Treatment agents for synthetic fibers, synthetic fiber and methods for treating a synthetic fiber

Abstract

Treatment agent for synthetic fibers, which has: one or more selected cycloalkylalkanol derivatives, represented by the following formulas (1) and (2): where the ring Q a a cycloalkylene group with 3 to 8 carbon atoms, R 1a a hydrogen atom or an alkyl group with 1 to 12 carbon atoms, R 2a a divalent hydrocarbon group with 1 to 12 carbon atoms, R 3 a hydrogen atom or a residue obtained by removing a hydroxyl group from a monocarboxylic acid with 6 to 22 carbon atoms, A 1a O is an alkylenoxy group with 2 to 4 carbon atoms, where only one type of alkylenoxy group can be used, or, if two or more alkylenoxy groups are present, two or more types of alkylenoxy groups can be used, and m aa whole number from 1 to 20, where the ring Q b , R 1b , R 2b , A 1b O and m b each independently have the same meaning as the ring Q a , R 1a , R 2a , A 1a O and m a in formula (1) and R 4 a residue obtained by removing two hydroxyl groups from a dicarboxylic acid with 4 to 12 carbon atoms.

Description

TECHNICAL AREA

[0001] The present invention relates to a treatment agent for synthetic fibers, a synthetic fiber and a method for treating a synthetic fiber. TECHNICAL BACKGROUND

[0002] Recent developments have increased the speed of spinning, twisting, and finishing steps in the production of synthetic fibers. This has made the generation of static electricity and fuzz formation on the resulting yarn increasingly likely. To prevent this static electricity and fuzz, a fiber treatment agent with a higher concentration of a functional enhancer that inhibits static electricity and fuzz formation is used, or the amount of treatment agent applied to the synthetic fibers is increased. However, these options are not yet sufficient to prevent static electricity and fuzz formation, and further improvements in antistatic properties are needed.

[0003] Synthetic fibers are produced in various countries and regions; consequently, the conditions for using a treatment agent for synthetic fibers vary depending on these countries and regions. For example, a treatment agent for synthetic fibers is desirable that can be used under a wide temperature range.

[0004] Many treatment agents for synthetic fibers containing polyether (PO / EO copolymer) (see, e.g., patent document 1 and the like) have already been proposed, however, some of these treatment agents for synthetic fibers exhibit insufficient emulsion stability.

[0005] In a treatment agent for synthetic fibers with low emulsion stability, the components separate, for example, during storage in an emulsion preparation tank. If the separated product is allowed to adhere to synthetic fibers, the adhesion of the treatment agent is not uniform, which leads to problems in the subsequent spinning, twisting, and finishing steps.

[0006] Furthermore, a reduction in low-temperature handling properties at temperatures at or below freezing leads to the components of the synthetic fiber treatment agent solidifying, resulting in a lack of uniformity among the components and thus rendering the synthetic fiber treatment agent insufficiently effective. Additionally, this reduction increases the time required to produce an emulsion.

[0007] In other words, improving the emulsion stability and low-temperature handling properties of the treatment agent for synthetic fibers is a factor in increasing the quality of synthetic fibers and is therefore an important task.

[0008] Patent document 2 describes compositions of esters of secondary alcohols or secondary alcohol alkoxylates and a carboxylic acid with an alkyl group having 1 to 26 carbon atoms, an aryl group, a cycloalkyl group, an alkenyl group, and a cycloalkenyl group. Patent document 3 describes a treatment agent for synthetic fibers that imparts antistatic properties. Patent documents 4 and 5 each describe a treatment agent for synthetic fibers comprising cycloalkylalkanol derivatives. LITERATURE FROM THE STATE OF THE TECHNOLOGY PATENT LITERATURE Patent Document 1: JPH10-245729A Patent document 2: JP 2003 - 313 773 A Patent Document 3: CN 1 08 368 671 A Patent document 4: JP 2018 - 40 090 A Patent document 5: US 2014 / 0 134 094 A OVERVIEW OF THE INVENTIONAL PROBLEM

[0009] One object of the present invention is to provide: - a treatment agent for synthetic fibers which gives a synthetic fiber good antistatic properties as well as excellent properties in terms of emulsion stability and handling at low temperatures, - a synthetic fiber to which the treatment agent adheres, as well as - a treatment method for adhering the treatment agent for synthetic fibers to the synthetic fiber. SOLUTION TO THE PROBLEM

[0010] Through careful investigations to solve the aforementioned problem, the inventors have discovered that a cycloalkylalkanol derivative with a specific chemical structure plays an important role in providing a treatment agent for synthetic fibers that imparts good antistatic properties to a synthetic fiber and exhibits excellent properties with regard to emulsion stability and low-temperature handling, thereby enabling the inventors to solve the aforementioned problems.

[0011] The present invention comprises in particular the following items: 1. A treatment agent for synthetic fibers, which has: one or more selected cycloalkylalkanol derivatives, represented by the following formulas (1) and (2): where the ring Q aa cycloalkylene group with 3 to 8 carbon atoms, R 1a a hydrogen atom or an alkyl group with 1 to 12 carbon atoms, R 2a a divalent hydrocarbon group with 1 to 12 carbon atoms, R 3 a hydrogen atom or a residue obtained by removing a hydroxyl group from a monocarboxylic acid with 6 to 22 carbon atoms, A 1a O is an alkylenoxy group with 2 to 4 carbon atoms, where only one type of alkylenoxy group can be used, or, if two or more alkylenoxy groups are present, two or more types of alkylenoxy groups can be used, and m a is a whole number from 1 to 20. where the ring Q b , R 1b , R 2b , A 1b O and m b independently of each other, each have the same meaning as the ring Q a , R 1a , R 2a , A 1aO and m a in formula (1) and R 4 a residue obtained by removing two hydroxyl groups from a dicarboxylic acid with 4 to 12 carbon atoms. 2. The synthetic fiber treatment agent according to point 1, wherein the synthetic fiber treatment agent comprises one or more selected cycloalkylalkanol derivatives represented by formula (1), wherein R 1a a hydrogen atom, or are represented by formula (2), where R 1b a hydrogen atom. 3. The synthetic fiber treatment agent according to point 1 or 2, wherein the synthetic fiber treatment agent comprises one or more selected cycloalkylalkanol derivatives represented by formula (1), wherein R 2a a divalent hydrocarbon group with 2 to 8 carbon atoms, or are represented by formula (2), where R 2ba divalent hydrocarbon group with 2 to 8 carbon atoms. 4. The synthetic fiber treatment according to any one of points 1 to 3, wherein the synthetic fiber treatment comprises one or more selected cycloalkylalkanol derivatives represented by formula (1), wherein R 3 a residue obtained by removing a hydroxyl group from an aliphatic monocarboxylic acid with 6 to 22 carbon atoms, or are represented by formula (2). 5. The treatment agent for synthetic fibers according to any one of points 1 to 4, wherein the treatment agent for synthetic fibers contains the cycloalkylalkanol derivative in an amount of 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 one of points 1 to 5, which furthermore contains a non-ionic surfactant other than the cycloalkylalkanol derivative as well as an ionic surfactant. 7. The treatment agent for synthetic fibers according to one of points 1 to 5, which further comprises a lubricant, a non-ionic surfactant other than the cycloalkylalkanol derivative and an ionic surfactant. 8. The treatment agent for synthetic fibers according to point 6 or 7, wherein the ionic surfactant contains at least one organic phosphate ester selected from an organic phosphate ester P1 represented by formula (3) below, an organic phosphate ester P2 represented by formula (4) below and an organic phosphate ester P3 represented by formula (5) below, where the ring Q b , R 1c , R 2c , A 1c O and m ceach independently have the same meaning as the ring Q a , R 1a , R 2a , A 1a O and m a in formula (1), n is an integer from 2 to 4, R 5 a by removing an oxygen atom from the end chain of “R 1c -Ring Q c -R 2c -O-(A 1c O)m c -“ remaining is, where Q c , R 1c , R 2c , A 1c O and m c each independently have the same meaning as the ring Q a , R 1a , R 2a , A 1a O and m a in formula (1), an alkali metal, an alkaline earth metal (1 / 2), an organic amine salt or a hydrogen atom, and M 1 an alkali metal, an alkaline earth metal (1 / 2), an organic amine salt or a hydrogen atom, where the ring Q d , R 1d , R 2a , A 1d O(OA 1d) and m d each independently have the same meaning as the ring Q a , R 1a , R 2a , A 1a O and m a in formula (1) and M 2 an alkali metal, an alkaline earth metal (1 / 2), an organic amine salt or a hydrogen atom, where the ring Q e , R 1e , R 2e , A 1e O and m e each independently have the same meaning as the ring Q a , R 1a , R 2a , A 1a O and m a in formula (1) and M 3 and M 4 each is 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 one of points 1 to 8 has adhered. 10. A method for treating a synthetic fiber, which has: - Adhesion of the treatment agent for synthetic fibers according to one of points 1 to 8 to a synthetic fiber in an amount of 0.1 mass percent to 5 mass percent relative to the synthetic fiber. ADVANTAGEOUS EFFECTS OF THE INVENTION

