WO2023038269A1 - 재활용 플라스틱 합성용 단량체 조성물, 이의 제조방법, 그리고 이를 이용한 재활용 플라스틱, 및 성형품 - Google Patents
재활용 플라스틱 합성용 단량체 조성물, 이의 제조방법, 그리고 이를 이용한 재활용 플라스틱, 및 성형품 Download PDFInfo
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- WO2023038269A1 WO2023038269A1 PCT/KR2022/010313 KR2022010313W WO2023038269A1 WO 2023038269 A1 WO2023038269 A1 WO 2023038269A1 KR 2022010313 W KR2022010313 W KR 2022010313W WO 2023038269 A1 WO2023038269 A1 WO 2023038269A1
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- monomer composition
- synthesizing
- polycarbonate
- aromatic diol
- diol compound
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- 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
- C08J11/18—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 by treatment with organic material
- C08J11/22—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 by treatment with organic material by treatment with organic oxygen-containing compounds
- C08J11/24—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 by treatment with organic material by treatment with organic oxygen-containing compounds containing hydroxyl groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
- C07C37/0555—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group being esterified hydroxy groups
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- C—CHEMISTRY; METALLURGY
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- C07C37/52—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms by splitting polyaromatic compounds, e.g. polyphenolalkanes
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- C07C37/82—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by solid-liquid treatment; by chemisorption
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- C08L2207/20—Recycled plastic
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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
- 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 a monomer composition for synthesizing recycled plastic containing a high-purity aromatic diol compound recovered through recycling of a polycarbonate-based resin through chemical decomposition, a manufacturing method thereof, recycled plastic using the same, and a molded product.
- Polycarbonate is a thermoplastic polymer and has excellent properties such as excellent transparency, ductility, and relatively low manufacturing cost.
- Chemical decomposition of polycarbonate is to obtain a monomeric aromatic diol compound (eg, Bisphenol A; BPA) through decomposition of polycarbonate, and then use it for polymerization to obtain high-purity polycarbonate.
- a monomeric aromatic diol compound eg, Bisphenol A; BPA
- Thermal decomposition, hydrolysis, and alcohol decomposition are typically known for such chemical decomposition.
- the most common method is alcohol decomposition using a base catalyst, but in the case of methanol decomposition, there is a problem in that methanol, which is harmful to the human body, is used, and in the case of ethanol, high-temperature and high-pressure conditions are required and the yield is not high.
- the present invention is to provide a monomer composition for synthesizing recycled plastic capable of securing a high purity aromatic diol compound recovered through recycling of polycarbonate-based resin by chemical decomposition.
- the present invention is to provide a method for preparing the monomer composition for synthesizing recycled plastic, recycled plastic using the monomer composition for synthesizing recycled plastic, and molded products.
- the monomer composition for synthesizing recycled plastics containing an aromatic diol compound, having a color coordinate L* of more than 95, and having an aromatic diol compound yield of 55% or more according to the following formula 1 is polycarbonate It provides a monomer composition for synthesizing recycled plastics, characterized in that it is recovered from the resin-based resin.
- W 0 is the mass of the aromatic diol compound obtained upon 100% decomposition
- W 1 is the mass of the aromatic diol compound actually obtained.
- the step of depolymerizing the polycarbonate-based resin and extracting an aromatic diol compound by adding water at least 12 times the weight of the polycarbonate-based resin to the depolymerization reaction product.
- a recycled plastic comprising a reaction product of the monomer composition for synthesizing the recycled plastic and the comonomer is also provided.
- a molded article including the recycled plastic is also provided.
- first element may also be termed a second element, and similarly, a second element may be termed a first element.
- the monomer composition for synthesizing recycled plastics includes an aromatic diol compound, has a color coordinate L* of more than 95, and has an aromatic diol compound yield of 55% or more according to Formula 1 below.
- a monomer composition for synthesizing recycled plastics, characterized in that recovered from, can be provided.
- W 0 is the mass of the aromatic diol compound obtained upon 100% decomposition
- W 1 is the mass of the aromatic diol compound actually obtained.
- the inventors of the present invention have found that the monomer composition for synthesizing recycled plastics according to one embodiment is recovered through recycling by chemical decomposition of polycarbonate-based resins, but as the aromatic diol compound, which is the main recovery target, is secured in high purity and high yield, polycarbonate-based It was confirmed through experiments that excellent physical properties can be realized during resin synthesis, and the invention was completed.
- the monomer composition for synthesizing recycled plastics comprising the monomer composition for synthesizing recycled plastics of one embodiment (composition 1) and diethyl carbonate, wherein the diethyl carbonate is recovered from polycarbonate-based resins, 2) can be simultaneously obtained in the method for preparing a monomer composition for synthesizing recycled plastics, which will be described later.
- the present invention obtains a first composition containing an aromatic diol compound in high purity by recycling a polycarbonate-based resin by chemical decomposition, and at the same time obtains a second composition containing diethyl carbonate, a high added by-product.
- Technical may have special features.
- the monomer composition for synthesizing recycled plastic of one embodiment is characterized in that it is recovered from a polycarbonate-based resin. That is, as a result of recovering the polycarbonate-based resin to obtain the monomer composition for synthesizing recycled plastics according to one embodiment, the monomer composition for synthesizing recycled plastics containing an aromatic diol compound is also obtained.
- the polycarbonate-based resin is meant to include all homopolymers or copolymers containing polycarbonate repeating units, and is a generic term for reaction products obtained through polymerization or copolymerization of monomers including an aromatic diol compound and a carbonate precursor.
