appropriate, but is preferably 7.5 or higher, more preferably 8.0 or higher. The upper limit of the pH of a 1% by mass aqueous solution of the treatment agent at 25°C can be set as appropriate, but is preferably 9.0 or lower, and preferably 8.8 or lower. By specifying the pH within this range, the effects of the present invention can be further improved. In one aspect of this embodiment, the pH of a 1% by mass aqueous solution of the treatment agent at 25°C is, for example, 7.6 or higher, 7.8 or higher, 8.0 or higher, 8.1 or higher, 8.2 or higher, 8.3 or higher, 8.5 or higher, 8.6 or higher, 8.7 or higher, or 8.8 or higher. Similarly, the pH of a 1% by weight aqueous solution of the treatment agent at 25°C is, for example, 7.6 or less, 7.8 or less, 8.0 or less, 8.1 or less, 8.2 or less, 8.3 or less, 8.5 or less, 8.6 or less, 8.7 or less, or 8.8 or less. Ranges combining any of the above upper and lower limits are also contemplated. The pH of the ion-exchanged water used to dilute the treatment agent during pH measurement is 6.0 to 7.0 at 25°C, and indicates the value measured within 30 minutes of preparing a 1% by weight aqueous solution. Furthermore, if the treatment agent contains a solvent, the 1% by weight aqueous solution is a mixture containing the solvent.

[0077] (Effects of this embodiment) The effects of the treatment agent of the first embodiment will be described. (1-1) The treatment agent of the first embodiment contains a tertiary alkanolamine (A) represented by formula (1), a smoothing agent (B), and an organic phosphate ester compound (C) that is at least one selected from organic phosphate esters and salts thereof, and is configured such that the mass ratio Ma / Mp of the content Ma of the tertiary alkanolamine (A) to the phosphorus content Mp detected by ICP atomic emission spectrometry is 6 or greater. Therefore, the flexibility of synthetic fibers to which the treatment agent is applied, particularly the flexibility of twisted yarns or cords made from synthetic fibers, can be improved. Furthermore, the fuzz of synthetic fibers to which the treatment agent is applied, particularly twisted yarn fuzz, can be reduced. Furthermore, tar cleaning can be improved.

[0078] Second Embodiment Next, a second embodiment of the synthetic fiber according to the present invention will be described. The synthetic fiber of this embodiment is a treated synthetic fiber having the non-volatile components of the treatment agent of the first embodiment adhered to its surface. The treatment agent may be applied to the synthetic fiber in the form of a dilution solution diluted with a dilution solvent, such as an organic solvent solution or an aqueous liquid. From the viewpoint of the adhesion of the treatment agent to the fiber and economic efficiency, it is preferable to use a hydrocarbon having 10 to 15 carbon atoms and / or water as the dilution solvent. The synthetic fiber is obtained by adhering a dilution solution such as an aqueous liquid to the synthetic fiber, for example, in a spinning or drawing process. The dilution solvent adhered to the synthetic fiber may be evaporated by a drawing process or a drying process.

[0079] (Synthetic Fibers) Specific examples of synthetic fibers to which the treatment agent of this embodiment is applied are not particularly limited and include, for example, (1) polyester fibers such as polyethylene terephthalate (PET), polytrimethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, polylactic acid, and composite fibers containing these polyester resins, (2) polyamide fibers such as nylon 6 and nylon 66, (3) polyacrylic fibers such as polyacrylic and modacrylic, and (4) polyolefin fibers such as polyethylene and polypropylene. Of these, application to polyester fibers is preferred.

[0080] There are no particular restrictions on the proportion of the treatment agent applied to the synthetic fibers, but it is preferable to apply the treatment agent at a proportion of 0.1% by mass to 3% by mass (excluding solvents such as water) relative to the synthetic fibers. This configuration further improves the effects of the present invention. There are also no particular restrictions on the method for applying the treatment agent, and known methods such as roller oiling, guide oiling using a metering pump, immersion oiling, and spray oiling can be used.

[0081] In the present invention, the use of the synthetic fiber is not particularly limited, but synthetic fibers used in industrial materials are preferred, and among these, rubber reinforcement applications are more preferred. For example, synthetic fibers used in the fields of automobiles, construction, commerce, agriculture / fisheries, civil engineering, etc., such as airbag fibers, seatbelt fibers, tire cord fibers, carpet fibers, tent fibers, advertising fabric fibers, fishing net fibers, conveyor belt fibers, and rope fibers, are more preferred.

