JPS58132114A - Production of synthetic fiber - Google Patents

Abstract

PURPOSE:Isophthalic acid containing a sulfonate salt, a specific phosphorus compound and a lithium compound are added, then the polymerization reaction between terephthalic acid or its derivative and glycol is conducted, the polymer is made into fibers, and a part of the fibers is leached out with an alkali to produce synthetic fiber having special fine pores and good dyeing properties. CONSTITUTION:When terephthalic acid or its ester-forming derivative and glycol are made to react into polyester and the polymer is made into synthetic fibers, (A) 0.5-10mol%, based on the total acid components, of isophthalic acid containing alkali metal sulfonate groups, (B) 0.3-3mol%, based on the total acid components, of a phosphorus compound of the formula (R<1>, R<2> are H, organic group; X is H, organic group, metal; m is 0, 1), (C) a lithium compound are added so that the total equivalents of the metals in components B and C becomes 2.0-3.2 times the molar quantity of component B. Then, the resultant fibers are treated with aqueous alkali to cause more than 2wt% leaching to give the objective fibers.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a synthetic fiber O manufacturing method KI1g. More details JII
K is made of polyester that has anti-fungal pores and exhibits a 9-color oiliness and brightness that is resistant to colored WIiK. Because of its properties, it is widely used as a synthetic fiber. However, compared to natural fibers such as #IO in wool, cellulose fibers such as rayon and acetate, and acrylic fibers, polyester ridges have less depth of color when dying and have poor color development and clarity. There are disadvantages that are inferior to.

In the past, attempts have been made to improve dyes and chemically modify polyester in order to overcome this drawback, but none of these efforts have been sufficiently effective. In addition, we have developed a method for forming a transparent thin film on the surface of polyester fibers and a method for forming a transparent thin film on the surface of polyester fibers,
A method has been proposed in which fine irregularities are formed on the fiber surface by applying plasma irradiation at 500 rrJvsec/ed. However, even with these methods, the effect of improving the depth of color is insufficient, and in addition, the transparent thin film formed on the fiber surface [falls off on the product after company washing, etc., and its durability is insufficient]. However, in the method of applying plasma irradiation,
Since no unevenness occurs on the surface If of the fiber in the fiber portion that is in the shadow of the irradiated surface, there is a drawback that the smooth kneaded m surface appears on the surface due to the rolling of the thread within the fiber structure during wearing, resulting in color discoloration.

On the other hand, as a method for imparting irregularities to the surface of polyester fibers, polyester fibers made of polyoxyethylene glycol or polyester containing polyoxyethylene glycol and a sulfonic acid compound are buried in an alkaline aqueous solution to align them in the fiber axis direction. Hygroscopic fiber O11 manufacturing method that forms wrinkle-like micropores on the surface of the fiber, or zinc oxide.

Polyester fine particles made by adding fine particles of an inert inorganic substance such as calcium phosphate to a polyester reaction system are treated with an alkaline aqueous solution to elute the inorganic fine particles, thereby forming fine pores.1. Manufacturing methods etc. have been proposed. However, the fibers obtained by these methods do not have the effect of improving color depth.
This is not observed, and on the contrary, a decrease in visual acuity tO is observed. That is, in these methods, if the treatment with the alkaline aqueous solution is not sufficient, no effect of improving the depth of color is observed; on the other hand, when the treatment with the alkaline aqueous solution is sufficient, there is no improvement in the depth of the color. , probably due to the diffuse reflection of light by the micropores, the line-of-sight density decreases, and even if it is colored in a dark color, it looks whitish. I
The strength of LIIIA is significantly reduced and it becomes easily fibrillated, making it unusable for practical use.

Also, particles lll! Fibers made of polyester containing inorganic fine particles such as silica of 80 mμ or less are subjected to alkali weight loss treatment to give irregular irregularities of 0.2 to 0.7μ on the fiber surface, and 50 to 200W+μ within these irregularities.
A method has been proposed to improve the depth of color by creating fine irregularities. However, even with this method, the effect of improving color depth is insufficient, and
On top of that, it may be rounded off by the extremely complicated uneven layer, or polished.
The irregularities were destroyed by the physical action from the outside of IIIp, and the destroyed part became significantly discolored and had a difference in gloss compared to other destroyed raised parts, and furthermore, it easily became fibrillated. There is a drawback.

