JP2004323829A - Easily alkali soluble copolyester - Google Patents

Easily alkali soluble copolyester Download PDF

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JP2004323829A
JP2004323829A JP2004074208A JP2004074208A JP2004323829A JP 2004323829 A JP2004323829 A JP 2004323829A JP 2004074208 A JP2004074208 A JP 2004074208A JP 2004074208 A JP2004074208 A JP 2004074208A JP 2004323829 A JP2004323829 A JP 2004323829A
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polymer
alkali
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soluble copolyester
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Seoung-Cheol Yang
セウング−チェオル ヤング
Yang-Kuk Son
ヤング−クック ソン
Ik-Hyeon Kwon
イク−ヒェオン クウォン
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Hyosung Corp
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/123—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
    • C08G63/127—Acids containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/16—Dicarboxylic acids and dihydroxy compounds
    • C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
    • C08G63/181—Acids containing aromatic rings
    • C08G63/183—Terephthalic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
    • C08G63/688—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
    • D01F6/62—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyesters

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  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Multicomponent Fibers (AREA)

Abstract

<P>PROBLEM TO BE SOLVED: To provide an easily alkali soluble copolyester condensate with 50-fold or faster reducing rate of alkali, a process for its production and a polyester conjugate fiber using the easily alkali soluble copolyester condensate. <P>SOLUTION: The production process of the easily alkali soluble copolyester condensate for conjugate fiber uses a batch system polymerization process using terephthalic acid as a raw material and adds 1-6 mole% of bishydroxyethyl isophthalate containing a metal sulfonate prepared by a reaction of a dimethyl isophthalate component containing the metal sulfonate and ethylene glycol to the dibasic acid components in the polymerized product. Then, 0.01-5 wt.% of an isophthalic acid component is added to a dibasic acid component in the polymerized product to cause an esterification reaction with 96% or over of esterification rate. The reaction product is transferred to a polycondensation reaction vessel to cause polymerization by adding 100-500 ppm of antimony trioxide to the polymerization product as a copolymerization reaction catalyst and 3-15 wt.% of a polyalkylene glycol ether with a molecular wt. of 1,000-20,000. <P>COPYRIGHT: (C)2005,JPO&NCIPI

Description

本発明は複合糸用アルカリ易溶性コポリエステル重合物に関し、より詳しくは優れたアルカリ溶出性を有し、紡糸の際、パック圧上昇が通常のポリエステルを類似していて作業性が優れており、又、溶融粘度が一般のポリエステルと類似していて超極細糸用原糸の機械的物性が一般のポリエステルと類似した原糸の製造を可能とするテレフタル酸重合工法を利用した複合糸用アルカリ易溶性コポリエステル重合物とその製造方法及びこれを利用したポリエステル複合繊維に関する。   The present invention relates to an alkali-soluble copolyester polymer for composite yarn, more specifically, has excellent alkali elution properties, and during spinning, the pack pressure rise is similar to that of ordinary polyester, and the workability is excellent, In addition, the alkali viscosity for composite yarns using a terephthalic acid polymerization method enables the production of yarns having a melt viscosity similar to that of ordinary polyesters and mechanical properties of yarns for ultra-fine yarns similar to ordinary polyesters. The present invention relates to a soluble copolyester polymer, a method for producing the same, and a polyester composite fiber using the same.

又、本発明は、アルカリの水溶液に対する溶解性を高めるために金属スルホネート塩を含有するビスヒドロキシエチルイソフタレート成分とポリアルキレンエーテルグリコールを共重合し、テレフタル酸のエステル反応率を高めるためにイソフタル酸成分を共重合して反応させる複合糸用アルカリ易溶性コポリエステル重合物とその製造方法及びこれを利用したポリエステル複合繊維に関する。   Further, the present invention provides a copolymer of a bishydroxyethyl isophthalate component containing a metal sulfonate salt and a polyalkylene ether glycol in order to increase the solubility of an alkali in an aqueous solution, and isophthalic acid in order to increase the ester reaction rate of terephthalic acid. The present invention relates to an alkali-soluble copolyester polymer for a composite yarn, in which components are copolymerized and reacted, a method for producing the same, and a polyester composite fiber using the same.

又、本発明は、極細糸の製造のための複合紡糸の際、溶融状態での溶融粘度が一般のポリエステルと似ていて超極細糸用原糸が一般のポリエステルと類似しているばかりでなく、溶融温度も高くて、仮撚と製編織等の作業性も優れた複合糸用アルカリ易溶性コポリエステル重合物とその製造方法及びこれを利用したポリエステル複合繊維に関する。   Further, the present invention is not only a composite spinning for the production of ultrafine yarn, the melt viscosity in the molten state is similar to general polyester, ultrafine yarn raw yarn is not only similar to general polyester, The present invention relates to an alkali-soluble copolyester polymer for composite yarns having a high melting temperature and excellent workability such as false twisting and weaving, a method for producing the same, and a polyester composite fiber using the same.

一般的に、アルカリの水溶液に対して溶出速度の速い重合物は、超極細糸用原糸を製造するのに多く使われており、アルカリの溶出の速い重合物及びその用途については、特許文献１、特許文献２、特許文献３等に記載されている。   Generally, a polymer having a high elution rate with respect to an aqueous alkali solution is often used for producing a raw yarn for ultra-fine yarn. 1, Patent Document 2, Patent Document 3, and the like.

しかし、特許文献１には、金属スルホネート含有ジメチルイソフタレート（以下、「ＤＭＳ」という）成分が全体酸成分に対して１〜５モル％、ポリアルキレンエーテルグリコールがコポリエステルに対して５〜２５重量％共重合されていると提示しているが、その詳しい製造方法については提示していない。又、その用途が複合糸ではなく単独繊維であるので、本発明の目的である極細糸用複合紡糸とは異なる。   However, Patent Document 1 discloses that a metal sulfonate-containing dimethyl isophthalate (hereinafter, referred to as “DMS”) component is 1 to 5 mol% based on the total acid component, and a polyalkylene ether glycol is 5 to 25% by weight based on the copolyester. % Copolymerized, but no detailed production method is given. Further, since the application is not a composite yarn but a single fiber, it is different from the composite spinning for ultrafine yarn which is the object of the present invention.

