CN115522277A - Degradable regenerated polyester filament and production process thereof - Google Patents

Degradable regenerated polyester filament and production process thereof Download PDF

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Publication number
CN115522277A
CN115522277A CN202211236479.XA CN202211236479A CN115522277A CN 115522277 A CN115522277 A CN 115522277A CN 202211236479 A CN202211236479 A CN 202211236479A CN 115522277 A CN115522277 A CN 115522277A
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Prior art keywords
polyester
ethylene glycol
product
degradable
terephthalic acid
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CN202211236479.XA
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Chinese (zh)
Inventor
黄振
郭晓震
施文东
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Anhui Rongtai Renewable Resources Co ltd
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Anhui Rongtai Renewable Resources Co ltd
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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
    • D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/88—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polycondensation products as major constituent with other polymers or low-molecular-weight compounds
    • D01F6/92—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polycondensation products as major constituent with other polymers or low-molecular-weight compounds of 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
    • C08G63/66—Polyesters containing oxygen in the form of ether groups
    • C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/672—Dicarboxylic acids and dihydroxy compounds
    • 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
    • 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
    • C08G63/82—Preparation processes characterised by the catalyst used
    • C08G63/84—Boron, aluminium, gallium, indium, thallium, rare-earth metals, or compounds thereof
    • 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

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

Abstract

The invention relates to a degradable regenerated polyester filament and a production process thereof, belonging to the technical field of polyester materials, firstly, PET polyester is depolymerized to obtain depolymerized products; purifying the depolymerization product to remove impurities to obtain terephthalic acid and ethylene glycol; mixing terephthalic acid, ethylene glycol and an esterification catalyst, adding the mixture into a reaction vessel, and carrying out esterification reaction to obtain an esterification product; adding polyethylene glycol and a polycondensation catalyst into the esterification product to carry out polycondensation reaction to obtain a polyester product; and (3) cutting the polyester product into particles to obtain polyester chips, and then metering, extruding, cooling, stretching, heat setting, winding and ultraviolet light irradiation to obtain the degradable regenerated polyester filament. The structure and the components of the copolyester are regulated and controlled by introducing a third monomer polyethylene glycol, so that the degradability of the polyester is effectively improved; the ethylene glycol magnesium is used as a polycondensation catalyst, so that the thermal shrinkage of the polyester fiber is reduced, the heat-resistant temperature is increased, and the heat resistance and the degradability of the copolyester are effectively improved.

