JPS6325107B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to a method for producing anti-pilling polyester fibers. More specifically, the present invention relates to a method for producing polyester fibers with excellent pilling resistance by treating polyester fibers containing special additives with an aqueous solution containing a specific quaternary ammonium compound and a specific amount of an alkaline substance. Polyester has many excellent properties and therefore has an extremely wide range of uses as a synthetic fiber. However, since polyester fibers have high strength, they are susceptible to pilling, especially when used as short fibers for clothing, and have the drawback of significantly impairing the feel and appearance quality. The tendency for pilling to occur differs depending on the texture, and is not so noticeable in thin to medium-weight fabrics with a dense texture, but it is particularly noticeable in thick fabrics and knitted fabrics with a loose texture, making commercialization difficult. . Conventionally, as a method for preventing pilling of polyester fibers, a method using a low degree of polymerization polyester has been proposed, as seen in Japanese Patent Publication No. 35-8562. However, this method not only has drawbacks in the manufacturing process such as decreased spinnability and spinnability, but also the resulting fibers have insufficient anti-pilling properties, so they cannot be used in the aforementioned thick woven or knitted fabrics. Furthermore, the fibers tend to become fibrillated as the degree of polymerization is lowered in an attempt to increase anti-pilling properties. In addition, special public service 47-29476
As seen in the publication, a method has also been proposed in which polyester fibers are treated with an aqueous solution containing a specific quaternary ammonium compound and an alkaline substance.
However, even if the treatment is carried out at high concentration and high temperature for a long time using this method, the anti-pilling effect on the above-mentioned thick fabrics and knitted fabrics is still insufficient.
The texture is hard and easily deteriorates, and there is a tendency for processing spots to occur and staining when dyed.
There are drawbacks such as the required amount of a treatment agent such as a quaternary ammonium compound, the difficulty in adopting a continuous treatment process, high costs, and yellowing of the woven or knitted fabric due to treatment. Further, even if the method disclosed in Japanese Patent Publication No. 47-29476 is applied to the above-mentioned low degree of polymerization polyester, the fibers are extremely likely to become fibrillated, making it impractical. The present inventor has conducted extensive research into a method for producing polyester fibers that do not have the above-mentioned drawbacks and also have excellent anti-pilling and anti-fibrillation properties that can be sufficiently applied to the aforementioned thick fabrics and lightly twisted knitted fabrics. Surprisingly, a modified polyester copolymerized with sodium 3,5-di(carbomethoxy)benzenesulfonate, monomethyl di-sodium phosphate or 5-
The above-mentioned special public interest was applied to fibers made of polyester obtained by mixing Na sulfoisophthalic acid Na salt.
By applying the method of Publication No. 29476, low concentration, low temperature,
It has been found that polyester fibers with excellent anti-pilling properties and anti-fibrillation properties and dramatically improved texture can be obtained by short-time treatment. Although it is not clear why such an effect is produced according to this method, a modified polyester obtained by copolymerizing sodium 3,5-di(carbomethoxy)benzenesulfonate in which a treatment agent is dispersed in polyester fibers,
While preferentially eluting monomethyl di-sodium phosphate or 5-Na sulfoisophthalate sodium salt, it quickly penetrates into the fiber interior and reduces fiber strength.
Since there is no need to use low polymerization degree polyester, it is structurally resistant to fibrillation, and special micropores are formed on the fiber surface and inside due to the elution of the above additives, making it as superior as natural fibers. It is thought that it will take on a new texture. Regardless of the reason, this method makes it possible to use mild processing conditions, so the texture does not become hard.
It is advantageous in terms of cost because it has fewer processing spots and is less likely to cause staining, requires less processing agent, and can easily be used in a continuous processing process. I learned that there are very important benefits. The present inventor completed the present invention as a result of further studies based on these findings. That is, the present invention relates to a modified polyester copolymerized with an organic sulfonic acid compound represented by the following general formula (), a phosphorus compound represented by the following general formula (), and a sulfonic acid compound represented by the following general formula (). A fiber made of polyester obtained by mixing at least one selected additive is mixed with (a) a quaternary ammonium compound represented by the following general formula () per 1 water.
