JPH07166420A - Polyester fiber - Google Patents
Polyester fiberInfo
- Publication number
- JPH07166420A JPH07166420A JP5312068A JP31206893A JPH07166420A JP H07166420 A JPH07166420 A JP H07166420A JP 5312068 A JP5312068 A JP 5312068A JP 31206893 A JP31206893 A JP 31206893A JP H07166420 A JPH07166420 A JP H07166420A
- Authority
- JP
- Japan
- Prior art keywords
- less
- rubber
- amount
- polyester fiber
- diepoxy compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 229920000728 polyester Polymers 0.000 title claims abstract description 38
- 239000000835 fiber Substances 0.000 title claims abstract description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims abstract description 20
- 229910052787 antimony Inorganic materials 0.000 claims abstract description 12
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052751 metal Inorganic materials 0.000 claims abstract description 11
- 239000002184 metal Substances 0.000 claims abstract description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 10
- 150000001463 antimony compounds Chemical class 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 229920001971 elastomer Polymers 0.000 abstract description 32
- 239000005060 rubber Substances 0.000 abstract description 32
- -1 polyethylene terephthalate Polymers 0.000 abstract description 10
- 229920000139 polyethylene terephthalate Polymers 0.000 abstract description 9
- 239000005020 polyethylene terephthalate Substances 0.000 abstract description 9
- 238000009987 spinning Methods 0.000 abstract description 6
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 230000003014 reinforcing effect Effects 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 6
- 230000006866 deterioration Effects 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 4
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium dioxide Chemical compound O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000006068 polycondensation reaction Methods 0.000 description 4
- 239000002685 polymerization catalyst Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical group CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000010561 standard procedure Methods 0.000 description 3
- 125000004959 2,6-naphthylene group Chemical group [H]C1=C([H])C2=C([H])C([*:1])=C([H])C([H])=C2C([H])=C1[*:2] 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- LJCFOYOSGPHIOO-UHFFFAOYSA-N antimony pentoxide Chemical compound O=[Sb](=O)O[Sb](=O)=O LJCFOYOSGPHIOO-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- BTVWZWFKMIUSGS-UHFFFAOYSA-N dimethylethyleneglycol Natural products CC(C)(O)CO BTVWZWFKMIUSGS-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229940119177 germanium dioxide Drugs 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 239000012779 reinforcing material Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 1
- 125000004958 1,4-naphthylene group Chemical group 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- WMRCTEPOPAZMMN-UHFFFAOYSA-N 2-undecylpropanedioic acid Chemical compound CCCCCCCCCCCC(C(O)=O)C(O)=O WMRCTEPOPAZMMN-UHFFFAOYSA-N 0.000 description 1
- 125000005828 4,4′-bicyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])(C([H])([H])C([H])([H])C1([H])[*:1])C1([H])C([H])([H])C([H])([H])C([H])([*:2])C([H])([H])C1([H])[H] 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical group OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Chemical group 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical group OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- BXKDSDJJOVIHMX-UHFFFAOYSA-N edrophonium chloride Chemical compound [Cl-].CC[N+](C)(C)C1=CC=CC(O)=C1 BXKDSDJJOVIHMX-UHFFFAOYSA-N 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002291 germanium compounds Chemical class 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical group OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229940082328 manganese acetate tetrahydrate Drugs 0.000 description 1
- CESXSDZNZGSWSP-UHFFFAOYSA-L manganese(2+);diacetate;tetrahydrate Chemical compound O.O.O.O.[Mn+2].CC([O-])=O.CC([O-])=O CESXSDZNZGSWSP-UHFFFAOYSA-L 0.000 description 1
- 238000002074 melt spinning Methods 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical group OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical group OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 229920001223 polyethylene glycol Chemical group 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
Landscapes
- Yarns And Mechanical Finishing Of Yarns Or Ropes (AREA)
- Tires In General (AREA)
- Reinforced Plastic Materials (AREA)
- Tyre Moulding (AREA)
- Artificial Filaments (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、ゴム補強用ポリエステ
ル繊維に関するものである。更に詳しくは、従来品に比
べて高強度であり、ゴム補強材としてゴム中に埋め込ま
れた後の劣化が抑制され、ゴム中での耐熱性に優れたポ
リエステル繊維に関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a rubber-reinforced polyester fiber. More specifically, the present invention relates to a polyester fiber having higher strength as compared with a conventional product, suppressing deterioration after being embedded in rubber as a rubber reinforcing material, and having excellent heat resistance in rubber.
