WO2023013331A1 - ケミカルリサイクルｐｅｔ繊維、ゴム－繊維複合体、コンベヤベルト、ホース及びタイヤ - Google Patents

ケミカルリサイクルｐｅｔ繊維、ゴム－繊維複合体、コンベヤベルト、ホース及びタイヤ Download PDF

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Publication number
WO2023013331A1
WO2023013331A1 PCT/JP2022/026410 JP2022026410W WO2023013331A1 WO 2023013331 A1 WO2023013331 A1 WO 2023013331A1 JP 2022026410 W JP2022026410 W JP 2022026410W WO 2023013331 A1 WO2023013331 A1 WO 2023013331A1
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WO
WIPO (PCT)
Prior art keywords
recycled pet
chemically
chemically recycled
pet fiber
pet
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.)
Ceased
Application number
PCT/JP2022/026410
Other languages
English (en)
French (fr)
Japanese (ja)
Inventor
将大 藤江
健一 杉本
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.)
Bridgestone Corp
Original Assignee
Bridgestone Corp
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
Application filed by Bridgestone Corp filed Critical Bridgestone Corp
Priority to CN202280054402.2A priority Critical patent/CN117795141A/zh
Priority to US18/294,751 priority patent/US20240344242A1/en
Priority to JP2023539718A priority patent/JPWO2023013331A1/ja
Priority to EP22852757.8A priority patent/EP4382645A4/en
Publication of WO2023013331A1 publication Critical patent/WO2023013331A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • C08G63/19—Hydroxy compounds containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J11/00—Recovery or working-up of waste materials
    • C08J11/04—Recovery or working-up of waste materials of polymers
    • C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B60—VEHICLES IN GENERAL
    • B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
    • B60C9/00—Reinforcements or ply arrangement of pneumatic tyres
    • B60C9/0042—Reinforcements made of synthetic materials
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
    • B65G—TRANSPORT OR STORAGE DEVICES, e.g. CONVEYORS FOR LOADING OR TIPPING, SHOP CONVEYOR SYSTEMS OR PNEUMATIC TUBE CONVEYORS
    • B65G15/00—Conveyors having endless load-conveying surfaces, i.e. belts and like continuous members, to which tractive effort is transmitted by means other than endless driving elements of similar configuration
    • B65G15/30—Belts or like endless load-carriers
    • B65G15/32—Belts or like endless load-carriers made of rubber or plastics
    • B65G15/34—Belts or like endless load-carriers made of rubber or plastics with reinforcing layers, e.g. of fabric
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
    • C08J2367/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
    • C08J2367/03—Polyesters derived from dicarboxylic acids and dihydroxy compounds the dicarboxylic acids and dihydroxy compounds having the hydroxy and the carboxyl groups directly linked to aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
    • C08J2367/04—Polyesters derived from hydroxy carboxylic acids, e.g. lactones
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2207/00—Properties characterising the ingredient of the composition
    • C08L2207/20—Recycled plastic
    • D—TEXTILES; PAPER
    • D10—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
    • D10B—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
    • D10B2505/00—Industrial
    • D—TEXTILES; PAPER
    • D10—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
    • D10B—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
    • D10B2505/00—Industrial
    • D10B2505/02—Reinforcing materials; Prepregs
    • D10B2505/022—Reinforcing materials; Prepregs for tyres
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
    • F16L—PIPES; JOINTS OR FITTINGS FOR PIPES; SUPPORTS FOR PIPES, CABLES OR PROTECTIVE TUBING; MEANS FOR THERMAL INSULATION IN GENERAL
    • F16L11/00—Hoses, i.e. flexible pipes
    • F16L11/02—Hoses, i.e. flexible pipes made of fibres or threads, e.g. of textile
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
    • F16L—PIPES; JOINTS OR FITTINGS FOR PIPES; SUPPORTS FOR PIPES, CABLES OR PROTECTIVE TUBING; MEANS FOR THERMAL INSULATION IN GENERAL
    • F16L11/00—Hoses, i.e. flexible pipes
    • F16L11/04—Hoses, i.e. flexible pipes made of rubber or flexible plastics
    • 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
    • Y02W30/00—Technologies for solid waste management
    • Y02W30/50—Reuse, recycling or recovery technologies
    • Y02W30/62—Plastics recycling; Rubber recycling

