JPH03199471A - Modification of synthetic yarn - Google Patents

Abstract

PURPOSE:To provide synthetic yarn with excellent washing resistance and natural protein-like handle and touch of polyamino acid by treating the surface of synthetic yarn with polyamino acid and crosslinking agent. CONSTITUTION:The surface of synthetic yarn such as polyamide-based or polyester-based synthetic yarn is treated with a polyamino acid and a crosslinking agent (e.g. isocyanate-based crosslinking agent) to provide synthetic yarn with excellent washing resistance and handle and touch of silk, wool, etc.

Description

DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a method for modifying synthetic fibers and synthetic fiber fabrics.

(Conventional technology and problems) Synthetic fibers are fibers with excellent heat resistance, water resistance, etc.

However, compared to natural fibers, it feels cold when worn and lacks volume, making it difficult to get used to in terms of texture and feel. As a modification method, 1) a method for producing irregular cross-section fibers, hollow fibers, etc. by melt spinning is being developed in order to achieve a texture similar to silk. In addition, ii) a method of coating the surface of synthetic fibers with another resin has been proposed, as seen in Japanese Patent Application Laid-Open No. 73597/1983. Method i) improves the silky feel, eliminates the abnormal luster of synthetic fibers, and provides a voluminous feel.

However, compared to natural fibers, it has not reached the level of satisfaction. As for ii), although the texture and feel can be improved, there are problems such as peeling when washed and a decrease in functionality when washed repeatedly.

(Problems to be Solved by the Invention) The present invention has been made in view of the current situation. That is, the present invention utilizes the polypeptide structure similar to that of wool, silk, etc., which is a characteristic of polyamino acids, to impart texture and texture to synthetic fibers.
The purpose of this is to provide a material with a good tactile feel and at the same time good washing resistance.

(Means for Solving the Problem) In order to solve the problem, the present inventors have conducted extensive research on various polyamino acids and crosslinking agents, and have found that by combining polyamino acids and crosslinking agents, The present invention was completed based on the discovery that the washing resistance can be improved as well as the washing resistance.

That is, the present invention provides for modifying the feel and feel of synthetic fibers and synthetic fiber fabrics by treating the synthetic fibers with a polyamino acid and a crosslinking agent.

Synthetic fibers in the present invention include polyamide fibers typified by nylon, polyester fibers, acrylic fibers, vinylidene fibers, etc. Synthetic fiber fabrics include the above-mentioned fibers alone or a blend thereof, and cellulose fibers. fiber,
These include woven fabrics, knitted fabrics, and non-woven fabrics blended with wool. The polyamino acid used in the present invention is obtained from decarboxylation polymerization of amino acid N-carboxylic anhydride (hereinafter referred to as NCA). Typical examples include T-methyl glutamate, r-ethyl glutamate, T-benzyl glutamate, β-methyl aspartate, β-ethyl aspartate, β-benzylaspartate, valine, norvaline, leucine, isoleucine, norleucine, and phenylalanine. , methionine, glycine, alanine, etc., and any of their optically active forms or racemic forms may be used, or a copolymer of two or more of these may be used.

Examples of the crosslinking agent include isocyanate crosslinking agents and epoxy crosslinking agents as shown in formulas (1) to is preferably in the range of 1 to 6% by weight.

(IV) (■) (V) (■) υ (IX) In addition, the polymerization initiator of NCA used in the present invention has an amino group,
It is a compound having active hydrogen such as a hydroxyl group, and examples include ammonia, monomethylamine, dimethylamine, dimethylamine, ethylenediamine, propylenediamine, hexamethylenediamine, 1,4-cyclohexanediamine, 0-phenylenediamine, p -phenylenethia, toluene-2,4-diamine, 4.4
'-Diphenylmethanediamine, polyoxypropylenediamine, N,N-dimethylethylenediamine, N,N
- Dimethyl-1,3-propane cyano, isophorone diamine, 1,2-cyclohexane diamine, polysiloxane having -grade and secondary amino groups, amine compounds such as polybutadiene compounds, ethylene glycol, 1,3-butanediol, Alcohols such as hexamethylene glycol, polyester diol, polysiloxane having a hydroxyl group, and polybutadiene compounds, as well as urethane prepolymers having amines at both ends, can also be used.

The polymerization initiator is added in an amount of 0.01 to 10 mol%, preferably 0.1 to 2 mol%, based on NCA. In addition, tertiary amines such as trimethylamine, triethylamine, and tributylamine are used in combination as necessary.

Examples of the organic solvent in the present invention include N,N-dimethylformamide, formamide, N,N-dimethylacetamide, N-methylpyrrolidone, dioxane, tetrahydrofuran, diglyme, benzene, toluene, xylene, etc. may be used alone or in combination.