- a homopolymer can be synthesized when it contains one type of carbonate repeating unit obtained by using only one type of aromatic diol compound and one type of carbonate precursor.
- the monomer one aromatic diol compound and two or more carbonate precursors are used, or two or more aromatic diol compounds and one carbonate precursor are used, or one aromatic diol compound and one carbonate precursor are used as well as one other diol.
- a copolymer can be synthesized when two or more carbonates are contained using the above.
- the homopolymer or copolymer may include all low molecular weight compounds, oligomers, and polymers according to the molecular weight range.
- the monomer composition for synthesizing recycled plastic may include an aromatic diol compound.
- aromatic diol compound bis (4-hydroxyphenyl) methane, bis (4-hydroxyphenyl) ether, bis (4-hydroxyphenyl) sulfone, bis (4-hydroxyphenyl) sulfoxide, bis (4-hydroxyphenyl) sulfide, bis (4-hydroxyphenyl) ketone, 1,1-bis (4-hydroxyphenyl) ethane, 2,2-bis (4-hydroxyphenyl) propane (bisphenol A) , 2,2-bis(4-hydroxyphenyl)butane, 1,1-bis(4-hydroxyphenyl)cyclonucleic acid (bisphenol Z), 2,2-bis(4-hydroxy-3,5-di Bromophenyl) propane, 2,2-bis (4-hydroxy-3,5-dichlorophenyl) propane, 2,2-bis (4-hydroxy-3-bromophenyl) propane, 2,2-bis (4-hydroxy-3-chlor
- the aromatic diol compound is characterized in that it is recovered from the polycarbonate-based resin used to recover the monomer composition for synthesizing recycled plastics. That is, as a result of recovering the polycarbonate-based resin to obtain the monomer composition for synthesizing recycled plastic according to one embodiment, the aromatic diol compound is also obtained. Therefore, in order to prepare the monomer composition for synthesizing recycled plastic according to one embodiment, the case where a novel aromatic diol compound is externally added apart from recovery from the polycarbonate-based resin is not included in the scope of the aromatic diol compound of the present invention.
- recovered from the polycarbonate-based resin means obtained through a depolymerization reaction of the polycarbonate-based resin.
- the depolymerization reaction may be performed under acidic, neutral, or basic conditions, and particularly, the depolymerization reaction may be performed under basic (alkaline) conditions.
- the depolymerization reaction is preferably conducted in an ethanol solvent as described below.
- the monomer composition for synthesizing recycled plastic according to one embodiment may have a color coordinate b* value of 3.5 or less, or 0.1 or more, or 0.1 to 3.5, or 1.0 to 3.5, or 2.0 to 3.5, or 2.3 to 3.1.
- the monomer composition for synthesizing recycled plastic according to one embodiment may have a color coordinate L* of greater than 95, or less than 100, or greater than 95 and less than 100, or 95.2 to 97.
- the monomer composition for synthesizing recycled plastic according to one embodiment may have a color coordinate a* of 1 or less, or 0.1 or more, or 0.1 to 1, or 0.2 to 0.6.
- color coordinates means coordinates in the CIE Lab color space, which are color values specified by CIE (Commossion International de l'Eclairage), and any position in the CIE color space is L*, It can be expressed as a*, b* three coordinate values.
- the a* value indicates whether the color with the corresponding color coordinates is biased toward pure red or pure green
- the b* value indicates whether the color with the corresponding color coordinates is pure yellow or pure yellow. Indicates which side of pure blue is biased.
- the a* value has a range of -a to +a.
- the maximum value of a* (a* max) represents pure red
- the minimum value of a* (a* min) represents pure green.
- the b* value has a range of -b to +b.
- the maximum value of b* (b* max) represents pure yellow
- the minimum value of b* (b* min) represents pure blue. For example, if the value of b* is a negative number, the color is biased towards pure blue, and if the value is positive, it means a color biased towards pure yellow.
- the color coordinate b* value of the monomer composition for synthesizing recycled plastics of the embodiment increases excessively to more than 3.5, the color coordinate L* value excessively decreases to less than 95, or the color coordinate a* value excessively increases to greater than 1,
- the color characteristics of the monomer composition for synthesizing recycled plastics of the embodiment are poor.
- An example of a method for measuring the color coordinates L*, a*, and b* values of the monomer composition for synthesizing recycled plastic according to the embodiment is not particularly limited, and various color characteristic measurement methods in the field of plastics can be applied without limitation.
- the monomer composition for synthesizing recycled plastic may have an aromatic diol compound yield of 55% or more, or 100% or less, or 55% to 100%, or 55% to 70%.
- the increase in the yield of the aromatic diol compound to 55% or more is the step of extracting the aromatic diol compound by adding water at least 12 times the weight of the polycarbonate-based resin to the depolymerization reaction product in the method for preparing a monomer composition for synthesizing recycled plastic, which will be described later. It seems to be due to the inclusion of ;
- An example of a method for measuring the aromatic diol compound yield of the monomer composition for synthesizing recycled plastic according to the embodiment is not particularly limited, and can be calculated through Equation 1 below.
- W 0 is the mass of the aromatic diol compound obtained upon 100% decomposition
- W 1 is the mass of the aromatic diol compound actually obtained.
- mass of the aromatic diol compound in Formula 1 various generally known mass measurement methods can be used without limitation, and a balance can be used, for example.
- the yield of the aromatic diol compound, which is a main recovery target material, in the monomer composition for synthesizing recycled plastic according to the embodiment is extremely increased to 55% or more, so that the efficiency of the recycling process for the polycarbonate-based resin can be improved.
