Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
  • C07C41/01—Preparation of ethers
  • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
  • C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C43/00—Ethers; Compounds having groups, groups or groups
  • C07C43/02—Ethers
  • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
  • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
• • 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

Definitions

• the present invention relates to a novel method for decomposing a polycarbonate resin capable of efficiently recovering a bisphenoxy alcohol fluorene as a starting material from waste polycarbonate resin having a fluorene structure with high purity.
• Polycarbonate resins having a fluorene structure are relatively excellent in high refractive index properties, low birefringence properties, transparency, processability, and heat resistance, and in recent years as optical resin materials such as optical lenses and optical films.
• the usage is increasing.
• since the amount of resin to be discarded increases as the demand for polycarbonate resin containing a fluorene structure increases, it has become important to reuse them.
• bisphenoxy alcohol fluorenes which are one of the starting materials, are more expensive than other materials, and therefore development of a method for efficiently recovering them as reusable materials has been desired.
• Methods for depolymerizing the polycarbonate resin include mainly the phenol decomposition method in which the polycarbonate resin is converted to bisphenol A and diphenyl carbonate by heating with phenol, and both are separated and recovered by distillation, in the presence of a base catalyst.
• the polycarbonate resin and lower alcohol are converted into bisphenol A and dialkyl carbonate by heat treatment, and the alcohol decomposition method in which both are separated and recovered by distillation.
• the polycarbonate resin is reacted with excess alkaline aqueous solution to decompose into bisphenol A.
• a by-product such as diphenyl carbonate or dialkyl carbonate is produced, and the desired bisphenols are separated and recovered. Becomes complicated.
• Patent Document 1 As a method for depolymerizing a polycarbonate resin by a hydrolysis method, for example, in Japanese Patent Publication No. 40-16536 (Patent Document 1), a polycarbonate resin and a 1 to 30% aqueous alkali solution are placed in a pressure-resistant container, and preferably 100 ° C. or higher, preferably A method of hydrolyzing at 150 ° C. or higher is disclosed.
• Patent Document 2 discloses a method in which a part or all of waste aromatic polycarbonate resin is dissolved in an organic solvent composed of a chlorinated compound and then decomposed with an aqueous metal hydroxide solution. .
• Patent Document 1 requires severe reaction conditions such as a high temperature reaction and a high pressure reaction.
• the organic solvent which consists of chlorinated compounds, such as a methylene chloride is essential, and there is a concern about safety.
• special equipment is required for production using chlorinated compounds.
• these conventional methods are depolymerization methods suitable for recovering bisphenol A from a polycarbonate resin using 2,2-bis (4-hydroxyphenyl) propane (commonly called bisphenol A) as a raw material.
• An object of the present invention is to provide a depolymerization method for industrially efficiently recovering bisphenoxy alcohol fluorenes, which are starting material materials having a specific structure, from a polycarbonate resin having a fluorene structure.
• the present inventors have determined that a polycarbonate resin having a fluorene structure produced using bisphenoxy alcohol fluorenes as a starting material can be used in the presence or absence of a specific organic solvent. It was found that the polycarbonate resin can be efficiently depolymerized by reacting with an aqueous metal hydroxide solution under mild conditions, and high-quality bisphenoxy alcohol fluorenes can be recovered. It came to be completed.
• the present invention includes the following.
• a depolymerization characterized in that a polycarbonate resin having a fluorene structure is hydrolyzed at a temperature of 120 ° C. or lower in the presence of an aqueous metal hydroxide solution to recover bisphenoxy alcohol fluorenes represented by the following general formula (1).
• R 1a and R 1b represent an alkylene group, and these may be the same or different.
• R 2a and R 2b represent an alkyl group, a cycloalkyl group, an aryl group or an alkoxy group, and these are the same.
• N 1 and n 2 represent an integer of 1 or more and may be the same or different, m 1 and m 2 represent 0 or an integer of 1 to 4, and are the same or different May be good.
