EP1392898A1 - Fibre elastique de type polyurethane, et procede de preparation de la fibre - Google Patents

Fibre elastique de type polyurethane, et procede de preparation de la fibre

Info

Publication number
EP1392898A1
EP1392898A1 EP02718687A EP02718687A EP1392898A1 EP 1392898 A1 EP1392898 A1 EP 1392898A1 EP 02718687 A EP02718687 A EP 02718687A EP 02718687 A EP02718687 A EP 02718687A EP 1392898 A1 EP1392898 A1 EP 1392898A1
Authority
EP
European Patent Office
Prior art keywords
elastic fiber
polyurethane elastic
producing
polymer
prepolymer
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.)
Withdrawn
Application number
EP02718687A
Other languages
German (de)
English (en)
Other versions
EP1392898A4 (fr
Inventor
Il-Cheon Kwon
Doo-Hyun Kim
Kyung-Hwan Ro
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kolon Industries Inc
Original Assignee
Kolon Industries Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from KR1020010020976A external-priority patent/KR100646647B1/ko
Priority claimed from KR1020010020975A external-priority patent/KR100719044B1/ko
Application filed by Kolon Industries Inc filed Critical Kolon Industries Inc
Publication of EP1392898A1 publication Critical patent/EP1392898A1/fr
Publication of EP1392898A4 publication Critical patent/EP1392898A4/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/0895—Manufacture of polymers by continuous processes
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • 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
    • D01F6/70—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyurethanes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913—Rod, strand, filament or fiber

