JPS5951623B2 - Smoothing agent for thermoplastic synthetic fibers - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a smoothing agent for thermoplastic synthetic fibers having excellent heat resistance.

The purpose of the present invention is to obtain a smoothing agent that has both high heat resistance and high smoothness by using a particularly special ester component.

Thermoplastic synthetic fibers are coated with a smoothing agent to impart smoothness, cohesiveness, antistatic properties, etc. to the fibers in order to ensure smooth operation during the manufacturing process.

Thermoplastic synthetic fibers may be subjected to heat treatment in the manufacturing process depending on their use, and therefore, in addition to the above-mentioned properties, heat resistance such as smoke prevention and tar prevention is required for smoothing treatment.

Conventionally, treatment agents based on mineral oil, monovalent esters of higher fatty acids and lower alcohols, and divalent esters of higher alcohols and aliphatic dicarboxylic acids have been used as smoothing agents, but they generate a lot of smoke during heat treatment. Problems have occurred, such as significantly worsening the working environment and the accumulation of thermally decomposed or repolymerized processing agents as tar on the plates, rollers, etc. where heat treatment is performed, deteriorating operability.

In recent years, fibers for tire cords, etc., have been subjected to high-temperature heat treatment in order to achieve their characteristic performance.
Smoothing agents that adhere to fibers are now required to have an increasingly high degree of heat resistance.

Many studies have been conducted to improve the heat resistance of smoothing agents for thermoplastic synthetic fibers.
No. 6133), a processing agent whose main component is an ethylene oxide-added alkyl ether of bisphenol A (Japanese Patent Publication No. 47-2
No. 9474) etc. have been proposed.

Although these processing agents have certainly reached a very satisfactory level in terms of heat resistance against smoke generation, tar, etc., they are all unsatisfactory in terms of smoothness, causing thread breakage and thread breakage during fiber manufacturing and processing operations. It has the disadvantage of causing problems such as a decrease in yarn strength.

In other words, it has conventionally been recognized that a processing agent with good heat resistance has poor smoothness, and a processing agent with excellent smoothness has poor heat resistance. It has not been done.

On the other hand, in order to streamline the manufacturing process of fibers, processing speeds have been increasing, and as a result, there has been a strong demand for the development of smoothing agents that have both high heat resistance and high smoothness. Became.

The present invention has been made in response to the above requirements.

That is, the present invention has the general formula: [However, ■ and m are each independently a numerical value of 4 to 12,
k and n are each independently a numerical value of θ to 10, R and R' are residues of a monohydroxy compound having 2 to 22 carbon atoms, and
and X' is an alkylene group having 2 to 4 carbon atoms which may have a side chain, and Y and Y' are hydrogen or an alkyl group having 1 to 4 carbon atoms which may have a side chain. The present invention relates to a smoothing agent for thermoplastic synthetic fibers.

In the compound represented by the above formula [I], R and R'
represents a monohydroxy compound residue having 2 to 22 carbon atoms, preferably 12 to 18 carbon atoms.

Examples of the monohydroxy compound include saturated or unsaturated aliphatic alcohols (which may have side chains), alicyclic alcohols, and alkyl-substituted phenols, with aliphatic alcohols being particularly preferred.

Preferred aliphatic alcohols include octyl alcohol, 2-ethylhexyl alcohol, lauryl alcohol, trityl alcohol, cetyl alcohol, synthetic alcohols (such as Ziegler alcohol, oxo alcohol, etc.), oleyl alcohol, rylyl alcohol, matcha alcohol, and beef tallow reduced alcohol. , coconut oil reduced alcohol, and the like.

Particularly preferred alcohols are lauryl alcohol and oleyl alcohol.

R and R' may be the same or different.

X and X' are alkylene groups that may have side chains, and these groups are mainly derived from ethylene oxide, propylene oxide, butylene oxide, etc., but are not limited thereto.

X and X' may be the same or different, and (
The groups represented by XO)k and (x'o)n may themselves be polymerization components of different alkylene oxides or, in other words, random or block polymerization components of, for example, ethylene oxide and propylene oxide.

Preferably (XO)h and (x'o). is an oxyethylene group or a group containing both an oxyethylene group and an oxypropylene group.

Y and Y' are hydrogen or an alkyl group that may have a side chain, such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, etc., and preferably Y and Y' is hydrogen or t-
It is a butyl group, particularly preferably hydrogen.

Y and Y' may be the same or different.

k and n are each independently a number from 0 to 10.

Preferably it is 0-5, particularly preferably 1-4.

When either k or n exceeds 10, tar formation tends to increase and heat resistance tends to deteriorate.

(2) and m are each independently a number of 4 to 12, preferably 6 to 8, particularly preferably 6.

When either (1) or (m) exceeds 12, tar formation tends to increase and heat resistance tends to decrease.

The compound used in the present invention is a dicarboxylic acid represented by the general formula: RO(XO), H and R'O(X'0) n(III
:) may be produced by esterifying.

The compound represented by formula [I■] can be obtained by, for example, combining an alicyclic compound having a carbonyl group (e.g. cyclohexanone) and an aromatic compound having a polymerizable unsaturated bond (e.g. styrene, vinyltoluene, etc.) using a known method (e.g. Fenton). ring opening with a reagent).

Further, the compound represented by formula [III] can be easily obtained by reacting a hydroxyl compound with ethylene oxide, propylene oxide, etc. alone or in combination.

Compound [I] can be obtained by reacting compounds (II) and (III) at 120 to 200°C using, for example, p-)luenesulfonic acid as a catalyst.