The inventor of the present invention has conducted extensive research in an attempt to provide a polyester fiber that does not have the above drawbacks and has excellent color depth and clarity by adding micropores to the polyester fiber, and has found that a specific amount of divalent phosphorus The compound is synthesized by adding this pentavalent (calciumized metal in a specific ratio to the Q phosphorus compound) to the polyester reaction system without reacting in advance, and the polyester fiber obtained by melt-spinning the polyester is treated with alkali. By doing this, a large number of special microvoids can be formed, and this makes it possible to color the polyester fiber, which has excellent depth and clarity of color, has sufficiently little discoloration due to friction, and has excellent fibril resistance. Find out what can be obtained and propose it first.

However, the polyester fiber dye obtained in this way can only be dyed with disperse dyes, which cannot be said to have very good color vividness. Therefore, in order to obtain even better depth and sharpness of nine colors, it is desirable to modify the polyester fiber to be dyeable with cationic dyes so that it has excellent sharpness and can use cationic dyes.

The present inventor attempted to obtain a polyester fiber having a large number of ξ-glides on the fiber surface and in its vicinity, similar to those obtained with the above-mentioned polyester fibers, and which is dyeable with cationic dyes, by adding alkali metal sulfonate groups. Various methods were investigated for modifying the polyester with an isophthalic acid component and adding the above-mentioned pentavalent phosphorus compound and calcium compound without reacting them in advance during the synthesis of the polyester.

As a result, when a phosphorus compound and a calcium compound are added during the synthesis of a polyester modified with an isophthalic acid component having an alkali metal sulfonate group, the modification with an inophthalic acid component having an alkali metal sulfonate group is removed and the normal polyester is Since the dispersion state of the internally precipitated particles in the resulting polyester tends to be poor compared to when it is added during the synthesis of polyester, it becomes difficult to obtain a polymer with poor transparency. There is a problem in that macrovoids are formed on the surface of polyester fibers after alkali treatment, making it difficult to see the effect of improving the depth and clarity of the color at the end of the dyeing process, and even reducing the visual fa. I found out.

The inventors of the present invention have conducted extensive studies to solve this problem, and have surprisingly found that by using a lithium compound in place of the calcium compound in the above-mentioned method, the dispersibility of the internally precipitated particles is good and the transparency is improved. A polyester dyeable with cationic dyes with excellent properties can be reliably obtained without loss of reproducibility, and by alkali treatment of polyester fibers melt-spun from this polyester, many microvoids can be formed on the fiber surface and its vicinity. It was discovered that a polyester fiber with improved color depth and clarity, excellent color fastness, sufficiently small discoloration due to friction, and excellent fibril resistance can be obtained when dyed with a polyester fiber. The present invention has been completed as a result of extensive studies based on this knowledge.

That is, the present invention provides synthetic fibers made of polyesters synthesized by the reaction of dicarboxylic acids, mainly terephthalic acid, or their ester-forming derivatives, and at least one glycol or their ester-forming derivatives. (a) isophthalic acid or an ester-forming derivative thereof having an alkali metal sulfonate group in an amount of O,S to 10 mol based on the total acid component (b) A phosphorus compound (c) represented by the following general formula in an amount of 03 to 3 mol. The total number of metal equivalents is 2.0 to 3.2 relative to the number of moles of the compound (b) 1)
A method for producing synthetic fibers, which is characterized in that the polyester is added in an amount of double the amount, then the synthesis of the polyester is completed, and after melt-spinning the obtained nine polyesters, 2% by weight or more of the polyester is eluted with an aqueous solution of an alkali compound. be.