Definitions

  • the aforementioned prior art has many problems, as follows.
  • the temperature of 40 to 50 ° C is too broad not to uniformly mix glycol and diisocyanate.
  • the reaction of glycol and diisocyanate is very intensive. Therefore, at the temperature of more than 45 ° C , a large amount of glycol and diisocyanate are reacted before being uniformly mixed.
  • the supply temperature of glycol and diisocyanate In order to maintain the reaction temperature to be less than 42 ° C , the supply temperature of glycol and diisocyanate must be predetermined to be less than 42 "C prior to being putted in the static mixer. However, when the temperature is deviated from 43-44 ° C , impurity such as dimmer is rapidly increased within diisocyanate. Therefore, in order to maintain the reaction temperature to be less than 42 ° C , a heat exchanger must be installed prior to the static mixer or an external jacket is attached to the static mixer, thereby controlling the temperature. Compared with a method, in which glycol and diisocyanate are mixed at the same temperature as the storage temperature (43-4 ° C) of diisocyanate, this method is improper.
  • the present invention employs a continuous polymerizing tube with a mixing element formed in a Kenics type or a Sulzer type on its inside.
  • the continuous polymerizing tube is shaped in a cylinder pipe.
  • the continuous polymerizing tube comprises a static mixer, a heat raiser, a reactor, and a cooler.
  • the static mixer is designed so that the shear rate is more than 20sec -1 without the inner mixing element.
  • the heat raiser is designed so that the shear rate is more than 3sec _1 without the inner mixing element.
  • the reactor is designed so that the shear rate is more than O.lsec -1 without the inner mixing element.
  • polyol with high molecular weight and diisocyanate with excessive amount are mixed within the static mixer with the shear rate of more than 20sec -1 without the inner mixing element, and reacted within the heat raiser with the shear rate of more than 3sec -1 without the inner mixing element, and reacted within the reactor with the shear rate of more than O. lsec -1 without the inner mixing element, thereby preparing a first prepolymer.
  • polytetramethyleneetherglycol with the number average molecular weight of 1,700-3,000 and 4,4'-methylenediphenyldi- isocyanate which are generally used to produce a polymer for polyurethane elastic fiber, are used.
  • the mole ratio of diisocyanate per glycol is properly about 1.5-1.75.
  • the mixing temperature of the static mixer is controlled to be 43-44 ° C . If the mixing temperature is more than 45 ° C , the reaction is considerably processed prior to the uniform mixing, thereby forming gel of three-dimensional bridged bonds. Components of gel are accumulated within the static mixer or moved into a next step.
  • the shear rate within the heat raiser is very important to set the shear rate within the heat raiser to be more than 3sec -1 without the inner mixing element. If the shear rate is less than 3sec -1 , the heterogeneous reaction is increased and gel is increased within the prepolymer.
  • the shear rate within the reactor is very important to set the shear rate within the reactor to be more than O.lsec -1 without the inner mixing element. If the shear rate is less than O.lsec -1 , the heterogeneous reaction generates the formation of the gel.
  • the prepolymer manufactured by the aforementioned process comprises gels with a diameter of less than 20um. Herein, the number of these gels is 600/g. The gels improve the processing property and the quality of the final product. The number of the gels within the prepolymer is measured by a Coulter Counter.
  • a chain extender and a chain terminator are added to and reacted with the prepolymer, thereby preparing the polyurethane polymer. More particularly, the prepolymer is solved by a N,N'- Dimethylacetamide (hereinafter, referred to as "DMAc") solvent, thereby forming a solution of the prepolymer. This solution is reacted with a N,N'-Dimethylacetamide solution (chain extender) comprising diamine and triamine, and a N,N'-Dimethylacetamide solution (chain terminator) comprising monoamine.
  • diamine used as the chain extender ethylene diamine or 1,2-diaminopropane may be used.
  • triamine diethyltriamine may be used.
  • the prepared polyurethane polymer (hereinafter, referred to as "final polymer”) has a concentration of 36-38.5 weight% according to the amount of N,N'-Dimethylacetamide solution for solving the prepolymer, and a number average molecular weight of 30,000-50,000.
  • the number average molecular weight can be measured by a- Gel Permeation Chromatography (GPC).
  • the polyurethane polymer and an additive are mixed within the static mixer without the inner mixing element at the condition of the shear rate of more than 0.13sec -1 , thereby forming a dope just before spinning.
  • the additive comprises triamine group compound.
  • the additive may be selected from triamine group compound, a conventional antioxidant, an anti-yellowing agent, an ultraviolet stabilizer, a dyeing improving agent, a dulling agent, or a spinning-enhancing agent. More preferably, as the triamine group compound, diethylenetriamine is used.
  • the bridged bonds are formed in high-speed spinning, thereby improving the heat resistance of the elastic fiber, preventing the precipitation due to re-agglutination of inorganic additives, and uniformly mixing the additive and the polymer.
  • the uniform mixture of the additive and the final polymer is very important. If the mixture of the additive and the final polymer is heterogeneous, components of the additive, which are not uniformly dispersed and the mixed, generates wave yarns from the spun elastic fiber, thereby cutting the yarn. Further, the coherence between the filaments is lowered, thereby causing the crack of the filament in a subsequent processing step, and deteriorating the processing property and the quality of the final processed fiber.
  • a static mixer shaped in a cylinder pipe is used.
  • the shear rate within the static mixer is more than 0.13sec -1 without the inner mixing element.
  • the storage temperature of the additive slurry mixed into the final polymer is very important. If the storage temperature of the additive slurry is more than 60 ° C , factors of the raise and the discontinuance of the viscosity of the slurry are larger than factors of the lowering of the precipitation speed due to micro brown motion, thereby promoting the re -agglutination and the precipitation speed of the additive slurry, deteriorating the quality of the additive slurry and promoting the clogging cycle of a filter for the additive. Therefore, the quality and the production of the final polymer are influenced.
