Method for producing synthetic fiber treatment agent, synthetic fiber treatment agent, and use thereof

Abstract

The purpose of the present invention is to provide a synthetic fiber treatment agent which makes it possible to achieve both a reduction in the amount of thermal degradation product and tension fluctuation suppression.　Provided is a method for producing a synthetic fiber treatment agent which satisfies specific conditions 1 and 2 and which contains an ester component (A) and a nonionic surfactant (B) that does not have an ester bond and that has a polyoxyalkylene skeleton, wherein: the ester component (A) contains at least one compound selected from ester compounds represented by general formula (1) and compounds having a structure in which a polyoxyalkylene glycol and a fatty acid form an ester bond; the nonionic surfactant (B) includes a nonionic surfactant (B1) which has a C12-15 alkyl group; and the proportion of the nonionic surfactant (B) in the non-volatile content of the treatment agent, the strong acid value, the saponification value, and the iodine value of the non-volatile content of the treatment agent, the Zr element and Ti element content, the K element and Na element content, and the Si element content are within specific ranges.

Description

Method for manufacturing synthetic fiber treatment agents, treatment agents for synthetic fibers, and their use

[0001] This invention relates to a method for producing a synthetic fiber treatment agent, a treatment agent for synthetic fibers, and its use.

[0002] In the manufacture of synthetic fibers for industrial and apparel use, a fiber treatment agent is applied, and the fibers undergo a process that involves high-temperature thermal treatment. Therefore, there is a need for a treatment agent that does not easily contaminate equipment even when subjected to high-temperature thermal treatment for extended periods. However, with conventional synthetic fiber treatment agents (Patent Document 1), when synthetic fibers are manufactured over a long period, thermal degradation products of the treatment agent accumulate, contaminating the equipment, which leads to an increase in fluff and yarn breakage, and also results in time-consuming equipment cleaning.

[0003] Japanese Patent Application Publication No. 2018-150665

[0004] An investigation into the cause revealed that the problem stemmed from the inability to simultaneously reduce the amount of thermally degraded material and suppress tension fluctuations. Therefore, the objective of the present invention is to provide a method for producing a synthetic fiber treatment agent that can achieve both a reduction in the amount of thermally degraded material and suppression of tension fluctuations, as well as a synthetic fiber treatment agent and its applications.

[0005] As a result of diligent research, the present inventors have found that by creating a synthetic fiber treatment agent consisting of specific components and having a specific composition, it is possible to produce a synthetic fiber treatment agent having a specific residual rate after heat treatment for a specific time, thereby solving the problems of the present invention. Furthermore, they have found that in a synthetic fiber treatment agent consisting of specific components, the non-volatile components of the treatment agent have a specific strong acid value and saponification value, and the residual rate after heat treatment for a specific time is within a specific range, thereby solving the problems of the present invention, and thus arriving at the present invention. That is, the present invention includes the following embodiments. <1> A method for producing a synthetic fiber treatment agent that contains a nonionic surfactant (B) having a polyoxyalkylene skeleton without ester bonds and an ester component (A), and satisfies the following conditions 1 and 2, wherein the ester component (A) comprises at least one selected from an ester compound represented by the following general formula (1) and a compound having a structure in which polyoxyalkylene glycol and a fatty acid are ester-bonded, the nonionic surfactant (B) comprises a nonionic surfactant (B1) having an alkyl group having 12 to 15 carbon atoms, the proportion of the nonionic surfactant (B) in the nonvolatile content of the treatment agent is 40 to 97% by weight, the strong acid value of the nonvolatile content of the treatment agent is 0.00 to 0.10 mg KOH / g, the saponification value of the nonvolatile content of the treatment agent is 2 to 20 mg KOH / g, and the iodine value of the nonvolatile content of the treatment agent is 0 to 8.6. A method for producing a treatment agent for synthetic fibers, characterized in that the total content of Zr and Ti elements in the nonvolatile matter of the treatment agent is 0 to 54 ppm, the total content of K and Na elements in the nonvolatile matter of the treatment agent is 50 to 2000 ppm, and the content of Si elements in the nonvolatile matter of the treatment agent is 50 to 2000 ppm. Condition 1: The residual rate of the nonvolatile matter of the treatment agent after heating 0.5 g at 200°C for 1 hour is 10 to 30% by weight. Condition 2: The residual rate of the nonvolatile matter of the treatment agent after heating 0.5 g at 200°C for 24 hours is greater than 0 to 6% by weight. (In the formula, R １ R represents an alkyl or alkenyl group having 4 to 24 carbon atoms. ２) represents an alkyl or alkenyl group having 6 to 24 carbon atoms.) <2> A synthetic fiber treatment agent comprising a nonionic surfactant (B) having a polyoxyalkylene skeleton without ester bonds and an ester component (A), wherein the ester component (A) comprises at least one selected from an ester compound represented by the following general formula (1) and a compound having a structure in which polyoxyalkylene glycol and a fatty acid are ester-bonded, the nonionic surfactant (B) comprises a nonionic surfactant (B1) having an alkyl group having 12 to 15 carbon atoms, the proportion of the nonionic surfactant (B) in the nonvolatile content of the treatment agent is 40 to 97% by weight, the strong acid value of the nonvolatile content of the treatment agent is 0.00 to 0.10 mg KOH / g, the saponification value of the nonvolatile content of the treatment agent is 2 to 20 mg KOH / g, and the following conditions 1 and 2 are satisfied. Condition 1: The remaining percentage of non-volatile components of the treatment agent after heating 0.5 g at 200°C for 1 hour is 10 to 30% by weight. Condition 2: The remaining percentage of non-volatile components of the treatment agent after heating 0.5 g at 200°C for 24 hours is greater than 0% to 6% by weight. (In the formula, R １ R represents an alkyl or alkenyl group having 4 to 24 carbon atoms. ２) <3> The synthetic fiber treatment agent according to <2>, wherein the Si element content in the nonvolatile content of the treatment agent is 50 to 2000 ppm. <4> The synthetic fiber treatment agent according to <2> or <3>, wherein the total content of K element and Na element in the nonvolatile content of the treatment agent is 50 to 2000 ppm. <5> The synthetic fiber treatment agent according to any one of <2> to <4>, wherein the iodine value of the nonvolatile content of the treatment agent is 8.6 or less. <6> The synthetic fiber treatment agent according to any one of <2> to <5>, wherein the total content of Zr element and Ti element in the nonvolatile content of the treatment agent is 30 ppm or less. <7> The synthetic fiber treatment agent according to any one of <2> to <6>, wherein the proportion of the nonionic surfactant (B1) in the nonvolatile content of the treatment agent is 50 to 95% by weight. <8> A synthetic fiber treatment agent according to any one of <2> to <7>, wherein the proportion of the silicone compound in the nonvolatile content of the treatment agent is 0.05 to 1.5% by weight. <9> A synthetic fiber treatment agent according to any one of <2> to <8>, which contains more than 0 to 16% by weight of water. <10> A synthetic fiber obtained by applying the synthetic fiber treatment agent according to any one of <2> to <9> to a raw synthetic fiber. <11> A method for producing a synthetic fiber, comprising the step of applying the synthetic fiber treatment agent according to any one of <2> to <9> to a raw synthetic fiber. <12> A fiber structure containing the synthetic fiber according to <10>.

[0006] The method for producing the synthetic fiber treatment agent of the present invention makes it possible to produce a synthetic fiber treatment agent that can achieve both a reduction in the amount of thermally degraded materials and suppression of tension fluctuations. The synthetic fiber treatment agent of the present invention can achieve both a reduction in the amount of thermally degraded materials and suppression of tension fluctuations. As a result, it has excellent productivity for synthetic fibers. The method for producing synthetic fibers of the present invention uses a synthetic fiber treatment agent that can achieve both a reduction in the amount of thermally degraded materials and suppression of tension fluctuations, thus resulting in excellent productivity for synthetic fibers. The synthetic fibers of the present invention have excellent quality. The fiber structures of the present invention have excellent quality.

[0007] A first aspect of the present invention, a treatment agent for synthetic fibers (hereinafter sometimes simply referred to as the treatment agent), contains a specific ester component (A) and a specific nonionic surfactant (B) that does not have an ester bond, the strong acid value and saponification value of the nonvolatile components of the treatment agent are within a specific range, and it satisfies specific conditions 1 and 2 regarding the residual rate after heating. A detailed explanation follows below.

[0008] [Ester component (A)] The treatment agent of the present invention contains ester component (A). There are no particular limitations on ester component (A) as long as it is a compound having an ester bond, but examples of known components that are commonly used as synthetic fiber treatment agents include: 1) ester compounds having a structure in which an aliphatic monohydric alcohol and a fatty acid are ester-bonded (A1), 2) ester compounds having a structure in which an aliphatic polyhydric alcohol and a fatty acid are ester-bonded (A2), 3) ester compounds having a structure in which an aliphatic monohydric alcohol and an aliphatic polycarboxylic acid are ester-bonded (A3), 4) aromatic ester compounds having an aromatic ring in the molecule (A4), 5) sulfur-containing ester compounds (A5), and 6) ester compounds having a polyoxyalkylene group (A6). One or more types of ester component (A) can be used.

[0009] 1) Ester compound (A1) Ester compound (A1) is a compound having a structure in which an aliphatic monohydric alcohol and a fatty acid (aliphatic monohydric carboxylic acid) are ester-bonded, and is a compound that does not have a polyoxyalkylene group in its molecule. One or more types of ester compound (A1) can be used. There are no particular limitations on ester compound (A1), but it is preferably a compound represented by the following general formula (1).

[0010] (In the formula, R １ R represents an alkyl or alkenyl group having 4 to 24 carbon atoms. ２ (This represents an alkyl or alkenyl group having 6 to 24 carbon atoms.)

[0011] In formula (1), R １The number of carbon atoms is not particularly limited, but is preferably 6 to 22 from the viewpoint of smoothness. The upper limit of the number of carbon atoms is more preferably 20, still more preferably 18, and particularly preferably 16. On the other hand, the lower limit of the number of carbon atoms is more preferably 8, still more preferably 10, and particularly preferably 12. Further, for example, 8 to 20 is more preferable, and 10 to 18 is even more preferable. R １ may be either an alkyl group or an alkenyl group, but an alkyl group is preferable from the viewpoint of excellent heat resistance.

[0012] In formula (1), R ２ The number of carbon atoms is not particularly limited, but is preferably 6 to 22 from the viewpoint of smoothness. The upper limit of the number of carbon atoms is more preferably 20, still more preferably 18, and particularly preferably 16. On the other hand, the lower limit of the number of carbon atoms is more preferably 8, still more preferably 10, and particularly preferably 12. Further, for example, 8 to 20 is more preferable, and 10 to 18 is even more preferable. R ２ may be either an alkyl group or an alkenyl group, but an alkenyl group is preferable from the viewpoint that the oil film strength is high and fluff is less likely to occur.

[0013] The ester compound (A1) is not particularly limited, and examples thereof include 2-decyltetradecanoyl erucate, 2-decyltetradecanoyl oleate, 2-octyldodecyl stearate, 2-ethylhexyl palmitate, 2-ethylhexyl stearate, butyl palmitate, butyl stearate, butyl oleate, 2-ethylhexyl oleate, lauryl oleate, isotridecyl stearate, hexadecyl stearate, isostearyl oleate, oleyl octanoate, oleyl laurate, oleyl palmitate, oleyl stearate, and oleyl oleate. Among these, 2-decyltetradecanoyl oleate, 2-octyldodecyl stearate, 2-ethylhexyl palmitate, 2-ethylhexyl stearate, lauryl oleate, isotridecyl stearate, hexadecyl stearate, isostearyl oleate, and oleyl oleate are preferable.

[0014] Ester compound (A1) can be synthesized and obtained by known methods using commercially available fatty acids and aliphatic monohydric alcohols.

[0015] 2) Ester compound (A2) Ester compound (A2) is a compound having a structure in which an aliphatic polyhydric alcohol and a fatty acid (aliphatic monocarboxylic acid) are ester-bonded, and is a compound that does not have a polyoxyalkylene group in its molecule. One or more types of ester compound (A2) can be used.