The polyester referred to in the present invention has an acid component that produces terephthalic acid and a glycol component that produces at least one type of glycol, preferably at least one alkylene glycol selected from ethylene glycol, trimethylene glycol, and tetramethylene glycol. The main target is polyester.

may be a polyester in which a portion of the terephthalic acid component is replaced with another difunctional carboxylic acid component, and/
Alternatively, a part of the glycol component may be replaced with the above-mentioned glycol other than the main component or another diol component to form a polyester.

The difunctional cardanic acid other than terephthalic acid used here is, for example, isophthalic acid.

Naphthalene dicarboxylic acid, diphenyl dicarboxylic acid, diphenoxyethane dicarboxylic acid, β-hydroxyethoxybenzoic acid, p-oxybenzoic acid 11. Aromatic and fatty acids such as adipic acid, sebacic acid, and 1,4-cyclohexanedicarboxylic acid.

Examples include alicyclic 3-functional carboxylic acids. Examples of diol compounds other than the above-mentioned glycols include cyclohexane-1,4-dimetatool, neopentyl glycol, bisphenol A, and bisphenol 8! Side fat family.

Examples include alicyclic and aromatic diol compounds and polyoxyalkylene glycols.

Such polyesters may 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 involves reacting with terephthalic acid glycol ester and/or its low polymer, and the reaction product of the first stage is heated under reduced pressure to polymerize until the desired degree of polymerization is achieved. It is produced by a second stage of reaction.

Isophthalic acid having an alkali metal sulfonate group or its ester-forming 4' conductor is added to the polyester of the present invention at any stage until its synthesis is completed, and by polymerizing it, it is added to the main chain of the axillary polyester. Alkyle/-5-alkali metal sulfoisophthalate units are introduced. Preferred specific examples of inphthalic acid or its ester-forming derivative having an alkali metal sulfonate group include sodium 3,5-di(carboxy)benzenesulfonate, lithium 3,5-di(carboxy)benzenesulfonate, S, Potassium S-(carboxy)benzenesulfonate, Sodium 3,5-di(carbomethoxy)benzenesulfonate, Lithium 3,5-di(carbomethoxy)benzenesulfonate, 3,5-di(
Potassium carbomethoxy)benzenesulfonate, 3,5
-Di(β-hydroxyethoxycarbonyl)benzenesulfonate 9') '+ 31 s-Lithium (β-hydroxyethoxycarbonyl)benzenesulfonate, 3,5-di(β-hydroxyethoxycarbonyl)
Potassium benzenesulfonate, sodium 3,5-di(γ-hydroxyglopoxycarponyl)benzenesulfonate, 3,5-di(δ- and dicarbonyl in sulfate) penganesulfonate, a, s-shi(δ-
Examples include lithium hydroxybutoxycarbonyl)benzenesulfonate.

The amount of isophthalic acid or its ester-forming derivative having an alkali metal sulfonate group is in the range of 0.5 to 10 mol, preferably in the range of 1 to 6 mol, based on the total components constituting the armpit polyester. It is. If the amount added is less than 0.5 mol, the final polyester fiber cannot be dyed in a sufficiently deep color with the cationic dye, and if it exceeds 10 mol, the affinity for the cationic dye will be saturated. This is not preferable because the excellent physical properties peculiar to polyester fibers are impaired and the manufacturing cost increases significantly. The timing of addition of inphthalic acid having an alkali metal sulfonate group or its ester-forming derivative is before the completion of the second stage reaction of polyester synthesis.
3. In the case of bisglycol esters such as alkali metal salts of S-di(β-hydroxyethoxycarbonyl)benzenesulfonic acid, the second stage of depressurization starts after the first stage of transesterification, esterification, or ethylene oxide addition reaction. This is a stage before the start of the reaction, and 3,9-
In the case of lower alkyl esters such as alkali metal salts of di(carbomethoxy)benzenesulfonic acid, 3. S-di(carboxy)
In the case of an alkali metal benzenesulfonic acid salt, this is the stage before the start of the esterification reaction.

Furthermore, when copolymerizing an iso-7-talic acid component having a metal sulfonate group, a large amount of ether bonds may be produced as a by-product. can be avoided.