Description

Degradable regenerated polyester filament and production process thereof
Technical Field
The invention belongs to the technical field of polyester materials, and particularly relates to a degradable regenerated polyester filament and a production process thereof.
Background
The polyester material mainly takes polyethylene terephthalate (PET) as a main material, is a semicrystalline thermoplastic polymer material with excellent performance, is widely applied to the fields of chemical fibers, packaging, medicines, electronic machinery and the like, and when the polyester industry is rapidly developed, the polyester industry harms the ecological environment due to the long-term stable existence of the polyester industry in the nature, becomes a main component part of environment white pollution, the negative influence on the environment is intensified along with the rapid development of the industry, the treatment problem of waste polyester products ensues, and the huge inventory of the waste polyester products in the society not only brings huge pressure to the ecological environment, but also causes serious waste of resources. Therefore, the regeneration and recovery of the waste polyester products can not only change waste into valuables and relieve the pressure of resource shortage, but also have great significance in the protection of the ecological environment and the sustainable development of the polyester industry by regenerating the waste polyester into biodegradable polyester, and the like, and are also hotspots of the development of the polyester industry at present.
The recovery mode is mainly divided into physical regeneration and chemical regeneration by combining the physicochemical characteristics of the polyester. The traditional physical method realizes regeneration by carrying out melting reprocessing on the waste materials, has the characteristics of high efficiency and low cost, is the leading factor of the current polyester regeneration industrialization technology, but the product regenerated by the traditional physical method has obviously reduced quality compared with the original product, and has larger reduction and fluctuation of intrinsic viscosity. Meanwhile, because the melt viscosity is high in the process, filtration of infusible impurities and removal of volatile impurities are very difficult, and meanwhile, if excessive impurities cannot be removed in time in the high-temperature processing process, various irreversible cracking degradation is caused. Therefore, the regeneration target by the simple physical method is only limited to the waste polyester bottle chips with higher purity. The chemical regeneration is based on reversibility of polyester polycondensation reaction and nucleophilic reaction mechanism of ester exchange reaction, depolymerizes polyester into polymerization monomer or intermediate through attack of micromolecule depolymerizing agent on macromolecular chain, and carries out repolymerization after separation and purification to realize regeneration, the important basis of polyester degradation is hydrophilicity, and the degradation process is also a hydrolysis process. Because the traditional polyester material has regular chain structure and hydrophobic property, the degradation process is limited by molecular chain activity and crystal region penetrability, and hydrolysis is difficult to occur under natural conditions.
The aliphatic polyethylene glycol has a flexible hydrophilic chain, is a polymer with excellent hydrophilic performance, can be used as a third monomer block in a PET macromolecular chain segment, improves the hydrophilicity and crystallinity of copolyester, and prepares degradable polyester, however, the degradable polyester added with the third monomer has poor thermal stability due to the common special structure of the macromolecular chain.
Disclosure of Invention
In order to solve the technical problems mentioned in the background art, the invention provides a degradable regenerated polyester filament and a production process thereof.
The purpose of the invention can be realized by the following technical scheme:
a production process of degradable regenerated polyester filaments comprises the following steps:
the method comprises the following steps: dissolving an alcoholysis catalyst in a depolymerizing agent to form a depolymerized solution;
step two: putting PET polyester into a depolymerization solution, mixing and stirring, and carrying out depolymerization on the PET polyester to obtain a depolymerization product;
step three: purifying and removing impurities from the depolymerization product to obtain terephthalic acid and ethylene glycol;
step four: mixing terephthalic acid, ethylene glycol and an esterification catalyst, adding into a reaction vessel, and carrying out esterification reaction, wherein the esterification reaction end point is that the distillate of esterification water reaches more than 90% of a theoretical value, so as to obtain an esterification product;
step five: adding polyethylene glycol and a polycondensation catalyst into the esterification product to carry out polycondensation reaction to obtain a polyester product;
step six: and (3) cutting the polyester product into particles to obtain polyester chips, and then metering, extruding, cooling, stretching, heat setting, winding and ultraviolet light irradiation to obtain the degradable regenerated polyester filament.
Further, the alcoholysis catalyst in the first step is an ethylene glycol titanium alkali metal complex.
Further, the addition amount of the ethylene glycol titanium alkali metal complex is 100-200ppm.
Further, the molar ratio of the PET polyester to the depolymerization solution in the second step is (20-30): 1, the depolymerization reaction temperature is 160-220 ℃, and the reaction time is 5-8h.
Further, the purification and impurity removal in the third step comprises the following specific steps:
step A1: adding terephthalic acid dispersion liquid and ethylene glycol dispersion liquid into the depolymerization product, stirring for 1-2h under normal pressure, and filtering to remove impurities to obtain terephthalic acid-ethylene glycol solution after impurity removal;
step A2: and respectively fractionating and liquefying the terephthalic acid and the ethylene glycol in the terephthalic acid-ethylene glycol solution to obtain the terephthalic acid and the ethylene glycol.
Further, the esterification catalyst in the fourth step is one or more of zinc acetate, manganese acetate, cobalt acetate or lead acetate.
Further, the polycondensation catalyst in the fifth step is magnesium ethylene glycol.
Further, the preparation of the magnesium ethylene glycol comprises the following steps:
step B1: adding ethylene glycol into an electrolytic bath, taking magnesium chloride as electrolyte, a metal magnesium block as an anode and a stone mill as a cathode, electrifying direct current, carrying out electrolysis at the voltage of 6-10V for 10-12 hours, and taking out the electrode after the electrolysis is finished to obtain suspension;
and step B2: filtering under reduced pressure to obtain white solid, washing the white solid with absolute ethyl alcohol, and drying to obtain the ethylene glycol magnesium.
Further, the intensity of the ultraviolet light irradiated in the sixth step is 80-90MJ/cm2.
The invention also provides a degradable regenerated polyester filament which is prepared by the production process.
The invention has the beneficial effects that:
the structure and components of the copolyester are regulated and controlled by introducing the third monomer polyethylene glycol, so that the hydrophobic problem of the traditional polyester is solved, and the degradability of the polyester is effectively improved;