[0012] The treatment agent for synthetic fibers, the synthetic fiber and the method for treating a synthetic fiber according to the present invention have an effect such that static electricity and lint formation are prevented due to excellent antistatic properties: this in response to the increasing speed in recent years of the spinning step, the twisting step and the finishing step of synthetic fibers.

[0013] The treatment agent for synthetic fibers according to the present invention exhibits excellent emulsion stability properties, such that the components do not separate even when the emulsion is stored for an extended period. The treatment agent for synthetic fibers is advantageous because it adheres uniformly.

[0014] Furthermore, the treatment agent for synthetic fibers exhibits excellent properties with regard to handling at low temperatures in environments at or below freezing; as a result, problems such as solidification of components of the treatment agent for synthetic fibers do not occur, and the time required to produce an emulsion can be avoided. DESCRIPTION OF THE EXAMPLES OF EXECUTION

[0015] The present invention relates to a treatment agent for synthetic fibers comprising one or more selected cycloalkylalkanol derivatives represented by formulas (1) and (2), a synthetic fiber to which the treatment agent adheres, and a treatment method for adhering the treatment agent to the synthetic fiber.

[0016] The present invention is described in detail below. <cycloalkylalkanolderivat>

[0017] The treatment agent for synthetic fibers according to the present invention contains as an essential component one or more selected cycloalkylalkanol derivatives represented by formulas (1) and (2). (In the formula, this means Ring Q a a cycloalkylene group with 3 to 8 carbon atoms, R 1a a hydrogen atom or an alkyl group with 1 to 12 carbon atoms, R 2a a divalent hydrocarbon group with 1 to 12 carbon atoms, R 3 a hydrogen atom or a residue obtained by removing a hydroxyl group from a monocarboxylic acid with 6 to 22 carbon atoms, A 1a O an alkylenoxy group with 2 to 4 carbon atoms, wherein only one type of alkylenoxy group can be used or two or more types of alkylenoxy groups can be used if two or more alkylenoxy groups are present, and m a (a whole number from 1 to 20) (In the formula, the ring Q b , R 1b , R 2b , A 1b O and m b Each independently has the same meaning as the ring Q a , R 1a , R 2a , A 1a O and m a in formula (1) and R 4 is a residue obtained by removing a hydroxyl group from a dicarboxylic acid with 4 to 12 carbon atoms.)

[0018] The cycloalkylalkanol derivative represented by formula (1) in the present invention is a cycloalkylalkanol ester of a monocarboxylic acid having 6 to 22 carbon atoms, a polyadduct of alkylene oxide for cycloalkylalkanol, or an ester of a monocarboxylic acid having 6 to 22 carbon atoms and a polyadduct of alkylene oxide for cycloalkylalkanol. The cycloalkylalkanol derivative represented by formula (2) in the present invention is a cycloalkylalkanol diester of a dicarboxylic acid having 4 to 12 carbon atoms or a diester of a dicarboxylic acid having 4 to 12 carbon atoms and a polyadduct of alkylene oxide for cycloalkylalkanol.

[0019] The Ring Q 3 in formula (1) and the ring Q b In formula (2) there is preferably each a cycloalkylene group with 5 to 8 carbon atoms independently and particularly preferably a cycloalkylene group with 5 or 6 carbon atoms.

[0020] R 1a in formula (1) and R 1b In formula (2) there is preferably a hydrogen atom or an alkyl group with 6 to 10 carbon atoms, preferably a hydrogen atom or an alkyl group with 6 to 8 carbon atoms, and most preferably a hydrogen atom.

[0021] The divalent hydrocarbon groups with 1 to 12 carbon atoms in R 2a in formula (1) and R 2b In formula (2), each group can be independently linear or branched, and each group can be independently saturated or unsaturated. The divalent hydrocarbon groups in R 2a in formula (1) and R 2b in formula (2) each independently preferably a linear or branched alkylene group with 1 to 12 carbon atoms, preferably a linear or branched alkylene group with 2 to 8 carbon atoms and particularly preferably a linear alkylene group with 2 to 8 carbon atoms.

[0022] The monocarboxylic acid in one hydrogen atom or the residue obtained by removing a hydroxyl group from a monocarboxylic acid with 6 to 22 carbon atoms in R 3 In formula (1), either a saturated monocarboxylic acid or an unsaturated monocarboxylic acid can be used. Here, R is... 3 preferably a hydrogen atom or a residue obtained by removing a hydroxyl group from a saturated or unsaturated monocarboxylic acid with 8 to 20 carbon atoms, and is preferably a residue obtained by removing a hydroxyl group from a saturated or unsaturated monocarboxylic acid with 8 to 20 carbon atoms.

[0023] The dicarboxylic acid in the residue R obtained by removing two hydroxyl groups from a dicarboxylic acid with 4 to 12 carbon atoms 4 In formula (2), the dicarboxylic acid can be a saturated or unsaturated aliphatic dicarboxylic acid or an aromatic dicarboxylic acid. The dicarboxylic acid is represented by the residue R obtained by removing two hydroxyl groups from a dicarboxylic acid with 4 to 12 carbon atoms. 4 in formula (2) preferably a residue obtained by removing two hydroxyl groups from a saturated or unsaturated aliphatic dicarboxylic acid having 4 to 12 carbon atoms, particularly preferably a residue obtained by removing two hydroxyl groups from a saturated aliphatic dicarboxylic acid having 4 to 12 carbon atoms.

[0024] If A 1a O in formula (1) and A 1b In formula (2), where O has two or more types of alkylenoxy groups with 2 to 4 carbon atoms, the alkylenoxy groups can each be independently randomly dispersed, blocked, or mixed. In this case, A 1a O in formula (1) and A 1b O in formula (2) each independently preferably only one type or two types of alkylenoxy groups with 2 or 3 carbon atoms. m a in formula (1) and m b In formula (2), the numbers represent an average number of moles of the alkylenoxy groups with 2 to 4 carbon atoms; each mole independently represents an integer from 1 to 20, preferably an integer from 1 to 15. In a non-inventive embodiment, m a It could also be 0.

[0025] In the present invention, the cycloalkylalkanol derivatives represented by formulas (1) and (2) are prepared, for example, by esterification of cycloalkylalkanols with monocarboxylic acids or dicarboxylic acids, by addition polymerization of alkylene oxides with 2 or 4 carbon atoms - randomly, blocked or mixed - for cycloalkylalkanols, or by esterification of polyadducts of alkylene oxide for cycloalkanol with monocarboxylic acids or dicarboxylic acids.

[0026] The treatment agent for synthetic fibers according to the present invention contains the cycloalkylalkanol derivatives represented by formulas (1) and (2) in an amount of preferably 0.01% to 30% by mass, more preferably 0.1% to 25% by mass, more preferably 0.2% to 20% by mass and most preferably 0.2% to 10% by mass, in relation to a total mass of the treatment agent for synthetic fibers.

[0027] The treatment agent for synthetic fibers according to the present invention preferably comprises, in addition to the cycloalkylalkanol derivatives represented by formulas (1) and (2), a non-ionic surfactant and an ionic surfactant.