• a polycarbonate resin having a fluorene structure is hydrolyzed at a temperature of 120 ° C. or lower in the presence of at least one organic solvent selected from aromatic hydrocarbons and aliphatic hydrocarbons, and an aqueous metal hydroxide solution
• high-quality bisphenoxy that can be industrially efficiently depolymerized defective products and waste products produced during the production and / or molding of a polycarbonate resin having a fluorene structure, and can be reused as an optical resin raw material. Alcohol fluorenes can be recovered.
• the industrial effect produced by the present invention is exceptional.
• the polycarbonate resin having a fluorene structure is produced by a known method such as an interfacial polymerization method or a melt polymerization method using bisphenoxy alcohol fluorene represented by the general formula (1) as a constituent raw material. Yes, it may contain additives such as a terminal blocking agent and a stabilizer, and is interpreted in the broadest sense.
• the polycarbonate resin to be subjected to the depolymerization method of the present invention include a polycarbonate resin alone or a resin containing other components within a range not impairing the effects of the present invention, such as polyester carbonates; a resin composition combined with other components For example, a mixture of polycarbonate and polyester may be used.
• the shape is not limited to powder, pellets, sheets, films, molded products, etc., but discarded lenses and sheets; defective products, burrs generated during production and / or molding; production waste, ie polycarbonate Solids recovered from waste of products using resin, pulverized products thereof, and the like are used.
• R 1a and R 1b represent an alkylene group, which may be the same or different.
• R 2a and R 2b represent an alkyl group, a cycloalkyl group, an aryl group or an alkoxy group, and these may be the same or different.
• n 1 and n 2 represent an integer of 1 or more, and may be the same or different.
• m 1 and m 2 represent 0 or an integer of 1 to 4, and may be the same or different.
• the alkylene group represented by R 1a or R 1b can be linear or branched, and examples thereof include an ethylene group, a propylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, and a hexamethylene group.
• the alkylene group represented by R 1a or R 1b is preferably a linear or branched alkylene group having 2 to 6 carbon atoms, more preferably a linear or branched alkylene group having 2 to 4 carbon atoms. In particular, it is a linear or branched alkylene group having 2 or 3 carbon atoms.
• R 1a and R 1b may be composed of the same alkylene group, or may be composed of different alkylene groups.
• Examples of the alkyl group in R 2a or R 2b include carbon such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, t-butyl group, pentyl group, and hexyl group. Examples thereof include linear or branched alkyl groups of 1 to 20.
• the alkyl group is preferably a linear or branched alkyl group having 1 to 8 carbon atoms, more preferably a linear or branched alkyl group having 1 to 6 carbon atoms, and further preferably 1 to 8 carbon atoms. 3 linear or branched alkyl groups.
• Examples of the cycloalkyl group include a carbon number such as a cyclopentyl group, a cyclohexyl group, an alkyl (for example, alkyl having 1 to 4 carbons) -substituted cyclopentyl group, an alkyl (for example, alkyl having 1 to 4 carbons) -substituted cyclohexyl group, and the like.
• a cycloalkyl group having 4 to 16 (preferably 5 to 8 carbon atoms) or an alkyl-substituted cycloalkyl group can be exemplified.
• the cycloalkyl group is more preferably a cyclopentyl group or a cyclohexyl group.
• aryl group examples include a phenyl group, an alkyl (eg, alkyl having 1 to 4 carbon atoms) -substituted phenyl group, and a naphthyl group.
• the aryl group is preferably a phenyl group or an alkyl-substituted phenyl group (for example, a methylphenyl group, a dimethylphenyl group, an ethylphenyl group, etc.), and more preferably a phenyl group.
• the alkoxy group is preferably a linear or branched alkoxy group having 1 to 6 carbon atoms, more preferably a linear or branched alkoxy group having 1 to 3 carbon atoms, such as a methoxy group or an ethoxy group. And propoxy groups.
• the alkyl group, cycloalkyl group, and aryl group may have a substituent other than the alkyl group (for example, an alkoxy group, an acyl group, a halogen atom, etc.).
