Resin composition, and optical lens and optical film containing same

Abstract

The present invention enables providing a resin composition characterized by containing: a resin containing a constituent unit (A) represented by general formula (1); and a resin containing a constituent unit (B) represented by general formula (2) and / or a constituent unit (C) represented by general formula (3). (In general formula (1), R1 represents a methyl group or an ethyl group, R2 and R3 independently represent a hydrogen atom or a methyl group, and n represents 0 or 1.) (In general formula (2), Ra and Rb independently represent a hydrogen atom, etc., Rh represents an aryl group of 6-20 carbons, X represents a single bond or a fluorene group, A and B independently represent an alkylene group of 1-4 carbons, m and n independently represent integers 0-6, and a and b independently represent integers 0-10.) (In general formula (3), Rc and Rd independently represent a hydrogen atom, etc., Y represents a fluorene group, A and B independently represent an alkylene group of 1-4 carbons, p and q independently represent integers 0-4, and a and b independently represent integers 0-10.)

Description

[Technical field]

[0001] The present invention relates to a resin composition and an optical lens and an optical film containing the same. [Background technology]

[0002] Optical glass or optical transparent resin is used as a material for optical elements used in the optical systems of liquid crystal display devices, optical disk devices, and projection screens, as well as the optical systems of various cameras such as cameras, film-integrated cameras, and video cameras. Optical glass is excellent in heat resistance, transparency, dimensional stability, chemical resistance, etc., and there are many types of materials with various refractive indices (nd) and Abbe numbers (νd). However, it has problems such as high material costs, poor moldability, and low productivity. In particular, processing it into aspherical lenses used for aberration correction requires extremely advanced technology and high costs, which is a major obstacle to practical use.

[0003] In contrast to the above optical glass, optical lenses made of optical transparent resins, especially thermoplastic transparent resins, have the advantage that they can be mass-produced by injection molding and that aspherical lenses can be easily manufactured, and are currently used mainly for camera lenses. Examples of optical transparent resins include polyester resins (Patent Documents 1 to 3), polycarbonate resins made of bisphenol A, polymethyl methacrylate, and the like.

[0004] In general, in camera optical systems, aberration correction is performed using multiple concave and convex lenses with different optical properties to improve the quality of color images. One example is chromatic aberration correction that combines a concave lens with a high refractive index and low Abbe number with a convex lens with a low refractive index and high Abbe number. In this case, the concave lens produces chromatic aberration with the opposite sign to that of the convex lens, synthetically canceling out the chromatic aberration produced by the convex lens. As chromatic aberration increases, color bleeding increases, resulting in an extreme decrease in color image quality.

[0005] Under these circumstances, there is a demand for a resin composition and an optical lens having excellent continuous moldability, a high refractive index and a low Abbe number, but these have not yet been provided. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] Patent No. 5849967 [Patent Document 2] WO2015 / 163323A1 [Patent Document 3] WO2018 / 62327A1 Summary of the Invention [Problem to be solved by the invention]

[0007] The problem to be solved by the present invention is to provide a resin composition having excellent continuous moldability, a high refractive index, and a low Abbe number. Another object of the present invention is to provide an excellent optical lens by using the resin composition. [Means for solving the problem]

