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

Abstract

The object of the invention is to provide a treatment agent for synthetic fibers that can achieve both a reduction in the amount of thermally degraded material and suppression of tension fluctuations. 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 specific conditions 1 and 2, wherein the ester component (A) comprises at least one selected from an ester compound represented by 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, and the proportion of the nonionic surfactant (B) in the nonvolatile content of the treatment agent, the strong acid value, saponification value, iodine value, content of Zr and Ti elements, content of K and Na elements, and content of Si element are within specific ranges.

Description

[Technical Field]

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

[0002] In the manufacturing of synthetic fibers for industrial and apparel applications, fiber treatment agents are applied, and the fibers undergo processes that involve high-temperature thermal exposure. Therefore, treatment agents that do not easily contaminate equipment even when subjected to high temperatures for extended periods are required. 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 and leading to an increase in fluff and yarn breakage, as well as the time required to clean the equipment. [Prior art documents] [Patent Documents]

[0003] [Patent Document 1] Japanese Patent Application Publication No. 2018-150665 [Overview of the Initiative] [Problems that the invention aims to solve]

[0004] An investigation into the cause revealed that the problem stemmed from an inability to simultaneously reduce the amount of thermally degraded material and suppress tension fluctuations. Therefore, the object 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. [Means for solving the problem]

[0005] As a result of diligent research, the 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, we discovered that the problems of the present invention can be solved by using a synthetic fiber treatment agent composed of specific components, where 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, thus leading to the present invention. In other words, 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, The ester component (A) comprises 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. The nonionic surfactant (B) comprises a nonionic surfactant (B1) having an alkyl group with 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 component of the aforementioned treatment agent is 0.00 to 0.10 mg KOH / g. The saponification value of the non-volatile components of the aforementioned treatment agent is 2 to 20 mg KOH / g. The iodine value of the non-volatile components of the aforementioned treatment agent is 0 to 8.6. The total content of Zr and Ti elements in the nonvolatile matter of the aforementioned treatment agent is 0 to 54 ppm. The total content of K and Na elements in the nonvolatile matter of the aforementioned treatment agent is 50 to 2000 ppm. A method for producing a treatment agent for synthetic fibers, characterized in that the content of Si element in the nonvolatile components of the treatment agent is 50 to 2000 ppm. Condition 1: The residual content of 0.5 g of the non-volatile components of the treatment agent after heating at 200°C for 1 hour is 10-30% by weight. Condition 2: The residual percentage of the 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. [ka] (In the formula, R 1represents an alkyl or alkenyl group having 4 to 24 carbon atoms, and R 2 represents an alkyl or alkenyl group having 6 to 24 carbon atoms.) <2> A treatment agent for synthetic fibers containing a nonionic surfactant (B) having no ester bond and having a polyoxyalkylene skeleton and an ester component (A), where 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 a polyoxyalkylene glycol and a fatty acid are ester-bonded, where the nonionic surfactant (B) includes a nonionic surfactant (B1) having an alkyl group having 12 to 15 carbon atoms, where the proportion of the nonionic surfactant (B) in the nonvolatile content of the treatment agent is 40 to 97% by weight, where the strong acid value of the nonvolatile content of the treatment agent is 0.00 to 0.10 mgKOH / g, where the saponification value of the nonvolatile content of the treatment agent is 2 to 20 mgKOH / g, A treatment agent for synthetic fibers that satisfies the following Conditions 1 and Condition 2. Condition 1: The residual ratio 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 ratio after heating 0.5 g of the nonvolatile content of the treatment agent at 200 °C for 24 hours is more than 0 to 6% by weight

Chemical formula

Advantages of the Invention

[0006] According to the method for producing a sizing agent for synthetic fibers of the present invention, a sizing agent for synthetic fibers that can achieve both reduction of the amount of thermally degraded products and suppression of tension fluctuations can be produced. The sizing agent for synthetic fibers of the present invention can achieve both reduction of the amount of thermally degraded products and suppression of tension fluctuations. As a result, the productivity of the synthetic fiber is excellent. According to the method for producing a synthetic fiber of the present invention, since a sizing agent for synthetic fibers that can achieve both reduction of the amount of thermally degraded products and suppression of tension fluctuations is used, the productivity of the synthetic fiber is excellent. The synthetic fiber of the present invention is excellent in quality. The fiber structure of the present invention is excellent in quality.