• N 1 and n 2 representing the number of repetitions of OR 1a and OR 1b , respectively, are preferably 1 to 3, more preferably 1 or 2, and typically 1. N 1 and n 2 are typically the same.
• M 1 and m 2 representing the number of substitutions for R 2a and R 2b are each preferably 0 to 2, more preferably 0 or 1, and typically 0. Also, m 1 and m 2 are typically the same.
• bisphenoxy alcohol fluorenes represented by the general formula (1) are not particularly limited, but 9,9-bis [4- (2-hydroxyethoxy) phenyl] fluorene, 9-bis [4- (2-hydroxyethoxy) -3-methylphenyl] fluorene, 9,9-bis [4- (2-hydroxyethoxy) -3-ethylphenyl] fluorene, 9,9-bis [4- (2-hydroxyethoxy) -3-t-butylphenyl] fluorene, 9,9-bis [3- (2-hydroxyethoxy) -6-methylphenyl] fluorene, 9,9-bis [2- (2-hydroxy Ethoxy) -4-methylphenyl] fluorene, 9,9-bis [2- (2-hydroxyethoxy) -4-ethylphenyl] fluorene, 9,9-bis [4 (2-hydroxypropoxy) -3-methylphenyl] fluorene, 9,9-bis [4- (2-hydroxydieth
• the polycarbonate resin of the present invention contains bisphenoxy alcohol fluorene represented by the general formula (1) as a main component, but may contain other diol components as constituent materials. Other diol components can be used alone or in combination of two or more.
• the other diol component include fluorene diol compounds other than the fluorene diol compound represented by the general formula (1) [for example, 9,9-bis (4-hydroxyphenyl) fluorene, 9,9-bis (4-hydroxy-alkyl-substituted phenyl) fluorene, etc.]; alkylene glycol [eg, ethylene glycol, propylene glycol, 1,3-butanediol, neopentyl glycol, etc.]; alicyclic diol [eg, cyclohexanediol, cyclohexanedimethanol , Tricyclodecane dimethanol, adamantane diol, norbornane dimethanol, 2,2-bis (4-hydroxycyclohexyl) propane, isosorbide, etc.]; aromatic diol [eg, 4,4′-dihydroxydiphenyl, 1,1- (4-hydroxyphenyl) ethane, 1,1-bis
• a polycarbonate resin decomposition reaction (hydrolysis reaction) is performed at a temperature of 120 ° C. or lower in the presence of an aqueous metal hydroxide solution.
• an alkali metal or alkaline earth metal hydroxide is preferably used, and an alkali metal hydroxide is more preferable.
• sodium hydroxide, potassium hydroxide, calcium hydroxide, barium hydroxide and the like are used, preferably sodium hydroxide or potassium hydroxide, and particularly preferably sodium hydroxide.
• These metal hydroxides can be used as any one kind or a mixture of two or more kinds.
• the temperature at which the decomposition reaction (depolymerization) is performed is not particularly limited as long as it is 120 ° C. or less, but is preferably less than 100 ° C., more preferably 30 ° C. to 90 ° C. If the temperature is higher than 120 ° C., the reaction solution tends to be colored brown during the decomposition treatment, and the influence of this tends to deteriorate the hue of the bisphenoxy alcohol fluorenes or decrease the purity. Fluorenes cannot be recovered. In addition, a large amount of heating energy is required, and a pressure vessel is required to cause the reaction at a boiling point or higher, resulting in equipment costs that are economically disadvantageous. Further, when the temperature is low, the decomposition reaction time becomes long, and the processing efficiency may be remarkably deteriorated.
• the amount of metal hydroxide used is preferably 2.0 to 8.0 moles per mole of carbonate bond in the polycarbonate resin.
• 4.1 mol or more of metal hydroxide is used per 1 mol of carbonate bond.
• bisphenoxy alcohol fluorenes are used. Is not recovered as an aqueous metal salt solution, it can be decomposed even at 4.0 mol or less. If the amount of the metal hydroxide used is 2.0 mol or more, it is preferable because the decomposition reaction does not become too slow and the decomposition is sufficiently performed. Moreover, if it is 8.0 mol or less, cost can be suppressed and the amount of water required for washing and purification does not increase, which is economically advantageous.
