Thermoplastic resin composition, and method for preparing and use thereof

Abstract

Disclosed is a thermoplastic resin composition, a method for producing the same, and a use thereof. The thermoplastic resin composition contains a structural unit derived from a compound represented by general formula (A), wherein Z1 ring represents a cycloalkyl group having 6 to 8 carbon atoms, a bicycloalkyl group having 6 to 10 carbon atoms, or a bridged cycloalkyl group having 10 to 12 carbon atoms, wherein the number of carbon atoms includes 2 carbon atoms common to a norbornane ring; X represents an alkylene group having 1 to 4 carbon atoms; and R1 and R2 each independently represent a hydrogen atom, a halogen atom, or an alkyl group having 1 to 4 carbon atoms. The thermoplastic resin composition further contains an optional structural unit derived from a compound represented by general formula (B). The thermoplastic resin composition has advantages such as a high Abbe number, a high refractive index, a high glass transition temperature, and a high light transmittance.

Description

TECHNICAL FIELD

[0001] The present application relates to the field of optical resin, in particular to a thermoplastic resin composition and its preparation method and use. BACKGROUND

[0002] Optical polyester and polycarbonate resin have become the first choice for manufacturing plastic lenses due to their high refractive index, easy molding, high production efficiency and other advantages. Patent US4810771A proposes a high-refractive polyester resin material for optical lenses, which is prepared by using 9,9-bis-(4-hydroxyphenyl) fluorene as a monomer, and the refractive index can reach about 1.64. Konica patent JP2001072872A discloses a thermoplastic resin material for optical lenses and its manufacturing method, which mainly uses 2,2-bis-(2-hydroxyethoxy)-1,1-naphthalene as a polymerization monomer, and can be used to prepare polyester, polycarbonate, polyurethane, sulfone polymer and other optical resin materials, and the refractive index is higher, which can reach about 1.66.

[0003] However, in the case of optical polycarbonate resin used as optical lens, in addition to the requirement of high refractive index, the resin also requires high Abbe number. Because, generally, if the refractive index of the material is high, there will be a large dispersion when the lens is imaging, which will cause the image to be blurred, and a lens with high Abbe number is needed to correct the chromatic aberration. Patent CN106661216A discloses a polycarbonate resin, according to the description in paragraphs

[0103] and

[0104] , the synthesized polycarbonate resin has a refractive index of 1.50-1.65 after molding, and the upper limit of Abbe number is about 60. However, with the emergence of higher refractive index materials, optical lenses need higher Abbe number resin materials for dispersion correction when designing. In addition, according to the description in paragraphs

[0168] -

[0173] , the glass transition temperature of the polycarbonate resin synthesized with D-NDM monomer is generally low, which is 110-140℃, and it is easy to soften during high-temperature coating of the lens, causing the surface precision to be poor, so it needs to be matched with a rigid monomer to increase its glass transition temperature.

[0004] There is a need for a thermoplastic optical resin material with higher Abbe number and higher glass transition temperature. SUMMARY

[0005] The purpose of the present application is to provide a thermoplastic resin composition and its preparation method and use, which has the advantages of high Abbe number, high glass transition temperature, high refractive index, high light transmittance, etc., and can meet the use requirements of optical shaped bodies and optical lenses.

[0006] To solve the above problems, the present application provides a thermoplastic resin composition, which comprises a structural unit derived from a compound represented by general formula (A),

[0007]

[0008] In general formula (A), Z1 ring represents a cycloalkyl group with 6 to 8 carbon atoms, a bicycloalkyl group with 6 to 10 carbon atoms, or a bridged cycloalkyl group with 10 to 12 carbon atoms, wherein the number of carbon atoms includes the two carbon atoms shared with the norbornene ring, preferably cyclohexyl or dinorbornene; X represents an alkylene group with 1 to 4 carbon atoms; R1 and R2 independently represent a hydrogen atom, a halogen atom, and an alkyl group with 1 to 4 carbon atoms, respectively.

[0009] Preferably, the compound represented by general formula (A) of the present invention comprises one or more of the following substances:

[0010]

[0011] The thermoplastic resin composition provided by the present invention further comprises, optionally, structural units derived from compounds represented by general formula (B).