Embodiments for Carrying Out the Invention

[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 an ester component (A). The ester component (A) is not particularly limited as long as it is a compound having an ester bond, but examples of known components 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 components (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 esterified, 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 the ester compound (A1), but it is preferably a compound represented by the following general formula (1).

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

[0011] In formula (1), R 1 has no particular limitation in terms of the number of carbon atoms, but from the viewpoint of smoothness, 6 to 22 are preferred. 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 8, even more preferably 10, and particularly preferably 12. Also, for example, 8 to 20 are more preferred, and 10 to 18 are even more preferred. R 1 may be either an alkyl group or an alkenyl group, but from the viewpoint of excellent heat resistance, an alkyl group is preferred.

[0012] In formula (1), R 2 has no particular limitation in terms of the number of carbon atoms, but from the viewpoint of smoothness, 6 to 22 are preferred. 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 8, even more preferably 10, and particularly preferably 12. Also, for example, 8 to 20 are more preferred, and 10 to 18 are even more preferred. R 2 may be either an alkyl group or an alkenyl group, but from the viewpoint of strong oil film strength and difficulty in generating flyers, an alkenyl group is preferred.

[0013] The ester compound (A1) is not particularly limited, but examples include 2-decyltetradecanoyl elusinate, 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 preferred.

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

[0015] 2) Ester compounds (A2) Ester compound (A2) is a compound having a structure in which an aliphatic polyhydric alcohol and a fatty acid (aliphatic monocarboxylic acid) are esterified, 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, and sucrose. 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. While there are no particular limitations on the number of unsaturated bonds, one, two, or three are preferred in terms of smoothness, heat resistance, and smoke emission. While there are no particular limitations on the number of carbon atoms in the fatty acid, 8 to 24 are preferred for achieving both oil film strength and smoothness. The upper limit of the carbon number is more preferably 20, even more preferably 18, and particularly preferably 16. On the other hand, the lower limit of the carbon number is more preferably 10, even more preferably 12, and particularly preferably 14. For example, 10 to 20 is more preferred, and 12 to 18 is even more preferred. One or more fatty acids may be used, and saturated 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] 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 that it is 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 from the peaks measured with a differential refractive index detector after injecting a sample at a concentration of 3 mg / cc into separation columns KF-402HQ and KF-403HQ manufactured by Showa Denko K.K., using a high-speed gel permeation chromatography apparatus HLC-8220GPC manufactured by Tosoh Corporation.

[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 compounds (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 contain 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 can 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 is divalent or higher; one or more types can be used. The aliphatic polycarboxylic acid used in this invention does not include 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 aliphatic polycarboxylic acids include citric acid, isocitric acid, malic acid, aconitic acid, oxaloacetate, oxalosuccinic acid, succinic acid, fumaric acid, maleic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, and sebacic acid. Among these, aconitic acid, oxaloacetate, 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 ester compounds (A3) include dioctyl adipic acid, dilauryl adipic acid, dioleyl adipic acid, diisocetyl adipic acid, dioctyl sebacate, dilauryl sebacate, dioleyl sebacate, and diisocetyl sebacate.

[0028] Ester compounds (A3) are compounds that have one or more ester bonds in their molecule. There are no particular limitations on the iodine value of ester compounds (A3).

[0029] The weight-average molecular weight of the ester compound (A3) is not particularly limited, but is preferably 150 to 1000 in terms of smoothness and low fume generation. The upper limit of the average molecular weight is more preferably 800, and even more preferably 700. On the other hand, the lower limit of the average molecular weight is more preferably 300, and even more preferably 500. Also, for example, is more preferably 300 to 800, and even more preferably 500 to 700.

