TW202302957A - Treatment agent for synthetic fibers, synthetic fibers, and treatment method for synthetic fibers - Google Patents

Abstract

The present invention addresses the problem of providing: a treatment agent for synthetic fibers, the treatment agent imparting synthetic fibers with good antistatic properties, while exhibiting excellent emulsion stability and excellent handling properties at low temperatures; synthetic fibers to which this treatment agent is adhered; and a treatment method by which this treatment agent for synthetic fibers is adhered to synthetic fibers. The present invention provides, as a means for solving the problem, a treatment agent for synthetic fibers, the treatment agent being characterized by containing one or more substances that are selected from among cycloalkyl alkanol derivatives represented by general formula (1) or general formula (2).

Description

Treatment agent for synthetic fiber, synthetic fiber and method for treating synthetic fiber

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

In recent years, as the spinning steps, false twisting steps, and post-processing steps of synthetic fibers have become more and more high-speed, static electricity is more likely to occur, and the situation of producing yarn pilling is more likely to occur. In order to prevent such static electricity and pilling, it has been adopted: to increase the content of the functional enhancer that is attached to synthetic fibers as a treatment agent for synthetic fibers to prevent these situations, and to increase the treatment agent for synthetic fibers. The amount of adhesion of the agent to synthetic fibers was not sufficient, but even so, it was not enough, and it was desired to further improve the antistatic property.

On the other hand, synthetic fibers are produced in various countries and regions, and the conditions for the 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, although the processing agent for synthetic fibers containing a polyether (PO/EO copolymer) (for example, patent document 1 etc.) is well-known, the emulsion stability of these processing agents for synthetic fibers may be insufficient. If the emulsion stability of the treatment agent for synthetic fibers is poor, for example, the contained components will be separated during storage in the emulsion preparation tank. If it is made to adhere to the synthetic fibers, the treatment agent for synthetic fibers will not adhere uniformly, and it will become a problem in the subsequent spinning. The cause of many problems in the silk step, false twist step, and post-processing step. In addition, the low-temperature operability in an environment below the freezing point is reduced, which causes, for example, that the components of the treatment agent for synthetic fibers are solidified, resulting in a non-uniform state of the contained components, which cannot fully perform the function, or that it takes time to prepare and fill the emulsion. . That is, the improvement of the emulsion stability and low-temperature workability of the treatment agent for synthetic fibers is the key to improving the quality of synthetic fibers, and is an important issue. [Prior Art Literature] [Patent Document]

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

(Problem to be solved by the invention)

The object of the present invention is to provide: a treatment agent for synthetic fibers that imparts good destaticizing properties to synthetic fibers and is excellent in emulsion stability and low-temperature workability, and synthetic fibers to which the treatment agent is attached, that is, the treatment agent for synthetic fibers Treatment methods attached to synthetic fibers. (technical means to solve the problem)

In order to solve the above problems, the inventors of the present invention conducted in-depth studies and found that a cycloalkylalkane with a specific chemical structure can be used to impart a good antistatic property to synthetic fibers, and to produce a treatment agent for synthetic fibers that is excellent in emulsion stability and low-temperature operability. Alcohol derivatives have made great contributions to solve the above problems.

(式中， 環Q ^a：碳數3~8之環伸烷基 R ^1a：氫原子或碳數1~12之烷基 R ^2a：碳數1~12之二價烴基 R ³：氫原子、或從碳數6~22之單羧酸去除了羥基後的殘基 A ^1aO：碳數2~4之伸烷氧基(但，在該伸烷氧基存在2個以上的情況，可單獨為1種或2種以上) m ^a：0~100之整數) [化2]

(式中，環Q ^b、R ^1b、R ^2b、A ^1bO、m ^b係分別獨立地與式(1)的環Q ^a、R ^1a、R ^2a、A ^1aO、m ^a同義； R ⁴：從碳數4~12之二羧酸去除了2個羥基後的殘基)。 2.如1.所記載的合成纖維用處理劑，其中，含有從上述一般式(1)的R ^1a為氫原子之環烷基烷醇衍生物及上述一般式(2)的R ^1b為氫原子之環烷基烷醇衍生物中選擇之1種以上。 3.如1.或2.所記載的合成纖維用處理劑，其中，含有從上述一般式(1)的R ^2a為碳數2~8之二價烴基的環烷基烷醇衍生物及上述一般式(2)的R ^2b為碳數2~8之二價烴基的環烷基烷醇衍生物中選擇之1種以上。 4.如1.~3.中任一項所記載的合成纖維用處理劑，其中，含有從上述一般式(1)的R ³為由碳數6~22之脂肪族單羧酸除去了羥基後之殘基的環烷基烷醇衍生物及上述一般式(2)所示環烷基烷醇衍生物中選擇之1種以上。 5.如1.~4.中任一項所記載的合成纖維用處理劑，其中，相對於上述合成纖維用處理劑之總質量，上述環烷基烷醇衍生物係含有0.01~30質量%。 6.如1.~5.中任一項所記載的合成纖維用處理劑，其中，更進一步含有：非離子性界面活性劑(但，上述環烷基烷醇衍生物除外)及離子性界面活性劑。 7.如1.~5.中任一項所記載的合成纖維用處理劑，其中，更進一步含有：平滑劑、非離子性界面活性劑(但，上述環烷基烷醇衍生物除外)及離子性界面活性劑。 8.如6.或7.所記載的合成纖維用處理劑，其中，上述離子性界面活性劑係含有從下述一般式(3)所示有機磷酸酯P1、下述一般式(4)所示有機磷酸酯P2及下述一般式(5)所示有機磷酸酯P3中選擇至少1種有機磷酸酯； [化3]

(式中，環Q ^c、R ^1c、R ^2c、A ^1cO、m ^c係分別獨立地與一般式(1)的環Q ^a、R ^1a、R ^2a、A ^1aO、m ^a同義； n：2~4之整數 R ⁵：從「R ^1c-環Q ^c-R ^2c-O-(A ^1cO)m ^c-」去除了末端氧原子後的殘基(但，環Q ^c、R ^1c、R ^2c、A ^1cO、m ^c係分別獨立地與一般式(1)之環Q ^a、R ^1a、R ^2a、A ^1aO、m ^a同義)、鹼金屬、鹼土族金屬(1/2)、有機胺鹽或氫原子 M ¹：鹼金屬、鹼土族金屬(1/2)、有機胺鹽或氫原子) [化4]

(式中，環Q ^d、R ^1d、R ^2d、A ^1dO(OA ^1d)、m ^d係分別獨立地與一般式(1)的環Q ^a、R ^1a、R ^2a、A ^1aO、m ^a同義； M ²：鹼金屬、鹼土族金屬(1/2)、有機胺鹽或氫原子) [化5]

(式中，環Q ^e、R ^1e、R ^2e、A ^1eO、m ^e係分別獨立地與一般式(1)的環Q ^a、R ^1a、R ^2a、A ^1aO、m ^a同義； M ³、M ⁴：各自獨立為鹼金屬、鹼土族金屬(1/2)、有機胺鹽或氫原子)。 9.一種合成纖維，係附著了1.~8.中任一項所記載的合成纖維用處理劑。 10.一種合成纖維之處理方法，係使1.~8.中任一項所記載的合成纖維用處理劑，對合成纖維依成為0.1~5質量%附著。 (對照先前技術之功效) The specific gist of the present invention is as follows. 1. A treatment agent for synthetic fibers containing at least one selected from cycloalkyl alkanol derivatives represented by the following general formula (1) and general formula (2); [Chemical 1]