Definitions

  • the present invention relates to chemically recycled PET fibers, rubber-fiber composites, conveyor belts, hoses and tires.
  • Polyesters are now used in many products for human consumption, the most popular being the saturated polyester obtained from the reaction of terephthalic acid and ethylene glycol, more commonly known as PET. There is polyethylene terephthalate. The consumption of PET has grown rapidly in recent years, and in particular the compound is used in large quantities in the manufacture of containers for various liquid products such as bottled beverages.
  • PET is widely used, especially in the production of beverage bottles, due to its light weight, high durability, low gas permeability, and above all, no harmful effects on human health.
  • PET is highly resistant to the atmosphere and organisms and decomposes very slowly, so there is a problem that mass production causes environmental problems.
  • Patent Literature 1 discloses a technique of depolymerizing PET waste into monomers and polymerizing the depolymerized monomers to produce chemically recycled PET, which is used as a reinforcing material for tires.
  • PET recycled by the technology of Patent Document 1 or the like has the problem that the components (impurities) contained in the PET products used as recycled materials hinder crystallization and facilitate deterioration. Therefore, application to applications requiring strength and durability such as tire cords is not sufficient, and further improvements have been desired.
  • an object of the present invention is to provide a chemically recycled PET fiber that is suppressed in deterioration and has excellent strength and durability.
  • Another object of the present invention is to provide rubber-tire composites, conveyor belts, hoses and tires that are excellent in strength and durability.
  • PET terephthalic acid
  • DMT dimethyl terephthalate
  • BHET bis(2-hydroxyethyl) terephthalate
  • impurities include, for example, isophthalic acid (IPA), diethylene glycol (DEG), etc. contained in the raw material PET product, or components represented by the following formulas (1) and (2) contained in the BHET oligomer. mentioned.
  • IPA isophthalic acid
  • DEG diethylene glycol
  • the present inventors found that the terminal carboxyl group (CEG) of the chemically recycled PET fiber acts as a catalyst for the deterioration reaction and promotes the deterioration reaction, and the CEG concentration If it is possible to keep the CEG concentration low and increase the crystallinity of PET to a certain level or more even if a certain amount of impurities such as IPA is contained, , the deterioration of chemically recycled PET fibers can be suppressed, and excellent strength and durability can be realized.
  • CEG terminal carboxyl group
  • the chemically recycled PET fiber of the present invention comprises monomers containing terephthalic acid (TPA) and/or dimethyl terephthalate (DMT) obtained by depolymerizing PET products, and bis(2-hydroxyethyl) terephthalate.
  • a chemically recycled PET fiber obtained by polymerizing a raw material containing at least one of an intermediate containing (BHET), wherein the chemically recycled PET fiber has a terminal carboxyl group concentration (CEG) of 15 eq/ton or less. and a crystallinity of 40% or more.
  • the rubber-fiber composite of the present invention is characterized by using the above-described chemically recycled PET fiber of the present invention.
  • the conveyor belt of the present invention is characterized by using the chemically recycled PET fiber of the present invention described above.
  • the hose of the present invention is characterized by using the chemically recycled PET fiber of the present invention described above.
  • the tire of the present invention is characterized by using the chemically recycled PET fiber of the present invention described above.
  • the present invention it is possible to provide chemically recycled PET fibers whose deterioration is suppressed and which are excellent in strength and durability. Further, according to the present invention, it is possible to provide rubber-fiber composites, conveyor belts, hoses and tires that are excellent in strength and durability.
  • the chemically recycled PET fiber of the present invention includes monomers such as terephthalic acid (TPA) and dimethyl terephthalate (DMT) obtained by depolymerizing PET products, and bis(2-hydroxyethyl) terephthalate (BHET).
  • TPA terephthalic acid
  • DMT dimethyl terephthalate
  • BHET bis(2-hydroxyethyl) terephthalate
  • the PET products to be recycled are plastic products mainly composed of polyethylene terephthalate, and examples thereof include PET bottles, food packaging films, optical sheets, clothing fibers, and tire cords. Among these, it is preferable to use a PET bottle as the PET product. This is because it is easy to obtain in large quantities and is easy to process.
  • the PET product is preferably pulverized (made into flakes) prior to the step of depolymerizing into monomers, BHET, etc., although not particularly limited.
  • PET polyethylene terephthalate
  • MEG polyethylene terephthalate
  • PET polyethylene terephthalate
  • BHET polyethylene terephthalate
  • the raw materials are monomers containing terephthalic acid (TPA) and/or dimethyl terephthalate (DMT) obtained by depolymerization of PET products, and bis(2- hydroxyethyl) (BHET).
  • TPA terephthalic acid
  • DMT dimethyl terephthalate
  • BHET bis(2- hydroxyethyl)
  • PET polyethylene terephthalate
  • impurities such as isophthalic acid (IPA) and diethylene glycol (DEG) are randomly contained, as shown in formula (3) below.
  • This impurity was contained in the PET product from which it was recycled, and when chemical recycling is performed, it can be removed to some extent by purifying it before polymerization, but it is unavoidably contained.
  • the intermediates such as BHET obtained by chemical recycling are not only pure (without impurities) BHET oligomers as shown in formula (4), but also components as shown in formulas (5) and (6). is contained in the BHET oligomer, it is extremely difficult to purify them by distillation or the like to remove the components that become impurities.
  • an intermediate such as BHET containing these impurities is polymerized, there is a problem that crystallization of PET is inhibited and PET fibers are likely to deteriorate.
  • the terminal carboxyl group (CEG) concentration is controlled to 15 eq / ton or less and the crystallinity is controlled to 40% or more to remove impurities As a result of being able to suppress deterioration while containing, strength and durability can be improved.
  • a hydrolysis method is used as a depolymerization method for obtaining the TPA.
  • a methanolysis method is used as a depolymerization technique for obtaining the DMT.
  • the intermediates such as BHET include not only completely decomposed pure BHET but also oligomers of BHET partially containing impurity components as shown in formulas (5) and (6).