[0030] Ester compounds (A3) can generally be synthesized and obtained using commercially available aliphatic monohydric alcohols and aliphatic polycarboxylic acids by known methods.

[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 alcohol, dialkylbenzene alcohol, 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. Examples of polyhydric alcohols include aliphatic polyhydric alcohols, as explained in ester compounds (A2), and aromatic polyhydric alcohols, as explained 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 monohydric aromatic alcohols such as alkylbenzene alcohols, dialkylbenzene alcohols, and polyhydric aromatic 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, gadelic 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 explained in ester compounds (A3), and aromatic polyvalent carboxylic acids, as explained in ester compounds (A4-1).

[0038] 5) Sulfur-containing ester compounds (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 alcohols and monoester compounds of thiodipropionic acid and aliphatic alcohols. Sulfur-containing ester compounds are components with antioxidant properties. Using these sulfur-containing ester compounds can improve the heat resistance of the treatment agent. 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 400 to 1000 is preferred in terms of smoothness and low smoke emission. 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. For example, 500 to 900 is more preferred, and 600 to 800 is even more preferred. The aliphatic alcohol constituting the sulfur-containing ester compound may be saturated or unsaturated. 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 (hereinafter simply referred to as diester in this paragraph) and a monoester compound of thiodipropionic acid and an aliphatic alcohol (hereinafter simply referred to as monoester in this paragraph). In this case, the weight ratio of diester to 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 even more preferably 100 / 0 to 80 / 20.

[0039] 6) Ester compounds having polyoxyalkylene groups (A6) The ester compound (A6) having a polyoxyalkylene group is not particularly limited as long as it is a compound having a polyoxyalkylene group and an ester bond. 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, and fatty acid esters of polyoxyalkylene glycols. 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) Polyhydroxyesters are structurally esters of polyoxyalkylene group-containing hydroxy fatty acids and polyhydric alcohols, 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 polyhydroxyesters 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 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 alkylene oxides, the order of addition is not particularly limited, and the addition can be in a block-like or random pattern. Alkylene oxide addition can be carried out by known methods, but it is generally performed 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] Ester compounds (A6) having a polyoxyalkylene group 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 ester) Polyoxyalkylene polyhydric 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 a polyhydric alcohol. 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 preferably, 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. The weight-average molecular weight of the polyoxyalkylene polyhydric alcohol fatty acid ester is not particularly limited, but is preferably, for example, 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 500, and even more preferably 700. Also, for example, is more preferably 500 to 5000, 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 ester) Polyoxyalkylene aliphatic monohydric alcohol fatty acid esters are compounds in which an alkylene oxide such as ethylene oxide, propylene oxide, or butylene oxide is added to an aliphatic monohydric alcohol, and a fatty acid is esterified to this compound.

[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, for example, 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] (A compound in which polyoxyalkylene glycol and a fatty acid are esterified together.) Compounds having 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 the 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 above general formula (1) 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 a purified product from which catalysts and other impurities have been removed, from the viewpoint of improving heat resistance and obtaining a clear treatment agent.

[0060] [Nonionic surfactant having a polyoxyalkylene skeleton without ester bonds (B)] 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 surfactants (B) include polyoxyalkylene polyhydric alcohol ethers and polyoxyalkylene aliphatic alcohol ethers. The nonionic surfactant (B) includes a nonionic surfactant (B1) having an alkyl group with 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 with 12 to 15 carbon atoms. The nonionic surfactant (B) preferably contains a polyoxyalkylene polyhydric alcohol ether, and preferably contains polyoxyalkylene glycol (B2) in terms of oil film strength and flocculation properties.