0.1 to 5 milliequivalents and (b) alkaline substances 0.2 to 100
This is a method for producing anti-pilling polyester, characterized in that 0.5 to 40% by weight of the fibers are eluted by immersion treatment in an aqueous solution obtained by dissolving milliequivalents of the fibers. [Wherein, A is a trivalent aromatic group or an aliphatic hydrocarbon group, X is an ester-forming functional group, Y is an ester-forming functional group or a hydrogen atom, and M ¹ is a metal or a hydrogen atom. ] [In the formula, V is a monovalent organic group, Z is -OH, -
OV', -OM ⁵ or monovalent organic group (however, V' is 1
a valent organic group, M ⁵ is a metal), M ² is a metal, and m is 0 or 1. ] [Wherein, W is a hydrogen atom or an ester-forming functional group, M ³ and M ⁴ are metals, and n is 1 or 2. ] [In the formula, R ¹ is an alkyl group or alkenyl group having 8 or more carbon atoms, R ² is an alkyl group, cycloalkyl group, aryl group, aralkyl group, or a derivative thereof, and R ³ and R ⁴ are the same or different carbon atoms 1 ~4
represents an alkyl group or a derivative thereof, R ³ and R ⁴ may form a ring, An is a halogen atom,
OH, R ⁵ --OSO ₃ (wherein R ⁵ is an alkyl group). ] The polyester in the present invention has terephthalic acid as an acid component, and is preferably an alkylene glycol having 2 to 6 carbon atoms, such as ethylene glycol, trimethylene glycol, tetramethylene glycol, pentamethylene glycol, or hexamethylene glycol, particularly preferably ethylene glycol. The main target is polyester whose glycol component is at least one type of glycol selected from , trimethylene glycol, and tetramethylene glycol. It may also be a polyester in which part of the terephthalic acid component is replaced with another bifunctional carboxylic acid component, and/or a polyester in which part of the glycol component is replaced with a diol component other than the above-mentioned glycol. good. Furthermore, within the range where the polyester is substantially linear, it may be a polyester in which part of the terephthalic acid component and/or glycol component is replaced with a trifunctional or higher polyfunctional compound, and the degree of polymerization may be substantially reduced. It may also be a polyester copolymerized with a monofunctional compound as long as it does not cause any damage. Such polyesters can be synthesized by any method. For example, in the case of polyethylene terephthalate, usually terephthalic acid and ethylene glycol are directly esterified, a lower alkyl ester of terephthalic acid such as dimethyl terephthalate is transesterified with ethylene glycol, or terephthalic acid and ethylene glycol are transesterified. The first stage reaction is to react with terephthalic acid to produce a glycol ester and/or its low polymer, and the first stage reaction product is heated under reduced pressure until the desired degree of polymerization is achieved. It is produced by a second step of polycondensation reaction. The degree of polymerization of the above-mentioned polyester does not need to be particularly specified, but if the degree of polymerization is too low, the polyester fibers finally obtained will easily become fibrillated, so an intrinsic viscosity of 0.5 or more is preferable. Note that the intrinsic viscosity referred to in this specification was determined from the value measured at 35° C. using an O-chlorophenol solution. One of the additives to be mixed with the polyester in the present invention is a modified polyester obtained by copolymerizing an organic sulfonic acid compound represented by the following general formula (). In the formula, A is a trivalent aromatic group or an aliphatic hydrocarbon group, with aromatic groups being particularly preferred. M ¹ is a metal or a hydrogen atom, and particularly preferably an alkali metal or an alkaline earth metal. X is an ester-forming functional group, and specific examples thereof include

【formula】 【formula】

[Formula] (-CH ₂ -) _a OH, -O(CH ₂ )- _b -[O(CH ₂ )- _b ]- _d OH,

[Formula] (However, R is a lower alkyl group or a phenyl group,