【０００２】[0002]
【従来の技術】ポリエステル繊維は機械的性質・寸法安
定性・耐久性に優れるため衣料用だけでなく、タイヤ、
ベルト、ホース等のゴム製品の補強用材料として産業用
途にも幅広く用いられている。ゴム製品を長時間高温に
さらした場合、ゴム製品中に使用されているポリエステ
ル繊維の劣化が生じやすく強度が低下するため、高温下
での使用を余儀なくされるゴム製品へのポリエステル繊
維への利用には多くの制限があった。この問題を解決す
るため従来から種々の提案がなされている。例えば、ビ
スオキサゾリン化合物やエポキシ化合物、カルボジイミ
ド化合物等のような低ＣＯＯＨ化剤を添加し、ポリエス
テル中に含まれる末端カルボキシル基量の低減化を図る
ことによって上記の欠点を補う方法（特公昭５５−９０
９１号公報，特開昭５６−９１００９号公報など）、ま
た、特定の有機リン化合物の添加（特開昭４７−９８０
８号公報，特開昭４７−９８０９号公報）、銅化合物の
添加（特公昭５６−９５５２号公報）、アクリル酸およ
び／またはメタアクリル酸からなる重合体を付与（特開
昭５５−１６６２３５号公報）等によってゴム中での劣
化を抑制し、ゴム中耐熱性を向上させる方法も知られて
いる。しかしながら、前記した従来の技術による方法は
いずれも実用レベルに未達であったり、ゴム中での劣化
抑制効果は一応認められるものの、製糸性の低下、毛羽
の増加、強度の低下、耐疲労性の低下等を伴い、使用に
おいては多くに問題点があった。2. Description of the Related Art Polyester fiber has excellent mechanical properties, dimensional stability, and durability, and is therefore used not only for clothing but also for tires.
It is widely used in industrial applications as a reinforcing material for rubber products such as belts and hoses. When a rubber product is exposed to a high temperature for a long time, the polyester fiber used in the rubber product easily deteriorates and its strength decreases, so it is inevitable to use it at a high temperature. Had many restrictions. Various proposals have been made in the past to solve this problem. For example, a method of supplementing the above-mentioned drawbacks by adding a low COOH-reducing agent such as a bisoxazoline compound, an epoxy compound or a carbodiimide compound to reduce the amount of terminal carboxyl groups contained in the polyester (Japanese Patent Publication No. 90
91, JP-A-56-91009, etc.) and addition of a specific organic phosphorus compound (JP-A-47-980).
No. 8, JP-A-47-9809), addition of a copper compound (JP-B-56-9552), and addition of a polymer composed of acrylic acid and / or methacrylic acid (JP-A-55-166235). There is also known a method of suppressing deterioration in rubber and improving heat resistance in the rubber, for example, by the publication. However, none of the above-mentioned conventional methods reach the practical level, and although the deterioration suppressing effect in rubber is recognized, the yarn-forming property is decreased, the fluff is increased, the strength is decreased, and the fatigue resistance is reduced. However, there were many problems in use.
【０００３】[0003]
【発明が解決しようとする課題】本発明の目的は上記従
来の問題を解消し、高強度であり、かつ、ゴム中での劣
化を抑制し、ゴム中耐熱性に優れたゴム補強用ポリエス
テル繊維を提供することにある。SUMMARY OF THE INVENTION The object of the present invention is to solve the above-mentioned problems of the prior art, to have high strength, to suppress deterioration in rubber, and to have excellent heat resistance in rubber. To provide.
【０００４】[0004]
【課題を解決するための手段】本発明の目的は、次の構
成によって達成される。一般式［Ｉ］で表されるジエポ
キシ化合物を含有させたポリエステルであり、アンチモ
ン化合物がアンチモン金属量として１０ｐｐｍ以下であ
るポリエステル繊維。The object of the present invention is achieved by the following constitutions. A polyester fiber containing a diepoxy compound represented by the general formula [I], wherein the amount of the antimony compound is 10 ppm or less as an antimony metal amount.
【化２】 以下に本発明を詳細に説明する。本発明で用いるジエポ
キシ化合物は、前記一般式［Ｉ］で示されるものであ
る。 Ａｒの具体例としては、１，４−フェニレン、
１，３−フェニレン、１，２−フェニレン、２−メチル
−１，４−フェニレン、４，４´ビフェニレン、３，３
´−ビフェニレン、２，２´−ビフェニレン、３，４´
−ビフェニレン、１，４−ナフチレン、１，５−ナフチ
レン、２，６−ナフチレン、２，７−ナフチレン、１，
４−シクロヘキシレン、１，３−シクロヘキシレン、
１，２−シクロヘキシレン、４，４´−ビシクロヘキシ
レン、２，６−デカヒドロナフチレンなどが好ましく挙
げられ、なかでも１，４−フェニレン、１，３−フェニ
レンおよび２，６−ナフチレンが特に好ましい。[Chemical 2] The present invention will be described in detail below. The diepoxy compound used in the present invention is represented by the above general formula [I]. Specific examples of Ar include 1,4-phenylene,
1,3-phenylene, 1,2-phenylene, 2-methyl-1,4-phenylene, 4,4 'biphenylene, 3,3
′ -Biphenylene, 2,2′-biphenylene, 3,4 ′
-Biphenylene, 1,4-naphthylene, 1,5-naphthylene, 2,6-naphthylene, 2,7-naphthylene, 1,
4-cyclohexylene, 1,3-cyclohexylene,
1,2-Cyclohexylene, 4,4'-bicyclohexylene, 2,6-decahydronaphthylene and the like are preferably mentioned, and among them, 1,4-phenylene, 1,3-phenylene and 2,6-naphthylene are Particularly preferred.