[0061] (Polyoxyalkylene polyhydric alcohol ether) Polyoxyalkylene polyhydric 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 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 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 4 moles, and even more preferably 5 moles. Also, for example, 4 to 70 moles is more preferably, and even more preferably 5 to 50 moles. Furthermore, the proportion of ethylene oxide in the alkylene oxide is preferably 10 mol% or more, and even more preferably 50 mol% or more. The weight-average molecular weight of the polyoxyalkylene polyhydric alcohol ether is not particularly limited, but is preferably 150 to 10000 in terms of emulsifying properties 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. Also, for example, is more preferably 300 to 8000, 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. Other surfactants (C) include anionic surfactants (C1), cationic surfactants, amphoteric surfactants, etc., and are not particularly limited as long as they are surfactants other than the ester component (A) and nonionic surfactants (B) that do not have ester bonds and have a polyoxyalkylene skeleton. 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), and fatty acid soaps (C1-3). 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 surfactant containing sulfur element (C1-1)] While there are no particular limitations on the anionic surfactant containing the sulfur element, organic sulfonates and organic sulfate esters 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 process. The ratio of sodium sulfate and sodium chloride in these raw materials can be calculated from the weight percentage of sulfate and chloride ions detected in the raw materials using 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 elements.

[0070] [Organophosphate ester compounds (C1-2)] There are no particular limitations on the organic phosphate ester compound, but it must contain one or more hydrocarbon groups with 6 to 24 carbon atoms in its structure, and the organic phosphate portion may be mono, di, or poly. It may also contain inorganic phosphate. Furthermore, the structure may contain alkylene oxy groups, 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] While there are no particular limitations on amphoteric surfactants, examples include lauryldimethylbetaine, stearyldimethylbetaine, and dimethyllaurylamine oxide.

[0074] [Other ingredients (D)] The treatment agent of the present invention may also 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), from the standpoint of improving the heat resistance and spinnability of the raw yarn. Other components (D) include antioxidants, silicone compounds, and non-volatile mineral oils at room temperature (machine oil, spindle oil, liquid paraffin, etc.). There are no particular limitations on components other than the ester component (A), the nonionic surfactant (B) which does not have ester bonds and has a polyoxyalkylene skeleton, and other surfactants (C). However, 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 non-volatile components 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. Other ingredients (D) may be one or more.

[0076] [Treatment agent for synthetic fibers] The first aspect of the present invention provides a synthetic fiber treatment agent 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 preferred, 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 materials. 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. Also, 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 an 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 the value measured in accordance with JIS K-0070-1992. The iodine value can be adjusted by controlling the content of raw materials that contain many double and triple bonds.

[0084] The strong acid value of the nonvolatile component of the treatment agent of the present invention is 0.00 to 0.10 mgKOH / 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 mgKOH / g, more preferably 0.06 mgKOH / g, and even more preferably 0.04 mgKOH / g. On the other hand, the lower limit of the strong acid value is preferably 0.01 mgKOH / 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 strong acidic components (such as p-toluenesulfonic acid, a catalyst used in esterification reactions) are present. This value can be lowered by removing the strong acidic components through purification processes such as washing with water or adsorbent filtration. Additionally, the strong acid value can be lowered by avoiding the use of strong acidic components, such as by performing esterification reactions without a catalyst.

[0085] The saponification value of the non-volatile components of the treatment agent of the present invention is 2 to 20 mg KOH / g. From the viewpoint of smoothness, suppression of tension fluctuations, reduction of thermal degradation, and easier fulfillment of 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. Furthermore, 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 content of 0.5 g of the non-volatile components of the treatment agent after heating at 200°C for 1 hour is 10-30% by weight. Condition 2: The residual percentage of the 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. For conditions 1 and 2, the residual rate must be measured using the sample weight, heating temperature, and time described above. For example, even if the difference in residual rate is clear under condition 1 or 2, if the amount of non-volatile component heated is 5g, the volatilization due to thermal decomposition will be significantly slower, and polymerization will proceed in the center of the treatment 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 will be extremely fast, making the difference in residual rate unclear. The residual percentage after heating at 200°C for 1 hour under Condition 1 is preferably 28% by weight or less, more preferably 26% by weight or less, and similarly, preferably 12% by weight or more, and more preferably 14% by weight or more, in terms of smoothness and suppression of tension fluctuations. For example, 12 to 28% by weight is preferred, and 14 to 26% by weight is more preferred. The residual percentage after heating at 200°C for 24 hours under condition 2 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 suppressing tension fluctuations and reducing the amount of thermally degraded material. 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 easier fulfillment of 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 of the present invention, as detected from the non-volatile content 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, which are non-volatile, or it may consist of non-volatile components and a stock 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 between 0 and 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. The components constituting the synthetic fiber treatment agent of the present invention may also be bio-based raw materials. The synthetic fiber treatment agent of the present invention may contain known components used in synthetic fiber treatment agents in addition to the above components, and may have known physical properties in synthetic fiber treatment agents.