(wherein, ring Q ^a : a ring alkylene group with 3 to 8 carbons R ^1a : a hydrogen atom or an alkyl group with 1 to 12 carbons R ^2a : a divalent hydrocarbon group with 1 to 12 carbons R ³ : a hydrogen atom, Or the residue A after removing the hydroxyl group from a monocarboxylic acid with 6 to 22 carbons; ^1a O: an alkoxyl group with 2 to 4 carbons (however, if there are more than 2 alkoxyl groups, they can be independently 1 or more types) m ^a : an integer from 0 to 100) [Chemical 2]

(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 : A residue obtained by removing two hydroxyl groups from a dicarboxylic acid having 4 to 12 carbon atoms). 2. As described in 1., the processing agent for synthetic fibers, wherein R ^1a containing from the above-mentioned general formula (1) is a cycloalkyl alkanol derivative of a hydrogen atom and R ^1b of the above-mentioned general formula (2) is hydrogen One or more selected from cycloalkyl alkanol derivatives of atoms. 3. As 1. or 2. The processing agent for synthetic fibers as described, wherein, containing from the above-mentioned general formula (1) R ^2a is a cycloalkyl alkanol derivative of a divalent hydrocarbon group with a carbon number of 2 to 8 and the above-mentioned R ^2b of the general formula (2) is one or more selected from cycloalkyl alkanol derivatives of divalent hydrocarbon groups having 2 to 8 carbon atoms. 4. as described in any one of 1. to 3., the processing agent for synthetic fibers, wherein, containing from the above-mentioned general formula (1) R ³ is removed the hydroxyl group by the aliphatic monocarboxylic acid of carbon number 6～22 One or more selected from cycloalkyl alkanol derivatives and cycloalkyl alkanol derivatives represented by the above-mentioned general formula (2) of the following residue. 5. The treatment agent for synthetic fibers as described in any one of 1. to 4., wherein, relative to the total mass of the above-mentioned treatment agent for synthetic fibers, the cycloalkyl alkanol derivatives contain 0.01 to 30% by mass . 6. The treatment agent for synthetic fibers as described in any one of 1. to 5., wherein it further contains: a nonionic surfactant (except for the above-mentioned cycloalkyl alkanol derivatives) and an ionic surfactant active agent. 7. The treatment agent for synthetic fibers as described in any one of 1. to 5., wherein it further contains: a smoothing agent, a nonionic surfactant (except for the above-mentioned cycloalkyl alkanol derivatives) and Ionic surfactant. 8. As 6. or 7. The processing agent for synthetic fibers as described in 7., wherein, the above-mentioned ionic surfactant system contains organic phosphate ester P1 shown in the following general formula (3), the following general formula (4) Select at least one organic phosphate in the organophosphate P2 and the organophosphate P3 shown in the following general formula (5); [Chemical 3]

(In the formula, the rings Q ^c , R ^1c , R ^2c , A ^1c O, m ^c are independently synonymous with the rings Q ^a , R ^1a , R ^2a , A ^1a O, ^ma of the general formula (1); n : an integer of 2 to 4 R ⁵ : 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 the ring Q ^a , R ^1a , R ^2a , A ^1a O, ^ma synonymous with general formula (1), alkali metal, alkaline earth metal (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]

(wherein, ring Q ^d , R ^1d , R ^2d , A ^1d O(OA ^1d ), m ^d are independently combined with ring Q ^a , R ^1a , R ^2a , A ^1a O, m ^a is synonymous; M ² : alkali metal, alkaline earth metal (1/2), organic amine salt or hydrogen atom) [Chemical 5]

(wherein, rings Q ^e , R ^1e , R ^2e , A ^1e O, and ^me are independently synonymous with rings Q ^a , R ^1a , R ^2a , A ^1a O, and ^ma of general formula (1); M ^3. M ⁴ : each independently being an alkali metal, an alkaline earth metal (1/2), an organic amine salt or a hydrogen atom). 9. A synthetic fiber to which the treating agent for synthetic fiber according to any one of 1. to 8. is attached. 10. A method for treating synthetic fibers, which is to make the treatment agent for synthetic fibers described in any one of 1. to 8. adhere to synthetic fibers at a rate of 0.1 to 5% by mass. (compared to the effect of previous technology)

The treatment agent for synthetic fibers, synthetic fibers and synthetic fiber treatment method of the present invention can respond to the recent increase in speed in the spinning steps, false twisting steps, and post-processing steps of synthetic fibers, and utilize excellent antistatic properties. Can exert the effect of preventing 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 treatment agent for synthetic fibers of the present invention is excellent in low-temperature operation in an environment below freezing point, problems such as solidification of the components of the treatment agent for synthetic fibers do not occur, and it does not take time to prepare the filling of the emulsion.

The present invention relates to a treatment agent for synthetic fibers containing one or more cycloalkyl alkanol derivatives selected from the above general formula (1) and general formula (2), synthetic fibers to which the treatment agent is attached, and The processing method of making this processing agent for synthetic fibers adhere to synthetic fibers. Hereinafter, the present invention will be described in detail.

(式中， 環Q ^a：碳數3~8之環伸烷基 R ^1a：氫原子或碳數1~12之烷基 R ^2a：碳數1~12之二價烴基 R ³：氫原子、或從碳數6~22之單羧酸去除了羥基後的殘基 A ^1aO：碳數2~4之伸烷氧基(但，在該伸烷氧基存在2個以上的情況，可單獨為1種或2種以上) m ^a：0~100之整數) [化7]

(式中，環Q ^b、R ^1b、R ^2b、A ^1bO、m ^b係分別獨立與式(1)的環Q ^a、R ^1a、R ^2a、A ^1aO、m ^a同義、 R ⁴：從碳數4~12之二羧酸除去了羥基後的殘基) <Cycloalkyl alkanol derivatives> The synthetic fiber treatment agent of the present invention contains one or more cycloalkyl alkanol derivatives selected from the following general formula (1) and the following general formula (2) as a necessary ingredient. [chemical 6]

(wherein, ring Q ^a : a ring alkylene group with 3 to 8 carbons R ^1a : a hydrogen atom or an alkyl group with 1 to 12 carbons R ^2a : a divalent hydrocarbon group with 1 to 12 carbons R ³ : a hydrogen atom, Or the residue A after removing the hydroxyl group from a monocarboxylic acid with 6 to 22 carbons; ^1a O: an alkoxyl group with 2 to 4 carbons (however, if there are more than 2 alkoxyl groups, they can be independently 1 or more types) m ^a : an integer from 0 to 100) [Chem. 7]