  • the storage temperature of the additive slurry is less than 40 ° C , the relative viscosity of the additive slurry against the temperature is raised, thereby increasing the generation of the difference pressure and functioning as an unstable factor of the process. And, the micro brown motion is weak, thereby promoting the re- agglutination, improving the quality of the additive and shortening the clogging cycle of the filter. Therefore, it is preferable to maintain the storage temperature of the additive slurry to be ranged from 40 to 60 ° C .
  • a designated amount of the formed dope is pushed into a spinning tub with the temperature of 180 ⁇ 280 ° C using a gear pump. Thereby, the solvent included in the dope is evaporated, thus preparing the polyurethane elastic fiber.
  • This method is referred to as a dry spinning method.
  • the polymer As the final polymer (dope) comprising various additives is changed into a yarn state, the polymer is chemically changed via transamidation or aminolysis. By this chemical change, the dope is changed into the yarn state and its molecular weight is increased.
  • the number average molecular weight of the elastic fiber, which is prepared by the present invention is about 40,000—70,000.
  • the number average molecular weight of the elastic yarn can be also measured by the Gel Permeation Chromatography (GPC). It is proper to set the spinning speed of the present invention to be 800-1,200 m/sec.
  • the spinning dope produced by the present invention has low content of gel.
  • the additives are uniformly mixed/dispersed within the spinning dope. Therefore, the spinning dope has an excellent spinnability and remarkably reduces the generation of wave yarn.
  • a proper amount of triamine is used as the chain extender and the additive, thereby causing the three-dimensional bridged bonds, and improving the heat resistance, the thermosetting efficiency, and the coherence between the monofilaments.
  • the strength maintenance rate is more than 54%
  • the coherence between the monofilaments is more than 145mgf.
  • the number of gel particles of the prepolymer, the molecular weight of the final polymer and the elastic yarn, the stability of viscosity of the final polymer, the heat resistance, and the thermosetting efficiency of the final polymer are measured, as follows.
  • the prepolymer is solved in 1% LiCl DMAc electrolyte by a 0.5% concentration. Then, the number of gel particles of the prepolymer is measured by the Coulter Counter (Coulter's product in England)
  • the sample with a length of 10cm is elongated at the speed of 500%/30sec until 500%, and is then left for 1 minute. And, the sample is also relaxed. If the produced yarn has at least 2 knobs, which are curved or winds, within a length of 10cm, this yarn is judged as a wave yarn.
  • the judgment of the wave yarn is represented by the number of the wave yarns among 5,000 cheeses in percentage.
  • Length change rate(%) - ⁇ - — founded & z- -z — - — . ⁇
  • One strand of the monofilament is separated by a length of 5cm from the polyurethane elastic yarn comprising plural filaments.
  • One end of the separated monofilament and one ends of other combined monofilaments are attached to an Instrung provided with a rod cell of less than 1kg so that a contact point between the separated monofilament and the non- separated monofilaments is disposed on the center of a cage of 5cm, and then elongated at the speed of 1000%/min, thereby measuring the shear strength of the separated monofilament and the non- separated monofilaments.
  • a result is obtained by the average of the coherences, which are measured during elongation. Each sample are measured more than three times.
  • the continuous polymerizing tube comprises the static mixer with the shear rate of 20sec -1 without the inner mixing element, the heat raiser with the shear rate of 3sec -1 without the inner mixing element, the reactor with the shear rate of O.lsec -1 without the inner mixing element, and the cooler.
  • the static mixer was maintained at 43.5 °C
  • the end of the heat raiser was maintained at 89 °C
  • the reactor was maintained at 88 ° C .
  • Polytetramethyleneetherglycol and 4,4'-diphenyldiisocyanate were reacted for 110 minutes, thereby producing the prepolymer with isocyanate on both ends.
  • the prepolymer was cooled to 40 ° C, and 4,4' -dimethylacetamide was added, thereby producing a solution including the prepolymer of 45%.
  • N,N' -dimethylacetamide solution 98.5 equivalent%, which is used as the chain extender and comprises ethylene diamine of 59.9 mol%, 1,2-diaminopropane of 40 mol% and diethylenetriamine of 0.1 mol%, and N,N' -dimethylacetamide solution 6.5 equivalent%, which is used as the chain terminator and comprises diethylamine, thereby preparing the final polymer.
  • the produced final polymer has the number average molecular weight of is 31,000 and the viscosity of 2,200 poise at 40°C , and comprises solid of 38.5%.
  • the final polymer was uniformly mixed with the additive slurry comprising l,3,5-tris(4-t- buthyl-3-hydroxy-2,6-dimethylbenzene)-l,3,5-triazine-2,4,6- (lH,3H,5H)trion antioxidant of 1.2 weight%, l,l,l',l'-tetramethyl-4,4'- (methylene-di-p-phethylene)disemicarbazide waste gas stabilizer of 1.0 weight%, N-(4-etoxycarbonylphenyl)-N-methyl-N-phenylformamidine ultraviolet stabilizer of 1.5 weight%, titanium oxide of 2 weight%, blue pigment(ultra marine blue) of 0.01 weight%, and diethylenetriamine of 0.2 weight%, and being stored at 45 ° C within the static mixer with the shear rate of 0.13sec -1 without the inner mixing element, thereby producing the dope just before spinning.
  • the additive slurry comprising l,3,5-tri
  • the dope is spun using the spinning tub with the temperature distribution between 260-200 ° C by the dry spinning, thereby producing the polyurethane elastic yarn of 40 denier.
  • Table 1 shows the measured results of the number of gel particles of the prepolymer, the rate of climb of viscosity of the final product, the frequency of generating the wave yarn, the heat resistance and the thermosetting efficiency of the produced elastic yarn, and coherence between monofilaments.
  • the elastic fiber of the present invention has excellent heat resistance (strength maintenance rate), thermosetting and coherence between the monofilaments, thereby being effectively used as a yarn for clothes.
  • the present invention improves the stability of the polymer, has an excellent spinnability even in high-speed spinning, and remarkably reduces the generation of wave yarns.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • General Chemical & Material Sciences (AREA)
  • Textile Engineering (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Artificial Filaments (AREA)