[0016] The aliphatic polyhydric alcohol constituting the ester compound (A2) is not particularly limited as long as it is divalent or higher, and one or more types can be used. From the viewpoint of oil film strength, the polyhydric alcohol is preferably trivalent or higher, more preferably trivalent to tetravalent, and even more preferably trivalent. Examples of aliphatic polyhydric alcohols include ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 2-methyl-1,3-propanediol, 1,5-pentanediol, 1,6-hexanediol, neopentyl glycol, cyclohexanediol, cyclohexanedimethanol, glycerin, trimethylolpropane, pentaerythritol, erythritol, diglycerin, sorbitan, sorbitol, ditrimethylolpropane, dipentaerythritol, triglycerin, tetraglycerin, sucrose, and the like. Among these, glycerin, trimethylolpropane, pentaerythritol, erythritol, diglycerin, sorbitan, sorbitol, ditrimethylolpropane, dipentaerythritol, and sucrose are preferred, glycerin, trimethylolpropane, pentaerythritol, erythritol, diglycerin, and sorbitan are more preferred, and glycerin and trimethylolpropane are even more preferred.

[0017] The fatty acids constituting the ester compound (A2) may be saturated or unsaturated. There is no particular limit to the number of unsaturated bonds, but one, two, or three are preferred in terms of smoothness, heat resistance, and smoke generation. There is no particular limit to the number of carbon atoms in the fatty acid, but 8 to 24 are preferred in terms of achieving both oil film strength and smoothness. The upper limit of the number of carbon atoms is more preferably 20, even more preferably 18, and particularly preferably 16. On the other hand, the lower limit of the number of carbon atoms is more preferably 10, even more preferably 12, and particularly preferably 14. Also, for example, 10 to 20 is more preferred, and 12 to 18 is even more preferred. One or more types of fatty acids may be used, and saturated fatty acids and unsaturated fatty acids may be used in combination.

[0018] Examples of fatty acids include butyric acid, crotonic acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, lauric acid, myristic acid, myristoleic acid, pentadecanoic acid, palmitic acid, palmitoleic acid, isocetyl acid, margaric acid, stearic acid, isostearic acid, oleic acid, elaidic acid, vaccenic acid, linoleic acid, linolenic acid, tuberculinostearic acid, arachidic acid, isoeicosanoic acid, gadoleic acid, eicosenoic acid, docosanoic acid, isodocosanoic acid, erucic acid, tetracosanoic acid, isotetracosanoic acid, nervonic acid, cerotic acid, montanic acid, and melissic acid. Among these, caprylic acid, pelargonic acid, capric acid, lauric acid, myristic acid, myristoleic acid, pentadecanoic acid, palmitic acid, palmitoleic acid, isocetyl acid, margaric acid, stearic acid, isostearic acid, oleic acid, elaidic acid, vaccenic acid, linoleic acid, linolenic acid, tubercurostearic acid, arachidic acid, isoeicosanoic acid, gadoleic acid, eicosenoic acid, docosanoic acid, isodocosanoic acid, erucic acid, tetracosanoic acid, isotetracosanoic acid, and nervonic acid are preferred, and capric acid, lauric acid, myristic acid, and myristoleic acid are preferred. Acids, pentadecanoic acid, palmitic acid, palmitoleic acid, isocetyl acid, margaric acid, stearic acid, isostearic acid, oleic acid, elaidic acid, vaccenic acid, linoleic acid, linolenic acid, tuberculinostearic acid, arachidic acid, isoeicosanoic acid, gadoleic acid, and eicosenoic acid are more preferred, and lauric acid, myristic acid, myristoleic acid, pentadecanoic acid, palmitic acid, palmitoleic acid, isocetyl acid, margaric acid, stearic acid, isostearic acid, oleic acid, elaidic acid, vaccenic acid, linoleic acid, and linolenic acid are even more preferred.

[0019] The ester compound (A2) is a compound having one or more ester bonds in its molecule, but from the viewpoint of spinnability, it is preferable that it is a compound having two or more ester bonds in its molecule, and more preferably a compound having three ester bonds in its molecule. There are no particular limitations on the iodine value of the ester compound (A2).

[0020] The weight-average molecular weight of the ester compound (A2) is preferably 150 to 1200 in terms of smoothness and low smoke generation. The upper limit of the average molecular weight is more preferably 1150, and even more preferably 1100. On the other hand, the lower limit of the average molecular weight is more preferably 300, and even more preferably 500. Also, for example, 300 to 1150 is more preferably, and even more preferably 500 to 1100. The weight-average molecular weight in this invention was calculated using a high-speed gel permeation chromatography apparatus HLC-8220GPC manufactured by Tosoh Corporation, by injecting a sample concentration of 3 mg / cc into separation columns KF-402HQ and KF-403HQ manufactured by Showa Denko K.K., and measuring the peaks with a differential refractive index detector.

[0021] Examples of ester compounds (A2) include trimethylolpropane tricaprylate, trimethylolpropane tricaprinate, trimethylolpropane trilaurate, trimethylolpropane trioleate, trimethylolpropane (laurate, myristylate, palmitate), trimethylolpropane (laurate, myristylate, oleate), trimethylolpropane (tripalme kernel fatty acid ester), trimethylolpropane (coconut fatty acid ester), trimethylol Trimethylolpropane dicaprylate, trimethylolpropane dicaprinate, trimethylolpropane dilaurate, trimethylolpropane dioleate, trimethylolpropane (laurate, myristylate), trimethylolpropane (laurate, oleate), trimethylolpropane (myristylate, oleate), trimethylolpropane (dipalm kernel fatty acid ester), trimethylolpropane (coconut fatty acid ester), coconut oil, rapeseed oil, palm oil, palm olein oil, sunflower Salad oil, sesame oil, soybean oil, linseed oil, blended salad oil, glycerin trilaurate, glycerin trioleate, glycerin triisostearate, glycerin dioleate, glycerin monolaurate, diglycerin dioleate, sorbitan trioleate, sorbitan (laurate, myristylate, oleate), sorbitan dilaurate, sorbitan monooleate, pentaerythritol tetracaprylate, pentaerythritol tetracaprinate, pentaerythritol tetralaurate Examples include erythritol tetralaurate, pentaerythritol (tetrapalm kernel fatty acid ester), pentaerythritol (tetracoconut fatty acid ester), erythritol trioleate, erythritol dipalmitate, 1,6-hexanediol dioleate, glycerin monolaurate, glycerin dilaurate, glycerin monooleate, glycerin dioleate, sorbitan monooleate, sorbitan dioleate, sucrose monolaurate, sucrose dilaurate, etc.

[0022] The ester compound (A2) may be one synthesized by a known method using commercially available fatty acids and aliphatic polyhydric alcohols. Alternatively, natural esters obtained from natural sources such as fruits, seeds, or flowers that satisfy the composition of ester compound (A2) may be used as is, or, if necessary, natural esters may be purified by a known method, or further purified esters may be separated and re-purified using a known method based on the difference in melting points. Alternatively, esters obtained by transesterifying two or more natural esters (fats and oils) may be used.

[0023] 3) Ester Compound (A3) Ester compound (A3) is a compound having a structure in which an aliphatic monohydric alcohol and an aliphatic polyhydric carboxylic acid are ester-bonded, and is a compound that does not have a polyoxyalkylene group in its molecule. One or more types of ester compound (A3) can be used.

[0024] The aliphatic monohydric alcohol constituting the ester compound (A3) is not particularly limited, and one or more types may be used. The aliphatic monohydric alcohol may be saturated or unsaturated. There is no particular limit to the number of unsaturated bonds, but three or fewer is preferred in terms of smoothness. The carbon number of the aliphatic monohydric alcohol is preferably 8 to 24 from the viewpoint of smoothness and oil film strength. The upper limit of the carbon number is more preferably 22, even more preferably 20, and particularly preferably 18. On the other hand, the lower limit of the carbon number is more preferably 12, even more preferably 14, and particularly preferably 16. Also, for example, 12 to 22 is more preferred, and 14 to 20 is even more preferred. One or more types of aliphatic monohydric alcohols may be used, and saturated aliphatic monohydric alcohols and unsaturated aliphatic monohydric alcohols may be used in combination.

[0025] Examples of aliphatic monohydric alcohols include octyl alcohol, isooctyl alcohol, lauryl alcohol, myristyl alcohol, myristrail alcohol, cetyl alcohol, isocetyl alcohol, palmitrail alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, vaccenyl alcohol, gadleyl alcohol, arachidyl alcohol, isoicosanyl alcohol, eicosenoyl alcohol, behenyl alcohol, isodocosanyl alcohol, erukanyl alcohol, lignocerinyl alcohol, isotetracosanyl alcohol, nerbonyl alcohol, cerotinyl alcohol, montanyl alcohol, and merisinyl alcohol. Among these, octyl alcohol, isooctyl alcohol, lauryl alcohol, myristyl alcohol, myristyl alcohol, cetyl alcohol, isocetyl alcohol, palmitrail alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, baxenyl alcohol, gadleyl alcohol, arachidyl alcohol, isoicosanyl alcohol, eicosenoyl alcohol, behenyl alcohol, isodocosanyl alcohol, erukanyl alcohol, lignocerinyl alcohol, isotetracosanyl alcohol, and nerbonyl alcohol are preferred, myristrail alcohol, palmitrail alcohol, oleyl alcohol, elaidyl alcohol, baxenyl alcohol, gadleyl alcohol, eicosenoyl alcohol, erukanyl alcohol, and nerbonyl alcohol are more preferred, and oleyl alcohol, elaidyl alcohol, baxenyl alcohol, gadleyl alcohol, eicosenoyl alcohol, and erukanyl alcohol are even more preferred.

[0026] The aliphatic polycarboxylic acid constituting the ester compound (A3) is not particularly limited as long as it has a valency of 2 or more, and one type or two or more types thereof can be used. The aliphatic polycarboxylic acid used in the present invention does not contain sulfur-containing polycarboxylic acids such as thiodipropionic acid. The valency of the aliphatic polycarboxylic acid is preferably divalent. Similarly, it is preferable that the molecule does not contain a hydroxyl group. Examples of the aliphatic polycarboxylic acid include citric acid, isocitric acid, malic acid, aconitic acid, oxaloacetic acid, oxalosuccinic acid, succinic acid, fumaric acid, maleic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, and the like. Among these, aconitic acid, oxaloacetic acid, oxalosuccinic acid, succinic acid, fumaric acid, maleic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, and sebacic acid are preferred; and fumaric acid, maleic acid, adipic acid, pimelic acid, suberic acid, azelaic acid, and sebacic acid are more preferred.

[0027] Examples of the ester compound (A3) include dioctyl adipate, dilauryl adipate, dioleyl adipate, diisocetyl adipate, dioctyl sebacate, dilauryl sebacate, dioleyl sebacate, diisocetyl sebacate, and the like.

[0028] The ester compound (A3) is a compound having one or more ester bonds in the molecule. There is no particular limitation on the iodine value of the ester compound (A3).

[0029] The weight average molecular weight of the ester compound (A3) is not particularly limited, but is preferably 150 to 1000 from the viewpoints of smoothness and low fuming. The upper limit of the average molecular weight is more preferably 800, and still more preferably 700. On the other hand, the lower limit of the average molecular weight is more preferably 300, and still more preferably 500. Further, for example, 300 to 800 is more preferred, and 500 to 700 is still more preferred.

[0030] The ester compound (A3) can generally be synthesized and obtained by a known method using commercially available aliphatic monohydric alcohols and aliphatic polycarboxylic acids.

[0031] 4) Aromatic ester compounds (A4) Aromatic ester compounds (A4) are ester compounds having at least one aromatic ring in their molecule. Specifically, examples include ester compounds (A4-1) having a structure in which an aromatic carboxylic acid and an alcohol are ester-bonded, and ester compounds (A4-2) having a structure in which an aromatic alcohol and a carboxylic acid are ester-bonded. Furthermore, aromatic ester compounds (A4) are compounds that do not have a polyoxyalkylene group in their molecule. One or more aromatic ester compounds (A4) can be used.

[0032] The aromatic carboxylic acid constituting the ester compound (A4-1) may be a monocarboxylic acid or a polycarboxylic acid. One or more types may be used. Examples of aromatic carboxylic acids include benzoic acid, toluic acid, naphthoic acid, phthalic acid, isophthalic acid, terephthalic acid, salicylic acid, gallic acid, melitic acid, cinnamic acid, trimellitic acid, and pyromellitic acid. Among these, trimellitic acid, phthalic acid, isophthalic acid, and terephthalic acid are preferred, with trimellitic acid being even more preferred.