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

The cycloalkyl alkanol derivatives shown in the above-mentioned general formula (1) of the present invention are monocarboxylic acid cycloalkyl alkanol esters with 6 to 22 carbon atoms, the alkylene oxide addition polymers of cycloalkyl alkanols, Or the ester of the alkylene oxide addition polymer of monocarboxylic acid with carbon number 6~22 and cycloalkyl alkanol, the cycloalkyl alkanol derivative shown in the above general formula (2) of the present invention is carbon number 4~12 Dicarboxylic acid cycloalkyl alkanol diesters, or diesters of alkylene oxide addition polymers of dicarboxylic acids with 4 to 12 carbon atoms and cycloalkyl alkanols. The ring Q ^a in the above general formula (1) and the ring Q ^b in the general formula (2) are preferably independently independent cycloalkyl groups with 5 to 8 carbon atoms, more preferably cycloalkyl groups with 5 or 6 carbon atoms . R ^1a in the above-mentioned general formula (1) and R ^1b in the general formula (2) are preferably independent hydrogen atoms or alkyl groups with 6 to 10 carbons, more preferably hydrogen atoms or alkane with 6 to 8 carbons The base and the best are hydrogen atoms. R ^2a in the above-mentioned general formula (1) and R ^2b in the general formula (2) are divalent hydrocarbon groups with 1 to 12 carbon atoms, which can be either independent linear or branched chains, or can be Either saturated or unsaturated. Among them, independent linear or branched alkylene groups with 1 to 12 carbon atoms are preferred, linear or branched alkylene groups with 2 to 8 carbon atoms are more preferred, and particularly preferred are A linear alkylene group with 2 to 8 carbon atoms. The hydrogen atom of R in the above-mentioned general formula ( ¹ ), or the monocarboxylic acid in the residue after removing the hydroxyl group from the monocarboxylic acid with 6 to 22 carbons, can be a saturated monocarboxylic acid or an unsaturated monocarboxylic acid either. Among them, a hydrogen atom or a residue obtained by removing a hydroxyl group from a saturated/unsaturated monocarboxylic acid with 8 to 20 carbon atoms is preferable, and a residue after removing a hydroxyl group from a saturated/unsaturated monocarboxylic acid with 8 to 20 carbon atoms is more preferable. residues after. In the above-mentioned general formula (2), the dicarboxylic acid in the residue after removing two hydroxyl groups from the dicarboxylic acid with carbon number 4 to 12 of ^R4 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 with 4 to 12 carbon atoms is preferred, and more preferably the residue obtained by removing two hydroxyl groups from a saturated aliphatic dicarboxylic acid with 4 to 12 carbon atoms. The residue after the 2 hydroxyl groups. When A ^1a O in the above-mentioned general formula (1) and A ^1b O in the general formula (2) are two or more kinds of alkyleneoxy groups with 2 to 4 carbons, each independently may be randomly dispersed or The block may be a mixture of these. Among them, one or two independent alkyleneoxy groups each having 2 or 3 carbon atoms are preferred. The ma in the above general formula (1) and m ^b in the general formula (2) represent the average molar number of alkoxyl groups with 2 to 4 carbons, preferably each independently being ^an integer of 0 to 20, It is more preferably an integer of 0-15.

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

The treatment agent for synthetic fibers of the present invention is relative to its total mass, and the cycloalkyl alkanol derivatives shown in the above general formula (1) and general formula (2) preferably contain 0.01 to 30% by mass, and more preferably contain 0.1 to 30% by mass. 25% by mass, preferably 0.2 to 20% by mass, more preferably 0.2 to 10% by mass. Furthermore, the treatment agent for synthetic fibers of the present invention preferably contains nonionic surfactants and ionic surfactants other than cycloalkyl alkanol derivatives represented by the above-mentioned general formula (1) and general formula (2). agent. Furthermore, the treatment agent for synthetic fibers of the present invention preferably contains nonionic surfactants, smoothing agents and ionic surfactants other than cycloalkyl alkanol derivatives represented by the above general formula (1) and general formula (2). Surfactant. Nonionic surfactants, smoothing agents, and ionic interface agents other than cycloalkyl alkanol derivatives represented by the above general formula (1) and general formula (2) can be used in combination with the synthetic fiber treatment agent of the present invention. Active agents are described.

<Nonionic surfactants other than cycloalkyl alkanol derivatives> The treatment agent for synthetic fibers of the present invention can be used in combination with nonionic surfactants other than the cycloalkyl alkanol derivatives shown in the above-mentioned general formula (1) and general formula (2). 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, polyoxyethylene butyl oil 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 amino ether, polyoxyethylene lauryl amide ether, etc., added carbon number 2~4 to organic acid, organic alcohol, organic amine and/or organic amide molecule (2) polyoxyalkylene sorbitan trioleate, polyoxyalkylene castor oil ether, polyoxyalkylene hardened castor oil ether, polyoxyalkylene hardened castor oil Polyoxyalkylene polyol fatty acid esters such as sesame oil ether trioleate; (3) alkylamides such as diethanolamine monolauric amide; (4) polyoxyethylene diethanolamine monooleylamide and other polyoxyalkylene Alkyl fatty acid amides, etc. These nonionic surfactants may be used alone or in combination of two or more. In the present invention, those with EO and PO at the end of the compound name refer to the adducts of ethylene oxide and propylene oxide, respectively, and the following numbers represent the added moles. The numerical values described after EO and PO refer to the average added moles of each.

<Smoothing agents other than cycloalkyl alkanol derivatives> The treatment agent for synthetic fibers of the present invention can be used in combination with smoothing agents other than cycloalkyl alkanol derivatives represented by the above general formula (1) and general formula (2), such as: (1) butyl stearate Aliphatic monoalcohols and fats such as esters, octyl stearate, oleyl laurate, oleyl oleate, isopentadecyl isostearate, octyl palmitate, isotridecyl stearate, lauryl caprylate, etc. (2) 1,6-Hexanediol Dicaprate, Trimethylolpropane Monooleate Monolaurate, Sorbitan Trioleate, Sorbitan Monooleate, sorbitan tristearate, sorbitan distearate, sorbitan monostearate, glycerol monolaurate and other aliphatic polyalcohols and aliphatic monocarboxylic (3) Dilauryl adipate, dioleyl azelate, diisocetyl thiodipropionate, dipolyoxyethylene lauryl adipate and other aliphatic monoalcohols and fats (4) ester compounds of aromatic monoalcohol and aliphatic monocarboxylic acid such as benzyl oleate, benzyl laurate and polyoxypropylene benzyl stearate; (5) bis Esters of aromatic polyols and aliphatic monocarboxylic acids such as phenol A dilaurate and polyoxyethylene bisphenol A dilaurate; (6) bis(2-ethylhexyl phthalate), isophthalic acid Ester compounds of diisostearyl, trioctyl trimellitate and other aliphatic monoalcohols and aromatic polycarboxylic acids; (7) Coconut oil, rapeseed oil, sunflower oil, soybean oil, castor oil, sesame oil, fish oil and natural oils such as tallow; (8) known smoothing agents used in synthetic fiber treatment agents such as mineral oil. These smoothing agent components may be used individually by 1 type, and may use it in combination of 2 or more types.

