JP2012127020A - Fiber treating agent - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a fiber treating agent that has a low melting point of a lubricating component and excellent handleability, and is excellent in lubricity, heat resistance, and emulsion stability in water system.SOLUTION: Provided is a fiber treating agent containing an ester compound represented by the following general formula (1). R-O-((EO)-(PO))-(EO)-CO-R(1) (In the formula, Rrepresents a 8-24C hydrocarbon group, Rrepresents a 7-23C alkyl, alkenyl or cyclo alkyl group, EO represents an ethyleneoxy group, PO represents a propyleneoxy group. l and n are an average added mole number of an ethyleneoxy group, l is a number of 0-15, and n is a number of 1-20. m is an average added mole number of a propyleneoxy group and is a number of 0.5-20. The addition form of (EO)and (PO)in ((EO)-(PO)) may be any of random bond and block bond, and ((EO)-(PO)) and (EO)are block bonded in this order.)

Description

  The present invention relates to a fiber treating agent. In more detail, it is related with the processing agent for fibers used for the manufacturing process and processing process of a fiber accompanying a heat process.

  In the fiber manufacturing process, a fiber treating agent that imparts lubricity, bundling properties, antistatic properties and the like to the fiber is used in accordance with the purpose in order to allow fiber spinning and drawing to proceed smoothly. For example, as a lubricating component for fibers, paraffinic hydrocarbons such as mineral oil, oleyl oleate, dioleyl adipate, dioleyl dipropionate and the like are conventionally known.

  In recent years, the spinning speed tends to be further increased, and there is a demand for a fiber treatment agent that is excellent in heat resistance with little occurrence of yarn breakage and fluffing in the spinning process and less decomposition and smoke generation.

  Regarding a lubricating component for fibers, Patent Document 1 discloses an ester of a bisphenol alkylene oxide adduct as a lubricating component having a good heat resistance with little decomposition and smoke generation. Patent Document 2 discloses a technique using an ester compound of 1,2,3,4-butenetetracarboxylic acid as a treatment agent for fibers having good heat resistance. Patent Document 3 discloses an ester and thiol having a phenol skeleton. A technique using a dipropionate in combination is disclosed.

Japanese Patent Publication No. 47-29474 JP-A-6-228866 Japanese Patent Laid-Open No. 10-245781

  In the case where the fiber treatment agent is aqueous, the emulsion treatment stability of the fiber treatment agent is required to uniformly attach the lubricating component to the fiber. In this regard, as described in Patent Document 2 above, the emulsifier component (surfactant, etc.) causes water viscosity and causes thread breakage, or due to the low heat resistance of the emulsifier component itself. Since a smoke generation phenomenon may be caused, there is a demand for a treatment agent that can form an emulsion having good emulsification stability with a small amount of an emulsifier component. Furthermore, if the melting point of the lubricating component used in the fiber treatment agent is high, the lubrication performance deteriorates, and the stability and handleability of the treatment agent deteriorate, so the lubrication is low and the liquid is liquid at room temperature (20 ° C.). There is a need for fiber treating agents using components.

  However, with respect to conventional fiber treatment agents including the techniques described in Patent Documents 1 to 3, there has been no treatment agent that satisfies all of these characteristics.

  Accordingly, an object of the present invention is to provide a fiber treating agent having a low melting point of a lubricating component and excellent handleability and excellent lubricity, heat resistance, and emulsion stability in an aqueous system.

  As a result of earnestly examining the above problems, the present inventors added an alkylene oxide in a specific form to an alcohol having a specific chain length, and further using an ester compound obtained by converting it to an ester with a fatty acid as a lubricating component. The present inventors have found that the above problems can be solved and have completed the present invention.

That is, this invention provides the processing agent for fibers containing the ester compound represented by following General formula (1).
R ¹ —O — ((EO) ₁ — (PO) _m ) — (EO) _n —CO—R ² (1)
[Wherein, R ¹ represents a hydrocarbon group having 8 to 24 carbon atoms, R ² represents an alkyl group, alkenyl group or cycloalkyl group having 7 to 23 carbon atoms, EO represents an ethyleneoxy group, and PO represents a propyleneoxy group. l and n are average addition mole numbers of an ethyleneoxy group, 1 is 0-15, n is a number of 1-20. m is an average addition mole number of a propyleneoxy group, and is a number of 0.5-20. The addition form of (EO) _l and (PO) _m in ((EO) _1- (PO) _m ) may be either random coupling or block coupling. ((EO) _l- (PO) _m ) and ( EO) _n is block-coupled in this order. ]