[0033] The alcohol constituting the ester compound (A4-1) may be a monohydric alcohol or a polyhydric alcohol. It may also be an aliphatic alcohol, an alicyclic alcohol, or an aromatic alcohol. One or more monohydric alcohols can be used. Among these, monohydric alcohols are preferred, and aliphatic monohydric alcohols are even more preferred.

[0034] Examples of monohydric alcohols include alkylbenzene alcohols, dialkylbenzene alcohols, octyl alcohol, isooctyl alcohol, lauryl alcohol, myristyl alcohol, myristrail alcohol, cetyl alcohol, isocetyl alcohol, palmitrail alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, baxenyl alcohol, gadleyl alcohol, arachidyl alcohol, isoicosanyl alcohol, eicosenoyl alcohol, behenyl alcohol, isodocosanyl alcohol, erukanyl alcohol, lignocerinyl alcohol, isotetracosanyl alcohol, nerbonyl alcohol, cerothinyl alcohol, montanyl alcohol, and merisinyl alcohol. Examples of polyhydric alcohols include aliphatic polyhydric alcohols as described in ester compounds (A2) and aromatic polyhydric alcohols as described in ester compounds (A4-2).

[0035] The aromatic alcohol constituting the ester compound (A4-2) can be one or more types. Aromatic polyhydric alcohols are preferred, and aromatic trihydric alcohols are more preferred. Examples of aromatic alcohols include aromatic monohydric alcohols such as alkylbenzene alcohols, dialkylbenzene alcohols, and aromatic polyhydric alcohols such as bisphenol A, bisphenol Z, and 1,3,5-trihydroxymethylbenzene. Among these, bisphenol A, bisphenol Z, and 1,3,5-trihydroxymethylbenzene are preferred, and 1,3,5-trihydroxymethylbenzene is more preferred.

[0036] The carboxylic acid constituting the ester compound (A4-2) may be either an aliphatic carboxylic acid or an aromatic carboxylic acid. It may also be either a monohydric carboxylic acid or a polyhydric carboxylic acid. One or more types may be used. Among these, monohydric carboxylic acids are preferred, and fatty acids are even more preferred. Fatty acids are preferably saturated from the viewpoint of persistence. Fatty acids may be linear or branched.

[0037] Examples of monovalent carboxylic acids include alkylbenzene carboxylic acids, dialkylbenzene carboxylic acids, butyric acid, crotonic acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, lauric acid, myristic acid, myristoleic acid, pentadecylic acid, palmitic acid, palmitoleic acid, isocetyl acid, margaric acid, stearic acid, isostearic acid, oleic acid, elaidic acid, vaccenic acid, linoleic acid, linolenic acid, tubercurostearic acid, arachidic acid, isoeicosanoic acid, gadoleic acid, eicosenoic acid, behenic acid, isodocosanoic acid, erucic acid, lignoceric acid, isotetracosanoic acid, nervonic acid, cerotic acid, montanic acid, and melissic acid. Examples of polyvalent carboxylic acids include aliphatic polyvalent carboxylic acids as described in ester compounds (A3) and aromatic polyvalent carboxylic acids as described in ester compounds (A4-1).

[0038] 5) Sulfur-containing ester compound (A5) The sulfur-containing ester compound is not particularly limited, but is preferably at least one selected from diester compounds of thiodipropionic acid and aliphatic alcohol and monoester compounds of thiodipropionic acid and aliphatic alcohol. The sulfur-containing ester compound is a component that has antioxidant ability. By using the sulfur-containing ester compound, the heat resistance of the treatment agent can be increased. One or more sulfur-containing ester compounds can be used. The weight-average molecular weight of the sulfur-containing ester compound is not particularly limited, but is preferably 400 to 1000 in terms of smoothness and low smoke generation. The upper limit of the molecular weight is more preferably 900 and even more preferably 800. On the other hand, the lower limit of the molecular weight is more preferably 500 and even more preferably 600. Also, for example, is more preferably 500 to 900 and even more preferably 600 to 800. The aliphatic alcohol constituting the sulfur-containing ester compound may be saturated or unsaturated. Furthermore, the aliphatic alcohol may have a linear or branched structure, but a branched structure is preferred. The number of carbon atoms in the aliphatic alcohol is preferably 8 to 24, more preferably 12 to 24, and even more preferably 16 to 24. Examples of aliphatic alcohols include octyl alcohol, 2-ethylhexyl alcohol, decyl alcohol, lauryl alcohol, myristyl alcohol, isocetyl alcohol, oleyl alcohol, and isostearyl alcohol, among which oleyl alcohol and isostearyl alcohol are preferred. The sulfur-containing ester compound may be a mixture of a diester compound of thiodipropionic acid and an aliphatic alcohol (simply referred to as a diester in this paragraph) and a monoester compound of thiodipropionic acid and an aliphatic alcohol (simply referred to as a monoester in this paragraph). In this case, the weight ratio of the diester to the monoester is preferably 100 / 0 to 70 / 30 in terms of smoothness and low smoke generation. The upper limit of the weight ratio is more preferably 99.5 / 0.5, and even more preferably 99 / 1. On the other hand, the lower limit of the weight ratio is more preferably 75 / 25, and even more preferably 80 / 20. Also, for example, 100 / 0 to 75 / 25 is more preferably, and 100 / 0 to 80 / 20 is even more preferably.

[0039] 6) Ester compounds having a polyoxyalkylene group (A6) There are no particular limitations on the ester compounds having a polyoxyalkylene group (A6) as long as they are compounds having an ester bond with a polyoxyalkylene group. Examples include polyoxyalkylene group-containing hydroxy fatty acid polyhydric alcohol esters (hereinafter sometimes referred to as polyhydroxy esters), esters in which at least one hydroxyl group of a polyhydroxy ester is encapsulated with a fatty acid, polyoxyalkylene polyhydric alcohol fatty acid esters, polyoxyalkylene aliphatic monohydric alcohol fatty acid esters, fatty acid esters of polyoxyalkylene glycols, etc., and one or more of these can be used.

[0040] (Polyhydroxyesters, esters in which at least one hydroxyl group of a polyhydroxyester is encapsulated with a fatty acid) Structurally, polyhydroxyesters are esters of a polyoxyalkylene group-containing hydroxy fatty acid and a polyhydric alcohol, and it is preferable that two or more hydroxyl groups of the polyhydric alcohol are esterified. Therefore, polyoxyalkylene group-containing hydroxy fatty acid polyhydric alcohol esters are esters having multiple hydroxyl groups.

[0041] Polyoxyalkylene group-containing hydroxy fatty acids have a structure in which a polyoxyalkylene group is bonded to the hydrocarbon group of a fatty acid via an oxygen atom, with the end of the polyoxyalkylene group that is not bonded to the hydrocarbon group of the fatty acid being a hydroxyl group. Examples of polyhydroxy esters include alkylene oxide adducts of esterified hydroxy fatty acids having 6 to 22 carbon atoms (preferably 16 to 20 carbon atoms) and polyhydric alcohols.

[0042] Examples of hydroxy fatty acids having 6 to 22 carbon atoms include hydroxycaprylic acid, hydroxycapric acid, hydroxylauric acid, hydroxystearic acid, and ricinoleic acid, with hydroxyoctadecanoic acid and ricinoleic acid being preferred. Examples of polyhydric alcohols include ethylene glycol, glycerin, sorbitol, sorbitan, trimethylolpropane, and pentaerythritol, with glycerin being preferred. Examples of alkylene oxides include alkylene oxides having 2 to 4 carbon atoms, such as ethylene oxide, propylene oxide, and butylene oxide.

[0043] The number of moles of alkylene oxide to be added is not particularly limited, but 3 to 60 moles is preferred. The upper limit of this number of moles is more preferably 50 moles, and even more preferably 45 moles. On the other hand, the lower limit of this number of moles is more preferably 8 moles, and even more preferably 10 moles. Also, for example, 8 to 50 moles is preferred. The proportion of ethylene oxide in the alkylene oxide is preferably 50 mol% or more, and even more preferably 80 mol% or more. When adding two or more types of alkylene oxide, the order of their addition is not particularly limited, and the addition form may be block-shaped or random. The addition of alkylene oxide can be carried out by known methods, but it is generally carried out in the presence of a basic catalyst.

[0044] Polyhydroxyesters can be produced, for example, by esterifying a polyhydric alcohol with a hydroxy fatty acid (hydroxy monocarboxylic acid) under normal conditions to obtain an esterified product, and then adding an alkylene oxide to this esterified product. Polyhydroxyesters can also be suitably produced by using naturally obtained oils and fats such as castor oil, or hydrogenated castor oil obtained by adding hydrogen to castor oil, and then adding an alkylene oxide to these products.

[0045] The ester compounds (A6) having polyoxyalkylene groups also include esters in which at least one hydroxyl group of the above-mentioned polyhydroxy ester is encapsulated with a fatty acid. The number of carbon atoms in the fatty acid to be encapsulated is preferably 6 to 24, and more preferably 12 to 18. The number of carbon atoms in the hydrocarbon group in the fatty acid may be distributed, the hydrocarbon group may be linear or branched, saturated or unsaturated, and may have a polycyclic structure. Examples of such fatty acids include lauric acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, eicosanoic acid, behenic acid, and lignoceric acid. There are no particular limitations on the esterification method or reaction conditions, and known methods and ordinary conditions can be used.

[0046] Examples of polyhydroxyesters and esters in which at least one hydroxyl group of a polyhydroxyester is sequestered with a fatty acid include hydrogenated castor oil ethylene oxide adduct, castor oil ethylene oxide adduct, hydrogenated castor oil ethylene oxide adduct monooleate, hydrogenated castor oil ethylene oxide adduct dioleate, hydrogenated castor oil ethylene oxide adduct trioleate, castor oil ethylene oxide adduct trioleate, hydrogenated castor oil ethylene oxide adduct tristearate, and among these, hydrogenated castor oil ethylene oxide adduct, hydrogenated castor oil ethylene oxide adduct trioleate, and hydrogenated castor oil ethylene oxide adduct tristearate are preferred in terms of compatibility with the treatment agent, oil film strength, and reduction of fluff.

[0047] (Polyoxyalkylene polyhydric alcohol fatty acid esters) Polyoxyalkylene polyhydric alcohol fatty acid esters are compounds having a structure in which a compound in which an alkylene oxide such as ethylene oxide, propylene oxide, or butylene oxide is added to a polyhydric alcohol is esterified with a fatty acid. Examples of polyhydric alcohols include glycerin, trimethylolpropane, pentaerythritol, erythritol, diglycerin, sorbitan, sorbitol, ditrimethylolpropane, dipentaerythritol, and sucrose. Among these, glycerin, diglycerin, sorbitan, and sorbitol are preferred.

[0048] Examples of fatty acids include octyl acid, lauric acid, capric acid, myristic acid, myristoleic acid, palmitic acid, palmitoleic acid, isocetyl acid, stearic acid, isostearic acid, oleic acid, elaidic acid, linoleic acid, linolenic acid, arachidic acid, eicosenoic acid, behenic acid, isodocosanoic acid, erucic acid, lignoceric acid, and isotetracosanoic acid.

[0049] There are no particular limitations on the number of moles of alkylene oxide to be added, but 3 to 100 moles is preferred in terms of emulsification. The upper limit of the number of moles to be added is more preferably 70 moles, and even more preferably 50 moles. On the other hand, the lower limit of the number of moles to be added is more preferably 5 moles, and even more preferably 7 moles. Also, for example, 5 to 70 moles is more preferred, and even more preferably 10 to 50 moles. Furthermore, the proportion of ethylene oxide in the alkylene oxide is preferably 50 mol% or more, and even more preferably 80 mol% or more. There are no particular limitations on the weight-average molecular weight of the polyoxyalkylene polyhydric alcohol fatty acid ester, but for example, 300 to 7000 is preferred. The upper limit of the average molecular weight is more preferably 5000, and even more preferably 3000. On the other hand, the lower limit of the average molecular weight is more preferably 500, and even more preferably 700. Also, for example, 500 to 5000 is more preferred, and even more preferably 700 to 3000.

[0050] Examples of polyoxyalkylene polyhydric alcohol fatty acid esters include, but are not limited to, glycerol ethylene oxide adduct monolaurate, glycerol ethylene oxide adduct dilaurate, glycerol ethylene oxide adduct trilaurate, trimethylolpropane ethylene oxide adduct trilaurate, sorbitan ethylene oxide adduct monooleate, sorbitan ethylene oxide adduct dioleate, sorbitan ethylene oxide adduct trioleate, sorbitan ethylene oxide propylene oxide adduct monooleate, sorbitan ethylene oxide propylene oxide adduct dioleate, sorbitan ethylene oxide propylene oxide adduct trioleate, sorbitan ethylene oxide propylene oxide adduct trilaurate, sucrose ethylene oxide adduct trilaurate, etc.