[0012]

[0013] In general formula (B), Z2 independently represents an aryl group of C6-C14, preferably phenyl, naphthyl, anthracene, or phenanthrene; Y represents an alkylene group with 1 to 4 carbon atoms; R3 to R6 independently represent a hydrogen atom, a halogen atom, an alkyl group with 1 to 6 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a cycloalkyl group with 5 to 10 carbon atoms, a cycloalkoxy group with 5 to 10 carbon atoms, an aryl group with 6 to 14 carbon atoms, or an aryloxy group with 6 to 14 carbon atoms, preferably a hydrogen atom, phenyl, or naphthyl; and m and n are each independently integers from 1 to 4.

[0014] In the thermoplastic resin composition of the present invention, at least 80% of the structural units are derived from the structural units of compounds represented by general formulas (A) and (B); preferably, at least 90% of the structural units of the thermoplastic resin composition are derived from the structural units of compounds represented by general formulas (A) and (B), and may also contain structural units derived from other diol compounds. Examples of diol compounds include, but are not limited to, ethylene glycol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, neopentanediol, 1,4-cyclohexanediol, 2,2-bis(2-hydroxyethoxy)-1,1-naphthyl, 2,2-bis(2-hydroxyethoxy)-5,5-diphenyl-1,1-naphthyl, 2,2-bis(2-hydroxyethoxy)-6,6-diphenyl-1,1-naphthyl, and 2,2-bis(2-hydroxyethoxy)-6,6-di(naphth-2-yl)-1,1-naphthyl.

[0015] More preferably, all structural units of the thermoplastic resin composition of the present invention are derived from the structural units of the compounds represented by general formula (A) and general formula (B), wherein the proportion of structural units derived from the compounds represented by general formula (A) is 1 to 99 mol%, and the proportion of structural units derived from the compounds represented by general formula (B) is 1 to 99 mol%.

[0016] Preferably, the thermoplastic resin composition comprises 30-80 mol% of structural units derived from the compound represented by general formula (A) and 20-70 mol% of structural units derived from the compound represented by general formula (B).

[0017] The thermoplastic resin composition of the present invention can be one or more of polyester, polycarbonate, and polyester carbonate.

[0018] The form in which the structural units derived from the compounds represented by general formulas (A) and (B) are contained in the resin is not particularly limited. For example, in this invention, the thermoplastic resin composition may contain a copolymer comprising structural units derived from the compounds represented by general formulas (A) and (B), or it may be a binary resin composition comprising homopolymers of the individual structural units; or it may be a blend obtained by blending a homopolymer comprising structural units derived from the compounds represented by general formula (A) with a homopolymer comprising structural units derived from the compounds represented by general formula (B).

[0019] The thermoplastic resin composition of the present invention may contain any structure including random, block, and alternating copolymer structures.

[0020] The thermoplastic resin composition of this invention has a refractive index nD of 1.55–1.67 at 20°C and a wavelength of 589 nm, an Abbe number of 25–80, a glass transition temperature of 120–190°C, and an orientation birefringence Δn of 1.0 × 10⁻⁶. -3 Below that, the average transmittance at wavelengths of 780nm to 1000nm is over 87%.

[0021] The thermoplastic resin composition of the present invention may contain additives such as mold release agents, ultraviolet absorbers, flow improvers, crystal nucleating agents, reinforcing agents, dyes, antistatic agents, or antibacterial agents.

[0022] The thermoplastic resin composition of the present invention can be prepared by reacting a dihydroxy compound containing the structural formula (A) or (B) with a carbonate diester or a dicarboxylic acid and / or a dicarboxylic acid ester.

[0023] Preferably, the dihydroxy compound is produced by reacting it with a carbonate diester or a dicarboxylic acid and / or a dicarboxylic acid ester in an alkaline compound catalyst and / or an ester exchange catalyst, or under catalyst-free conditions, via melt ester exchange polycondensation.

[0024] Preferably, the dihydroxy compound represented by general formula (B) has at least one of the following structures:

[0025]

[0026] In this invention, the carbonate diester is one or more of diphenyl carbonate, dimethyl carbonate, diethylphenyl carbonate, diisopropylphenyl carbonate, dimethyl carbonate, diethyl carbonate, dibutyl carbonate, dicyclohexyl carbonate, etc., preferably diphenyl carbonate.

[0027] In this invention, the dicarboxylic acid is selected from one or more of terephthalic acid, terephthalic acid, 1,4-naphthalenedicarboxylic acid, 2,6-naphthalenedicarboxylic acid, 2,2-biphenyl dicarboxylic acid, 1,4-cyclohexanedicarboxylic acid, and 2,2'-bis(carboxymethoxy)-1,1'-binaphthyl, preferably terephthalic acid and / or 2,6-naphthalenedicarboxylic acid.