(式中，環Q ^c、R ^1c、R ^2c、A ^1cO、m ^c係分別獨立地與一般式(1)的環Q ^a、R ^1a、R ^2a、A ^1aO、m ^a同義； n：2~4之整數 R ⁵： 從「R ^1c-環Q ^c-R ^2c-O-(A ^1cO)m ^c-」去除了末端氧原子後的殘基(但，環Q ^c、R ^1c、R ^2c、A ^1cO、m ^c係分別獨立地與一般式(1)之環Q ^a、R ^1a、R ^2a、A ^1aO、m ^a同義)、鹼金屬、鹼土族金屬(1/2)、有機胺鹽或氫原子 M ¹：鹼金屬、鹼土族金屬(1/2)、有機胺鹽或氫原子) [化9]

(式中，環Q ^d、R ^1d、R ^2d、A ^1dO(OA ^1d)、m ^d係分別獨立地與一般式(1)的環Q ^a、R ^1a、R ^2a、A ^1aO、m ^a同義； M ²：鹼金屬、鹼土族金屬(1/2)、有機胺鹽或氫原子) [化10]

(式中，環Q ^e、R ^1e、R ^2e、A ^1eO、m ^e係分別獨立地與一般式(1)的環Q ^a、R ^1a、R ^2a、A ^1aO、m ^a同義； M ³、M ⁴：各自獨立的鹼金屬、鹼土族金屬(1/2)、有機胺鹽或氫原子)。 <Ionic surfactant> The treatment agent for synthetic fibers of the present invention is preferably used in combination with organic phosphate ester P1 represented by the following general formula (3), organic phosphate ester P2 represented by the following general formula (4) and the following Among the organophosphates P3 represented by the general formula (5), at least one organophosphate is selected as the ionic surfactant. [chemical 8]

(In the formula, the rings Q ^c , R ^1c , R ^2c , A ^1c O, m ^c are independently synonymous with the rings Q ^a , R ^1a , R ^2a , A ^1a O, ^ma of the general formula (1); n : an integer of 2 to 4 R ⁵ : 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 the ring Q ^a , R ^1a , R ^2a , A ^1a O, ^ma synonymous with general formula (1), alkali metal, alkaline earth metal (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]

(wherein, ring Q ^d , R ^1d , R ^2d , A ^1d O(OA ^1d ), m ^d are independently combined with ring Q ^a , R ^1a , R ^2a , A ^1a O, m ^a is synonymous; M ² : alkali metal, alkaline earth metal (1/2), organic amine salt or hydrogen atom) [Chemical 10]

(wherein, rings Q ^e , R ^1e , R ^2e , A ^1e O, and ^me are independently synonymous with rings Q ^a , R ^1a , R ^2a , A ^1a O, and ^ma of 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).

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 , A ^1d O(OA ^1d ) in the above general formula (4) , m ^d , the rings Q ^e , R ^1e , R ^2e , A ^1e O, and ^me in the general formula (5) above are preferably independently combined with the rings Q ^a , R ^1a , R ^2a , A ^1a O, and ma ^are the same. R ⁵ in the above general formula (3) is preferably a 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 independently synonymous with ring Q ^a , R ^1a , R ^2a , A ^1a O, and ^ma of general formula (1), respectively). M ¹ in the above general formula (3), M ² in the above general formula (4), M ³ and M ⁴ in the above general formula (5) are preferably independent alkali metal or organic amine salts.

The sum of the P core NMR integral ratios attributable to the organophosphate P1 represented by the above general formula (3), the organophosphate P2 represented by the above general formula (4), and the organophosphate 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 30-80%, more preferably 35-75%, and most preferably 40-70%.

P-nucleus NMR integral ratio (P-nucleus NMR integral ratio (%) attributable to organophosphates P1, P2, and P3) refers to the addition of excess KOH to alkali metal salts of organophosphates, etc., so that the pH is 12 or higher Under the conditions, values calculated from the following formulas (a) to (c) were used using measured values when supplied to ³¹ P-NMR (VALIAN company trade name MERCURY plus NMR Spectrometer System, 300 MHz). In addition, as the solvent system, a mixed solvent of heavy water/tetrahydrofuran=8/2 (volume ratio) can be used. In addition, in the formulas (a) to (c), "P 1" means the P core NMR integral value belonging to the organophosphate P1 shown in the general formula (3), and "P 2" means the P core NMR value belonging to the general The P core NMR integral value of the organophosphate P2 shown in formula (4), "P3" means the P core NMR integral value of all organophosphate P3 belonging to the general formula (5).

[number 1] P core NMR integral ratio of organophosphate P1 (%)=(P 1)÷(P 1+P 2+P 3)×100・・・(a) [number 2] P core NMR integral ratio of organophosphate P2 (%)=(P 2)÷(P 1+P 2+P 3)×100・・・(b) [number 3] P core NMR integral ratio of organophosphate P3 (%)=(P3)÷(P1+P2+P3)×100・・・(c) The manufacturing method of organic phosphate shown in the above-mentioned general formula (3)～(5) of the present invention is not particularly limited, for example: cycloalkyl alkanol, or on cycloalkyl alkanol according to random, block or These mixing methods add and polymerize alkylene oxides with 2 to 4 carbon atoms, mix and esterify them with phosphorylating agents represented by anhydrous phosphoric acid, or further neutralize them with alkali. maker.

型兩性界面活性劑；N,N-雙(2-羧乙基)-辛胺鈉等丙胺酸型兩性界面活性劑等。該等成分係可單獨使用1種、亦可組合使用2種以上。 <Other ionic surfactants> The synthetic fiber treatment agent of the present invention may further contain other ionic surfactants, for example, known anionic surfactants and cationic surfactants used as fiber treatment agents. active agent, amphoteric surfactant, etc. Specifically, the anionic surfactant system can include, for example: (1) carboxylic acid soap-type ionic surfactants such as potassium acetate, octanoic acid potassium salt, oleic acid potassium salt, oleic acid sodium salt, alkenyl succinic acid potassium salt, etc. (2) Secondary alkane sulfonic acid sodium salt, dodecylbenzene sulfonic acid sodium salt, dioctyl sulfosuccinic acid sodium salt and other sulfonate-type ionic surfactants; (3) Polyoxyethylene lauryl Sulfate ester sodium salt, cetyl sulfate potassium salt, tallow vulcanized oil, castor oil vulcanized oil and other sulfate ester ionic surfactants; Hexaalkyl ester potassium salt, octadecyl phosphate potassium salt, oleyl phosphate triethanolamine salt, polyoxyethylene oleyl ether phosphate and polyoxyethylene lauryl amine ether salts and other organic phosphate salts. Also, the cationic surfactant system can be exemplified: quaternary ammonium salts such as tetrabutylammonium salt, etc., and the amphoteric surfactant system can be exemplified: organic amine oxides such as dimethyl stearyl amine oxide; dimethyl ammonium acetic acid beet

Type amphoteric surfactants; N, N-bis(2-carboxyethyl)-octylamine sodium and other alanine type amphoteric surfactants, etc. These components may be used alone or in combination of two or more.

In the treatment agent for synthetic fibers of the present invention, when containing the cycloalkyl alkanol derivatives represented by the above general formula (1) and the above general formula (2), and other nonionic surfactants and ionic surfactants In the case of the active agent, with respect to the total mass of the treatment agent for synthetic fibers, the other nonionic surfactants are preferably contained in an amount of 50 to 99% by mass, more preferably 60 to 99% by mass, and most preferably 65% by mass. ~99% by mass, and other ionic surfactants are preferably 0.01-10% by mass, more preferably 0.1-10% by mass, and most preferably 0.5-5% by mass. When the above-mentioned ionic surfactant is contained from the organic phosphate ester P1 shown in the above general formula (3), the organic phosphate ester P2 shown in the above general formula (4) and the organic phosphate ester P3 shown in the above general formula (5) In the case of selecting at least one organic phosphate, the total amount of the organic phosphate shown in the above general formulas (3)~(5) is relative to the total mass of the synthetic fiber treatment agent, preferably containing 0.01~10% by mass, more preferably Contains 0.05~5% by mass of the series, and 0.1~3% by mass of the special series.