  According to the present invention, there is provided a fiber treating agent that has a low melting point of a lubricating component and is liquid at room temperature, exhibits good handleability, and is excellent in all of lubricity, heat resistance, and emulsion stability in an aqueous system. Can do. Such a fiber treating agent is excellent in handleability at low temperatures, can be uniformly attached to the fiber yarn, and can be easily washed and removed in the scouring washing performed before the dyeing process, etc. Greatly contributes to

  The fiber treating agent of the present invention contains an ester compound represented by the general formula (1).

In the general formula (1), R ¹ is a hydrocarbon group having 8 to 24 carbon atoms, preferably a hydrocarbon group having 10 to 22 carbon atoms, and more preferably a hydrocarbon group having 12 to 18 carbon atoms. Examples of the hydrocarbon group for R ¹ include a linear or branched alkyl group, an alkenyl group, or an aromatic hydrocarbon group that may be substituted with a linear or branched alkyl group or alkenyl group. From the viewpoint of lubricity under conditions, a primary linear alkyl group or an alkenyl group is preferable, and a primary linear alkyl group is particularly preferable. From the viewpoint of lubricity and environmental safety, R ¹ is preferably hydroxy from natural higher alcohols such as octyl alcohol, decyl alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, eicosyl alcohol, behenyl alcohol, oleyl alcohol and the like. It is preferable that the residue is a group in which one group is removed. Among them, from the viewpoint of lubricity under high-speed winding conditions, lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, eicosyl alcohol, behenyl alcohol and oleyl More preferred is a residue obtained by removing one hydroxy group from an alcohol selected from alcohols, such as lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol and oleyl alcohol. A residue obtained by removing one hydroxy group from an alcohol selected from chol is more preferred, and a residue obtained by removing one hydroxy group from an alcohol selected from lauryl alcohol, myristyl alcohol, cetyl alcohol and stearyl alcohol is particularly preferred.

In the general formula (1), R ² is an alkyl group, alkenyl group or cycloalkyl group having 7 to 23 carbon atoms, preferably a linear alkyl group or alkenyl group having 7 to 23 carbon atoms, more preferably carbon. A linear alkyl group or alkenyl group having 9 to 21 carbon atoms, particularly preferably a linear alkyl group or alkenyl group having 11 to 17 carbon atoms. Preferable specific examples of R ² include a residue obtained by removing one carboxy group from a linear or branched, saturated or unsaturated fatty acid. Among them, from the viewpoint of lubricity, octanoic acid, decanoic acid, Lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, palmitoleic acid, petrothelic acid, oleic acid, elaidic acid, linoleic acid, linolenic acid, erucic acid, isopalmitic acid (2-hexyldecanoic acid), 2 -Residues obtained by removing one carboxy group from a fatty acid selected from heptylundecanoic acid, citronellic acid and isostearic acid are preferred. Decanoic acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, palmitoleic acid , Fat selected from petrothelic acid, oleic acid, elaidic acid and erucic acid A residue obtained by removing one carboxy group from a fatty acid is more preferred, and a residue obtained by removing one carboxy group from a fatty acid selected from lauric acid, myristic acid, palmitic acid, stearic acid and oleic acid is particularly preferred.

  In the general formula (1), l is a number of 0 to 15, preferably 0 to 5, more preferably 0 to 3, and particularly preferably 0 from the viewpoint of lubricity.

  N in the general formula (1) is a number of 1 to 20, preferably 2 to 15, more preferably 3 to 12, and particularly preferably 4 to 10 from the viewpoint of emulsion stability.

  M in the general formula (1) is a number of 0.5 to 20, preferably 0.8 to 15, more preferably 1 to 10, and particularly preferably 1.2 to 8 from the viewpoint of lubricity. .

In the general formula (1), - additional type of ((EO) _l (PO) _m) in the (EO) _l and (PO) _m may be random binding in block binding. From the viewpoint of keeping the melting point low, it is more preferable to use a block bond addition type.

When the effect of the present invention are the compounds of formula (1), - it is important that blocking binding to the ((EO) _l (PO) _m) and (EO) _n and this order. Since ((EO) _1- (PO) _m ) and (EO) _n are block-bonded in this order, the ester compound represented by the general formula (1) exhibits a low melting point and improves handling. In addition to contributing, the fiber treating agent containing the ester compound can exhibit good performance in all of lubricity, heat resistance, and emulsion stability in water.