Furthermore, the processing method for modifying synthetic fibers in the present invention is as follows:
This can be done as follows.

i) Add a crosslinking agent to a solution of polyamino acid (concentration: 0.1 to 10% by weight) at a concentration of 0% to the solid content of the polyamino acid solution.
．． The one added in the range of 1 to 10% by weight is used as a processing fluid,
Synthetic fibers are soaked and a polyamino acid film is formed on the surface of the synthetic fibers by wet or dry coagulation.

ii) After immersing the synthetic fiber in a solution with a crosslinking agent concentration of 0.1 to 10% by weight, the synthetic fiber is further immersed in a polyamino acid solution.i)
In the same manner as above, a polyamino acid film is formed on the surface of the synthetic fiber.

ji) After forming a polyamino acid film on the surface of the synthetic fiber, it is further immersed in the same crosslinking agent solution as in ii).

i) to iii) It can be processed by any method, but the adhesiveness between the synthetic fiber and the polyamino acid film is i).

Slightly inferior to ii). Furthermore, method ii) involves complicated steps, and therefore method i) is preferably proposed.

(Function) When synthetic fibers are treated with a polyamino acid and a crosslinking agent, a very excellent texture and feel can be obtained, and the polyamino acid coating also has excellent washing resistance. In particular, the effect of isocyanate-based crosslinking agents is remarkable. This is because functional groups with active hydrogen of polyamino acids, active groups (NHZ, COOH, etc.) of synthetic fibers, or water adsorbed on the surface of synthetic fibers are cross-linked with those of polyamino acids, which is unique to boriagonoic acids. It is presumed that this is to coat the synthetic fibers with a tough film while maintaining the natural protein-like texture.

Hereinafter, the present invention will be explained in more detail with reference to Examples. In the Examples, evaluation of texture, touch, and washing resistance was performed by the following method.

Evaluation 1. Texture/feel 1-1 Sensory evaluation Better than standard cloth ○ No change Δ Inferior × It was evaluated on three levels.

1-2 Electrical properties (electrostatic properties) STATfCH
One second (potential drop time) was determined by the coulometric decay method using ONESTMI2ER (Shishido static electricity ■).

Evaluation 2. Washing resistance: Washed 10 times (HL
-10) The following fabrics were evaluated and compared in the same manner as in 1-1 and 1-2.

Synthesis Example (1) Synthesis of Initiator ■ (Urethane Prepolymer) In a reaction apparatus equipped with a stirrer, 500 parts of polytetramethylene glycol with a molecular weight of 2000 (manufactured by Sanyo Kabo), 111 parts of isophorone diisocyanate (Tokyo Kasei ■), and a catalyst were added. Then, 0.22 parts of an IO% toluene solution of dibutyltin dilaurate was added, the temperature was raised to 120 degrees, and the mixture was stirred for 3 hours. Next, after cooling to 70 degrees, 611 parts of N,N-dimethylformamide was added to obtain a 50% solution (referred to as Ia) of the isocyanate at both ends.

Next, in a reaction apparatus equipped with a stirrer,
300 parts of 000, 90 parts of N,N-dimethylformamide
494 parts of the above Ia and N,N were added thereto at room temperature.
-4944 parts of dimethylformamide was added and stirred for 3 hours to obtain an initiator (2) having both terminal amines (anine number 2980 ppm).

Synthesis Example (II) Synthesis of Initiator ■ (Urethane Prepolymer) In a reactor equipped with a stirrer, 500 parts of polyethylene glycol (manufactured by Sanyo Kayi Co., Ltd.) with a molecular weight of 12,000, 111 parts of inphorone diisocyanate, and 1 part of dibutyltin dilaurate as a catalyst were added.
0.22 parts of 0% toluene solution was added, the temperature was raised to 120 degrees, and the mixture was stirred for 3 hours. Next, after cooling to 70 degrees, N, N
-611 parts of dimethylformamide was added to obtain a 50% solution of isocyanate at both ends (referred to as I[a).

Next, diefamine D-2 was added to a reaction apparatus equipped with a stirrer.
100 parts of 000, 30 parts of N,N-dimethylformamide
Add 0 parts of the above 11a and 185 parts of N at room temperature.
185 parts of N-dimethylformamide was added and the mixture was stirred for 3 hours to obtain a release agent (2) containing amines at both ends (amine value: 1490 ppm).

Synthesis Example (III) Synthesis of Initiator (2) Initiator (2) having an amine value of 155 was obtained from Ila and isophorone diamine in the same manner as in the above (I [[).