- the monomer composition for synthesizing recycled plastic may have a purity of 98% or more, or 100% or less, or 98% to 100% of the aromatic diol compound.
- An example of a method for measuring the purity of the aromatic diol compound in the monomer composition for synthesizing recycled plastic according to the embodiment is not particularly limited, and for example, 1 H NMR, ICP-MS analysis, HPLC analysis, UPLC analysis, etc. can be used without limitation. can For the specific methods, conditions, equipment, etc. of NMR, ICP-MS, HPLC, and UPLC, previously known various contents can be applied without limitation.
- the monomer composition for synthesizing recycled plastics of the embodiment is 1w% Acetonitrile (ACN) at atmospheric pressure and 20 to 30 ° C.
- ACN Acetonitrile
- BPA bisphenol A
- UPLC ultra performance liquid chromatography
- the purity of the aromatic diol compound which is the main recovery target material, is extremely increased to 98% or more, thereby minimizing other impurities, thereby realizing excellent physical properties when synthesizing polycarbonate-based resins using this this is possible
- diethyl carbonate may be obtained as a by-product.
- the diethyl carbonate is characterized in that it is recovered from the polycarbonate-based resin used for recovering the monomer composition for synthesizing recycled plastic according to the embodiment.
- diethyl carbonate is also obtained. Therefore, in order to prepare the monomer composition for synthesizing recycled plastic according to the embodiment, the case where new diethyl carbonate is externally added separately from recovery from the polycarbonate-based resin is not included in the diethyl carbonate category of the embodiment. .
- recovered from the polycarbonate-based resin means obtained through a depolymerization reaction of the polycarbonate-based resin.
- the depolymerization reaction may be carried out under acidic, neutral or basic conditions, and in particular, the depolymerization reaction may proceed under basic (alkaline) conditions.
- the depolymerization reaction is preferably conducted in an ethanol solvent as described below.
- the diethyl carbonate can be separated and recovered as a by-product from the monomer composition for synthesizing recycled plastics of the embodiment.
- the monomer composition for synthesizing recycled plastic may be used as a raw material for producing various recycled plastics (eg, polycarbonate (PC)) described below.
- PC polycarbonate
- the monomer composition for synthesizing recycled plastics of the embodiment may further include some small amounts of other additives and solvents, and the type of specific additives or solvents is not greatly limited, and an aromatic diol compound recovery process by depolymerization of polycarbonate-based resin Various materials widely used in can be applied without limitation.
- the monomer composition for synthesizing recycled plastics according to one embodiment may be obtained by a method for preparing a monomer composition for synthesizing recycled plastics described below. That is, the monomer composition for synthesizing recycled plastic according to an embodiment of the present invention is obtained through various filtration, purification, washing, and drying processes in order to secure only aromatic diol compounds, which are the main recovery target materials, in high purity after the depolymerization reaction of the polycarbonate-based resin. applicable
- the step of depolymerizing the polycarbonate-based resin and extracting an aromatic diol compound by adding 12 times or more water to the weight of the polycarbonate-based resin to the depolymerization reaction product.
- the present inventors extract an aromatic diol compound using a specific amount of water, so in the present invention It was confirmed through experiments that an aromatic diol compound, which is a major synthetic target material, can be obtained in high purity and in high yield, and the present invention was completed.
- the method for preparing a monomer composition for synthesizing recycled plastic may include a step of depolymerizing a polycarbonate-based resin.
- the polycarbonate-based resin is meant to include all homopolymers or copolymers containing polycarbonate repeating units, and is a generic term for reaction products obtained through polymerization or copolymerization of monomers including an aromatic diol compound and a carbonate precursor.
- a homopolymer can be synthesized when it contains one type of carbonate repeating unit obtained by using only one type of aromatic diol compound and one type of carbonate precursor.
- the monomer one aromatic diol compound and two or more carbonate precursors are used, or two or more aromatic diol compounds and one carbonate precursor are used, or one aromatic diol compound and one carbonate precursor are used as well as one other diol.
- a copolymer can be synthesized when two or more carbonates are contained using the above.
- the homopolymer or copolymer may include all low molecular weight compounds, oligomers, and polymers according to the molecular weight range.
- the polycarbonate-based resin can be applied regardless of various forms and types, such as a new polycarbonate-based resin produced through synthesis, a recycled polycarbonate-based resin produced through a recycling process, or polycarbonate-based resin waste.
- the efficiency of the process of recovering the aromatic diol compound and the carbonate precursor from the polycarbonate resin may be increased by performing a pretreatment process of the polycarbonate resin before proceeding with the depolymerization reaction of the polycarbonate resin.
- the pretreatment process include washing, drying, pulverization, and decomposition of a glycol, and the specific method of each pretreatment process is not limited, and an aromatic diol compound by depolymerization of polycarbonate-based resin, and a carbonate precursor recovery process Various methods widely used in can be applied without limitation.
- the depolymerization reaction may be performed under acidic, neutral, or basic conditions, and particularly, the depolymerization reaction may proceed under basic (alkaline) conditions.
- the type of the base is not particularly limited, and examples thereof include sodium hydroxide (NaOH) or potassium hydroxide (KOH).
- the base is a base catalyst that acts as a catalyst, and has an advantage in economic efficiency compared to organic catalysts mainly used under mild conditions.
- the depolymerization reaction of the polycarbonate-based resin may proceed in a solvent including ethanol.