[0028] In this invention, the dicarboxylic acid ester is selected from any one or more of dimethyl terephthalate, diethyl terephthalate, dimethyl terephthalate, dimethyl 1,4-naphthalenedicarboxylate, dimethyl 2,6-naphthalenedicarboxylate, dimethyl 2,2-biphenyl dicarboxylate, dimethyl 1,4-cyclohexanedicarboxylate, and 2,2'-bis(carboxymethyl methoxy)-1,1'-binaphthyl, preferably dimethyl terephthalate and / or dimethyl 2,6-naphthalenedicarboxylate.

[0029] The molar ratio of the carbonate diester or dicarboxylic acid and / or dicarboxylic acid ester to the sum of the added dihydroxy compounds of general formulas (A) and (B) is 0.95 to 1.18:1, preferably 1.01 to 1.08:1.

[0030] The alkaline compound catalyst of this invention is one or more of lithium chloride, sodium chloride, potassium chloride, cesium chloride, lanthanum acetylacetone, cerium acetylacetone, sodium hydroxide, magnesium hydroxide, calcium hydroxide, strontium hydroxide, barium hydroxide, lithium bicarbonate, sodium bicarbonate, potassium bicarbonate, magnesium bicarbonate, calcium bicarbonate, strontium bicarbonate, barium bicarbonate, sodium carbonate, magnesium carbonate, calcium carbonate, strontium carbonate, barium carbonate, magnesium acetate, calcium acetate, strontium acetate, barium acetate, magnesium stearate, calcium stearate, calcium benzoate, magnesium phenyl phosphate, tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, trimethylbenzylammonium hydroxide, triethylamine, dimethylbenzylamine, triphenylamine, diethylamine, tetramethylborohydride, tetrabutylammonium borohydride, tetrabutyltetraphenylborate, tetraphenyltetraphenylborate, etc., preferably one or more of sodium hydroxide, sodium bicarbonate, and cesium carbonate.

[0031] The transesterification catalyst of the present invention can be one or more of zinc acetate, zinc benzoate, zinc 2-ethylhexanoate, tin chloride, tin acetate, cerium acetylacetone, zirconium acetylacetone, zirconium acetate, tetrabutoxyzirconium, etc., preferably one or more of lanthanum acetylacetone, zirconium acetate, and zinc acetate.

[0032] The molar ratio of the total amount of the basic compound catalyst and / or transesterification catalyst to the total amount of the dihydroxy compound described in this invention is 1 × 10⁻⁶. -8 ~1×10 -3 The preferred ratio is 1×10 -7 ~2×10 -5 .

[0033] In some preferred embodiments of the present invention, the method for preparing the thermoplastic resin composition includes adding a dihydroxy compound of general formula (A) and general formula (B), a diester, a catalyst, and optional additives to a reactor; fully purging the air in the reactor with nitrogen 3 to 5 times; then heating the material in the reactor to melt it at a melting temperature of 180 to 210°C, preferably 190 to 200°C, with a residence time of 40 to 100 minutes, preferably 50 to 80 minutes. After the material has melted, stirring is started, pressure control is activated (either reduced or increased pressure), and the temperature is raised to the transesterification reaction temperature of 210 to 250°C, preferably 220 to 240°C, with a residence time of 60 to 320 minutes, preferably 150 to 240 minutes. Then, the pressure is further reduced and the temperature is increased to initiate the polycondensation reaction. During this stage, the system pressure is 10–500 Pa(A), preferably 50–100 Pa(A), the reaction temperature is 230–270 °C, preferably 230–255 °C, and the residence time is 10–120 min, preferably 20–60 min. During the reaction, the generated small molecule compounds are immediately removed by distillation, ultimately yielding a high molecular weight thermoplastic resin composition in the reactor.

[0034] The present invention also provides an blend, which can be obtained by blending different thermoplastic resin compositions obtained by polymerization in equipment such as an extruder, a kneader, and a mixer.

[0035] The thermoplastic resin composition of the present invention is used in optical molded bodies, optical lenses, and optical films.