又、特許文献２には、その重合物の用途が本発明とは違うものの、金属スルホネート含有ジメチルイソフタレートの添加時、重合物の溶融粘度が高くなることを抑制するために、リン系の陰イオン性と陽イオン性の非反応性化合物を添加することにより、溶融粘度を下げる方法が提案されている。   Patent Document 2 discloses that, although the use of the polymer is different from that of the present invention, the addition of a metal sulfonate-containing dimethyl isophthalate suppresses the increase in the melt viscosity of the polymer. There has been proposed a method of lowering the melt viscosity by adding an ionic and cationic non-reactive compound.

そして、特許文献３には、金属スルホネート含有ジメチルイソフタレートと平均分子量１，０００〜１０，０００のポリアルキレングリコールを共重合した末端カルボン酸基の含有量が２５当量/トン以下である重合物が提案されている。この特許では、エステル化反応率８０〜９６％のオリゴマーになった時点で、金属スルホネート含有ジメチルイソフタレートを反応槽に添加し、その後にポリアルキレングリコールを投入する重合方法を提案している。   Patent Document 3 discloses a polymer in which the content of terminal carboxylic acid groups obtained by copolymerizing metal sulfonate-containing dimethyl isophthalate and polyalkylene glycol having an average molecular weight of 1,000 to 10,000 is 25 equivalents / ton or less. Proposed. This patent proposes a polymerization method in which a metal sulfonate-containing dimethyl isophthalate is added to a reaction vessel when an oligomer having an esterification reaction rate of 80 to 96% is obtained, and then a polyalkylene glycol is charged.

しかし、前記特許は連続重合法によるものであるため、金属スルホネート化合物がエステル反応槽に存在しないが、バッチ工法では金属スルホネート化合物がエステル反応槽にいつも存在するようになるので、エステル反応率を高めがたいという問題がある。   However, since the patent is based on the continuous polymerization method, the metal sulfonate compound does not exist in the ester reaction tank, but the metal sulfonate compound always exists in the ester reaction tank in the batch method, so that the ester reaction rate is increased. There is a problem that it is difficult.

又、前述した方法によって製造されたアルカリ溶出性重合物はＤＭＳの添加によって溶融粘度が急激に増加して高分子量の重合物を製造することが難しいので、特許文献４では、固有粘度０．２〜０．４の低粘度ポリマーを固相重合して願う分子量の重合物を製造する方法も提案している。   Further, the melt viscosity of the alkali-eluting polymer produced by the above-described method is rapidly increased by the addition of DMS, and it is difficult to produce a polymer having a high molecular weight. A method of producing a polymer having a desired molecular weight by solid-phase polymerization of a low-viscosity polymer of .about.0.4 has also been proposed.

しかし、これらの重合物には共通的にＤＭＳが共重合されているので、ジメチルテレフタレート（以下、「ＤＭＴ」という）を原料としてポリエステルを重合するＤＭＴ重合法では、同一の方式であるトランスエステル反応により反応が進行されて、未反応ＤＭＳ成分がほとんど残らない。しかし、ＤＭＴ重合法はテレフタル酸（以下、「ＴＰＡ」という）を原料とするＴＰＡ重合法と比べ、製造原価が高くなる短所がある。   However, since DMS is commonly copolymerized in these polymers, the DMT polymerization method for polymerizing polyester using dimethyl terephthalate (hereinafter referred to as “DMT”) as a raw material has the same transester reaction. , The reaction proceeds, and almost no unreacted DMS components remain. However, the DMT polymerization method has a disadvantage that the production cost is higher than the TPA polymerization method using terephthalic acid (hereinafter referred to as “TPA”) as a raw material.

前述したように、ＴＰＡを原料とするＴＰＡ重合法ではＤＭＳの反応が進行されないので、この未反応物によって紡糸の際パック圧上昇等の問題が発生するという短所を持っており、又、ＤＭＴ重合法とは違ってＴＰＡ重合法では未反応ＴＰＡが残存するようになるが、未反応ＴＰＡは未反応ＤＭＴとは違って溶融することもなく、又、オリゴマーやポリマーにも溶解しないので、オリゴマーフィルターやポリマーフィルターを通過しないまま残るので、これらと未反応ＤＭＳとの凝集によってオリゴマーのフィルター交換周期が短くなる等の問題が発生する。
特開平９−２９１４１８号公報 特開平８−９２８１９号公報 特開平１２−９５８５０号公報 特開昭５９−９３７２２号公報 韓国公開特許公報２００３−２４１９１号 As described above, in the TPA polymerization method using TPA as a raw material, since the reaction of DMS does not proceed, there is a disadvantage that a problem such as an increase in pack pressure during spinning occurs due to the unreacted product. Unlike the legal method, unreacted TPA remains in the TPA polymerization method. However, unlike unreacted DMT, unreacted TPA does not melt and does not dissolve in oligomers or polymers. And unreacted DMS, which remains without passing through the polymer filter, causing problems such as shortening the filter exchange cycle of the oligomer.
JP-A-9-291418 JP-A-8-92819 JP-A-12-95850 JP-A-59-93722 Korean Patent Publication No. 2003-24191

本発明は前述したような問題点を解決するためのもので、本発明の目的はＴＰＡ重合法を利用して製造原価の低いアルカリ易溶性コポリエステル重合物を製造し、オリゴマーフィルターの交換周期を増やして重合工程性を向上させることにより、一般ポリエステル重合物に比べ、アルカリの水溶液に対する溶出速度が５０倍以上速くて、溶融粘度が一般ポリエステル水準である複合糸用アルカリ易溶性コポリエステル重合物とその製造方法及びこれを使用したポリエステル複合繊維を提供することである。   An object of the present invention is to solve the above-described problems, and an object of the present invention is to produce an alkali-soluble copolyester polymer having a low production cost by using a TPA polymerization method and reduce the replacement cycle of an oligomer filter. By increasing the polymerization processability by increasing, compared to a general polyester polymer, the elution rate of an alkali in an aqueous solution is 50 times or more faster, and the melt viscosity is a general polyester level and an alkali-soluble copolyester polymer for a composite yarn. An object of the present invention is to provide a method for producing the same and a polyester composite fiber using the same.

