TWI830199B - Treatment agents for synthetic fibers, synthetic fibers and treatment methods for synthetic fibers - Google Patents

Abstract

The object of the present invention is to provide a treatment agent for synthetic fibers that imparts good antistatic properties to synthetic fibers and is excellent in both emulsion stability and low-temperature operability, as well as synthetic fibers to which the treatment agent is attached, and the treatment agent for synthetic fibers. A treatment that adheres to synthetic fibers. The processing agent for synthetic fibers provided by the present invention contains at least one type of cycloalkyl alkanol derivatives represented by the following general formula (1) and general formula (2).

(In the formula, ring Q ^a : cycloalkylene group with 3 to 8 carbon atoms

R ^1a : Hydrogen atom or alkyl group with 1 to 12 carbon atoms

R ^2a : divalent hydrocarbon group with 1 to 12 carbon atoms

R ³ : Hydrogen atom, or the residue obtained by removing the hydroxyl group from a monocarboxylic acid having 6 to 22 carbon atoms.

A ^1a O: Alkyleneoxy group having 2 to 4 carbon atoms (however, when there are two or more alkyleneoxy groups, they may be one type alone or two or more types)

m ^a : an integer from 0 to 100; except when m ^a is 0 and R ³ is a hydrogen atom)

(In the formula, the rings Q ^b , R ^1b , R ^2b , A ^1b O, and m ^b are independently synonymous with the rings Q ^a , R ^1a , R ^2a , A ^1a O, and m ^a of the formula (1); R ⁴ : The residue obtained by removing two hydroxyl groups from a dicarboxylic acid having 4 to 12 carbon atoms; except when m ^b is 0).

Description

Treatment agents for synthetic fibers, synthetic fibers and treatment of synthetic fibers method

The present invention relates to a treatment agent for synthetic fibers, synthetic fibers and a method for treating synthetic fibers.

In recent years, as the spinning steps, false twisting steps, and post-processing steps of synthetic fibers have become faster, static electricity generation and yarn pilling are more likely to occur. In order to prevent the occurrence of such static electricity and pilling, measures have been taken to increase the content of functional enhancers that adhere to synthetic fibers as synthetic fiber treatment agents to prevent such occurrences, and to increase the content of synthetic fiber treatment agents. The amount of adhesion of the agent to synthetic fibers is still insufficient, and it is desired to further improve the antistatic properties.

On the other hand, synthetic fibers are produced in various countries and regions, and the conditions for use of synthetic fiber treatment agents are also diversified. For example, in terms of temperature conditions, there is a need for synthetic fiber treatment agents that can withstand a very wide temperature range. However, treatment agents for synthetic fibers containing polyethers (PO/EO copolymers) (for example, Patent Document 1) are known, but these treatment agents for synthetic fibers may have insufficient emulsion stability. If the emulsion stability of the synthetic fiber treatment agent is poor, for example, during storage in the emulsion preparation tank, the contained components may separate and adhere to the synthetic fibers. The synthetic fiber treatment agent will not adhere uniformly, causing problems in subsequent spinning. The cause of many problems in the filament step, false twisting step, and post-processing step. Furthermore, the low-temperature operability in an environment below freezing point is reduced, which may cause, for example, the coagulation of the treatment agent components for synthetic fibers, resulting in non-uniformity of the contained components and inability to fully function, or the time-consuming preparation and filling of the emulsion. . That is, improving the emulsion stability and low-temperature operability of treatment agents for synthetic fibers is an important issue as it is the key to improving the quality of synthetic fibers. [Prior technical literature] [Patent Document]

[Patent Document 1] Japanese Patent Application Laid-Open No. 10-245729

The object of the present invention is to provide a treatment agent for synthetic fibers that imparts good antistatic properties to synthetic fibers and is excellent in both emulsion stability and low-temperature operability, as well as synthetic fibers to which the treatment agent is attached, and the treatment agent for synthetic fibers. A treatment that adheres to synthetic fibers.

The inventor of this case conducted in-depth research to solve the above-mentioned problems and found that in order to provide good antistatic properties to synthetic fibers and prepare a synthetic fiber treatment agent with excellent emulsion stability and low-temperature operability, a cycloalkyl alkane with a specific chemical structure is needed. Alcohol derivatives have made great contributions to solving the above problems.

The specific gist of the present invention is as follows.

1. A treatment agent for synthetic fibers containing at least one selected from the cycloalkyl alkanol derivatives represented by the following general formula (1) and general formula (2);

(In the formula, ring Q ^a : cycloalkylene group with 3 to 8 carbon atoms

R ^1a : Hydrogen atom or alkyl group with 1 to 12 carbon atoms

R ^2a : divalent hydrocarbon group with 1 to 12 carbon atoms

R ³ : Hydrogen atom, or the residue obtained by removing the hydroxyl group from a monocarboxylic acid having 6 to 22 carbon atoms.

A ^1a O: Alkyleneoxy group having 2 to 4 carbon atoms (however, when there are two or more of the alkyleneoxy groups, they may be one type alone or two or more types)

m ^a : an integer from 0 to 100; except when m ^a is 0 and R ³ is a hydrogen atom)

(In the formula, the rings Q ^b , R ^1b , R ^2b , A ^1b O, and m ^b are independently synonymous with the rings Q ^a , R ^1a , R ^2a , A ^1a O, and m ^a of the formula (1); R ⁴ : The residue obtained by removing two hydroxyl groups from a dicarboxylic acid having 4 to 12 carbon atoms; however, excluding the case where m ^b is 0).

2. The treatment agent for synthetic fibers according to 1., which contains a cycloalkyl alkanol derivative in which R ^1a of the above general formula (1) is a hydrogen atom and R ^1b of the above general formula (2) is a hydrogen atom. One or more types of cycloalkyl alkanol derivatives selected from the group consisting of atoms.

3. The treatment agent for synthetic fibers according to 1. or 2., which contains a cycloalkyl alkanol derivative in which R ^2a of the general formula (1) is a divalent hydrocarbon group having 2 to 8 carbon atoms, and the above R ^2b in the general formula (2) is at least one selected from cycloalkyl alkanol derivatives of a divalent hydrocarbon group having 2 to 8 carbon atoms. 4. The treatment agent for synthetic fibers according to any one of 1. to 3., wherein R ³ in the general formula (1) is an aliphatic monocarboxylic acid having 6 to 22 carbon atoms in which a hydroxyl group has been removed. At least one selected from the cycloalkyl alkanol derivatives of the following residues and the cycloalkyl alkanol derivatives represented by the general formula (2) above. 5. The treatment agent for synthetic fibers according to any one of 1. to 4., wherein the cycloalkyl alkanol derivative contains 0.01 to 30% by mass relative to the total mass of the treatment agent for synthetic fibers. . 6. The treatment agent for synthetic fibers according to any one of 1. to 5., further containing: a nonionic surfactant (excluding the above-mentioned cycloalkyl alkanol derivatives) and an ionic interface. active agent. 7. The treatment agent for synthetic fibers according to any one of 1. to 5., further containing: a smoothing agent, a nonionic surfactant (except for the above-mentioned cycloalkyl alkanol derivatives) and Ionic surfactant. 8. The treatment agent for synthetic fibers according to 6. or 7., wherein the ionic surfactant contains an organic phosphate P1 represented by the following general formula (3) and an organic phosphate represented by the following general formula (4). Select at least one organic phosphate from the organic phosphate P2 represented by the following general formula (5) and the organic phosphate P3 represented by the following general formula (5); [Chemical 3] (In the formula, the rings Q ^c , R ^1c , R ^2c , A ^1c O, and m ^c are independently synonymous with the rings Q ^a , R ^1a , R ^2a , A ^1a O, and ma of the general formula (1); ⁿ : Integer R ⁵ from 2 to 4: The residue after removing the terminal oxygen atom from "R ^1c -ring Q ^c -R ^2c -O-(A ^1c O)m ^c -" (However, ring Q ^c , R ^1c , R ^2c , A ^1c O, m ^c are independently synonymous with the ring Q ^a , R ^1a , R ^2a , A ^1a O, ^ma of the general formula (1), alkali metals, and alkaline earth metals (1/2 ), organic amine salt or hydrogen atom M ¹ : alkali metal, alkaline earth metal (1/2), organic amine salt or hydrogen atom) [Chemical 4] (In the formula, rings Q ^d , R ^1d , R ^2d , A ^1d O(OA ^1d ), and m ^d are independently related to the rings Q ^a , R ^1a , R ^2a , A ^1a O, and m of the general formula (1), respectively. ^a is synonymous; M ² : alkali metal, alkaline earth metal (1/2), organic amine salt or hydrogen atom) [Chemical 5] (In the formula, the rings Q ^e , R ^1e , R ^2e , A ^1e O, and ^me are independently ^synonymous with the rings Q ^a , R ^1a , R ^2a , A ^1a O, and ma of the general formula (1); M ³ , M ⁴ : each independently an alkali metal, an alkaline earth metal (1/2), an organic amine salt or a hydrogen atom). 9. A synthetic fiber to which the treatment agent for synthetic fibers according to any one of 1. to 8. is adhered. 10. A method for treating synthetic fibers, wherein the treating agent for synthetic fibers according to any one of 1. to 8. is allowed to adhere to the synthetic fibers in an amount of 0.1 to 5% by mass.