[0082] (Effects of this embodiment) The effects of the synthetic fiber of the second embodiment will be described below. In addition to the effects of the above-described embodiments, the second embodiment has the following effects.

[0083] (2-1) The synthetic fiber of the second embodiment is coated with the treatment agent of the first embodiment. Therefore, according to the present invention, the flexibility of the synthetic fiber, particularly the flexibility of twisted yarns or cords made from the synthetic fiber, can be improved. Furthermore, the fuzz of the synthetic fiber, particularly the fuzz of twisted yarns after the twisting process, can be reduced. This improves the yarn quality of the synthetic fiber. This in turn improves the product properties of final products for rubber reinforcement applications, etc.

[0084] (Modifications) The above embodiment may be modified as follows: The above embodiment and the following modifications may be combined and implemented within the scope of technical compatibility.

[0085] Each of the treatment agents of the above embodiments may further contain other components used in ordinary treatment agents, such as solvents, stabilizers, antistatic agents, binders, antioxidants, UV absorbers, surfactants other than those mentioned above, as other components to maintain the quality of each treatment agent, within a range that does not impair the effects of the present invention. Note that, from the viewpoint of efficiently exerting the efficacy of the present invention, the amount of other components other than solvents used in ordinary treatment agents is preferably 10% by mass or less in each treatment agent.

[0086] Examples will be given below to more specifically illustrate the configuration and effects of the present invention, but the present invention is not limited to these examples. In the following examples and comparative examples, parts mean parts by mass, and % means % by mass.

[0087] Test Section 1 (Preparation of Treatment Agent) (Example 1) The treatment agent of Example 1 contained 0.5 parts (%) of dibutylethanolamine (A-1) as the tertiary alkanolamine (A), 5 parts of diisocetylthiodipropionate (B-1-1) as the smoothing agent (B), 20 parts of palm oil (B-2-2), 30 parts of trimethylolpropane trioleate (B-2-3), 1.5 parts of a salt (C-2) of a compound obtained by adding 10 moles of ethylene oxide (hereinafter referred to as EO) to isocetyl phosphate and laurylamine as the organic phosphate ester compound (C), 6.5 parts of a compound (D-1) obtained by adding 13 moles of EO to 1 mole of oleic acid as a nonionic surfactant, 5 parts of a compound (D-2) obtained by adding 12 moles of EO to 1 mole of hydrogenated castor oil, and 20 moles of EO to 1 mole of hydrogenated castor oil. The following was prepared by adding 12 parts of an ester compound (D-4) of a compound obtained by esterifying a 25-mol EO adduct of hydrogenated castor oil with oleic acid, 4 parts of a compound (D-6) obtained by esterifying a 25-mol EO adduct of hydrogenated castor oil with adipic acid and further esterifying it with stearic acid, 10 parts of a compound (mass average molecular weight 1500) (D-7) obtained by randomly adding EO and propylene oxide (hereinafter referred to as PO) to tetradecyl alcohol, 3 parts of a compound (D-9) obtained by adding 10 moles of EO to 1 mole of stearylamine, and, as other components, 1.5 parts of secondary alkane (having 14-18 carbon atoms) sulfonic acid sodium salt (E-1) and 1 part of bis[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionic acid][ethylenebis(oxyethylene)] (E-4) to a beaker and mixing them well.

[0088] Examples 2 to 17, Comparative Examples 1 to 12 The treating agents of Examples 2 to 17 and Comparative Examples 1 to 12 were prepared in the same manner as in Example 1 using the components shown in Tables 1 and 2.

[0089] The type and content of the tertiary alkanolamine (A), the type and content of the smoothing agent (B), the type and content of the organic phosphate ester compound (C), the type and content of the nonionic surfactant (D), and the type and content of the other component (E) in each example of the treatment agent are as shown in the "Tertiary alkanolamine (A)" column, the "smoothing agent (B)" column, the "organic phosphate ester compound (C)" column, the "nonionic surfactant (D)" column, and the "other component (E)" column in Tables 1 and 2, respectively.

[0090] 1% pH: In Tables 1 and 2, "1% pH" refers to the pH of a 1% aqueous solution of the treatment agent in each example at 25°C. The pH of the ion-exchanged water used to dilute the treatment agent when measuring the pH is 6.0 to 7.0 at 25°C, and the value is measured within 30 minutes of preparing the 1% aqueous solution. In addition, if the treatment agent contains a solvent, the 1% aqueous solution is taken as a mixture including the solvent.