  The ester compound represented by the general formula (1) can be obtained, for example, by the following production method.

That is, the following general formula (2):
R ¹ —OH (2)
(In the formula, R ¹ has the above-mentioned meaning.)
A catalyst such as a known acid or base is added to one or two or more alcohols represented by the formula, and dehydration under reduced pressure at 20 to 140 ° C. as necessary. Then, 1) propylene oxide is added alone, 2) propylene oxide is added after adding ethylene oxide, or 3) random addition of ethylene oxide and propylene oxide, and further ethylene oxide is added. As a result, a corresponding alkylene oxide adduct is obtained. Here, as an addition condition of the alkylene oxide, it is preferable to perform an operation (aging operation) for continuing the reaction at a temperature of 80 to 180 ° C. after introducing a predetermined amount of the alkylene oxide until the pressure decreases and becomes constant. . After obtaining the alkylene oxide adduct, the catalyst is neutralized if necessary, and further, the catalyst is removed by filtration using an alkali adsorbent or the like if necessary. Thereafter, an alkylene oxide adduct and the following general formula (3):
R ² -COOM (3)
(In the formula, R ² represents the same meaning as described above, and M represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.)
1 type or 2 types or more of fatty acids or fatty acid esters represented by the above, if necessary, using a known metal, acid, base, etc. catalyst according to a conventional method, esterification reaction or transesterification reaction, if necessary Thus, an ester compound represented by the general formula (1) can be obtained by performing a purification operation such as catalyst removal or steaming with an adsorbent or the like.

  The form of the fiber treating agent of the present invention may be a liquid oil containing the ester compound represented by the general formula (1) [hereinafter referred to as the ester compound (1)] or the ester compound (1). May be an aqueous emulsion obtained by emulsifying water in an aqueous medium selected from water and a mixture of water and a water-soluble organic solvent (for example, ethanol, isopropanol, etc.). Since the ester compound (1) tends to exhibit self-emulsifying properties in an aqueous medium, the amount of the emulsifier component used together can be reduced, and it can be uniformly attached to the fiber without separating other function-imparting agents. Further, from the viewpoint of easy control of the amount of treatment agent attached to the fiber, it is preferable to treat the fiber in the form of an aqueous emulsion.

  The content of the ester compound (1) in the fiber treating agent of the present invention is preferably from 3 to 70% by mass, more preferably from 4 to 50% by mass, particularly preferably from the viewpoint of imparting sufficient lubricity to the fiber. Is preferably 5 to 25% by mass.

  The fiber treating agent of the present invention can suitably contain one or more selected from emulsifier components and other function-imparting agents.

  As the emulsifier component, known emulsifier components such as nonionic surfactants, anionic surfactants and nitrogen-containing compounds can be suitably used. The nonionic surfactant is not particularly limited and known ones can be used. For example, hydrogenated castor oil alkylene oxide adducts; higher alcohols, alkylphenols, esters of polyhydric alcohols, and alkylene oxides thereof. Examples include adducts. The anionic surfactant is not particularly limited and known ones can be used. For example, fatty acid salts such as stearic acid, oleic acid and erucic acid, alkyl sulfonates, alkyl benzene sulfonates, and alkyl sulfates. Examples thereof include ester salts and alkyl phosphate ester salts. Examples of nitrogen-containing compounds include cationic surfactants such as alkyl quaternary ammonium salts, alkyl hydroxyethyl ammonium salts, and imidazolinium salts, and amphoteric interfaces such as aliphatic alkanolamides, aliphatic amine ethylene oxide adducts, and alkyl betaines. An activator is mentioned.

  Since the ester compound (1) exhibits self-emulsifying properties, the fiber treatment agent of the present invention containing the ester compound (1) obtains a stable emulsion using less emulsifier components than the usual use amount. be able to. That is, the content of the emulsifier component in the fiber treating agent of the present invention can be adjusted in the range of 0 to 50% by mass, preferably 0.1 to 20% by mass. For example, the content of the emulsifier component Can be obtained even when the content is reduced to a range of 0.1 to 5% by mass, and further, an emulsion exhibiting good emulsification stability can be obtained. Even when it is lowered to this range, it is possible to obtain an emulsion exhibiting good emulsification stability.