本発明は、下記化学式１で代表される金属スルホネート塩を含有するビスヒドロキシエチルイソフタレート成分を重合物内の二酸（diacid）成分に対して１〜６モル％含み、下記化学式２で代表されるイソフタル酸成分を前記重合物内の二酸成分に対して０．０１〜５重量％、平均分子量１，０００〜２０，０００のポリアルキレンエーテルグリコールを重合物に対して３〜１５重量％含み、又、生成された重合物の溶融温度が２０５〜２４０℃で、固有粘度が０．５０〜０．７５ｄｌ/ｇであることを特徴とする複合糸用アルカリ易溶性コポリエステル重合物を提供する。   The present invention includes a bishydroxyethyl isophthalate component containing a metal sulfonate salt represented by the following chemical formula 1 in an amount of 1 to 6 mol% based on a diacid component in a polymer, and is represented by the following chemical formula 2. 0.01 to 5% by weight based on the diacid component in the polymer, and 3 to 15% by weight based on the polymer of a polyalkylene ether glycol having an average molecular weight of 1,000 to 20,000. Further, the present invention provides an alkali easily soluble copolyester polymer for composite yarn, wherein the produced polymer has a melting temperature of 205 to 240 ° C and an intrinsic viscosity of 0.50 to 0.75 dl / g. .

Figure 2004323829
Figure 2004323829

Figure 2004323829
Figure 2004323829

本発明は、前記化学式１で代表される金属スルホネート塩を含有するビスヒドロキシエチルイソフタレート成分を重合物内の二酸成分に対して１〜６モル％含み、前記化学式２で代表されるイソフタル酸成分を前記重合物内の二酸成分に対して０．０１〜５重量％、平均分子量１，０００〜２０，０００のポリアルキレンエーテルグリコールを重合物に対して３〜１５重量％含み、又、生成された重合物の溶融温度が２０５〜２４０℃で、固有粘度が０．５０〜０．７５ｄｌ/ｇであるアルカリ易溶性コポリエステル重合物と、通常のポリエステル重合物を利用して複合紡糸して製造することを特徴とするポリエステル複合繊維を提供する。   The present invention provides a bishydroxyethyl isophthalate component containing a metal sulfonate salt represented by Chemical Formula 1 in an amount of 1 to 6 mol% based on a diacid component in a polymer, and isophthalic acid represented by Chemical Formula 2 The components are 0.01 to 5% by weight based on the diacid component in the polymer, and 3 to 15% by weight based on the polymer of a polyalkylene ether glycol having an average molecular weight of 1,000 to 20,000; Composite spinning is performed using the alkali-soluble copolyester polymer having a melting temperature of 205 to 240 ° C and an intrinsic viscosity of 0.50 to 0.75 dl / g, and a normal polyester polymer. The present invention provides a polyester composite fiber characterized by being manufactured by:

本発明は、前記化学式１で代表される金属スルホネート塩を含有するビスヒドロキシエチルイソフタレート成分を、重合の際、重合物内の二酸成分に対して１〜６モル％投入し、前記記化学式２で代表されるイソフタル酸成分を重合物内の二酸成分に対して０．０１〜５重量％、平均分子量１，０００〜２０，０００のポリアルキレンエーテルグリコールを重合物に対して３〜１５重量％投入して製造することを特徴とする複合糸用アルカリ易溶性コポリエステル重合物の製造方法を提供する。   According to the present invention, a bishydroxyethyl isophthalate component containing a metal sulfonate salt represented by the above-mentioned chemical formula 1 is charged at 1 to 6 mol% with respect to a diacid component in a polymer at the time of polymerization. The isophthalic acid component represented by No. 2 is 0.01 to 5% by weight based on the diacid component in the polymer, and the polyalkylene ether glycol having an average molecular weight of 1,000 to 20,000 is 3 to 15% based on the polymer. Provided is a method for producing an alkali-soluble copolyester polymer for a composite yarn, characterized in that the production is carried out by adding the compound by weight.

前記した複合糸用アルカリ易溶性コポリエステル重合物の製造方法は、テレフタル酸を主原料とするＴＰＡ重合法によって製造することを特徴とする。   The method for producing the alkali-soluble copolyester polymer for composite yarn described above is characterized in that it is produced by a TPA polymerization method using terephthalic acid as a main raw material.

本発明のコポリエステルは未反応物の含有量が低いので、パック圧上昇の速度が低く、一般ポリエステル重合物と比べ、アルカリの溶出速度が５０倍以上速く、又、溶融粘度が一般ポリエステル水準である重合物を提供することができる。   Since the copolyester of the present invention has a low content of unreacted substances, the rate of increase in pack pressure is low, the alkali elution rate is 50 times or more faster than that of a general polyester polymer, and the melt viscosity is at the level of a general polyester. Certain polymers can be provided.

又、本発明によるコポリエステルの製造方法はその製造過程が容易であり、又、物性が均一である重合物を製造することを可能とし、安定した作業性と物性及び均一なアルカリ溶出性を有する複合糸を製造することができる。   Further, the process for producing a copolyester according to the present invention is easy in its production process, and also enables to produce a polymer having uniform physical properties, and has stable workability, physical properties and uniform alkali dissolution. Composite yarns can be manufactured.

以下、本発明をより詳しく説明する。   Hereinafter, the present invention will be described in more detail.

本発明では、ＤＭＳの代わりに金属スルホネート基含有ビスヒドロキシエチルイソフタレート（下記化学式１、以下、「ＤＥＳ」という）を使用する。   In the present invention, metal sulfonate group-containing bishydroxyethyl isophthalate (the following chemical formula 1, hereinafter referred to as “DES”) is used instead of DMS.

