WO2014146589A1 - Procédé pour produire un polyester recyclé à point de fusion bas pour utilisation dans la production de polyester noyau-coque par dégradation hydrolytique - Google Patents
Procédé pour produire un polyester recyclé à point de fusion bas pour utilisation dans la production de polyester noyau-coque par dégradation hydrolytique Download PDFInfo
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- WO2014146589A1 WO2014146589A1 PCT/CN2014/073752 CN2014073752W WO2014146589A1 WO 2014146589 A1 WO2014146589 A1 WO 2014146589A1 CN 2014073752 W CN2014073752 W CN 2014073752W WO 2014146589 A1 WO2014146589 A1 WO 2014146589A1
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- WIPO (PCT)
- Prior art keywords
- polyester
- melting point
- sheath
- low
- acetate
- Prior art date
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Classifications
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- 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
- D01F8/00—Conjugated, i.e. bi- or multicomponent, artificial filaments or the like; Manufacture thereof
- D01F8/04—Conjugated, i.e. bi- or multicomponent, artificial filaments or the like; Manufacture thereof from synthetic polymers
- D01F8/14—Conjugated, i.e. bi- or multicomponent, artificial filaments or the like; Manufacture thereof from synthetic polymers with at least one polyester as constituent
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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
- C08G63/16—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
- C08G63/78—Preparation processes
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- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01D—MECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
- D01D5/00—Formation of filaments, threads, or the like
- D01D5/28—Formation of filaments, threads, or the like while mixing different spinning solutions or melts during the spinning operation; Spinnerette packs therefor
- D01D5/30—Conjugate filaments; Spinnerette packs therefor
- D01D5/34—Core-skin structure; Spinnerette packs therefor
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- 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
- D01F13/00—Recovery of starting material, waste material or solvents during the manufacture of artificial filaments or the like
- D01F13/04—Recovery of starting material, waste material or solvents during the manufacture of artificial filaments or the like of synthetic polymers
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- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
- Y02P70/62—Manufacturing or production processes characterised by the final manufactured product related technologies for production or treatment of textile or flexible materials or products thereof, including footwear
Definitions
- the invention relates to the technical field of chemical fiber production, in particular to a preparation method of a low melting point recycled polyester for a sheath-core type polyester.
- the low-melting-point sheath-core composite polyester staple fiber refers to a fiber obtained by distributing a core-core structure of the two different polymers of a low-melting-point polyester and a conventional polyester in the same fiber.
- the skin layer is a low melting point polyester which retains some of the characteristics of conventional polyesters and has good compatibility with conventional polyesters.
- the low melting point sheath-core composite fiber is mainly used for the heat bonding fiber, and the main function in the production of the nonwoven fabric is that the low melting point fiber skin layer polymer melts at a certain temperature, thereby exerting a bonding effect in the fiber web.
- the produced non-woven fabric has the characteristics of soft handfeel and high elasticity, and is widely used in sanitary masks, bandages and other sanitary materials and interior decoration materials. field.
- the invention patent "a low melting point copolyester and a preparation method thereof" discloses a design method of a low melting point copolyester, the melting point of the polyester can be lowered to 110 ° C, and the low melting point copolyester crystallizes Good performance, high intrinsic viscosity, difficult adhesion of particles, good spinnability, etc.
- Invention patent "manufacturing method of low melting point polyester staple fiber” (application number: 200410072878.2 The low melting point short fiber is obtained by melt spinning after low temperature vacuum drying of the polyester chip having a low melting point of 120 ° C to 130 ° C.
- Invention patent "a side-by-side composite low-melting staple fiber” (application number: 200810123792.6) discloses that a water-soluble polyester component and a polytrimethylene terephthalate component are juxtaposed into a low-melting staple fiber, and the fiber has good heat shrinkage stability. There have been some reports on the research of low melting core-sheath composite polyester fibers.
- the invention patent "manufacturing method of sheath-core type low-melting polyester staple fiber" (application No.: 200810163542.5) is characterized in that the skin layer is a low-melting polyester melt obtained by direct spinning of a melt, and the core layer is passed through conventional PET.
- a conventional PET polyester melt obtained by a slicing process obtained by a slicing process.
- the use of recycled materials for the preparation of polyester staple fibers as the core layer of sheath-core composite fibers has not been reported so far.
