JP2628462B2 - Synthetic fiber treatment agent - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a treating agent for synthetic fibers, and more particularly to a treating agent for synthetic fibers having good heat resistance used in the production and processing steps of fibers involving a heating step. is there.

[0002]

2. Description of the Related Art Conventionally, various processing agents have been used in the spinning and drawing steps of synthetic fibers according to the purpose. However, today, as the spinning and drawing speeds are increased and the processing is performed at a high temperature in order to improve productivity and quality, it is strongly desired to improve the lubricity and heat resistance performance of the fiber treatment agent. .

Conventionally, as a lubricating component of a synthetic fiber treating agent, paraffinic hydrocarbons such as mineral oil and higher fatty acid esters such as oleyl oleate, dioleyl adipate and dioleyl thiodipropionate have been generally used. I have.

Hitherto, higher fatty acid esters of neopentyl glycol have been proposed as lubricating components of fiber treatment agents, which are less decomposed, smoked and tarred.

[0005]

However, with these treating agents, when the winding speed is increased and the temperature of the heating roller is increased, tar on the roller increases, and hard tar remains, and the yarn touches it. There has been a problem that fluff and thread breakage increase. In addition, with respect to aromatic esters having good heat resistance, friction between fiber and metal increases, and fluff,
There has been a problem that the number of yarn breaks is so large that the yarn cannot be produced.

[0006]

Means for Solving the Problems The inventors of the present invention have less decomposition, fuming, and tarring and have good fiber-metal smoothness even under the severe heat treatment required in recent fiber production and processing steps. As a result of repeated studies for the purpose of obtaining a fiber treatment agent, the present invention has been achieved.

[0007] That is, the present invention is a synthetic fiber treating agent containing a compound represented by the following general formula (1).

[0008]

Embedded image

[0009] (wherein, R ^1, R ² each independently is an alkyl group having 1 to 30 carbon atoms; a R ^3, an alkyl group having 1 to 6 carbon atoms R ⁴ are each independently, and R ³ , R ⁴ has a total of 3 to 12. A is an alkylene group having 2 to 4 carbon atoms, m and n are each independently an integer of 1 to 3;
q and r are each independently 0 or an integer of 1 to 30)

In the present invention, R ¹ ,
R ² is each independently an alkyl group having 1 to 30 carbon atoms or a linear or side chain, and specific examples include a methyl group,
Ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group,
Examples thereof include an alkyl group having a straight chain or a side chain such as an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, and a nonadecyl group. Preferably, it is an alkyl group having a side chain having 8 to 26 carbon atoms, and particularly preferably, an isostearyl group, an isopalmityl group, an isononane group, or a 2-ethylhexyl group.

In the general formula (1), R ³ and R ⁴ are each independently an alkyl group having 1 to 6 carbon atoms, and the total thereof is 3
~ 12. The alkyl group having 1 to 6 carbon atoms may be a straight-chain or branched-chain alkyl group, and specific examples include a methyl group, an ethyl group, an n-propyl group, an iso-propyl group,
n-butyl group, sec-butyl group, iso-butyl group,
Examples include a tert-butyl group, an n-pentyl group, an iso-pentyl group, a tert-pentyl group, and a neo-pentyl group. Of these, an ethyl group, n-
A propyl group, an n-butyl group and an n-pentyl group are preferred, and an ethyl group and an n-butyl group are particularly preferred.

A in the general formula (1) is an alkylene group having 2 to 4 carbon atoms, and includes an ethylene group, a propylene group and a 1,2-butylene group. Of these, an ethylene group is preferred. m and n are integers of 1 to 3,
Preferably it is 1. q and r are 0 or an integer of 1 to 30, preferably 0 or 1 to 25. If it exceeds 30, it becomes a solid or a high-viscosity liquid, resulting in poor smoothness. When p is 2 or more, the alkylene oxide group represented by OA may be contained in the form of two or more kinds of blocks or random addition products.