  • a glycolysis method is used when decomposing into intermediates such as BHET. When this method is used, it is possible to obtain the effect of shortening the recycling process and reducing the cost required for recycling, as compared with the case where monomers such as TPA and DMT are depolymerized.
  • the intermediates such as BHET obtained by depolymerizing the PET product preferably do not contain residual components such as polymerization catalysts and dyes.
  • the residual component may adversely affect the deterioration of the obtained chemically recycled PET fiber, and if there is a large amount of the residual polymerization catalyst, it may become difficult to control the polymerization reaction during repolymerization.
  • the strength and durability of chemically recycled PET fibers can be more reliably improved.
  • the chemically recycled PET fiber of the present invention has a degree of crystallinity of 40% or more from the viewpoint of being able to further improve strength and durability. If the degree of crystallinity of the chemically recycled PET fiber is 40% or more, even if there is an influence of inhibition of crystallization due to the above-mentioned IPA, DEG, etc., the penetration of moisture, amine, etc. in the rubber into the amorphous region This is because it is considered possible to suppress the deterioration reaction that is likely to be caused to a level that poses no problem in terms of product use. From the same point of view, the crystallinity of the chemically recycled PET fiber is preferably 45% or more.
  • the chemically recycled PET fiber of the present invention has a terminal carboxyl group concentration (CEG) of 15 eq/ton or less from the viewpoint of suppressing deterioration of the PET fiber. This is because when the CEG of the chemically recycled PET fiber is 15 eq/ton or less, acceleration of deterioration due to terminal carboxyl groups is minimized, and deterioration can be suppressed. Furthermore, it is preferable that the terminal carboxyl group (CEG) concentration in the obtained chemically recycled PET fiber is 10 eq/ton or less.
  • the CEG in the chemically recycled PET fiber can be measured by the titration method described in Analytic. Chem., 26, 1614 (1954).
  • the obtained chemically recycled PET fibers preferably have a diethylene glycol (DEG) content of 1.0% by weight or less, and 0.5% by weight or less. is more preferred.
  • DEG diethylene glycol
  • the content of DEG in the chemically cycled PET fiber was measured by GC after decomposition with hydrazine according to the method described in J. Polym. Sci., Part A-1, 8, 679-682 (1970). can be quantified.
  • the raw material obtained by depolymerizing the PET product is polymerized by solid phase polymerization following melt polymerization.
  • Detailed polymerization conditions conditions such as catalyst, reaction temperature, polymerization time, etc. are not particularly limited, and can be appropriately selected according to the use and required performance of the chemically recycled PET fiber.
  • the chemically recycled PET fiber of the present invention is a fibrous PET resin obtained through the above polymerization.
  • the fiber conditions are not particularly limited, and can be appropriately selected according to the use and required performance of the chemically recycled PET fiber.
  • the chemically recycled PET fiber of the present invention preferably has an intrinsic viscosity of 0.9 to 1.05 dl/g.
  • the chemically recycled PET fiber has an intrinsic viscosity of 0.9 dl/g or more, the strength of the PET fiber can be enhanced. This is because when the intrinsic viscosity of the chemically recycled PET fiber is 1.05 dl/g or less, problems such as deterioration of workability do not occur.
  • the chemically recycled fiber of the present invention may further contain PET derived from biomass. This can further reduce the load on the environment.
  • the biomass-derived PET include PET products obtained by polymerizing ethylene glycol and terephthalic acid, which are made from non-petroleum-derived materials such as plants. Chemically recycled PET can be obtained by depolymerizing such biomass-derived PET and then repolymerizing it. Also, mechanically recycled PET can be obtained by remolding after melting biomass-derived PET.
  • the biomass-derived PET also includes those having isophthalic acid and terminal carboxyl groups (CEG) during the manufacturing process.
  • the rubber-fiber composite of the present invention is characterized by using the above-described chemically recycled PET fiber of the present invention.
  • excellent strength and durability can be realized even in a rubber-fiber composite using recycled materials.
  • the rubber-fiber composite of the present invention only needs to contain the chemically recycled PET fiber, and can be used by mixing with other organic fibers. Further, other conditions for the chemically recycled PET fiber can be appropriately selected according to the required performance.
  • the tire of the present invention is characterized by using the above-mentioned chemically recycled PET fiber of the present invention.
  • the chemically recycled PET fiber of the present invention in a member, excellent strength and durability can be achieved even when a tire cord made of recycled material is included.
  • the rubber-fiber composite When used for a tire, it is preferably used as a pneumatic tire carcass or a belt reinforcing layer, but is not limited thereto. It can also be suitably used for other members.
  • the conveyor belt of the present invention is characterized by using the chemically recycled PET fiber of the present invention described above.
  • the hose of the present invention is characterized by using the chemically recycled PET fiber of the present invention described above.
  • the structure of the chemically recycled PET fiber is the same as that described in the chemically recycled PET fiber of the present invention.
  • the present invention it is possible to provide chemically recycled PET fibers whose deterioration is suppressed and which are excellent in strength and durability. Further, according to the present invention, it is possible to provide rubber-fiber composites, conveyor belts, hoses and tires that are excellent in strength and durability.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Sustainable Development (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
  • Reinforced Plastic Materials (AREA)
PCT/JP2022/026410 2021-08-05 2022-06-30 ケミカルリサイクルｐｅｔ繊維、ゴム－繊維複合体、コンベヤベルト、ホース及びタイヤ Ceased WO2023013331A1 (ja)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CN202280054402.2A CN117795141A (zh) 2021-08-05 2022-06-30 化学回收的pet纤维、橡胶-纤维复合体、输送带、软管和轮胎
US18/294,751 US20240344242A1 (en) 2021-08-05 2022-06-30 Chemically-recycled pet fiber, rubber-fiber composite, conveyor belt, hose and tire
JP2023539718A JPWO2023013331A1 (https=) 2021-08-05 2022-06-30
EP22852757.8A EP4382645A4 (en) 2021-08-05 2022-06-30 Chemically-recycled pet fibers, rubber-fiber composite, conveyor belt, hose and tire