- the present invention has the advantage of being able to stably obtain bisphenol A, which is a high-purity monomer, by decomposing a polycarbonate-based resin with a solvent including ethanol, and additionally obtaining high value-added diethyl carbonate as a reaction by-product.
- the amount of ethanol may be 5 to 15 moles or 8 to 13 moles per mole of the polycarbonate-based resin. Since the ethanol has good solubility in bisphenol A, ethanol within the above range must be necessarily included. When the content of ethanol is excessively reduced to less than 5 moles relative to 1 mole of the polycarbonate-based resin, alcohol decomposition of the polycarbonate-based resin is difficult to sufficiently proceed. On the other hand, if the content of ethanol is excessively increased to more than 15 moles relative to 1 mole of the polycarbonate-based resin, the economic feasibility of the process may decrease due to excessive use of alcohol.
- the solvent in which the depolymerization reaction of the polycarbonate-based resin proceeds is at least one selected from the group consisting of tetrahydrofuran, toluene, methylene chloride, chloroform, dimethyl carbonate, ethylmethyl carbonate, diethyl carbonate and dipropyl carbonate, in addition to ethanol.
- An organic solvent may be further included.
- the organic solvent may include tetrahydrofuran, toluene, methylene chloride, chloroform, dimethyl carbonate, ethylmethyl carbonate, diethyl carbonate, dipropyl carbonate, or a mixture of two or more thereof.
- methylene chloride may be used as the organic solvent.
- methylene chloride is used as an organic solvent mixed with ethanol, there is an advantage in that the solubility of polycarbonate is improved and reactivity can be improved.
- the amount of the organic solvent may be 16 to 20 moles, or 16 to 18 moles based on 1 mole of the polycarbonate-based resin. In addition, the amount of the organic solvent may be 1.5 to 2 moles based on 1 mole of the total amount of ethanol.
- the temperature at which the depolymerization of the polycarbonate-based resin proceeds is not particularly limited, but may be, for example, 20 °C to 100 °C or 50 °C to 70 °C.
- the depolymerization reaction of the polycarbonate-based resin may proceed for 1 hour to 30 hours, or 4 hours to 6 hours.
- the present invention controls the type and amount of the mixed solvent and the type and content of the base catalyst even without using an organic catalyst, so that a high-purity aromatic diol compound (e.g., Bisphenol A) can be obtained, and diethyl carbonate can be obtained as a by-product by using an ethanol solvent.
- a high-purity aromatic diol compound e.g., Bisphenol A
- diethyl carbonate can be obtained as a by-product by using an ethanol solvent.
- the step of depolymerizing the polycarbonate-based resin may include a first step of dissolving the carbonate-based resin in an organic solvent; and a second step of stirring by adding a catalyst solution including ethanol and a base.
- a catalyst solution including ethanol and a base.
- the step of neutralizing the depolymerization reaction product with an acid is performed. can include more.
- the alkaline decomposition product of the polycarbonate-based resin includes an aromatic diol compound or a salt thereof, but since the main recovery target material of the present invention is an aromatic diol compound, in the case of the salt of the aromatic diol compound obtained by the alkaline decomposition, additional It can be converted into an aromatic diol compound through neutralization with an acid. That is, when the depolymerization reaction of the polycarbonate-based resin is alkali decomposition, a neutralization reaction step by acid may be performed.
- a strong acid may be used as the acid used during the neutralization reaction, and examples thereof include hydrochloric acid (HCl). Due to the neutralization reaction by the strong acid, pH may satisfy 4 or less or 2 or less at the end of the neutralization reaction. During the neutralization reaction, the temperature may be adjusted to 25° C. or higher and 100° C. or lower.
- hydrochloric acid HCl
- a step of removing residual impurities through filtration or adsorption may be additionally performed.
- the liquid containing the aromatic diol compound may be recovered by separating the water layer and the organic layer and filtering the organic layer through vacuum filtration.
- an adsorbent is added to the depolymerization product prior to the step of extracting an aromatic diol compound by adding water at least 12 times the weight of the polycarbonate-based resin to the depolymerization product.
- a step of removing the adsorbent after adsorption purification by adding a; may further include.
- the depolymerization product may be brought into contact with the adsorbent.
- activated carbon As an example of the adsorbent, activated carbon, charcoal, or a mixture thereof may be used.
- the activated carbon is a black carbon material with micropores prepared by subjecting raw materials to a carbonization process at about 500 ° C and an activated carbon process at about 900 ° C.
- various activated carbons such as plant-based, coal-based, petroleum-based, and waste activated carbons can be applied without limitation.
- plant-based activated carbon may include coconut activated carbon, wood activated carbon, and sawdust activated carbon.
- coal-based activated carbon lignite activated carbon, bituminous carbon activated carbon, and anthracite activated carbon may be mentioned.
- petroleum-based activated carbon includes petroleum coke activated carbon and oil carbon activated carbon.
- waste activated carbon synthetic resin activated carbon and pulp activated carbon may be mentioned.
- the adsorbent may include at least one type of activated carbon selected from the group consisting of plant-based activated carbon, coal-based activated carbon, petroleum-based activated carbon, and waste activated carbon. That is, the adsorbent may include plant-based activated carbon, coal-based activated carbon, petroleum-based activated carbon, waste activated carbon, or a mixture of two or more thereof.
- the adsorbent may include at least one type of activated carbon selected from the group consisting of coconut activated carbon, lignite activated carbon, anthracite activated carbon, and bituminous carbon activated carbon. That is, the adsorbent may include coconut activated carbon, lignite activated carbon, anthracite activated carbon, bituminous carbon activated carbon, or a mixture of two or more thereof.