(a and d are integers of 1 or more, b is an integer of 2 or more), etc. Y represents an ester-forming functional group or a hydrogen atom that is the same as or different from X, and is preferably an ester-forming functional group. Among such organic sulfonic acid compounds, particularly preferred examples include sodium (or potassium) 3,5-di(carbomethoxy)benzenesulfonate, sodium (or potassium) 3,7-di(carbomethoxy)naphthalene-1-sulfonate, ), sodium (or potassium) 2,5-bis(hydroxyethoxy)benzenesulfonate, and the like. In order to produce a modified polyester obtained by copolymerizing such an organic sulfonic acid compound, the organic sulfonic acid compound is added at any stage before the synthesis of the polyester described above is completed, preferably at any stage before the first stage reaction is completed. An acid compound may be added. At this time, the amount of the organic sulfonic acid compound to be used is in the range of 2 to 16 mol% based on the bifunctional carboxylic acid component (excluding the organic sulfonic acid component) mainly consisting of terephthalic acid that constitutes the modified polyester. preferable. The amount of the modified polyester to be mixed with the polyester is preferably 5 to 100 parts by weight of the modified polyester per 100 parts by weight of the polyester. In addition to the above-mentioned modified polyester, additives to be mixed with the polyester include phosphorus compounds represented by the following general formula () or () and/or
Alternatively, sulfonic acid compounds can be preferably mentioned. where M ² is a metal, especially an alkali metal,
Alkaline earth metals, preferably Mn1/2, Co1/2 or Zn1/2, especially Li, Na, K, Ca1/2Mg1/2
is particularly preferred. m is 0 or 1. V is a monovalent organic group, specifically an alkyl group, an aryl group, an alkylaryl group, an arylalkyl group, or -[-(CH ₂ )- _l O-] _p R″ (where R″ is a hydrogen atom , an alkyl group or a phenyl group, l is an integer of 2 or more, p
is an integer of 1 or more), etc. are preferable. Z is-OH,-
OV', -OM ⁵ or a monovalent organic group, V' is the same as the definition of V above, V' and V may be the same or different, and M ⁵ is the same as the definition of M ² above. Similar to the definition, M ⁵ and M ² may be the same or different. Further, the monovalent organic group is the same as the definition of the organic group in V above, and may be the same as or different from V. Preferred specific examples of such phosphorus compounds include monomethyl disodium phosphate, dimethyl monosodium phosphate, monophenyl dipotassium phosphate,
Monomethyl monomagnesium phosphate, monomethylmanganese phosphate, polyoxyethylene (addition of 5 moles of EO), potassium lauryl ether phosphate (however, addition of 5 moles of EO means addition of 5 moles of ethylene oxide, and hereinafter the same meaning) ,
Polyoxyethylene (EO5 mole addition) Lauryl ether phosphate magnesium salt, Polyoxyethylene (EO50 mole addition) Methyl ether phosphate sodium salt, Monoethyl dipotassium phosphite, Diphenyl monosodium phosphite, Polyoxyethylene (EO50 addition) molar addition) disodium methyl ether phosphite, monomethyl monosodium phenylphosphonate, monomethyl monopotassium nonylbenzenephosphonate, monomethyl monosodium phenylphosphinate, and the like. In the formula, M ³ and M ⁴ are metals, and M ³ particularly includes alkali metals, alkaline earth metals, Mn1/2,
Co1/2 or Zn1/2 is preferred, especially Li, Na,
K, Ca1/2, Mg1/2 are particularly preferred; ^M4 is particularly preferably an alkali metal or alkaline earth metal; among them, Li, Na, K, Ca1/2, Mg1/2 are particularly preferred; ^M3 and M ⁴ may be the same or different. n is 1 or 2. W is a hydrogen atom or an ester-forming functional group, and the ester-forming functional group is -COOR (wherein, R is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group)
or -CO[-O( _-CH2 ) _-l ] _-pOH (where l is an integer of 2 or more, p is an integer of 1 or more), etc. are preferred. Preferred specific examples of such sulfonic acid compounds include sodium 3-carbomethoxybenzenesulfonate-5-sodium carboxylate, and sodium 3-carbomethoxybenzenesulfonate-5.