ＤＭＳはＴＰＡ重合法でエチレングリコール（以下、「ＥＧ」という）との反応性が低いため、ＤＭＳ状態に維持されてパック圧上昇の原因となる。従って、本発明ではＤＭＳをＥＧとは別に反応させた、下記化学式１の構造を有する金属スルホネート基含有ビスヒドロキシエチルイソフタレート（以下、「ＤＥＳ」という）を原料として使用した。   DMS is low in reactivity with ethylene glycol (hereinafter, referred to as “EG”) in the TPA polymerization method, so that DMS is maintained in a DMS state and causes an increase in pack pressure. Therefore, in the present invention, a metal sulfonate group-containing bishydroxyethyl isophthalate (hereinafter, referred to as “DES”) having a structure represented by the following chemical formula 1 in which DMS is reacted separately from EG is used as a raw material.

Figure 2004323829
Figure 2004323829

但し、Ｍはアルカリ金属で、Ｎａ，Ｌｉ，Ｋ等を示す。   Here, M is an alkali metal, such as Na, Li, and K.

工業的にＤＥＳを製造する方法については、特許文献５に提示されている。   A method for industrially producing DES is disclosed in Patent Document 5.

化学式１で示されるＤＥＳの重合物内の含有量は全二酸成分に対して１．５〜６．０モル％が好ましい。ＤＥＳの含有量が１．５モル％未満であると、重合物のアルカリ溶液に対する溶出性が低くなり、超極細糸用アルカリ易溶性ポリエステル重合物としての価値がないので好ましくない。ＤＥＳの含有量が６．０モル％を超えると、溶融粘度が高くなって紡糸性が落ち、又、高重合度の重合物を得がたいという問題が生じ、重合物の溶融温度があまりにも低くなるので仮撚等の工程上の問題が発生する。   The content of the DES represented by the chemical formula 1 in the polymer is preferably 1.5 to 6.0 mol% based on all diacid components. If the content of DES is less than 1.5 mol%, the dissolution of the polymer in an alkali solution becomes low, and the value is not preferred as an alkali-soluble polyester polymer for ultrafine yarn. When the content of DES exceeds 6.0 mol%, the melt viscosity becomes high and the spinnability decreases, and a problem arises in that it is difficult to obtain a polymer having a high degree of polymerization, and the melting temperature of the polymer becomes too low. Therefore, problems in the process such as false twisting occur.

又、本発明で使用されたポリアルキレンエーテルグリコール（以下、「ＰＡＧ」という）は下記化学式３で代表される原料を使用した。   The polyalkylene ether glycol (hereinafter, referred to as “PAG”) used in the present invention used a raw material represented by the following chemical formula 3.

Ｈ｛−Ｏ（ＣＨ2）m｝n−ＯＨ・・・（３） H ｛—O (CH 2 ) m ｝ n— OH (3)

但し、ｍは１〜４の整数で、ｎは２以上の整数であり、その重合度はポリアルキレンエーテルグリコールの分子量によって異なる。本発明の実施例ではｍが２であるポリエチレンエーテルグリコール（以下、「ＰＥＧ」という）を使用した。   Here, m is an integer of 1 to 4, n is an integer of 2 or more, and the degree of polymerization differs depending on the molecular weight of the polyalkylene ether glycol. In the embodiment of the present invention, polyethylene ether glycol having m = 2 (hereinafter referred to as “PEG”) was used.

ＰＡＧの重合物内の含有量は重合物に対して３〜１５重量％が好ましい。ＰＡＧの含有量が３重量％未満であると、アルカリ水溶液に対する溶出性が低くなって超極細糸の製造が難しいばかりでなく、又、溶出性を高めるためにはＤＥＳの含有量を高めなければならないので、この場合、再び高重合度の重合物を得がたいという問題が持続的に発生する。又、ＰＡＧの含有量が１５重量％を超える場合には、重合物の溶融温度があまりにも低くなり、又、ＰＡＧの耐熱性が低下されるので、品質管理に問題が生じる。又、泡(foam)が大量に発生するので、重合工程の管理が難しくなる問題が発生するので好ましくない。   The content of PAG in the polymer is preferably 3 to 15% by weight based on the polymer. When the content of PAG is less than 3% by weight, the dissolution property to an alkaline aqueous solution is low, so that not only is it difficult to produce a superfine thread, but also to increase the dissolution property, the DES content must be increased. In this case, the problem that it is difficult to obtain a polymer having a high polymerization degree continuously occurs in this case. On the other hand, if the content of PAG exceeds 15% by weight, the melting temperature of the polymer becomes too low, and the heat resistance of PAG is reduced, so that there is a problem in quality control. Further, since a large amount of foam is generated, a problem that management of the polymerization step becomes difficult occurs, which is not preferable.

そして、本発明ではテレフタル酸のエステル反応率を高めるために、下記化学式２で代表されるイソフタレート成分を使用した。   In the present invention, an isophthalate component represented by the following chemical formula 2 was used to increase the ester reaction rate of terephthalic acid.

Figure 2004323829
Figure 2004323829

但し、ＲはＨ（イソフタル酸）又はＣＨ3等のアルキル基（ＣＨ3である場合は、ジメチルイソフタレートになる）である。 Here, R is (if it is CH 3, dimethyl isophthalate become phthalate) alkyl group such as H (isophthalic acid) or CH 3 is.

化学式２で示されるイソフタル酸成分をテレフタル酸と比べると、分子量と性状は同一であるが、反応性が非常に高い。ハメット法則(Hammet Rule)によってパラ位置のテレフタル酸よりメタ位置のイソフタル酸の方が反応性が高い。本発明ではテレフタル酸を主原料とするＴＰＡ工法を使用するので、ＲがＨであるイソフタル酸を使用した。   When the isophthalic acid component represented by the chemical formula 2 is compared with terephthalic acid, the molecular weight and properties are the same, but the reactivity is very high. According to Hammett's rule, isophthalic acid in meta position is more reactive than terephthalic acid in para position. In the present invention, since the TPA method using terephthalic acid as a main raw material is used, isophthalic acid in which R is H is used.