the ethylene glycol magnesium is used as a polycondensation catalyst, the thermal degradation coefficient is low, the generation of oligomers in the processing process is reduced, the stability of unsaturated double bonds in the polyester reaction process is ensured, the thermal shrinkage of polyester fibers is reduced, the heat-resistant temperature is improved, and the heat resistance and the degradability of the copolyester can be effectively improved.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
Preparing ethylene glycol magnesium:
step 11: adding ethylene glycol into an electrolytic cell, taking magnesium chloride as electrolyte, taking a metal magnesium block as an anode and a stone mill as a cathode, electrifying direct current, carrying out electrolysis for 12 hours at a voltage of 10V, and taking out the electrode after the electrolysis is finished to obtain suspension;
step 12: filtering under reduced pressure to obtain white solid, washing the white solid with absolute ethyl alcohol, and drying to obtain the ethylene glycol magnesium.
Example 2
Depolymerizing the PET polyester:
step 21: dissolving ethylene glycol titanium alkali metal complex into depolymerizing agent, wherein the addition amount of the ethylene glycol titanium alkali metal complex is 100-200ppm, and depolymerizing solution is formed;
step 22: putting PET polyester into a depolymerization solution, wherein the molar ratio of the PET polyester to the depolymerization solution is 20:1, mixing and stirring, and depolymerizing the PET polyester at 200 ℃ for 6 hours to obtain a depolymerized product.
Example 3
Purification and impurity removal:
step 31: adding terephthalic acid dispersion liquid and ethylene glycol dispersion liquid into the depolymerization product obtained in the example 2, wherein the molar ratio of the depolymerization product to the terephthalic acid dispersion liquid to the ethylene glycol dispersion liquid is 10;
step 32: and respectively fractionating and liquefying the terephthalic acid and the ethylene glycol in the terephthalic acid-ethylene glycol solution to obtain the terephthalic acid and the ethylene glycol.
Example 4
A production process of degradable regenerated polyester filaments comprises the following steps:
mixing terephthalic acid, ethylene glycol and zinc acetate according to a molar ratio of 100; adding polyethylene glycol and magnesium ethylene glycol into the esterification product, wherein the mass ratio of the polyethylene glycol to the magnesium ethylene glycol is 20; and (2) cutting the polyester product into particles to obtain polyester chips, and then metering, extruding, cooling, stretching, heat setting, winding and ultraviolet light irradiation are carried out, wherein the ultraviolet light intensity is 80MJ/cm & lt 2 & gt, so that the degradable regenerated polyester filament is prepared.
Example 5
A production process of degradable regenerated polyester filaments comprises the following steps:
mixing terephthalic acid, ethylene glycol and manganese acetate according to a molar ratio of 80; adding polyethylene glycol and magnesium glycol into the esterification product, wherein the mass ratio of the polyethylene glycol to the magnesium glycol is 20; and (3) cutting the polyester product into particles to obtain polyester chips, and then metering, extruding, cooling, stretching, heat setting, winding and ultraviolet irradiation are carried out, wherein the ultraviolet light intensity is 80MJ/cm & lt 2 & gt, so that the degradable regenerated polyester filament is prepared.
Example 6
A production process of degradable regenerated polyester filaments comprises the following steps:
mixing terephthalic acid, ethylene glycol and manganese acetate according to a molar ratio of 60; adding polyethylene glycol and magnesium ethylene glycol into the esterification product, wherein the mass ratio of the polyethylene glycol to the magnesium ethylene glycol is 20; and (3) cutting the polyester product into particles to obtain polyester chips, and then metering, extruding, cooling, stretching, heat setting, winding and ultraviolet irradiation are carried out, wherein the ultraviolet light intensity is 80MJ/cm & lt 2 & gt, so that the degradable regenerated polyester filament is prepared.
Example 7
A production process of degradable regenerated polyester filaments comprises the following steps:
mixing terephthalic acid, ethylene glycol and manganese acetate according to a molar ratio of 60; adding polyethylene glycol and magnesium ethylene glycol into the esterification product, wherein the mass ratio of the polyethylene glycol to the magnesium ethylene glycol is 15; and (3) cutting the polyester product into particles to obtain polyester chips, and then metering, extruding, cooling, stretching, heat setting, winding and ultraviolet irradiation are carried out, wherein the ultraviolet light intensity is 80MJ/cm & lt 2 & gt, so that the degradable regenerated polyester filament is prepared.
Example 8
A production process of degradable regenerated polyester filaments comprises the following steps:
mixing terephthalic acid, ethylene glycol and manganese acetate according to a molar ratio of 60; adding polyethylene glycol and magnesium ethylene glycol into the esterification product, wherein the mass ratio of the polyethylene glycol to the magnesium ethylene glycol is 10; and (2) cutting the polyester product into particles to obtain polyester chips, and then metering, extruding, cooling, stretching, heat setting, winding and ultraviolet light irradiation are carried out, wherein the ultraviolet light intensity is 80MJ/cm & lt 2 & gt, so that the degradable regenerated polyester filament is prepared.
Comparative example 1
The polyethylene glycol in example 5 was removed and the remaining raw materials were kept in accordance with the preparation of example 5 to obtain a control polyester filament a.
Comparative example 2
Magnesium ethylene glycol in example 5 was removed and the remaining raw materials were kept in accordance with the preparation of example 5 to obtain a control polyester filament b.
The glass transition temperature, water contact angle, and 60-day degradation rate in the soil burying test of the samples prepared in example 4 to example 8 and comparative example 1 to comparative example 2 were measured;
the test results are shown in table 1 below:
TABLE 1
Figure BDA0003883149340000071
After testing the prepared sample, the structure and components of the copolyester are regulated and controlled by introducing the third monomer polyethylene glycol into the degradable regenerated polyester filament, so that the hydrophobic problem of the traditional polyester is improved, and the degradation rate of the polyester is effectively improved; meanwhile, the ethylene glycol magnesium is used as a polycondensation catalyst, so that the stability of unsaturated double bonds in the polyester reaction process is ensured, the thermal shrinkage of polyester fibers is reduced, the glass transition temperature is increased, the heat resistance of copolyester can be effectively improved, the water contact angle is greatly reduced, and the degradability of polyester is improved.
In the description herein, references to the description of "one embodiment," "an example," "a specific example" or the like are intended to mean that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the invention. In this specification, the schematic representations of the terms used above do not necessarily refer to the same embodiment or example. Furthermore, the particular features, structures, materials, or characteristics described may be combined in any suitable manner in any one or more embodiments or examples.
The foregoing is illustrative and explanatory only, and it will be appreciated by those skilled in the art that various modifications, additions and substitutions can be made to the embodiments described without departing from the scope of the invention as defined in the appended claims.