In the treatment agent for synthetic fibers of the present invention, when containing the cycloalkyl alkanol derivatives represented by the above general formula (1) and the above general formula (2), and the nonionic interface other than the above cycloalkyl alkanol derivatives In the case of active agents, smoothing agents, and ionic surfactants, the other nonionic surfactants are preferably contained in an amount of 5 to 60% by mass, more preferably contained in an amount of 10 to 60% by mass, and particularly preferably contained in an amount of 10 to 60% by mass. 50% by mass; other smoothing agents preferably contain 30-80% by mass, more preferably 30-70% by mass, and most preferably 40-70% by mass; other ionic surfactants It is preferably 0.1 to 25% by mass, more preferably 0.5 to 20% by mass, and most preferably 1.0 to 15% by mass. When the above-mentioned ionic surfactant system contains organic phosphate ester P1 shown in the above-mentioned general formula (3), organic phosphate ester P2 shown in the above-mentioned general formula (4), and organic phosphate ester P3 shown in the above-mentioned general formula (5) When selecting at least one organic phosphate, the total amount of the organic phosphate shown in the general formulas (3) to (5) is relative to the total mass of the treatment agent for synthetic fibers, preferably containing 0.01 to 10% by mass, The more preferred type contains 0.05 to 5% by mass, and the particularly preferred type contains 0.1 to 3% by mass. The synthetic fiber treating agent of this composition is quite suitable as a synthetic fiber treating agent in the spinning-drawing step.

＜Other ingredients＞ The treatment agent for synthetic fibers of the present invention is within the scope of not hindering the effect of the present invention, and it can also be further blended with stabilizers, antistatic agents, and defoamers (polysiloxane compounds, minerals, etc.) for maintaining the quality of the treatment agent. Oil, etc.), adhesives, antioxidants, UV absorbers, etc. are commonly used ingredients for synthetic fiber treatments.

＜Synthetic Fiber＞ The synthetic fiber of this invention is the synthetic fiber to which the processing agent for synthetic fibers of this invention adhered. The synthetic fibers to which the treating agent for synthetic fibers of the present invention is attached are not particularly limited, and examples thereof include: (1) polyesters such as polyethylene terephthalate, polytrimethylene terephthalate, and polylactate; (2) polyamide fibers such as nylon 6 and nylon 66; (3) polyacrylic fibers such as polyacrylic acid and modified polyacrylonitrile; (4) polyolefin fibers such as polyethylene and polypropylene; and Polyurethane fibers, etc. Among them, the effect is higher when it adheres to polyester-based fibers and polyamide-based fibers. The ratio of the synthetic fiber treatment agent of the present invention attached to the synthetic fiber is not particularly limited, and the synthetic fiber treatment agent of the present invention is preferably attached at a ratio of 0.1 to 3% by mass, more preferably at a ratio of 0.1 to 3% by mass. 0.3~1.2% by mass is attached. With this configuration, the effects of the present invention can be further enhanced. Furthermore, the step of attaching the treating agent for synthetic fibers of the present invention is not particularly limited, and examples thereof include a spinning step, a step of simultaneously performing spinning and stretching, and the like. In addition, the method of making the treatment agent of the present invention adhere to synthetic fibers includes, for example, a drum oiling method, a diversion oiling method using a metering pump, an immersion oiling method, and a spray oiling method. In addition, the form of the treatment agent of the present invention when attached to synthetic fibers includes, for example, a single agent, an organic solvent solution, an aqueous liquid, etc., and is preferably an aqueous liquid. When the aqueous solution of the treatment agent of the present invention is attached, the treatment agent of the present invention may preferably be attached in an amount of 0.1 to 3% by mass, more preferably in an amount of 0.3 to 1.2% by mass, with respect to synthetic fibers.

The treatment agent for synthetic fibers of the present invention contains cycloalkyl alkanol derivatives represented by the above general formula (1) and the above general formula (2) as essential components, and can be used in the spinning step, false twisting step, As well as in the post-processing steps, it can respond to the high speed in recent years, and can exert the effect of preventing static electricity and pilling. Furthermore, the treatment agent for synthetic fibers of the present invention has excellent emulsion stability, so even if it is stored for a long time, the containing components will not be separated, and because it has excellent low-temperature operability in an environment below freezing point, it will not cause the formation of a synthetic fiber treatment agent. Since there are problems such as coagulation of the components of the treatment agent, the treatment agent for synthetic fibers can be evenly attached, and it can fully function, and it does not need to be time-consuming for filling when preparing the emulsion. [Example]

Hereinafter, examples are given to illustrate the present invention, but the technical scope of the present invention is not limited thereto. In addition, in the following examples and comparative examples, "part" means "mass part", and "%" means "mass %".

<Synthesis of cycloalkyl alkanol derivatives> (A-1) Fill the reaction vessel with: 184g of 6-cyclohexylhexanol and 282g of oleic acid, melt at 75°C under nitrogen, then add the catalyst 0.6 g of p-toluenesulfonic acid was reacted at 120° C. under a reduced pressure of 2 mmHg for 4 hours while discharging the produced water to the outside of the reaction system. Next, in the presence of nitrogen, return to normal pressure at 105°C, add an adsorbent to treat the catalyst, and perform filtration at 90°C to obtain A-1. The "A-1" is a cycloalkyl alkane in which the 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 ma ^is 0. Alcohol compounds. In addition, the purity of "A-1" was measured by 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-mentioned production method of "A-1", A-2 was obtained in the same manner except that 198 g of 7-cyclohexylheptanol was used instead of 6-cyclohexylhexanol. The "A-2" is a cycloalkyl group in which the ring ^{Q a} in the general formula (1) is a cyclohexylene group, R ^1a is a hydrogen atom, R ^2a is a heptyl group, R ³ is an oleyl group, and ma ^is 0 alkanol compounds. In addition, the purity of "A-2" was determined to be 98% by GC-MS measurement based on the cycloalkyl alkanol derivative of the present invention.

(A-3) 198 g of 7-cyclohexylheptanol was charged in an autoclave, and after adding 0.3 g of potassium hydroxide as a catalyst, the interior of the autoclave was fully replaced with nitrogen. While stirring, maintain the gauge pressure of 0.0~0.4MPa and the reaction temperature of 110~120°C, and inject 132g of ethylene oxide to carry out the addition polymerization reaction for about 5 hours. Then, the obtained reactant was transferred into a flask, and the potassium hydroxide of the catalyst was neutralized with phosphoric acid. The generated potassium phosphate was neutralized by filtration to obtain an ethylene oxide addition polymer of 7-cyclohexylheptanol. 165 g of the obtained addition polymer and 141 g of oleic acid were melted at 75° C. in the presence of nitrogen, and then 0.3 g of p-toluenesulfonic acid as a catalyst was added. The water was discharged out of the reaction system, and the reaction was carried out for 4 hours. Next, in the presence of nitrogen, the pressure was returned to normal pressure at 105° C., the catalyst was treated by adding an adsorbent, and filtration was performed at 90° C. to obtain A-3. The "A-3" is the ring Q ^a in the general formula (1) is a cyclohexylene group, R ^1a is a hydrogen atom, R ^2a is a heptyl group, R ³ is an oleyl group, A ^1a O is EO (ethylene Oxygen group), the cycloalkyl alkanol derivative compound whose ^ma is 3. In addition, the purity of "A-3" was determined to be 97% by GC-MS measurement based on the cycloalkyl alkanol derivative of the present invention.