The synthetic fiber treatment agent, synthetic fiber, and synthetic fiber treatment method of the present invention can respond to the recent increase in speed in the spinning step, false twisting step, and post-processing step of synthetic fibers, and utilize excellent antistatic properties to It can prevent static electricity and pilling. Furthermore, since the treatment agent for synthetic fibers of the present invention has excellent emulsion stability, the components contained in the emulsion do not separate even if the emulsion is stored for a long time, which contributes to uniform adhesion of the treatment agent for synthetic fibers. Furthermore, since the synthetic fiber treatment agent of the present invention is excellent in low-temperature operation in an environment below freezing point, problems such as coagulation of components of the synthetic fiber treatment agent do not occur, and there is no need to waste time in preparing and filling the emulsion.

The present invention relates to a synthetic fiber treatment agent containing at least one selected from the cycloalkyl alkanol derivatives represented by the general formula (1) and the general formula (2), a synthetic fiber to which the treatment agent is adhered, and A treatment method in which the treatment agent for synthetic fibers is adhered to synthetic fibers. Hereinafter, the present invention will be described in detail.

<Cycloalkyl alkanol derivatives> The treatment agent for synthetic fibers of the present invention contains one or more types of cycloalkyl alkanol derivatives represented by the following general formula (1) and the following general formula (2). as an essential ingredient. [Chemical 6] (In the formula, Ring Q ^a : cycloalkylene group with 3 to 8 carbon atoms

R ^1a : Hydrogen atom or alkyl group with 1 to 12 carbon atoms

R ^2a : divalent hydrocarbon group with 1 to 12 carbon atoms

R ³ : Hydrogen atom, or the residue obtained by removing the hydroxyl group from a monocarboxylic acid having 6 to 22 carbon atoms.

A ^1a O: Alkyleneoxy group having 2 to 4 carbon atoms (however, when there are two or more of the alkyleneoxy groups, they may be one type alone or two or more types)

m ^a : an integer from 0 to 100; except when m ^a is 0 and R ³ is a hydrogen atom)

(In the formula, rings Q ^b , R ^1b , R ^2b , A ^1b O and m ^b are independently synonymous with ring Q ^a , R ^1a , R ^2a , A ^1a O and ma ^of formula (1), R ⁴ : The residue obtained by removing the hydroxyl group from a dicarboxylic acid having 4 to 12 carbon atoms; except when m ^b is 0)

The cycloalkyl alkanol derivative represented by the general formula (1) of the present invention is an alkylene oxide addition polymer of a monocarboxylic acid cycloalkyl alkanol ester with a carbon number of 6 to 22 and a cycloalkyl alkanol. Or an ester of an alkylene oxide addition polymer of a monocarboxylic acid with a carbon number of 6 to 22 and a cycloalkyl alkanol. The cycloalkyl alkanol derivative represented by the general formula (2) of the present invention is a carbon number of 4 to 12 Diester of dicarboxylic acid cycloalkyl alkanol, or diester of alkylene oxide addition polymer of dicarboxylic acid with 4 to 12 carbon atoms and cycloalkyl alkanol.

Ring Q ^a in the above general formula (1) and ring Q ^b in the general formula (2) are preferably independently cycloalkyl groups with 5 to 8 carbon atoms, more preferably cycloalkyl groups with 5 or 6 carbon atoms. .

R ^1a in the above general formula (1) and R ^1b in the general formula (2) are preferably each independently a hydrogen atom or an alkyl group having 6 to 10 carbon atoms, more preferably a hydrogen atom or an alkyl group having 6 to 8 carbon atoms. The base and especially preferably are hydrogen atoms.

The divalent hydrocarbon groups having 1 to 12 carbon atoms in R ^2a in the general formula (1) and R ^2b in the general formula (2) may be independently linear or branched, or may be Either saturated or unsaturated. Among them, an independently linear or branched chain alkylene group having 1 to 12 carbon atoms is preferred, a linear or branched chain alkylene group having 2 to 8 carbon atoms is more preferred, and a particularly preferred one is a linear or branched chain alkylene group having 2 to 8 carbon atoms. A straight-chain alkylene group with 2 to 8 carbon atoms.

The hydrogen atom of ^R3 in the above general formula (1), or the monocarboxylic acid in the residue after removing the hydroxyl group from a monocarboxylic acid having 6 to 22 carbon atoms, may be a saturated monocarboxylic acid or an unsaturated monocarboxylic acid. Any of them. Among them, it is preferably a hydrogen atom or a residue obtained by removing a hydroxyl group from a saturated/unsaturated monocarboxylic acid having 8 to 20 carbon atoms, and more preferably a residue obtained by removing a hydroxyl group from a saturated/unsaturated monocarboxylic acid having 8 to 20 carbon atoms. the remaining residues.

In the above general formula (2), the dicarboxylic acid in the residue obtained by removing two hydroxyl groups from a dicarboxylic acid having 4 to 12 carbon atoms in R ⁴ can be a saturated or unsaturated aliphatic dicarboxylic acid. Any of aromatic dicarboxylic acids. Among them, the residue obtained by removing two hydroxyl groups from a saturated or unsaturated aliphatic dicarboxylic acid having 4 to 12 carbon atoms is more preferred, and a residue obtained by removing the saturated aliphatic dicarboxylic acid having 4 to 12 carbon atoms is more preferred. The residue after the 2 hydroxyl groups.

When A ^1a O in the general formula (1) and A ^1b O in the general formula (2) are two or more types of alkyleneoxy groups having 2 to 4 carbon atoms, each independently may be randomly dispersed or may be Blocks may also be a mixture of these. Among them, preferred are one or two types of alkyleneoxy groups each independently having 2 or 3 carbon atoms.

m ^a in the general formula (1) and m ^b in the general formula (2) represent the average molar number of the alkyleneoxy group having 2 to 4 carbon atoms, and are preferably each independently an integer of 0 to 20. More preferably, it is an integer from 0 to 15 (except for the case where m ^a is 0 and R ³ is a hydrogen atom in the general formula (1), and except for the case where m ^b is 0 in the general formula (2)).

The cycloalkyl alkanol derivatives represented by the general formula (1) and general formula (2) of the present invention are made by, for example, the esterification reaction of cycloalkyl alkanol and monocarboxylic acid or dicarboxylic acid; Addition polymerization of alkylene oxides with 2 to 4 carbon atoms in alkanols by random, block or mixed methods; or alkylene oxide addition polymers of the above-mentioned cycloalkanols and monocarboxylic acids or It is produced by esterification reaction of dicarboxylic acid.