- polyester waste Recycling has become a necessity for a sustainable society.
- Most of the short fibers currently prepared from polyester waste are used in low-addition fields such as fillers. Studying the quenching and tempering process to solve the technical problems of wide sources of polyester waste, complex composition and high quality fluctuations.
- the use of polyester waste to prepare products with high added value has become a major issue in the transformation and upgrading of the recycling industry.
- the technology replaces low-melting polyester chip spinning with melt direct spinning, which better solves a series of problems such as high drying cost, poor stability and poor fiber spinnability of Russian low-melting polyester, and the production cost is greatly reduced.
- the first object of the present invention is to provide a method for producing a low-melting-recycled polyester for leather core type polyester by hydrolysis degradation, which is prepared by the method
- the low-melting-recycled polyester can be used for preparing the sheath-core type polyester staple fiber, and the added value of the polyester waste to prepare the recycled polyester staple fiber is improved, and the prepared sheath-core type recycled polyester staple fiber has the characteristics of stable quality and excellent quality.
- a second object of the present invention is to provide a low melting point regenerated polyester prepared by the above process.
- a third object of the present invention is to provide an application of the low melting point regenerated polyester prepared by the above method.
- Hydrolytic degradation method for producing a low melting point regenerated polyester for sheath-core type polyester which is obtained by degradation and polycondensation reaction of the following raw materials:
- neopentyl glycol e. one or more of neopentyl glycol, hexanediol, butylene glycol and polyethylene glycol;
- the esterification reaction of terephthalic acid with ethylene glycol is carried out under nitrogen pressure, the molar ratio of terephthalic acid to d is 2 to 5:1; the molar ratio of terephthalic acid to e is 3 ⁇ 19:1; the molar ratio of terephthalic acid to ethylene glycol is: 20:80-80:20; the molar ratio of alkyd is 1.4-1.6:1; the feeding of f and g is 200-600 ppm of acid;
- the alcohol is the sum of ethylene glycol and e, the acid is the sum of terephthalic acid and d; the temperature of the esterification reaction is 180-250 ° C, the pressure is 0.05 MPa - 0.4 MPa, and the reaction time is 1.5 - 3h; polycondensation reaction temperature is 250 ⁇ 285 ° C, vacuum degree is 30 ⁇ 200Pa, reaction time 2.5 ⁇ 5h.
- the low-melting-recycled polyester has a melting point of 70 to 160 ° C, a terminal carboxyl group content of ⁇ 35 mmol/kg, and an intrinsic viscosity of 0.5 dL/g to 1.0 OdL/g.
- the low-melting-recycled polyester has an intrinsic viscosity of 0.55 dL/g to 0.75 dL/g.
- the recycled raw material comprises one or more of a reconstituted polyester bottle flake and a waste polyester textile.
- the present invention also provides a low melting point regenerated polyester prepared by the above preparation method.
- the present invention also provides a sheath-core type polyester staple fiber having a low-melting-recycled polyester as described above.
- the low-melting-recycled polyester of the invention can be used for preparing sheath-core type polyester staple fibers, and the added value of the prepared polyester staple fiber for polyester scrap is improved, and the prepared sheath-core type recycled polyester staple fiber has stable quality and excellent quality. specialty. Can be used in the production of non-woven fabrics, flocking, composite materials and other industries.
- the mass ratio of recycled raw materials to methanol is 1:6; the mass ratio of recycled raw materials to zinc acetate is 100:0.5; the above raw materials are polymerized by methanol to prepare recycled low-melting polyester.
- the degradation temperature is 190 ° C, the pressure is 2.5 Mpa, the reaction time is 3 h, the reaction is completed when the pressure returns to atmospheric pressure, the reaction is filtered, the obtained liquid is rotary evaporated, and methanol and ethylene glycol are separately distilled off to obtain a solid matter. It was dissolved in hot ethanol and filtered, and the obtained liquid was evaporated to give dimethyl terephthalate (DMT).