[0036] The thermoplastic resin composition of this invention has a high refractive index, good flowability, is easy to process, resistant to low temperatures, resistant to hydrolysis, and highly transparent, making it suitable for use in the field of optical lenses. Optical lenses using the thermoplastic resin composition of this invention can be thinner and lighter, reducing lens weight and the number of lenses required, thereby lowering costs and showing broad application prospects. Detailed Implementation

[0037] The present invention will now be described in conjunction with specific embodiments. It should be noted that the embodiments are only used to further illustrate the present invention and should not be construed as limiting the scope of protection of the present invention. Any non-substantial improvements and adjustments made to the present invention based on its content are within the scope of protection of the present invention.

[0038] 1) Weight-average molecular weight (Mw): Using gel permeation chromatography (GPC), a standard curve was prepared using tetrahydrofuran as the developing solvent and standard polystyrene with a known molecular weight (molecular weight distribution = 1). Based on this standard curve, Mw was calculated from the retention time of GPC.

[0039] 2) Refractive index (nD): For a 1 mm thick film composed of the thermoplastic resin composition prepared in the examples, the refractive index (nD) of the thermoplastic resin composition of the present invention at 23 °C and 589 nm was determined using an Abbe refractometer according to the method of JIS-K-7142.

[0040] 3) Abbe number: For the 0.1 mm thick polycarbonate resin film prepared in the examples, the refractive index at wavelengths of 486 nm, 589 nm, and 656 nm at 23 °C was measured using an Abbe refractometer, and the Abbe number ν was calculated using the following formula.

[0041] ν=(nD-1) / (nF-nC).

[0042] 4) Orientation birefringence (Δn): After cutting a 0.1 mm thick cast film into 5.0 cm squares, insert both ends of the film into chucks (3.0 cm apart) and stretch it to 1.5 times its original strength at Tg+5℃ of polycarbonate resin. Use an ellipsometer to measure the phase difference (Re) at 589 nm, and calculate the orientation birefringence (Δn) using the following formula.

[0043] Δn=Re / d

[0044] Δn: Orientation birefringence; Re: Phase difference; d: Thickness.

[0045] 5) Transmittance: The transmittance of a 0.1 mm thick film made of polycarbonate resin prepared in the examples was measured using a turbidimeter according to the method of JIS-K-7361-1.

[0046] The sources of some of the reagent raw materials used in the embodiments and comparative examples of this invention are as follows; unless otherwise specified, the remaining reagent raw materials are all commercially available products:

[0047] The compound represented by general formula (A) can be given a polycyclic diene by the Diels-Aldell reaction, and then a polycyclic diol by hydroformylation. The Diels-Aldell reaction and hydroformylation are well known techniques.

[0048] Preparation Example 1

[0049] The specific synthetic route for A-1 is as follows:

[0050]

[0051] (1) 79.26 g (1.2 mol) of cyclopentadiene and 96.07 g (1.2 mol) of cyclohexadiene were added to a 500 ml stainless steel reactor and reacted at 200 °C for 2 hours. The reaction solution containing the compound shown in Formula 1a was obtained and purified by distillation.

[0052] (2) The hydroformylation reaction of the compound shown in Formula 1a was carried out using a 500 ml stainless steel reactor and a CO / H2 mixed gas (CO / H2 molar ratio = 1). 70 g of the compound shown in Formula 1a, 140 g of toluene, 1.2 g of triphenyl phosphite, and 550 μl of a toluene solution of Rh(acac)(CO)2 (concentration 0.006 mol / L) were added to the reactor. The reaction was purged three times with nitrogen and three times with the CO / H2 mixed gas. The system was then pressurized with the CO / H2 mixed gas and reacted at 110 °C and 2 MPa for 6 hours. After the reaction, the target product, compound A-1, was obtained. The NMR results are as follows: 1H-NMR (400 MHz, CDCl3) / δ×10 -6 :3.65-3.37(m,6H),2.13-1.88(m,2H),1.52-1.24(m,14H).

[0053] Preparation Example 2

[0054] The specific synthetic route for A-2 is as follows:

[0055]

[0056] (1) 189.94 g (1.3 mol) of the compound shown in formula 1a and 70.27 g (1.3 mol) of butadiene were added to a 500 ml stainless steel reactor and reacted at 210 °C for 1.5 hours. A reaction solution containing the compound shown in formula 2a was obtained and purified by distillation.