[0028] Furthermore, the treatment agent for synthetic fibers according to the present invention preferably comprises, in addition to the cycloalkylalkanol derivatives represented by formulas (1) and (2), a non-ionic surfactant and a lubricant as well as an ionic surfactant.

[0029] The non-ionic surfactant and lubricant, other than the cycloalkylalkanol derivatives represented by formulas (1) and (2) and the ionic surfactant, which can be used in the treatment agent for synthetic fibers according to the present invention, are described below. <Außer den Cycloalkylalkanolderivaten vorhandenes nichtionisches Tensid>

[0030] There are no restrictions on the nonionic surfactant present in addition to the cycloalkylalkanol derivatives represented by formulas (1) and (2), which can be used in the treatment agent for synthetic fibers according to the present invention. Examples of the nonionic surfactant are: (1) Compounds in which an alkylene oxide having 2 to 4 carbon atoms has been added to an organic acid, an organic alcohol, an organic amine and / or an organic amide, such as polyoxyethylene oleate, polyoxyethylene methyl ether laurate, polyoxyethylene octyl ether laurate, polyoxyethylene polyoxypropylene tridecyl ether palmitate, polyoxyethylene dioleate, polyoxyethylene lauryl ether, polyoxyethylene lauryl ether methyl ether, polyoxybutylene oleyl ether, polyoxyethylene polyoxypropylene butyl ether, polyoxyethylene polyoxypropylene octyl ether, polyoxyethylene polyoxypropylene trimethylol propyl ether, polyoxyethylene polyoxypropylene nonyl ether, polyoxyethylene polyoxypropylene propylene glycol ether, polyoxyethylene polyoxypropylene lauryl ether, polyoxyethylene polyoxypropylene isotridecyl ether, Polyoxyethylene tetradecyl ether, polyoxyethylene glyceryl ether, polyoxyethylene laurylamino ether and polyoxyethylene lauric ether; (2) Polyoxyalkylene fatty acid esters with polyhydric alcohol, such as polyoxyalkylene sorbitan trioleate, polyoxyalkylene castor oil ether, polyoxyalkylene with hydrogenated castor oil ether and polyoxyalkylene with hydrogenated castor oil ether trioleate; (3) Alkylamides, such as diethanolamine monolauroamide; and (4) Polyoxyalkylene fatty acid amides, such as polyoxyethylenediamine monooleylamide.

[0031] These nonionic surfactants can be used alone or in combination with two or more other types. In the present invention, EO and PO at the end of the compound name denote an ethylene oxide adduct and a propylene oxide adduct, respectively, and the number following EO or PO represents the number of moles of ethylene oxide or propylene oxide to be added. The numerical values ​​following EO and PO represent the average number of moles added. <Außer den Cycloalkylalkanolderivaten vorhandenes Schmiermittel>

[0032] In addition to the cycloalkylalkanol derivatives represented by formulas (1) and (2), which can be used in the synthetic fiber treatment according to the present invention, known lubricants can be used as lubricants in the synthetic fiber treatment, such as, for example, (1) Ester compounds of an aliphatic monoalcohol and an aliphatic monocarboxylic acid, such as butyl stearate, octyl stearate, oleyl laurate, oleyl oleate, isopentacosanyl isostearate, octyl palmitate, isotridecyl stearate and lauroleate; (2) Ester compounds of an aliphatic polyhydric alcohol and an aliphatic monocarboxylic acid, such as 1,6-hexanediol didecanoate, trimethylolpropane monooleate monolaurate, sorbitan trioleate, sorbitan monooleate, sorbitan tristearate, sorbitan distearate, sorbitan monostearate and glycerol monolaurate; (3) Ester compounds of an aliphatic monoalcohol and an aliphatic polycarboxylic acid, such as dilauryl adipate, diolyl lazelate, diisocetyl thiodipropionate and bispolyoxyethylene lauryl adipate; (4) Ester compounds of an aromatic monoalcohol and an aliphatic monocarboxylic acid, such as benzyl oleate, benzyl laurate and polyoxypropylene benzyl stearate; (5) Ester compounds of an aromatic polyhydric alcohol and an aliphatic monocarboxylic acid, such as bisphenol A dilaurate and polyoxyethylene bisphenol A dilaurate; (6) Ester compounds of an aliphatic monoalcohol and an aromatic polyvalent carboxylic acid, such as bis(2-ethylhexyl) phthalate, diisostearyl isophthalate and trioctyl trimellitate; (7) natural fats and oils, such as coconut oil, rapeseed oil, sunflower oil, soybean oil, castor oil, sesame oil, fish oil and beef tallow; and (8) Mineral oils.

[0033] These lubricant components can be used alone or in combination with two or more other types. <Ionisches Tensid>

[0034] In the treatment agent for synthetic fibers according to the present invention, at least one organic phosphate ester, selected from an organic phosphate ester P1 represented by formula (3) below, an organic phosphate ester P2 represented by formula (4) below and an organic phosphate ester P3 represented by formula (5) below, is preferably used as an ionic surfactant. (In the formula, the ring Q c , R 1c , R 2c , A 1c O and m c Each independently has the same meaning as the ring Q a , R 1a , R 2a , A 1a O and m a in formula (1), n is an integer from 2 to 4, R 5 is formed by removing an oxygen atom from the end chain of “R 1c -Ring Q c -R 2c -O-(A 1c O)m c -" retained remainder, wherein the ring Q c , R 1c , R 2c , A 1c O and m c each independently have the same meaning as Q a , R 1a , R 2a , A 1a O and m a in formula (1), an alkali metal, an alkaline earth metal (1 / 2), an organic amine salt or a hydrogen atom, M 1 is an alkali metal, an alkaline earth metal (1 / 2), an organic amine salt, or a hydrogen atom.) (In the formula, the ring Q d , R 1d , R 2a , A 1d O(OA 1d ) and m d Each independently has the same meaning as the ring Q a , R 1a , R 2a , A 1a O and m a in formula (1), M 2 is an alkali metal, an alkaline earth metal (1 / 2), an organic amine salt, or a hydrogen atom.) (In the formula, the ring Q e , R 1e , R 2e , A 1e O and m e Each independently has the same meaning as the ring Q a , R 1a , R 2a , A 1a O and m a in formula (1), M 3 and M 4 are each independently an alkali metal, an alkaline earth metal (112), an organic amine salt or a hydrogen atom.)

[0035] Preferred examples for the ring Q c , R 1c , R 2c , A 1c O and m c in formula (3), the ring Q d , R 1d , R 2d , A 1d O (O A1 d) and m d in formula (4) and the ring Q e , R 1c , R 2e , A 1e O and m e In formula (5), the values ​​are the same as for the ring Q, regardless of the specific case. a , R 1a , R 2a , A 1a O and m a in formula (1). R 5 in formula (3) preferably a by removing an oxygen atom at the end of “R 1c -Ring Q c -R 2c -O-(A 1c O)m c -" retained remainder (it should be noted that the ring Q c , R 1c , R 2c , A 1c O and m c each independently have the same meaning as the ring Q a , R 1a , R 2a , A 1a O and m a in formula (1)). M 1 in formula (3), M 2 in formula (4) as well as M 3 and M 4 In formula (5) preferably each is an alkali metal or an organic amine salt independently.

[0036] The sum of the ¹³P NMR integration fractions belonging to the organic phosphate ester P1 represented by formula (3), the organic phosphate ester P2 represented by formula (4), and the organic phosphate ester P3 represented by formula (5) is defined as 100%. In this case, the ¹³P NMR integration fraction belonging to the organic phosphate ester P3 represented by formula (5) is 30% to 80%, preferably 35% to 75%, and particularly preferably 40% to 70%.

[0037] The term ³¹P-NMR integration fraction (the ³¹P-NMR integration fractions (in %) belonging to the organic phosphate esters P1, P2, and P3) is understood to mean a value that can be calculated using the following formulas (a) to (c) by applying a measurement from an application of ³¹P-NMR (trade name: MERCURY Plus NMR Spectrometer System, manufactured by VALIAN, Inc., 300 MHz) to the organic phosphate esters P1, P2, and P3 under conditions in which an excess amount of KOH is added to an alkali salt of the organic phosphate ester or the like to adjust a pH of at least 12. A solvent mixture of heavy water and tetrahydrofuran with a volume ratio of 8:2 may be used.