- Potassium carboxylate, Potassium 3-carbomethoxybenzenesulfonate - Potassium 5-carboxylate, Sodium 3-hydroxyethoxycarbonyl benzenesulfonate - Sodium 5-carboxylate, Sodium 3-carboxybenzenesulfonate - 5-Carboxylate acid sodium, 3-hydroxyethoxycarbonyl benzenesulfonic acid
Na-5-carboxylic acid Mg1/2, benzenesulfonic acid Na-3,5-di (carboxylic acid Na), benzenesulfonic acid Na-3,5-di (carboxylic acid Mg1/2)
etc. can be given. Among them, phosphorus compounds and sulfonic acid compounds represented by the above general formulas () and () are particularly preferred since they have a remarkable effect of improving anti-pilling properties. The above-mentioned phosphorus compound and sulfonic acid compound can be produced by any method. For example, monomethyl disodium phosphate is easily produced by heating trimethyl phosphate, dimethyl phosphate, or monomethyl phosphate in glycol with sodium acetate, and each is added during polyester synthesis to form a polyester reaction system. It can also be produced by reacting inside. Sodium benzenesulfonate-3,5
-di(carboxylic acid Mg1/2) is, for example, 3,5-
It can be easily produced by heating and reacting sodium di(carbomethoxy)benzenesulfonate and magnesium acetate in glycol. The above-mentioned phosphorus compound or sulfonic acid compound may be mixed into the polyester at any stage before the end of the spinning process of melt-spinning the polyester into fibers.For example, it may be mixed into the polyester raw material or during the synthesis of the polyester. They may be mixed, or may be mixed after completion of synthesis and before melt spinning. The mixing amount of the above-mentioned phosphorus compound or sulfonic acid compound is suitably in the range of 0.3 to 15 mol%, and 0.5 to 5 mol% based on the acid component constituting the polyester to be added.
A mole % range is preferred. The fibers made of polyester mixed with the above-mentioned additives in the present invention may be solid fibers or hollow fibers, and the outer shape and the shape of the hollow portion in the cross section may be arbitrary, such as circular or hollow fibers. It doesn't matter if it's a strange shape or not. Any conventionally known method may be employed to produce such polyester fibers. The fiber thus obtained is immersed in an aqueous solution containing a quaternary ammonium compound and an alkaline substance in any form. That is, for example, cotton, tow, sliver, yarn of short or long fibers,
It can be processed in the form of woven or knitted fabrics, non-woven fabrics, rugs, etc. In addition to the polyester fibers mentioned above, other fibers such as cotton, hemp, rayon, polyacrylonitrile, polyamide, natural fibers such as ordinary polyester, and cellulose fibers can be processed. It can also be processed in the form of mixed fibers with fibers, synthetic fibers, etc. The following general formula () represents the quaternary ammonium compound used as a treatment agent in the present invention: Among them, R ¹ is an alkyl group or alkenyl group having 8 or more carbon atoms, R ² is an alkyl group, a cycloalkyl group,
Aryl group, aralkyl group or derivatives thereof,
R ³ and R ⁴ represent the same or different alkyl groups having 1 to 4 carbon atoms or derivatives thereof, and R ³ and R ⁴ may form a ring. An is a halogen atom, OH, R ⁵ ―
OSO ₃ (wherein R ⁵ is an alkyl group). Preferred specific examples of such quaternary ammonium compounds include octyltrimethylammonium bromide, octyldimethylbenzylammonium chloride, lauryltrimethylammonium chloride, lauryldimethylbenzylammonium chloride, lauryldimethylbenzylammonium hydroxide, stearyltrimethylammonium chloride, and cetyldimethylbenzyl. Ammonium chloride, stearyldimethylbenzylammonium chloride, oleyldimethylbenzylammonium chloride,