The treatment agent for synthetic fibers of the present invention preferably contains 0.01 to 30 mass % of the cycloalkyl alkanol derivatives represented by the general formula (1) and the general formula (2), and more preferably 0.1 to 30 mass % of the total mass. 25 mass %, particularly preferably 0.2 to 20 mass %, and more preferably 0.2 to 10 mass %. Furthermore, the treatment agent for synthetic fibers of the present invention preferably contains a nonionic surfactant and an ionic surfactant other than the cycloalkyl alkanol derivative represented by the above general formula (1) and general formula (2). agent. Furthermore, the treatment agent for synthetic fibers of the present invention preferably contains a nonionic surfactant, a smoothing agent, and an ionic surfactant other than the cycloalkyl alkanol derivative represented by the above general formula (1) and general formula (2). Surfactants. For the treatment agent for synthetic fibers of the present invention, nonionic surfactants, smoothing agents and ionic interfaces other than the cycloalkyl alkanol derivatives represented by the general formula (1) and the general formula (2) can be used together. Active agents are described.

<Nonionic surfactants other than cycloalkyl alkanol derivatives> There are no particular limitations on the nonionic surfactants other than the cycloalkyl alkanol derivatives represented by the general formula (1) and the general formula (2) that can be used together with the treatment agent for synthetic fibers of the present invention. Examples thereof Such as: (1) Polyoxyethylene oleate, polyoxyethylene methyl ether laurate, polyoxyethylene octyl ether laurate, polyoxyethylene polyoxypropylene tridecyl ether palmitate, polyoxyethylene dioleic acid Ester, polyoxyethylene lauryl ether, polyoxypropylene lauryl ether methyl ether, polyoxybutyl oleyl ether, polyoxyethylene polyoxypropylene butyl ether, polyoxyethylene polyoxypropylene octyl ether, polyoxyethylene polyoxypropylene trihydroxy Methyl propyl ether, polyoxyethylene polyoxypropylene nonyl ether, polyoxyethylene polyoxypropylene propylene glycol ether, polyoxyethylene polyoxypropylene lauryl ether, polyoxyethylene polyoxypropylene isotridecyl ether, polyoxyethylene tetradecane Ether, polyoxyethylene glyceryl ether, polyoxyethylene lauryl amine ether, polyoxyethylene lauryl amide ether, etc., have carbon numbers 2 to 4 added to organic acids, organic alcohols, organic amines and/or organic amide molecules. Alkylene oxide compounds; (2) Polyoxyalkylene sorbitan trioleate, polyoxyalkylene castor oil ether, polyoxyalkylene hardened castor oil ether, polyoxyalkylene hardened castor Polyoxyalkylene polyol fatty acid esters such as sesame oil trioleate; (3) Alkyl amide such as diethanolamine monolaurylamide; (4) Polyoxyalkylene glycol amide such as polyoxyethylene diethanolamine monooleyl amide Alkyl fatty acid amide, etc. These nonionic surfactants may be used individually by 1 type, or may be used in combination of 2 or more types. In the present invention, those with EO and PO recorded at the end of the compound name refer to the adduct of ethylene oxide and propylene oxide respectively, and the following number indicates the molar number of addition. The values recorded after EO and PO refer to the respective average added moles.

＜Smoothing agents other than cycloalkyl alkanol derivatives＞ The treatment agent for synthetic fibers of the present invention can be used together with smoothing agents other than the cycloalkyl alkanol derivatives represented by the general formula (1) and the general formula (2). Examples thereof include: (1) butyl stearate Ester, octyl stearate, oleyl laurate, oleyl oleate, isostearate, octyl palmitate, isotridecyl stearate, lauryl caprylate and other aliphatic monoalcohols and fats Ester compounds of monocarboxylic acids; (2) 1,6-hexanediol didecanoate, trimethylolpropane monooleate monolaurate, sorbitan trioleate, sorbitan anhydride Aliphatic polyols and aliphatic monocarboxylates such as monooleate, sorbitan tristearate, sorbitan distearate, sorbitan monostearate, glyceryl monolaurate, etc. Ester compounds of acids; (3) Aliphatic monoalcohols and fats such as dilauryl adipate, dioleyl azelate, diisocetylthiodipropionate, and bispolyoxyethylene lauryl adipate Ester compounds of polycarboxylic acids; (4) Ester compounds of aromatic monoalcohols and aliphatic monocarboxylic acids such as benzyl oleate, benzyl laurate and polyoxypropylene benzyl stearate; (5) bis Ester compounds of aromatic polyols such as phenol A dilaurate and polyoxyethylene bisphenol A dilaurate and aliphatic monocarboxylic acids; (6) Bis(2-ethylhexyl phthalate), isophthalic acid Ester compounds of aliphatic monoalcohols such as diisostearate and trioctyl trimellitate and aromatic polycarboxylic acids; (7) Coconut oil, rapeseed oil, sunflower oil, soybean oil, castor oil, sesame oil, fish oil and natural fats such as tallow; (8) well-known smoothing agents used in synthetic fiber treatment agents such as mineral oil. These smoothing agent components may be used individually by 1 type, or in combination of 2 or more types.

<Ionic surfactant> The treatment agent for synthetic fibers of the present invention is preferably a combination of an organic phosphate P1 represented by the following general formula (3), an organic phosphate P2 represented by the following general formula (4), and the following Among the organic phosphates P3 represented by the general formula (5), at least one organic phosphate is selected as the ionic surfactant. [Chemical 8] (In the formula, the rings Q ^c , R ^1c , R ^2c , A ^1c O, and m ^c are independently synonymous with the rings Q ^a , R ^1a , R ^2a , A ^1a O, and ma of the general formula (1); ⁿ : Integer R ⁵ from 2 to 4: The residue after removing the terminal oxygen atom from "R ^1c -ring Q ^c -R ^2c -O-(A ^1c O)m ^c -" (However, ring Q ^c , R ^1c , R ^2c , A ^1c O, m ^c are independently synonymous with the ring Q ^a , R ^1a , R ^2a , A ^1a O, ^ma of the general formula (1), alkali metals, and alkaline earth metals (1/2 ), organic amine salt or hydrogen atom M ¹ : alkali metal, alkaline earth metal (1/2), organic amine salt or hydrogen atom) [Chemical 9] (In the formula, rings Q ^d , R ^1d , R ^2d , A ^1d O(OA ^1d ), and m ^d are independently related to the rings Q ^a , R ^1a , R ^2a , A ^1a O, and m of the general formula (1), respectively. ^a is synonymous; M ² : alkali metal, alkaline earth metal (1/2), organic amine salt or hydrogen atom) [Chemical 10] (In the formula, the rings Q ^e , R ^1e , R ^2e , A ^1e O, ^and me are independently ^synonymous with the rings Q ^a , R ^1a , R ^2a , A ^1a O, and ma of the general formula (1); M ^3. M ⁴ : independent alkali metal, alkaline earth metal (1/2), organic amine salt or hydrogen atom).

Ring Q ^c , R ^1c , R ^2c , A ^1c O, m ^c in the above general formula (3), ring Q ^d , R ^1d , R ^2d , and A ^1d O(OA ^1d ) in the above general formula (4) , m ^d , and the rings Q ^e , R ^1e , R ^2e , A ^1e O, and ^me in the above-mentioned general formula (5) are preferably each independently associated with the rings Q ^a , R ^1a , and R ^2a , A ^1a O, ma ^are the same. R ⁵ in the above general formula (3) is preferably the residue obtained by removing the terminal oxygen atom from "R ^1c -ring Q ^c -R ^2c -O-(A ^1c O)m ^c -" (however, the ring Q ^c , R ^1c , R ^2c , A ^1c O, and m ^c are each independently synonymous with the ring Q ^a , R ^1a , R ^2a , A ^1a O, and ^ma of the general formula (1)). M ¹ in the above general formula (3), M ² in the above general formula (4), and M ³ and M ⁴ in the above general formula (5) are preferably independent alkali metal or organic amine salts.

The total P core NMR integral ratio attributed to the organic phosphate P1 represented by the above general formula (3), the organic phosphate P2 represented by the above general formula (4), and the organic phosphate P3 represented by the above general formula (5) Set to 100%. At this time, the P core NMR integral ratio belonging to the organophosphate P3 represented by the general formula (5) is preferably 30 to 80%, more preferably 35 to 75%, and particularly preferably 40 to 70%.