  Other function-imparting agents that can be suitably used in the fiber treating agent of the present invention include smooth oils such as ester oils such as isostearyl isostearate, isostearyl adipate, trimethylolpropane trilaurate, and mineral oils such as liquid paraffin. Agent, unmodified or ether-modified, amino-modified, epoxy-modified or glycol-modified silicone resin, polyacrylic ester, polyvinyl alcohol, paste ester such as terminal esterified product or etherified product of ethylene oxide adduct of bisphenol A, carbon number The component normally used for fiber treatment agents, such as extreme pressure additives, such as an alkylamine of 8-22 and its ethylene oxide adduct, a rust preventive, a preservative, and an antioxidant, can be mentioned. The content of these function-imparting agents can be appropriately determined according to the purpose within a range that does not impair the effects of the present invention.

  The method for adhering (oiling) the fiber treating agent of the present invention to the fiber is not particularly limited, and a known method such as a dipping method or a spray method can be used.

  From the viewpoint of imparting sufficient lubricity to the fiber, the amount of the fiber treating agent attached to the fiber is preferably 0.02 to 5 parts by mass with respect to 100 parts by mass of the fiber in terms of the ester compound (1). It is preferably 0.1 to 3 parts by mass, more preferably 0.3 to 2 parts by mass.

  Fibers to which the fiber treating agent of the present invention can be applied include synthetic fibers such as polyester, polyamide, polyacryl, polypropylene, polyvinyl alcohol, polyvinyl chloride, polyvinylidene chloride, polyurethane, semi-synthetic fibers such as acetate, and the like. And mixed fibers of cotton, hemp, rayon, wool, and other natural fibers, and fibers made by dispersing inorganic compounds such as titania, zirconia, alumina, silica, and zeolite in synthetic fibers. May be added with a matting agent, a fluorescent brightening agent, an antistatic agent and a flame retardant. Among these, the fiber treating agent of the present invention is effective for synthetic fibers that are generally heat-treated at high temperatures. The fiber treating agent of the present invention can also be applied to fields where conventional oil agents such as cotton, linen fabric and woolen fabric are used.

  The application time of the fiber treating agent of the present invention is not particularly limited as long as it is after the time when the spun yarn is solidified, but it is usually applied to the yarn before the take-up roller. The fiber treating agent of the present invention can uniformly adhere to the yarn when applied, and can be easily removed by scouring performed before the dyeing process.

  The obtained yarn is provided as a woven fabric or non-woven fabric for industrial materials such as a woven fabric for clothing, an adhesive tape reinforcing material, a wire coating material, a tent fabric, or a tire cord.

  The fiber treating agent of the present invention can be suitably used as a high-speed spinning oil or tire cord oil for synthetic fibers, but it is used for producing a drawing oil, a spinning direct-drawing oil, a spinning oil for producing textiles, a conning oil, and a woven fabric. It can be applied as a base oil such as a fiber entanglement oil for use as a composition in which an appropriate additive is blended.

  Hereinafter, the present invention will be described in detail with reference to examples. The ester compound used in the examples was produced by the following method. Further, unless otherwise specified, in the following description, “%” means “mass%”.

Production Example 1: Production of ester compound (A) In an autoclave equipped with a stirrer, a temperature control device, and an automatic introduction device, 1082 g (4.0 moles) of stearyl alcohol (calcol 8098, manufactured by Kao Corporation) as a raw material alcohol Then, 3.2 g (0.08 mol) of potassium hydroxide was charged, dehydrated at 110 ° C. and 1.3 kPa for 30 minutes, and then purged with nitrogen. Thereafter, as an addition reaction of propylene oxide, the temperature was raised to 125 ° C., and 580.8 g (10.0 mol) of propylene oxide was introduced for aging operation. Next, in the addition reaction of ethylene oxide, the temperature was raised to 150 ° C., 881 g (20 mol) of ethylene oxide was introduced, and an aging operation was performed. After completion of the reaction, the mixture was cooled to 80 ° C., 9.6 g of 90% lactic acid was added to the autoclave, and the mixture was stirred at 80 ° C. for 30 minutes, and then extracted to obtain an alkylene oxide adduct. From the hydroxyl value of the product, it was confirmed that the number of added moles of propylene oxide and ethylene oxide was as charged. In addition, at each stage of the addition reaction, since the residual pressure becomes a constant value close to zero, it can be confirmed that all of propylene oxide and ethylene oxide have been consumed. Knew.
Next, in a four-necked flask equipped with a stirrer, a temperature controller, and a dehydration tube, 636 g (1 mol) of alkylene oxide adduct, 282.5 g of oleic acid (Lunac OLL-V, manufactured by Kao Corporation), catalyst 0.18 g of stannous oxide (0.02% by mass with respect to the total charged amount) was charged, and esterification was performed at 170 to 240 ° C. for 10 hours. After adding activated carbon (carbafine, Takeda Pharmaceutical Co., Ltd.) and activated clay corresponding to 0.4% by mass to the obtained esterification reaction product, mixing at 90 ° C., 5.33 kPa for 2 hours, Filtration gave an ester compound. The reaction rate of esterification was 97% (based on raw fatty acid). Table 1 shows the structural characteristics of the obtained ester compound.