[0051] (Polyoxyalkylene aliphatic monohydric alcohol fatty acid esters) Polyoxyalkylene aliphatic monohydric alcohol fatty acid esters are compounds in which a fatty acid is esterified to a compound in which an alkylene oxide such as ethylene oxide, propylene oxide, or butylene oxide is added to an aliphatic monohydric alcohol.

[0052] Examples of aliphatic monohydric alcohols include octyl alcohol, isooctyl alcohol, decyl alcohol, isodecyl alcohol, lauryl alcohol, myristyl alcohol, myristrail alcohol, cetyl alcohol, isocetyl alcohol, palmitrail alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, baxenyl alcohol, gadleyl alcohol, arachidyl alcohol, isoicosanyl alcohol, eicosenoyl alcohol, behenyl alcohol, isodocosanyl alcohol, erukanyl alcohol, lignocerinyl alcohol, isotetracosanyl alcohol, nerbonyl alcohol, cerotinyl alcohol, montanyl alcohol, and merisinyl alcohol. Among these, octyl alcohol, isooctyl alcohol, decyl alcohol, isodecyl alcohol, lauryl alcohol, myristyl alcohol, myristrail alcohol, cetyl alcohol, isocetyl alcohol, palmitrail alcohol, stearyl alcohol, isostearyl alcohol, and oleyl alcohol are preferred.

[0053] Examples of fatty acids include octyl acid, capric acid, lauric acid, myristic acid, myristoleic acid, palmitic acid, palmitoleic acid, isocetyl acid, stearic acid, isostearic acid, oleic acid, elaidic acid, linoleic acid, linolenic acid, arachidic acid, eicosenoic acid, behenic acid, isodocosanoic acid, erucic acid, lignoceric acid, and isotetracosanoic acid.

[0054] There are no particular limitations on the number of moles of alkylene oxide to be added, but 3 to 100 moles is preferred in terms of emulsification. The upper limit of the number of moles to be added is more preferably 70 moles, and even more preferably 50 moles. On the other hand, the lower limit of the number of moles to be added is more preferably 5 moles, and even more preferably 7 moles. Also, for example, 5 to 70 moles is more preferably, and even more preferably 7 to 50 moles. Furthermore, the proportion of ethylene oxide in the alkylene oxide is preferably 10 mol% or more, and even more preferably 20 mol% or more.

[0055] The weight-average molecular weight of the polyoxyalkylene aliphatic monohydric alcohol fatty acid ester is not particularly limited, but is preferably 300 to 7000. The upper limit of the average molecular weight is more preferably 5000, and even more preferably 3000. On the other hand, the lower limit of the average molecular weight is more preferably 400, and even more preferably 450. Also, for example, is more preferably 400 to 5000, and even more preferably 450 to 3000.

[0056] Examples of polyoxyalkylene aliphatic monohydric alcohol fatty acid esters include, but are not limited to, octanoate (octyl alcohol ethylene oxide adduct), laurate (octyl alcohol ethylene oxide adduct), octanoate (lauryl alcohol ethylene oxide adduct), caprylate (lauryl alcohol ethylene oxide adduct), laurate (lauryl alcohol ethylene oxide adduct), caprylate (lauryl alcohol propylene oxide adduct), laurate (lauryl alcohol propylene oxide adduct), caprylate (lauryl alcohol ethylene oxide propylene oxide adduct), and laurate (lauryl alcohol ethylene oxide propylene oxide adduct).

[0057] (Compounds with a structure in which polyoxyalkylene glycol and a fatty acid are ester-bonded) Compounds with a structure in which polyoxyalkylene glycol and a fatty acid are ester-bonded include compounds having a structure in which polyoxyethylene glycol or polyoxyethylene polyoxypropylene glycol and a fatty acid are ester-bonded. The weight-average molecular weight of polyoxyalkylene glycol is not particularly limited, but for example, 100 to 1500 is preferred. The upper limit of the average molecular weight is more preferably 1400, and even more preferably 1200. On the other hand, the lower limit of the average molecular weight is more preferably 150, and even more preferably 200. Also, for example, 150 to 1400 is more preferred, and even more preferably 200 to 1200.

[0058] Examples of compounds having a structure in which polyoxyalkylene glycol and a fatty acid are ester-bonded include, but are not limited to, polyethylene glycol monolaurate, polyethylene glycol dilaurate, polyethylene glycol monooleate, polyethylene glycol dioleate, polyethylene glycol monostearate, polyethylene glycol distearate, polyethylene polypropylene glycol monolaurate, polyethylene polypropylene glycol dilaurate, polyethylene polypropylene glycol monooleate, and polyethylene polypropylene glycol dioleate.

[0059] The ester component (A) comprises at least one selected from the ester compound represented by the general formula (1) above and a compound having a structure in which polyoxyalkylene glycol and a fatty acid are ester-bonded. The inclusion of a compound having a structure in which polyoxyalkylene glycol and a fatty acid are ester-bonded is more preferable in terms of smoothness, heat resistance, and emulsification. As for the ester component (A), it is preferable to use one that has been purified by removing catalysts, etc., from the viewpoint of improving heat resistance and obtaining a clear treatment agent.

[0060] [Nonionic surfactant (B) having a polyoxyalkylene skeleton without ester bonds] The treatment agent of the present invention contains a nonionic surfactant (B) having a polyoxyalkylene skeleton without ester bonds (hereinafter sometimes simply referred to as nonionic surfactant (B)). Examples of nonionic surfactant (B) include polyoxyalkylene polyhydric alcohol ethers and polyoxyalkylene aliphatic alcohol ethers. Nonionic surfactant (B) includes a nonionic surfactant (B1) having an alkyl group having 12 to 15 carbon atoms, and is preferable in terms of smoothness and heat resistance if it includes a polyoxyalkylene aliphatic alcohol ether having an alkyl group having 12 to 15 carbon atoms. Nonionic surfactant (B) is preferable if it includes a polyoxyalkylene polyhydric alcohol ether, and is preferable in terms of oil film strength and flocculation if it includes polyoxyalkylene glycol (B2).

[0061] (Polyoxyalkylene polyhydric alcohol ethers) Polyoxyalkylene polyhydric alcohol ethers are compounds having a structure in which an alkylene oxide such as ethylene oxide, propylene oxide, or butylene oxide is added to a polyhydric alcohol. Examples of polyhydric alcohols include ethylene glycol, propylene glycol, glycerin, trimethylolpropane, pentaerythritol, diglycerin, sorbitan, sorbitol, ditrimethylolpropane, dipentaerythritol, and sucrose. Among these, glycerin, trimethylolpropane, and sucrose are preferred.

[0062] There are no particular limitations on the number of moles of alkylene oxide to be added, but 3 to 100 moles are preferred in terms of emulsification. The upper limit of the number of moles to be added is more preferably 70 moles, and even more preferably 50 moles. On the other hand, the lower limit of the number of moles to be added is more preferably 4 moles, and even more preferably 5 moles. For example, 4 to 70 moles are more preferred, and even more preferably 5 to 50 moles. The proportion of ethylene oxide in the alkylene oxide is preferably 10 mol% or more, and even more preferably 50 mol% or more. There are no particular limitations on the weight-average molecular weight of the polyoxyalkylene polyhydric alcohol ether, but 150 to 10000 are preferred in terms of emulsification and oil film strength. The upper limit of the average molecular weight is more preferably 8000, and even more preferably 5000. On the other hand, the lower limit of the average molecular weight is more preferably 300, and even more preferably 450. For example, 300 to 8000 are more preferred, and even more preferably 450 to 5000.

[0063] Examples of polyoxyalkylene polyhydric alcohol ethers include, but are not limited to, polyoxyalkylene glycols (B2) such as polyethylene glycol and polypropylene glycol, glycerin ethylene oxide adducts, trimethylolpropane ethylene oxide adducts, pentaerythritol ethylene oxide adducts, diglycerin ethylene oxide adducts, sorbitan ethylene oxide adducts, sorbitan ethylene oxide propylene oxide adducts, sorbitol ethylene oxide adducts, sorbitol ethylene oxide propylene oxide adducts, sorbitol propylene oxide adducts, ditrimethylolpropane ethylene oxide adducts, dipentaerythritol ethylene oxide adducts, sucrose ethylene oxide adducts, and sucrose propylene oxide adducts.

[0064] As the polyoxyalkylene glycol (B2), polyethylene glycol, polypropylene glycol, and polyoxyethylene polyoxypropylene glycol are preferred, with polyoxyethylene polyoxypropylene glycol being more preferred.

[0065] (Polyoxyalkylene aliphatic alcohol ethers) Polyoxyalkylene aliphatic alcohol ethers are compounds that have a structure in which an alkylene oxide such as ethylene oxide, propylene oxide, or butylene oxide is added to an aliphatic monohydric alcohol. Examples of polyoxyalkylene aliphatic alcohol ethers include alkylene oxide adducts of aliphatic alcohols such as octyl alcohol, 2-ethylhexyl alcohol, decyl alcohol, isodecyl alcohol, lauryl alcohol, tridecyl alcohol, myristyl alcohol, stearyl alcohol, isostearyl alcohol, and oleyl alcohol.

[0066] There are no particular limitations on the number of moles of alkylene oxide to be added, but 1 to 100 moles is preferred. The upper limit of the number of moles to be added is more preferably 70 moles, and even more preferably 50 moles. On the other hand, the lower limit of the number of moles to be added is more preferably 2 moles, and even more preferably 3 moles. Also, for example, 2 to 70 moles is more preferred, and even more preferably 3 to 50 moles. Furthermore, the ratio of ethylene oxide to the total alkylene oxide is preferably 20 mol% or more, more preferably 30 mol% or more, and even more preferably 40 mol% or more.

[0067] [Other Surfactants (C)] The treatment agent of the present invention may further contain other surfactants (C) in addition to the above-mentioned ester component (A) and nonionic surfactant (B) having a polyoxyalkylene skeleton without ester bonds, in order to impart oil film strength and cohesiveness to the raw yarn and improve spinnability. Examples of other surfactants (C) include anionic surfactants (C1), cationic surfactants, amphoteric surfactants, etc., and there are no particular limitations as long as they are surfactants other than the above-mentioned ester component (A) and nonionic surfactant (B) having a polyoxyalkylene skeleton without ester bonds. One or more types of other surfactants (C) may be used.

[0068] [Anionic surfactant (C1)] There are no particular limitations on the anionic surfactant (C1), but examples include anionic surfactants containing a sulfur element (C1-1), organophosphate ester compounds (C1-2), fatty acid soaps (C1-3), etc. However, in terms of antistatic properties and emulsifying properties, anionic surfactants containing a sulfur element (C1-1), organophosphate ester compounds (C1-2), and fatty acid soaps (C1-3) are preferred.

[0069] [Anionic surfactants containing sulfur (C1-1)] There are no particular limitations on the anionic surfactants containing sulfur, but organic sulfonates and organic sulfate ester salts are preferably used, and more specifically, alkane sulfonate metal salts and dioctyl sulfosuccinate metal salts are examples. Anionic surfactants containing sulfur often contain sodium sulfate and / or sodium chloride due to their manufacturing method. The ratio of sodium sulfate and sodium chloride contained in these raw materials can be calculated from the weight percentage of sulfate ions and chloride ions detected from the raw materials by ion chromatography. It is preferable to use raw materials in which the weight percentage of sulfate ions detected by ion chromatography is 5000 ppm or less and the weight percentage of chloride ions is 5000 ppm or less relative to the total amount of anionic surfactants containing sulfur.

[0070] [Organophosphate ester compounds (C1-2)] There are no particular limitations on the organic phosphate ester compounds, but they contain one or more hydrocarbon groups with 6 to 24 carbon atoms in their structure, and the organic phosphate portion may be mono, di, poly, etc. They may also contain inorganic phosphate. They may also contain alkylene oxy groups in their structure and may form metal salts or organic amine salts.

[0071] [Fatty Acid Soap (C1-3)] There are no particular limitations on fatty acid soaps, but examples include metal salts of fatty acids having 6 to 24 carbon atoms.

[0072] [Cationic surfactants] Cationic surfactants are not particularly limited, but examples include alkylamine salts, alkylimidazolinium salts, and quaternary ammonium salts.