The smoothing agent for thermoplastic synthetic fibers of the present invention usually contains about 10 to 90% by weight, preferably about 50 to 80% by weight of the compound represented by formula [I].

Furthermore, other components such as emulsifiers and antistatic agents, and if desired, conventionally known components that impart smoothness may be added within a range that does not impair heat resistance and smoothness. Examples of emulsifiers include polyoxyethylene castor oil ether, Polyoxyethylene hydrogenated castor oil ether, polyoxyethylene nonylphenyl ether and its laurate, polyoxyethylene thousand lauryl ether and its laurate, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan trioleate, oleyl phosphate as an antistatic agent and its salts (Na.

K, etc.), polyoxyethylene oleyl phosphate and its salts (Na, etc.), lauryl sulfone) (
Examples of the smoothing agent include alkyl silicones, copolymers of ethylene oxide and propylene oxide, and stearyl ether thereof.

The smoothing agent of the present invention may be applied to the fibers by a conventional method, such as a roller oiling method, a spray method, or a pump extrusion method, and can be applied in either an emulsion or straight state.

The amount of the smoothing agent of the present invention attached to the fiber is 0.2 per fiber.
~3.0% by weight (compound CI, 0.1-2.4 in the amount of l
% by weight) is preferred.

The smoothing agent of the present invention is used in the manufacturing and processing processes of thermoplastic synthetic fibers, and has good heat resistance and smoothness even in heat processes of 180 to 250°C. Suitable for smoothing in the manufacturing process of filament for industrial materials such as.

The present invention will be explained below with reference to Examples.

In addition, POE in the examples indicates a polyoxyethylene residue.

Example 1 In the general formula [■■] 1. 1 mol of a dicarboxylic acid in which both m is 6 and Y and Y' are hydrogen are reacted with 2 mol of POE (2 mol) lauryl ether at 170 to 180°C under a nitrogen atmosphere for 5 hours using p-)luenesulfonic acid as a catalyst. .

65 parts by weight of the reaction product, 25 parts by weight of POE (40 mol) castor oil ether, and 10 parts by weight of POE (20 mol) sorbitan trioleate were mixed, and smoothing agent A was prepared.
I got it.

Example 2 1 mole of a dicarboxylic acid of the general formula [■■] in which l and m are both 6 and Y and Y' are hydrogen, and 2 moles of POE (5 moles) and Ziegler alkyl (C = 12) ether were mixed with p- ) 170-180℃ under nitrogen atmosphere using luenesulfonic acid as a catalyst
React for 5 hours.

65 parts by weight of reaction product, POE (30 mol), 25 parts by weight of hydrogenated castor oil ether, and POE (20 mol)
A smoothing agent B was obtained by mixing 12 parts by weight of sorbitan trilaurate.

Example 3 1 mol of a dicarboxylic acid with the general formula CII'J, where both l and m are 6 and Y and Y' are hydrogen, and polyoxypropylene (
2 mol) 2 mol of lauryl ether was reacted with p-toluenesulfonic acid as a catalyst at 190-200°C under nitrogen atmosphere.
Time reacts.

A smoothing agent C was obtained by mixing 60 parts by weight of the reaction product, 20 parts by weight of POE (45 mol) castor oil ether, and 1.18 parts by weight of POE (10 mol) nonylphenyl lauret.

Table 1 shows the results of evaluating the smoking properties and tar formation of processing agents A, B, and C and conventional smoothing agents (Comparative Examples 1 and 2).

Smoothing agent
E (40 mol) Castor oil ether 25PO
E (20 mol) Sorbitan trioleate 10 Smoothing agent Y Formula Part by weight POE (2 mol) Bisphenol A dilaurate


65POE (30 moles) Castor oil ether 25POE (20 moles) Sorbitan trioleate 10 Test methods (1) Smoke generation test method: 1 g of smoothing agent was placed in a tube with a diameter of 100 m.
Place it in a stainless steel plate of size 1.5m, place it in a hot air dryer with the bottom of the plate horizontal, and measure the amount of smoke generated for 5 minutes at 220°C using a digital dust meter (model P-3, manufactured by Shibata Kagaku Kiki Kogyo Co., Ltd.). do.

(2) Tarring test, test method: The smoothing agent is treated at 220° C. for 4 hours in the same manner as the smoke test, and the tarry state is determined visually.

The evaluation criteria are as follows: ○: No tar formation △: Slight tar formation ×: Significant tar formation Example 4 A commercially available 70 denier nylon filament was washed and dried with hot water, and the smoothing agents A, B, and C were applied to it. ,X and V
Roller oiling was carried out using each of the 15% emulsions described above to obtain filaments to which 1% by weight of the smoothing agent was attached.

The treated filament was subjected to a fiber-metal running friction measuring machine, and the coefficient of friction between the fiber and metal was measured.

The results are shown in Table-2.

Example 1. 2. As is clear from 3 and 4, the conventional smoothing agent Although the performance is excellent, the coefficient of friction is large and the smoothness is poor.

On the other hand, the smoothing agent obtained in the present invention exhibits good performance in both smoothness (fiber-metal friction coefficient) and heat resistance (smoke resistance and tarring resistance).

Claims (1)

[Claims] 1 General formula: [However, 1 and m are each independently a numerical value of 4 to 12,
k and n are each independently a numerical value of O to 10, R and R' are residues of a monohydroxy compound having 2 to 22 carbon atoms, and X
and X' is an alkylene group having 2 to 4 carbon atoms which may have a side chain, and Y and Y' are hydrogen or an alkyl group having 1 to 4 carbon atoms which may have a side chain. Contains a smoothing agent for thermoplastic synthetic fibers.