Production Examples 2 to 18: Production of ester compounds (B) to (K) and comparative ester compounds (a) to (g) With respect to the raw material alcohol shown in Table 1, under the same addition reaction conditions as in Production Example 1 After an addition reaction in the order of ethylene oxide having an average addition mole number of 1, propylene oxide having an average addition mole number of m and ethylene oxide having an average addition mole number of n, an esterification reaction was performed using the raw fatty acids shown in Table 1. Except that the corresponding ester compounds (B) to (K) and comparative ester compounds (a) to (g) were produced using the same reaction apparatus, reaction operation and conditions as in Production Example 1. Table 1 shows the respective esterification reaction rates (based on raw fatty acids) and the structural characteristics of the obtained ester compounds.

Examples 1-11 and Comparative Examples 1-8
About the ester compound shown in Table 1, the external appearance property and heat resistance were evaluated by the following method. Moreover, the processing agent for fibers was prepared with the following method using the ester compound shown in Table 1, and the lubricity and emulsion stability were evaluated according to the following procedure. The results are summarized in Table 2.

[Evaluation of appearance properties]
An ester compound used as a lubricating component of a fiber treating agent is required to be liquid at the treatment temperature and to be excellent in handleability at room temperature (20 ° C.) in order to exhibit sufficient lubricity. In this evaluation test, the appearance properties at 20 ° C. (normal temperature) of each ester compound shown in Table 1 were determined according to the following criteria. The results are shown in Table 2.
Evaluation criteria:
○: Transparent liquid Δ: Precipitates but fluidity ×: Solid

[Evaluation of heat resistance]
When the ester compound used as a lubricating component of the fiber treating agent volatilizes or thermally decomposes at the processing temperature at the time of spinning, problems such as a smoke generation phenomenon and a decrease in lubricity occur. Therefore, it is required not to volatilize or thermally decompose at the spinning temperature (generally about 200 ° C.). In this evaluation test, the behavior of volatilization and thermal decomposition of each ester compound shown in Table 1 in a high temperature range was evaluated by thermogravimetric analysis. That is, using the differential thermal and thermogravimetric simultaneous measurement apparatus TG / DTA7200 manufactured by SII Nanotechnology, Inc., each ester compound shown in Table 1 was heated at an initial temperature of 20 ° C. to 10 ° C./min in an air stream. The temperature (T5) when a weight loss corresponding to 5% by weight of the initial weight occurred was measured and judged according to the following criteria. The results are shown in Table 2.
Evaluation criteria:
○: T5 is 200 ° C. or higher X: T5 is lower than 200 ° C.

[Evaluation of lubricity]
A 1000 ml glass beaker is charged with an amount of ion-exchanged water necessary for the finished mass of the fiber treatment agent to reach 500 g, and then 42.5 g of each ester compound shown in Table 1 (8.5 in the fiber treatment agent). Mass%), and surfactant polyoxyethylene (7) alkyl (sec-C _11-15 ) ether [Emulgen 707, manufactured by Kao Corporation] 5 g (1.0% by mass in the fiber treatment agent), lauryl 2.5 g of sulfate (0.5% by mass in the fiber treatment agent) was added and stirred at room temperature (25 ° C.) to prepare a fiber treatment agent in the form of an aqueous emulsion.
Test fibers (polyester filament yarn: 83 dtex, 36 filaments) were immersed in the obtained fiber treatment agent, and 1.5 parts by mass of the fiber treatment agent was adhered to 100 parts by mass of the fiber in terms of the amount of the ester compound. Thereafter, it was dried to obtain a test yarn.
Using this test yarn, a friction measuring machine (μ meter instrument TWD-4, manufactured by Eiko Sokki Co., Ltd.) was used to make a metal by the traveling yarn method with an initial tension of 20 gf, a yarn speed of 500 m / min, and a friction angle of 180 °. Contact with a pin (made of stainless steel) was performed, and the dynamic friction between the yarn and the metal when passing through the metal pin was measured 5 times, and the dynamic friction coefficient was calculated from the average value. The results are shown in Table 2. The smaller the value of the dynamic friction coefficient, the lower the friction and the better the lubricity.