Specific examples of the present invention include those shown in Table 1.

[0014]

[Table 1]

The compound represented by the general formula (1) of the present invention can be obtained by an esterification reaction between a carboxylic acid represented by the following general formula (2) and a polyhydric alcohol represented by the following general formula (3), or It can be obtained by a transesterification reaction between a carboxylic acid lower alkyl ester represented by the formula (4) and a polyhydric alcohol represented by the general formula (3).

[0016]

Embedded image

(Wherein R ¹ is an alkyl group having 1 to 30 carbon atoms)

[0018]

Embedded image

(R ³ and R ⁴ each independently have 1 to 6 carbon atoms.
And the total number of carbon atoms in R ³ and R ⁴ is 3
~ 12. A is an alkylene group having 2 to 4 carbon atoms;
m and n are each independently an integer of 1 to 3; q and r are each independently 0 or an integer of 1 to 30)

[0020]

Embedded image

(Wherein, R ¹ is an alkyl group having 1 to 30 carbon atoms; R ⁷ is an alkyl group having 1 to 3 carbon atoms)

Specific examples of the carboxylic acid include stearic acid, isostearic acid, lauric acid, oleic acid and 2-carboxylic acid.
Ethylhexanoic acid and the like are mentioned, and among these, isostearic acid, lauric acid and 2-ethylhexanoic acid are preferable. Specific examples of the lower alkyl carboxylate include methyl stearate, methyl isostearate, ethyl oleate, ethyl laurate, methyl 2-ethylhexanoate, and among these, methyl isostearate, ethyl laurate, −
It is methyl ethylhexanoate.

Specific examples of the polyhydric alcohol include, for example, 2-butyl-2-ethyl-1,3-propanediol,
2,2 diethyl-1,3-propanediol and the like.

Specific examples of the polyhydric alcohol alkylene oxide adduct include 2-butyl-2-ethyl-1,3
And ethylene oxide adducts such as -propanediol and 2,2 diethyl-1,3-propanediol.

In the esterification reaction, the ratio of carboxylic acid to alcohol is such that alcoholic hydroxyl equivalent / carboxyl equivalent is usually 1.3 to 0.7, preferably 1.1.
0.9. The reaction is generally carried out in the presence of
The reaction is carried out at a temperature of 00 ° C., preferably 130 to 170 ° C., and can be carried out under normal pressure, reduced pressure or increased pressure. The reaction time is usually 2 to 10 hours. Examples of the catalyst include those commonly used in esterification reactions, for example, paratoluenesulfonic acid, methanesulfonic acid, sulfuric acid, and metal-containing compounds (such as dibutyltin oxide and zinc acetate). The compound of the present invention can be obtained usually by purification using an adsorbent.

In the transesterification, the ratio of the lower alkyl carboxylate to the alcohol is usually such that alcoholic hydroxyl group equivalent / carboxyl group equivalent is 1.3.
To 0.7, preferably 1.1 to 0.9. The reaction is usually carried out in the presence of a catalyst at 100 to 200 ° C., preferably
To 170 ° C., and can be performed under normal pressure, reduced pressure, or increased pressure. The reaction time is usually 2 to 10 hours. Examples of the catalyst include those commonly used in transesterification reactions, for example, paratoluenesulfonic acid, methanesulfonic acid, sulfuric acid, and metal-containing compounds (such as dibutyltin oxide and zinc acetate). The compound of the present invention can be obtained usually by purification using an adsorbent.

The treating agent of the present invention may be used alone or as a mixture of two or more compounds represented by the general formula (1). Further, it may further contain at least one of a smoothing agent, an emulsifier and an antistatic agent.

As the leveling agent, mineral oil (refined spindle oil, liquid paraffin, etc.), animal and vegetable oil (coconut oil, castor oil, sardine oil, etc.), fatty acid ester (isostearyl laurate, oleyl oleate, dioleyl adipate, etc.) Alkyl ether esters (laurate adduct of lauryl alcohol with 2 moles of ethylene oxide, laurate of tridecyl alcohol with 3 moles of ethylene oxide), S-containing esters (such as diisostearyl thiodipropionate, diisocetyl thiodipropionate) And wax (paraffin wax, oxidized polyethylene wax, and the like), and among them, preferred are fatty acid esters and alkyl ether esters.