Abstract

L'invention concerne une fibre élastique en polyuréthane, et un procédé de production de ladite fibre. Le procédé se caractérise en ce qu'un polyol de poids moléculaire élevé et un diisocyanate en quantité excessive sont mélangés dans un état de vitesse de cisaillement indiqué et prépolymérisés pour produire un prépolymère. Ce prépolymère est mis en réaction avec un allongeur de chaîne et le terminateur afin de produire un polymère. Un additif est ajouté au polymère et le polymère final est filé. Ce procédé de production de la fibre élastique en polyuréthane améliore la stabilité du polymère, présente une excellente filabilité, et diminue remarquablement la survenue de fils ondulés. La fibre élastique en polyuréthane de l'invention présente une excellente résistance à la chaleur, un thermodurcissement efficient et une force de cohérence entre les monofilaments.
EP02718687A 2001-04-19 2002-04-19 Fibre elastique de type polyurethane, et procede de preparation de la fibre Withdrawn EP1392898A4 (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
KR1020010020976A KR100646647B1 (ko) 2001-04-19 2001-04-19 폴리우레탄계 탄성섬유의 제조방법
KR2001020976 2001-04-19
KR1020010020975A KR100719044B1 (ko) 2001-04-19 2001-04-19 폴리우레탄계 탄성섬유 및 그의 제조방법
KR2001020975 2001-04-19
PCT/KR2002/000714 WO2002086208A1 (fr) 2001-04-19 2002-04-19 Fibre elastique de type polyurethane, et procede de preparation de la fibre

Publications (2)

Publication Number Publication Date
EP1392898A1 true EP1392898A1 (fr) 2004-03-03
EP1392898A4 EP1392898A4 (fr) 2007-08-29

Family

ID=26638999

Family Applications (1)

Application Number Title Priority Date Filing Date
EP02718687A Withdrawn EP1392898A4 (fr) 2001-04-19 2002-04-19 Fibre elastique de type polyurethane, et procede de preparation de la fibre

Country Status (5)