【０００５】前記一般式［Ｉ］のジエポキシ化合物の重
合度ｎの値は、０または１〜２０の整数であり、０また
は１〜１０の整数が好ましく、また各種の重合度を有す
る化合物の混合物であってもよい。［Ｉ］式で示される
ジエポキシ化合物の製造方法は特に限定されるものでは
ないが、例えば、ヒドロキシカルボン酸とエピハロヒド
リンとを４級アンモニウム塩、３級アミン、３級ホスフ
ィンなどの触媒存在下、４０〜１５０℃で反応させて、
ハロヒドリンエステルエーテル化を行ない、次いでアル
カリ金属塩を添加して脱ハロゲン水素化して製造する方
法が挙げられる。重合度が高いものについては、さらに
ヒドロキシカルボン酸を触媒の存在下、比率を変え反応
させることにより得ることができる。The value of the degree of polymerization n of the diepoxy compound of the general formula [I] is 0 or an integer of 1 to 20, preferably 0 or an integer of 1 to 10, and a mixture of compounds having various degrees of polymerization. May be The method for producing the diepoxy compound represented by the formula [I] is not particularly limited, but for example, hydroxycarboxylic acid and epihalohydrin can be used in the presence of a catalyst such as a quaternary ammonium salt, a tertiary amine or a tertiary phosphine. React at ~ 150 ° C,
A method in which halohydrin ester etherification is carried out, and then an alkali metal salt is added to carry out dehydrohalogenation for production is mentioned. Those having a high degree of polymerization can be obtained by further reacting a hydroxycarboxylic acid in the presence of a catalyst while changing the ratio.
【０００６】本発明における［Ｉ］式で示されるジエポ
キシ化合物のポリエステル繊維中の含有量は、０．００
５重量％以上、１０重量％以下であることが好ましく、
より好ましくは０．０２重量％以上、５重量％以下、さ
らに好ましくは０．１重量％以上、３重量％以下であ
る。ジエポキシ化合物のポリエステル繊維中の含有量が
０．００５重量％以上とするのがゴム中耐熱性の点で好
ましい。また、１０重量％以下とするのが製糸性および
ポリエステル繊維の物性の点で好ましいが、これに限定
されるものではない。The content of the diepoxy compound represented by the formula [I] in the polyester fiber in the present invention is 0.00
It is preferably 5% by weight or more and 10% by weight or less,
It is more preferably 0.02% by weight or more and 5% by weight or less, and even more preferably 0.1% by weight or more and 3% by weight or less. The content of the diepoxy compound in the polyester fiber is preferably 0.005% by weight or more from the viewpoint of heat resistance in rubber. Further, it is preferable that the content is 10% by weight or less from the viewpoints of the thread-forming property and the physical properties of the polyester fiber, but the present invention is not limited thereto.
【０００７】本発明で用いるジエポキシ化合物のポリエ
ステルへの添加・混練は、重縮合反応中または反応終了
直後の溶融状態のポリエステルにジエポキシ化合物を添
加・混練する方法、ポリエステルのチップにジエポキシ
化合物を添加・混合しエクストルーダで混練する方法な
どにより行うことができる。また、あらかじめ、ジエポ
キシ化合物を適当な量比でポリマに混練したものをポリ
エステルに添加することもできる。The diepoxy compound used in the present invention is added to and kneaded with the polyester by a method of adding and kneading the diepoxy compound to the polyester in a molten state during the polycondensation reaction or immediately after the reaction, and adding the diepoxy compound to the polyester chips. It can be performed by a method of mixing and kneading with an extruder. It is also possible to knead a diepoxy compound with a polymer in an appropriate amount ratio in advance and add to the polyester.