Lauryltrimethylammonium ethosulfate, lauryltriethylammonium chloride, lauryldiethylbenzylammonium chloride, lauryltrimethylammonium iodide, laurylbenzenetrimethylmethosulfate, cetyltrimethylammonium chloride, cetyldimethylarylammonium bromide, cetyldimethylcyclohexylammonium bromide, lauryl dimethyl hydroxyethylammonium chloride, stearyl ethyl dihydroxyethylammonium ethosulfate, lauryl trihydroxyethylammonium hydroxide, lauryl dibutylaryl ammonium bromide, lauryl dimethyl P-nitrobenzylammonium chloride, lauryl dimethyl O-chlorobenzylammonium chloride, distearyldimethylammonium chloride, laurylpyridinium chloride, etc. can be given. If the amount of the above-mentioned quaternary ammonium compound used is too small, the anti-pilling properties of the final polyester fiber obtained will be insufficient; on the other hand, if it is too large, the texture will tend to become hard and processing unevenness will become large. Since the yellowing problem may occur on top of the water, a range of 0.1 to 5 milliequivalents per water is appropriate, and a range of 0.5 to 3 milliequivalents is particularly preferred. Any water-soluble alkaline substance can be used as the alkaline substance to be used in combination with the above-mentioned quaternary ammonium compound, but among them, alkali metal hydroxides, carbonates, and alkaline earth metal hydroxides can be used. , carbonates are particularly preferred. Specific examples include potassium hydroxide, sodium hydroxide, lithium hydroxide, barium hydroxide, strontium hydroxide, calcium hydroxide, magnesium hydroxide, potassium carbonate, sodium carbonate, lithium carbonate, barium carbonate, strontium carbonate, and calcium carbonate. , magnesium carbonate, etc. The amount of the alkaline substance to be used is 0.2 per 1 water in order to synergistically improve the anti-pilling property in combination with the quaternary ammonium compound.
A range of 1 to 100 milliequivalents is preferred, and a range of 1 to 50 milliequivalents is particularly preferred. If the treatment temperature is too low, it will take a long time to obtain a sufficient treatment effect, and if the treatment temperature is too high, the texture and color tone of the resulting fibers will deteriorate. It may be possible to shorten the treatment time by increasing the temperature, but in this case spots are more likely to occur. Therefore, the processing temperature is 70 to 140
A temperature range of 80°C to 100°C is particularly preferred. The treatment time usually only needs to be about 10 minutes, and up to about 4 hours is sufficient. The weight loss rate of polyester fibers by treatment with an aqueous solution containing such a quaternary ammonium compound and an alkaline substance is suitably in the range of 0.5 to 40% by weight from the viewpoint of anti-pilling and fibrillation resistance, strength, and texture. A range of 2 to 20% is particularly preferred. By treating with an aqueous solution containing a quaternary ammonium compound and an alkaline substance,
A portion of the polyester fiber is eluted, resulting in a polyester fiber having excellent anti-pilling properties, anti-fibrillation properties, and improved hand. The polyester fiber of the present invention may contain optional additives, such as catalysts, color inhibitors, heat resistant agents, flame retardants, fluorescent brighteners, erasing agents, coloring agents, and inorganic fine particles, as necessary. You can leave it there. Further explanation will be given below with reference to Examples. Parts in Examples indicate parts by weight, and the anti-pilling properties and anti-fibrillation properties of the resulting polyester fibers were measured by the following method. (i) Anti-pilling property The test fabric was tested using an ICI type pulling tester at 60 rpm for 5 hours to determine the pill grade. Grades are classified into grades 1 to 5, with grade 5 being the best and grade 1 being the worst, and grade 3 or higher is practically required. (ii) Fibril resistance Polyethylene terephthalate was used as the friction cloth using a Gakushin type flat abrasion machine for friction fastness testing.