Country Link
US (1) US20040121149A1 (fr)
EP (1) EP1392898A4 (fr)
JP (1) JP2004526069A (fr)
CN (1) CN1270006C (fr)
WO (1) WO2002086208A1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6916896B2 (en) 2003-05-05 2005-07-12 Invista North America S.A.R.L. High productivity spandex fiber process and product
US7838617B2 (en) 2003-05-05 2010-11-23 Invista North America S.àr.l. Dyeable spandex
CN100422398C (zh) * 2006-05-15 2008-10-01 连云港杜钟氨纶有限公司 一种氨纶纺丝新工艺
KR101549276B1 (ko) * 2007-06-22 2015-09-01 인비스타 테크놀러지스 에스.에이 알.엘. 폴리우레탄 탄성사 및 그의 제조 방법
US9279197B2 (en) * 2010-01-14 2016-03-08 Invista North America S.A.R.L. Spandex with high uniformity
CN107289806A (zh) * 2017-06-22 2017-10-24 兰州蓝星纤维有限公司 一种碳纤维原丝纺前原液温度控制的装置及其方法

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3639652A (en) * 1968-03-18 1972-02-01 Henri Albert Mommaerts Continuous process for polymerizing urethane prepolymers
US5000899A (en) * 1988-05-26 1991-03-19 E. I. Du Pont De Nemours And Company Spandex fiber with copolymer soft segment
EP0544009A1 (fr) * 1991-06-13 1993-06-02 Asahi Kasei Kogyo Kabushiki Kaisha Polyurethane-uree segmentee lineaire et production de ce compose
US5362432A (en) * 1993-04-02 1994-11-08 E. I. Du Pont De Nemours And Company Process for dry spinning spandex
EP1055692A2 (fr) * 1999-05-26 2000-11-29 Bayer Aktiengesellschaft Méthode de fabrication en continu de polyuréthanes façonnables sous forme thermoplastique
EP1055691A2 (fr) * 1999-05-26 2000-11-29 Bayer Aktiengesellschaft Méthode de fabrication en continu de polyuréthanes façonnables sous forme thermoplastique
WO2001014441A1 (fr) * 1999-08-26 2001-03-01 Henkel Corporation Procede de preparation de polymeres de polyurethane

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19520732A1 (de) * 1995-06-07 1996-12-12 Bayer Ag Thermoplastische Polyurethan-Elastomere
KR100239204B1 (ko) * 1995-06-23 2000-01-15 야마모토 카즈모토 폴리우레탄 탄성 섬유 및 그의 제조 방법
EP0907771B1 (fr) * 1996-06-24 2003-02-12 E.I. Du Pont De Nemours And Company Films et fibres en polyurethane
JPH10226921A (ja) * 1996-12-13 1998-08-25 Du Pont Toray Co Ltd ポリウレタン繊維およびその製法
US6096252A (en) * 1998-01-29 2000-08-01 Dupont Toray Co., Ltd. Process of making polyurethane fiber

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3639652A (en) * 1968-03-18 1972-02-01 Henri Albert Mommaerts Continuous process for polymerizing urethane prepolymers
US5000899A (en) * 1988-05-26 1991-03-19 E. I. Du Pont De Nemours And Company Spandex fiber with copolymer soft segment
EP0544009A1 (fr) * 1991-06-13 1993-06-02 Asahi Kasei Kogyo Kabushiki Kaisha Polyurethane-uree segmentee lineaire et production de ce compose
US5362432A (en) * 1993-04-02 1994-11-08 E. I. Du Pont De Nemours And Company Process for dry spinning spandex
EP1055692A2 (fr) * 1999-05-26 2000-11-29 Bayer Aktiengesellschaft Méthode de fabrication en continu de polyuréthanes façonnables sous forme thermoplastique
EP1055691A2 (fr) * 1999-05-26 2000-11-29 Bayer Aktiengesellschaft Méthode de fabrication en continu de polyuréthanes façonnables sous forme thermoplastique
WO2001014441A1 (fr) * 1999-08-26 2001-03-01 Henkel Corporation Procede de preparation de polymeres de polyurethane

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of WO02086208A1 *

Also Published As

Publication number Publication date
JP2004526069A (ja) 2004-08-26
US20040121149A1 (en) 2004-06-24
CN1509352A (zh) 2004-06-30
WO2002086208A1 (fr) 2002-10-31
EP1392898A4 (fr) 2007-08-29
CN1270006C (zh) 2006-08-16

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