[0093] [Method for manufacturing treatment agents for synthetic fibers] A second aspect of the present invention relates to a method for producing a synthetic fiber treatment agent (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) 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, and the nonionic surfactant (B) having a polyoxyalkylene skeleton without ester bonds comprises 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 content of Si element in the nonvolatile matter of the treatment agent is 50 to 2000 ppm. Condition 1: The residual content of 0.5 g of the non-volatile components of the treatment agent after heating at 200°C for 1 hour is 10-30% by weight. Condition 2: The residual percentage of the 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. [ka] (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 according to the second embodiment of the present invention can be suitably produced by the method for producing the synthetic fiber treatment agent according to the first embodiment.

[0094] [Synthetic fibers, methods for manufacturing synthetic fibers, and fiber structures] The synthetic fiber of the present invention is provided with a synthetic fiber treatment agent according to the first aspect of the present invention. The synthetic fiber of the present invention has excellent yarn quality because it is provided with the synthetic fiber of the present invention. The method for producing the synthetic fiber is not particularly limited, but it can be suitably produced by the method for producing the synthetic fiber of the present invention. The present invention provides a method for producing synthetic fibers, which includes a step of applying the synthetic fiber treatment agent of the present invention to raw synthetic fibers. According to the present invention, the occurrence of scum and yarn breakage can be reduced, and synthetic fibers with excellent yarn quality can be obtained. In this invention, "raw synthetic fibers" refers to synthetic fibers 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 process of heat stretching without winding up after the treatment agent is applied. 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 material) There are no particular limitations on the form of the synthetic fiber, but multifilament or monofilament is preferred.

[0099] (Fiber structures) The fibrous 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 fibrous 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 woven or knitted fabrics, and known methods can be used. [Examples]

[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] The 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 solution stabilizers were mixed and stirred until homogeneous to prepare the synthetic fiber treatment agents for Examples 1-21 and Comparative Examples 1-15. Using each of the prepared treatment agents, the accumulation of dirt on the pins, the ease of wiping off dirt from the pins, and the tension fluctuations were evaluated using the following methods. Furthermore, using the non-volatile components of the treatment agent, 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) were determined by the following method. 2- ) and chloride ions (Cl - The following measurements were taken. The results are shown in Tables 1-3.

[0102] (Evaluation of residual rates after heating under conditions 1 and 2) The weight (W1) of a stainless steel dish (7 cm in diameter, 1 cm in depth) was measured. Approximately 0.5 g of the non-volatile component of the treatment agent was added to it, and the weight (W2) was measured and used as the sample. 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 (W3). The residual rate after heating was calculated from the measured weights (W1), (W2), and (W3) using the following formula. Percentage of remaining food after heating (by weight) = 100 × (W3 - W1) / (W2 - W1) 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 removal ability, and tension fluctuations) The above treatment agent was quantitatively applied at a rate of 20% by weight to 1000 denier, 96-filament oil-free 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 textured chrome pin heated to 240°C. The filament was run for 8 hours at an initial tension of 500g and a thread-running speed of 2m / min, and the degree of dirt accumulation on the pin, the ease of cleaning the dirt off the pin, and the tension fluctuation 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 in thermally degraded material and suppression of tension fluctuations. As a comparative evaluation to the evaluation under the harsh conditions described above, we also conducted an evaluation under conditions where the treatment agent was applied at a concentration of 1% by weight and the vehicle was run for 24 hours at a travel speed of 0.5 m / 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, and the pin dirt accumulation ability was excellent. ○: Only slight dirt is visible, and it has excellent pin dirt accumulation properties. ×: There is clearly an accumulation of dirt, indicating poor resistance to dirt accumulation on the pins.