[0008] Means for Solving the Problems The present inventors conducted extensive research to solve the above problems, and as a result, found that the above problems could be solved by the following resin composition and optical lens, thereby completing the present invention. The present invention is, for example, as follows. <1> A resin containing a structural unit (A) represented by the following general formula (1), and a resin containing a structural unit (B) represented by the following general formula (2) and / or a structural unit (C) represented by the following general formula (3). [ka] (In general formula (1), R1 represents a hydrogen atom, a methyl group, or an ethyl group, R2 and R3 each independently represent a hydrogen atom or a methyl group, and n represents 0 or 1.) [ka] (In general formula (2), R a and R b each independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, a cycloalkoxy group having 5 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 6 to 20 carbon atoms containing one or more hetero ring atoms selected from O, N, and S, or an aryloxy group having 6 to 20 carbon atoms, and -C≡CR h is selected from the group consisting of R h represents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 6 to 20 carbon atoms containing one or more hetero ring atoms selected from O, N, and S, X represents a single bond or a fluorene group; A and B each independently represent an alkylene group having 1 to 4 carbon atoms; m and n each independently represent an integer of 0 to 6; a and b each independently represent an integer of 0 to 10. [ka] (In general formula (3), R c and R d are each independently selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxyl group having 1 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, a cycloalkoxyl group having 5 to 20 carbon atoms, and an aryl group having 6 to 20 carbon atoms; Y represents a fluorene group; A and B each independently represent an alkylene group having 1 to 4 carbon atoms; p and q each independently represent an integer of 0 to 4; a and b each independently represent an integer of 0 to 10. <2> The resin containing the structural unit (A) represented by the general formula (1) is a polyester resin, and the resin containing the structural unit (B) represented by the general formula (2) and / or the structural unit (C) represented by the general formula (3) is a polycarbonate resin. <1> The resin composition according to claim 1, <3> The above-mentioned resin further contains a structural unit (D) represented by the following general formula (4): <1> or <2> The resin composition according to claim 1, [ka] (In general formula (4), R4 represents a hydrogen atom, a methyl group, or an ethyl group, and R5 and R6 each independently represent a hydrogen atom or a methyl group.) <4> The resin containing the structural unit (D) represented by the general formula (4) is a polycarbonate resin. <3> The resin composition according to claim 1, <5> The structural unit (B) represented by the general formula (2) includes at least one of a structural unit represented by the following general formula (2a) and a structural unit represented by the following general formula (2b): <1> from <4> The resin composition according to any one of claims 1 to 5, [ka] (In general formula (2a), R a , R b , A, B, a, and b are each defined as in general formula (2). [ka] (In the general formula (2b), A, B, a, and b are the same as those in the general formula (2). R e and R f are each independently selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxyl group having 1 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, a cycloalkoxyl group having 5 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, and an aryloxy group having 6 to 20 carbon atoms. <6> R in the general formula (2) a and R beach independently represents a hydrogen atom, a phenyl group, a naphthyl group, or a substituent selected from the group consisting of the following: <1> from <5> The resin composition according to any one of claims 1 to 5, [ka] <7> The structural unit (C) represented by the general formula (3) includes a structural unit represented by the following general formula (3a): <1> from <6> The resin composition according to any one of claims 1 to 5, [ka] (In the general formula (3a), A, B, a, and b are the same as those in the general formula (3). R e and R f are each independently selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxyl group having 1 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, a cycloalkoxyl group having 5 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, and an aryloxy group having 6 to 20 carbon atoms. <8> The above-mentioned, wherein the mass ratio (A / B) of the structural unit (A) to the structural unit (B) is 99 / 1 to 1 / 99. <1> from <7> The resin composition according to any one of claims 1 to 5, <9> The above-mentioned, wherein the mass ratio (A / C) of the structural unit (A) to the structural unit (C) is 99 / 1 to 1 / 99. <1> from <8> The resin composition according to any one of claims 1 to 5, <10> The above-mentioned, wherein the mass ratio (A / D) of the structural unit (A) to the structural unit (D) is 99 / 1 to 1 / 99. <3> or <4> The resin composition according to claim 1, <11> The above composition further contains an antioxidant. <1> from <10> The resin composition according to any one of claims 1 to 5, <12> The antioxidant is a phosphite-based antioxidant and / or a phenol-based antioxidant. <11> The resin composition according to claim 1, <13> In the general formula (1), R1, R2 and R3 each represent a hydrogen atom, and n represents 1. <1> from <12> The resin composition according to any one of claims 1 to 5, <14> the above <1> from <13> 2. A molded article comprising the resin composition according to claim 1. <15> The molded article is an optical lens. <14> The molded article is as described above. <16> The molded article is an optical film. <14> The molded article is as described above. Effect of the Invention