(A-4) In the production method of "A-3" above, instead of 7-cyclohexylheptanol, 184g of 6-cyclohexylheptanol is used instead of 132g of ethylene oxide, and 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. The "A-4" is the 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 octyl group, and A ^1a O is EO (ethoxyl group) Cycloalkyl alkanol derivative compound with 6 moles, 2 moles of PO (propoxyl) and ^ma of 8. In addition, the purity of "A-4" was determined to be 95% by GC-MS measurement based on the cycloalkyl alkanol derivative of the present invention.

(A-5) 184 g of 6-cyclohexylhexanol was charged in an autoclave, and after adding 0.3 g of potassium hydroxide as a catalyst, the interior of the autoclave was fully replaced with nitrogen. While stirring, 88 g of ethylene oxide and 116 g of propylene oxide were pressed in at a gauge pressure of 0.0-0.4 MPa and a reaction temperature of 110-120°C, and the addition polymerization reaction was carried out for about 5 hours. Then, the obtained reactant was transferred into a flask, and the potassium hydroxide of the catalyst was neutralized with phosphoric acid. The resulting potassium phosphate was neutralized by filtration to obtain an addition polymer of ethylene oxide and propylene oxide of 7-cyclohexylheptanol. 194 g of the obtained addition polymer and 37 g of adipic acid were melted at 75° C. in the presence of nitrogen, and then 0.3 g of p-toluenesulfonic acid as a catalyst was added. The generated water was discharged out of the reaction system, and the reaction was performed for 4 hours. Next, in the presence of nitrogen, return to normal pressure at 105°C, add an adsorbent to treat the catalyst, and perform filtration at 90°C to obtain A-5. The "A-5" is the ring Q ^b in the general formula (2) is a cyclohexylene group, R ^1b is a hydrogen atom, R ^2b is a hexylene group, R ⁴ is an adipyl group, A ^1b O is EO (ethylene Cycloalkyl alkanol derivative compound with 2 moles of oxy) and 2 moles of PO(propoxyl) and m ^b of 4. In addition, the purity of "A-5" was determined to be 96% by GC-MS measurement based on the cycloalkyl alkanol derivative of the present invention.

(A-6) Except in the production method of "A-3" above, 128 g of 2-cyclohexyl ethanol was used instead of 7-cyclohexyl heptanol, and 142 g of stearic acid was used instead of 141 g of oleic acid Except for the rest, A-6 was obtained in the same manner. The "A-6" refers to the general formula (1) in which the ring Q ^a 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 EO (extension group). Ethoxy), ^ma cycloalkyl alkanol derivative compound of 3. In addition, the purity of "A-6" was determined to be 97% by GC-MS measurement based on the cycloalkyl alkanol derivative of the present invention.

(A-7) Fill 128g of 2-cyclohexyl ethanol in the autoclave, add 0.3g of potassium hydroxide as a catalyst, and fully replace the interior of the autoclave with nitrogen. While stirring, 352 g of ethylene oxide and 116 g of propylene oxide were injected while maintaining a gauge pressure of 0.0-0.4 MPa and a reaction temperature of 110-120° C., and the addition polymerization reaction was carried out for about 5 hours. Then, the obtained reactant was transferred into a flask, and the potassium hydroxide of the catalyst was neutralized with phosphoric acid. The resulting potassium phosphate was neutralized by filtration to obtain ethylene oxide and propylene oxide addition polymer A-7 of 2-cyclohexylethanol. The "A-7" is the 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, A ^1a O is EO (ethoxy Cycloalkyl alkanol derivative compound with 8 moles of base) and 2 moles of PO (propoxyl) and ^ma of 10. In addition, the purity of "A-7" was determined to be 100% by GC-MS measurement based on the cycloalkyl alkanol derivative of the present invention.

(A-8) Except that in the production method of "A-7" above, 198 g of 7-cyclohexylheptanol was used instead of 2-cyclohexyl ethanol, and 352 g of ethylene oxide and 116 g of propylene oxide were replaced, A-8 was obtained in the same manner except for using 264 g of ethylene oxide and 116 g of propylene oxide. The "A-8" is the ring ^Q a in the general formula (1) is a cyclohexylene group, R ^1a is a hydrogen atom, R ^2a is a heptyl group, R ³ is a hydrogen atom, A ^1a O is EO (ethoxy Cycloalkylalkanol derivative compound with 6 moles of base) and 2 moles of PO (propoxyl) and ^ma of 8. In addition, the purity of "A-8" was determined to be 100% by GC-MS measurement based on the cycloalkyl alkanol derivative of the present invention.

(A-9) Except in the production method of "A-7" above, 184 g of 6-cyclohexyl hexanol was used instead of 2-cyclohexyl ethanol, and 638 g of propylene oxide was used instead of 116 g of propylene oxide Other than that, the rest were obtained A-9 in the same manner. The "A-9" is the ring ^Q a in the general formula (1) is a cyclohexyl group, R ^1a is a hydrogen atom, R ^2a is a hexyl group, R ³ is a hydrogen atom, A ^1a O is EO (ethoxyl group) ) 8 moles, PO (propoxyl) 11 moles, ^ma cycloalkyl alkanol derivative compound of 19. In addition, the purity of "A-9" was determined to be 100% by GC-MS measurement based on the cycloalkyl alkanol derivative of the present invention.

(A-10) Except that in the production method of "A-7" above, 184 g of 6-cyclohexyl hexanol was used instead of 2-cyclohexyl ethanol, and 352 g of ethylene oxide and 116 g of propylene oxide were replaced. A-10 was obtained in the same manner except that 348 g of propylene oxide was used. The "A-10" is the 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 a hydrogen atom, A ^1a O is PO (propoxyl ) 6 moles, ^ma cycloalkyl alkanol derivative compound of 6. In addition, the purity of "A-10" was determined to be 100% by GC-MS measurement based on the cycloalkyl alkanol derivative of the present invention.

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

(A-12) Except in the production method of "A-7" above, instead of 2-cyclohexyl ethanol, use 72g of cyclopropylmethanol, and instead of 352g of ethylene oxide and 116g of propylene oxide, use Except for 440 g of ethylene oxide, A-12 was obtained in the same manner. This "A-12" is the ring ^Q a in the general formula (1) is a cyclopropyl group, R ^1a is a hydrogen atom, R ^2a is a methylene group, R ³ is a hydrogen atom, A ^1a O is EO (ethylene Oxygen) 10 moles, ^ma cycloalkyl alkanol derivative compound of 10. In addition, the purity of "A-12" was determined to be 100% by GC-MS measurement based on the cycloalkyl alkanol derivative of the present invention.