- DMT dimethyl terephthalate
- the molar ratio of dimethyl terephthalate (DMT) to isophthalic acid (IPA) is 3:1; the molar ratio of dimethyl terephthalate (DMT) to neopentyl glycol (NPG) is 7:1; the molar ratio of dimethyl terephthalate (DMT) to ethylene glycol is 1:2; the molar ratio of alcohol (sum of ethylene glycol to neopentyl glycol (NPG)) is 1.5:1
- Catalyst antimony trioxide (Sb203) and cobalt acetate (Co(Ac)2) It is 300 ppm of the total amount of acid in the reaction system, and a stabilizer of trimethyl phosphate is added in an amount of 0.01% by weight (relative to the acid component).
- the esterification reaction was carried out under a nitrogen pressure at a temperature of 220 ° C, a pressure of 0.15 MPa, a reaction time of 2.2 h, a polycondensation reaction temperature of 275 ° C, a vacuum of 90 Pa, and a reaction time of 3.5 h.
- the obtained low melting point polyester had a melting point of 110 ° C, a terminal carboxyl group content of 25 mmol/kg, and an intrinsic viscosity of 0.69 dL/g.
- the preparation of recycled polyester the use of bottle flakes through cleaning, drum drying, multi-stage filtration, liquid phase thickening process.
- the drum drying temperature was 130 ° C
- the drying time was 8 h.
- the steps of liquid phase thickening are as follows: 1) The melt having a temperature of 270 ° C and an intrinsic viscosity of 0.55 dl / g after being melted by the screw is pumped to the vacuum separation tower by melt transfer, and the melt is at a vacuum of 100 Pa, and the temperature is At 280 ° C, the intrinsic viscosity can reach 0.68 dl / g after staying for 30 min; 2) the melt enters the secondary quenching and tempering adjustment device, the melt temperature and vacuum degree in the secondary quenching and tempering device and the vacuum separation tower In the same way, the melt continues to advance under the action of the rotary propeller, the melt viscosity is continuously increased, and the rotation speed of the propeller is 5r/min.
- the residence time was 20 min and the final melt intrinsic viscosity was 0.79 dl/g.
- the regenerated polyester had a melting point of 264 ° C, a terminal carboxyl group content of 16 mmol/kg, and an intrinsic viscosity of 0.79 dl/g.
- sheath-core type recycled polyester staple fiber the above low-melting polyester and recycled polyester are accurately metered into the composite spinneret with a weight of 4:6 core, respectively, and the melt ejected from the spinneret of the composite component
- the core-type reclaimed polyester staple fiber can be obtained by cooling, winding, bundling, drawing, shaping, cutting and packing.
- the drying temperature of the recycled polyester is 150 ° C, the drying time is 7 h, the screw temperature is 280 ° C; the low melting point polyester spinning pipe insulation temperature is 230 ° C, the regenerated polyester spinning pipe insulation temperature is 275 ° C, the spinning box temperature It is 280 ° C; the ring air cooling cooling air temperature is 15 ° C, the wind speed is 2.0 m / s; the spinning speed is 1100 m / min; the draft ratio is 2.0, the drawing temperature is 75 ° C, and the drafting speed is 110 m / min.
- the quality index of the sheath-core type recycled polyester staple fiber obtained by the above production process is:
- regenerated low-melting polyester the mass ratio of recycled raw materials to water is 1:4; the mass ratio of recycled raw materials to potassium acetate is 100:0.5; the above raw materials are polymerized by hydrolysis to prepare regenerated low-melting polyester: hydrolysis
- the temperature is 220 ° C, the pressure is 4.5 Mpa, the reaction time is 2.8 h, and when the pressure is returned to the atmospheric pressure, the reaction product is filtered, and the obtained liquid is rotary evaporated to obtain ethylene glycol, and the filtered solid is dissolved in DMF and filtered.
- the resulting liquid was recrystallized to give terephthalic acid (TPA).
- the molar ratio of terephthalic acid (TPA) to adipic acid (AA) is 3.5:1; the molar ratio of terephthalic acid (TPA) to hexanediol (HG) is 6:1; terephthalic acid
- the molar ratio of (TPA) to ethylene glycol is 1.5:1; the molar ratio of alkyd is 1.5:1; catalyst antimony trioxide (Sb203) and cobalt acetate (Co(Ac)2) 300 ppm of the total amount of acid in the reaction system, and a stabilizer of trimethyl phosphate of 0.01% by weight (relative to the acid component) (TMP).