Synthesis Example (IV) Synthesis of initiator ① An amine value of 1290 pp was obtained from IIa and polyoxyethylene diamine (molecular weight 400) in the same manner as in (III) above.
An initiator (■) of m was obtained.

Synthesis Example (V) Synthesis of Polyamino Acid A In a reaction apparatus equipped with a stirrer, NCAl of γ-methyl-L-glutamate was added.
11 parts, add 0 parts of NCAl of L-leucine, N, N-
660 parts of dimethylformamide and 150 parts of dioxane were added and stirred at room temperature to completely dissolve. There, Dieffamine D-2000 (manufactured by Mitsui Texaco Chemical) 2.
A solution of 77 parts of triethylamine, 0.666 parts of triethylamine, 60 parts of N,N-dimethylformamide, and 15 parts of dioxane was added dropwise at room temperature over 10 minutes. After stirring at that temperature for 30 minutes, the temperature was raised to 65 degrees and further stirred at that temperature for 2 hours.

The end point of the reaction was confirmed by IR that the absorption of NCA had disappeared.

Synthesis Example (VI) Synthesis of Polyamino Acid B NCA9 of γ-methyl-L-glutamate was added to a reaction apparatus equipped with a stirrer.
4.1 parts, add 25.0 parts of L-leucine NCA,
, 490 parts of N-dimethylformamide, 18 parts of dioxane
0 parts was added and stirred at room temperature to completely dissolve. Therein, 40 parts of initiator I, 0.666 parts of triethylamine, N
, N-dimethylform 741,200 parts, dioxane 15
A portion of the solution was added dropwise over 10 minutes at room temperature. At that temperature 3
After stirring for 0 minutes, the temperature was raised to 70 degrees, and the mixture was further stirred at that temperature for 4 hours. The end point of the reaction was confirmed by IR that the absorption of NCA had disappeared.

Synthesis Example (■) Synthesis of Polyamino Acid C Polyamino acid C was obtained in the same manner as in (Vl) above using initiator (■).

Synthesis Example (■) Synthesis of Polyamino Acid Polyamino acid was obtained in the same manner as in the above (Vl) using initiator (■).

Synthesis example (IX) Synthesis of polyamino acid E (Vl)
Polyamino acid E was obtained in the same manner as above using initiator (2).

Example-1 The solution of polyamino acid A obtained in Synthesis Example (V) was diluted 5 times with N,N-dimethylformamide, and Coronate EH (manufactured by Nippon Polyurethane) was used as the isocyanate crosslinking agent and Bunacol EX as the epoxy crosslinking agent. -301 (manufactured by Nagase Kasei) was added to polyamino acids in an amount of 5% each to form a processing liquid. A polyester knitted fabric specified by JIS L-0803 was immersed in this processing liquid, squeezed using a centrifuge to achieve a pick-up rate of 110%, and heated at 25°.
The fabric was immersed in hot water at 60°C for 1 minute and then in warm water at 60°C for 3 minutes, dehydrated, and dried with hot air at 120''C for 10 minutes to obtain a polyamino acid coated polyester knitted fabric.

This knitted fabric was evaluated according to evaluation methods 1 and 2.

The results are shown in Table 1.

Examples 2 to 5 The solutions of polyamino acids B to E obtained in Synthesis Examples (Vl) to (IX) were coated and evaluated in the same manner as in Example 1. The results are shown in Table 1.

Comparative Examples 1 and 2 Comparative Examples 1 and 2 are the results of the evaluation of the standard product alone and the evaluation of the Example 1 formulation without adding a crosslinking agent, respectively, and are shown in Table 1.

As can be seen from Table 1, coating with polyamino acids improves the texture, feel, and electrostatic properties, and in particular, the use of isocyanate compounds has a large effect on wash resistance and does not change even after washing. I understand.

Example 6 Using the processing fluid prepared in Example 1, the polyester knitted fabric was replaced with a nylon knitted fabric specified by JIS L-0803 and evaluated. The results are shown in Table 2.

Comparative Examples 3 to 4 Similar to Comparative Examples 1 to 2, the results of treating the nylon knitted fabric alone and without adding a crosslinking agent are shown in Comparative Examples 3 and 4, respectively, and Table 2
Shown accordingly.

Effects of the Invention As described above, according to the processing method of the present invention, it is possible to impart the natural protein-like texture and feel of polyamino acids to synthetic fibers, and at the same time improve the washing resistance, which has been a problem in the past. Therefore, as the population is expected to increase in the future, this knowledge is useful when considering that clothing materials are synthetic products and natural resources are used for food.

Claims (1)

[Claims] A method for modifying synthetic fibers, which comprises treating the surface of synthetic fibers with a polyamino acid and a crosslinking agent.