イソフタル酸の含有量は二酸成分に対して０．０１〜５重量％が好ましいが、これはこの範囲の含有量が重合処方によって９７％以上のエステル反応率を示す含有量であり、オリゴマーフィルターの交換周期が良好であるためである。本発明でのイソフタル酸の役割はテレフタル酸の反応率を高めることであるので、その含有量は低ければ低いほどいい。イソフタル酸の含有量が５重量％を超えると、製造されるコポリエステルの融点があまりにも低くなるので、複合繊維の形成の際、仮撚で融着が発生する等の問題が発生する。又、イソフタル酸の含有量が０．０１重量％未満であると、エステル反応率があまりにも低くて未反応ＴＰＡの含有量が増加するので、これらが化学式１の製造過程の中で完全に反応していない金属スルホネート含有ジメチルイソフタレートと凝集物を形成して、重合工程性が低下するので好ましくない。   The content of isophthalic acid is preferably 0.01 to 5% by weight with respect to the diacid component. This content is such that the content of ester in this range shows 97% or more of the ester reaction rate depending on the polymerization recipe. This is because the replacement cycle of the is good. Since the role of isophthalic acid in the present invention is to increase the conversion of terephthalic acid, the lower the content, the better. When the content of isophthalic acid exceeds 5% by weight, the melting point of the copolyester to be produced is too low, so that problems such as fusion occurring in false twist during formation of the conjugate fiber occur. On the other hand, if the content of isophthalic acid is less than 0.01% by weight, the ester conversion is too low and the content of unreacted TPA increases. It is not preferable because it forms an aggregate with dimethyl isophthalate containing metal sulfonate which has not been formed, thereby lowering the polymerization processability.

アルカリ易溶性コポリエステル重合物の溶出に直接的に影響を及ぼすＤＥＳとＰＡＧの含有量は、ＤＥＳの全二酸成分に対するモル％をＭ（Ｄ）とし、ＰＡＧ重合物に対する重量％をＷ（Ｐ）とすると、Ｍ（Ｄ）とＷ（Ｐ）の和は４〜２１であることが好ましい。   The content of DES and PAG which directly affects the dissolution of the alkali-soluble copolyester polymer is represented by M (D) where mol% is based on the total diacid component of DES, and W (P) is the weight% based on the PAG polymer. ), The sum of M (D) and W (P) is preferably 4 to 21.

即ち、４≦Ｍ（Ｄ）＋Ｗ（Ｐ）≦２１の範囲であることが好ましい。   That is, it is preferable that 4 ≦ M (D) + W (P) ≦ 21.

この和が４未満であると、アルカリ水溶液の中での溶出が不十分になるので、分割がされないおそれがある。   If the sum is less than 4, elution in an aqueous alkaline solution becomes insufficient, and there is a possibility that the separation is not performed.

そして、この和が２１を超えると、重合物の融点があまりにも低くなるので、製糸性等が落ちり、又、製造費用の上昇が高くなりすぎるので好ましくない。   If the sum exceeds 21, the melting point of the polymer becomes too low, so that the spinnability and the like are lowered, and the production cost is undesirably increased.

重合物の溶融温度（以下、「Ｔm」という）は２０５〜２４０℃が好ましい。重合物の溶融温度が２０５℃より低いと、紡糸温度をひどく低めなければならないという問題ばかりでなく、後工程性が悪くなり、又、通常の紡糸温度で紡糸した場合、熱分解が大きくなりすぎるという問題が発生する。そして、本発明のよる組成では、溶融温度が２４０℃より高い重合物を製造することは不可能であるばかりでなく、それが可能であるとしても、紡糸温度を高めなければならないので、熱分解の問題が発生し、本発明の目的には符合しない。 The melting temperature (hereinafter, referred to as “T m ”) of the polymer is preferably from 205 to 240 ° C. When the melting temperature of the polymer is lower than 205 ° C., not only the problem that the spinning temperature must be significantly lowered, but also the post-processability deteriorates, and when spinning at a normal spinning temperature, thermal decomposition becomes too large. The problem occurs. With the composition according to the present invention, it is not only impossible to produce a polymer having a melting temperature higher than 240 ° C., but even if it is possible, the spinning temperature must be increased, so that the thermal decomposition This problem does not meet the purpose of the present invention.

重合物の固有粘度は０．５０〜０．７５ｄｌ/ｇであることが好ましい。固有粘度が低ければ低いほど、重合物の溶出には有利になるが、あまりにも低いと溶融粘度が低くなりすぎる傾向がある。固有粘度が０．５０ｄｌ/ｇ未満であると、重合物の粘度があまりにも低いので、重合後、排出時にペレット化が難しくなるか、又は、紡糸の際、溶融粘度があまりにも低くて曲糸が生じやすい。固有粘度が０．７５ｄｌ/ｇを超えると、溶融粘度が高すぎてこれによって紡糸温度を高めなければならなく、紡糸温度を高めると熱分解等の問題が発生しやすいので好ましくない。   The intrinsic viscosity of the polymer is preferably 0.50 to 0.75 dl / g. The lower the intrinsic viscosity, the more advantageous is the elution of the polymer, but if it is too low, the melt viscosity tends to be too low. When the intrinsic viscosity is less than 0.50 dl / g, the viscosity of the polymer is too low, so that pelletization becomes difficult at the time of discharge after polymerization, or the melt viscosity is too low at the time of spinning to obtain a curved yarn. Tends to occur. If the intrinsic viscosity is more than 0.75 dl / g, the melt viscosity is too high, and the spinning temperature must be increased, and if the spinning temperature is increased, problems such as thermal decomposition are likely to occur.

本発明で用いられるその他の原料について説明する。   Other raw materials used in the present invention will be described.

ＤＥＳはＴＰＡとＥＧが反応する直接エステル化反応（Direct Esterification Reaction、以下、「ＤＥ反応」という）のどの段階で投入してもかまわないが、反応の容易性及び均一性のために、本発明者らはＴＰＡとＥＧでスラリーを製造する工程に投入した。   DES may be added at any stage of the direct esterification reaction (hereinafter referred to as “DE reaction”) in which TPA and EG react. However, the DES of the present invention is preferred because of its easiness and uniformity. They have put them into the process of producing a slurry with TPA and EG.