The phosphorus compound used in the present invention is a phosphorus compound represented by the following general formula, where Bl and V are hydrogen atoms or -
It is a valent organic group. Specifically, this monovalent organic group is an alkyl group, an aryl group, a yral group
*)zO)IR” (L and Rs are hydrogen atoms, alkyl groups, aryl groups, or aral groups, l is an integer of 2 or more,
k is an integer of 1 or more), and R1 and R8 may be the same or different. X is a hydrogen atom, a -valent organic group, or a metal, and the -valent organic group is the above-mentioned Bl.

Same as the definition of the organic group in R3, R1゜R3
The metals may be the same or different, and the metals are particularly preferably alkali metals and alkaline earth metals, and among them, moss is particularly preferred. m #i is an integer of 0 or 1.

Examples of such phosphorus compounds include orthophosphoric acid.

Triesters of acids such as trimethyl phosphate, triethyl phosphate, tributyl phosphate, and triphenyl phosphate, methyl acid phosphate.

Phosphoric acid mono- and diesters such as ethyl acid phosphate, butyl acid phosphate.

phosphorous acid, trimethyl phosphite, triethyl phosphite,
Phosphite triesters like tributyl phosphite, triphenyl phosphite, methyl acid phosphite, ethyl acid phosphite.

Phosphorus compounds obtained by reacting with mono- and di-esters of sulfur, such as butyl acid phosphite, the above-mentioned phosphorus compounds i'/recall and/or water, and further adding the above-mentioned phosphorus compounds in equimolar amounts to the phosphorus compounds. One or more phosphorus compounds selected from phosphorus compounds obtained by reacting with a lithium compound can be used.

The lithium compound to be used in combination with the above phosphorus compound is not particularly limited as long as it reacts with the above phosphorus compound to form a salt insoluble in polyester, including lithium acetate, oxalate, benzoate, Organic carboxylates such as phthalates, stearates, borates, sulfates, and silicates.

Carbonates, inorganic acid salts such as monobicarbonate, halides such as chloride, chelate compounds such as ethylenediaminetetraacetic acid complex, hydroxides, oxides.

Alcoholades such as methylates, ethylates, glycolates, phenolates, etc. can be used. Organic carbo/acid salts, especially soluble in ethylene glycol,
A-genides, chelate compounds, and alcoholades are preferred, and organic carboxylates are particularly preferred. The above lithium compounds may be used alone or in combination of two or more.

When adding the above-mentioned phosphorus compound and lithium compound, the amount of phosphorus compound used and the use of wrinkle compound - It is necessary to specify the ratio of the amount of lithium compound used to the amount. That is, if the amount of the phosphorus compound used in the present invention is too small, the color depth of the final polyester fiber will be insufficient. tJ
) When K increases, the color depth no longer shows a significant improvement, and the abrasion resistance and durability deteriorate, and furthermore, it becomes difficult to obtain a polyester having a sufficient degree of polymerization and softening point.

Furthermore, trouble occurs in that yarn breakage occurs frequently during spinning. The amount of the phosphorus compound to be added should be in the range of O,S to 3 mol-0 with respect to the total acid components constituting the polyester, and preferably in the range of %411KO,S to 2 mol. If the total amount of metal equivalents contained in the phosphorus compound and the lithium compound is less than 10 times the amount of metal equivalents of the phosphorus compound, the depth of color of the obtained polyester fiber will be insufficient. The rate of superpolycondensation decreases, making it difficult to obtain a polyester with a high degree of polymerization, and the softening point of the resulting polyester decreases significantly. On the other hand, if this amount exceeds 3.2 times, coarse particles will be produced, and instead of improving the depth of color, the line-of-sight density will decrease. In this rounding, the total amount of metal equivalents of the phosphorus compound and lithium compound should be in the range of 2.0 to 3.2 times the number of moles of the II 177 compound, and %K 2 , a range of 0 to 3.0 times is preferred.