The P core NMR integral ratio (P core NMR integral ratio (%) attributed to organophosphates P1, P2, and P3) refers to the pH of 12 or higher by adding excess KOH to alkali metal salts of organophosphates, etc. Under the conditions, the value is calculated based on the following formulas (a) to (c) using the measured value when supplied to ³¹ P-NMR (trade name: MERCURY plus NMR Spectrometor System, manufactured by VALIAN, 300MHz). In addition, a mixed solvent of heavy water/tetrahydrofuran=8/2 (volume ratio) can be used as the solvent system. In addition, in the formulas (a) to (c), "Pchem 1" represents the P core NMR integrated value belonging to the organic phosphate P1 represented by the general formula (3), and "Pchem 2" represents the general The P core NMR integral value of the organophosphate P2 represented by the formula (4), "P3" represents the P core NMR integral value of all organophosphate P3 belonging to the general formula (5).

[Number 1] P core NMR integration ratio of organophosphate P1 (%) = (P of 1) ÷ (P of 1 + P of 2 + P of 3) × 100・・・(a) [Number 2] P core NMR integration ratio of organophosphate P2 (%) = (P of 2) ÷ (P of 1 + P of 2 + P of 3) × 100・・・(b) [Number 3] P core NMR integration ratio of organophosphate P3 (%) = (P of 3) ÷ (P of 1 + P of 2 + P of 3) × 100・・・(c) The method for producing the organic phosphate represented by the general formulas (3) to (5) of the present invention is not particularly limited. For example, cycloalkyl alkanols, or cycloalkyl alkanols are randomly, block- or These mixing methods include addition polymerization of alkylene oxides with 2 to 4 carbon atoms, mixing and esterification with a phosphorylating agent represented by anhydrous phosphoric acid, or further neutralizing it with an alkali. maker.

<Other ionic surfactants> The treatment agent for synthetic fibers of the present invention may further contain other ionic surfactants. Examples thereof include known anionic surfactants and cationic surfactants used as fiber treatment agents. Active agents, amphoteric surfactants, etc. Specific examples of the anionic surfactant system include: (1) carboxylic acid soap type ionic surfactants such as potassium acetate, potassium octanoate, potassium oleate, sodium oleate, and potassium alkenyl succinate. (2) Secondary alkane sulfonate sodium salt, dodecyl benzene sulfonate sodium salt, dioctyl sulfosuccinate sodium salt and other sulfonate type ionic surfactants; (3) Polyoxyethylene lauryl Sulfate ester type ionic surfactants such as sulfate ester sodium salt, cetyl sulfate potassium salt, tallow vulcanized oil, castor oil vulcanized oil and other sulfate ester ionic surfactants; (4) Lauryl phosphate sodium salt, oleyl phosphate potassium salt, phosphoric acid ten Organic phosphate ester salts such as hexadecyl ester potassium salt, stearyl phosphate potassium salt, oleyl phosphate triethanolamine salt, polyoxyethylene oil ether phosphate ester and polyoxyethylene laurylamine ether salt, etc. Examples of the cationic surfactant include quaternary ammonium salts such as tetrabutylammonium salt, and examples of the amphoteric surfactant include organic amine oxides such as dimethylstearyl amine oxide; dimethylammonium acetic acid beets Type amphoteric surfactants; N,N-bis(2-carboxyethyl)-octylamine sodium and other alanine-type amphoteric surfactants, etc. These components may be used individually by 1 type, or in combination of 2 or more types.

The treatment agent for synthetic fibers of the present invention contains the cycloalkyl alkanol derivative represented by the above general formula (1) and the above general formula (2), and other nonionic surfactants and ionic interfaces. In the case of active agents, relative to the total mass of the synthetic fiber treatment agent, the nonionic surfactant content is preferably 50 to 99 mass %, more preferably 60 to 99 mass %, and particularly preferably 65 mass %. ~99 mass%, and the other ionic surfactants preferably contain 0.01 to 10 mass%, more preferably 0.1 to 10 mass%, and particularly preferably 0.5 to 5 mass%. When the ionic surfactant is selected from the organic phosphate P1 represented by the above general formula (3), the organic phosphate P2 represented by the above general formula (4), and the organic phosphate P3 represented by the above general formula (5), When at least one kind of organic phosphate is selected, the total amount of the organic phosphate represented by the above general formulas (3) to (5) is preferably 0.01 to 10 mass%, more preferably, relative to the total mass of the synthetic fiber treatment agent. The system contains 0.05~5 mass%, and the special series contains 0.1~3 mass%.

The treatment agent for synthetic fibers of the present invention contains the cycloalkyl alkanol derivative represented by the above general formula (1) and the above general formula (2), and a nonionic interface other than the above cycloalkyl alkanol derivative. When activating agents, smoothing agents, and ionic surfactants are used, the nonionic surfactant in addition preferably contains 5 to 60 mass %, more preferably 10 to 60 mass %, and particularly preferably 10 to 60 mass %. 50% by mass; the other smoothing agents preferably contain 30 to 80% by mass, more preferably 30 to 70% by mass, and particularly preferably 40 to 70% by mass; other ionic surfactants The preferred system contains 0.1 to 25 mass%, the more preferred system contains 0.5 to 20 mass%, and the particularly preferred system contains 1.0 to 15 mass%. When the ionic surfactant is selected from the organic phosphate P1 represented by the above general formula (3), the organic phosphate P2 represented by the above general formula (4), and the organic phosphate P3 represented by the above general formula (5), When at least one kind of organic phosphate is selected from, the total amount of the organic phosphate represented by the above general formulas (3) to (5) is preferably 0.01 to 10% by mass relative to the total mass of the synthetic fiber treatment agent. The more optimal system contains 0.05 to 5 mass %, and the particularly optimal system contains 0.1 to 3 mass %. The synthetic fiber treatment agent of this composition is suitable as a synthetic fiber treatment agent in the spinning-drawing step.

＜Other ingredients＞ The treatment agent for synthetic fibers of the present invention may be further blended with stabilizers, antistatic agents, defoaming agents (polysilicone compounds, minerals) for maintaining the quality of the treatment agent within the range that does not hinder the effects of the present invention. Oil, etc.), adhesives, antioxidants, UV absorbers and other ingredients commonly used in synthetic fiber treatment agents.

＜Synthetic fiber＞ The synthetic fiber of the present invention is a synthetic fiber to which the treatment agent for synthetic fiber of the present invention is adhered. The synthetic fibers to which the treatment agent for synthetic fibers of the present invention is adhered are not particularly limited, and examples thereof include: (1) polyesters such as polyethylene terephthalate, polytrimethylene terephthalate, and polylactate. (2) Polyamide-based fibers such as nylon 6 and nylon 66; (3) Polyacrylic-based fibers such as polyacrylic acid and modified polyacrylonitrile; (4) Polyolefin-based fibers such as polyethylene and polypropylene; and Polyurethane fiber, etc. Among them, the effect is higher when attached to polyester fibers and polyamide fibers. There is no particular restriction on the proportion of the treatment agent for synthetic fibers of the present invention that adheres to the synthetic fibers. The treatment agent for synthetic fibers of the present invention is preferably adhered in a proportion of 0.1 to 3% by mass relative to the synthetic fibers, and more preferably is The proportion of 0.3~1.2% by mass is attached. With this structure, the effect of the present invention can be further enhanced. In addition, the step of adhering the treatment agent for the synthetic fiber of the present invention is not particularly limited, and examples include a spinning step, a step of simultaneously spinning and drawing, and the like. Examples of methods for adhering the treatment agent of the present invention to synthetic fibers include a roller oil supply method, a diversion oil supply method using a metering pump, a dipping oil supply method, and a spray oil supply method. Examples of the form when the treatment agent of the present invention is adhered to synthetic fibers include a single agent, an organic solvent solution, an aqueous liquid, and the like, and an aqueous liquid is preferred. When the aqueous liquid of the treatment agent of the present invention is adhered, the treatment agent of the present invention may be preferably adhered to 0.1 to 3% by mass, and more preferably 0.3 to 1.2% by mass relative to the synthetic fibers.