[0057] (2) The hydroformylation reaction of the compound shown in Formula 2a was carried out using a 500 ml stainless steel reactor and a CO / H2 mixed gas (CO / H2 molar ratio = 1). 70 g of the compound shown in Formula 2a, 140 g of toluene, 1.1 g of triphenyl phosphite, and 550 μl of a toluene solution of Rh(acac)(CO)2 (concentration 0.007 mol / L) were added to the reactor. The system was purged three times with nitrogen and three times with the CO / H2 mixed gas. The system was then pressurized with the CO / H2 mixed gas and reacted at 100 °C and 2.5 MPa for 5 hours. After the reaction, the target product, compound A-2, was obtained. The NMR results are as follows: 1H-NMR (400 MHz, CDCl3) / δ×10 -6 :3.65-3.37(m,6H),2.13-1.88(m,2H),1.52-1.24(m,20H).

[0058] Preparation Example 3

[0059] The specific synthetic route for A-3 is as follows:

[0060]

[0061] (1) 160.72 g (1.1 mol) of the compound shown in formula 3a and 72.66 g (1.1 mol) of cyclopentadiene were added to a 500 ml stainless steel reactor and reacted at 205 °C for 2 hours. The reaction solution containing the compound shown in formula 3a was obtained and purified by distillation.

[0062] (2) The hydroformylation reaction of the compound shown in Formula 3a was carried out using a 500 ml stainless steel reactor and a CO / H2 mixed gas (CO / H2 molar ratio = 1). 70 g of the compound shown in Formula 3a, 140 g of toluene, 1.25 g of triphenyl phosphite, and 550 μl of a toluene solution of Rh(acac)(CO)2 (concentration 0.0055 mol / L) were added to the reactor. The reaction was purged three times with nitrogen and three times with the CO / H2 mixed gas. The system was then pressurized with the CO / H2 mixed gas and reacted at 95 °C and 3 MPa for 7 hours. After the reaction, the target product, compound A-3, was obtained. The NMR results are as follows: 1H-NMR (400 MHz, CDCl3) / δ×10 -6 :3.65-3.37(m,6H),2.13-1.88(m,4H),1.51-1.24(m,18H).

[0063] Preparation Example 4

[0064] The specific synthetic route for A-4 is as follows:

[0065]

[0066] (1) 151.90 g (1.15 mol) of dicyclopentadiene and 66.75 g (1.15 mol) of allyl alcohol were added to a 500 ml stainless steel reactor and reacted at 200 °C for 2 hours. The reaction solution containing the compound shown in Formula 4a was obtained and purified by distillation.

[0067] (2) 114.08 g (0.6 mol) of the compound shown in formula 4a and 39.63 g (0.6 mol) of cyclopentadiene were added to a 500 ml stainless steel reactor and reacted at 190 °C for 2.5 hours. The reaction solution containing the compound shown in formula 4b was obtained and purified by distillation.

[0068] (3) The hydroformylation reaction of the compound shown in Formula 4b was carried out using a 500 ml stainless steel reactor and a CO / H2 mixed gas (CO / H2 molar ratio = 1). 70 g of the compound shown in Formula 4b, 140 g of toluene, 0.5 g of triphenyl phosphite, and 550 μl of a toluene solution of Rh(acac)(CO)2 (concentration 0.003 mol / L) were added to the reactor. The system was purged three times with nitrogen and three times with the CO / H2 mixed gas. Then, the system was pressurized with the CO / H2 mixed gas and reacted at 100 °C and 1.8 MPa for 5 hours. After the reaction, the target product, compound A-4, was obtained. The NMR results are as follows: 1H-NMR (400 MHz, CDCl3) / δ×10 -6 :3.65-3.37(m,6H),2.13-1.88(m,6H),1.51-1.24(m,16H).

[0069] Example 1

[0070] 21.03 g (0.1 mol) of A-1, 22.28 g (0.104 mol) of diphenyl carbonate, and 65.16 μg (2.0 × 10⁻⁶) of [unclear text - possibly a typo, should be 21.03 g (0.1 mol) of A-1, 22.28 g (0.104 mol) of diphenyl carbonate, and 65.16 μg -7Cesium carbonate (mol) was placed in a 200 ml four-necked flask equipped with a stirrer and distillation apparatus. The mixture was purged with nitrogen four times and heated to 190 °C under a nitrogen atmosphere of 101 kPa(A). After heating for 60 min to confirm complete dissolution of the raw materials, stirring was started, and the pressure was adjusted to 25 kPa(A). Simultaneously, the temperature was increased to 240 °C at a rate of 30 °C / hr. At this point, phenol, a byproduct, began to distill off. The reaction was maintained at 240 °C for 180 min, then increased to 250 °C at a rate of 60 °C / hr. Once the temperature reached 250 °C, the pressure was gradually reduced to 50 Pa(A) over one hour, and the reaction was continued under stirring for 60 min. The reaction was then terminated. After the reaction, nitrogen was introduced into the four-necked flask to restore atmospheric pressure. The resulting thermoplastic resin composition was removed, pelletized, molded, and its performance was evaluated. The results are listed in Table 1.