• the metal hydroxide is used in the form of an aqueous solution.
• the concentration of the alkali metal hydroxide is preferably 10% to 55% by weight, more preferably 20% to 50% by weight. If it is 10% by weight or more, the decomposition rate is not slow, and if it is 55% by weight or less, alkali metal hydroxide is not likely to precipitate and form a slurry, which is preferable. When the alkali metal hydroxide aqueous solution becomes a slurry, the reaction is rather slow. Further, it is preferable that the concentration of the alkali metal hydroxide is 55% by weight or less because coloring and impurity generation hardly occur and the recovered bisphenoxy alcohol fluorenes are excellent in quality.
• the decomposition reaction can be performed in the presence of at least one organic solvent selected from the group consisting of aromatic hydrocarbons and aliphatic hydrocarbons.
• an organic solvent selected from the group consisting of aromatic hydrocarbons and aliphatic hydrocarbons.
• the decomposition reaction is preferably performed in the presence of at least one organic solvent selected from the group consisting of aromatic hydrocarbons and aliphatic hydrocarbons.
• organic solvents selected from the group consisting of aromatic hydrocarbons and aliphatic hydrocarbons.
• other solvents other than the solvent (for example, phenol and methanol) which react with polycarbonate resin can also be used together.
• aromatic hydrocarbon or aliphatic hydrocarbon used as a solvent for the decomposition reaction examples include toluene, xylene, mesitylene, pentane, hexane, heptane, octane, nonane, decane, cyclohexane, and cyclodecane.
• toluene or xylene is preferred.
• the amount used when using at least one organic solvent selected from the group consisting of aromatic hydrocarbons and aliphatic hydrocarbons is preferably in the range of 40 to 2000 parts by weight, preferably 100 to 1000 parts by weight per 100 parts by weight of the polycarbonate resin. A range of parts is more preferred. If the amount of the organic solvent used is 40 parts by weight or more, the aromatic polycarbonate resin is sufficiently dissolved to reduce the insoluble part and increase the yield, and if it is 2000 parts by weight or less, the decomposition rate does not decrease during the decomposition reaction. The time is shortened and the recovery cost of the solvent can be suppressed.
• a polycarbonate resin having a fluorene structure can be depolymerized in a relatively short time under a mild condition at a low temperature using an apparatus that is easy to handle.
• the depolymerization method is a method that can be industrially efficiently carried out.
• Bisphenoxy alcohol fluorenes obtained by depolymerization can be recovered in an organic solvent phase after being dissolved in an organic solvent that can be separated from water and separated from the alkaline aqueous phase used in the reaction. .
• the organic solvent which can be separated from water may be added after the depolymerization reaction, or when the reaction is carried out in the presence of the organic solvent, the reaction solvent can be used as it is as the extraction solvent.
• the organic solvent phase containing the separated bisphenoxy alcohol fluorenes is subjected to purification operations such as washing and adsorption as necessary, and then crystals are precipitated by operations such as crystallization to obtain crystals of bisphenoxy alcohol fluorenes. Can do.
• the precipitated crystals can be recovered by filtration, and can be subjected to purification operations such as washing and recrystallization as necessary.
• the precipitated crystals of bisphenoxy alcohol fluorenes can be recovered as they are by filtration, and purification operations such as washing, adsorption, and recrystallization can be performed as necessary.
• recovered crystals of bisphenoxy alcohol fluorenes are excellent in hue and purity and are suitably used as a polycarbonate resin raw material for optical resins.
• HPLC purity The area percentage value when HPLC measurement was performed under the following measurement conditions was defined as the HPLC purity of each component.