Examples of the emulsifier include nonionic surfactants (polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene / polyoxypropylene stearyl ether, hydrogenated castor oil ethylene oxide adduct, castor oil ethylene oxide adduct And sorbitol ethylene oxide adduct,
Trimethylolpropane ethylene oxide adduct, esterified product of pentaerythritol ethylene oxide adduct, etc.) and spun nonionic surfactants (span 20, span 80, span 85, etc.).

Examples of the antistatic agent include anionic surfactants (lauryl phosphate K salt, trioleyl phosphate K
Salt, cetyl phosphate Na salt, lauryl sulfate Na salt,
Polyoxyethylene lauryl ether sulfate sodium salt, sulfated oil sodium salt of rapeseed oil, oleic acid soap, lauryl sulfosuccinate sodium salt, tridecyl alcohol EO3 ether carboxylic acid sodium salt, lauroyl glutamate sodium
Salt, stearoyl taurate Na salt, lauroyl sarcosine Na salt, lauroyl alaninate Na salt, etc.), cationic surfactant (imidazoline type, arcobel A type,
Polyoxyethylene stearyl amino ether, lauryl dimethyl benzyl ammonium chloride, benzalkonium chloride, ethyl lanolin fatty acid aminopropylethyl dimethyl ammonium salt, etc.) and amphoteric surfactants (lauryl amino propionate Na salt, lauryl dimethyl betaine, 2-lauryl) -N-carboxymethyl-N-hydroxyethylimidazolinium betaine) and the like.

Further, the treating agent includes other additives and P
An H adjuster may be contained. Examples of the additive include an antioxidant, an ultraviolet absorber, a silicon compound, and a fluorine compound. Examples of the pH adjuster include an alkali metal and an alkylamine oxide adduct of an alkylamine.

The content of the compound represented by the general formula (1) in the total treating agent is not particularly limited, but is usually 10 to 9
0% by weight, preferably 10 to 80% by weight, particularly preferably 40 to 80%. . When the content of the compound represented by the general formula (1) is less than 10% by weight, the target high-speed spinning and fiber-metal smoothness during stretching cannot be maintained,
It is insufficient to prevent yarn breakage and improve operability.

The content of the leveling agent is usually 10 to 90% by weight, preferably 10 to 80% by weight. The content of the emulsifier is usually 10 to 70%, preferably 15 to 60% by weight. The content of the antistatic agent is usually 1 to 20% by weight, preferably 1 to 15% by weight. The content of additives is
Usually, it is 0.2 to 10% by weight, preferably 0.3 to 8% by weight. The addition amount of the pH adjuster is usually 0.02 to 10
%, Preferably 0.03 to 8% by weight.

The treating agent of the present invention has excellent heat resistance and is used in the production and processing steps of fibers. In particular, filaments for industrial materials having high strength made of thermoplastic synthetic fibers such as nylon and polyester are used. Suitable for the production process of fibers that require a severe heat process such as yarn and false twisted yarn.

The oil agent of the present invention is treated in a non-water-containing state or in an emulsion state emulsified with water in a melt-spinning step of a synthetic fiber, and then supplied to a spun yarn.
In the case of a non-water-containing treating agent, it is used as crude oil or diluted with a diluent (such as a low-viscosity mineral oil). The dilution ratio is usually 20 to 80% by weight, preferably 30 to 80% by weight based on crude oil.
７０70% by weight. The concentration of the emulsion is usually 5
It is 30% by weight, preferably 10 to 25% by weight.

There is no particular limitation on the oiling method, and nozzle oiling and roller oiling can be applied. The amount of the oil agent is usually 0.3 to 2.0% by weight, preferably 0.5 to 1.5% by weight, based on the fiber.