[0091] - ICP optical emission spectrometry: First, the treatment agent was diluted with distilled water to a nonvolatile concentration of 1%. Phosphorus standard solutions with known concentrations of 0.001%, 0.005%, 0.01%, 0.05%, 0.1%, and 0.5% by mass were prepared. Furthermore, the distilled water used for diluting the samples was used as a 0% by mass standard solution. Measurements were taken using an ICP optical emission spectrometer (Shimadzu Corporation, ICPE-9000). The phosphorus content in the treatment agent was determined from the calibration curve. The results are shown in the "Phosphorus content Mp (%)" column in Tables 1 and 2.

[0092] In Tables 1 and 2, "Ma / Mp" indicates the ratio of the tertiary alkanolamine (A) content (%) to the phosphorus content Mp (%). The kinematic viscosity of the nonvolatile content of the kinematic viscosity treatment agent was measured at 25°C using the Cannon-Fenske method for the treatment agents of each Example and Comparative Example. The results are shown in the "Kinematic viscosity of nonvolatile content" column of Tables 1 and 2.

[0093]

[0094]

[0095] Details of the tertiary alkanolamine (A), smoothing agent (B), organic phosphate ester compound (C), nonionic surfactant (D), and other component (E) shown in Tables 1 and 2 are as follows.

[0096] <Tertiary alkanolamines (A)> A-1: ​​Dibutylethanolamine A-2: Diethylethanolamine A-3: Dimethylethanolamine A-4: Dihexylethanolamine a-1: Dilaurylethanolamine a-2: Dioctadecylethanolamine a-3: Diethanolamine a-4: Triethanolamine <Smoothing agents (B)> (Ester compounds (B1) having a thioether bond in the molecule) B-1-1: Diisocetyl thiodipropionate B-1-2: Di(2-dodecyl-1-tetradecanol)thiodipropionate B-1-3: Dioleyl thiodipropionate B-1-4: Monooleyl thiodipropionate B-1-5: Dilauryl thiodipropionate (Other smoothing agents) B-2-1: Rapeseed oil B-2-2: Palm oil B-2-3: Trimethylolpropane trioleate B-2-4: Trimethylolpropane tripartite nucleus fatty acid ester B-2-5: Glycerin monooleate B-2-6: Trimethylolpropane trilaurate (organic phosphate ester compounds (C)) C-1: Sodium oleyl phosphate C-2: Salt of isocetyl phosphate and a compound in which 10 moles of EO are added to laurylamine C-3: Salt of lauryl phosphate and a compound in which 10 moles of EO are added to laurylamine C-4: Phosphate ester of a compound in which 8 moles of EO are added to oleyl alcohol C-5: Salt of isocetyl phosphate and dibutylethanolamine C-6: Salt of isocetyl phosphate and diethylethanolamine (nonionic surfactants (D)) D-1: A compound in which 13 moles of EO are added to 1 mole of oleic acid D-2: A compound in which 12 moles of EO are added to 1 mole of hydrogenated castor oil D-3: A compound obtained by adding 20 moles of EO to 1 mole of hydrogenated castor oil. D-4: An ester compound of a compound obtained by adding 20 moles of EO to 1 mole of hydrogenated castor oil with oleic acid. D-5: An ester compound of a compound obtained by adding 20 moles of EO to 1 mole of hydrogenated castor oil with maleic acid. D-6: A compound obtained by esterifying a 25 mole EO adduct of hydrogenated castor oil with adipic acid and further esterifying it with stearic acid.D-7: Compound in which EO and PO are added randomly to tetradecyl alcohol (mass average molecular weight 1500) D-8: Compound in which 10 moles of EO are added to 1 mole of laurylamine D-9: Compound in which 10 moles of EO are added to 1 mole of stearylamine D-10: Ester compound of 2 moles of oleic acid with a compound in which 20 moles of EO are added to 1 mole of glycerin D-11: Ester compound of 2 moles of palmitic acid with a compound in which 20 moles of EO are added to 1 mole of glycerin D-12: Ester compound of maleic acid with a compound in which 30 moles of EO are added to 1 mole of hydrogenated castor oil D-13: Ester compound of 1 mole of polyethylene glycol (mass average molecular weight 600) and 2 moles of oleic acid (Other components (E)) E-1: Sodium salt of secondary alkane (having 14-18 carbon atoms) sulfonate E-2: Sodium salt of α-olefin (having 14-18 carbon atoms) sulfonate E-3: Sodium alkane (carbon number 13-16) sulfonate E-4: Bis[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionic acid][ethylenebis(oxyethylene)] E-5: Tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl isocyanurate) Test Section 2 (Attachment of Treatment Agent to Synthetic Fiber) - The treatment agent of each example in Test Section 1 for attachment of treatment agent to synthetic fiber was uniformly diluted with ion-exchanged water to make a 15% solution. The 15% solution was attached to unoiled polyethylene terephthalate fiber with 1670 dtex, 360 filaments, and an intrinsic viscosity of 1.01 using an oiling roller oiling method so that the amount of attached treatment agent was 1.0%.