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2021129363 2021-08-05
JP2021-129363 2021-08-05

Publications (1)

Publication Number Publication Date
WO2023013331A1 true WO2023013331A1 (ja) 2023-02-09

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Family Applications (1)

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PCT/JP2022/026410 Ceased WO2023013331A1 (ja) 2021-08-05 2022-06-30 ケミカルリサイクルｐｅｔ繊維、ゴム－繊維複合体、コンベヤベルト、ホース及びタイヤ

Country Status (5)

Country Link
US (1) US20240344242A1 (https=)
EP (1) EP4382645A4 (https=)
JP (1) JPWO2023013331A1 (https=)
CN (1) CN117795141A (https=)
WO (1) WO2023013331A1 (https=)

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JP2000169623A (ja) * 1998-12-10 2000-06-20 Is:Kk ポリエチレンテレフタレ―ト廃棄物のケミカルリサイクル方法
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Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0625916A (ja) * 1991-12-26 1994-02-01 Toray Ind Inc シートベルト用ポリエステル繊維
JP2000512250A (ja) * 1996-06-04 2000-09-19 ローマン ゲーエムベーハー ウンド コー．カーゲー 食品用コンベヤベルト
JP2000169623A (ja) * 1998-12-10 2000-06-20 Is:Kk ポリエチレンテレフタレ―ト廃棄物のケミカルリサイクル方法
JP2002161437A (ja) * 2000-11-30 2002-06-04 Teijin Ltd ポリアルキレンテレフタレート繊維及びその識別方法
JP2003055300A (ja) * 2001-08-17 2003-02-26 Is:Kk ビス−β−ヒドロキシエチルテレフタレートの製造法
JP2004019783A (ja) * 2002-06-17 2004-01-22 Ashimori Ind Co Ltd 消防用ホース
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