[0009] The resin composition of the present invention has excellent continuous moldability, a high refractive index, and a low Abbe number. Furthermore, by using the resin composition of the present invention, an excellent optical lens can be obtained. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0010] Hereinafter, an embodiment for carrying out the present invention (hereinafter, simply referred to as "the present embodiment") will be described in detail. The following embodiment is an example for explaining the present invention, and is not intended to limit the present invention to the following content. The present invention can be carried out by appropriately modifying it within the scope of its gist. [Resin containing structural unit (A)] The resin composition of the present embodiment contains a resin containing a structural unit (A) represented by the following general formula (1) (hereinafter, also simply referred to as "structural unit (A)"), and further contains a resin containing a structural unit (B) represented by the below-mentioned general formula (2) and / or a structural unit (C) represented by the below-mentioned general formula (3). The resin containing the structural unit (A) is preferably a polyester resin or polyester carbonate resin, and more preferably a polyester resin, because it has a relatively high refractive index, a relatively high glass transition temperature (Tg), and good heat resistance. The resin containing the structural unit (A) may contain any of a random, block, and alternating copolymer structure. The weight average molecular weight (Mw) of the resin containing the structural unit (A) is not particularly limited as long as it has the effects of the present invention, but in consideration of the balance between mechanical strength and moldability, it is preferably 10,000 to 100,000, more preferably 10,000 to 50,000, even more preferably 15,000 to 45,000, and even more preferably 20,000 to 40,000. The weight average molecular weight (Mw) can be measured by the method described in the Examples below.

[0011] [ka]

[0012] In the general formula (1), R1 represents a hydrogen atom, a methyl group, or an ethyl group; R2 and R3 each independently represent a hydrogen atom or a methyl group; and n represents 0 or 1. In general formula (1), R1 preferably represents a hydrogen atom or a methyl group, and R2 and R3 preferably represent a hydrogen atom. In this embodiment, from the viewpoint of heat resistance, it is more preferable that R1, R2, and R3 in general formula (1) are hydrogen atoms. In addition, in the general formula (1), n ​​is preferably 1 from the viewpoint of further improving heat resistance.

[0013] In this embodiment, in consideration of the balance between heat resistance and optical properties, the content of the structural unit (A) relative to all structural units contained in the resin containing the structural unit (A) is preferably 10 to 95 mol %. When the content is 10 mol % or more, sufficiently good heat resistance and optical properties tend to be obtained. In addition, when the content is 95 mol % or less, moldability can be improved while good heat resistance and optical properties are ensured, which is preferable. From the same viewpoint as above, the content of the structural unit (A) is more preferably 15 to 95 mol %, and even more preferably 20 to 95 mol %.

[0014] In one preferred embodiment, the resin composition of the present invention contains a homopolyester resin composed of the structural unit (A).

[0015] In one preferred embodiment, the resin composition of the present invention contains, in addition to the structural unit (A), a copolymer resin (preferably a copolymer polyester resin) containing the structural unit (A-2) and the structural unit (A-3) described below.

[0016] The structural unit (A-2) is not particularly limited as long as it is a unit derived from a diol, and specific examples thereof include ethylene glycol, trimethylene glycol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, diethylene glycol, propylene glycol, neopentyl glycol, 1,3-cyclohexanedimethanol, 1,4-cyclohexanedimethanol, 1,2-decahydronaphthalenedimethanol, 1,3-decahydronaphthalenedimethanol, 1,4-decahydronaphthalenedimethanol, 1,5-decahydronaphthalenedimethanol, and 1,6-decahydronaphthalenedimethanol. Dronaphthalenedimethanol, 1,6-decahydronaphthalenedimethanol, 2,7-decahydronaphthalenedimethanol, tetralin dimethanol, norbornane dimethanol, tricyclodecane dimethanol, pentacyclopentadecanedimethanol, decahydro-1,4:5,8-dimethanonaphthalenedimethanol, norbornanediol, cyclohexanediol, 2,2'-bis(4-hydroxycyclohexyl)propane, adamantanediol, decahydro-1,4:5,8-dimethanonaphthalenediol, 9,9-bis[4-(2- 9,9-bis[4-(2-hydroxypropoxy)phenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-methylphenyl]fluorene, 9,9-bis[4-(2-hydroxypropoxy)-3-methylphenyl]fluorene, 9,9-bis[4-(2-hydroxypropoxy)-3-methylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-phenylphenyl]fluorene, 9,9-bis[4-(2-hydroxypropoxy)-3-phenylphenyl]fluorene, Examples of units derived from diols include 9,9-bis[6-(2-hydroxyethoxy)-2-naphthyl]fluorene, 9,9-bis[6-(2-hydroxypropoxy)-2-naphthyl]fluorene, 9,9-bis(2-hydroxyethyl)fluorene, xylylene glycol, 3,9-bis(1,1-dimethyl-2-hydroxyethyl)-2,4,8,10-tetraoxaspiro[5.5]undecane, 1,4:3,6-dianhydro-D-sorbitol, and 2,2,4,4-tetramethyl-1,3-cyclobutanediol.