[0105] The tension fluctuation value was calculated using the following formula. Tension fluctuation (g) = Tension after running the string (g) - Initial tension (g) Furthermore, 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. Furthermore, tension fluctuations were evaluated based on the tension fluctuation values ​​according to the following criteria, and ◎ and ○ were considered acceptable. ◎: Weighing between 0g and less than 10g, it has excellent heat resistance. ○: 10g or more but less than 20g, with excellent heat resistance. ×: It weighs 20g or more and has poor heat resistance.

[0106] The ability of the pins to wipe away dirt was evaluated using the following method. Dirt that had accumulated on the textured chrome pins was wiped away with gauze soaked in a solution of sodium hydroxide dissolved in water and glycerin. The wiping performance was evaluated based on the number of wipes required to remove the dirt. ◎: Dirt can be wiped away in less than two strokes, and it is extremely effective at wiping away dirt from pins. ○: Can be wiped clean with 2 to 5 wipes, and is excellent at removing dirt from pins. ×: It cannot be wiped off even after 5 or more wipes, and its ability to remove dirt from pins is poor.

[0107] (Method for measuring strong acid value) The measurement was performed according to the method specified in JIS K 2501 (2003). Specifically, the non-volatile components of the treatment agent were used as the measurement sample, 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 the potassium hydroxide standard solution to the following formula. As the mixed solvent for dissolving the sample, thymol blue was added to a mixed solvent of denatured alcohol and xylol, which was then 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 (mL) of the 0.1 mol / L potassium hydroxide solution, f is the titer of the 0.1 mol / L potassium hydroxide solution, and S is the weight (g) of the sample.) Furthermore, if the color of the solution did not change before dissolution when the non-volatile components of the treatment agent were dissolved in the mixed solvent, the strong acid value was considered to be 0 mgKOH / g.