The above-mentioned isophthalic acid compound having an alkali metal sulfonate group, phosphorus compound, and lithium compound need to be added to the polyester reaction system without being reacted in advance. By doing so, the insoluble particles can be produced in the polyester in the form of uniform ultrafine particles. By reacting the inophthalic acid compound and/or phosphorus compound having the alkali metal sulfonate group with a lithium compound externally in advance to form insoluble particles and then adding them to the polyester reaction system, the dispersibility of the insoluble particles in the polyester can be improved. This results in poor rounding and coarse agglomerated particles, and the effect of improving the color depth of the final polyester fiber is no longer recognized.

The 0177 compound and the lithium compound can be added in any order at any stage until the synthesis of the polyester is completed. However, if only the phosphorus compound is added before the reaction in step 1111 is completed, the completion of the reaction in the first step may be inhibited.

If only the Mayu lithium compound is added before the end of the first-stage reaction, coarse particles will be generated during the esterification reaction, and coarse particles will be generated during the transesterification reaction. In this case, it is preferable to lower the temperature to below 20% by weight-S since this may proceed abnormally quickly and cause a bumping phenomenon. At least 80% by weight of lithium compound -
It is preferable that the total amount of the compound is added after the first stage of the reaction of polyester synthesis is substantially completed and after the ninth stage. In addition, if the phosphorus compound and lithium compound are added at a stage where the second stage reaction has progressed, particle aggregation and increase in size are likely to occur, resulting in poor color depth of the final polyester fiber. of the reaction mixture in a 12-step reaction because it tends to be sufficient.
Preferably, the time is before the Kuma viscosity reaches 0.3.

The above-mentioned isophthalic acid compound, phosphorus compound, and lithium compound having an alkali metal sulfonate group may be added all at once, added in two or more divided portions, or added continuously.

Some of the lithium compounds used in the present invention have the effect of suppressing the above-described by-product of ether bonds), and when such lithium compounds are used, it is not necessary to use a separate ether production inhibitor. This lithium compound can be added to the reaction initiation stage or during the first stage reaction to also serve as an ether production inhibitor.

As mentioned above, when the reaction is esterification, coarse particles may be generated, and when transesterification, bumping may occur, so the amount used is 20 qk by weight of the total amount of the lithium compound to be added. It is preferable to keep it below 30 degrees.

As explained above, specific amounts of the above-mentioned inophthalic acid compound and phosphorus compound having an alkali metal sulfonate group and a lithium compound in a specific amount ratio to the phosphorus compound are added to the polyester reaction system without reacting them in advance. In addition, by completing the synthesis of the polyester, it has a high degree of polymerization, a high softening point, and good passability through the spinning process, and finally has excellent color depth and friction durability. It is possible to obtain a polyester capable of imparting fibers.

It is not necessary to employ any special method to melt-spun the polyester thus obtained into fibers; any ordinary melt-spinning method for polyester fibers may be employed. Even if the fibers spun here are solid fibers without hollow parts.

It may be a hollow fiber having a hollow part. The outer shape and the shape of the hollow part in the cross section of the fiber to be spun may be one circular shape or four different shapes.

)! When spinning, the above-mentioned cationic dye-dyeable polyester to which the phosphorus compound and lithium compound are added, unmodified polyester without the addition, and/or cationic dye-dyeable polyester to which the phosphorus compound and lithium compound are not added are used. A core-sheath type compound fiber or two or more multi-layer side pie fibers using type polyester, adding a phosphorus compound and a lithium compound, and using a nine-cation dye dyeable type polyester as a sheath component or layer component.
It may also be a side-type double-barrel fiber.

In order to remove a part of the polyester fiber obtained in this way, it is necessary! This can be easily carried out by subjecting the fabric to an abrasive heat treatment or false twisting process, etc., or by further forming it into a fabric, and then treating it with an aqueous solution of an alkaline compound.

Examples of the alkali compound used here include sodium hydroxide, potassium hydroxide, tetramethylammonium hydroxide, sodium carbonate, potassium carbonate, and the like.

Among these, sodium hydroxide and potassium hydroxide are preferred.