[0038] In formulas (a) to (c) “P-Chem. 1” represents a P-NMR integration value corresponding to the organic phosphate ester P1 represented by formula (3), “P-Chem. 2” represents a P-NMR integration value corresponding to the organic phosphate ester P2 represented by formula (4) and “P-Chem. 3” represents a P-NMR integration value corresponding to the organic phosphate ester P3 represented by formula (5). [Formula 1] P−NMR−integration fraction (%) of the organic phosphate ester P1=(P−Chem.1)÷(P−Chem.1+P−Chem.2+P−Chem.3)×100 [Formula 2] P−NMR−integration fraction (%) of the organic phosphate ester P2=(P−Chem.2)÷(P−Chem.1+P−Chem.2+P−Chem.3)×100 [Formula 3] P−NMR−integration fraction (%) of the organic phosphate ester P3=(P−Chem.3)÷(P−Chem.1+P−Chem.2+P−Chem.3)×100

[0039] The present invention does not impose any restrictions regarding a process for preparing the organic phosphate esters represented by formulas (3) to (5). The organic phosphate ester is prepared, for example, by mixing and esterifying with a phosphorylating agent such as phosphoric anhydride, cycloalkylalkanols, or substances obtained by addition polymerization (random, blocked, or mixed) of alkylene oxides having 2 to 4 carbon atoms and cycloalkylalkanols, or by further neutralization of the resulting mixture with a base. <Weitere ionische Tenside>

[0040] The treatment agent for synthetic fibers according to the present invention may also contain further ionic surfactants. Examples of further ionic surfactants include anionic surfactants, cationic surfactants, and amphoteric surfactants, which are used as treatment agents for fibers. Specific examples of an anionic surfactant include: (1) an ionic surfactant of the carboxylic acid soap type, such as a potassium acetate salt, a potassium octanate salt, a potassium oleate salt, a sodium oleate salt and a potassium alkenyl succinate salt; (2) an ionic surfactant of the sulfonic acid ester type, such as a secondary alkanesulfonate sodium salt, a dodecylbenzenesulfonate sodium salt and a sodium dioctyl sulfosuccinate salt; (3) an ionic surfactant of the sulfuric acid ester type, such as a polyoxyethylene lauryl sulfate sodium salt, a hexadecyl sulfate potassium salt, a beef tallow sulfide oil and a castor oil sulfide oil; and (4) an organic phosphate ester salt such as a dodecyl phosphate sodium salt, an oleyl phosphate potassium salt, a hexadecyl phosphate potassium salt, an octadecyl phosphate potassium salt, an oleyl phosphate triethanolamine salt and a salt of a polyoxyethylene oleyl ether phosphate ester and a polyoxyethylene lauryl amino ether.

[0041] Examples of cationic surfactants include quaternary ammonium salts, such as tetrabutylammonium salts.

[0042] Examples of amphoteric surfactants include an organic amine oxide, such as dimethylstearylamine oxide; a betaine-type amphoteric surfactant, such as octyldimethylammonium acetate; and an amphoteric alanine-type surfactant, such as N,N-bis(2-carboxyethyl)-octylamine sodium. These components can be used individually or in combination with two or more such types.

[0043] If the synthetic fiber treatment according to the present invention comprises the cycloalkylalkanol derivatives represented by formula (1) and formula (2), the non-ionic surfactant other than the cycloalkylalkanol derivative, and the ionic surfactant, the synthetic fiber treatment contains the non-ionic surfactant other than the cycloalkylalkanol derivative in an amount preferably of 50% to 99% by mass, more preferably of 60% to 99% by mass, and more preferably of 65% to 99% by mass, and the synthetic fiber treatment contains the ionic surfactant in an amount preferably of 0.01% to 10% by mass, more preferably of 0.1% to 10% by mass, and more preferably of 0.5% to 5% by mass with respect to the total mass of the synthetic fiber treatment.

[0044] If the treatment agent for synthetic fibers according to the present invention contains at least one organic phosphate ester, selected from the organic phosphate ester P1 represented by formula (3), the organic phosphate ester P2 represented by formula (4) and the organic phosphate ester P3 represented by formula (5), as an ionic surfactant, the total amount of the organic phosphate esters represented by formulas (3) to (5) is preferably 0.01% to 10% by mass, more preferably 0.05% to 5% by mass and particularly preferably 0.1% to 3% by mass in relation to the total mass of the treatment agent for synthetic fibers.

[0045] If the treatment agent for synthetic fibers according to the present invention comprises the cycloalkylalkanol derivatives represented by formula (1) and formula (2), a non-ionic surfactant, a lubricant and an ionic surfactant other than the cycloalkylalkanol derivatives, the treatment agent for synthetic fibers contains the non-ionic surfactant other than the cycloalkylalkanol derivatives in an amount preferably of 5% to 60% by mass, preferably of 10% to 60% by mass, and particularly preferably of 10% to 50% by mass.The treatment agent for synthetic fibers contains the lubricant, in addition to the cycloalkylalkanol derivatives, in an amount of preferably 30% to 80% by mass, more preferably 30% to 70% by mass, and more preferably 40% to 70% by mass, and the treatment agent for synthetic fibers contains the ionic surfactant in an amount of preferably 0.1% to 25% by mass, more preferably 0.5% to 20% by mass, more preferably 1.0% to 15% by mass.

[0046] If the treatment agent for synthetic fibers comprises at least one organic phosphate ester selected from the organic phosphate ester P1 represented by formula (3), the organic phosphate ester P2 represented by formula (4) and the organic phosphate ester P3 represented by formula (5), the total amount of the organic phosphate esters represented by formulas (3) to (5) is preferably 0.01% to 10% by mass, more preferably 0.05% to 5% by mass and particularly preferably 0.1% to 3% by mass in relation to the total mass of the treatment agent for synthetic fibers.

[0047] The treatment agent for synthetic fibers having this composition is suitable as a treatment agent for synthetic fibers to be used in the spinning and drawing step. <Weitere Komponenten>

[0048] The treatment agent for synthetic fibers according to the present invention may further contain components that are generally used for a treatment agent for synthetic fibers, such as a stabilizer, an antistatic agent, an antifoaming agent (a silicone-based compound, a mineral oil or the like), a binder, an antioxidant and a UV absorber, for quality assurance of the treatment agent, up to an amount such that the components do not restrict the effects of the present invention. <Synthetische Faser>

[0049] The synthetic fiber according to the present invention is a synthetic fiber to which the synthetic fiber treatment agent according to the present invention adheres. There are no restrictions regarding the synthetic fiber to which the synthetic fiber treatment agent according to the present invention adheres. Examples of the synthetic fiber include (1) polyester-based fibers, such as polyethylene terephthalate, polypropylene terephthalate and polylactide esters, (2) polyamide-based fibers, such as Nylon 6 and Nylon 66, (3) polyacrylic-based fibers, such as polyacrylic and moderacryl, (4) polyolefin-based fibers, such as polyethylene and polypropylene, and polyurethane-based fibers.

[0050] The effect of the treatment agent for synthetic fibers becomes particularly evident when the treatment agent for synthetic fibers according to the present invention adheres to polyester-based fibers or polyamide-based fibers.

[0051] There is no limitation regarding the proportion of the treatment agent for synthetic fibers to adhere to the synthetic fiber according to the present invention. However, the proportion in which the treatment agent for synthetic fibers adheres to the synthetic fiber according to the present invention is preferably 0.1% to 3% by mass, more preferably 0.3% to 1.2% by mass of the synthetic fiber. This constituent feature further improves the effect of the present invention.

[0052] There is no restriction regarding the number of steps involved in the adhesion of the treatment agent to synthetic fibers according to the present invention. Examples of such steps include a spinning step and a step in which spinning and drawing are performed simultaneously. Examples of methods for adhering the treatment agent to a synthetic fiber according to the present invention include, but are not limited to, an oil-feeding method using rollers, an oil-feeding method using a metering pump, an immersion oil-feeding method, and a spray oil-feeding method. Furthermore, examples of the form of the treatment agent to be adhered to the synthetic fiber according to the present invention include, but are not limited to, the following: undiluted form, a solution in an organic solvent, and an aqueous solution, with an aqueous solution being preferred.When the aqueous solution of the treatment agent according to the present invention is applied, the amount in which the treatment agent according to the present invention can be applied is 0.1% to 3% by mass, preferably 0.3% to 1.2% by mass, with respect to the synthetic fibers.