- Adsorption purification conditions by the adsorbent are not particularly limited, and various conventional adsorption purification conditions may be used without limitation.
- the input amount of the adsorbent may be 40% to 60% by weight compared to the polycarbonate-based resin
- the adsorption time may be 1 hour to 5 hours
- the adsorption method may be agitated adsorption or an adsorption tower for Lab.
- the method for preparing a monomer composition for synthesizing recycled plastic may include extracting an aromatic diol compound by adding water at least 12 times the weight of the polycarbonate-based resin to the depolymerization reaction product.
- the aromatic diol compound is extracted using a specific amount of water, it is possible to secure the aromatic diol compound, which is the main synthetic target material, in high purity and high yield in the present invention.
- the water layer (2) may be formed while the aromatic diol compound is precipitated as a solid between the depolymerization reaction product 1 and the depolymerization reaction product 1 .
- the aromatic diol compound precipitated as a solid may be filtered through a filter to extract the aromatic diol compound (4).
- the depolymerization reaction product of the polycarbonate-based resin includes an aromatic diol compound or a salt thereof and a carbonate precursor.
- the contents of the aromatic diol compound and the carbonate precursor include all of the above-mentioned contents in the embodiment.
- the aromatic diol compound can be extracted by adding 1 to 20 times, or 14 to 20 times, or 15 to 20 times, or 16 to 20 times of water.
- the weight of the polycarbonate-based resin is 100 g, for example, when the aromatic diol compound is extracted, 1200 g or more of water, which is 12 times the weight of the polycarbonate-based resin, may be added.
- the amount of water added during extraction of the aromatic diol compound is too small to be less than 12 times the weight of the polycarbonate-based resin, the aromatic diol compound may not be sufficiently extracted and the yield may decrease.
- the amount of water added during extraction of the aromatic diol compound is excessively increased to more than 20 times the weight of the polycarbonate-based resin, excessive water is required and the efficiency of the extraction process may decrease.
- the number of times of adding water is 1 to 10 times, or 2 to 10 times, Or 3 to 10 times, or 4 to 10 times, or 1 to 8 times, or 2 to 8 times, or 3 to 8 times, or 4 to 8 times. If the number of times the water is added is 2 or more, the water is repeatedly added, and when the number of times the water is added is 2 to 10 times, removing the water between the steps of adding water. may further include.
- water twice the weight of the polycarbonate-based resin is added to the depolymerization reaction product 6 times to 10 times, or 6 to 8 times.
- water 4 times the weight of the polycarbonate-based resin is added to the depolymerization reaction product 3 to 5 times. It may include the step of adding repeatedly, or 3 to 6 times.
- the step of extracting an aromatic diol compound by adding 12 times or more of water to the weight of the polycarbonate-based resin to the depolymerization reaction product includes adding water of 12 times the weight of the polycarbonate-based resin to the depolymerization reaction product once. steps may be included.
- the method for preparing a monomer composition for synthesizing recycled plastic may further include a step of purifying the extracted aromatic diol compound. Through this, an aromatic diol compound, which is a main recovery material, is obtained, which corresponds to the embodiment of the monomer composition for synthesizing recycled plastic.
- the step of purifying the extracted aromatic diol compound may include a step of washing the extracted aromatic diol compound.
- washing is performed to sufficiently remove them to secure a high-purity aromatic diol compound.
- the washing step may include washing with a solvent at a temperature of 10 ° C. or more and 30 ° C. or less, or 20 ° C. or more and 30 ° C. or less; and washing with a solvent at a temperature of 40 °C or more and 80 °C or less, or 40 °C or more and 60 °C or less, or 45 °C or more and 55 °C or less.
- the temperature condition refers to the temperature inside the washing vessel at which washing with the solvent is performed, and various heating mechanisms may be applied without limitation to maintain a high temperature beyond room temperature.
- the step of washing with a solvent at a temperature of 10 ° C. or more and 30 ° C. or less may be performed first, and the step of washing with a solvent at a temperature of 40 ° C. or more and 80 ° C. or less may be performed later.
- the step of washing with a solvent at a temperature of 40 ° C. or more and 80 ° C. or less may be performed first, and the step of washing with a solvent at a temperature of 10 ° C. or more and 30 ° C. or less may be performed later.
- the washing with a solvent at a temperature of 10 ° C. or more and 30 ° C. or less may be performed first, and the washing with a solvent at a temperature of 40 ° C. or more and 80 ° C. or less may be performed later. there is. Accordingly, corrosion of the reactor by strong acid after the neutralization step can be minimized.
- Washing with a solvent at a temperature of 10 ° C. or more and 30 ° C. or less; And washing with a solvent at a temperature of 40 ° C. or more and 80 ° C. or less may be repeated at least once or more.
- the difference between the temperature of washing with a solvent at a temperature of 40 ° C. or more and 80 ° C. or less and the temperature of washing with a solvent at a temperature of 10 ° C. or more and 30 ° C. or less is 20 ° C. or more and 50 ° C. or less.
- the difference between the temperature in the step of washing with a solvent at a temperature of 40 ° C or more and 80 ° C or less and the temperature in the step of washing with a solvent at a temperature of 10 ° C or more and 30 ° C or less is the temperature of 40 ° C or more and 80 ° C or less. It means a value obtained by subtracting the temperature of washing with a solvent from the temperature of 10 ° C. or more and 30 ° C. or less from the temperature of washing with a solvent in .
- the solvent used in the washing step may include one of water, alcohol, and an organic solvent.