＜Synthesis of Organic Phosphates＞ (B-1) 184 g of 6-cyclohexylhexanol was charged in an autoclave, and after adding 0.3 g of potassium hydroxide as a catalyst, the interior of the autoclave was fully replaced with nitrogen. While stirring, 220 g of ethylene oxide was injected while maintaining a gauge pressure of 0.0-0.4 MPa and a reaction temperature of 110-120° C., and the addition polymerization reaction was carried out for about 5 hours. Then, the obtained reactant was transferred into a flask, and the potassium hydroxide of the catalyst was neutralized with phosphoric acid. The resulting potassium phosphate was neutralized by filtration to obtain an ethylene oxide addition polymer of 6-cyclohexylhexanol. 202 g of the obtained polymer was filled in a flask, kept at 65-70°C, and 24 g of anhydrous phosphoric acid was gradually added in small amounts over 1 hour while stirring, and the aging reaction was carried out at 65-70°C for 3 hours. After cooling to room temperature, 28 g of potassium hydroxide was gradually added for neutralization, and organic phosphate B-1 was obtained. The "B-1" will belong to the organophosphate P1 represented by the general formula (3) of this case, the organophosphate P2 represented by the general formula (4) of this case, and the P3 represented by the general formula (5) of this case. When the total nuclear NMR integral ratio was set to 100%, the P nuclear NMR integral ratios of P1~P3 were 0%, 48%, and 52%, respectively.

(B-2) Fill 128 g of 2-cyclohexyl ethanol in the autoclave, add 0.3 g of potassium hydroxide as a catalyst, and fully replace the interior of the autoclave with nitrogen. While stirring, maintain a gauge pressure of 0.0-0.4 MPa and a reaction temperature of 110-120°C to press-in 174 g of propylene oxide, and perform addition polymerization for about 5 hours. Then, the obtained reactant was transferred into a flask, and the potassium hydroxide of the catalyst was neutralized with phosphoric acid. The generated potassium phosphate was neutralized by filtration to obtain a propylene oxide addition polymer of 2-cyclohexylethanol. 151 g of the obtained polymer was filled in a flask, kept at 65-70°C, and 22 g of anhydrous phosphoric acid was gradually added in small amounts over 1 hour while stirring, and the aging reaction was carried out at 65-70°C for 3 hours. After cooling to room temperature, 87 g of dibutylethanolamine was gradually added for neutralization, and organic phosphate B-2 was obtained. The "B-2" will be attributed to the organophosphate P1 represented by the general formula (3) of this case, the organophosphate P2 represented by the general formula (4) of this case, and the P3 represented by the general formula (5) of this case. When the total nuclear NMR integral ratio was set to 100%, the P nuclear NMR integral ratios of P1~P3 were 12%, 43%, and 45%, respectively.

(B-3) Fill 198 g of 7-cyclohexylheptanol in the autoclave, add 0.3 g of potassium hydroxide as a catalyst, and fully replace the interior of the autoclave with nitrogen. While stirring, 264 g of ethylene oxide and 116 g of propylene oxide were press-injected at a gauge pressure of 0.0-0.4 MPa and a reaction temperature of 110-120° C., and the addition polymerization reaction was carried out for about 5 hours. Then, the obtained reactant was transferred into a flask, and the potassium hydroxide of the catalyst was neutralized with phosphoric acid. The generated potassium phosphate was neutralized by filtration to obtain an addition polymer of ethylene oxide and propylene oxide of 7-cyclohexylheptanol. 289g of the obtained polymer was filled in a flask, kept at 65-70°C, and 23g of anhydrous phosphoric acid was gradually added in small amounts over 1 hour while stirring, and the aging reaction was carried out at 65-70°C for 3 hours. After cooling to room temperature, 28 g of potassium hydroxide was gradually added for neutralization, and organic phosphate B-3 was obtained. The "B-3" is the P that will belong to the organophosphate P1 shown in the general formula (3) of this case, the organophosphate P2 shown in the general formula (4) of this case, and the organophosphate P3 shown in the general formula (5) of this case. When the total nuclear NMR integral ratio was set to 100%, the P nuclear NMR integral ratios of P1~P3 were 5%, 47%, and 48%, respectively.

(B-4) Fill 184g of 6-cyclohexylhexanol in a flask, keep it at 65~70°C, add 45g of anhydrous phosphoric acid in small amounts for 1 hour while stirring, then carry out the aging reaction at 65~70°C for 3 hours. After cooling to room temperature, 40 g of potassium hydroxide was gradually added for neutralization, and organic phosphate B-4 was obtained. The "B-4" will be attributed to the organophosphate P1 represented by the general formula (3) of this case, the organophosphate P2 represented by the general formula (4) of this case, and the P3 represented by the general formula (5) of this case. When the total nuclear NMR integral ratio was set to 100%, the P nuclear NMR integral ratios of P1~P3 were 16%, 42%, and 42%, respectively.

The composition system of the treating agent for synthetic fiber of the present invention (embodiment 1～16) is as shown in Table 1, and the composition system of comparative examples (Comparative Examples 1～4) is as shown in Table 2.

[Table 1] distinguish Cycloalkyl alkanol derivatives Ionic Surfactant nonionic surfactant smoothing agent organophosphate Other ionic surfactants type Ratio (mass%) type Ratio (mass%) type Ratio (mass%) type Ratio (mass%) type 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 type Ratio (mass%) type Ratio (mass%) type Ratio (mass%) type Ratio (mass%) type 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: Oleyl alcohol EO2 phosphate and laurylamine EO2 Salt E-4: Potassium Laureth Phosphate N-1: Hardened Castor Oil EO12 Trioleate N-2: Tridecyl Alcohol EO3・PO2 Palmitate N-3: Oleic Acid EO5 N-4 : Nonyl alcohol 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: Isotridecane stearate Alkyl ester L-5: trimethylolpropane trilaurate (laurate) L-6: sorbitan monooleate L-7: rapeseed oil

・Emulsion stability evaluation Mix the treatment agent for synthetic fibers with ion-exchanged water evenly to prepare a treatment agent emulsion for synthetic fibers with a concentration of 15%, put it into a polyethylene bottle with a cover and seal it tightly, and place the treatment agent emulsion for synthetic fibers at 40°C. After standing for 7 days, the appearance was visually observed, and the change in transmittance was evaluated according to the following criteria. The transmittance was measured using a spectrophotometer (ultraviolet-visible spectrophotometer U-1800 manufactured by Shimadzu Corporation), and evaluated in accordance with the following criteria. The results are organized as shown in Table 3. [emulsion stability evaluation criteria] ◎◎: The penetration rate of the emulsion immediately after preparation decreased by less than 5% ◎: The penetration rate of the emulsion immediately after preparation is reduced by more than 5% and less than 10% ○: The penetration rate of the emulsion immediately after preparation has decreased by more than 10% and less than 20% ×: The penetration rate of the emulsion has decreased by more than 20% immediately after preparation, or the generation or separation of particles has been confirmed