[0071] Example 2

[0072] 8.29 g (0.03 mol) of A-3, 42.11 g (0.07 mol) of B1, 23.14 g (0.108 mol) of diphenyl carbonate, and 120 μg (3.0 × 10⁻⁶) of [unclear text - likely a typo, should be 0.03 mol] were added. -6 Sodium hydroxide (mol) was placed in a 200 ml four-necked flask equipped with a stirrer and distillation apparatus, and the same procedures as in Example 1 were performed. The results are listed in Table 1.

[0073] Example 3

[0074] 10.58 g (0.04 mol) of A-2, 11.54 g (0.04 mol) of A-4, 8.99 g (0.02 mol) of B-2, 21.64 g (0.101 mol) of diphenyl carbonate, and 55.05 μg (3.0 × 10⁻⁶) of [unclear - likely a chemical compound or similar substance]. -7 1 mol) of zinc acetate was placed in a 200 ml four-necked flask equipped with a stirrer and a distillation apparatus, and the same procedures as in Example 1 were performed. The results are listed in Table 1.

[0075] Example 4

[0076] 12.62g (0.06mol) A-1, 8.29g (0.03mol) A-3, 6.02g (0.01mol) B-1, 20.99g (0.098mol) diphenyl carbonate, and 2.181mg (5.0×10) -6 Lanthanum acetylacetone (mol) was placed in a 200 ml four-necked flask equipped with a stirrer and distillation apparatus, and the same procedures as in Example 1 were performed. The results are listed in Table 1.

[0077] Example 5

[0078] 28.842 g (0.1 mol) of A-4, 21.42 g (0.1 mol) of diphenyl carbonate, and 91.75 μg (5.0 × 10⁻⁶) of [unclear - likely a specific compound or ingredient] were added. -7 1 mol) of zinc acetate was placed in a 200 ml four-necked flask equipped with a stirrer and a distillation apparatus, and the same procedures as in Example 1 were performed. The results are listed in Table 1.

[0079] Example 6

[0080] 9.46 g (0.045 mol) of A-1, 15.57 g (0.054 mol) of A-4, 0.45 g (0.001 mol) of B-2, 20.35 g (0.095 mol) of diphenyl carbonate, and 3.274 μg (1.0 × 10⁻⁶) of [unclear - likely a chemical compound or similar product] were added. -9 Zirconium acetate (mol) was placed in a 200 ml four-necked flask equipped with a stirrer and distillation apparatus, and the same procedures as in Example 1 were performed. The results are listed in Table 1.

[0081] Example 7

[0082] 0.28 g (0.001 mol) of A-3, 54.14 g (0.09 mol) of B-1, 4.04 g (0.009 mol) of B-2, 25.28 g (0.118 mol) of diphenyl carbonate, and 0.436 μg (1.0 × 10⁻⁶) of [unspecified substance]. -4 Lanthanum acetylacetone (mol) was placed in a 200 ml four-necked flask equipped with a stirrer and distillation apparatus, and the same procedures as in Example 1 were performed. The results are listed in Table 1.

[0083] Example 8

[0084] 4.21g (0.02mol) A-1, 6.61g (0.025mol) A-2, 9.67g (0.035mol) A-3, 2.88g (0.01mol) A-4, 3.01g (0.05mol) B-1, 2.25g (0.005mol) B-2, 23.99g (0.112mol) diphenyl carbonate, and 8.401mg (2.0×10) -6 Sodium bicarbonate (mol) was placed in a 200 ml four-necked flask equipped with a stirrer and distillation apparatus, and the same procedures as in Example 1 were performed. The results are listed in Table 1.

[0085] Example 9

[0086] 10.58 g (0.04 mol) A-2, 11.54 g (0.04 mol) A-4, 8.99 g (0.02 mol) B-2, 20.35 g (0.095 mol) diphenyl carbonate, 1.03 g (0.006 mol) 1,4-cyclohexanedicarboxylic acid, and 55.05 μg (3.0 × 10⁻⁶) were added. -7 1 mol) of zinc acetate was placed in a 200 ml four-necked flask equipped with a stirrer and distillation apparatus, and the same operation as in Example 3 was performed. The results are listed in Table 1.