- organic solvent tetrahydrofuran, toluene, methylene chloride, chloroform, dimethyl carbonate, ethylmethyl carbonate, diethyl carbonate, dipropyl carbonate, or a mixture of two or more thereof may be used.
- the solvent used in the washing step may be used in a weight ratio of 1 part by weight or more and 30 parts by weight or less, or 1 part by weight or more and 10 parts by weight or less, based on 1 part by weight of the polycarbonate-based resin used in the depolymerization reaction.
- the solvent in the step of washing with a solvent at a temperature of 10 ° C. or more and 30 ° C. or less may be an organic solvent.
- Methylene chloride may be preferably used as the organic solvent.
- the organic solvent may be used in an amount of 1 part by weight or more and 10 parts by weight or less based on 1 part by weight of the polycarbonate-based resin.
- the solvent in the step of washing with a solvent at a temperature of 40 ° C. or more and 80 ° C. or less may be water.
- the solvent may be used in an amount of 1 part by weight or more and 10 parts by weight or less based on 1 part by weight of the polycarbonate-based resin.
- a drying step may further include.
- the remaining solvent may be removed through the drying, and specific drying conditions are not particularly limited, but drying may be performed at a temperature of, for example, 10 °C to 100 °C or 10 °C to 50 °C.
- specific drying equipment and method used in the drying various previously known drying techniques can be applied without limitation.
- recycled plastic including the reaction product of the monomer composition for synthesizing recycled plastic and the comonomer of one embodiment may be provided.
- Information about the monomer composition for synthesizing recycled plastics according to one embodiment includes all of the above-described contents in the one embodiment and the other embodiments, respectively.
- Examples corresponding to the recycled plastic are not particularly limited, and various plastics synthesized with aromatic diol compounds such as bisphenol A as monomers can be applied without limitation, and more specific examples include polycarbonate-based resins.
- the polycarbonate-based resin is meant to include all homopolymers or copolymers containing polycarbonate repeating units, and is a generic term for reaction products obtained through polymerization or copolymerization of monomers including an aromatic diol compound and a carbonate precursor.
- a homopolymer can be synthesized when it contains one type of carbonate repeating unit obtained by using only one type of aromatic diol compound and one type of carbonate precursor.
- the monomer one aromatic diol compound and two or more carbonate precursors are used, or two or more aromatic diol compounds and one carbonate precursor are used, or one aromatic diol compound and one carbonate precursor are used as well as one other diol.
- a copolymer can be synthesized when two or more carbonates are contained using the above.
- the homopolymer or copolymer may include all low molecular weight compounds, oligomers, and polymers according to the molecular weight range.
- a carbonate precursor may be used as the comonomer.
- the carbonate precursor include phosgene, triphosgene, diphosgene, bromophosgene, dimethyl carbonate, diethyl carbonate, dibutyl carbonate, dicyclohexyl carbonate, diphenyl carbonate, ditoryl carbonate, bis(chlorophenyl) carbonate, m - Cresyl carbonate, dinaphthyl carbonate, bis(diphenyl) carbonate or bishaloformate may be mentioned.
- Examples of the reaction process of the monomer composition and comonomer for synthesis are not greatly limited, and various previously known polycarbonate manufacturing methods are applicable without limitation.
- a polycarbonate manufacturing method including polymerizing a composition including a monomer composition for synthesizing recycled plastic and a comonomer may be used.
- the polymerization may be performed by interfacial polymerization, and during the interfacial polymerization, the polymerization reaction is possible at normal pressure and low temperature, and the molecular weight can be easily controlled.
- the polymerization temperature may be 0 °C to 40 °C, and the reaction time may be 10 minutes to 5 hours.
- the pH may be maintained at 9 or higher or 11 or higher during the reaction.
- the solvent that can be used for the polymerization is not particularly limited as long as it is a solvent used for polymerization of polycarbonate in the art, and for example, halogenated hydrocarbons such as methylene chloride and chlorobenzene can be used.
- the polymerization may be performed in the presence of an acid binder, and an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide or an amine compound such as pyridine may be used as the acid binder.
- an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide or an amine compound such as pyridine may be used as the acid binder.
- polymerization may be performed in the presence of a molecular weight regulator.
- Alkylphenols having 1 to 20 carbon atoms may be used as the molecular weight modifier, and specific examples thereof include p-tert-butylphenol, p-cumylphenol, decylphenol, dodecylphenol, tetradecylphenol, hexadecylphenol, octadecylphenol, eicosylphenol, docosylphenol or triacontylphenol.
- the molecular weight modifier may be added before polymerization, during polymerization, or after polymerization.
- the molecular weight modifier may be used in an amount of 0.01 to 10 parts by weight or 0.1 to 6 parts by weight based on 100 parts by weight of the aromatic diol compound, and a desired molecular weight may be obtained within this range.
- reactions such as tertiary amine compounds such as triethylamine, tetra-n-butylammonium bromide, and tetra-n-butylphosphonium bromide, quaternary ammonium compounds, and quaternary phosphonium compounds Accelerators may additionally be used.
- a molded article including the recycled plastic of the other embodiment may be provided.
- the contents of the recycled plastic include all of the contents described above in the other embodiment.
- the molded product may be obtained by applying various known plastic molding methods to the recycled plastic without limitation, and examples of the molding method include injection molding, foam injection molding, blow molding, or extrusion molding.
- Examples of the molded article are not greatly limited, and can be applied without limitation to various molded articles using plastic.
- Examples of the molded article include automobile parts, electrical and electronic products, communication products, household goods, building materials, optical parts, exterior materials, and the like.