【０００８】本発明のポリエステル繊維に含まれるアン
チモン化合物がアンチモン金属量として１０ｐｐｍ以下
である必要がある。該アンチモン金属は、ポリエステル
の重合触媒として用いられるアンチモン化合物の還元に
より生成するが、かかるアンチモン金属はポリエステル
繊維中では異物となるのでポリエステル中に１０ｐｐｍ
より多く存在すると強度が低下するだけでなく、繊維の
異物欠陥が多くなるのでゴム中耐熱性が不良となり好ま
しくない。したがって、ポリエステル繊維中に含まれる
アンチモン金属量は１０ｐｐｍ以下である必要があり、
好ましくは８ｐｐｍ以下、さらに好ましくは５ｐｐｍに
するのがよい。The antimony compound contained in the polyester fiber of the present invention needs to be 10 ppm or less as the amount of antimony metal. The antimony metal is produced by reduction of an antimony compound used as a polymerization catalyst for polyester. Since such antimony metal becomes a foreign substance in the polyester fiber, 10 ppm in the polyester.
If it is present in a larger amount, not only the strength is lowered, but also foreign matter defects of the fiber are increased, so that the heat resistance in the rubber becomes poor, which is not preferable. Therefore, the amount of antimony metal contained in the polyester fiber must be 10 ppm or less,
It is preferably 8 ppm or less, more preferably 5 ppm.
【０００９】なお、本発明のポリエステルの重合触媒に
使用するアンチモン化合物としては三酸化アンチモンま
たは五酸化アンチモンが好ましい。The antimony compound used in the polyester polymerization catalyst of the present invention is preferably antimony trioxide or antimony pentoxide.
【００１０】本発明のポリエステル繊維のカルボキシル
基末端量（以下ＣＯＯＨ量という）は２５ｅｑ／ｔｏｎ
以下とするのが好ましく、また、ジエチレングリコール
含有量（以下ＤＥＧ量という）は１．３ｗｔ％以下とす
るのがゴム中耐熱性の点で好ましいが、これに限定され
るものではない。The polyester fiber of the present invention has a carboxyl group terminal amount (hereinafter referred to as COOH amount) of 25 eq / ton.
The content is preferably the following, and the diethylene glycol content (hereinafter referred to as the DEG content) is preferably 1.3 wt% or less from the viewpoint of heat resistance in rubber, but is not limited thereto.
【００１１】本発明におけるポリエステルは、ポリエチ
レンテレフタレート（以下ＰＥＴと略す）、ポリブチレ
ンテレフタレートおよびポリエチレン−２，６−ナフタ
レートを主体とするものが好ましく、ＰＥＴが更に好ま
しいものであるが、そのジカルボン酸成分の一部をイソ
フタル酸、５−ナトリウムスルホイソフタル酸、２，６
−ナフタレンジカルボン酸、ジフェノキシエタンジカル
ボン酸、アジピン酸、セバシン酸、アゼライン酸、ドデ
カンジカルボン酸等の一種またはそれ以上で置換したも
のでもよい。また、グリコール成分の一部をジエチレン
グリコール、プロピレングリコール、ネオペンチルグリ
コール、ヘキサメチレングリコール、ペンタメチレング
リコール、１，４−シクロヘキサンジメタノール、グリ
セリン、ペンタエリスリトール、ポリエチレングリコー
ル、ポリテトラメチレングリコール等で置き換えてもよ
い。更に、酸化チタン、酸化ケイ素、炭酸カルシウム、
チッ化ケイ素、クレー、タルク、カオリン、カーボンブ
ラック等の顔料のほか、従来公知の着色防止剤、安定
剤、抗酸化剤、難燃剤等の添加剤を含有しても差支えな
い。また、本発明のポリエステルには上記の改質ポリエ
ステル樹脂を２種類以上ブレンドしてもよく、更にはポ
リアミド、ポリエステルアミド、エポキシ樹脂、シリコ
ーン樹脂、ポリオレフィン樹脂、各種ゴム、ポリカーボ
ネート、ポリウレタン、ポリアクリレートなどの樹脂を
少量ブレンドしたものでもよい。The polyester in the present invention is preferably one mainly composed of polyethylene terephthalate (hereinafter abbreviated as PET), polybutylene terephthalate and polyethylene-2,6-naphthalate, and more preferably PET, but its dicarboxylic acid component. A part of isophthalic acid, 5-sodium sulfoisophthalic acid, 2,6
It may be substituted with one or more of naphthalenedicarboxylic acid, diphenoxyethanedicarboxylic acid, adipic acid, sebacic acid, azelaic acid, dodecanedicarboxylic acid and the like. Also, a part of the glycol component may be replaced with diethylene glycol, propylene glycol, neopentyl glycol, hexamethylene glycol, pentamethylene glycol, 1,4-cyclohexanedimethanol, glycerin, pentaerythritol, polyethylene glycol, polytetramethylene glycol, or the like. Good. Furthermore, titanium oxide, silicon oxide, calcium carbonate,
In addition to pigments such as silicon nitride, clay, talc, kaolin and carbon black, conventionally known additives such as anti-coloring agents, stabilizers, antioxidants and flame retardants may be contained. Further, two or more kinds of the above modified polyester resins may be blended with the polyester of the present invention, and further, polyamide, polyesteramide, epoxy resin, silicone resin, polyolefin resin, various rubbers, polycarbonate, polyurethane, polyacrylate, etc. A small amount of the above resin may be blended.