- the esterification reaction was carried out under nitrogen pressure at a temperature of 220 ° C, a pressure of 0.3 MPa, a reaction time of 2.5 h, a polycondensation reaction temperature of 275 ° C, a vacuum of 80 Pa, and a reaction time of 3 h.
- the melting point of the obtained low melting point polyester was The terminal carboxyl group content was 28 mmol/kg at 105 ° C, and the intrinsic viscosity was 0.67 dL/g.
- the preparation of recycled polyester the use of bottle flakes through cleaning, drum drying, multi-stage filtration, liquid phase thickening process.
- the drum drying temperature was 110 ° C
- the drying time was 7 h.
- the steps of liquid phase thickening are as follows: 1) The melt having a temperature of 270 ° C and an intrinsic viscosity of 0.55 dl / g after being melted by the screw is pumped to the vacuum separation tower by melt transfer, and the melt is at a vacuum of 100 Pa, and the temperature is At 280 ° C, the intrinsic viscosity can reach 0.68 dl / g after staying for 30 min; 2) the melt enters the secondary quenching and tempering adjustment device, the melt temperature and vacuum degree in the secondary quenching and tempering device and the vacuum separation tower In the same way, the melt continues to advance under the action of the rotary propeller, the melt viscosity is continuously increased, and the rotation speed of the propeller is 5r/min.
- the residence time was 15 min and the final melt intrinsic viscosity was 0.78 dl/g.
- the regenerated polyester had a melting point of 269 ° C, a terminal carboxyl group content of 14 mmol/kg, and an intrinsic viscosity of 0.78 dl/g.
- sheath-core type recycled polyester staple fiber the above low-melting polyester and recycled polyester are accurately metered into the composite spinneret with a 5:5 core weight, respectively, and the melt ejected from the spinneret of the composite component
- the core-type reclaimed polyester staple fiber can be obtained by cooling, winding, bundling, drawing, shaping, cutting and packing.
- the drying temperature of the recycled polyester raw material is 140 ° C, the drying time is 7.5 h, the screw temperature is 270 ° C; the low melting point polyester spinning pipe insulation temperature is 220 ° C, and the regenerated polyester spinning pipe insulation temperature is 275 ° C, the spinning box
- the body temperature was 280 ° C; the ring blowing cooling air temperature was 20 ° C, the wind speed was 3.0 m / s; the spinning speed was 1000 m / min; the draft ratio was 3.0, the drawing temperature was 70 ° C, and the drafting speed was 120 m / min.
- the quality index of the sheath-core type recycled polyester staple fiber obtained by the above production process is:
- ethylene terephthalate ethylene terephthalate
- IPA isophthalic acid
- NPG neopentyl glycol
- SB203 catalyst antimony trioxide
- Co(Ac) cobalt acetate
- TMP stabilizer trimethyl phosphate
- the obtained low melting point polyester had a melting point of 115 ° C, a terminal carboxyl group content of 30 mmol/kg, and an intrinsic viscosity of 0.68 dL/g.
- the molar amount of isophthalic acid (IPA) is the mass of the recycled raw material / 450; the molar amount of neopentyl glycol (NPG) is the mass of the recycled raw material / 960; the molar ratio of the alkyd is 1.4; the catalyst is antimony trioxide (Sb203) and cobalt acetate (Co(Ac)2)
- Sb203 antimony trioxide
- Co(Ac)2 cobalt acetate
- TMP trimethyl phosphate
- the preparation of recycled polyester the use of bottle flakes through cleaning, drum drying, multi-stage filtration, liquid phase thickening process.
- the drum drying temperature was 100 ° C
- the drying time was 7 h.
- the steps of liquid phase thickening are as follows: 1) The melt having a temperature of 270 ° C and an intrinsic viscosity of 0.55 dl / g after being melted by the screw is pumped to the vacuum separation tower by melt transfer, and the melt is at a vacuum of 100 Pa, and the temperature is At 280 ° C, the intrinsic viscosity can reach 0.68 dl / g after staying for 30 min; 2) the melt enters the secondary quenching and tempering adjustment device, the melt temperature and vacuum degree in the secondary quenching and tempering device and the vacuum separation tower In the same way, the melt continues to advance under the action of the rotary propeller, the melt viscosity is continuously increased, and the rotation speed of the propeller is 5r/min.
- the residence time was 15 min and the final melt intrinsic viscosity was 0.78 dl/g.