The treatment agent for synthetic fibers of the present invention contains the cycloalkyl alkanol derivative represented by the above general formula (1) and the above general formula (2) as an essential component, and is used in the spinning step, false twisting step, and As well as in post-processing steps, it can cope with the high speed in recent years and can prevent static electricity and pilling. Furthermore, since the treatment agent for synthetic fibers of the present invention has excellent emulsion stability, the components contained therein do not separate even if it is stored for a long time. Furthermore, because it has excellent low-temperature operability in an environment below freezing point, synthetic fiber treatment agents do not occur. Since there are no problems such as coagulation of the ingredients of the treatment agent, the treatment agent for synthetic fibers can be evenly adhered and fully functional, and it does not take time to fill when preparing the emulsion. [Example]

The present invention will be described below with reference to examples, but the technical scope of the present invention is not limited to these. In addition, in the following examples and comparative examples, "part" means "mass part", and "%" means "mass %".

<Synthesis of cycloalkyl alkanol derivatives> (A-1) Fill a reaction vessel with: 184g of 6-cyclohexylhexanol and 282g of oleic acid, melt them at 75°C under nitrogen, and add a catalyst. 0.6 g of p-toluenesulfonic acid was reacted at 120° C. and 2 mmHg reduced pressure for 4 hours while draining the generated water out of the reaction system. Then, in the presence of nitrogen, the pressure was returned to normal pressure at 105°C, an adsorbent was added to treat the catalyst, and filtration was performed at 90°C to obtain A-1. This "A-1" is a cycloalkyl alkane in which ring ^{Q a} in the general formula (1) is a cyclohexylene group, R ^1a is a hydrogen atom, R ^2a is a hexylene group, R ³ is an oleyl group, and m ^a is 0 alcohol compounds. In addition, the purity of "A-1" was measured using gas chromatography-mass spectrometry (hereinafter referred to as "GC-MS") based on the cycloalkyl alkanol derivative of the present invention and was confirmed to be 99%.

(A-2) In the above-described production method of "A-1", except that 198 g of 7-cyclohexylhexanol was used instead of 6-cyclohexylhexanol, A-2 was obtained in the same manner. This "A-2" is a cycloalkyl group in which ring ^{Q a} in the general formula (1) is a cyclohexylene group, R ^1a is a hydrogen atom, R ^2a is a heptylene group, R ³ is an oleyl group, and ma ^is 0 Alkanol compounds. In addition, the purity of "A-2" was confirmed to be 98% based on the cycloalkyl alkanol derivative of the present invention by GC-MS measurement.

(A-3) 198 g of 7-cyclohexylheptanol was loaded into a hot pressure cooker, and after adding 0.3 g of potassium hydroxide as a catalyst, the inside of the hot pressure cooker was fully replaced with nitrogen. While stirring, maintain the gauge pressure at 0.0~0.4MPa and the reaction temperature at 110~120°C, press in 132g of ethylene oxide, and perform addition polymerization for about 5 hours. Then, the obtained reactant was moved into a flask, and the potassium hydroxide of the catalyst was neutralized with phosphoric acid. The potassium phosphate produced by neutralization is filtered to obtain an ethylene oxide addition polymer of 7-cyclohexylheptanol. After melting 165g of the obtained addition polymer and 141g of oleic acid at 75°C in the presence of nitrogen, 0.3g of p-toluenesulfonic acid as a catalyst was added, and the resulting of water was discharged from the reaction system while the reaction was carried out for 4 hours. Next, in the presence of nitrogen, the pressure was returned to normal pressure at 105°C, an adsorbent was added to treat the catalyst, and filtration was performed at 90°C to obtain A-3. This "A-3" is a general formula (1) in which ring Q ^a is a cyclohexylene group, R ^1a is a hydrogen atom, R ^2a is a heptylene group, R ³ is an oleyl group, and A ^1a O is EO (ethylene group). Oxygen group), a cycloalkyl alkanol derivative compound with m ^a of 3. In addition, the purity of "A-3" was confirmed to be 97% based on the cycloalkyl alkanol derivative of the present invention by GC-MS measurement.

(A-4) In the above production method of "A-3", in addition to replacing 7-cyclohexylheptanol, 184g of 6-cyclohexylhexanol is used, and 132g of ethylene oxide is replaced by epoxy. A-4 was obtained in the same manner except that 264 g of ethane, 116 g of propylene oxide, and 82 g of octanoic acid were used instead of 141 g of oleic acid. In the general formula (1), ring Q ^a of "A-4" is a cyclohexylene group, R ^1a is a hydrogen atom, R ^2a is a hexylene group, R ³ is an octyl group, and A ^1a O is EO (ethylene group). A cycloalkyl alkanol derivative compound with 6 moles, PO (propyleneoxy) 2 moles, and m ^a of 8. In addition, the purity of "A-4" was confirmed to be 95% based on the cycloalkyl alkanol derivative of the present invention by GC-MS measurement.

(A-5) 184 g of 6-cyclohexylhexanol was loaded into a hot pressure cooker, and after adding 0.3 g of potassium hydroxide as a catalyst, the inside of the hot pressure cooker was fully replaced with nitrogen. While stirring, 88 g of ethylene oxide and 116 g of propylene oxide were pressed in while maintaining a gauge pressure of 0.0 to 0.4 MPa and a reaction temperature of 110 to 120°C, and the addition polymerization reaction was performed for about 5 hours. Then, the obtained reactant was moved into a flask, and the potassium hydroxide of the catalyst was neutralized with phosphoric acid. The potassium phosphate produced by neutralization is filtered to obtain an addition polymer of ethylene oxide and propylene oxide of 7-cyclohexylheptanol. After melting 194g of the obtained addition polymer and 37g of adipic acid at 75°C in the presence of nitrogen, 0.3g of p-toluenesulfonic acid as a catalyst was added, and the resulting mixture was melted at 120°C and 2mmHg under reduced pressure. The generated water was discharged from the reaction system while the reaction was carried out for 4 hours. Then, in the presence of nitrogen, the pressure was returned to normal pressure at 105°C, an adsorbent was added to treat the catalyst, and filtration was performed at 90°C to obtain A-5. This "A-5" is a general formula (2) in which ring Q ^b is a cyclohexylene group, R ^1b is a hydrogen atom, R ^2b is a hexylene group, R ⁴ is an hexylene diyl group, and A ^1b O is EO (ethylidene group). It is a cycloalkyl alkanol derivative compound with 2 moles of PO (oxyl group), 2 moles of PO (propyleneoxy group), and m ^b of 4. In addition, the purity of "A-5" was confirmed to be 96% based on the cycloalkyl alkanol derivative of the present invention by GC-MS measurement.

(A-6) In the above production method of "A-3", 128g of 2-cyclohexylethanol is used instead of 7-cyclohexylheptanol, and 142g of stearic acid is used instead of 141g of oleic acid. Except for this, proceed in the same manner and obtain A-6. The "A-6" ring Q ^a in the general formula (1) is a cyclohexylene group, R ^1a is a hydrogen atom, R ^2a is an ethylene group, R ³ is a stearyl group, and A ^1a O is an EO (etylene group). ethoxy), a cycloalkyl alkanol derivative compound with m ^a of 3. In addition, the purity of "A-6" was confirmed to be 97% based on the cycloalkyl alkanol derivative of the present invention by GC-MS measurement.

(A-7) 128 g of 2-cyclohexylethanol was loaded into a hot pressure cooker, and after adding 0.3 g of potassium hydroxide as a catalyst, the hot pressure cooker was fully replaced with nitrogen. While stirring, 352g of ethylene oxide and 116g of propylene oxide were pressed in while maintaining a gauge pressure of 0.0~0.4MPa and a reaction temperature of 110~120°C, and the addition polymerization reaction was performed for about 5 hours. Then, the obtained reactant was moved into a flask, and the potassium hydroxide of the catalyst was neutralized with phosphoric acid. The potassium phosphate produced by neutralization was filtered to obtain the addition polymer A-7 of ethylene oxide and propylene oxide of 2-cyclohexylethanol. The "A-7" ring Q ^a in the general formula (1) is a cyclohexylene group, R ^1a is a hydrogen atom, R ^2a is an ethylene group, R ³ is a hydrogen atom, and A ^1a O is EO (ethylene oxide). It is a cycloalkyl alkanol derivative compound with 8 moles of PO (propyloxy) group and 2 moles of m ^a . In addition, the purity of "A-7" was confirmed to be 100% based on the cycloalkyl alkanol derivative of the present invention by GC-MS measurement.