[0017] The structural unit (A-2) is preferably a unit derived from an aliphatic diol or a diol having a fluorene structure, since good optical properties can be obtained. In addition, the unit derived from the diol having the fluorene structure is more preferably one having a cardo structure together with the fluorene structure. As the unit derived from such an aliphatic diol, more preferably, the unit derived from 1,4-cyclohexanedimethanol, ethylene glycol, 3,9-bis(1,1-dimethyl-2-hydroxyethyl)-2,4,8,10-tetraoxaspiro[5.5]undecane, 1,4:3,6-dianhydro-D-sorbitol, or decahydro-1,4:5,8-dimethanonaphthalenedimethanol is more preferable. As the unit derived from a diol having a fluorene structure, 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-methylphenyl]fluorene, and 9,9-bis[4-(2-hydroxyethoxy)-3-phenylphenyl]fluorene are more preferable. The optical isomers of these are not particularly limited and may be any of cis isomers, trans isomers, and mixtures thereof. The above-mentioned units may be contained alone or in combination of two or more kinds.

[0018] The structural unit (A-3) is not particularly limited as long as it is a unit derived from a dicarboxylic acid or an ester-forming derivative thereof, and specific examples thereof include structural units derived from aromatic dicarboxylic acids and / or derivatives thereof, such as terephthalic acid, isophthalic acid, phthalic acid, 1,3-naphthalenedicarboxylic acid, 1,4-naphthalenedicarboxylic acid, 1,5-naphthalenedicarboxylic acid, 2,6-naphthalenedicarboxylic acid, 2,7-naphthalenedicarboxylic acid, 2-methylterephthalic acid, biphenyldicarboxylic acid, and tetralindicarboxylic acid; succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, decanedicarboxylic acid, dodecanedicarboxylic acid, cyclohexanedicarboxylic acid, decalindicarboxylic acid, norbornanedicarboxylic acid, tricyclodecanedicarboxylic acid, pentacyclopentadecanedicarboxylic acid, 3,9-bis(1,1-dimethyl-2-carboxyethyl)-2,4,8,10-tetraoxaspiro[5.5]undecane, 5-caproic acid, and the like. units derived from aliphatic dicarboxylic acids and / or derivatives thereof, such as carboxy-5-ethyl-2-(1,1-dimethyl-2-carboxyethyl)-1,3-dioxane, 1,4:5,8-dimethanodecahydronaphthalene dicarboxylic acid, adamantanedicarboxylic acid, and dimer acid; units derived from 9,9-bis(carboxymethyl)fluorene, 9,9-bis(1-carboxyethyl)fluorene, 9,9-bis(2-carboxyethyl)fluorene, 9,9-bis(1-carboxypropyl)fluorene, Examples of units derived from dicarboxylic acids and / or derivatives thereof having a fluorene structure include 9,9-bis(2-carboxypropyl)fluorene, 9,9-bis(2-carboxy-1-methylethyl)fluorene, 9,9-bis(2-carboxy-1-methylpropyl)fluorene, 9,9-bis(2-carboxybutyl)fluorene, 9,9-bis(2-carboxy-1-methylbutyl)fluorene, and 9,9-bis(5-carboxypentyl)fluorene.