- the regenerated polyester had a melting point of 267 ° C, a terminal carboxyl group content of 16 mmol/kg, and an intrinsic viscosity of 0.78 dl/g.
- sheath-core type recycled polyester staple fiber the above low-melting polyester and recycled polyester are accurately metered into the composite spinneret with a weight of 6:4 core, respectively, and the melt ejected from the spinneret of the composite component
- the core-type reclaimed polyester staple fiber can be obtained by cooling, winding, bundling, drawing, shaping, cutting and packing.
- the drying temperature of the recycled polyester raw material is 140 ° C, the drying time is 7 h, the screw temperature is 280 ° C; the low melting point polyester spinning pipe insulation temperature is 230 ° C, the regenerated polyester spinning pipe insulation temperature is 270 ° C, the spinning box The temperature was 285 ° C; the ring air cooling cooling air temperature was 22 ° C, the wind speed was 2.5 m / s; the spinning speed was 900 m / min; the draft ratio was 2.5, the drawing temperature was 60 ° C, and the drafting speed was 110 m / min.
- the quality index of the sheath-core type recycled polyester staple fiber obtained by the above production process is:
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- Chemical Kinetics & Catalysis (AREA)
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- Polymers & Plastics (AREA)
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Abstract
La présente invention concerne un procédé pour produire un polyester recyclé à point de fusion à pour utilisation dans la production d'un polyester noyau-coque par dégradation hydrolytique. Le polyester recyclé à point de fusion bas est préparé à partir des matières premières suivantes au moyen de réactions de dégradation et de concentration : a. une matière première recyclée; b. de l'eau; c. un ou plusieurs parmi l'acétate de zinc, l'acétate de potassium, l'acétate de manganèse, l'acétate de magnésium, l'acétate de plomb, le chlorure de cobalt, le chlorure de cobalt, le titanate de tétrabutyle, le titanate de tétraisopropyle, et le butanediylbis-dilaurate; d. un ou plusieurs parmi l'acide isophtalique, l'acide adipique, et l'acide sébacique; f. des catalyseurs de trioxyde d'antimoine et d'acétate de cobalt; et, g. un stabilisant de phosphate de triméthyle. Le polyester recyclé à point de fusion bas de la présente invention peut être utilisé pour produire une fibre discontinue de polyester coque-noyau, et augmente la valeur ajoutée de déchets de polyester en produisant des fibres stables de polyester recyclé, et la fibre discontinue de polyester recyclé coque-noyau produite présente les avantages d'une masse stable et d'une grande qualité.
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Application Number | Priority Date | Filing Date | Title |
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CN201310091317.6A CN103145959B (zh) | 2013-03-21 | 2013-03-21 | 水解降解生产皮芯型聚酯用低熔点再生聚酯的方法 |
CN201310091317.6 | 2013-03-21 |
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PCT/CN2014/073752 WO2014146589A1 (fr) | 2013-03-21 | 2014-03-20 | Procédé pour produire un polyester recyclé à point de fusion bas pour utilisation dans la production de polyester noyau-coque par dégradation hydrolytique |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20190059670A1 (en) * | 2016-03-17 | 2019-02-28 | Eurofilters N.V. | Vacuum cleaner filter bag with recycled textile materials and/or cotton liners |
CN109467743A (zh) * | 2018-12-26 | 2019-03-15 | 李宁(中国)体育用品有限公司 | 废旧聚酯纺织品化学再生方法、再生聚酯及聚酯热熔丝 |
CN115073721A (zh) * | 2022-07-22 | 2022-09-20 | 中国石油化工股份有限公司 | 无重金属结晶型低熔点聚酯用组合物、无重金属结晶型低熔点聚酯及其制备方法及应用 |
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CN103147163B (zh) * | 2013-03-21 | 2015-03-18 | 宁波大发化纤有限公司 | 一种皮芯型再生聚酯短纤维及其制备方法 |
CN103145959B (zh) * | 2013-03-21 | 2015-08-26 | 宁波大发化纤有限公司 | 水解降解生产皮芯型聚酯用低熔点再生聚酯的方法 |
CN111138641B (zh) * | 2018-11-02 | 2021-12-21 | 中国石油化工股份有限公司 | 一种废聚酯瓶回用制备瓶级切片的方法 |
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