[0108] (Methods for measuring saponification value, hydroxyl value, and iodine value) The values ​​were measured according to 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 content of a treatment agent by ICP emission spectrometry) (1) Pretreatment (when measuring the P element content) 0.5 g of the non-volatile component of the synthetic fiber treatment agent (or an amount such that the amount of element P contained in the non-volatile component 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, and the mixture was gradually heated in an electric furnace to 800 to 850°C to cause ashing. 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) 0.5 g of the non-volatile component of the synthetic fiber treatment agent (or an amount such that the amount of Zr element in the non-volatile component of the synthetic fiber treatment agent is 1 to 100 ppm) was weighed into a platinum crucible. After burning the organic components on an electric heater, approximately 5 ml of sulfuric acid was added and the mixture was gradually heated. After the sulfuric acid evaporated, the mixture was ashed in an electric furnace at 800 to 850°C. After cooling to room temperature, approximately 0.5 ml of hydrochloric acid was added, and ultrapure water was added to make a total volume of 50 ml, which was used as the measurement sample. (1-3) Pretreatment (when measuring the Ti element content) 0.5 g of the non-volatile component of the synthetic fiber treatment agent (or an amount such that the amount of Ti element in the non-volatile component of the synthetic fiber treatment agent is 1 to 100 ppm) was weighed into a platinum crucible. After burning the organic components on an electric heater, approximately 5 ml of sulfuric acid was added and the mixture was gradually heated. After the sulfuric acid evaporated, the mixture was ashed in an electric furnace at 800 to 850°C. Next, after cooling to room temperature, approximately 5 ml of sulfuric acid was added and the sulfuric acid evaporated on an electric heater. After further cooling to room temperature, approximately 0.5 ml of sulfuric acid was added, and ultrapure water was added to make a total volume of 50 ml, which was used as the measurement sample. (1-4) Pretreatment (when measuring K element content) 0.5 g of the non-volatile component of the synthetic fiber treatment agent (or an amount such that the amount of potassium in the non-volatile component of the synthetic fiber treatment agent is 1 to 100 ppm) was weighed into a platinum crucible. After burning the organic components on an electric heater, approximately 5 ml of sulfuric acid was added and the mixture was gradually heated. After the sulfuric acid evaporated, the mixture was ashed in an electric furnace at 800 to 850°C. After cooling to room temperature, approximately 0.5 ml of nitric acid was added, and ultrapure water was added to make a total volume of 50 ml, which was used as the measurement sample. (1-5) Pretreatment (when measuring Na element content) 0.5 g of the non-volatile component of the synthetic fiber treatment agent (or an amount such that the amount of Na element in the non-volatile component of the synthetic fiber treatment agent is 1 to 100 ppm) was weighed into a platinum crucible. After burning the organic components on an electric heater, approximately 5 ml of sulfuric acid was added and the mixture was gradually heated. After the sulfuric acid evaporated, the mixture was ashed in an electric furnace at 800 to 850°C. After cooling to room temperature, approximately 0.5 ml of nitric acid was added, and ultrapure water was added to make a total volume of 50 ml, which was used as the measurement sample. (1-6) Pretreatment (when measuring Si element content) Approximately 0.5 g of the non-volatile content of the synthetic fiber treatment agent (or an amount such that the Si element content in the non-volatile content of the synthetic fiber treatment agent is 1 to 100 ppm) was weighed into a platinum crucible, 4 ml of sulfuric acid was added, and the organic components were burned on an electric heater. The mixture was then 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 the mixture was melted at 850°C. After dissolving the alkaline flux in water, ultrapure water was added to make a total volume of 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 solutions were subjected to ICP (International Classification of Radiation Spectrometer) testing (measurement instrument: Shimadzu ICPS-8100), and calibration curves were created using each standard solution. (3) Measurement The above-mentioned sample was subjected to ICP (measurement instrument name: Shimadzu Corporation ICPS-8100, ICP emission spectrometer), and the content of P, Zr, Ti, K, Na, and Si elements in the nonvolatile components of the synthetic fiber treatment agent was measured using the calibration curve prepared in (2) above.

[0110] (sulfate ions (SO4) 2- )·Chloride ions (Cl - (Measurement method) 5g of the sample (non-volatile component of the treatment agent) was accurately weighed, and 95g of ultrapure water was gradually added while stirring to prepare an aqueous solution, which was then brought to a final volume in a 100ml volumetric flask. 2ml 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 identified. 2- ), chloride ions (Cl - The amount of ) was converted. <Ion chromatograph conditions> Equipment: 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 4.0mm x length 250mm Eluent: 3.5 mmol Na2CO3, 1.0 mmol NaHCO3 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 component (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 trioerytherate A6-1: Polyethylene glycol (molecular weight 400) monolaurate (unpurified) A6-2: Polyethylene glycol (molecular weight 400) monolaurate A6-3: Lauryl alcohol EO7 molar adduct laurate A6-4: EO20 molar adduct of sorbitan trioleate A6-5: Tristearate, an EO43 molar adduct of castor oil A6-6: EO43 molar adduct of castor oil A6-7: EO10 molar adduct of laurate

[0112] <Nonionic surfactant (B) having a polyoxyalkylene skeleton without ester bonds> 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 EO7 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: Potassium oleate salt C1-4: Potassium octyl succinate C1-5: Cetyl phosphate K salt

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

[0115] <Manufacturing Example 1 (Manufacturing 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 mixture was stirred and the temperature was gradually raised to 180°C for 10 hours to carry out the esterification reaction, yielding 2-ethylhexyl alcohol stearate ester (without purification treatment) A1-1. The strong acid value was 0.7 mg KOH / g.

[0116] <Manufacturing Example 2 (Manufacturing of A1-2)> In a reaction vessel, 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. Under a nitrogen atmosphere, the mixture was stirred and the temperature was gradually raised to 240°C for 10 hours to carry out the esterification reaction, yielding 2-ethylhexyl alcohol stearate ester (Zr catalyst) A1-2. The strong acid value was 0 mg KOH / g.