[0073] [Amphoteric surfactants] There are no particular limitations on amphoteric surfactants, but examples include lauryldimethylbetaine, stearyldimethylbetaine, and dimethyllaurylamine oxide.

[0074] [Other Components (D)] The treatment agent of the present invention may contain other components (D) in addition to the above-mentioned ester component (A), nonionic surfactant (B) having a polyoxyalkylene skeleton without ester bonds, and other surfactants (C), in order to improve the heat resistance and spinnability of the raw yarn. Examples of other components (D) include antioxidants, silicone compounds, and mineral oils that are non-volatile at room temperature (machine oil, spindle oil, liquid paraffin, etc.). There are no particular limitations as long as the components are other than the above-mentioned ester component (A), nonionic surfactant (B) having a polyoxyalkylene skeleton without ester bonds, and other surfactants (C), but it is preferable to include a silicone compound in terms of smoothness and heat resistance.

[0075] Examples of silicone compounds include dimethyl silicone and modified silicone. Examples of modified silicones include polyether-modified silicone, alkyl-modified silicone, fatty acid ester-modified silicone, and phenyl-modified silicone, with polyether-modified silicone being particularly preferred. The proportion of the silicone compound in the nonvolatile content of the treatment agent is not particularly limited, but 0.05 to 1.5% by weight is preferred in terms of the stability of the treatment agent and the reduction of thermal degradation products. The upper limit of this proportion is more preferably 1.3% by weight, even more preferably 1.1% by weight, and particularly preferably 0.9% by weight. On the other hand, the lower limit of this proportion is more preferably 0.1% by weight, even more preferably 0.2% by weight, and particularly preferably 0.4% by weight. Also, for example, 0.1 to 1.3% by weight is more preferred, 0.2 to 1.1% by weight is even more preferred, and 0.4 to 0.9% by weight is particularly preferred. One or more types of other components (D) may be used.

[0076] [Treatment Agent for Synthetic Fibers] The first embodiment of the present invention provides a treatment agent for synthetic fibers containing an ester component (A) and a nonionic surfactant (B) having a polyoxyalkylene skeleton without ester bonds, wherein the ester component (A) includes at least one selected from ester compounds represented by the following general formula (1) and compounds having a structure in which polyoxyalkylene glycol and a fatty acid are ester-bonded, and the nonionic surfactant (B) includes a nonionic surfactant (B1) having an alkyl group having 12 to 15 carbon atoms, the proportion of the nonionic surfactant (B) in the nonvolatile content of the treatment agent is within a specific range, and the strong acid value and saponification value of the nonvolatile content of the treatment agent are within a specific range, and by satisfying the following conditions 1 and 2, it is possible to achieve both a reduction in the amount of thermally degraded material and suppression of tension fluctuations. The reason why it is possible to achieve both a reduction in the amount of thermally degraded material and suppression of tension fluctuations is not particularly limited, but we believe that by satisfying condition 1, the treatment agent remains even after a short period of high-temperature thermal history during the manufacturing process, so that the fiber bundles can maintain lubricity and cohesiveness, preventing yarn abrasion, fuzzing, and breakage. Furthermore, by satisfying condition 2, the amount of thermally degraded material is reduced because the treatment agent decomposes and volatilizes in an appropriate amount when subjected to a long period of thermal history, and in addition, the treatment agent contains few components that tend to harden into tar due to thermal history.

[0077] The proportion of ester component (A) in the non-volatile content of the treatment agent is not particularly limited, but 1 to 24% by weight is preferred in terms of suppressing tension fluctuations and reducing the amount of thermally degraded material. The upper limit of this proportion is more preferably 20% by weight, even more preferably 15% by weight, and particularly preferably 10% by weight. On the other hand, the lower limit of this proportion is more preferably 2% by weight, even more preferably 3% by weight, and particularly preferably 4% by weight. Also, for example, 2 to 20% by weight is more preferably, even more preferably 3 to 15% by weight, and particularly preferably 4 to 10% by weight.

[0078] The proportion of nonionic surfactant (B) having a polyoxyalkylene skeleton without ester bonds in the nonvolatile components of the treatment agent is 40 to 97% by weight. This range is advantageous in suppressing tension fluctuations and reducing the amount of thermally degraded materials. The upper limit of this proportion is more preferably 96% by weight, even more preferably 95% by weight, and particularly preferably 94% by weight. On the other hand, the lower limit of this proportion is more preferably 50% by weight, even more preferably 60% by weight, and particularly preferably 85% by weight. For example, 50 to 96% by weight is more preferable, and 60 to 95% by weight is even more preferable.

[0079] The proportion of the nonionic surfactant (B1) having an alkyl group with 12 to 15 carbon atoms in the nonvolatile content of the treatment agent is not particularly limited, but 50 to 95% by weight is preferred in terms of suppressing tension fluctuations and reducing the amount of thermally degraded products. The upper limit of this proportion is more preferably 90% by weight, even more preferably 85% by weight, and particularly preferably 80% by weight. On the other hand, the lower limit of this proportion is more preferably 52% by weight, even more preferably 55% by weight, and particularly preferably 60% by weight. For example, 52 to 90% by weight is more preferred, and 55 to 85% by weight is even more preferred.

[0080] The proportion of polyoxyalkylene glycol (B2) in the nonvolatile components of the treatment agent is not particularly limited, but 5 to 50% by weight is preferred in terms of suppressing tension fluctuations and reducing the amount of thermally degraded materials. The upper limit of this proportion is more preferably 45% by weight, even more preferably 40% by weight, and particularly preferably 35% by weight. On the other hand, the lower limit of this proportion is more preferably 8% by weight, even more preferably 10% by weight, and particularly preferably 15% by weight. For example, 8 to 45% by weight is more preferred, and 10 to 40% by weight is even more preferred.

[0081] The total proportion of the ester component (A) and the nonionic surfactant (B) having a polyoxyalkylene skeleton without ester bonds in the nonvolatile content of the treatment agent is not particularly limited, but is preferably 45 to 99.9% by weight in terms of reducing the amount of thermally degraded products, suppressing tension fluctuations, and more easily satisfying conditions 1 and 2 of the present invention. The upper limit of this weight percentage is more preferably 99% by weight, even more preferably 98% by weight, and particularly preferably 97% by weight. On the other hand, the lower limit of this weight percentage is more preferably 80% by weight, even more preferably 90% by weight, and particularly preferably 95% by weight. Also, for example, 80 to 99% by weight is more preferably, and 90 to 98% by weight is even more preferably.

[0082] The weight percentage of the anionic surfactant (C1) in the nonvolatile content of the treatment agent is not particularly limited, but 0 to 5% by weight is preferred in terms of reducing the amount of thermally degraded products. The upper limit of this weight percentage is more preferably 3% by weight, even more preferably 2% by weight, and particularly preferably 1% by weight.

[0083] The iodine value of the non-volatile components of the treatment agent of the present invention is not particularly limited, but is preferably 0 to 8.6 in terms of heat resistance and in terms of more easily satisfying conditions 1 and 2 of the present invention. In terms of suppressing tension fluctuations and reducing the amount of thermally degraded material, the upper limit of the iodine value is more preferably 7, even more preferably 6, particularly preferably 5, and most preferably 4. On the other hand, the lower limit of the iodine value is more preferably 0.1, even more preferably 1, and particularly preferably 2. Also, for example, 0.1 to 6 is more preferably, and 1 to 5 is even more preferably. In this invention, the non-volatile content of the treatment agent refers to the components on the aluminum sheet when 2.0 to 3.0 g of the treatment agent is spread flat on the aluminum sheet, dried at 110°C under infrared lamp irradiation, and the fluctuation range of the volatile content over 150 seconds becomes 0.15%, or the oven-dried components when the treatment agent is extracted from synthetic fibers using an extraction solvent in which the treatment agent dissolves (water, methanol, ethanol, isopropanol, methyl ethyl ketone, hexane, cyclohexane, etc.), heat-treated at 110°C to remove the extraction solvent, and a constant weight is reached. Furthermore, in this invention, the iodine value is a value measured in accordance with JIS K-0070-1992. The iodine value can be adjusted by adjusting the content of raw materials that contain many double and triple bonds.

[0084] The strong acid value of the non-volatile component of the treatment agent of the present invention is 0.00 to 0.10 mg KOH / g. By keeping this strong acid value within a predetermined range, both high-temperature stability and heat resistance can be achieved. The upper limit of the strong acid value is preferably 0.08 mg KOH / g, more preferably 0.06 mg KOH / g, and even more preferably 0.04 mg KOH / g. On the other hand, the lower limit of the strong acid value is preferably 0.01 mg KOH / g. The strong acid value in the present invention is determined by the method described in the examples. The strong acid value is high when a strongly acidic component (for example, p-toluenesulfonic acid, a catalyst used in the esterification reaction) is present. The value can be lowered by removing the strongly acidic component through purification treatments such as water washing or adsorbent filtration. In addition, the strong acid value can be lowered by not using strongly acidic components, such as by performing the esterification reaction without a catalyst.

[0085] The saponification value of the nonvolatile components of the treatment agent of the present invention is 2 to 20 mg KOH / g. In terms of smoothness, suppression of tension fluctuations, reduction of the amount of thermally degraded material, and ease of satisfying conditions 1 and 2 of the present invention, the upper limit of the saponification value is preferably 18 mg KOH / g, more preferably 14 mg KOH / g, and even more preferably 10.5 mg KOH / g. On the other hand, the lower limit of the saponification value is preferably 2.2 mg KOH / g, more preferably 2.5 mg KOH / g, and even more preferably 2.8 mg KOH / g. Also, for example, 2.2 to 18 mg KOH / g is preferred, 2.5 to 14 mg KOH / g is more preferred, and 2.8 to 10.5 mg KOH / g is particularly preferred.

[0086] The treatment agent of the present invention satisfies the following conditions 1 and 2. Condition 1: The residual rate after heating 0.5 g of the nonvolatile content of the treatment agent at 200°C for 1 hour is 10 to 30% by weight. Condition 2: The residual rate after heating 0.5 g of the nonvolatile content of the treatment agent at 200°C for 24 hours is greater than 0 to 6% by weight. Conditions 1 and 2 require measuring the residual rate using the above sample weight, heating temperature, and time. For example, even if the difference in residual rate is clear under condition 1 or 2, if the amount of nonvolatile content heated is 5 g, the volatilization due to thermal decomposition will be significantly slower, and polymerization will proceed in the center of the treatment agent solution, resulting in a higher residual rate and making the difference in residual rate unclear. Also, if the heating temperature is 215°C, the volatilization rate due to thermal decomposition is extremely fast, making the difference in residual rate unclear. For Condition 1, the remaining percentage after heating at 200°C for 1 hour is preferably 28% by weight or less, more preferably 26% by weight or less, similarly preferably 12% by weight or more, and more preferably 14% by weight or more, in terms of smoothness and suppression of tension fluctuations. Also, for example, 12 to 28% by weight is preferred, and 14 to 26% by weight is more preferred. For Condition 2, the remaining percentage after heating at 200°C for 24 hours is preferably 5.5% by weight or less, more preferably 5% by weight or less, similarly preferably 0.5% by weight or more, and more preferably 1.5% by weight or more, in terms of suppression of tension fluctuations and reduction of the amount of thermally degraded material. Also, for example, 0.5 to 5.5% by weight is preferred, and 1.5 to 5% by weight is more preferred. The measurement methods for Condition 1 and Condition 2 are as described in the examples.

[0087] The total content of Zr and Ti elements detected from the non-volatile components of the treatment agent by ICP emission spectrometry is not particularly limited, but is preferably 0 to 54 ppm or less in terms of high-temperature stability, suppression of tension fluctuations and reduction of thermal degradation, and in terms of more easily satisfying condition 2 of the present invention. The upper limit of the content is more preferably 30 ppm, even more preferably 25 ppm, and particularly preferably 20 ppm. On the other hand, the lower limit of the content is more preferably 0.1 ppm, even more preferably 1 ppm. Also, for example, 0 to 30 ppm is more preferably, 0.1 to 25 ppm is even more preferably, and 1 to 20 ppm is particularly preferably. The method for measuring the content is as described in the examples.