(A-8) In the above production method of "A-7", 198g of 7-cyclohexylheptanol is used instead of 2-cyclohexylethanol, and 352g of ethylene oxide and 116g of propylene oxide are used instead. A-8 was obtained in the same manner except that 264 g of ethylene oxide and 116 g of propylene oxide were used. This "A-8" is a general formula (1) in which ring Q ^a is a cyclohexylene group, R ^1a is a hydrogen atom, R ^2a is a heptylene group, R ³ is a hydrogen atom, and A ^1a O is EO (ethylene oxide). It is a cycloalkyl alkanol derivative compound with 6 moles of base), 2 moles of PO (propyleneoxy), and m ^a of 8. In addition, the purity of "A-8" was confirmed to be 100% based on the cycloalkyl alkanol derivative of the present invention by GC-MS measurement.

(A-9) In the above production method of "A-7", 184g of 6-cyclohexylhexanol is used instead of 2-cyclohexylethanol, and 638g of propylene oxide is used instead of 116g of propylene oxide. Except for this, proceed in the same manner and obtain A-9. This "A-9" is a general formula (1) in which ring Q ^a is a cyclohexylene group, R ^1a is a hydrogen atom, R ^2a is a hexylene group, R ³ is a hydrogen atom, and A ^1a O is an EO (ethyleneoxy group). ) is a cycloalkyl alkanol derivative compound with 8 moles, PO (propyleneoxy) 11 moles, and m ^a of 19. In addition, the purity of "A-9" was confirmed to be 100% based on the cycloalkyl alkanol derivative of the present invention by GC-MS measurement.

(A-10) In the above production method of "A-7", 184g of 6-cyclohexylhexanol is used instead of 2-cyclohexylethanol, and 352g of ethylene oxide and 116g of propylene oxide are used. A-10 was obtained in the same manner except that 348 g of propylene oxide was used. This "A-10" is a general formula (1) in which ring Q ^a is a cyclohexylene group, R ^1a is a hydrogen atom, R ^2a is a hexylene group, R ³ is a hydrogen atom, and A ^1a O is PO (propyleneoxy group). ) A cycloalkyl alkanol derivative compound with 6 moles and m ^a of 6. In addition, the purity of "A-10" was confirmed to be 100% based on the cycloalkyl alkanol derivative of the present invention by GC-MS measurement.

(A-11) In the above production method of "A-7", 282g of 8-(2-octylcyclopropyl)octanol was used instead of 2-cyclohexylethanol, and 352g of ethylene oxide was substituted. , 116g of propylene oxide, and A-11 was obtained in the same manner except that 132g of ethylene oxide and 174g of propylene oxide were used instead. This "A-11" is a general formula (1) in which ring Q ^a is 1,2-cyclopropyl group, R ^1a is octyl group, R ^2a is octyl group, R ³ is a hydrogen atom, and A ^1a O is A cycloalkyl alkanol derivative compound with 3 moles of EO (ethyleneoxy), 3 moles of PO (propyleneoxy), and m ^a of 6. In addition, the purity of "A-11" was confirmed to be 100% based on the cycloalkyl alkanol derivative of the present invention by GC-MS measurement.

(A-12) In the above-mentioned production method of "A-7", 72g of cyclopropylmethanol is used instead of 2-cyclohexylethanol, and 352g of ethylene oxide and 116g of propylene oxide are used instead. Except for 440 g of ethylene oxide, the same procedure was carried out to obtain A-12. This "A-12" is a general formula (1) in which ring Q ^a is a cyclopropylene group, R ^1a is a hydrogen atom, R ^2a is a methylene group, R ³ is a hydrogen atom, and A ^1a O is EO (ethylene ethylene). Oxygen group) A cycloalkyl alkanol derivative compound with 10 moles and m ^a of 10. In addition, the purity of "A-12" was confirmed to be 100% based on the cycloalkyl alkanol derivative of the present invention by GC-MS measurement.

＜Synthesis of Organophosphate＞ (B-1) 184g of 6-cyclohexylhexanol was loaded into the hot pressure cooker, and after adding 0.3g of potassium hydroxide as catalyst, the hot pressure cooker was fully replaced with nitrogen. While stirring, 220 g of ethylene oxide was pressed in while maintaining a gauge pressure of 0.0 to 0.4 MPa and a reaction temperature of 110 to 120°C, and the addition polymerization reaction was performed for about 5 hours. Then, the obtained reactant was moved into a flask, and the potassium hydroxide of the catalyst was neutralized with phosphoric acid. The potassium phosphate produced by neutralization is filtered to obtain an ethylene oxide addition polymer of 6-cyclohexylhexanol. 202g of the obtained polymer was filled into a flask, kept at 65~70°C, and 24g of anhydrous phosphoric acid was added in small amounts over 1 hour while stirring, and a maturation reaction was carried out at 65~70°C for 3 hours. After cooling to room temperature, 28 g of potassium hydroxide was slowly added for neutralization to obtain organic phosphate B-1. This "B-1" is P that will belong to the organic phosphate P1 represented by the general formula (3) of this case, the organic phosphate P2 represented by the general formula (4) of this case, and the organic phosphate P3 represented by the general formula (5) of this case When the total core NMR integral ratio is set to 100%, the P core NMR integral ratios of P1 to P3 are 0%, 48%, and 52% respectively.

(B-2) Put 128g of 2-cyclohexylethanol into the hot pressure cooker, add 0.3g of potassium hydroxide as catalyst, and fully replace the hot pressure cooker with nitrogen. While stirring, 174 g of propylene oxide was pressed in while maintaining a gauge pressure of 0.0 to 0.4 MPa and a reaction temperature of 110 to 120°C, and the addition polymerization reaction was performed for about 5 hours. Then, the obtained reactant was moved into a flask, and the potassium hydroxide of the catalyst was neutralized with phosphoric acid. The potassium phosphate produced by neutralization is filtered to obtain a propylene oxide addition polymer of 2-cyclohexylethanol. 151g of the obtained polymer was filled into a flask, kept at 65~70°C, and 22g of anhydrous phosphoric acid was added in small amounts over 1 hour while stirring, and a maturation reaction was carried out at 65~70°C for 3 hours. After cooling to room temperature, 87 g of dibutylethanolamine was slowly added to neutralize, and organic phosphate B-2 was obtained. This "B-2" is P that will belong to the organic phosphate P1 represented by the general formula (3) of this case, the organic phosphate P2 represented by the general formula (4) of this case, and the organic phosphate P3 represented by the general formula (5) of this case When the total core NMR integral ratio is set to 100%, the P core NMR integral ratios of P1 to P3 are 12%, 43%, and 45% respectively.

(B-3) 198g of 7-cyclohexylheptanol was loaded into the hot pressure cooker, and after adding 0.3g of potassium hydroxide as catalyst, the hot pressure cooker was fully replaced with nitrogen. While stirring, 264 g of ethylene oxide and 116 g of propylene oxide were pressed in while maintaining a gauge pressure of 0.0 to 0.4 MPa and a reaction temperature of 110 to 120°C, and the addition polymerization reaction was performed for about 5 hours. Then, the obtained reactant was moved into a flask, and the potassium hydroxide of the catalyst was neutralized with phosphoric acid. The potassium phosphate produced by neutralization is filtered to obtain an addition polymer of ethylene oxide and propylene oxide of 7-cyclohexylheptanol. 289g of the obtained polymer was filled into a flask, kept at 65~70°C, and 23g of anhydrous phosphoric acid was added in small amounts over 1 hour while stirring, and a maturation reaction was carried out at 65~70°C for 3 hours. After cooling to room temperature, 28 g of potassium hydroxide was slowly added to neutralize, and organic phosphate B-3 was obtained. This "B-3" is P that will belong to the organic phosphate P1 represented by the general formula (3) of this case, the organic phosphate P2 represented by the general formula (4) of this case, and the organic phosphate P3 represented by the general formula (5) of this case When the total nuclear NMR integral ratio is set to 100%, the P core NMR integral ratios of P1 to P3 are 5%, 47%, and 48% respectively.