[0053] The treatment agent for synthetic fibers according to the present invention contains as an essential component the cycloalkylalkanol derivatives represented by formula (1) and formula (2); thus, the generation of static electricity and the formation of lint as a reaction to the increasing speed of the spinning step, the false twisting step and the finishing step of synthetic fibers in recent years can be satisfactorily prevented.

[0054] Furthermore, the synthetic fiber treatment according to the present invention exhibits excellent emulsion stability, meaning that the components do not separate even when the emulsion is stored for extended periods. Moreover, the synthetic fiber treatment according to the present invention has excellent low-temperature handling properties in environments at or below freezing, thereby avoiding problems such as solidification of the components of the synthetic fiber treatment.It is evident from the above explanations that the treatment agent for synthetic fibers according to the present invention is useful for a uniform adhesion of the treatment agent for synthetic fibers, so that the functionality is sufficiently effective, and that the treatment agent for synthetic fibers according to the present invention can avoid the time required to produce an emulsion. EXAMPLE

[0055] The present invention is described below by means of examples, the technical scope of which is not limited to these examples. In the following examples and comparative examples, "proportion(s)" means "mass fraction(s)" and "%" means "mass percent". <Synthese von Cycloalkylalkanolderivat> (A-1)

[0056] 184 g of 6-cyclohexylhexyl alcohol and 282 g of oleic acid were placed in a reaction vessel and melted in a nitrogen atmosphere at 75°C. Then, 0.6 g of paratoluenesulfonic acid was added as a catalyst, followed by a reaction lasting 4 hours at 120°C and a reduced pressure of 2 mmHg, during which time the water produced was removed from the reaction system. Next, the pressure was restored to atmospheric pressure at 105°C in a nitrogen atmosphere, an adsorbent was added to bind the catalyst, and the resulting mixture was filtered at 90°C to obtain A-1. A-1 is an embodiment not according to the invention.

[0057] “A-1” is a cycloalkylalkanol compound represented by formula (1), in which the ring Q a a cyclohexylene group, R 1a a hydrogen atom, R 2a a hexylene group, R 3 an oleyl group and m a = 0. A 99% purity of “A-1” as a cycloalkylalkanol derivative according to the present invention was determined by gas chromatography coupled with mass spectrometry (hereinafter referred to as “GC-MS”). (A-2)

[0058] A-2 was obtained in the same manner as in the manufacturing process of “A-1”, except that 198 g of 7-cyclohexylheptyl alcohol was used instead of 6-cyclohexylhexyl alcohol.

[0059] “A-2” is a cycloalkylalkanol compound represented by formula (1), in which the ring Q a a cyclohexylene group, R 1a a hydrogen atom, R 2a a heptylene group, R 3 an oleyl group and m a = 0. A 98% purity of “A-2” as a cycloalkylalkanol derivative according to the present invention was determined by GC-MS. A-2 is also a non-inventive embodiment. (A-3)

[0060] 198 g of 7-cyclohexylheptyl alcohol were placed in an autoclave, 0.3 g of potassium hydroxide were added as a catalyst, and the autoclave was then adequately filled with nitrogen. During stirring, 132 g of ethylene oxide were injected at a pressure of 0.0 to 0.4 MPa, and a reaction temperature of 110°C to 120°C was maintained to carry out an addition polymerization over a period of approximately 5 hours. The resulting product was then transferred to a flask, and the potassium hydroxide (as catalyst) was neutralized with phosphoric acid. The potassium phosphate generated by the neutralization was filtered off to obtain a polyadduct of ethylene oxide for 7-cyclohexylheptyl alcohol.

[0061] After melting 165 g of the obtained polyadduct and 141 g of oleic acid in a nitrogen atmosphere at 75°C, 0.3 g of paratoluenesulfonic acid was added as a catalyst. The reaction was then carried out for 4 hours at 120°C and a reduced pressure of 2 mmHg, with the water produced being removed from the reaction system. Next, the pressure was restored to atmospheric pressure at 105°C in a nitrogen atmosphere, an adsorbent was added to bind the catalyst, and the resulting mixture was filtered at 90°C to obtain A-3.

[0062] “A-3” is a cycloalkylalkanol derivative compound represented by formula (1), in which the ring Q a a cyclohexylene group, R 1a a hydrogen atom, R 2a a heptylene group, R 3 an oleyl group, A 1a O an EO (ethylene oxy group) and m a = 3. A 97% purity of “A-3” as a cycloalkylalkanol derivative according to the present invention was determined by GC-MS. (A-4)

[0063] A-4 was obtained in the same manner as in the manufacturing process of “A-3”, except that 184 g of 6-cyclohexylhexyl alcohol were used instead of 7-cyclohexylheptyl alcohol, 264 g of ethylene oxide and 116 g of propylene oxide were used instead of 132 g of ethylene oxide, and 82 g of caprylic acid were used instead of 141 g of oleic acid.

[0064] “A-4” is a cycloalkylalkanol derivative compound represented by formula (1), in which the ring Q a a cyclohexylene group, R 1a a hydrogen atom, R 2a a hexylene group, R 3 an octyl group, A 1a O 6 mol EO (ethylene oxy group) and 2 mol PO (propylene oxy group) and m a = 8. A 95% purity of “A-4” as a cycloalkylalkanol derivative according to the present invention was determined by GC-MS. (A-5)

[0065] 184 g of 6-cyclohexylhexyl alcohol were placed in an autoclave, 0.3 g of potassium hydroxide were added as a catalyst, and the autoclave was then adequately filled with nitrogen. While stirring, 88 g of ethylene oxide and 116 g of propylene oxide were injected at a pressure of 0.0 to 0.4 MPa, and a reaction temperature of 110°C to 120°C was maintained to carry out an addition polymerization over a period of approximately 5 hours. The resulting product was then transferred to a flask, and the potassium hydroxide (as a catalyst) was neutralized with phosphoric acid. The potassium phosphate generated by the neutralization was filtered off to obtain a polyadduct of ethylene oxide and propylene oxide for 7-cyclohexylheptyl alcohol.

[0066] After melting 194 g of the obtained polyadduct and 37 g of adipic acid in a nitrogen atmosphere at 75 °C, 0.3 g of paratoluenesulfonic acid was added as a catalyst. The reaction was then carried out for 4 hours at 120 °C and a reduced pressure of 2 mmHg, with the water produced being removed from the reaction system. Next, the pressure was restored to atmospheric pressure at 105 °C in a nitrogen atmosphere, an adsorbent was added to bind the catalyst, and the resulting mixture was filtered at 90 °C to obtain A-5. “A-5” is represented by formula (2)

[0067] Cycloalkylalkanol derivative compound in which the ring Q b a cyclohexylene group, R 1b a hydrogen atom, R 2b a hexylene group, R 4 an adipyl group, A 1b O 2 mol EO (ethylene oxy group) and 2 mol PO (propylene oxy group) and m b = 4. A 96% purity of “A-5” as a cycloalkylalkanol derivative according to the present invention was determined by GC-MS. (A-6)

[0068] A-6 was obtained in the same manner as in the manufacturing process of “A-3”, except that 128 g of 2-cyclohexylethyl alcohol were used instead of 7-cyclohexylheptyl alcohol and 142 g of stearic acid were used instead of 141 g of oleic acid.