Using 100% dioset, the test fabric was
The surface was abraded a predetermined number of times under a load of g to check for the occurrence of fibrillation. Example 1 100 parts of dimethyl terephthalate, 60 parts of ethylene glycol, and 0.06 parts of calcium acetate monohydrate were placed in a transesterification tank, and the temperature was raised from 140°C to 230°C over 4 hours in a nitrogen gas atmosphere to produce methanol. The transesterification reaction was carried out while distilling it out of the system. The resulting product was then treated with trimethyl phosphate.
0.06 part, antimony trioxide 0.04 part, 3-hydroxyethoxycarbonylbenzenesulfonic acid Na-
4 parts of a 25% ethylene glycol solution of sodium 5-carboxylate and 0.35 parts of a 20% ethylene glycol slurry of titanium dioxide were added and transferred to a polymerization vessel. Next, the pressure was reduced from 760 mmHg to 1 mmHg over 1 hour, and at the same time the temperature was raised from 230°C to 280°C over 1 hour and 30 minutes. Under reduced pressure of 1 mmHg or less, polymerization temperature 280℃
Polymerization was continued for another 3 hours, for a total of 4 hours and 30 minutes, until the intrinsic viscosity
A polymer with a softening point of 0.640 and a softening point of 260°C was obtained. Short fibers (1.2 d x 38 mm cut length) having a triangular cross-sectional outer shape and a hollow portion with a hollow ratio of 18% were produced from this polymer by a conventional method. A 42-count spun yarn was produced using this staple fiber, and a 28-gauge smooth knitted fabric was knitted from it. After scouring and presetting this knitted fabric by a conventional method, 1.5 milliequivalents of lauryldimethylbenzylammonium chloride/
After immersion treatment at 90° C. for 30 minutes in an aqueous solution containing 12.5 milliequivalents of sodium hydroxide to reduce the weight by 4%, dyeing and final setting were performed. The obtained knitted fabric had a good feel and anti-pilling property of grade 4.5. Furthermore, microscopic observation after 200 wears showed that no fibrils were observed. Example 2 Sodium 3-hydroxyethoxycarbonylbenzenesulfonate-5-carboxylate used as an additive in the production of the polymer in Example 1
A polyester having an intrinsic viscosity of 0.554 and a softening point of 259°C was obtained by using 1 part of monomethyldiNa phosphate in place of the above. Short fibers with a round and solid cross section (cut length: 0.9 d x 38 mm) were produced from this polyester by a conventional method. The following procedure was carried out in the same manner as in Example 1 to obtain a smooth knitted fabric with a weight loss rate of 3.5%. The obtained knitted fabric had a good feel and anti-pilling property was grade 4.5. Also wear out
No fibrillation was observed by microscopic observation after 200 cycles. Example 3 100 parts of dimethyl terephthalate, 17.8 parts of Na 3,5-di(carbomethoxy)benzenesulfonate (11.7 mol% based on dimethyl terephthalate), 70 parts of ethylene glycol, 0.03 parts of manganese acetate tetrahydrate
1 part and 0.3 parts of sodium acetate trihydrate were placed in a transesterification reactor, and the temperature was raised from 140°C to 230°C over 4 hours to carry out the transesterification reaction while distilling the generated methanol out of the system. Subsequently, 0.03 part of a 56% aqueous solution of orthophosphoric acid and 0.04 part of antimony trioxide were added to the obtained product, and the mixture was transferred to a polymerization vessel. Next, the pressure was reduced from 760 mmHg to 1 mmHg over 1 hour, and at the same time the temperature was raised from 230°C to 280°C over 1 hour and 30 minutes. Under reduced pressure of 1 mmHg or less, polymerization temperature 280℃
Polymerization was continued for another 30 minutes for a total of 2 hours, and the intrinsic viscosity was 0.405.
A copolymer with a softening point of 200°C was obtained. 15 parts of chips and intrinsic viscosity of this copolymer
0.710 polyethylene terephthalate chips 85
5 in a Nauta mixer (manufactured by Hosokawa Iron Works).