[Evaluation of emulsion stability]
In a 500 ml glass beaker, an amount of ion-exchanged water necessary for the finished mass of the fiber treatment agent to be 300 g is added, and then 30 g of each ester compound shown in Table 1 (10% by mass in the fiber treatment agent), And surfactant polyoxyethylene (7) alkyl (sec-C _11-15 ) ether [Emulgen 707, manufactured by Kao Corporation] or polyoxyethylene (7) alkyl (C _12-13 ) ether [Emulgen 507, Kao Co., Ltd., β-methyl branching ratio of about 20%)] is added in an amount of 0.5 to 2.0% by mass in the fiber treating agent, and stirred at room temperature (25 ° C.) for aqueous emulsification. A liquid form fiber treating agent was prepared.
About the obtained fiber processing agent, the emulsified state after 1 day storage at 25 ° C. and after 7 days storage was determined according to the following criteria. The results are shown in Table 2.
Evaluation criteria:
○: Maintaining uniform emulsified state ×: Separated into two layers

  The fiber treating agent of the present invention using the ester compound having a specific structure represented by the general formula (1) is excellent in all of the appearance properties, heat resistance, lubricity, and emulsion stability in water. Furthermore, the fiber treatment agent of the present invention can be easily washed and removed in scouring washing, and greatly contributes to smoothing of the fiber production process.

Claims (13)

The processing agent for fibers containing the ester compound represented by following General formula (1).
R ¹ —O — ((EO) ₁ — (PO) _m ) — (EO) _n —CO—R ² (1)
[Wherein, R ¹ represents a hydrocarbon group having 8 to 24 carbon atoms, R ² represents an alkyl group, alkenyl group or cycloalkyl group having 7 to 23 carbon atoms, EO represents an ethyleneoxy group, and PO represents a propyleneoxy group. l and n are average addition mole numbers of an ethyleneoxy group, 1 is 0-15, n is a number of 1-20. m is an average addition mole number of a propyleneoxy group, and is a number of 0.5-20. The addition form of (EO) _l and (PO) _m in ((EO) _l- (PO) _m ) may be either random or block coupling, and ((EO) _l- (PO) _m ) and ( EO) _n is block-coupled in this order. ] The fiber treating agent according to claim 1, wherein R ¹ in the general formula (1) is a primary linear alkyl group or alkenyl group having 8 to 24 carbon atoms. The fiber treatment agent according to claim 1 or 2, wherein R ¹ in the general formula (1) is a primary linear alkyl group having 12 to 18 carbon atoms. R ² in the general formula (1) is an alkyl or alkenyl group linear 7 to 23 carbon atoms, fiber-processing agent of any one of claims 1 to 3. The fiber treatment agent according to any one of claims 1 to 4, wherein R ² in the general formula (1) is a primary linear alkyl group or alkenyl group having 11 to 17 carbon atoms.   The processing agent for fibers of any one of Claims 1-5 whose l in General formula (1) is 0-3.   The processing agent for fibers of any one of Claims 1-6 whose m in General formula (1) is 1-10.   The processing agent for fibers of any one of Claims 1-7 whose n in General formula (1) is 3-12.   Furthermore, the processing agent for fibers of any one of Claims 1-8 containing surfactant. Formula (1) in the - (EO) _l and (PO) _m in ((EO) _l (PO) _m) has blocked binding in this order, any one of the preceding claims The processing agent for textiles as described.   The treatment agent for fibers according to any one of claims 1 to 10, wherein the content of the ester compound represented by the general formula (1) is 3 to 70% by mass and further contains water.   The processing agent for fibers of any one of Claims 1-11 which is an object for synthetic fibers. After making the fiber processing agent of any one of Claims 1-12 adhere 0.1-3 mass parts with respect to 100 mass parts of fibers in conversion of the ester compound represented by General formula (1). A fiber processing method that performs stretching and winding.