【００１２】本発明のゴム補強用ポリエステル繊維は、
例えば以下のような方法によって得られる。テレフタル
酸ジメチル、エチレングリコールを用い、重合触媒とし
てアンチモン化合物、ゲルマニウム化合物を併用し、リ
ン化合物を用いて重縮合反応を行なう。重縮合に際して
は、仕込み量、重合温度、重合時間を適宜選択し、極限
粘度０．６５以上、ＣＯＯＨ≦２５ｅｑ／ｔｏｎ、ＤＥ
Ｇ≦１．３ｗｔ％のＰＥＴチップを得る。The polyester fiber for rubber reinforcement of the present invention is
For example, it can be obtained by the following method. Dimethyl terephthalate and ethylene glycol are used, an antimony compound and a germanium compound are used together as a polymerization catalyst, and a polycondensation reaction is performed using a phosphorus compound. In the polycondensation, the charged amount, the polymerization temperature, and the polymerization time are appropriately selected, and the intrinsic viscosity is 0.65 or more, COOH ≦ 25 eq / ton, DE
A PET chip with G ≦ 1.3 wt% is obtained.
【００１３】かくして得られたチップを常法に従って固
相重合し、極限粘度０．９５以上とした後、ジエポキシ
化合物を溶融紡糸工程において特定量比で配合する。口
金から吐出した糸条を加熱帯で徐冷した後、チムニー風
で冷却固化させ、引取る。なお、得られるポリエステル
繊維の寸法安定性の面から２０００ｍ／分以上で引取る
のが好ましく、２５００ｍ／分以上で引取るのがより好
ましい。引き続き、または一旦巻き取った後に定法に従
い、延伸・熱処理を行ないポリエステル延伸糸を得る。
かくして得たゴム補強用ポリエステル繊維は定法に従
い、１０ｃｍあたり３０〜６０回の撚り（上撚り）をか
けた後、複数本合糸し、反対方向に１０ｃｍあたり３０
〜６０回の撚り（下撚り）をかけてコードとすることが
でき、次いでこのコードを定法に従い接着剤処理し、処
理コードを得ることができる。The chips thus obtained are subjected to solid phase polymerization according to a conventional method to obtain an intrinsic viscosity of 0.95 or more, and then a diepoxy compound is blended in a specific amount ratio in a melt spinning step. The yarn discharged from the spinneret is gradually cooled in a heating zone, cooled and solidified by chimney air, and then taken up. From the viewpoint of dimensional stability of the obtained polyester fiber, it is preferable to take it off at 2000 m / min or more, more preferably 2500 m / min or more. Continuously or after being once wound, a polyester stretched yarn is obtained by stretching and heat treatment according to a standard method.
The thus obtained rubber-reinforcing polyester fiber is twisted 30 to 60 times per 10 cm (up-twisting) according to a standard method, and then a plurality of plied yarns are combined, and 30 per 10 cm in the opposite direction.
A cord can be obtained by twisting (twisting) 60 times, and then the cord can be treated with an adhesive according to a standard method to obtain a treated cord.
【００１４】本発明のポリエステル繊維のゴム中での劣
化が抑制され、ゴム中耐熱性が向上する理由については
明らかではないが、前記、一般式［Ｉ］式で示されるジ
エポキシ化合物は二官能性であることから該化合物の存
在によって重合度の低下が小さく、むしろポリエステル
の分子鎖が連結されることによって強力低下が少なくな
るためポリエステル繊維におけるゴム中での加水分解が
抑制されること、さらに、特定量のアンチモン金属含有
量とすることによりアンチモン化合物に起因する異物を
低減化でき、ポリエステル繊維中の異物による欠陥が少
なくなるために糸の強度が向上するものと考えられる。Although the reason why the polyester fiber of the present invention is prevented from deterioration in rubber and the heat resistance in rubber is improved is not clear, the diepoxy compound represented by the general formula [I] is difunctional. Therefore, the decrease in the degree of polymerization due to the presence of the compound is small, and rather the decrease in strength due to the fact that the molecular chains of the polyester are linked is suppressed, so that the hydrolysis of the polyester fiber in the rubber is suppressed. It is considered that by setting the specific amount of antimony metal, the amount of foreign substances caused by the antimony compound can be reduced, and the defects due to the foreign substances in the polyester fiber are reduced, so that the strength of the yarn is improved.