Claims (10)

1. The production process of the degradable regenerated polyester filament is characterized by comprising the following steps:
the method comprises the following steps: dissolving an alcoholysis catalyst in a depolymerizing agent to form a depolymerized solution;
step two: putting PET polyester into a depolymerization solution, mixing and stirring, and carrying out depolymerization on the PET polyester to obtain a depolymerization product;
step three: purifying and removing impurities from the depolymerization product to obtain terephthalic acid and ethylene glycol;
step four: mixing terephthalic acid, ethylene glycol and an esterification catalyst, and then adding the mixture into a reaction vessel for esterification reaction to obtain an esterification product;
step five: adding polyethylene glycol and a polycondensation catalyst into the esterification product to carry out polycondensation reaction to obtain a polyester product;
step six: and (3) cutting the polyester product into particles to obtain polyester chips, and then carrying out metering, extrusion, cooling, stretching, heat setting, winding and ultraviolet irradiation to obtain the degradable regenerated polyester filament.
2. The process of claim 1, wherein the alcoholysis catalyst in the first step is a titanium alkali metal glycol complex.
3. A process for producing a degradable regenerated polyester filament according to claim 2, characterized in that the addition amount of the ethylene glycol titanium alkali metal complex is 100-200ppm.
4. The process for producing degradable recycled polyester filament according to claim 1, wherein the molar ratio of the PET polyester to the depolymerization solution in the second step is (20-30): 1, the depolymerization reaction temperature is 160-220 ℃, and the reaction time is 5-8h.
5. The process for producing a degradable regenerated polyester filament according to claim 1, wherein the purification and impurity removal in the third step comprises the following specific steps:
step A1: adding terephthalic acid dispersion liquid and ethylene glycol dispersion liquid into the depolymerization product, stirring for 1-2h under normal pressure, and filtering to remove impurities to obtain terephthalic acid-ethylene glycol solution after impurity removal;
step A2: and respectively fractionating and liquefying the terephthalic acid and the ethylene glycol in the terephthalic acid-ethylene glycol solution to obtain the terephthalic acid and the ethylene glycol.
6. The process for producing a degradable regenerated polyester filament according to claim 1, wherein the esterification catalyst in the fourth step is one or more of zinc acetate, manganese acetate, cobalt acetate or lead acetate, and the end point of the esterification reaction is that more than 90% of the distillate of the esterification water reaches the theoretical value.
7. The process for producing a degradable recycled polyester filament as claimed in claim 1, wherein the polycondensation catalyst in the fifth step is magnesium ethylene glycol.
8. The process for producing a degradable recycled polyester filament according to claim 7, wherein the preparation of the magnesium glycolate comprises the following steps:
step B1: adding ethylene glycol into an electrolytic cell, taking magnesium chloride as electrolyte, taking a metal magnesium block as an anode and a stone mill as a cathode, electrifying direct current, carrying out electrolysis for 10-12 hours at the voltage of 6-10V, and taking out the electrode after the electrolysis is finished to obtain suspension;
and step B2: filtering under reduced pressure to obtain white solid, washing the white solid with absolute ethyl alcohol, and drying to obtain the ethylene glycol magnesium.
9. A process for preparing degradable regenerated polyester filament according to claim 1, characterized in that the intensity of UV light irradiated in step six is 80-90MJ/cm 2 。
10. A degradable recycled polyester filament prepared by the production process according to any one of claims 1 to 9.
CN202211236479.XA 2022-10-10 2022-10-10 Degradable regenerated polyester filament and production process thereof Withdrawn CN115522277A (en)

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