(B-4) Put 184g of 6-cyclohexylhexanol into a flask and keep it at 65~70°C. Add 45g of anhydrous phosphoric acid in small amounts over 1 hour while stirring, and then perform a 3-hour maturation reaction at 65~70°C. After cooling to room temperature, 40 g of potassium hydroxide was slowly added to neutralize, and organic phosphate B-4 was obtained. This "B-4" is P that will belong to the organic phosphate P1 represented by the general formula (3) of this case, the organic phosphate P2 represented by the general formula (4) of this case, and the organic phosphate P3 represented by the general formula (5) of this case When the total core NMR integral ratio is set to 100%, the P core NMR integral ratios of P1 to P3 are 16%, 42%, and 42% respectively.

The compositions of the treatment agents for synthetic fibers of the present invention (Examples 1 to 16) are shown in Table 1, and the compositions of the comparative examples (Comparative Examples 1 to 4) are shown in Table 2.

[Table 1] distinguish Cycloalkyl alkanol derivatives ionic surfactant nonionic surfactant Smoothing agent Organophosphate Other ionic surfactants Kind Ratio(mass%) Kind Ratio(mass%) Kind Ratio(mass%) Kind Ratio(mass%) Kind Ratio(mass%) Example 1 A-1 4 E-1 5 N-1 10 L-2 30 A-2 2 B-1 1 E-2 2 N-3 8 L-3 20 A-9 4 E-3 2 N-5 4 L-6 8 2 E-1 5 N-1 15 L-1 30 A-3 1.5 B-3 0.5 E-2 2 N-3 10 L-3 20 E-3 3 N-4 5 L-6 8 3 A-2 4 E-1 4 N-1 10 L-1 20 A-4 2 B-1 1 E-2 4 N-4 6 L-3 26 N-5 8 L-4 15 4 N-1 14 L-2 10 A-5 0.3 B-2 0.5 E-1 5.5 N-2 10 L-3 40 N-4 14.7 L-5 5 5 A-6 5 E-1 1 N-4 14 A-7 4 B-1 0.5 E-4 0.5 N-5 20 - - N-6 55 6 A-6 5 N-1 15 L-2 17 A-10 3 B-4 0.5 E-1 5.5 N-3 10 L-3 35 N-4 4 L-4 5 7 A-1 6 E-2 1 N-3 12 L-2 16 A-2 3 B-1 1 E-4 4 N-8 12 L-4 30 N-10 5 L-7 10 8 A-1 5 E-1 2 N-1 12 L-1 20 A-10 3 B-3 1 E-3 2 N-5 10 L-3 30 N-8 7 L-7 8 9 A-6 5 N-4 14 A-8 4 B-2 0.5 E-3 1.5 N-7 40 - - N-9 35 10 A-1 2 E-2 2 N-2 15 L-4 15 A-5 2 B-4 0.5 E-3 3.5 N-9 10 L-5 35 N-10 4 L-7 11 11 A-5 8 N-1 15 L-2 13 A-10 0.5 - - E-1 5.5 N-3 10 L-3 40 N-4 8 12 A-1 5 E-1 2 N-1 12 L-1 20 A-10 3 - - E-3 3 N-5 10 L-3 30 N-8 7 L-7 8 13 E-1 2 N-1 5 L-2 20 A-8 15 B-4 0.5 E-3 4 N-2 8 L-4 40 N-5 5.5 14 E-1 1 N-5 10 L-2 63 A-10 5 - - E-4 1 N-6 10 N-7 10 E-4 7 N-1 7 L-2 20 15 A-11 8 - - E-2 3 N-3 8 L-4 35 N-5 12 E-4 7 N-2 7 L-3 10 16 A-12 0.2 - - E-2 3 N-3 10.8 L-4 55 N-10 7

[Table 2] distinguish Cycloalkyl alkanol derivatives ionic surfactant nonionic surfactant Smoothing agent Organophosphate Other ionic surfactants Kind Ratio(mass%) Kind Ratio(mass%) Kind Ratio(mass%) Kind Ratio(mass%) Kind Ratio(mass%) Comparative example N-1 16 L-1 10 1 - - - - E-1 1 N-2 8 L-2 30 N-3 15 L-3 20 E-2 2 N-1 16 L-4 40 2 - - - - E-4 2 N-2 10 L-5 10 N-4 10 L ^- 6 10 E-2 1 N-3 12 L-2 20 3 - - B-1 1 E-4 4 N-8 12 L-4 35 N-10 5 L-7 10 N-1 15 L-2 30 4 - - - - - - N-2 10 L-3 10 N-3 15 L-4 20

The codes in Tables 1 and 2 are as follows: E-1: Secondary alkyl (carbon number 12~15) sodium sulfonate E-2: Potassium oleate E-3: Between oleyl alcohol EO2 phosphate and laurylamine EO2 Salt E-4: Potassium Laureth Phosphate N-1: Hardened castor oil EO12 trioleate N-2: Tridecanol EO3・PO2 palmitate N-3: Oleic acid EO5 N-4 : Nonanol EO6・PO2 N-5: Lauryl alcohol EO6・PO2 N-6: Isotridecanol EO10・PO15 N-7: Lauryl alcohol EO55・PO40 N-8: Tetradecyl alcohol EO15・PO15 N-9: Butyl alcohol Alcohol EO6・PO10 N-10: Glycerin EO12 L-1: Mineral oil (47mm ² /s) L-2: Octyl palmitate (palmitate) L-3: Lauryl oleate L-4: Isotridecyl stearate Alkyl ester L-5: Trimethylolpropane trilaurate (laurate) L-6: Sorbitan monooleate L-7: Rapeseed oil

・Evaluation of emulsion stability Mix the synthetic fiber treatment agent and ion-exchange water evenly to prepare a synthetic fiber treatment agent emulsion with a concentration of 15%. Put it into a polyethylene bottle with a lid and seal it. The synthetic fiber treatment agent emulsion is allowed to stand at 40°C. After leaving it for 7 days, the appearance was visually observed, and the change in penetration rate was evaluated based on the following criteria. The transmittance was measured using a spectrophotometer (UV-visible spectrophotometer U-1800 manufactured by Shimadzu Corporation), and evaluated based on the following standards. The results are summarized in Table 3. [Evaluation criteria for emulsion stability] ◎◎: The penetration rate of the lotion immediately after preparation is reduced by less than 5%. ◎: The penetration rate of the lotion immediately after preparation is reduced by more than 5% and less than 10% ○: The penetration rate of the lotion immediately after preparation is reduced by more than 10% and less than 20% ×: The penetration rate of the emulsion immediately after preparation is reduced by more than 20%, or the generation or separation of particles is confirmed.

・Evaluation of low-temperature operability Heat to 30°C, put 60 mL of the homogenized synthetic fiber treatment agent into a 100 mL capped polyethylene bottle (inner diameter 45 mm), and then seal the container. The polyethylene bottle filled with the synthetic fiber treatment agent was left to stand in an incubator with a set temperature of -5°C for 3 days. After leaving to stand, the appearance of the aqueous liquid was visually judged and evaluated based on the following criteria. "Fluidity" shown in the following criteria means that when a polyethylene bottle filled with a synthetic fiber treatment agent is tilted sideways (90°) and part of the aqueous liquid flows out of the container within 30 seconds, it is judged to be "fluidity". Liquid. The results are summarized in Table 3. [Criteria for evaluation of low-temperature operability] ◎◎: No fogging or turbidity in appearance, and fluidity ◎: Although fluid, the appearance appears foggy, turbid, and partially solidified. ○: Although it is fluid, the appearance is foggy and turbid, and most of it is solidified. ×: Completely solidified, no fluidity

・Manufacturing of extended yarn Polyethylene terephthalate with an intrinsic viscosity of 0.64 and a titanium oxide content of 0.2% is dried using a conventional method and then spun using an extruder at 295°C. The traveling yarns are ejected from the spinneret and cooled and solidified. On the line, an aqueous liquid of a treatment agent for synthetic fibers prepared with a concentration of 10% is applied using a diversion oil supply method using a metering pump so that the adhesion amount of the treatment agent for synthetic fibers becomes 1.0%. After the yarn guide is used to bundle the yarn, the first godet roller with a surface speed of 1400m/min and a surface temperature of 90°C and the second godet roller with a surface speed of 4800m/min and a surface temperature of 150°C are stretched. Wind up at high speed to obtain 36-count extension yarn of 83 denier.