[0019] The structural unit (A-3) is preferably a unit derived from an aliphatic dicarboxylic acid or an ester-forming derivative thereof, or a dicarboxylic acid having a fluorene structure or an ester-forming derivative thereof, since good optical properties can be obtained. In addition, the unit derived from the dicarboxylic acid having a fluorene structure or an ester-forming derivative thereof is more preferably one having a cardo structure together with the fluorene structure. As the unit derived from an aliphatic dicarboxylic acid or an ester-forming derivative thereof, a unit derived from dimethyl 1,4-cyclohexanedicarboxylate is more preferable from the viewpoint of the balance of physical properties between heat resistance and optical properties. As the unit derived from a dicarboxylic acid having a fluorene structure or an ester-forming derivative thereof, a unit derived from 9,9-bis(methoxycarbonylmethyl)fluorene, 9,9-bis(2-methoxycarbonylethyl)fluorene, or 9,9-bis(methoxycarbonylpropyl)fluorene is more preferable from the viewpoint of the balance of physical properties between heat resistance and optical properties. In addition, these optical isomers may be any of cis isomers, trans isomers, or mixtures thereof, and are not particularly limited. The above-mentioned units may be contained alone or in combination of two or more kinds.

[0020] In this embodiment, the resin containing the structural unit (A) may contain other structural units such as a hydroxyl group and a carboxylic acid or its ester-forming derivative structural unit (A-4) in addition to the structural unit (A), the structural unit (A-2), and the structural unit (A-3). The structural unit (A-4) is not particularly limited, but examples thereof include structural units derived from oxyacids and / or derivatives thereof, such as glycolic acid, lactic acid, hydroxybutyric acid, 2-hydroxyisobutyric acid, hydroxybenzoic acid, 6-hydroxycaproic acid, and 4-hydroxycyclohexanecarboxylic acid.

[0021] In this embodiment, the resin containing the structural unit (A) is not particularly limited as long as it has the effects of the present invention; however, it is preferable that the resin satisfies any one or more of the following (1) to (3), and it is more preferable that the resin satisfies all of the following (1) to (3).

[0022] (1) In this embodiment, the glass transition temperature (Tg) of the resin containing the structural unit (A) is not particularly limited as long as it has the effect of the present invention, but from the viewpoint of ensuring sufficient heat resistance, it is preferably 120°C or higher, more preferably 130°C or higher, and even more preferably 140°C or higher. The upper limit is not particularly limited, but is, for example, 240°C. The Tg can be measured by the method described in the examples below. The Tg can be adjusted to the above range, for example, by appropriately adjusting the copolymerization ratio of the raw material monomers of the polyester resin.

[0023] The resin containing the structural unit (A) in the present invention has excellent optical properties (refractive index, Abbe number). In particular, by having a specific structure, the refractive index and Abbe number can be adjusted arbitrarily while maintaining excellent continuous moldability and heat resistance. For example, the refractive index and Abbe number can be adjusted to the following ranges by appropriately adjusting the copolymerization ratio of the raw material monomers of the polyester resin.

[0024] (2) The refractive index (nd) for d-line wavelength light is not particularly limited as long as the effect of the present invention is obtained, but is preferably 1.60 or less, more preferably 1.59 or less, even more preferably 1.58 or less, even more preferably 1.57 or less, and particularly preferably 1.56 or less. Considering practical use as an optical lens, the lower limit of the refractive index is not particularly limited, but is about 1.40, 1.48, 1.49, or 1.50. The refractive index for the d-line wavelength light can be measured by the method described in the examples below.

[0025] (3) The Abbe number (νd) is not particularly limited as long as the effect of the present invention is achieved, but is preferably 28 or more, more preferably 30 or more, even more preferably 31 or more, even more preferably 35 or more, and particularly preferably 40 or more. In consideration of practical use as an optical lens, the upper limit of the Abbe number is not particularly limited, but is about 70, 60, 59, or 58. The Abbe number can be measured by the method described in the examples below.

[0026] The Abbe number (νd) is a value expressed by the formula (1) described in the examples, and indicates the wavelength dependency of the refractive index. Therefore, a material with a high Abbe number has a small change in refractive index due to wavelength, and has little chromatic aberration.