The concentration of the aqueous solution of the alkaline compound varies depending on the type of alkaline compound, processing conditions, etc., but is usually LO1~
A range of 40 wt Is is preferred, and a range of %K O, 1 to 30 wt. The processing temperature is preferably in the range of room temperature to ZooC, and the photosensitive layer time is usually in the range of 1 minute to 4 hours.

The amount to be eluted and removed by the aqueous solution of this alkaline compound in step 11 is 2 parts by weight or more based on the weight of the fiber.
Should be ssc. By treating with an aqueous solution of an alkaline compound in this way, a large number of microvoids can be formed on the surface of the fibers and in the vicinity thereof, and dyeing
K is excellent so that it exhibits the depth of nine colors.

1 to 1 The polyester fiber obtained by the method of the present invention must contain optional additives, such as d catalyst, 2 coloring inhibitor, heat resistant agent, m flame agent, fluorescent whitening agent, matting agent, and 9 coloring agent. It may also contain agents.

Further explanation will be given below with reference to Examples. 1M! In the examples, "part" and "chi" indicate parts by weight and percent by weight, and the resulting polyester fibers were dyed to a deep O-color at the end of death.

Friction discoloration can be measured using the following method.

(1) Deepness of color As a measure of the depth of color, bathochromicity ('Ps) was used. This value increases the spectral reflectance (B) of the sample cloth
It was measured using an O-330 type self-recording spectrophotometer needle, and was determined from the Kubelkm-Munk equation shown below. The larger this value is, the greater the deep color effect is. (Measurement wavelength SOO density μ) Note that 8 indicates the absorption coefficient and 8 indicates the scattering coefficient.

(Spear) Using a Gakushin type flat abrasion machine for friction discoloration resistance and friction fastness testing, the test cloth was flattened a predetermined number of times under a load of 500 f, using a georgette made of polyethylene tereph PV-T xoo% as the friction cloth. After wear and tear, the degree of discoloration was determined using a gray scale for discoloration and fading. 1 for extremely low wear resistance
ml, and if it is extremely high, it is grade 5. For practical purposes, a level 4 or above is required.

′! J! Example 1 100 parts of dimethyl terephthalate, ethylene y-y-yl 1O! ll + 1 calcium acetate and 0.06 parts of water al were charged into a transesterification tank, and the temperature was raised from 140°C to 230"O over a period of 14 hours in a nitrogen gas atmosphere. The transesterification reaction was carried out while distilling the generated methanol out of the system. Subsequently, 0.64 parts of lithium acetate anhydrous salt (1.887 RUs relative to terephthal-dimethyl) was added to the resulting reaction product, and 1!KO, 5 sll of 1! I
I (0.69 mol relative to dimethyl terephthalate
%), and after another 5 minutes, 0.04 part of antimony trioxide 0
．． Add 04 parts and transfer to a polymerization can. Then, 4.8 parts of sodium 3,5-di(β-bitroxyethoxycarbonyl)benzenesulfonate (2.6 mol qk based on dimethyl terephthalate) was added to the polymerization kettle. Subsequently, the pressure was reduced from 760 mmHp to 1 mmHF't over 1 hour, and at the same time, the pressure was reduced from 230°C to 280''Of over 1 hour and 30 minutes.
The temperature was raised. Under reduced pressure below l mmHP, polymerization temperature g2
Polymerization was further carried out at 80°C for 2 hours and 30 minutes, for a total of 4 hours, to obtain a polymer having an intrinsic viscosity of 0.512° and a softening point of 258°C. After the reaction was completed, the polymer was made into chips according to a conventional method.

This chip was dried by a conventional method, 36 circular spinning holes with a hole vk of 0.3 were bored, and melt-spun at 290°C using a nine spinneret, and then stretched at a draw ratio of 3.5 times by a conventional method. A raw yarn of 75 denier/36 filaments was obtained.

This yarn has 8 twists of 250,077 m and 2 twists of 2,500 T/m.
The highly twisted yarn was then subjected to a steam treatment at 80° C. for 30 minutes to stop the twist.