• ⁇ Device "LC-2010AHT” manufactured by Shimadzu Corporation ⁇ Column: “L-column ODS” manufactured by the Chemical Substance Evaluation Research Organization (5 ⁇ m, 4.6mm ⁇ ⁇ 250mm) -Column temperature: 40 ° C ⁇
• Liquid B acetonitrile-Mobile phase flow rate: 1.0 ml / min-Mobile phase gradient: Liquid B concentration: 30% (0 minutes)-> 100% (after 25 minutes)-> 100% ( 35 minutes later)
• EXSTAR DSC 7020 manufactured by SII Nano Technology Co., Ltd.
• the area percentage value when the GPC measurement of the reaction solution was performed under the above measurement conditions was defined as the production rate of each component and dimer.
• Example 1 A reactor equipped with a stirrer, a cooler, and a thermometer was charged with 100 parts by weight of the polycarbonate resin solid obtained in Synthesis Example 1, 97 parts by weight of a 48% aqueous sodium hydroxide solution, and 600 parts by weight of toluene. The mixture was heated and stirred for 2 hours. When the reaction solution was analyzed by GPC, the high molecular weight product disappeared, 99.4% was 9,9-bis [4- (2-hydroxyethoxy) phenyl] fluorene, and 0.6% was its dimer. It was disassembled. Subsequently, the reaction liquid was allowed to stand, and then the aqueous phase was separated.
• the toluene solvent phase was washed with water four times to remove inorganic components.
• the toluene solvent phase was then filtered and cooled to room temperature.
• the precipitated crystals were filtered and dried to obtain 78 parts by weight of 9,9-bis [4- (2-hydroxyethoxy) phenyl] fluorene white crystals.
• the white crystals had an HPLC purity of 99.0% and a melting point of 161 ° C.
• Example 2 In Example 1, the same operation was performed except that 97 parts by weight of 48% aqueous sodium hydroxide solution was changed to 215 parts by weight of 24% aqueous sodium hydroxide solution, and reacted for 9 hours. When the reaction solution was analyzed by GPC, the high molecular weight product disappeared, 99.2% was 9,9-bis [4- (2-hydroxyethoxy) phenyl] fluorene, and 0.8% was its dimer. It was disassembled.
• Example 3 In Example 1, the same operation was performed except that the reaction temperature was changed from 80 ° C. to 40 ° C., and the reaction was carried out for 14 hours. When the reaction solution was analyzed by GPC, the high molecular weight product disappeared, 99.4% was 9,9-bis [4- (2-hydroxyethoxy) phenyl] fluorene, and 0.6% was its dimer. It was disassembled.
• Example 4 In Example 1, the same operation was carried out for 5 hours except that 97 parts by weight of 48% aqueous sodium hydroxide solution was changed to 150 parts by weight of 24% aqueous sodium hydroxide solution, toluene was octane, and the reaction temperature was 90 ° C. I let you. When the reaction solution was analyzed by GPC, the high molecular weight product disappeared, 99.2% was 9,9-bis [4- (2-hydroxyethoxy) phenyl] fluorene, and 0.8% was its dimer. It was disassembled.
• Example 5 A reactor equipped with a stirrer, a cooler, and a thermometer was charged with 100 parts by weight of the polycarbonate resin solid material obtained in Synthesis Example 2, 60 parts by weight of a 48% aqueous sodium hydroxide solution, and 300 parts by weight of xylene. The mixture was heated and stirred for 2 hours. When the reaction solution was analyzed by GPC, the high molecular weight substance disappeared, 99.7% was 9,9-bis [2- (2-hydroxyethoxy) -4-methylphenyl] fluorene, and 0.3% was It had decomposed into its dimer. Subsequently, the reaction liquid was allowed to stand, and then the aqueous phase was separated.
• the xylene solvent phase was washed with water four times to remove inorganic components.
• the xylene solvent phase was then filtered and cooled to room temperature.
• the precipitated crystals were filtered and dried to obtain 82 parts by weight of 9,9-bis [2- (2-hydroxyethoxy) -4-methylphenyl] fluorene white crystals.
• the white crystals had an HPLC purity of 99.1% and a melting point of 172 ° C.