ポリアルキレンエーテルグリコールは重合運転の問題がなければ、反応中のどの時点に投入しても問題はない。しかし、本発明によるＴＰＡ重合法によっては、エステル化反応槽の液面高さがスラリーが流入されることにより高くなるので、ＰＡＧをエステル化反応槽に投入すると、ＰＡＧ泡(foam)の生成による液面の上昇が、同じ反応槽での生産性を低下させる問題が発生するおそれがある。又、重縮合反応槽に投入すると、真空をかけてやる過程でポリエステルオリゴマーとの相溶性がよくないＰＡＧが真空界へ吸い込まれて真空界が詰まってしまう問題が発生するおそれがある。従って、本発明者らはいくつかの実験を行った結果、エステル化反応を終えた後、ポリエステルオリゴマーを重縮合反応槽（Polycondensation Reactor、以下、「ＰＣ反応槽」という）へ移送した後、ＰＡＧを投入し、その後、真空をゆっくり加えることにより真空界を調節して飛散を最小化する方法を選んだ。   There is no problem if the polyalkylene ether glycol is introduced at any time during the reaction, as long as there is no problem in the polymerization operation. However, according to the TPA polymerization method according to the present invention, the liquid level in the esterification reaction tank is increased by the flow of the slurry. Therefore, when the PAG is charged into the esterification reaction tank, PAG foam is generated. There is a possibility that a problem that the rise in the liquid level lowers the productivity in the same reaction tank may occur. In addition, when charged into a polycondensation reaction tank, there is a possibility that PAG, which has poor compatibility with the polyester oligomer, is sucked into the vacuum field in the process of applying a vacuum and the vacuum field is clogged. Therefore, the present inventors conducted some experiments and found that after the esterification reaction was completed, the polyester oligomer was transferred to a polycondensation reactor (hereinafter, referred to as “PC reactor”), and then the PAG was transferred. Then, a method of adjusting the vacuum field by slowly applying a vacuum to minimize scattering was selected.

又、エステル化反応率を高めるために投入するイソフタル酸は、当然にエステル化反応槽に投入するが、その方法としては、スラリーが投入される前に先に投入する方法、又はスラリーの製造の際にＴＰＡと一緒に投入する方法がある。本発明者らは運転の容易性のために、ＴＰＡと一緒にスラリーに投入する方法を選んだ。   Also, isophthalic acid to be charged to increase the esterification reaction rate is naturally charged to the esterification reaction tank. As a method, a method of charging the slurry first before the slurry is charged, or a method of manufacturing the slurry. At that time, there is a method of feeding together with TPA. We chose the method of dosing the slurry with TPA for ease of operation.

本発明によるアルカリ易溶性コポリエステル重合物は、耐熱性が弱いＰＡＧを含んでいて、高温での熱安定性が弱まるので、これを防止するために安定剤を使用することができる。安定剤としてはリン系の安定剤と、フェノール系、アミン系の安定剤を効果的に使用することができる。リン系の安定剤としては、トリメチルフォスフェート、トリフェニルフォスフェート等のフォスフェート系と、トリフェニルフォスファート等のフォスファート、トリフェニルフォスフィン等のフォスフィン系の化合物を使用することができ、フェノール系の安定剤としてはチバガイギ社のイガノックス（Ｉｒｇａｎｏｘ）シリーズ等を、アミン系としてはチバガイギ社のチヌヴィン（Ｔｉｎｕｖｉｎ）シリーズ等のハルス（ＨＡＬＳ，Hindered Amine Light Stabilizer）等を使用することができる。   Since the alkali-soluble copolyester polymer according to the present invention contains PAG having low heat resistance and low thermal stability at high temperatures, a stabilizer can be used to prevent this. As the stabilizer, a phosphorus-based stabilizer and a phenol-based or amine-based stabilizer can be used effectively. Examples of the phosphorus-based stabilizer include phosphate-based compounds such as trimethyl phosphate and triphenyl phosphate, and phosphate-based compounds such as triphenyl phosphate and phosphine-based compounds such as triphenyl phosphine. Examples of the stabilizer include Irganox series manufactured by Ciba-Geigy Corporation, and examples of amine-based stabilizers include HALS (Hindered Amine Light Stabilizer) such as Tinuvin series manufactured by Ciba-Geigy Corporation.

反応によって製造された重合物の物性は下記の方法で分析した。   The physical properties of the polymer produced by the reaction were analyzed by the following methods.

１．テレフタル酸のエステル反応率：エステル反応されたオリゴマーを利用してカルボン酸の濃度を滴定して計算した。   1. Ester conversion of terephthalic acid: The carboxylic acid concentration was calculated by titrating the ester-reacted oligomer.

２．重合物の減量速度：ペレット状態の重合物を液体窒素を利用して破砕した後、９５℃の１．２重量％ＮａＯＨ水溶液を利用して１０分間処理して残っている重合物をこして、処理前後の重量で計算した。   2. Weight loss rate of polymer: After crushing the polymer in a pellet state using liquid nitrogen, treating with a 1.2% by weight aqueous solution of NaOH at 95 ° C. for 10 minutes to rub the remaining polymer, Calculated by weight before and after treatment.

３．固有粘度(Intrinsic Viscosity)：フェノールと１，１，２，２−テトラクロロエタンが６：４の重量比で混ざっている溶液に重合物を溶かして、３０℃の恒温槽でウベロデ管を利用して測定した。   3. Intrinsic Viscosity: Dissolve the polymer in a solution in which phenol and 1,1,2,2-tetrachloroethane are mixed at a weight ratio of 6: 4, and use a Uberode tube in a thermostat at 30 ° C. It was measured.

４．溶融温度：Ｐｅｒｋｉｎ Ｅｌｍｅｒ社のＤＳＣ ７(Differential Scanning Calorimetry)を利用して１０℃/分に乗温して、溶融範囲内のピックで分析した。   4. Melting temperature: Using a DSC 7 (Differential Scanning Calorimetry) of Perkin Elmer, the temperature was raised to 10 ° C./min, and analysis was performed using a pick within the melting range.