- the molded article may optionally contain one or more additives selected from the group consisting of antioxidants, plasticizers, antistatic agents, nucleating agents, flame retardants, lubricants, impact modifiers, optical whitening agents, ultraviolet absorbers, pigments, and dyes. may additionally include.
- the method for manufacturing the molded product after mixing the recycled plastic and additives of the other embodiment using a mixer, extruding them with an extruder to produce pellets, drying the pellets, and then injecting them with an injection molding machine can include
- a monomer composition for synthesizing recycled plastic containing a high-purity aromatic diol compound recovered through recycling by chemical decomposition of a polycarbonate-based resin, a manufacturing method thereof, and a recycled plastic using the same, and a molded product can be provided there is.
- charcoal was added as an adsorbent to the product whose pH was lowered to less than 2 at a rate of 50% by weight relative to waste polycarbonate, purified through adsorption for 3 hours, and then filtered using Celite, adsorbent has been removed.
- Example 1 (3-2. Purification-Extraction Step), after adding water twice the weight of waste polycarbonate and stirring, the extraction process of removing the water layer was repeated 6 times, and the weight of waste polycarbonate A recycled bisphenol A monomer composition was prepared in the same manner as in Example 1, except that twice as much water was added once more.
- Example 1 (3-2. Purification-extraction step), after adding water twice the weight of waste polycarbonate and stirring, the extraction process of removing the water layer was repeated 7 times, and the weight of waste polycarbonate A recycled bisphenol A monomer composition was prepared in the same manner as in Example 1, except that twice as much water was added once more.
- Example 1 (3-2. Purification-extraction step), after adding and stirring water four times the weight of waste polycarbonate, the extraction process of removing the water layer was repeated twice, and the weight of waste polycarbonate A recycled bisphenol A monomer composition was prepared in the same manner as in Example 1, except that 4 times the amount of water was added once more.
- Example 1 (3-2. Purification-Extraction Step), after adding and stirring water 12 times the weight of waste polycarbonate, bisphenol A (BPA) crystallized between the water layer and the MC layer was formed, A recycled bisphenol A monomer composition was prepared in the same manner as in Example 1, except that bisphenol A (BPA) was recovered through vacuum filtration.
- BPA bisphenol A
- Example 1 (3-2. Purification-extraction step), the extraction process of adding and stirring twice the weight of waste polycarbonate and removing the water layer was repeated 4 times, and the weight of waste polycarbonate A recycled bisphenol A monomer composition was prepared in the same manner as in Example 1, except that twice the amount of water was added once more and left for 4 to 5 hours.
- Example 4 (3-2. Purification-extraction step), after adding and stirring water 4 times the weight of waste polycarbonate, an extraction step of removing the water layer was performed once, and the weight of waste polycarbonate A recycled bisphenol A monomer composition was prepared in the same manner as in Example 1, except that 4 times the amount of water was added once more and left for 4 to 5 hours.
- the recycled bisphenol A monomer composition was analyzed in reflection mode using a HunterLab UltraScan PRO spectrophotometer.
- W 0 is the mass of BPA obtained upon 100% decomposition
- the recycled bisphenol A monomer compositions obtained in Examples 1 to 5 exhibited a high purity of 98% to 99.3%.
- the recycled bisphenol A monomer compositions obtained in Examples 1 to 5 exhibited excellent optical properties, with color coordinates L* ranging from 95.22 to 96.11, a* ranging from 0.29 to 0.54, and b* ranging from 2.33 to 3.07.
- the recycled bisphenol A monomer composition obtained in Examples 1 to 5 showed a high BPA yield of 59% to 69%.
- the recycled bisphenol A monomer composition obtained in Comparative Examples 1 to 2 had a BPA yield of 42% to 50%. % was lowered compared to the examples.
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Abstract
Description
구분 | 추출조건 | 재활용 비스페놀A 단량체 조성물 | ||||
순도(%) | L* | a* | b* | 수율(%) | ||
실시예1 | 물(PC 중량의 2배)/6회 | 99.3 | 96.10 | 0.30 | 2.34 | 69 |
실시예2 | 물(PC 중량의 2배)/7회 | 99.2 | 96.07 | 0.32 | 2.36 | 64 |
실시예3 | 물(PC 중량의 2배)/8회 | 99.3 | 96.11 | 0.29 | 2.33 | 60 |
실시예4 | 물(PC 중량의 4배)/3회 | 98.6 | 95.40 | 0.48 | 2.79 | 62 |
실시예5 | 물(PC 중량의 12배)/1회 | 98.0 | 95.22 | 0.54 | 3.07 | 59 |
비교예1 | 물(PC 중량의 2배)/5회 | 98.9 | 95.64 | 0.38 | 2.66 | 50 |
비교예2 | 물(PC 중량의 4배)/2회 | 96.8 | 94.89 | 0.61 | 3.59 | 42 |
Claims (20)
- 방향족 디올 화합물을 포함하고,색좌표 L*이 95 초과이고,하기 식1에 의한 방향족 디올 화합물 수율이 55% 이상이고,상기 재활용 플라스틱 합성용 단량체 조성물은 폴리카보네이트계 수지에서 회수된 것을 특징으로 하는, 재활용 플라스틱 합성용 단량체 조성물:[식 1]수율(%) = W1/W0상기 식 1에서, W0 는 100% 분해 시 수득되는 방향족 디올 화합물 질량이고, W1는 실제 수득한 방향족 디올 화합물 질량이다.
- 제1항에 있어서,상기 재활용 플라스틱 합성용 단량체 조성물의 색좌표 b*가 3.5 이하인, 재활용 플라스틱 합성용 단량체 조성물.