・Evaluation of static electricity generation The drawn yarn produced by the above-mentioned drawn yarn production was rewinded to obtain a package yarn with a yarn amount of 200 g. The package yarn was subjected to humidity control at 20° C. and a relative humidity of 40% for 3 days, and then the static electricity generation was measured and evaluated under the following conditions. (condition) In an environment of 20℃ and relative humidity of 40%, set 20 cones of yarn on the creel for unwinding. After passing through the washer tensioner, adjust the entry and exit angles of the yarn to 10 degrees and a diameter of 2cm. , three alumina pins with a length of 5cm are moved and coiled at a speed of 200m/min. At this time, the static electricity (static electricity generation) of the sheet composed of 20 wandering strands was measured using a collector-type potentiometer at a position 20 cm away from the third alumina pin outlet. The measured values were evaluated based on the following criteria. The results are summarized in Table 3. [Evaluation criteria for static electricity generation] ◎: Static electricity generation is less than 0.5kV, excellent antistatic properties ○: Static electricity generation is 0.5kV or more and less than 2kV, good antistatic property ×: Static electricity generation reaches 2kV or more, and the antistatic property is poor

[table 3] distinguish Lotion stability Low temperature operability Static electricity generation Example 1 ◎◎ ◎◎ ◎ Example 2 ◎◎ ◎◎ ◎ Example 3 ◎◎ ◎◎ ◎ Example 4 ◎◎ ◎◎ ◎ Example 5 ◎◎ ◎◎ ◎ Example 6 ◎◎ ◎◎ ◎ Example 7 ◎◎ ◎◎ ◎ Example 8 ◎◎ ◎◎ ◎ Example 9 ◎◎ ◎◎ ◎ Example 10 ◎◎ ◎◎ ◎ Example 11 ◎◎ ◎◎ 〇 Example 12 ◎◎ ◎◎ 〇 Example 13 ◎ ◎ ◎ Example 14 ◎ ◎ 〇 Example 15 ◎ 〇 〇 Example 16 〇 〇 〇 Comparative example 1 × × 〇 Comparative example 2 × × 〇 Comparative example 3 × × 〇 Comparative example 4 × × ×

From the results in Table 3, it can be seen that the synthetic fiber treatment agents of Examples 1 to 16 of the specific examples of the present invention are excellent in emulsion stability and low-temperature operability, and are also excellent in antistatic properties of drawn yarns. (industrial availability)

The processing agent for synthetic fibers of the present invention, the synthetic fibers to which the processing agent for synthetic fibers is adhered, and the processing method of synthetic fibers can respond to recent trends in the spinning step, false twisting step, and post-processing step of synthetic fibers. The speed is increased and the excellent antistatic properties are used to prevent static electricity and pilling. Furthermore, the treatment agent for synthetic fibers of the present invention has excellent emulsion stability and low-temperature operability in an environment below freezing point. Therefore, even if it is stored in a low-temperature environment, the components contained therein do not separate, which contributes to the use of synthetic fibers. The treatment adheres evenly.

Claims (9)

A treatment agent for synthetic fibers containing at least one selected from the cycloalkyl alkanol derivatives represented by the following general formula (1) and general formula (2);

(In the formula, ring Q ^a : cycloalkylene group with 3 to 8 carbon atoms R ^1b : hydrogen atom or alkyl group with 1 to 12 carbon atoms R ^2a : divalent hydrocarbon group with 1 to 12 carbon atoms R ³ : hydrogen atom, Or the residue A ^1a O after removing the hydroxyl group from a monocarboxylic acid having 6 to 22 carbon atoms: an alkyleneoxy group having 2 to 4 carbon atoms (however, when there are two or more alkyleneoxy groups, they may be used alone 1 or 2 or more types) m ^a : an integer from 0 to 100; except when m ^a is 0 and R ³ is a hydrogen atom)

(In the formula, the rings Q ^b , R ^1b , R ^2b , A ^1b O, and m ^b are independently synonymous with the rings Q ^a , R ^1a , R ^2a , A ^1a O, and m ^a of the formula (1); R ⁴ : The residue obtained by removing two hydroxyl groups from a dicarboxylic acid having 4 to 12 carbon atoms; except for the case where m ^b is 0); the above-mentioned treatment agent for synthetic fibers further contains a nonionic surfactant (but, the above (except cycloalkyl alkanol derivatives) and ionic surfactants. The treatment agent for synthetic fibers according to Claim 1, which contains a cycloalkyl alkanol derivative in which R ^1a of the above general formula (1) is a hydrogen atom and a ring in which R ^1b of the above general formula (2) is a hydrogen atom. One or more types selected from alkyl alkanol derivatives. The treatment agent for synthetic fibers according to claim 1 or 2, which contains a cycloalkyl alkanol derivative in which R ^2a of the above general formula (1) is a divalent hydrocarbon group having 2 to 8 carbon atoms and the above general formula (2 ), R ^2b is at least one selected from the group consisting of cycloalkyl alkanol derivatives with a divalent hydrocarbon group having 2 to 8 carbon atoms. The treatment agent for synthetic fibers according to Claim 1, which contains a cycloalkyl alkanol in which R ³ in the general formula (1) is a residue obtained by removing a hydroxyl group from an aliphatic monocarboxylic acid having 6 to 22 carbon atoms. At least one selected from the group consisting of derivatives and cycloalkyl alkanol derivatives represented by the general formula (2) above. The treatment agent for synthetic fibers according to claim 1, wherein the cycloalkyl alkanol derivative contains 0.01 to 30 mass % relative to the total mass of the treatment agent for synthetic fibers. The treatment agent for synthetic fibers according to claim 1, further containing a smoothing agent. The treatment agent for synthetic fibers according to claim 1, wherein the ionic surfactant contains an organic phosphate P1 represented by the following general formula (3), an organic phosphate P2 represented by the following general formula (4), and At least one organic phosphate selected from the organic phosphate P3 represented by the following general formula (5); [Chemical 3]

(In the formula, the rings Q ^c , R ^1c , R ^2c , A ^1c O, and m ^c are independently synonymous with the rings Q ^a , R ^1a , R ^2a , A ^1a O, and ma of the general formula (1); ⁿ : Integer R ⁵ from 2 to 4: The residue after removing the terminal oxygen atom from "R ^1c -ring Q ^c -R ^2c -O-(A ^1c O)m ^c -" (However, ring Q ^c , R ^1c , R ^2c , A ^1c O, m ^c are independently synonymous with the ring Q ^a , R ^1a , R ^2a , A ^1a O, ^ma of the general formula (1), alkali metals, and alkaline earth metals (1/2 ), organic amine salt or hydrogen atom M ¹ : alkali metal, alkaline earth metal (1/2), organic amine salt or hydrogen atom)

(In the formula, rings Q ^d , R ^1d , R ^2d , A ^1d O(OA ^1d ), and m ^d are independently related to the rings Q ^a , R ^1a , R ^2a , A ^1a O, and m of the general formula (1), respectively. ^a is synonymous; M ² : alkali metal, alkaline earth metal (1/2), organic amine salt or hydrogen atom)

(In the formula, the rings Q ^e , R ^1e , R ^2e , A ^1e O, and ^me are independently ^synonymous with the rings Q ^a , R ^1a , R ^2a , A ^1a O, and ma of the general formula (1); M ³ , M ⁴ : each independently an alkali metal, an alkaline earth metal (1/2), an organic amine salt or a hydrogen atom). A synthetic fiber to which the treatment agent for synthetic fibers according to any one of claims 1 to 7 is attached. A method for treating synthetic fibers, in which the treating agent for synthetic fibers according to any one of claims 1 to 7 is adhered to the synthetic fibers in an amount of 0.1 to 5% by mass.