[0088] The total content of K and Na elements detected from the non-volatile matter of the treatment agent by ICP emission spectrometry is not particularly limited, but is preferably 50 to 2000 ppm in terms of heat resistance and ease of satisfying conditions 1 and 2 of the present invention. The upper limit of the content is more preferably 1500 ppm, and even more preferably 1000 ppm. On the other hand, the lower limit of the content is preferably 100 ppm, more preferably 200 ppm, and even more preferably 400 ppm. Also, for example, 200 to 1500 ppm is more preferably, and even more preferably 400 to 1000 ppm. The method for measuring the content is as described in the examples.

[0089] The total Si content of the treatment agent detected from the non-volatile components of the treatment agent by ICP emission spectrometry is not particularly limited, but is preferably 50 to 2000 ppm in terms of high-temperature stability and heat resistance, and in terms of easily satisfying conditions 1 and 2 of the present invention. The upper limit of the content is more preferably 1800 ppm, and even more preferably 1600 ppm. On the other hand, the lower limit of the content is preferably 200 ppm, more preferably 250 ppm, and even more preferably 300 ppm. Also, for example, 250 to 1800 ppm is more preferably, and even more preferably 300 to 1600 ppm. The method for measuring the content is as described in the examples.

[0090] Furthermore, the synthetic fiber treatment agent of the present invention may further contain a stock stabilizer (for example, water, ethylene glycol, or propylene glycol). The weight percentage of the stock stabilizer in the treatment agent is preferably 0.1 to 30% by weight. The upper limit of this weight percentage is more preferably 20% by weight, and even more preferably 15% by weight. On the other hand, the lower limit of this weight percentage is more preferably 0.2% by weight, and even more preferably 0.5% by weight. Also, for example, 0.2 to 20% by weight is more preferably, and even more preferably 0.5 to 15% by weight.

[0091] The synthetic fiber treatment agent of the present invention may consist solely of the aforementioned components comprising non-volatile components, or it may consist of non-volatile components and a stock solution stabilizer, or the non-volatile components may be diluted with a volatile low-viscosity mineral oil. The weight percentage of water in the treatment agent is preferably more than 0 to 16% by weight, in terms of the stability of the treatment agent. The upper limit of this weight percentage is more preferably 14% by weight, and even more preferably 12% by weight. On the other hand, the lower limit of this weight percentage is more preferably 2% by weight, and even more preferably 4% by weight. Also, for example, 2 to 14% by weight is more preferably, and even more preferably 4 to 12% by weight.

[0092] The method for producing the synthetic fiber treatment agent of the present invention is not particularly limited, and known methods can be employed. The synthetic fiber treatment agent is produced by adding and mixing the constituent components in any or specific order. From the viewpoint of improving heat resistance, purified versions of each component, such as catalysts, may be used. In particular, the ester component (A) and the nonionic surfactant (B) having a polyoxyalkylene skeleton without ester bonds used in the present invention may contain inorganic substances, and it is desirable to remove and purify the inorganic substances in order to improve the stability and heat resistance of the treatment agent. As a method for removing and purifying inorganic substances, known methods can be used, for example, by filtration using diatomaceous earth or by adsorption removal using an inorganic synthetic adsorbent. Bio-based raw materials may be used for each component constituting the synthetic fiber treatment agent of the present invention. In addition to the above components, the synthetic fiber treatment agent of the present invention may contain known components used in synthetic fiber treatment agents, and may have known physical properties in synthetic fiber treatment agents.

[0093] [Method for producing a treatment agent for synthetic fibers] The second aspect of the present invention relates to a method for producing a treatment agent for synthetic fibers (hereinafter sometimes simply referred to as a method for producing a treatment agent), which contains a nonionic surfactant (B) having a polyoxyalkylene skeleton without ester bonds and an ester component (A), and satisfies the following conditions 1 and 2, wherein the ester component (A) includes at least one selected from an ester compound represented by the following general formula (1) and a compound having a structure in which polyoxyalkylene glycol and a fatty acid are ester-bonded, and the nonionic surfactant (B) having a polyoxyalkylene skeleton without ester bonds includes a nonionic surfactant (B1) having an alkyl group having 12 to 15 carbon atoms, and the treatment agent A synthetic fiber treatment agent that satisfies conditions 1 and 2 can be suitably produced if the proportion of nonionic surfactant (B) having a polyoxyalkylene skeleton without ester bonds in the volatile matter is 40 to 97% by weight, the strong acid value of the nonvolatile matter of the treatment agent is 0.00 to 0.10 mg KOH / g, the saponification value of the nonvolatile matter of the treatment agent is 2 to 20 mg KOH / g, the iodine value of the nonvolatile matter of the treatment agent is 0 to 8.6, the total content of Zr and Ti elements in the nonvolatile matter of the treatment agent is 0 to 54 ppm, the total content of K and Na elements in the nonvolatile matter of the treatment agent is 50 to 2000 ppm, and the Si element content in the nonvolatile matter of the treatment agent is 50 to 2000 ppm. Condition 1: The remaining percentage of non-volatile components of the treatment agent after heating 0.5 g at 200°C for 1 hour is 10 to 30% by weight. Condition 2: The remaining percentage of non-volatile components of the treatment agent after heating 0.5 g at 200°C for 24 hours is greater than 0% to 6% by weight. (In the formula, R １ R represents an alkyl or alkenyl group having 4 to 24 carbon atoms. ２ (This represents an alkyl or alkenyl group having 6 to 24 carbon atoms.) The synthetic fiber treatment agent of the first embodiment can be suitably produced by the method for producing the synthetic fiber treatment agent of the second embodiment of the present invention.

[0094] [Synthetic Fiber, Method for Manufacturing Synthetic Fiber, and Fiber Structure] The synthetic fiber of the present invention is obtained by applying the synthetic fiber treatment agent of the first aspect of the present invention. The synthetic fiber of the present invention has excellent yarn quality because it is treated with the synthetic fiber of the present invention. The method for manufacturing the synthetic fiber is not particularly limited, but it can be suitably manufactured by the method for manufacturing the synthetic fiber of the present invention. The method for manufacturing the synthetic fiber of the present invention includes a step of applying the synthetic fiber treatment agent of the present invention to the raw synthetic fiber. According to the manufacturing method of the invention, the occurrence of scum and yarn breakage can be reduced, and synthetic fibers with excellent yarn quality can be obtained. In this invention, the raw synthetic fiber refers to synthetic fiber to which the treatment agent has not been applied.

[0095] There are no particular limitations on the process of applying the synthetic fiber treatment agent, and known methods can be employed. Typically, the synthetic fiber treatment agent is applied during the spinning process of the raw synthetic fiber. After the treatment agent is applied, the fiber is stretched and heat-set using a hot roller and then wound up. Thus, the synthetic fiber treatment agent of the present invention can be suitably used when there is a step of heat stretching after the treatment agent is applied without being wound up. As an example of the temperature during heat stretching, for polyester and nylon, 210 to 260°C is assumed for industrial materials, and 110 to 220°C is assumed for clothing.

[0096] As mentioned above, synthetic fiber treatment agents applied to raw synthetic fibers include treatment agents consisting solely of non-volatile components, treatment agents in which non-volatile components are diluted with low-viscosity mineral oil, and water-based emulsion treatment agents in which non-volatile components are emulsified in water. While there are no particular limitations on the application method, examples include guide lubrication, roller lubrication, dip lubrication, and spray lubrication. Among these, guide lubrication and roller lubrication are preferred due to their ease of control over the application amount.

[0097] There are no particular limitations on the amount of non-volatile components added to the synthetic fiber treatment agent, but in terms of reducing fluff and providing antistatic properties, 0.05 to 5% by weight is preferred, 0.1 to 3% by weight is more preferred, and 0.1 to 2% by weight is even more preferred, relative to the raw synthetic fiber.

[0098] (Raw materials) Examples of synthetic fibers include polyester fibers, polyamide fibers, and polyolefin fibers. The synthetic fiber treatment agent of the present invention is suitable for synthetic fibers such as polyester fibers, polyamide fibers, and polyolefin fibers. Examples of polyester fibers include polyester (PET) mainly composed of ethylene terephthalate, polyester (PTT) mainly composed of trimethylene ethylene terephthalate, polyester (PBT) mainly composed of butylene ethylene terephthalate, and polyester (PLA) mainly composed of lactic acid. Examples of polyamide fibers include nylon 6 and nylon 66. Examples of polyolefin fibers include polypropylene and polyethylene. There are no particular limitations on the method of manufacturing synthetic fibers, and known methods can be used. (Raw materials) There are no particular limitations on the form of synthetic fibers, but multifilaments or monofilaments are preferred.

[0099] (Fiber Structures) The fiber structures of the present invention include synthetic fibers obtained by the manufacturing method of the present invention described above. Specifically, these include fabrics woven on a water jet loom, air jet loom, or rapier loom using synthetic fibers treated with the synthetic fiber treatment agent of the present invention, knitted fabrics knitted on a circular knitting machine, warp knitting machine, or weft knitting machine, and cords and ropes obtained by twisting yarn. Applications of the fiber structures include industrial materials such as tire cords, seat belts, airbags, fishing nets, and ropes, as well as clothing. There are no particular limitations on the method of manufacturing the fabrics and knitted fabrics, and known methods can be used.

[0100] The present invention will be described below with reference to examples. The present invention is not limited to the examples described herein. In the text and tables, "%" means "weight percent".

[0101] [Examples 1-21, Comparative Examples 1-15] Ester components (A) listed in Tables 1-4, nonionic surfactants having a polyoxyalkylene skeleton but lacking ester bonds (B), other surfactants (C), other components (D), and stock stabilizers were mixed and stirred until homogeneous to prepare synthetic fiber treatment agents for Examples 1-21 and Comparative Examples 1-15. Using each prepared treatment agent, the accumulation of dirt on pins, the ability to wipe away dirt from pins, and tension fluctuations were evaluated using the following methods. Furthermore, the non-volatile components of the treatment agent were used to determine the residual rate after heating under conditions 1 and 2, as well as the strong acid value, saponification value, hydroxyl value, iodine value, Zr element content, Ti element content, K element content, Na element content, Si element content, P element content, sulfate ion (SO4) ４ ２－ ) and chloride ions (Cl － The following parameters were measured. The results are shown in Tables 1 to 3.

[0102] (Evaluation of residual rate after heating under conditions 1 and 2) Weight of stainless steel plate (7 cm in diameter, 1 cm deep) (W) １ ) was weighed. Then approximately 0.5 g of the non-volatile component of the treatment agent was added, and the weight (W ２ The sample was weighed (W). The sample was placed in a heat treatment device that had been preheated to 200°C. Without changing the setting of the heat treatment device from 200°C, the timer started counting immediately after the sample was placed in the device, and the heat treatment was performed for 1 hour or 24 hours. After that, the sample was removed from the heat treatment device, allowed to cool to 20-40°C, and then weighed (W). ３ ) was done. The measured weight (W １ ) (W ２ ) (W ３ The residual rate after heating was calculated using the following formula: Residual rate after heating (weight %) = 100 × (W ３ -W １ ) / (W ２ -W １ Furthermore, an industrial constant temperature testing machine (VTFH-216-2TG, manufactured by Isuzu Manufacturing Co., Ltd.) was used as the heat treatment device.

[0103] (Evaluation of pin dirt accumulation, pin dirt wipeability, and tension fluctuations) The above treatment agent was quantitatively applied at a rate of 20% by weight to 1000 denier, 96 filament untreated polyester filament. After removing volatile components by passing the filament through a roller heated to 150°C using a thread-running friction measuring machine, it was brought into contact with a matte chrome pin heated to 240°C. The filament was run for 8 hours at an initial tension of 500g and a running speed of 2m / min, and the degree of pin dirt accumulation, pin dirt wipeability, and tension fluctuations were evaluated. In anticipation of evaluation under harsh conditions, a 20% by weight application of the treatment agent was used, and those that passed the test in reducing the amount of thermally degraded material and suppressing tension fluctuations even under harsh conditions were judged to be able to achieve both reduction of thermally degraded material and suppression of tension fluctuations. As a comparative evaluation to the above evaluation under harsh conditions, an evaluation was also performed when the treatment agent was applied at a rate of 1% by weight and the filament was run for 24 hours at a running speed of 0.5m / min.

[0104] The degree of dirt accumulation on the pins was evaluated according to the following criteria. Less dirt accumulation indicates a reduction in the amount of thermally degraded material, and ◎ and ○ were considered passing grades. ◎: Almost no dirt was observed, indicating excellent pin dirt accumulation. ○: Only slight dirt was observed, indicating excellent pin dirt accumulation. ×: Dirt was clearly accumulated, indicating poor pin dirt accumulation.