- 제1항에 있어서,상기 재활용 플라스틱 합성용 단량체 조성물의 색좌표 a*가 1 이하인, 재활용 플라스틱 합성용 단량체 조성물.
- 제1항에 있어서,상기 방향족 디올 화합물은 폴리카보네이트계 수지에서 회수된 것을 특징으로 하는, 재활용 플라스틱 합성용 단량체 조성물.
- 제1항에 있어서,상기 재활용 플라스틱 합성용 단량체 조성물은 방향족 디올 화합물 순도가 98% 이상인, 재활용 플라스틱 합성용 단량체 조성물.
- 제1항에 있어서,디에틸 카보네이트가 부산물로서 얻어지고, 상기 디에틸 카보네이트는 폴리카보네이트계 수지에서 회수된 것을 특징으로 하는, 재활용 플라스틱 합성용 단량체 조성물.
- 폴리카보네이트계 수지를 해중합반응시키는 단계; 및상기 해중합반응 생성물에 폴리카보네이트계 수지 중량의 12배 이상의 물을 첨가하여, 방향족 디올 화합물을 추출하는 단계;를 포함하는, 재활용 플라스틱 합성용 단량체 조성물의 제조방법.
- 제7항에 있어서,상기 해중합반응 생성물에 폴리카보네이트계 수지 중량의 12배 이상의 물을 첨가하여, 방향족 디올 화합물을 추출하는 단계에서,물을 첨가하는 횟수가 1회 내지 10회인, 재활용 플라스틱 합성용 단량체 조성물의 제조방법.
- 제8항에 있어서,상기 물을 첨가하는 횟수가 2회 내지 10회 반복하여 첨가시,물을 첨가하는 단계 사이에 물을 제거하는 단계를 더 포함하는, 재활용 플라스틱 합성용 단량체 조성물의 제조방법.
- 제7항에 있어서,상기 해중합반응 생성물에 폴리카보네이트계 수지 중량의 12배 이상의 물을 첨가하여, 방향족 디올 화합물을 추출하는 단계는,상기 해중합반응 생성물에 폴리카보네이트계 수지 중량의 2배의 물을 6회 내지 10회 반복하여 첨가하는 단계를 포함하는, 재활용 플라스틱 합성용 단량체 조성물의 제조방법.
- 제7항에 있어서,상기 해중합반응 생성물에 폴리카보네이트계 수지 중량의 12배 이상의 물을 첨가하여, 방향족 디올 화합물을 추출하는 단계는,상기 해중합반응 생성물에 폴리카보네이트계 수지 중량의 4배의 물을 3회 내지 5회 반복하여 첨가하는 단계를 포함하는, 재활용 플라스틱 합성용 단량체 조성물의 제조방법.
- 제7항에 있어서,상기 추출된 방향족 디올 화합물의 정제단계를 더 포함하는, 재활용 플라스틱 합성용 단량체 조성물의 제조방법.
- 제12항에 있어서,상기 추출된 방향족 디올 화합물의 정제단계는, 상기 추출된 방향족 디올 화합물의 세척단계를 포함하는, 재활용 플라스틱 합성용 단량체 조성물의 제조방법.
- 제13항에 있어서,상기 세척 단계는, 10 ℃ 이상 30 ℃ 이하의 온도에서 용매로 세척하는 단계; 및 40 ℃ 이상 80 ℃ 이하의 온도에서 용매로 세척하는 단계;를 포함하는 재활용 플라스틱 합성용 단량체 조성물의 제조방법.
- 제14항에 있어서,상기 10 ℃ 이상 30 ℃ 이하의 온도에서 용매로 세척하는 단계의 용매는 유기용매인 재활용 플라스틱 합성용 단량체 조성물의 제조방법.
- 제14항에 있어서,상기 40 ℃ 이상 80 ℃ 이하의 온도에서 용매로 세척하는 단계의 용매는 물인 재활용 플라스틱 합성용 단량체 조성물의 제조방법.
- 제14항에 있어서,상기 40 ℃ 이상 80℃ 이하의 온도에서 용매로 세척하는 단계의 온도와, 상기 10 ℃ 이상 30 ℃ 이하의 온도에서 용매로 세척하는 단계의 온도간 차이값이 20 ℃ 이상 50 ℃ 이하인, 재활용 플라스틱 합성용 단량체 조성물의 제조방법.
- 제7항에 있어서,상기 해중합반응 생성물에 폴리카보네이트계 수지 중량의 12배 이상의 물을 첨가하여, 방향족 디올 화합물을 추출하는 단계 이전에,상기 해중합반응 생성물에 흡착제를 첨가하여 흡착정제시킨 후 흡착제를 제거하는 단계;를 더 포함하는, 재활용 플라스틱 합성용 단량체 조성물의 제조방법.
- 제1항의 재활용 플라스틱 합성용 단량체 조성물 및 공단량체의 반응생성물을 포함하는, 재활용 플라스틱.
- 제19항의 재활용 플라스틱을 포함하는, 성형품.
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
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CN202280007281.6A CN116615492A (zh) | 2021-09-13 | 2022-07-14 | 用于合成再生塑料的单体组合物、其制备方法、以及再生塑料、使用其的模制品 |
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US18/032,141 US20230382837A1 (en) | 2021-09-13 | 2022-07-14 | Monomer composition for synthesizing recycled plastic, preparation method thereof, recycled plastic, and molded product using the same |
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EP (6) | EP4209528A4 (ko) |
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