[0069] “A-6” is a cycloalkylalkanol derivative compound represented by formula (1), in which the ring Q a a cyclohexylene group, R 1a a hydrogen atom, R 2a an ethylene group, R 3 a stearyl group, A 1a O an EO (ethylene oxy group) and m a = 3. A 97% purity of “A-6” as a cycloalkylalkanol derivative according to the present invention was confirmed by GC-MS. (A-7)

[0070] 128 g of 2-cyclohexylethyl alcohol were placed in an autoclave, 0.3 g of potassium hydroxide were added as a catalyst, and the autoclave was then adequately filled with nitrogen. During stirring, 352 g of ethylene oxide and 116 g of propylene oxide were injected at a pressure of 0.0 to 0.4 MPa, and a reaction temperature of 110°C to 120°C was maintained to carry out an addition polymerization over a period of approximately 5 hours. The resulting product was then transferred to a flask, and the potassium hydroxide (as a catalyst) was neutralized with phosphoric acid. The potassium phosphate generated by the neutralization was filtered off to obtain a polyadduct A-7 of ethylene oxide and propylene oxide for 2-cyclohexylethyl alcohol.

[0071] “A-7” is a cycloalkylalkanol derivative compound represented by formula (1), in which the ring Q a a cyclohexylene group, R 1a a hydrogen atom, R 2a an ethylene group, R 3 a hydrogen atom, A 1a O 8 mol EO (ethylene oxy group) and 2 mol PO (propylene oxy group) and m a = 10. A 100% purity of “A-7” as a cycloalkylalkanol derivative according to the present invention was determined by GC-MS. (A-8)

[0072] A-8 was obtained in the same manner as in the manufacturing process of “A-7”, except that 198 g of 7-cyclohexylheptyl alcohol were used instead of 2-cyclohexylethyl alcohol, and 264 g of ethylene oxide and 116 g of propylene oxide were used instead of 352 g of ethylene oxide and 116 g of propylene oxide.

[0073] “A-8” is a cycloalkylalkanol derivative compound represented by formula (1), in which the ring Q a a cyclohexylene group, R 1a a hydrogen atom, R 2a a heptylene group, R 3 a hydrogen atom, A 1a O 6 mol EO (ethylene oxy group) and 2 mol PO (propylene oxy group) and m a = 8. A 100% purity of “A-8” as a cycloalkylalkanol derivative according to the present invention was determined by GC-MS. (A-9)

[0074] A-9 was obtained in the same manner as in the manufacturing process of “A-7”, except that 184 g of 6-cyclohexylhexyl alcohol were used instead of 2-cyclohexylethyl alcohol and 638 g of propylene oxide were used instead of 116 g of propylene oxide.

[0075] “A-9” is a cycloalkylalkanol derivative compound represented by formula (1), in which the ring Q a a cyclohexylene group, R 1a a hydrogen atom, R 2a a hexylene group, R 3 a hydrogen atom, A 1a O 8 mol EO (ethylene oxy group) and 11 mol PO (propylene oxy group) and m a = 19. A 100% purity of “A-9” as a cycloalkylalkanol derivative according to the present invention was determined by GC-MS. (A-10)

[0076] A-10 was obtained in the same manner as in the manufacturing process of “A-7”, except that 184 g of 6-cyclohexylhexyl alcohol were used instead of 2-cyclohexylethyl alcohol and 348 g of propylene oxide were used instead of 352 g of ethylene oxide and 116 g of propylene oxide.

[0077] “A-10” is a cycloalkylalkanol derivative compound represented by formula (1), in which the ring Q a a cyclohexylene group, R 1a a hydrogen atom, R 2a a hexylene group, R 3 a hydrogen atom, A 1a O 6 mol PO (propylene oxy group) and m a = 6. A 100% purity of “A-10” as a cycloalkylalkanol derivative according to the present invention was determined by GC-MS. (A-11)

[0078] A-11 was obtained in the same manner as in the manufacturing process of “A-7”, except that 282 g of 8-(2-Octylcyclopropyl)octyl alcohol were used instead of 2-cyclohexylethyl alcohol, and 132 g of ethylene oxide and 174 g of propylene oxide were used instead of 352 g of ethylene oxide and 116 g of propylene oxide.

[0079] “A-11” is a cycloalkylalkanol derivative compound represented by formula (1), in which the ring Q a a 1,2-cyclopropylene group, R 1a an octyl group, R 2a an octylene group, R 3 a hydrogen atom, A 1a O 3 mol EO (ethylene oxy group) and 3 mol PO (propylene oxy group) and m a = 6. A 100% purity of “A-11” as a cycloalkylalkanol derivative according to the present invention was determined by GC-MS. (A-12)

[0080] A-12 was obtained in the same manner as in the manufacturing process of “A-7”, except that 72 g of 6-cyclopropylmethyl alcohol were used instead of 2-cyclohexylethyl alcohol and 440 g of ethylene oxide were used instead of 352 g of ethylene oxide and 116 g of propylene oxide.

[0081] “A-12” is a cycloalkylalkanol derivative compound represented by formula (1), in which the ring Q a a cyclopropylene group, R 1a a hydrogen atom, R 2a a methylene group, R 3 a hydrogen atom, A 1a O 10 mol EO (ethylene oxy group) and m a = 10. A 100% purity of “A-12” as a cycloalkylalkanol derivative according to the present invention was determined by GC-MS. <Synthese von organischem Phosphatester>(B-1)

[0082] 184 g of 6-cyclohexylhexyl alcohol were placed in an autoclave, 0.3 g of potassium hydroxide were added as a catalyst, and the autoclave was then adequately filled with nitrogen. During stirring, 220 g of ethylene oxide were injected at a pressure of 0.0 to 0.4 MPa, and a reaction temperature of 110°C to 120°C was maintained to carry out an addition polymerization over a period of approximately 5 hours. The resulting product was then transferred to a flask, and the potassium hydroxide (as catalyst) was neutralized with phosphoric acid. The potassium phosphate generated by the neutralization was filtered off to obtain a polyadduct of ethylene oxide for 6-cyclohexylhexyl alcohol.

[0083] 202 g of the obtained polymer were placed in a flask, and 24 g of phosphoric anhydride were gradually added to the flask over a period of 1 hour at 65°C to 70°C, while stirring. A maturation reaction then took place over a period of 3 hours at 65°C to 70°C. After cooling the reaction product to room temperature, 28 g of potassium hydroxide were gradually added to neutralize the product and obtain an organic phosphate ester B-1.

[0084] For “B-1”, the P-NMR integration contributions of P1 to P3 were 0%, 48%, and 52%, respectively, when the sum of the integration contributions assigned to the organic phosphate ester P1 represented by formula (3) of the present application, the organic phosphate ester P2 represented by formula (4) of the present application, and the organic phosphate ester P3 represented by formula (5) of the present application was defined as 100%. (B-2)

[0085] 128 g of 2-cyclohexylethyl alcohol were placed in an autoclave, 0.3 g of potassium hydroxide were added as a catalyst, and the autoclave was then adequately filled with nitrogen. During stirring, 174 g of propylene oxide were injected at a pressure of 0.0 to 0.4 MPa, and a reaction temperature of 110°C to 120°C was maintained to carry out an addition polymerization over a period of approximately 5 hours. The resulting product was then transferred to a flask, and the potassium hydroxide (as catalyst) was neutralized with phosphoric acid. The potassium phosphate generated by the neutralization was filtered off to obtain a polyadduct of propylene oxide for 2-cyclohexylethyl alcohol.

[0086] 151 g of the obtained polymer were placed in a flask, and 22 g of phosphoric anhydride were gradually added to the flask over a period of 1 hour at 65°C to 70°C, while stirring. A maturation reaction then took place over a period of 3 hours at 65°C to 70°C. After cooling the reaction product to room temperature, 87 g of dibutylethanolamine were gradually added to neutralize the product and obtain an organic phosphate ester B-2.

[0087] For “B-2”, the P-NMR integration contributions of P1 to P3 were 12%, 43%, and 45%, respectively, when the sum of the integration contributions assigned to the organic phosphate ester P1 represented by formula (3) of the present application, the organic phosphate ester P2 represented by formula (4) of the present application, and the organic phosphate ester P3 represented by formula (5) of the present application was defined as 100%. (B-3)

[0088] 198 g of 7-cyclohexylheptyl alcohol were placed in an autoclave, 0.3 g of potassium hydroxide were added as a catalyst, and the autoclave was then adequately filled with nitrogen. During stirring, 264 g of ethylene oxide and 116 g of propylene oxide were injected at a pressure of 0.0 to 0.4 MPa, and a reaction temperature of 110°C to 120°C was maintained to carry out an addition polymerization over a period of approximately 5 hours. The resulting product was then transferred to a flask, and the potassium hydroxide (as a catalyst) was neutralized with phosphoric acid. The potassium phosphate generated by the neutralization was filtered off to obtain a polyadduct of ethylene oxide and propylene oxide for 7-cyclohexylheptyl alcohol.