[0027] Furthermore, when using a resin containing the structural unit (A) of this embodiment, it is preferable to add various additives such as antioxidants, release agents, ultraviolet absorbers, colorants, light stabilizers, lubricants, plasticizers, flow modifiers, thickeners, flame retardants, crystal nucleating agents, compatibilizers, reinforcing agents, extenders, dyes, antistatic agents, antibacterial agents, matting agents, drying regulators, antisettling agents, surfactants, drying oils, waxes, fillers, reinforcing agents, surface smoothing agents, leveling agents, polymerization metal deactivators, and curing reaction accelerators, as well as known additives such as molding aids, within a range that does not impair the object of this embodiment.

[0028] [Method for producing resin containing structural unit (A)] The resin containing the structural unit (A) can be obtained by homopolymerizing a monomer (monomer, raw material monomer) corresponding to the structural unit (A) or by copolymerizing each monomer corresponding to the structural unit (A), the structural unit (A-2) and the structural unit (A-3). The method for producing the monomer corresponding to the structural unit (A) will be described below. Such a monomer is, for example, represented by the following general formula (1-2).

[0029] [ka]

[0030] In general formula (1-2), R1 represents a hydrogen atom, a methyl group, or an ethyl group, R2 and R3 each independently represent a hydrogen atom or a methyl group, and X represents a hydrogen atom or a hydrocarbon group having 4 or less carbon atoms which may contain a hydroxyl group. In the general formula (1-2), R1 preferably represents a hydrogen atom or a methyl group. R2 and R3 preferably represent a hydrogen atom. The hydrocarbon group is not limited to the following, but examples thereof include a methyl group, an ethyl group, a propyl group, a butyl group, a vinyl group, a 2-hydroxyethyl group, and a 4-hydroxybutyl group.

[0031] When producing a resin containing the structural unit (A) of this embodiment, an ester exchange catalyst, an esterification catalyst, a polycondensation catalyst, etc., which are used in the production of a normal polyester resin, can be used. Although these catalysts are not particularly limited, for example, compounds of metals such as zinc, lead, cerium, cadmium, manganese, cobalt, lithium, sodium, potassium, calcium, nickel, magnesium, vanadium, aluminum, titanium, antimony, germanium, tin, etc. (for example, fatty acid salts, carbonates, phosphates, hydroxides, chlorides, oxides, alkoxides), and metallic magnesium, etc. can be mentioned. These can be used alone or in combination of two or more. As the catalyst, among the above, compounds of manganese, cobalt, zinc, titanium, calcium, antimony, germanium, and tin are preferred, and compounds of manganese, titanium, antimony, germanium, and tin are more preferred. The amount of these catalysts used is not particularly limited, but for example, the amount as a metal component relative to the raw material of the polyester resin is preferably 1 to 1000 ppm, more preferably 3 to 750 ppm, and even more preferably 5 to 500 ppm.

[0032] The reaction temperature in the polymerization reaction depends on the type of catalyst, the amount used, etc., but is usually selected in the range of 150° C. to 300° C., and in consideration of the reaction rate and coloration of the resin, it is preferably 180° C. to 280° C. The pressure in the reaction tank is preferably adjusted from the atmospheric pressure to 1 kPa or less, and more preferably 0.5 kPa or less.

[0033] When carrying out the polymerization reaction, a phosphorus compound may be added as desired. Examples of phosphorus compounds include, but are not limited to, phosphoric acid, phosphorous acid, phosphoric acid esters, and phosphorous acid esters. Examples of phosphorous acid esters include, but are not limited to, methyl phosphate, ethyl phosphate, butyl phosphate, phenyl phosphate, dimethyl phosphate, diethyl phosphate, dibutyl phosphate, diphenyl phosphate, trimethyl phosphate, triethyl phosphate, tributyl phosphate, and triphenyl phosphate. Examples of phosphorous acid esters include, but are not limited to, methyl phosphite, ethyl phosphite, butyl phosphite, phenyl phosphite, dimethyl phosphite, diethyl phosphite, dibutyl phosphite, diphenyl phosphite, trimethyl phosphite, triethyl phosphite, tributyl phosphite, and triphenyl phosphite. These may be used alone or in combination of two or more. The concentration of phosphorus atoms in the resin containing the structural unit (A) of this embodiment is preferably 1 to 500 ppm, more preferably 5 to 400 ppm, and even more preferably 10 to 200 ppm.