[0097] Test Section 3 (Fluffing of Twisted Yarn) Two synthetic fibers to which the treatment agent of each example obtained in Test Section 2 had been applied were twisted with a twist count of 50 turns / 10 cm for the first twist and 50 turns / 10 cm for the second twist to form a twisted yarn cord. The amount of fluff generated per 100 m during the production of this twisted yarn was visually counted. The fluffing of the twisted yarn was evaluated according to the following criteria. The results are shown in the "Fluffing" column of Tables 1 and 2.

[0098] Evaluation criteria for twisted yarn fluff 5 (very good): 3 or less fluffs 4 (good): 4 to 7 fluffs 3 (good): 8 to 11 fluffs 2 (fair): 12 to 15 fluffs 1 (poor): 16 or more fluffs Test category 4 (manufacturing of reinforcing cords treated with adhesive) The twisted cord obtained in Test Section 3 was immersed in a first adhesive (epoxy compound (trade name: DENACOL EX-512, manufactured by Nagase ChemteX Corporation) / blocked isocyanate (trade name: ELASTRON BN-27, manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.) = 5 / 5 (solids ratio)), followed by heat treatment, and further immersed in a second adhesive (an RFL solution of resorcin (trade name: RESORCINOL, manufactured by Kishida Chemical Co., Ltd.) / formalin (trade name: FORMALDEHYDE LIQUID (37%), manufactured by Kishida Chemical Co., Ltd.) / latex (trade name: PYRATEX, manufactured by Nippon A&L Co., Ltd.) = 1.5 / 0.5 / 8 (solids ratio)), followed by heat treatment, to obtain an adhesive-treated reinforcing cord.

[0099] Test Section 5 (Evaluation of Flexibility) The reinforcing cord obtained in Test Section 4 was cut to a length of 38.1 mm (1.5 inches) and a width of 12.7 mm (0.5 inches) was prepared to prepare test specimens. In accordance with JIS L 1096, Bending Resilience Method A, the test specimens were subjected to a Gurley type flexibility tester, and the flexibility was calculated from the reading on the scale plate according to the following formula and evaluated according to the following criteria. The results are shown in the "Flexibility" column of Tables 1 and 2.

[0100] S=R×(D1W1+D2W2+D3W3)×(L-12.7) ２ / b x 3.375 x 10 －５S: Flexibility (Gurley stiffness) (mg) R: Reading on the scale D1, D2, D3: Distance from the pendulum fulcrum to the weight attachment position [25.4 mm (1 inch), 50.8 mm (2 inches), 101.6 mm (4 inches)] W1, W2, W3: Mass (g) of the weight attached to the holes at D1, D2, and D3 L: Length of the test piece (mm) b: Width of the test piece (mm) Flexibility evaluation criteria 5 (Excellent): Flexibility is less than 30 mg 4 (Excellent): Flexibility is 30 mg or more and less than 40 mg 3 (Good): Flexibility is 40 mg or more and less than 50 mg 2 (Fair): Flexibility is 50 mg or more and less than 60 mg 1 (Fail): Flexibility is 60 mg or more Test category 6 (Tar cleanability) Immediately after preparation, each treatment agent was diluted with an organic solvent (a mixed solvent of n-hexane and ethanol) to prepare a 15% diluted solution. The diluted solution was applied to oil-free polyethylene terephthalate fibers with 1670 dtex, 360 filaments, and an intrinsic viscosity of 1.01 using the guide oiling method to a nonvolatile content of 5.0% to prepare evaluation yarns. The evaluation yarns were run for 12 hours in contact with a matte chrome pin at a surface temperature of 240°C at an initial tension of 1.5 kg and a yarn speed of 0.1 m / min. The brown tar adhering to the fiber run and its surroundings was rubbed at 180°C with a cotton swab impregnated with a glycerin solution prepared to a concentration of 1% NaOH, and the number of strokes (reciprocations) required until the brown tar disappeared was measured. Tar cleanability was evaluated according to the following criteria. The results are shown in the "Tar Cleanability" column of Tables 1 and 2.