[0105] The tension fluctuation value was calculated using the following formula: Tension fluctuation value (g) = Tension after running the thread (g) - Initial tension (g). The tension after running the thread was measured after 8 hours of running under harsh conditions, and after 24 hours of running for comparative evaluation. The tension fluctuation value was evaluated according to the following criteria, with ◎ and ○ being considered acceptable. ◎: 0g to less than 10g, excellent heat resistance. ○: 10g or more and less than 20g, excellent heat resistance. ×: 20g or more, poor heat resistance.

[0106] The ability to wipe away dirt from the pins was evaluated using the following method. Dirt that had accumulated on the textured chrome pins was wiped off with gauze soaked in a solution of sodium hydroxide dissolved in water and glycerin. The number of wipes required to remove the dirt was used to evaluate the ability to wipe away dirt. ◎: The dirt could be wiped off in less than two wipes, indicating excellent dirt-removal ability of the pins. ○: The dirt could be wiped off in two to five wipes, indicating excellent dirt-removal ability of the pins. ×: The dirt could not be wiped off in five or more wipes, indicating poor dirt-removal ability of the pins.

[0107] (Method for measuring strong acid value) The strong acid value was measured according to the method specified in JIS K 2501 (2003). Specifically, the non-volatile components of the treatment agent were used as the sample for measurement, dissolved in the mixed solvent described below, and titrated with thymol blue as an indicator. The titration was carried out with a 0.1 mol / L potassium hydroxide standard solution until it turned yellow, and the strong acid value was calculated by applying the titration volume of potassium hydroxide standard solution to the following formula. As the mixed solvent for dissolving the sample, a mixture of denatured alcohol and xylol was used, to which thymol blue was added, and then it was made red with a 0.1 mol / L hydrochloric acid standard solution, and then yellow with a 0.1 mol / L potassium hydroxide standard solution. Strong acid value = (5.61 × A × f) / S (Formula) (In the above formula, A is the titration volume of 0.1 mol / L potassium hydroxide solution (mL), f is the titer of 0.1 mol / L potassium hydroxide solution, and S is the weight of the sample (g)) If the color of the solution does not change from before dissolution when the non-volatile components of the treatment agent are dissolved in the mixed solvent, the strong acid value is set to 0 mg KOH / g.

[0108] (Method for measuring saponification value, hydroxyl value, and iodine value) The values ​​were measured in accordance with the method specified in JIS K-0070-1992 "Test methods for acid value, saponification value, ester value, iodine value, hydroxyl value, and unsaponifiable matter of chemical products".

[0109] (Method for measuring the content of elements P, Zr, Ti, K, Na, and Si detected from the non-volatile matter of the treatment agent by ICP emission spectrometry) (1) Pretreatment (when measuring the content of element P) 0.5 g of the non-volatile matter of the synthetic fiber treatment agent (or an amount such that the amount of element P contained in the non-volatile matter of the synthetic fiber treatment agent is 1 to 100 ppm) was weighed into a platinum crucible, 5 ml of alkaline solution (a homogeneous mixture of 35 g of potassium hydroxide, 915 ml of ethanol, and 50 g of ultrapure water) was added thereto, and the mixture was gradually heated in an electric furnace and ashed at 800 to 850°C. After cooling to room temperature, ultrapure water was added to make a total volume of 50 ml, which was used as the measurement sample. (1-2) Pretreatment (when measuring Zr element content) Weigh 0.5 g of the non-volatile content of the synthetic fiber treatment agent (or an amount in which the amount of Zr element contained in the non-volatile content of the synthetic fiber treatment agent is 1 to 100 ppm) into a platinum crucible, burn the organic components on an electric heater, add about 5 ml of sulfuric acid and heat gradually. After the sulfuric acid has evaporated, it is ashed in an electric furnace at 800 to 850°C. After cooling to room temperature, add about 0.5 ml of hydrochloric acid and ultrapure water to make a total volume of 50 ml, which is used as the measurement sample. (1-3) Pretreatment (when measuring Ti element content) Weigh 0.5 g of the non-volatile content of the synthetic fiber treatment agent (or an amount in which the amount of Ti element contained in the non-volatile content of the synthetic fiber treatment agent is 1 to 100 ppm) into a platinum crucible, burn the organic components on an electric heater, add about 5 ml of sulfuric acid and heat gradually. After the sulfuric acid has evaporated, the material is ashed in an electric furnace at 800-850°C. Next, after cooling to room temperature, approximately 5 ml of sulfuric acid is added and the sulfuric acid is evaporated on an electric heater. After further cooling to room temperature, approximately 0.5 ml of sulfuric acid is added, and ultrapure water is added to make a total volume of 50 ml, which is used as the measurement sample. (1-4) Pretreatment (when measuring the K element content) 0.5 g of the non-volatile content of the synthetic fiber treatment agent (or an amount such that the amount of K element contained in the non-volatile content of the synthetic fiber treatment agent is 1-100 ppm) is weighed into a platinum crucible, the organic components are burned on an electric heater, and approximately 5 ml of sulfuric acid is added and gradually heated. After the sulfuric acid has evaporated, the material is ashed in an electric furnace at 800-850°C. After further cooling to room temperature, approximately 0.5 ml of nitric acid is added, and ultrapure water is added to make a total volume of 50 ml, which is used as the measurement sample.(1-5) Pretreatment (when measuring Na element content) Weigh 0.5 g of the non-volatile content of the synthetic fiber treatment agent (or an amount in which the amount of Na element contained in the non-volatile content of the synthetic fiber treatment agent is 1 to 100 ppm) into a platinum crucible, burn the organic components on an electric heater, add about 5 ml of sulfuric acid and heat gradually. After the sulfuric acid has evaporated, ash is produced in an electric furnace at 800 to 850°C. After cooling to room temperature, add about 0.5 ml of nitric acid and ultrapure water to make a total volume of 50 ml, which is used as the measurement sample. (1-6) Pretreatment (when measuring Si element content) Weigh about 0.5 g of the non-volatile content of the synthetic fiber treatment agent (or an amount in which the amount of Si element contained in the non-volatile content of the synthetic fiber treatment agent is 1 to 100 ppm) into a platinum crucible, add 4 ml of sulfuric acid and burn the organic components on an electric heater. The material was ashed in an electric furnace at 800°C, 1 g of an alkaline flux (a mixture of sodium carbonate and potassium carbonate) was added, and it was melted at 850°C. After dissolving the alkaline flux in water, ultrapure water was added to make 50 ml, which was used as the measurement sample. (2) Calibration curve Standard solutions of 100 ppm, 10 ppm, and 1 ppm, with known concentrations of P, Zr, Ti, K, Na, and Si, were prepared in advance. These were subjected to ICP (measurement instrument name: Shimadzu Corporation ICPS-8100, ICP emission spectrometer), and calibration curves were created using each standard solution. (3) Measurement The above measurement samples were subjected to ICP (measurement instrument name: Shimadzu Corporation ICPS-8100, ICP emission spectrometer), and the nonvolatile content of P, Zr, Ti, K, Na, and Si of the synthetic fiber treatment agent was measured using the calibration curve created in (2) above.

[0110] (Sulfate ions (SO ４ ２－ )・Chloride ions (Cl － (Measurement method) 5 g of the sample (non-volatile components of the treatment agent) was accurately weighed, and 95 g of ultrapure water was gradually added while stirring to prepare an aqueous solution, which was then brought to a final volume in a 100 ml volumetric flask. 2 ml of the prepared aqueous solution was passed through an ODS (silica gel with octadecyl groups chemically bonded) pretreatment cartridge to remove lipophilic substances. The solution was subjected to ion chromatography analysis, and detection was performed under the following ion chromatography conditions. The amount detected was measured by the peak area ratio relative to a standard solution of known concentration, and sulfate ions (SO4) were detected. ４ ２－), chloride ions (Cl － The amount of ) was converted. <Ion chromatograph conditions> Instrument: Dionex ICS-1500 Suppressor used Analytical column: Dionex IonPac AS14 Inner diameter 4.0 mm x Length 50 mm Guard column: Dionex IonPac AG14 Inner diameter 4.0 mm x Length 250 mm Eluent: 3.5 mmol Na ２ CO ３ , 1.0 mmol NaHCO ３ Flow rate: 1.5ml / min

[0111] The non-volatile content composition figures for synthetic fiber treatment agents in Tables 1-4 indicate the weight percentage of each component in the total non-volatile content of the treatment agent. Details of the treatment agent components used in Tables 1-4 are shown below. <Ester components (A)> A1-1: 2-ethylhexyl alcohol stearate (unpurified) A1-2: 2-ethylhexyl alcohol stearate (Zr catalyst) A1-3: 2-ethylhexyl alcohol stearate (Ti catalyst) A1-4: 2-ethylhexyl alcohol stearate A1-5: 2-ethylhexyl alcohol palmitate A1-6: Lauryl alcohol oleate A2-1: Sorbitan trioylate A6-1: Polyethylene glycol (molecular weight 400) monolaurate (unpurified) A6-2: Polyethylene glycol (molecular weight 400) monolaurate A6-3: Lauryl alcohol EO 7 molar adduct laurate A6-4: Sorbitan trioleate EO 20 molar adduct A6-5: Tristearate of castor oil EO 43 molar adduct A6-6: Castor oil EO 43 molar adduct A6-7: Lauric acid EO 10 molar adduct

[0112] <Nonionic surfactants (B) that do not have ester bonds and have a polyoxyalkylene skeleton> B-1: C4 alcohol EO / PO = 50 / 50 (weight ratio) Random adduct average molecular weight 2000 B-2: C12, C13 alcohol EO / PO = 50 / 50 (weight ratio) Random adduct average molecular weight 1500 B-3: Triethylene glycol EO / PO = 50 / 50 (weight ratio) Random adduct average molecular weight 5000 (no purification treatment) B-4: C12, C13 alcohol EO / PO = 80 / 20 (weight ratio) Block adduct average molecular weight 800 B-5: Lauryl alcohol EO 7 molar adduct B-6: C4 alcohol EO / PO = 50 / 50 (weight ratio) Random adduct average molecular weight 3500 B-7: C4 alcohol EO / PO = 50 / 50 (weight ratio) Random adduct average molecular weight 1800 B-8: C12 alcohol PO / EO = 60 / 40 (weight ratio) block adduct average molecular weight 1400 B-9: Propylene glycol EO / PO = 50 / 50 (weight ratio) random adduct average molecular weight 6000

[0113] <Other Surfactants (C)> C1-1: Alkanesulfonate sodium salt C1-2: Lauryl alcohol ethylene oxide 3 molar adduct phosphate potassium salt C1-3: Oleate potassium salt C1-4: Octyl succinate potassium salt C1-5: Cetyl phosphate potassium salt

[0114] <Other ingredients (D)> D-1: Silicone compound (DOWSIL® FZ-2123, manufactured by Dow Toray Corporation) D-2: Liquid paraffin 60 seconds D-3: Silicone compound 2 (Polyether-modified silicone, molecular weight 9000) <Stabilizer in stock solution (E)> E-1: Water E-2: Ethylene glycol

[0115] <Production Example 1 (Production of A1-1)> In a reaction vessel, 340 g (2.6 mol) of 2-ethylhexyl alcohol, 730 g (2.6 mol) of stearic acid, 2.5 g of p-toluenesulfonic acid as an esterification catalyst, and 0.7 g of a 50% aqueous solution of hypophosphorous acid as a color inhibitor were charged. Under a nitrogen atmosphere, the temperature was gradually raised to 180°C while stirring, and the esterification reaction was carried out for 10 hours to obtain 2-ethylhexyl alcohol stearate ester (without purification treatment) A1-1. The strong acid value was 0.7 mg KOH / g.

[0116] <Production Example 2 (Production of A1-2)> 340 g (2.6 mol) of 2-ethylhexyl alcohol, 730 g (2.6 mol) of stearic acid, and 5 g of Nikka Octix Zirconium 12% (T) (manufactured by Nippon Chemical Industrial Co., Ltd.), an esterification catalyst, were charged into a reaction vessel. The temperature was gradually raised to 240°C while stirring under a nitrogen atmosphere, and the esterification reaction was carried out for 10 hours to obtain 2-ethylhexyl alcohol stearate ester (Zr catalyst) A1-2. The strong acid value was 0 mg KOH / g.