【００１５】[0015]
【実施例】以下に実施例を挙げて本発明を詳細に説明す
る。実施例中の物性は次の様にして測定した。The present invention will be described in detail below with reference to examples. Physical properties in the examples were measured as follows.
【００１６】（１）強伸度 東洋ボールドウイン社製テンシロン引張試験機を用い、
試長２５ｃｍ、引取速度３０ｃｍ／分でＳ−Ｓ曲線を求
め強伸度を算出した。(1) Tensile strength Using a Tensilon tensile tester manufactured by Toyo Baldwin,
An elongation curve was calculated by obtaining an SS curve at a test length of 25 cm and a take-up speed of 30 cm / min.
【００１７】（２）ＣＯＯＨ量 試料０．５ｇをｏ−クレゾール１０ｍｌに溶解し、完全
溶解後冷却してからクロロホルム３ｍｌを加え、ＮａＯ
Ｈのメタノール溶液にて電位差滴定を行ない求めた。(2) COOH amount 0.5 g of the sample was dissolved in 10 ml of o-cresol, completely dissolved and cooled, and then 3 ml of chloroform was added to the solution, and NaO was added.
It was determined by performing potentiometric titration with a methanol solution of H.
【００１８】（３）ＤＥＧ量 試料をアルカリ分解した後、ガスクロマトグラフィを用
いて定量した。(3) DEG amount After the sample was alkali decomposed, it was quantified using gas chromatography.
【００１９】（４）ゴム中耐熱性 処理コードをゴム中に埋め込み、１５０℃、６時間加硫
後の強力保持率で評価した。強力保持率６０％以上を
◎、５０％以上６０％未満を○、５０％未満を×とし
た。(4) Heat resistance in rubber The treated cord was embedded in rubber and evaluated by the strength retention after vulcanization at 150 ° C. for 6 hours. A strength retention of 60% or more was marked with ⊚, 50% or more and less than 60% was marked with ◯, and less than 50% was marked with x.
【００２０】（５）アンチモン金属量 試料４０ｇをオルソクロロフェノール５００ｍｌに溶解
し、遠心分離（１２，０００ｒｐｍ×２ｈｒ）後、洗
浄、乾燥する。得られた遠心沈降粒のスペクトルをＸ線
回折装置により測定し、スペクトルから求めた。(5) Antimony metal amount 40 g of a sample is dissolved in 500 ml of orthochlorophenol, centrifuged (12,000 rpm × 2 hr), washed and dried. The spectrum of the obtained centrifugally sedimented particles was measured by an X-ray diffractometer and determined from the spectrum.
【００２１】実施例１〜９ テレフタル酸ジメチル１００部とエチレングリコール５
０部に酢酸マンガン４水塩０．０３２部を添加し、定法
によりエステル交換反応を行なった。得られた生成物に
リン酸０．０１３部を加えた後、三酸化アンチモン０．
０１部、二酸化ゲルマニウム０．００５部を加え、重合
温度２８５℃にて重縮合反応を行なった。 得られたポ
リマは、極限粘度０．６７、ＣＯＯＨ量１８．８eq/to
n、ＤＥＧ０．８３％であり、ポリマ中のアンチモン金
属量は２ｐｐｍであった。このポリマを１６０℃で５時
間予備乾燥後、２２５℃で固相重合し、極限粘度１．０
６のＰＥＴ固相重合チップを得た。この固相重合後のＰ
ＥＴと下記のジエポキシ化合物の混合比率を表１に示す
重量比となるように添加・混合し、エクストルーダー型
紡糸機で紡糸した。Examples 1 to 9 100 parts of dimethyl terephthalate and ethylene glycol 5
0.032 parts of manganese acetate tetrahydrate was added to 0 parts, and transesterification was carried out by a conventional method. After adding 0.013 parts of phosphoric acid to the obtained product, antimony trioxide (0.13 parts) was added.
01 parts and 0.005 parts of germanium dioxide were added, and a polycondensation reaction was carried out at a polymerization temperature of 285 ° C. The polymer obtained has an intrinsic viscosity of 0.67 and a COOH content of 18.8 eq / to.
n, DEG 0.83%, and the amount of antimony metal in the polymer was 2 ppm. The polymer was pre-dried at 160 ° C for 5 hours and then solid-state polymerized at 225 ° C to obtain an intrinsic viscosity of 1.0
A PET solid-state polymerization chip of 6 was obtained. P after this solid state polymerization
The mixing ratio of ET and the diepoxy compound described below was added and mixed so that the weight ratio shown in Table 1 was obtained, and the mixture was spun by an extruder type spinning machine.