[0117] <Manufacturing Example 3 (Manufacturing of A1-3)> 2-ethylhexyl alcohol stearate ester (Ti catalyst) A1-3 was obtained using the same manufacturing method as in Manufacturing 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] <Manufacturing Example 4 (Manufacturing of A1-4)> 1000 g of the above-mentioned 2-ethylhexyl alcohol stearate ester (unpurified) A1-1 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 2-ethylhexyl alcohol stearate ester A1-4. The strong acid value was 0 mg KOH / g.

[0119] <Manufacturing Example 5 (Manufacturing 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. The same washing treatment was then repeated. The oil layer was then dehydrated at 130°C for 2 hours while stirring under a nitrogen atmosphere. Finally, 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 mgKOH / g.

[0120] <Manufacturing Example 6 (Manufacturing of A1-6)> Lauryl alcohol oleate ester A1-6 was obtained using the same manufacturing method as in Manufacturing 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] <Manufacturing Example 7 (Manufacturing of A6-1)> Polyethylene glycol (molecular weight 400) monolaurate (without purification treatment) A6-1 was obtained using the same manufacturing method as in Manufacturing 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] <Manufacturing Example 8 (Manufacturing of A6-2)> 1000g of polyethylene glycol (molecular weight 400) monolaurate (unpurified) A6-1 and 20g 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, 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 mgKOH / g.

[0123] <Manufacturing Example 9 (Manufacturing 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, and B-9 can be produced by known methods. They are 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 obtained by 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] <Manufacturing Example 10 (Manufacturing of A6-3)> In a reaction vessel, 790 g (1.6 mol) of the above-mentioned lauryl alcohol EO7 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. Under a nitrogen atmosphere, the temperature was gradually raised to 190°C while stirring, and the esterification reaction was carried out for 10 hours. Subsequently, 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 EO7 molar adduct laurate A6-3. The strong acid value was 0 mg KOH / g.

[0125] <Manufacturing Example 11 (Manufacturing 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. Under a nitrogen atmosphere, the temperature was gradually raised to 190°C while stirring, and the esterification reaction was carried out for 10 hours. Subsequently, 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] [Table 1]

[0127] [Table 2]

[0128] [Table 3]

[0129] [Table 4]

[0130] As can be seen from Tables 1 to 4, the synthetic fiber treatment agent in the examples is the synthetic fiber treatment agent of the present invention, containing an ester component (A) and a nonionic surfactant (B) that does not have ester bonds but has a polyoxyalkylene skeleton, and the strong acid value and saponification value of the nonvolatile components of the treatment agent are within a specific range, and satisfy specific conditions 1 and 2 regarding the residual rate after heating, and therefore exhibits excellent reduction of thermal degradation and suppression of tension fluctuations even under harsh conditions, and has excellent durability in reducing the amount of thermal degradation and suppressing tension fluctuations. On the other hand, the comparative example, being not a synthetic fiber treatment agent of the present invention, exhibited inferior reduction in the amount of thermally degraded material and suppression of tension fluctuations. Furthermore, in the comparative evaluation, all treatment agents met the acceptable standards for reducing the amount of thermally degraded material and suppressing tension fluctuations. [Industrial applicability]

[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, The ester component (A) comprises 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. 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 non-volatile component of the aforementioned treatment agent is 0.00 to 0.10 mg KOH / g. The saponification value of the non-volatile components of the aforementioned treatment agent is 2 to 20 mg KOH / g. The iodine value of the non-volatile components of the aforementioned treatment agent is 0 to 8.

6. The total content of Zr and Ti elements in the nonvolatile matter of the aforementioned treatment agent is 0 to 54 ppm. The total content of K element and Na element in the nonvolatile matter of the aforementioned treatment agent is 50 to 2000 ppm. A method for producing a treatment agent for synthetic fibers, characterized in that the content of Si element in the nonvolatile matter of the treatment agent is 50 to 2000 ppm. Condition 1: The remaining percentage of the 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 residual amount of the 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. 【Chemistry 1】 (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.)

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