[0037]

The present invention will be described below with reference to examples, but the present invention is not limited to these examples.

Example 1 The compounds (Nos. 1 to 3) and the comparative treatment components (Nos. 4 to 6) according to the present invention shown in Table 2 were subjected to tar in a circulating drier at 240 ° C. for 4 hours. And 240 ° C
Fuming when dropped on a hot plate, and a 1% treatment agent component was adhered to a sample yarn obtained by washing and drying a commercially available 70-denier nylon filament yarn, and the coefficient of friction against metal was measured by a running yarn method. Table 3 shows the results.

[0039]

[Table 2]

[0040]

[Table 3]

Example 2 The following treating agents of the present invention (Nos. A to C) and comparative treating agents (Nos. DF) were tarified after being left in a circulating drier at 240 ° C. for 4 hours, and The smoke emission when dropped on a hot plate at 240 ° C., and the treatment agent was added to a sample yarn obtained by washing and drying a commercially available 70 denier nylon filament yarn with hot water.
Table 4 shows the results obtained by measuring the coefficient of friction against metal by the running yarn method after the adhesion. (Treatment agent A of the present invention) 1 60% by weight hydrogenated castor oil (EO) ₂₅ adduct 25% by weight Octyl alcohol (PO) (EO) adduct 15% by weight (Treatment agent B of the present invention) Dioleyl adipate 50% by weight Compound No. 2 10% by weight Hydrogenated castor oil (EO) ₂₅ adduct 25% by weight Octyl alcohol (PO) (EO) adduct 15% by weight (Treatment agent C of the present invention) Oleyl oleate 50% by weight 3 10% by weight hydrogenated castor oil (EO) ₂₅ adduct 25% by weight Octyl alcohol (PO) (EO) adduct 15% by weight (Comparative treating agent D) Dioleyl adipate 60% by weight hydrogenated castor oil (EO) ₂₅ adduct 25% by weight octyl alcohol (PO) (EO) adduct 15% by weight (comparative treating agent E) neopentyl glycol diisostearate 60% by weight hydrogenated castor oil (EO) ₂₅ adduct 25% by weight octyl alcohol (PO) ( EO) adduct 15 wt% (Comparative treating agent F) bisphenol A (EO) 2 dilaurate 60 wt% hydrogenated castor oil (EO) ₂₅ adduct 25 wt% octyl alcohol (PO) (EO) adduct 15 wt%

[0042]

[Table 4]

Evaluation: Evaluation of tar formation ◎: No tar formation ○: Slightly tar formation ×: Tar formation Smoke evaluation ○: Almost none ○ ~ △: Slightly present △: Slightly present ×: Violent smoke generation

[0044]

Industrial Applicability The synthetic fiber treating agent according to the present invention is excellent in heat resistance, smoke-generating property and smoothness at the time of production, and exhibits excellent spinning properties during melt spinning and stretching of polyester or nylon. In particular, heat resistance can be significantly improved by adding the treatment agent of the present invention.

 ────────────────────────────────────────────────── ─── Continuation of front page (56) References JP-A-50-59516 (JP, A) JP-A-56-159364 (JP, A) JP-A-58-220874 (JP, A)

Claims (2)

(57) [Claims] 1. A synthetic fiber treating agent comprising a compound represented by the following general formula (1). Embedded image (Wherein, R ¹ and R ² are each independently an alkyl group having 1 to 30 carbon atoms; R ³ and R ⁴ are each independently an alkyl group having 1 carbon atom.
And the total number of carbon atoms of R ³ and R ⁴ is 3-12. A is an alkylene group having 2 to 4 carbon atoms; m and n are each independently an integer of 1 to 3; q and r are each independently 0 or an integer of 1 to 30) 2. The synthetic fiber treating agent according to claim 1, further comprising at least one of a leveling agent, an emulsifier and an antistatic agent.