[0117] <Production Example 3 (Production of A1-3)> 2-ethylhexyl alcohol stearate ester (Ti catalyst) A1-3 was obtained using the same production method as in Production Example 2, except that 5 g of Orgatic TC-310 (manufactured by Matsumoto Fine Chemical Co., Ltd.) was used as the esterification catalyst. The strong acid value was 0 mg KOH / g.

[0118] <Production Example 4 (Production of A1-4)> 1000 g of the above-mentioned 2-ethylhexyl alcohol stearate ester (unpurified) A1-1 and 20 g of catalyst adsorbent Kyoward 2000 (manufactured by Kyowa Chemical Industry Co., Ltd.) were charged into a reaction vessel, and catalyst adsorption treatment was carried out at 90°C for 1 hour while stirring under a nitrogen atmosphere. After that, filtration was performed using filter paper (filter paper No. 424, manufactured by Advantec) to obtain 2-ethylhexyl alcohol stearate ester A1-4. The strong acid value was 0 mg KOH / g.

[0119] <Production Example 5 (Production of A1-5)> In a reaction vessel, 365 g (2.8 mol) of 2-ethylhexyl alcohol, 705 g (2.8 mol) of palmitic acid, 2.5 g of p-toluenesulfonic acid as an esterification catalyst, and 0.7 g of a 50% aqueous solution of hypophosphorous acid as a color inhibitor were charged. Under a nitrogen atmosphere, the temperature was gradually raised to 180°C while stirring, and the esterification reaction was carried out for 10 hours. After that, it was cooled to 90°C. Then, 200 g of soft water was added, and the mixture was washed with water at 90°C for 30 minutes while stirring. After that, stirring was stopped and the mixture was allowed to stand for 2 hours to separate the oil layer and the water layer, and the water layer was discharged and removed. Then, the same washing treatment was repeated. After that, the oil layer was dehydrated at 130°C for 2 hours while stirring under a nitrogen atmosphere. After that, the mixture was filtered using filter paper (filter paper No. 424, manufactured by Advantec) to obtain 2-ethylhexyl alcohol palmitate ester A1-5. The strong acid value was 0 mg KOH / g.

[0120] <Production Example 6 (Production of A1-6)> Lauryl alcohol oleate ester A1-6 was obtained using the same production method as in Production Example 5, except that the raw materials were 430 g (2.3 mol) of lauryl alcohol and 640 g (2.3 mol) of oleic acid. The strong acid value was 0 mg KOH / g.

[0121] <Production Example 7 (Production of A6-1)> Polyethylene glycol (molecular weight 400) monolaurate (without purification treatment) A6-1 was obtained using the same production method as in Production Example 1, except that the raw materials were polyethylene glycol (molecular weight 400) 540 g (2.7 mol) and lauric acid 540 g (2.7 mol). The strong acid value was 0.7 mg KOH / g.

[0122] <Production Example 8 (Production of A6-2)> 1000 g of the above polyethylene glycol (molecular weight 400) monolaurate (unpurified) A6-1 and 20 g of the catalyst adsorbent Kyoward 2000 (manufactured by Kyowa Chemical Industry Co., Ltd.) were charged into a reaction vessel, and catalyst adsorption treatment was carried out at 90°C for 1 hour while stirring under a nitrogen atmosphere. After that, the mixture was filtered using filter paper (filter paper No. 424, manufactured by Advantec) to obtain polyethylene glycol (molecular weight 400) monolaurate A6-2. The strong acid value was 0 mg KOH / g.

[0123] <Production Example 9 (Production of A6-4, A6-5, A6-6, A6-7, B-1, B-2, B-3, B-4, B-5, B-6, B-7, B-8, B-9)> A6-4, A6-5, A6-6, A6-7, B-1, B-2, B-3, B-4, B-5, B-6, B-7, B-8, B-9 can be produced by known methods. They were prepared by adding the necessary alkylene oxide to the monohydric or polyhydric alcohol or monohydric or polyhydric carboxylic acid, using sodium hydroxide as a catalyst to introduce the alkylene oxy group. Subsequently, A6-4, A6-5, A6-6, A6-7, B-1, B-2, B-4, B-5, B-6, B-7, B-8, and B-9 were subjected to catalytic adsorption using the catalyst adsorbent Kyoward 700SL (manufactured by Kyowa Chemical Industry Co., Ltd.), followed by filtration using filter paper (filter paper No. 424, manufactured by Advantec). Catalytic adsorption treatment and filtration were not performed on B-3. The residual sodium content was 15 ppm for A6-4, 18 ppm for A6-5, 20 ppm for A6-6, 15 ppm for A6-7, 18 ppm for B-1, 28 ppm for B-2, 854 ppm for B-3, 27 ppm for B-4, 24 ppm for B-5, 20 ppm for B-6, 17 ppm for B-7, 20 ppm for B-8, and 22 ppm for B-9. The strong acid value was 0 mgKOH / g for all samples.

[0124] <Production Example 10 (Production of A6-3)> 790 g (1.6 mol) of the above-mentioned lauryl alcohol EO 7 molar adduct (B-5), 320 g (1.6 mol) of lauric acid, 2.5 g of p-toluenesulfonic acid as an esterification catalyst, and 0.7 g of a 50% aqueous solution of hypophosphorous acid as a color inhibitor were charged into a reaction vessel. The temperature was gradually raised to 190°C while stirring under a nitrogen atmosphere, and the esterification reaction was carried out for 10 hours. Then, 20 g of the catalyst adsorbent Kyoward 2000 (manufactured by Kyowa Chemical Industry Co., Ltd.) was charged, and catalyst adsorption treatment was carried out at 90°C for 1 hour while stirring under a nitrogen atmosphere. After that, the mixture was filtered using filter paper (filter paper No. 424, manufactured by Advantec) to obtain lauryl alcohol EO 7 molar adduct laurate A6-3. The strong acid value was 0 mg KOH / g.

[0125] <Production Example 11 (Production of A2-1)> In a reaction vessel, 846 g (3.0 mol) of oleic acid, 164.1 g (1.0 mol) of sorbitan, 2.5 g of p-toluenesulfonic acid as an esterification catalyst, and 0.7 g of a 50% aqueous solution of hypophosphorous acid as a color inhibitor were charged. The temperature was gradually raised to 190°C while stirring under a nitrogen atmosphere, and the esterification reaction was carried out for 10 hours. After that, 20 g of the catalyst adsorbent Kyoward 2000 (manufactured by Kyowa Chemical Industry Co., Ltd.) was charged, and catalyst adsorption treatment was carried out at 90°C for 1 hour while stirring under a nitrogen atmosphere. After that, the mixture was filtered using filter paper (filter paper No. 424, manufactured by Advantec) to obtain sorbitan trioleate A2-1. The strong acid value was 0 mg KOH / g.

[0126]

[0127]

[0128]

[0129]

[0130] As can be seen from Tables 1 to 4, the synthetic fiber treatment agent in the example is the synthetic fiber treatment agent of the present invention, containing an ester component (A) and a nonionic surfactant (B) having a polyoxyalkylene skeleton without ester bonds. The strong acid value and saponification value of the nonvolatile components of the treatment agent are within a specific range, and it satisfies specific conditions 1 and 2 regarding the residual rate after heating. Therefore, it exhibits excellent performance in reducing the amount of thermally degraded materials and suppressing tension fluctuations even under harsh conditions, and has excellent durability in reducing the amount of thermally degraded materials and suppressing tension fluctuations. On the other hand, the comparative example is not the synthetic fiber treatment agent of the present invention, and therefore exhibits inferior performance in reducing the amount of thermally degraded materials and suppressing tension fluctuations. In comparative evaluation, all treatment agents met the acceptable level for reducing the amount of thermally degraded materials and suppressing tension fluctuations.

[0131] The synthetic fiber treatment agent of the present invention is suitable for industrial materials such as tarpaulins, tire cords, seat belts, airbags, fishing nets, ropes, and slings, as well as synthetic fiber filaments used for false twist processing and clothing such as woven and knitted fabrics, and is particularly suitable for synthetic fiber filaments used for false twist processing and clothing such as woven and knitted fabrics.

Claims

1. A method for producing a synthetic fiber treatment agent that contains a nonionic surfactant (B) having a polyoxyalkylene skeleton without ester bonds and an ester component (A), and satisfies the following conditions 1 and 2, wherein the ester component (A) comprises at least one selected from an ester compound represented by the following general formula (1) and a compound having a structure in which polyoxyalkylene glycol and a fatty acid are ester-bonded, the nonionic surfactant (B) comprises a nonionic surfactant (B1) having an alkyl group having 12 to 15 carbon atoms, the proportion of the nonionic surfactant (B) in the nonvolatile content of the treatment agent is 40 to 97% by weight, the strong acid value of the nonvolatile content of the treatment agent is 0.00 to 0.10 mgKOH / g, the saponification value of the nonvolatile content of the treatment agent is 2 to 20 mgKOH / g, and the iodine value of the nonvolatile content of the treatment agent is 0 to 8.

6. A method for producing a treatment agent for synthetic fibers, characterized in that the total content of Zr and Ti elements in the nonvolatile matter of the treatment agent is 0 to 54 ppm, the total content of K and Na elements in the nonvolatile matter of the treatment agent is 50 to 2000 ppm, and the content of Si elements in the nonvolatile matter of the treatment agent is 50 to 2000 ppm. Condition 1: The residual rate of the nonvolatile matter of the treatment agent after heating 0.5 g at 200°C for 1 hour is 10 to 30% by weight. Condition 2: The residual rate of the nonvolatile matter of the treatment agent after heating 0.5 g at 200°C for 24 hours is greater than 0 to 6% by weight. (In the formula, R １ R represents an alkyl or alkenyl group having 4 to 24 carbon atoms. ２ (This represents an alkyl or alkenyl group having 6 to 24 carbon atoms.) 2. A synthetic fiber treatment agent comprising a nonionic surfactant (B) having a polyoxyalkylene skeleton without ester bonds and an ester component (A), wherein the ester component (A) comprises at least one selected from an ester compound represented by the following general formula (1) and a compound having a structure in which polyoxyalkylene glycol and a fatty acid are ester-bonded, the nonionic surfactant (B) comprises a nonionic surfactant (B1) having an alkyl group having 12 to 15 carbon atoms, the proportion of the nonionic surfactant (B) in the nonvolatile content of the treatment agent is 40 to 97% by weight, the strong acid value of the nonvolatile content of the treatment agent is 0.00 to 0.10 mg KOH / g, the saponification value of the nonvolatile content of the treatment agent is 2 to 20 mg KOH / g, and the following conditions 1 and 2 are satisfied. Condition 1: The remaining non-volatile content of 0.5 g of the treatment agent after heating at 200°C for 1 hour is 10 to 30% by weight. Condition 2: The remaining non-volatile content of 0.5 g of the treatment agent after heating at 200°C for 24 hours is greater than 0 to 6% by weight. (In the formula, R １ R represents an alkyl or alkenyl group having 4 to 24 carbon atoms. ２ (This represents an alkyl or alkenyl group having 6 to 24 carbon atoms.) 3. The synthetic fiber treatment agent according to claim 2, wherein the content of Si element in the nonvolatile content of the treatment agent is 50 to 2000 ppm.

4. The synthetic fiber treatment agent according to claim 2 or 3, wherein the total content of K element and Na element in the nonvolatile content of the treatment agent is 50 to 2000 ppm.

5. The synthetic fiber treatment agent according to any one of claims 2 to 4, wherein the iodine value of the nonvolatile components of the treatment agent is 8.6 or less.

6. The synthetic fiber treatment agent according to any one of claims 2 to 5, wherein the total content of Zr and Ti elements in the nonvolatile content of the treatment agent is 30 ppm or less.

7. The synthetic fiber treatment agent according to any one of claims 2 to 6, wherein the proportion of the nonionic surfactant (B1) in the nonvolatile content of the treatment agent is 50 to 95% by weight.

8. The synthetic fiber treatment agent according to any one of claims 2 to 7, wherein the proportion of the silicone compound in the nonvolatile content of the treatment agent is 0.05 to 1.5% by weight.

9. A synthetic fiber treatment agent according to any one of claims 2 to 8, comprising 0 to 16% by weight of water.

10. A synthetic fiber obtained by applying a synthetic fiber treatment agent according to any one of claims 2 to 9 to a raw synthetic fiber.

11. A method for producing synthetic fibers, comprising the step of applying a synthetic fiber treatment agent according to any one of claims 2 to 9 to a raw synthetic fiber.

12. A fibrous structure comprising the synthetic fiber described in claim 10.

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