５．溶融粘度：製造された重合物を真空乾燥機で１２０℃で１２時間乾燥した後、ＴＯＹＯＳＥＩ社の１Ｂを利用して、２８５℃でＳｈｅａｒ Ｒａｔｅ ６０８での粘度をポイズ（ｐｏｉｓｅ）で示して比べた。   5. Melt viscosity: The polymer was dried at 120 ° C. for 12 hours using a vacuum drier, and the viscosity was measured by using Shear Rate 608 at 285 ° C. by poise using TOYOSEI 1B. .

６．仮撚作業性：紡糸された部分配向糸でムラタ仮撚機を利用して仮撚作業を実施して、１６０ｍの原糸に３個以上の毛羽がある場合を×、１６０ｍの原糸に毛羽が１〜２個見える場合を○、ない場合を◎で表示した。   6. False twisting workability: A false twisting operation is performed on the spun partially oriented yarn using a Murata false twisting machine, and when there are three or more fluffs in the 160 m original yarn, the fluff is applied to the 160 m original yarn. Is shown as 場合 when one or two are visible, and as ◎ when no.

７．原糸の減量率：製造された原糸をニッチング(knitting)して１．２％ＮａＯＨ溶液で溶出した後、原糸の断面を視差走査顕微鏡(Scanning Differential Microscopy、以下、「ＳＥＭ」という)で分析して一般ＰＥＴ部分以外に残りの部分が残っているかを確認した。   7. Reduction rate of yarn: After knitting the manufactured yarn and eluting it with a 1.2% NaOH solution, the cross section of the yarn is scanned with a parallax scanning microscope (Scanning Differential Microscopy, hereinafter referred to as “SEM”). The analysis was performed to confirm whether the remaining portion other than the general PET portion remained.

以下、実施例で本発明をより詳しく説明する。しかし、本実施例によって本発明の範囲が制限されるものではない。   Hereinafter, the present invention will be described in more detail with reference to Examples. However, the scope of the present invention is not limited by the present embodiment.

（実施例１）
化学式１で代表されるＤＥＳの中でＭがＮａである物質を使用した（分子量３５６．２８で、３５重量％の濃度でＥＧに溶解されている状態である）。 (Example 1)
In DES represented by Chemical Formula 1, a substance in which M is Na was used (having a molecular weight of 356.28 and being dissolved in EG at a concentration of 35% by weight).

ＴＰＡとイソフタル酸（以下、「ＩＰＡ」という）とＭがＮａであるＤＥＳ、ＥＧを使用して、ＥＧ/（ＴＰＡ＋ＩＰＡ＋ＤＥＳ）のモル比が１．１２、ＤＥＳ/（ＴＰＡ＋ＩＰＡ＋ＤＥＳ）モル比が４．０％、ＰＥＧを５重量％投入することを勘案して重合物に対して１重量％のＩＰＡとなるようにしてスラリーを調剤した。   Using TPA, isophthalic acid (hereinafter referred to as “IPA”) and DES or EG in which M is Na, the molar ratio of EG / (TPA + IPA + DES) is 1.12, and the molar ratio of DES / (TPA + IPA + DES) is 4.0. % And PEG was added in an amount of 1% by weight with respect to the polymer in consideration of the addition of 5% by weight of the PEG.

ＤＥ反応槽にはＭがＮａであるＤＥＳ含有量が２．２モル％で、ＩＰＡが重合物に対して１重量％含有されたオリゴマーが２５５℃を維持しながら攪拌されている。   In the DE reactor, an oligomer containing DES containing 2.2 mol% of M and Na and containing 1% by weight of IPA with respect to the polymer is stirred while maintaining 255 ° C.

反応機の内温が２５５℃に上昇した時点からスラリーを投入しはじめ、スラリーの投入が完了した後、３０分間攪拌を持続した。この際のエステル反応機内部のエステル化反応率は９７．２％であった。   At the time when the internal temperature of the reactor increased to 255 ° C., the slurry was started to be charged, and after the slurry was charged, stirring was continued for 30 minutes. At this time, the esterification reaction rate inside the ester reactor was 97.2%.

製造されたオリゴマーを３８μｍの空隙を有するフィルターを通過させて、重縮合反応槽へ移送して、触媒としてアンチモントリオキサイドを重合物に対して３００ｐｐｍ、安定剤としてリン酸を重合物に対して３００ｐｐｍ、分子量４，０００のポリエチレングリコールを重合物に対して５重量％投入した後、５００ｔｏｒｒで３０分間反応させた。その後、高真空で２００分間反応させた後、真空破壊して重合物を排出した。排出された重合物の固有粘度は０．５５ｄｌ/ｇで、溶融温度は２２０℃であった。   The produced oligomer was passed through a filter having a gap of 38 μm, and transferred to a polycondensation reaction tank. Antimony trioxide was used as a catalyst at 300 ppm for the polymer, and phosphoric acid was used as a stabilizer at 300 ppm for the polymer. After adding 5% by weight of polyethylene glycol having a molecular weight of 4,000 to the polymer, the mixture was reacted at 500 torr for 30 minutes. Then, after reacting for 200 minutes under high vacuum, the polymer was discharged by breaking in vacuum. The intrinsic viscosity of the discharged polymer was 0.55 dl / g, and the melting temperature was 220 ° C.

製造された重合物と一般ポリエステル重合物を利用して３７個の島成分を有するアルカリ易溶性重合物と消光剤としてＴｉＯ2を０．３重量％含有する固有粘度０．６３ｄｌ/ｇの一般ポリエステル重合物との複合比が３０：７０である海島型複合糸(Sea and Island Conjugate Fiber)１２０デニール/３６フィラメントの部分配向糸を製造した後、ムラタ仮撚機を利用して仮撚を実施し、７５デニール/３６フィラメントの仮撚糸を製造した。分析した結果を表１に示した。 Utilizing the produced polymer and the general polyester polymer, an alkali-soluble polymer having 37 island components and a general polyester having an intrinsic viscosity of 0.63 dl / g containing 0.3% by weight of TiO 2 as a quencher After producing a partially oriented yarn of 120 denier / 36 filaments having a composite ratio of 30:70 with the polymer, the false twist was carried out using a Murata false twister. , 75 denier / 36 filament false twisted yarn was produced. The results of the analysis are shown in Table 1.