[0087] Comparative Example 1

[0088] 60.15 g (0.1 mol) B-1, 23.14 g (0.108 mol) diphenyl carbonate, and 120 μg (3.0 × 10⁻⁶) were added. -6 Sodium hydroxide (mol) was placed in a 200 ml four-necked flask equipped with a stirrer and distillation apparatus, and the same procedures as in Example 2 were performed. The results are listed in Table 1.

[0089] Table 1. Performance of Examples and Comparative Samples

[0090]

Claims

1. A thermoplastic resin composition comprising structural units derived from a compound of general formula (A) and optionally structural units derived from a compound of general formula (B), wherein the compound of general formula (A) comprises one or more of the following substances: Formula A-1 Formula A-2 Formula A-3 Formula A-4; The compound represented by general formula (B) is （B）， In general formula (B), Z2 independently represents an aryl group of C6-C14; Y represents an alkylene group with 1 to 4 carbon atoms; R3, R4, R5, and R6 independently represent a hydrogen atom, a halogen atom, an alkyl group with 1 to 6 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a cycloalkyl group with 5 to 10 carbon atoms, a cycloalkoxy group with 5 to 10 carbon atoms, an aryl group with 6 to 14 carbon atoms, or an aryloxy group with 6 to 14 carbon atoms; the values ​​of m and n are each independent integers from 1 to 4; The method for preparing the thermoplastic resin composition includes the following steps: The compounds represented by general formula (A) and optionally general formula (B) are subjected to transesterification polycondensation or esterification polycondensation with one or more of carbonate diesters, dicarboxylic acids, and dicarboxylic acid esters.

2. The thermoplastic resin composition according to claim 1, characterized in that, In general formula (B), Z2 independently represents phenyl, naphthyl, anthraceneyl, and phenanthryl; R3, R4, R5, and R6 independently represent hydrogen, phenyl, and naphthyl, respectively.

3. The thermoplastic resin composition according to claim 1, characterized in that, At least 80% of the structural units of the thermoplastic resin composition are structural units derived from compounds represented by general formulas (A) and (B).

4. The thermoplastic resin composition according to claim 1, characterized in that, At least 90% of the structural units of the thermoplastic resin composition are structural units derived from compounds represented by general formulas (A) and (B).

5. The thermoplastic resin composition according to claim 1, characterized in that, All structural units of the thermoplastic resin composition are derived from the structural units of the compounds shown in general formula (A) and general formula (B), wherein the proportion of structural units derived from the compounds shown in general formula (A) is 1 to 99 mol%, and the proportion of structural units derived from the compounds shown in general formula (B) is 1 to 99 mol%.

6. The thermoplastic resin composition according to claim 5, characterized in that, The proportion of structural units derived from the compound represented by general formula (A) is 30–80 mol%, and the proportion of structural units derived from the compound represented by general formula (B) is 20–70 mol%.

7. The thermoplastic resin composition according to claim 1, characterized in that, The thermoplastic resin composition described above has a refractive index nD of 1.55~1.67, an Abbe number of 25~80, a glass transition temperature of 120~190℃, and an orientation birefringence Δn of 1.0×10⁻⁶ at 20℃ and a wavelength of 589nm. -3 Below that, the average transmittance at wavelengths of 780nm to 1000nm is over 87%.

8. The thermoplastic resin composition according to claim 1, characterized in that, The thermoplastic resin composition is one or more of polyester, polycarbonate, and polyester carbonate.

9. The thermoplastic resin composition according to claim 1, characterized in that, The molar ratio of the carbonate diester or dicarboxylic acid and / or dicarboxylic acid ester to the sum of the added compounds of general formula (A) and optionally general formula (B) is 0.95 to 1.18:

1.

10. The thermoplastic resin composition according to claim 1, characterized in that, The molar ratio of the carbonate diester or dicarboxylic acid and / or dicarboxylic acid ester to the sum of the added compounds of general formula (A) and optionally general formula (B) is 1.01 to 1.08:

1.

11. Use of the thermoplastic resin composition according to any one of claims 1 to 10, wherein the thermoplastic resin composition is used to prepare optical molded articles, optical lenses and optical films.

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