[0089] 289 g of the obtained polymer were placed in a flask, and 23 g of phosphoric anhydride were gradually added over a period of 1 hour at 65°C to 70°C while stirring; a maturation reaction then took place over a period of 3 hours at 65°C to 70°C. After cooling the reaction product to room temperature, 28 g of potassium hydroxide were gradually added to neutralize the product and obtain an organic phosphate ester B-3.

[0090] For “B-3”, the P-NMR integration contributions of P1 to P3 were 5%, 47%, and 48%, respectively, when the sum of the integration contributions assigned to the organic phosphate ester P1 represented by formula (3) of the present application, the organic phosphate ester P2 represented by formula (4) of the present application, and the organic phosphate ester P3 represented by formula (5) of the present application was defined as 100%. (B-4)

[0091] 184 g of 6-cyclohexylhexyl alcohol were placed in a flask, and 45 g of phosphoric anhydride were gradually added to the flask over a period of 1 hour at 65°C to 70°C, while stirring. A maturation reaction was then carried out over a period of 3 hours at 65°C to 70°C. After cooling the reaction product to room temperature, 40 g of sodium hydroxide were gradually added to neutralize the product and obtain an organic phosphate ester B-4.

[0092] For “B-4”, the P-NMR integration contributions of P1 to P3 were 16%, 42%, and 42% respectively, when the sum of the integration contributions assigned to the organic phosphate ester P1 represented by formula (3) of the present application, the organic phosphate ester P2 represented by formula (4) of the present application, and the organic phosphate ester P3 represented by formula (5) of the present application was defined as 100%.

[0093] Compositions of the treatment agents for synthetic fibers according to the present invention (Examples 2, 4, 5, 6, 9, 11, 13 to 16) are shown in Table 1. Compositions of comparative examples (Comparative Examples 1 to 4) are shown in Table 2. [Table 1] Classification Cycloalkylalkanol derivative fraction type (mass %) Ionic surfactant Organic Other organic Phosphate esters Phosphate esters Proportion Proportion Type (mass %) Type (mass %) Non-ionic surfactant content type (mass %) Lubricant Content Type (Mass%) Example 1 A-1A-2A-9 424 B-1 1 E-1E-2E-3 522 N-1N-3N-5 1084 L-2L-3L-6 30208 2 A-3 1.5 B-3 0,5 E-1E-2E-3 523 N-1N-3N-4 15105 L-1L-3L-6 30208 3 A-2A-4 42 B-1 1 E-1E-2 44 N-1N-4N-5 1068 L-1L-3L-4 202615 4 A-5 0,3 B-2 0,5 E-1 5,5 N-1N-2N-4 141014,7 L-2L-3L-5 10405 5 A-6A-7 54 B-1 0,5 E-1E-4 10,5 N-4N-5N-6 142055 - - 6 A-6A-10 53 B-4 0,5 E-1 5,5 N-1N-3N-4 15104 L-2L-3L-4 17355 7 A-1A-2 63 B-1 1 E-2E-4 14 N-3N-8N-10 12125 L-2L-4L-7 163010 8 A-1A-10 53 B-3 1 E-1E-3 22 N-1N-5N-8 12107 L-1L-3L-7 20308 9 A-6A-8 54 B-2 0,5 E-3 1,5 N-4N-7N-9 144035 - - 10 A-1A-5 22 B-4 0,5 E-2E-3 23,5 N-2N-9N-10 15104 L-4L-5L-7 153511 11 A-5A-10 80,5 - - E-1 5,5 N-1N-3N-4 15108 L-2L-3 1340 12 A-1A-10 53 - - E-1E-3 23 N-1N-5N-8 12107 L-1L-3L-7 20308 13 A-8 15 B-4 0,5 E-1E-3 24 N-1N-2N-5 585,5 L-2L-4 2040 14 A-10 5 - - E-1E-4 11 N-5N-6N-7 101010 L-2 63 15 A-11 8 - - E-4E-2 73 N-1N-3N-5 7812 L-2L-4 2035 16 A-12 0,2 - - E-4E-2 73 N-2N-3N-10 710,87 L-3L-4 1055 [Table 2] Classification Cycloalkylalkanol derivative Ionic surfactant Non-ionic surfactant lubricant Organic phosphate ester Other organic phosphate esters type Percentage (mass%) type Percentage (mass%) type Percentage (mass%) type Percentage (mass%) type Percentage (mass%) Comparative example 1 - - - - E-1 1 N-1N-2N-3 16815 L-1L-2L-3 103020 2 - - - - E-2E-4 22 N-1N-2N-4 161010 L-4L-5L-6 401010 3 - - B-1 1 E-2E-4 14 N-3N-8N-10 12125 L-2L-4L-7 203510 4 - - - - - - N-1N-2N-3 151015 L-2L-3L-4 301020

[0094] In Tables 1 and 2, this means E-1: Sodium secondary alkyl (12 to 15 carbon atoms) sulfonate E-2: Potassium oleate E-3: Salt of oleyl alcohol EO2 phosphate ester and laurylamine EO2 E-4: Potassium lauryl phosphate ester N-1: Castor oil (hydrogenated)-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: Tetradecanol-EO15-PO15 N-9: Butanol-EO6-PO10 N-10: Glycerin-EO12 L-1: Mineral oil (47 mm 2 / s) L-2: Octyl palmitate L-3: Lauryl oleate L-4: Isotridecyl stearate L-5: Trimethylolpropane trilaurate L-6: Sorbitan monooleate L-7: Rapeseed oil Evaluation regarding emulsion stability

[0095] The synthetic fiber treatment agent and ion-exchanged water were mixed uniformly to produce a 15% emulsion. The emulsion was placed in a capped polyethylene bottle, sealed, and incubated for 7 days at 40°C. Afterward, the appearance was visually inspected, and the change in transmission was evaluated according to the following criteria. Transmission was measured using a spectrophotometer (UV / Visible Light Spectrophotometer U-1800, manufactured by Shimadzu) and evaluated according to the following criteria. The results are presented in Table 3. [Evaluation criteria regarding emulsion stability] A: The decrease in the transmission of the emulsion compared to the emulsion immediately after production was less than 5%. B: The decrease in the transmission of the emulsion compared to the emulsion immediately after production was at least 5% and less than 10%. C: The decrease in the transmission of the emulsion compared to the emulsion immediately after production was at least 10% and less than 20%. D: The decrease in transmission of the emulsion compared to the emulsion immediately after preparation was 20% or more, or the presence of particles or deposition was observed. Evaluation regarding handling properties at low temperatures

[0096] The synthetic fiber treatment agent was heated to 30°C and stirred thoroughly. 60 ml of the agent was placed in a 100 ml polyethylene bottle (inner diameter: 45 mm) fitted with a lid, and the container was sealed. The polyethylene bottle containing the synthetic fiber treatment agent was incubated for 3 days at a temperature of -5°C. After incubation, the appearance of the aqueous solution was visually inspected and evaluated according to the following criteria. Regarding the "fluidity" mentioned in the following criteria: The agent exhibited fluidity if the polyethylene bottle containing the synthetic fiber treatment agent was tilted sideways (90°) and if some of the aqueous solution flowed out of the container within 30 seconds. The results are shown in Table 3. [Evaluation criteria regarding handling properties at low temperatures] A: No clouding or turbidity was observed in the appearance, and the medium exhibited fluidity. B: The substance exhibited fluidity; cloudiness or turbidity was observed in its appearance, and the substance had partially solidified. C: The substance exhibited fluidity, cloudiness or turbidity was observed in its appearance, and the substance had largely solidified. D: The substance had completely solidified and showed no fluidity. Production of stretched thread