[0034] In addition, when producing a resin containing the structural unit (A) of this embodiment, various stabilizers such as an etherification inhibitor, a heat stabilizer, a light stabilizer, and a polymerization regulator may be used.

[0035] To the resin containing the structural unit (A) of this embodiment, various additives such as antioxidants, release agents, ultraviolet absorbers, colorants, light stabilizers, lubricants, plasticizers, flow modifiers, thickeners, flame retardants, crystal nucleating agents, compatibilizers, reinforcing agents, extenders, dyes, antistatic agents, antibacterial agents, matting agents, drying regulators, anti-settling agents, surfactants, drying oils, waxes, fillers, reinforcing agents, surface smoothing agents, leveling agents, polymerization metal deactivators, and curing reaction accelerators, and molding aids can be added, provided the object of this embodiment is not impaired.

[0036] [Resin containing structural unit (B) and / or structural unit (C)] The resin composition of the present embodiment contains, in addition to a resin containing the structural unit (A) described above, a resin containing a structural unit (B) represented by the following general formula (2) (hereinafter also simply referred to as "structural unit (B)") and / or a structural unit (C) represented by the following general formula (3) (hereinafter also simply referred to as "structural unit (C)". It is particularly preferable that the resin containing the structural unit (B) and / or the structural unit (C) is a polycarbonate resin, as this has a relatively low water absorption rate and excellent mechanical strength. In the following, the case where the resin containing the structural unit (B) and / or the structural unit (C) is a polycarbonate resin will be described, but the resin may be a resin other than a polycarbonate resin, such as a polyester resin or a polyestercarbonate resin. [ka] In general formula (2), R a and R b each independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, a cycloalkoxy group having 5 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 6 to 20 carbon atoms containing one or more hetero ring atoms selected from O, N, and S, or an aryloxy group having 6 to 20 carbon atoms, and -C≡CR h is selected from the group consisting of R h represents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 6 to 20 carbon atoms containing one or more hetero ring atoms selected from O, N, and S, X represents a single bond or a fluorene group; A and B each independently represent an alkylene group having 1 to 4 carbon atoms, and preferably an alkylene group having 2 carbon atoms; m and n each independently represent an integer of 0 to 6, preferably an integer of 0 to 2, more preferably 0 or 1; a and b each independently represent an integer of 0 to 10, preferably an integer of 1 to 3, and more preferably 1.

[0037] R in general formula (2)a and R b Each of the groups preferably independently represents a hydrogen atom, a phenyl group, a naphthyl group, or a substituent selected from the group consisting of the following: [ka]

[0038] Examples of the naphthyl group include the following. [ka]

[0039] R in general formula (2) a and R b each independently represents a hydrogen atom, a phenyl group, or [ka] It is preferred that

[0040] The structural unit (B) represented by general formula (2) preferably contains at least one of a structural unit represented by the following general formula (2a) and a structural unit represented by the following general formula (2b). [ka] In general formula (2a), R a , R b , A, B, a and b are each defined as in formula (2). [ka] In the general formula (2b), A, B, a, and b are the same as those in the general formula (2). e and R f are each independently selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxyl group having 1 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, a cycloalkoxyl group having 5 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, and an aryloxy group having 6 to 20 carbon atoms. eand R f more preferably, each independently represents a hydrogen atom, a phenyl group, a naphthyl group, or a methyl group, and particularly preferably represents a hydrogen atom.