（比較例１）
ＭがＮａであるＤＥＳを７モル％投入したこと以外は、実施例１と同一に実施し、その結果を表１に示した。 (Comparative Example 1)
The same operation as in Example 1 was carried out except that 7 mol% of DES in which M was Na was used, and the results are shown in Table 1.

（実施例２）
ＩＰＡを重合物に対して３重量％投入したこと以外は、実施例１と同一に実施し、その結果を表１に示した。 (Example 2)
The procedure was the same as in Example 1, except that IPA was added in an amount of 3% by weight based on the amount of the polymer, and the results are shown in Table 1.

（比較例２）
ＩＰＡを重合物に対して７重量％投入したこと以外は、実施例１と同一に実施し、その結果を表１に示した。 (Comparative Example 2)
The same operation as in Example 1 was carried out except that IPA was added in an amount of 7% by weight based on the amount of the polymer, and the results are shown in Table 1.

（比較例３）
分子量４，０００のポリエチレングリコールを重合物に対して１７重量％投入したこと以外は、実施例１と同一に実施し、その結果を表１に示した。 (Comparative Example 3)
The same operation as in Example 1 was carried out except that 17% by weight of polyethylene glycol having a molecular weight of 4,000 was added to the polymer, and the results are shown in Table 1.

（比較例４）
実施例１の重合物を利用して２００℃で真空を利用して固相重合を実施し、固有粘度０．８３ｄｌ/ｇの重合物を製造した。それを用いて繊維を製造し、その結果を表１に示した。 (Comparative Example 4)
Solid-state polymerization was performed using the polymer of Example 1 at 200 ° C. using a vacuum to produce a polymer having an intrinsic viscosity of 0.83 dl / g. Fibers were produced using the same, and the results are shown in Table 1.

Figure 2004323829
Figure 2004323829

Claims (4)

下記化学式１で代表される金属スルホネート塩を含有するビスヒドロキシエチルイソフタレート成分を重合物内の二酸成分に対して１〜６モル％含み、下記化学式２で代表されるイソフタル酸成分を前記重合物内の二酸成分に対して０．０１〜５重量％、平均分子量１，０００〜２０，０００のポリアルキレンエーテルグリコールを重合物に対して３〜１５重量％含み、又、生成された重合物の溶融温度が２０５〜２４０℃で、固有粘度が０．５０〜０．７５ｄｌ/ｇであることを特徴とする複合糸用アルカリ易溶性コポリエステル重合物。
Figure 2004323829
Figure 2004323829
 A bishydroxyethyl isophthalate component containing a metal sulfonate salt represented by the following chemical formula 1 is contained in an amount of 1 to 6 mol% based on a diacid component in the polymer, and an isophthalic acid component represented by the following chemical formula 2 is polymerized. The polyalkylene ether glycol having an average molecular weight of 1,000 to 20,000 is contained in an amount of 3 to 15% by weight based on the weight of the polymer, An alkali-soluble copolyester polymer for composite yarns, wherein the melt temperature of the product is 205 to 240 ° C and the intrinsic viscosity is 0.50 to 0.75 dl / g.
Figure 2004323829
Figure 2004323829
 下記化学式１で代表される金属スルホネート塩を含有するビスヒドロキシエチルイソフタレート成分を重合物内の二酸成分に対して１〜６モル％含み、下記化学式２で代表されるイソフタル酸成分を前記重合物内の二酸成分に対して０．０１〜５重量％、平均分子量１，０００〜２０，０００のポリアルキレンエーテルグリコールを重合物に対して３〜１５重量％含み、又、生成された重合物の溶融温度が２０５〜２４０℃で、固有粘度が０．５０〜０．７５ｄｌ/ｇであるアルカリ易溶性コポリエステル重合物と、通常のポリエステル重合物を利用して複合紡糸して製造することを特徴とするポリエステル複合繊維。
Figure 2004323829
Figure 2004323829
 A bishydroxyethyl isophthalate component containing a metal sulfonate salt represented by the following chemical formula 1 is contained in an amount of 1 to 6 mol% based on a diacid component in the polymer, and an isophthalic acid component represented by the following chemical formula 2 is polymerized. The polyalkylene ether glycol having an average molecular weight of 1,000 to 20,000 is contained in an amount of 3 to 15% by weight with respect to the polymer, The product is produced by compound spinning using an alkali-soluble copolyester polymer having a melting temperature of 205 to 240 ° C and an intrinsic viscosity of 0.50 to 0.75 dl / g, and a normal polyester polymer. Polyester composite fiber characterized by the above.
Figure 2004323829
Figure 2004323829
 下記化学式１で代表される金属スルホネート塩を含有するビスヒドロキシエチルイソフタレート成分を、重合の際、重合物内の二酸成分に対して１〜６モル％投入し、下記化学式２で代表されるイソフタル酸成分を重合物内の二酸成分に対して０．０１〜５重量％、平均分子量１，０００〜２０，０００のポリアルキレンエーテルグリコールを重合物に対して３〜１５重量％投入して製造することを特徴とする複合糸用アルカリ易溶性コポリエステル重合物の製造方法。
Figure 2004323829
Figure 2004323829
 At the time of polymerization, a bishydroxyethyl isophthalate component containing a metal sulfonate salt represented by the following chemical formula 1 is charged at 1 to 6 mol% with respect to the diacid component in the polymer, and represented by the following chemical formula 2. The isophthalic acid component is added at 0.01 to 5% by weight based on the diacid component in the polymer, and the polyalkylene ether glycol having an average molecular weight of 1,000 to 20,000 is added at 3 to 15% by weight based on the polymer. A method for producing an alkali-soluble copolyester polymer for composite yarn, which is produced.
Figure 2004323829
Figure 2004323829
 テレフタル酸を主原料とするＴＰＡ重合法によって製造することを特徴とする請求項３記載の複合糸用アルカリ易溶性コポリエステル重合物の製造方法。   The method for producing an alkali-soluble copolyester polymer for composite yarn according to claim 3, characterized in that it is produced by a TPA polymerization method using terephthalic acid as a main raw material.
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