[0097] Polyethylene terephthalate with an intrinsic viscosity of 0.64 and a titanium oxide content of 0.2% was dried using a conventional method and spun at 295°C using an extruder. The spun product was then discharged through a die, cooled, and allowed to solidify to form a running filament. An aqueous solution of the synthetic fiber treatment agent, prepared to a concentration of 10%, was applied to the running filament using an oil-feeding method with a metering pump, such that the amount of aqueous solution applied as the synthetic fiber treatment agent was 1.0%.The running thread was then converged over a guide and drawn using a first galette at a surface speed of 1400 m / min and a surface temperature of 90°C, and a second galette at a surface speed of 4800 m / min and a surface temperature of 150°C. The drawn product was then wound at a speed of 4800 m / min to produce a drawn thread with 83 dtex and 36 filaments. Evaluation regarding generated electricity

[0098] The stretched thread obtained during the production of the drawn thread was wound again to produce a yarn spool containing approximately 200 g of thread. The yarn spool was placed in an atmosphere at 20°C and 40% relative humidity for 3 days; the electricity generated was measured and evaluated under the following conditions. (Conditions)

[0099] In an atmosphere of 20°C and 40% relative humidity, 20 yarn spools were placed on a spool stand. Threads were unwound and passed over a tensioning disc. The threads were then run in contact with three aluminum pins (2 cm diameter, 5 cm long). The pins were set so that the entry and exit angles were each 10 degrees, and the threads were wound at a speed of 200 m / min. At this point, the static electricity (generated electricity) of a path formed by the 20 running threads was measured at a position 20 cm from the third aluminum pin using a current-collecting potential measuring device.

[0100] The measured values ​​were evaluated according to the following criteria. The results are shown in Table 3. [Evaluation criteria regarding generated electricity] A: The generated voltage is less than 0.5 kV; the antistatic properties are excellent. B: The generated voltage is at least 0.5 kV and less than 2 kV; the antistatic property is good. C: The generated voltage is 2 kV or more; the antistatic properties are poor. [Table 3] Classification Emulsion stability Handling properties at low temperatures Electricity generated Example 1 A A A Example 2 A A A Example 3 A A A Example 4 A A A Example 5 A A A Example 6 A A A Example 7 A A A Example 8 A A A Example 9 A A A Example 10 A A A Example 11 A A B Example 12 A A B Example 13 B B A Example 14 B B B Example 15 B C B Example 16 C C B Comparative example 1 D D B Comparative example 2 D D B Comparative example 3 D D B Comparative example 4 D D C

[0101] The results shown in Table 3 indicate that the treatment agents for synthetic fibers according to Examples 2, 4, 5, 6, 9, 11, 13 to 16, which are specific examples of the present invention, have excellent properties with respect to emulsion stability and low-temperature handling, and that they are also excellent with respect to the antistatic property of the stretched thread. INDUSTRIAL APPLICABILITY

[0102] The treatment agent for synthetic fibers, the synthetic fiber to which the treatment agent for synthetic fibers adheres, and the method for treating a synthetic fiber according to the present invention have an effect such that static electricity and lint formation are prevented by excellent antistatic properties, in response to the increasing speed in recent years of the spinning step, the false twisting step, and the post-treatment step of synthetic fibers.

[0103] Furthermore, the treatment agent for synthetic fibers exhibits excellent properties in terms of emulsion stability and handling at low temperatures, in an environment at or below freezing, so that even when the treatment agent for synthetic fibers is stored in a low-temperature environment, the components contained therein do not separate and the treatment agent for synthetic fibers can adhere uniformly.

[0104] It follows from the above that the treatment agent for synthetic fibers according to the present invention is useful.< / cycloalkylalkanolderivat>

Claims

[1] Treatment agent for synthetic fibers, which has: one or more selected cycloalkylalkanol derivatives, represented by the following formulas (1) and (2): where the ring Q a a cycloalkylene group with 3 to 8 carbon atoms, R 1a a hydrogen atom or an alkyl group with 1 to 12 carbon atoms, R 2a a divalent hydrocarbon group with 1 to 12 carbon atoms, R 3 a hydrogen atom or a residue obtained by removing a hydroxyl group from a monocarboxylic acid with 6 to 22 carbon atoms, A 1a O is an alkylenoxy group with 2 to 4 carbon atoms, where only one type of alkylenoxy group can be used, or, if two or more alkylenoxy groups are present, two or more types of alkylenoxy groups can be used, and m aa whole number from 1 to 20, where the ring Q b , R 1b , R 2b , A 1b O and m b each independently have the same meaning as the ring Q a , R 1a , R 2a , A 1a O and m a in formula (1) and R 4 a residue obtained by removing two hydroxyl groups from a dicarboxylic acid with 4 to 12 carbon atoms. [2] Treatment agent for synthetic fibers according to claim 1, wherein the treatment agent for synthetic fibers comprises one or more selected cycloalkylalkanol derivatives represented by formula (1), wherein R 1a a hydrogen atom, or are represented by formula (2), where R 1b a hydrogen atom. [3] Treatment agent for synthetic fibers according to claim 1 or 2, wherein the treatment agent for synthetic fibers comprises one or more selected cycloalkylalkanol derivatives represented by formula (1), wherein R 2a a divalent hydrocarbon group with 2 to 8 carbon atoms, or are represented by formula (2), where R 2b a divalent hydrocarbon group with 2 to 8 carbon atoms. [4] Treatment agent for synthetic fibers according to any one of claims 1 to 3, wherein the treatment agent for synthetic fibers comprises one or more selected cycloalkylalkanol derivatives represented by formula (1), wherein R 3 a residue obtained by removing a hydroxyl group from an aliphatic monocarboxylic acid with 6 to 22 carbon atoms, or are represented by formula (2). [5] Treatment agent for synthetic fibers according to any one of claims 1 to 4, wherein the treatment agent for synthetic fibers contains the cycloalkylalkanol derivative in an amount of 0.01% to 30% by mass relative to the total mass of the treatment agent for synthetic fibers. [6] Treatment composition for synthetic fibers according to any one of claims 1 to 5, further comprising: a non-ionic surfactant other than the cycloalkylalkanol derivative and an ionic surfactant. [7] Treatment composition for synthetic fibers according to any one of claims 1 to 5, further comprising: a lubricant, a non-ionic surfactant other than the cycloalkylalkanol derivative and an ionic surfactant. [8] Treatment composition for synthetic fibers according to claim 6 or 7, wherein the ionic surfactant comprises at least one organic phosphate ester selected from an organic phosphate ester P1 represented by formula (3) below, an organic phosphate ester P2 represented by formula (4) below and an organic phosphate ester P3 represented by formula (5) below, where the ring Q b , R 1c , R 2c , A 1c O and m c each independently have the same meaning as the ring Q a , R 1a , R 2a , A 1a O and m a in formula (1), n is an integer from 2 to 4, R 5 a by removing an oxygen atom from the end chain of “R 1c -Ring Q c -R 2c -O-(A 1c O)m c -“ remaining is, where Q c , R 1c , R 2c , A1c O and m c each independently have the same meaning as the ring Q a , R 1a , R 2a , A 1a O and m a in formula (1), an alkali metal, an alkaline earth metal (1 / 2), an organic amine salt or a hydrogen atom, and M 1 an alkali metal, an alkaline earth metal (1 / 2), an organic amine salt or a hydrogen atom, where the ring Q d , R 1d , R 2a , A 1d O(OA 1d ) and m d each independently have the same meaning as the ring Q a , R 1a , R 2a , A 1a O and m a in formula (1) and M 2 an alkali metal, an alkaline earth metal (1 / 2), an organic amine salt or a hydrogen atom, where the ring Q e , R 1c , R 2e , A 1e O and m eeach independently have the same meaning as the ring Q a , R 1a , R 2a , A 1a O and m a in formula (1) and M 3 and M 4 each is independently an alkali metal, an alkaline earth metal (1 / 2), an organic amine salt or a hydrogen atom. [9] Synthetic fiber to which the treatment agent for synthetic fibers according to any one of claims 1 to 8 is adhered. [10] Method for treating a synthetic fiber which has: Adhesion of the treatment agent for synthetic fibers according to any one of claims 1 to 8 to a synthetic fiber in an amount of 0.1% to 5% by mass relative to the synthetic fiber.