【００２２】[0022]
【化３】 紡糸は直径０．６ｍｍφの吐出孔の口金から吐出した紡
出糸を長さ３００ｍｍ、温度３５０℃の加熱筒で徐冷し
た後、１８℃の冷風をあてて冷却固化させ、引取速度４
５００ｍ／分で引取った。このようにして得られた未延
伸糸を延伸温度８５℃、熱処理温度２４０℃で倍率・リ
ラックス率を変更して、表１に示すような延伸糸を得
た。この延伸糸に下撚りをＳ方向に４９Ｔ／１０ｃｍ、
上撚りをＺ方向に４９Ｔ／１０ｃｍかけコードとした。
次にこのコードをリッラー社製コンピュートリータを用
いて接着剤処理し、処理コードを作成した。表１に原糸
および処理コードの物性を示す。表１から明らかなよう
に実施例３〜８は高強度であり、ゴム中耐熱性が優れて
いる。ジエポキシ化合物の含有量が０．００５重量％未
満の実施例１および実施例２はゴム中耐熱性が劣る結果
であった。また、ジエポキシ化合物の含有量が１０重量
％を越える実施例９は糸の強度が低く、延伸時に糸切れ
が多発した。[Chemical 3] The spun yarn was slowly cooled with a heating cylinder having a length of 300 mm and a temperature of 350 ° C., which was discharged from a spinneret having a diameter of 0.6 mmφ, and was cooled and solidified by applying cold air of 18 ° C., and a take-up speed of 4
It was collected at 500 m / min. The undrawn yarn thus obtained was drawn at a drawing temperature of 85 ° C. and a heat treatment temperature of 240 ° C. at different draw ratios / relaxation rates to obtain drawn yarns as shown in Table 1. The twisted yarn is twisted in the S direction with 49T / 10 cm,
The twisted cord was a cord with 49T / 10 cm in the Z direction.
Next, this code was subjected to an adhesive treatment using a computer made by Liller Co., Ltd. to produce a treated code. Table 1 shows the physical properties of the raw yarn and the treated cord. As is clear from Table 1, Examples 3 to 8 have high strength and excellent heat resistance in rubber. In Examples 1 and 2 in which the content of the diepoxy compound was less than 0.005% by weight, the heat resistance in rubber was poor. Further, in Example 9 in which the content of the diepoxy compound was more than 10% by weight, the strength of the yarn was low, and the yarn was frequently broken during drawing.
【００２３】実施例１０ 実施例１〜９での固相重合チップを使用し、下記ジエポ
キシ化合物をＰＥＴ／ジエポキシ化合物＝９９．５／
０．５の割合で添加・混合し、エクストルーダー型紡糸
機で紡糸した。Example 10 The following diepoxy compound was used as the PET / diepoxy compound = 99.5 / using the solid-state polymerized chips of Examples 1-9.
The mixture was added and mixed at a ratio of 0.5 and spun by an extruder type spinning machine.
【００２４】[0024]
【化４】 得られた未延伸糸を延伸し、処理コードを作成した。表
１から明らかなように高強度であり、ゴム中耐熱性が優
れている。[Chemical 4] The obtained undrawn yarn was drawn to prepare a treated cord. As is clear from Table 1, it has high strength and excellent heat resistance in rubber.
【００２５】[0025]
【表１】 実施例１１〜１４ 重合触媒として使用する三酸化アンチモンと二酸化ゲル
マニウムの量を変更した以外は実施例６と同様にして行
なった。ＰＥＴ／ジエポキシ化合物＝９９．５／０．５
の割合で添加・混合し、エクストルーダー型紡糸機で紡
糸した。得られた未延伸糸は実施例６と同様に延伸し、
処理コードを作成した。表２から明らかなように、本発
明の範囲を満たす実施例１１〜１３は強度が高く、ゴム
中耐熱性が優れている。しかしながら、アンチモン金属
量が１０ｐｐｍより多い実施例１４は強度が低く、ゴム
中耐熱性が不良である。[Table 1] Examples 11 to 14 The procedure of Example 6 was repeated except that the amounts of antimony trioxide and germanium dioxide used as the polymerization catalyst were changed. PET / diepoxy compound = 99.5 / 0.5
Was added and mixed in the proportion of, and spun by an extruder type spinning machine. The obtained undrawn yarn was drawn in the same manner as in Example 6,
Created the processing code. As is clear from Table 2, Examples 11 to 13 satisfying the range of the present invention have high strength and excellent heat resistance in rubber. However, in Example 14 in which the amount of antimony metal is more than 10 ppm, the strength is low and the heat resistance in rubber is poor.
【００２６】実施例１５および実施例１６ 実施例６と同様にしてＰＥＴ／ジエポキシ化合物＝９
９．５／０．５の割合で添加・混合し、エクストルーダ
ー型紡糸機で紡糸温度、滞留時間を変えて紡糸し、ＣＯ
ＯＨ量の異なる糸を得た。表２に原糸および処理コード
の物性を示す。表２から明らかなように実施例１６はＣ
ＯＯＨ量が若干多いのでゴム中耐熱性がやや劣る以外は
良好である。Example 15 and Example 16 PET / diepoxy compound = 9 in the same manner as in Example 6.