・Evaluation of operability at low temperature Heat to 30°C, put 60mL of the treatment agent for synthetic fibers that has been stirred and homogenized into a 100mL polyethylene bottle (inner diameter 45mm) with a cap, and then seal the container tightly. The polyethylene bottle filled with the processing agent for synthetic fibers was left to stand for 3 days in an incubator with a set temperature of -5°C. After standing still, the appearance of the aqueous liquid was visually judged, and evaluation was performed according to the following criteria. "Fluidity" shown in the following criteria means that the polyethylene bottle filled with the treatment agent for synthetic fibers is tilted horizontally (90°), and when part of the aqueous liquid flows out of the container within 30 seconds, it is judged as Liquid. The results are organized as shown in Table 3. [Evaluation criteria for low temperature operability] ◎◎: There is no fogging or turbidity in the appearance, and it has fluidity ◎: Although it has fluidity, the appearance appears foggy and turbid, showing partial solidification ○: Although it is fluid, the appearance appears foggy and cloudy, and most of it is solidified ×: Completely solidified, no fluidity

・Manufacture of drawn yarn After drying polyethylene terephthalate with an intrinsic viscosity of 0.64 and a titanium oxide content of 0.2% by conventional methods, it is spun with an extruder at 295°C. On the line, the aqueous solution of the treatment agent for synthetic fibers prepared at a concentration of 10% is applied by the diversion oil supply method using a metering pump so that the adhesion amount of the treatment agent for synthetic fibers becomes 1.0%. Converging with the yarn guide, 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, and then stretched at a temperature of 4800m/min Coiling at high speed to obtain 83 denier and 36 stretched yarns.

・Evaluation of static electricity generation The stretched yarn obtained by the above-mentioned stretched yarn production was rewound to obtain a package yarn with a yarn weight of 200 g. The bobbin was conditioned for 3 days at 20°C and a relative humidity of 40%, and then the static electricity generation was measured and evaluated according to the following conditions. (condition) In an environment of 20°C and a relative humidity of 40%, set 20 bobbins on the creel for unwinding. After passing through the washer tensioner, adjust the angle of entry and exit to 10 degrees and the diameter of 2cm. , 3 aluminum oxide pins with a length of 5cm travel, and coil at a speed of 200m/min. At this time, at a position 20 cm away from the outlet of the third alumina pin, use a collector-type potentiometer to measure the static electricity (static electricity generation) of the sheet composed of 20 wandering raw wires. The measured values were evaluated according to the following criteria. The results are organized as shown in Table 3. [Evaluation criteria for static electricity generation] ◎: Static electricity generation is less than 0.5kV, excellent destaticizing property ○: Static electricity generation of 0.5kV or more and less than 2kV, good destaticization ×: Static electricity generated above 2kV, poor destaticizing performance

[table 3] distinguish emulsion stability low temperature operability Electrostatic 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 x x 〇 Comparative example 2 x x 〇 Comparative example 3 x x 〇 Comparative example 4 x x x

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

The treatment agent for synthetic fibers of the present invention, the synthetic fibers to which the treatment agent for synthetic fibers is attached, and the method for treating synthetic fibers can respond to recent trends in the spinning step, false twisting step, and post-processing step of synthetic fibers. High speed and excellent antistatic property can exert the effect of preventing static electricity and pilling. Furthermore, the treatment agent for synthetic fibers of the present invention is excellent in emulsion stability and low-temperature operability in an environment below freezing point, so even if it is stored in a low-temperature environment, the contained components are not separated, which contributes to making synthetic fibers The treatment agent adheres evenly.

Claims (10)

A treatment agent for synthetic fibers containing one or more cycloalkyl alkanol derivatives selected from the following general formula (1) and general formula (2); [Chemical 1]

(wherein, ring Q ^a : a ring alkylene group with 3 to 8 carbons R ^1a : a hydrogen atom or an alkyl group with 1 to 12 carbons R ^2a : a divalent hydrocarbon group with 1 to 12 carbons R ³ : a hydrogen atom, Or the residue A after removing the hydroxyl group from a monocarboxylic acid with 6 to 22 carbons; ^1a O: an alkoxyl group with 2 to 4 carbons (however, if there are more than 2 alkoxyl groups, they can be independently 1 or more types) m ^a : an integer from 0 to 100) [Chemical 2]

(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 : A residue obtained by removing two hydroxyl groups from a dicarboxylic acid having 4 to 12 carbon atoms). The processing agent for synthetic fibers as claimed in item 1, wherein, the cycloalkyl alkanol derivatives containing R ^1a of the above general formula (1) being a hydrogen atom and the R ^1b of the above general formula (2) being a ring of a hydrogen atom One or more selected from alkyl alkanol derivatives. As the processing agent for synthetic fiber of claim 1 or 2, wherein, containing from above-mentioned general formula (1) R ^2a is the cycloalkyl alkanol derivative of the divalent hydrocarbon group of carbon number 2～8 and above-mentioned general formula (2 ) R ^2b is one or more selected from cycloalkyl alkanol derivatives of divalent hydrocarbon groups having 2 to 8 carbon atoms. The treatment agent for synthetic fibers according to any one of claims 1 to 3, wherein ^R3 of the above general formula (1) is a residue obtained by removing the hydroxyl group from an aliphatic monocarboxylic acid with 6 to 22 carbon atoms One or more selected from cycloalkyl alkanol derivatives and cycloalkyl alkanol derivatives represented by the above general formula (2). The processing agent for synthetic fibers according to any one of claims 1 to 4, wherein the cycloalkyl alkanol derivative is contained in an amount of 0.01 to 30% by mass relative to the total mass of the processing agent for synthetic fibers. The treatment agent for synthetic fibers according to any one of Claims 1 to 5, which further contains a nonionic surfactant (except for the aforementioned cycloalkyl alkanol derivatives) and an ionic surfactant. The treatment agent for synthetic fibers according to any one of Claims 1 to 5, which further contains a smoothing agent, a nonionic surfactant (except for the above-mentioned cycloalkyl alkanol derivatives) and an ionic surfactant . The treatment agent for synthetic fibers as claimed in claim 6 or 7, wherein the above-mentioned ionic surfactant contains organic phosphate ester P1 shown in the following general formula (3), organic phosphate ester shown in the following general formula (4) P2 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, m ^c are independently synonymous with the rings Q ^a , R ^1a , R ^2a , A ^1a O, ^ma of the general formula (1); n : an integer of 2 to 4 R ⁵ : 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 the ring Q ^a , R ^1a , R ^2a , A ^1a O, ^ma synonymous with general formula (1), alkali metal, alkaline earth metal (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]

(wherein, ring Q ^d , R ^1d , R ^2d , A ^1d O(OA ^1d ), m ^d are independently combined with ring Q ^a , R ^1a , R ^2a , A ^1a O, m ^a is synonymous; M ² : alkali metal, alkaline earth metal (1/2), organic amine salt or hydrogen atom) [Chemical 5]

(wherein, rings Q ^e , R ^1e , R ^2e , A ^1e O, and ^me are independently synonymous with rings Q ^a , R ^1a , R ^2a , A ^1a O, and ^ma of general formula (1); M ^3. M ⁴ : each independently being 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 fiber according to any one of Claims 1 to 8 is attached. A method for treating synthetic fibers, comprising: attaching the synthetic fiber treating agent according to any one of claims 1 to 8 to the synthetic fibers in an amount of 0.1 to 5% by mass.