The high-twist yarn has a warp density of 47 yarns/1. 8 with a latitude density of 32 lines/1.
A satin georgette fabric was woven with two strands arranged alternately. The obtained greige was subjected to a relaxing treatment at boiling temperature for 20 minutes using a rotary washer to create a grain.
After greasing in a conventional manner, the fabric was treated with a 1-aqueous sodium hydroxide solution at boiling temperature to obtain a fabric with a weight loss rate of 20 cm.

The fabric after this alkaline treatment is A11ea Cathil.
onBlack 0D-GLH (Hodogaya Chemical Product)
120 in a dyebath containing 2 V/g of Glauber's salt at 8% owf.
After dyeing with 'O for 66 minutes, soap the cloth according to the usual method to obtain a black cloth. This black cloth 0 color depth and wear 2
Table 1 shows the friction discoloration resistance of 00 times il.

In addition, cationic dyes such as Aigea Oatbiloo B
Change to lue CD-RLH! Dyeing was carried out using %owf to obtain a bright deep blue cloth. The clarity of the color of this blue cloth was determined by line of sight according to the following criteria and is listed in Table 1.

O Sharpness is significantly greater than the standard 0 Sharpness is greater than the standard ST Standard Δ Poor clarity compared to the standard × Sharpness is significantly inferior compared to the standard Example 2 Example Example 1 was carried out in the same manner as in Example 1, except that the amounts of lithium acetate anhydride and orthophosphoric acid used in Example I were changed. The results are shown in Table 1.

Example 3 The same procedure as in Example 1 was conducted except that the phosphorus compounds listed in Table 1 were added in the amounts listed in Table 1 in place of the Kusei phosphoric acid used in Example I.

There were nine results as shown in Table 1.

Example 4 In Example 1, S was added before the start of the polycondensation reaction,
Instead of 4.8 parts of sodium S-di(β-hydroxyethoxycarbonyl)benzenesulfonate, 4 parts of sodium 3.5-di(carbomethoxy)benzenesulfone was added before the start of the transesterification reaction, and After the completion of the reaction, 0.64 parts of lithium nine acetate anhydrous salt was added.
．． The same procedure as in Example 1 was carried out, except that 0.06 parts (0.177 mole based on dimethyl terephthalate) was added before the transesterification reaction, and the remaining 0.58 parts was added after the transesterification reaction was completed. The results are shown in the st table, 6 out of 9 out of 9.

Comparative Example 1 The lithium acetate anhydride used in Sou 11 was not used, and the amount of orthophosphoric acid added after completion of the transesterification was 0.04 parts (0.04 parts based on dimethyl terephthalate).
The same procedure as in Example 1 was carried out except that the amount was changed to 079 mol qb). The result was 9, as shown in No. 111.

Comparative Example 2 (Replacement of lithium nonacetate anhydrous salt O used in Example I)
The same procedure as in Example 1 was carried out except that 0.85 part of K-sujin calcium monohydrate (0.94 molti based on dimethyl terephthalate) was used.

The results are as shown in Table 1.

Patent applicant Teijin Ltd.

Claims (1)

[Scope of Claims] In the production of synthetic fibers made of polyester synthesized by the reaction of dicarboxylic acids, mainly terephthalic acid, or their ester-forming derivatives, and at least one glycol or their ester-forming derivatives, , at any stage until the synthesis of the drum polyester is completed, -) O, S ~ 10 mol based on the total acid component - to isophthalic acid or its ester-forming derivative having an alkali metal sulfonate group) Total acid component O, S ~ 3 mol - 〇 Following general formula (0) % formula % In formula 1, R1 and B1 are hydrogen atoms or -valent O] and horizontal 1
, X represents a water bulk atom, a -valent O organic group or a metal, and X represents O or 1. A phosphorus compound (c) represented by (m) @ , (b) and (c) C) without reacting the three in advance, and (1,) and (c) an association of 0 metal O Needle amount is LO~
Add it so that it becomes 3.2 times, and then add polyester O.
1. A method for producing synthetic fibers, which comprises completing the process, melt-spinning the obtained round positive ester, and eluting at least 2 parts by weight of the compound O*.