[0101] Evaluation criteria for tar cleanability: 5 (very excellent): Less than 50 times; 4 (excellent): 50 or more times but less than 100 times; 3 (good): 100 or more times but less than 150 times; 2 (fair): 150 or more times but less than 200 times; 1 (poor): 200 or more times. From the results in the table above, it can be seen that the treatment agent of the present invention can improve the softness of synthetic fibers to which the treatment agent is applied, reduce fuzz, and also improve tar cleanability.

Claims

1. A synthetic fiber treatment agent comprising a tertiary alkanolamine (A) represented by the following formula (1), a smoothing agent (B), and an organic phosphate ester compound (C) which is at least one selected from organic phosphate esters and their salts, wherein the mass ratio Ma / Mp of the content of tertiary alkanolamine (A), Ma, to the phosphorus content, Mp, detected by ICP atomic emission spectrometry, is 6 or more. (In formula (1), R １ and R ２ are each a monovalent hydrocarbon group having 1 to 8 carbon atoms, ３ is a divalent hydrocarbon group having 1 to 4 carbon atoms.

2. The synthetic fiber processing agent according to claim 1, wherein the smoothing agent (B) contains an ester compound (B1) having a thioether bond in the molecule.

3. The kinematic viscosity of the nonvolatile content of the synthetic fiber treatment agent is 100 mm at 25°C. ２ / s or more 500mm ２ 2. The synthetic fiber treating agent according to claim 1, wherein the viscosity of said synthetic fiber treating agent is 1 / s or less.

4. R in the formula (1) １ , R ２ is a monovalent hydrocarbon group having 2 to 4 carbon atoms, and R ３ 2. The synthetic fiber treating agent according to claim 1, wherein is a divalent hydrocarbon group having 1 to 4 carbon atoms.

5. The synthetic fiber treating agent according to claim 1, wherein the organic phosphate ester compound (C) is at least one selected from the group consisting of phosphate esters of aliphatic alcohols having 16 to 24 carbon atoms and salts thereof.

6. The synthetic fiber treating agent according to claim 2, wherein the ester compound (B1) is a complete ester of an aliphatic alcohol having 16 to 24 carbon atoms and thiodipropionic acid.

7. The synthetic fiber treatment agent according to claim 2, wherein the non-volatile components of the synthetic fiber treatment agent contain 0.03% by mass or more and 5% by mass or less of the tertiary alkanolamine (A), 20% by mass or more and 70% by mass or less of the smoothing agent (B), 0.1% by mass or more and 20% by mass or less of the smoothing agent (B1), and 0.1% by mass or more and 5% by mass or less of the organic phosphate ester compound (C).

8. The synthetic fiber treating agent according to claim 1, further comprising a nonionic surfactant (D).

9. The synthetic fiber treatment agent according to claim 2, further comprising a nonionic surfactant (D), and the nonvolatile components of the synthetic fiber treatment agent contain the tertiary alkanolamine (A) in an amount of 0.03% by mass or more and 5% by mass or less, the smoothing agent (B) in an amount of 20% by mass or more and 70% by mass or less, the smoothing agent (B1) in an amount of 0.1% by mass or more and 20% by mass or less, the organic phosphate ester compound (C) in an amount of 0.1% by mass or more and 5% by mass or less, and the nonionic surfactant (D) in an amount of 20% by mass or more and 70% by mass or less.

10. The synthetic fiber treatment agent according to claim 1, wherein the pH of an aqueous solution of the synthetic fiber treatment agent having a non-volatile content of 1% by mass at 25°C is 7.5 or more and 9.0 or less.

11. Synthetic fibers having the synthetic fiber treatment agent according to any one of claims 1 to 10 adhered thereto.

12. The synthetic fiber according to claim 11, wherein the synthetic fiber is a polyester-based synthetic fiber.