• Example 6 Manufacture of molded products using polycarbonate resin as raw materials, 9,9-bis [4- (2-hydroxyethoxy) phenyl] fluorene and 2,2-bis (4-hydroxyphenyl) propane (bisphenol A) 170 parts of a resin obtained by pulverizing waste materials generated at times, 82 parts by weight of a 48% aqueous sodium hydroxide solution, and 391 parts by weight of toluene were charged and stirred at 80 ° C. for 2 hours. When the reaction solution was analyzed by GPC, the high molecular weight substances disappeared, 99.5% were 9,9-bis [4- (2-hydroxyethoxy) phenyl] fluorene and bisphenol A, and 0.5% were these.
• the dimer was decomposed. Subsequently, the reaction liquid was allowed to stand, and then the aqueous phase was separated. Further, the organic layer was washed with water four times to remove inorganic components and bisphenol A. The toluene solvent was then dehydrated under reflux. Subsequently, this toluene solvent phase was filtered to remove insoluble matters, and then cooled to room temperature. The precipitated crystals were filtered and dried to obtain 124 parts by weight of 9,9-bis [4- (2-hydroxyethoxy) phenyl] fluorene white crystals. The white crystals had an HPLC purity of 98.9% and a melting point of 161 ° C.
• Example 7 170 parts of recovered product obtained by pulverizing the discarded film using a polycarbonate resin made of 9,9-bis [4- (2-hydroxyethoxy) phenyl] fluorene and isosorbide as raw materials, 48% sodium hydroxide 82 parts by weight of an aqueous solution and 391 parts by weight of toluene were added, and the mixture was heated and stirred at 80 ° C. for 2 hours.
• the reaction solution was analyzed by GPC, the high molecular weight product disappeared, 99.5% was 9,9-bis [4- (2-hydroxyethoxy) phenyl] fluorene and isosorbide, and 0.5% was these. It had decomposed into a dimer.
• the reaction liquid was allowed to stand, and then the aqueous phase was separated. Further, the organic layer was washed with water four times to remove inorganic components and isosorbide. The toluene solvent was then dehydrated under reflux. Subsequently, this toluene solvent phase was filtered to remove insoluble matters, and then cooled to room temperature. The precipitated crystals were filtered and dried to obtain 107 parts by weight of 9,9-bis [4- (2-hydroxyethoxy) phenyl] fluorene white crystals. The white crystals had an HPLC purity of 97.4% and a melting point of 160 ° C.
• Example 8 20.0 parts by weight of a recovered product obtained by pulverizing a commercially available special polyester carbonate resin containing 9-bis [4- (2-hydroxyethoxy) phenyl] fluorene and terephthalic acid as the main skeleton in a pellet form, 48% aqueous sodium hydroxide solution 14.1 parts by weight and 46.0 parts by weight of toluene were charged, and the mixture was heated and stirred at 88 ° C. for 5 hours. When the reaction solution was analyzed by GPC, the high molecular weight substances disappeared, 99.9% were 9,9-bis [4- (2-hydroxyethoxy) phenyl] fluorene and terephthalic acid, and 0.1% were these.
• the dimer was decomposed.
• the obtained toluene solvent was further washed four times with water to remove inorganic components and terephthalic acid, and then dehydrated under reflux of the toluene solvent.
• the toluene solvent phase was then filtered to remove insolubles, and then cooled to room temperature.
• the precipitated crystals were filtered and dried to obtain 16.30 parts by weight of 9,9-bis [4- (2-hydroxyethoxy) phenyl] fluorene white crystals.
• the white crystals had an HPLC purity of 98.7% and a melting point of 160 ° C.
• bisphenoxy alcohol fluorenes having a specific structure can be efficiently recovered from a polycarbonate resin having a fluorene structure.
• the depolymerization method of the present invention it is possible to industrially efficiently depolymerize defective products and waste products produced during the production and molding of polycarbonate resins having a fluorene structure, and high-quality bisphenoxy alcohol fluorenes. Can be efficiently recovered. Furthermore, the recovered bisphenoxy alcohol fluorenes can be reused as an optical resin raw material.

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