After mixing for 2 minutes and drying at 110°C for 2 hours and then at 150°C for 5 hours, the
The mixture was melted and kneaded at 275°C to form chips. Using this polymer, the same procedure as in Example 1 was carried out to obtain a smooth knitted fabric with a weight loss rate of 4%. This knitted fabric had a good feel and anti-pilling property was grade 3.5. Furthermore, no fibrillation was observed in microscopic observation after 200 wears. Comparative Example 1 Short fibers with a round solid cross section (0.9d×
A cut length of 38 mm was obtained. A 42-count spun yarn was produced from this staple fiber, and a 28-gauge smooth knitted fabric was knitted from this spun yarn.
After refining and presetting this knitted fabric using conventional methods,
A weight loss of 4% was achieved by immersion treatment at 130° C. for 30 minutes in an aqueous solution containing 15 meq. of lauryldimethylbenzylammonium chloride and 50 meq. of sodium hydroxide. The knitted fabric after weight loss was discolored to yellow. Subsequently, staining and final setting were performed. The obtained knitted fabric had a hard texture and dyed spots were observed. The fibrillation resistance was grade 3, and significant fibrillation was observed by microscopic observation after 200 wears. Comparative Example 2 3-Hydroxyethoxycarbonylbenzenesulfonic acid used as an additive in Example 1
A polyester having an intrinsic viscosity of 0.641 was obtained in the same manner as in Example 1, except that Na.5.Carboxylic acid Na was not used. The weight loss rate is 1
%, and the anti-pilling properties were the same as those of grade 1 and untreated.

Claims (1)

[Scope of Claims] 1 Consisting of a modified polyester copolymerized with an organic sulfonic acid compound represented by the following general formula (), a phosphorus compound represented by the following general formula (), and a sulfonic acid compound represented by the following general formula () Fibers made of polyester obtained by mixing at least one additive selected from the group are mixed with 1 part of water.
The fibers are immersed in an aqueous solution obtained by dissolving (a) 0.1 to 5 milli equivalents of a quaternary ammonium compound represented by the following general formula () and (b) 0.2 to 100 milli equivalents of an alkaline substance. 0.5~40
1. A method for producing anti-pilling polyester fiber, characterized by eluating % by weight. [Wherein, A is a trivalent aromatic group or an aliphatic hydrocarbon group, X is an ester-forming functional group, Y is an ester-forming functional group or a hydrogen atom, and M ¹ is a metal or a hydrogen atom. ] [In the formula, V is a monovalent organic group, Z is -OH, -
OV', -OM ⁵ or monovalent organic group (however, V' is 1
a valent organic group, M ⁵ is a metal), M ² is a metal, and m is 0 or 1. ] [Wherein, W is a hydrogen atom or an ester-forming functional group, M ³ and M ⁴ are metals, and n is 1 or 2. ] [In the formula, R ¹ is an alkyl group or alkenyl group having 8 or more carbon atoms, R ² is an alkyl group, cycloalkyl group, aryl group, aralkyl group, or a derivative thereof, and R ³ and R ⁴ are the same or different carbon atoms 1 ~4
represents an alkyl group or a derivative thereof, R ³ and R ⁴ may form a ring, An is a halogen atom,
OH, R ⁵ --OSO ₃ (wherein R ⁵ is an alkyl group). ] 2 The alkaline substance is an alkali metal hydroxide,
The method for producing polyester fibers according to claim 1, wherein the polyester fiber is at least one compound selected from alkaline earth metal hydroxides, alkali metal carbonates, and alkaline earth metal carbonates. 3 The temperature of the aqueous solution during immersion treatment is 70 to 140℃
A method for producing polyester fiber according to claim 1 or 2. 4. The method for producing polyester fibers according to any one of claims 1 to 3, wherein the dipping treatment time is 10 minutes or more. 5 The polyester that is the base of the polyester fiber has the following formula It consists mainly of repeating units with an intrinsic viscosity of at least
0.5 of the polyester fiber according to any one of claims 1 to 4.