Add and mix at a ratio of 9.5 / 0.5, and spin with an extruder type spinning machine while changing the spinning temperature and residence time.
Threads with different OH content were obtained. Table 2 shows the physical properties of the raw yarn and the treated cord. As is clear from Table 2, Example 16 is C
Since the amount of OOH is a little large, it is good except that the heat resistance in rubber is slightly inferior.
【００２７】実施例１７および実施例１８ ポリマを製造する際にＤＥＧを添加し、ＤＥＧ含有量を
変更した。得られたチップは実施例１と同様にしてＰＥ
Ｔ／ジエポキシ化合物＝９９．５／０．５の割合で添加
・混合し、実施例１と同様の方法で紡糸、延伸した。表
２に原糸および処理コードの物性を示す。表２から明ら
かなように実施例１８はＤＥＧ量が若干多いのでゴム中
耐熱性がやや劣る以外は良好である。Example 17 and Example 18 DEG was added during the production of the polymer to change the DEG content. The obtained chip was treated with PE in the same manner as in Example 1.
T / diepoxy compound = 99.5 / 0.5 was added and mixed, and the mixture was spun and stretched in the same manner as in Example 1. Table 2 shows the physical properties of the raw yarn and the treated cord. As is clear from Table 2, Example 18 is good except that the heat resistance in the rubber is slightly inferior because the DEG amount is slightly large.
【００２８】[0028]
【表２】 [Table 2]
【００２９】[0029]
【発明の効果】本発明のポリエステル繊維は、従来品に
比べて高強度であり、ゴム中で長時間高温にさらされた
時の劣化が抑制されゴム中耐熱性に優れるのでゴム補強
用ポリエステル繊維として好適である。EFFECTS OF THE INVENTION The polyester fiber of the present invention has higher strength than conventional products, is suppressed from deterioration when exposed to high temperature in rubber for a long time, and is excellent in heat resistance in rubber. Is suitable as
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｄ０１Ｆ 1/10 6/62 ３０１ Ｑ ３０２ Ｃ ３０６ Ｍ Ｄ０２Ｇ 3/48 ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 6 Identification number Office reference number FI technical display location D01F 1/10 6/62 301 Q 302 C 306 M D02G 3/48
Claims (3)
物を含有させたポリエステルであり、アンチモン化合物
がアンチモン金属量として１０ｐｐｍ以下であるポリエ
ステル繊維。 【化１】 1. A polyester fiber containing a diepoxy compound represented by the general formula [I], wherein the amount of the antimony compound is 10 ppm or less as an antimony metal amount. [Chemical 1]
エステル繊維。 Ａ．カルボキシル末端基量（ＣＯＯＨ）（eq/ton） （ＣＯＯＨ）≦２５ Ｂ．ジエチレングリコール含有量（ＤＥＧ）（ｗｔ％） （ＤＥＧ）≦１．３2. The polyester fiber according to claim 1, which has the following characteristics. A. Amount of carboxyl end group (COOH) (eq / ton) (COOH) ≦ 25 B. Diethylene glycol content (DEG) (wt%) (DEG) ≦ 1.3
以上、１０重量％以下含有させた請求項１ないし２に記
載のポリエステル繊維。3. The diepoxy compound is contained in an amount of 0.005% by weight.
The polyester fiber according to claim 1, which is contained in an amount of 10% by weight or less.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5312068A JPH07166420A (en) | 1993-12-13 | 1993-12-13 | Polyester fiber |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5312068A JPH07166420A (en) | 1993-12-13 | 1993-12-13 | Polyester fiber |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH07166420A true JPH07166420A (en) | 1995-06-27 |
Family
ID=18024849
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5312068A Pending JPH07166420A (en) | 1993-12-13 | 1993-12-13 | Polyester fiber |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH07166420A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006028102A1 (en) * | 2004-09-07 | 2006-03-16 | Kaneka Corporation | Artificial hair made of flame-retardant polyester |
-
1993
- 1993-12-13 JP JP5312068A patent/JPH07166420A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006028102A1 (en) * | 2004-09-07 | 2006-03-16 | Kaneka Corporation | Artificial hair made of flame-retardant polyester |
| US8211542B2 (en) | 2004-09-07 | 2012-07-03 | Kaneka Corporation | Artificial hair made of flame-retardant polyester |
| US8545981B2 (en) | 2004-09-07 | 2013-10-01 | Kaneka Corporation | Artificial hair made of flame-retardant polyester |
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