[0041] In the resin composition of this embodiment, the mass ratio (A / B) of the structural unit (A) to the structural unit (B) is preferably from 99 / 1 to 1 / 99, more preferably from 95 / 5 to 5 / 95, and particularly preferably from 90 / 10 to 10 / 90. [ka] In general formula (3), R c and R d are each independently selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxyl group having 1 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, a cycloalkoxyl group having 5 to 20 carbon atoms, and an aryl group having 6 to 20 carbon atoms, and preferably represent a hydrogen atom, a methyl group, or a phenyl group; Y represents a fluorene group; A and B each independently represent an alkylene group having 1 to 4 carbon atoms, and preferably an alkylene group having 2 carbon atoms; p and q each independently represent an integer of 0 to 4, preferably an integer of 0 to 2, more preferably 0 or 1; a and b each independently represent an integer of 0 to 10, preferably an integer of 1 to 3, and more preferably 1.

[0042] The structural unit (C) represented by general formula (3) preferably contains a structural unit represented by the following general formula (3a). [ka] In the general formula (3a), A, B, a, and b are each defined as in the general formula (3). e and R fare each independently selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxyl group having 1 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, a cycloalkoxyl group having 5 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, and an aryloxy group having 6 to 20 carbon atoms. e and R f more preferably, each independently represents a hydrogen atom, a phenyl group, a naphthyl group, or a methyl group, and particularly preferably represents a hydrogen atom.

[0043] In the resin composition of this embodiment, the mass ratio (A / C) of the structural unit (A) to the structural unit (C) is preferably from 99 / 1 to 1 / 99, more preferably from 95 / 5 to 30 / 70, and particularly preferably from 95 / 5 to 50 / 50.

[0044] The polycarbonate resin used in the present invention contains at least one of the structural unit (B) and the structural unit (C), and preferably consists essentially of either the structural unit (B) or the structural unit (C). For example, of the structural units of the polycarbonate resin used in the present invention, preferably 90% or more, more preferably 95% or more, and even more preferably 98% or more are made up of the structural unit (B) or the structural unit (C).

[0045] When the polycarbonate resin used in the present invention contains both the structural unit (B) and the structural unit (C), there is no particular limitation on how these structural units are contained in the resin. In one embodiment of the present invention, the polycarbonate resin may contain a copolymer containing the structural unit (B) and the structural unit (C), or may be a binary resin containing a homopolymer composed of each structural unit.

[0046] The polycarbonate resin used in the present invention may have any of a random, block and alternating copolymer structure.

[0047] The polycarbonate resin used in the present invention preferably has a weight average molecular weight (Mw) of 10,000 to 100,000. In this specification, the term "weight average molecular weight (Mw)" means "polystyrene equivalent weight average molecular weight (Mw)". The weight average molecular weight (Mw) in terms of polystyrene is more preferably 10,000 to 50,000, further preferably 15,000 to 45,000, and even more preferably 20,000 to 40,000. If Mw is less than 10,000, the molded article will be brittle, which is undesirable.If Mw is more than 100,000, the melt viscosity will be high, making it difficult to remove the resin after production, and furthermore, the flowability will be poor, making it difficult to perform injection molding in a molten state, which is undesirable.

[0048] The refractive index (nd) of the polycarbonate resin used in the present invention at 23°C and a wavelength of 587.6 nm is preferably 1.635 to 1.695, more preferably 1.640 to 1.690, even more preferably 1.645 to 1.685, and particularly preferably 1.660 to 1.685. The polycarbonate resin used in the present invention has a high refractive index (nd) and is suitable for optical lens materials. The refractive index can be measured by the method described in the examples below.

[0049] The Abbe number (νd) of the polycarbonate resin used in the present invention is preferably 70 or less, more preferably 30 or less, even more preferably 24 or less, still more preferably 22 or less, and particularly preferably 20 or less. The lower limit of the Abbe number is about 14, 16, 17, or 18. The Abbe number can be measured by the method described in the examples below.

[0050] To the polycarbonate resin of the present invention, various additives such as antioxidants, release agents, ultraviolet absorbers, colorants, light stabilizers, lubricants, plasticizers, flow modifiers, thickeners, flame retardants, crystal nucleating agents, compatibilizers, reinforcing agents, extenders, dyes, antistatic agents, antibacterial agents, matting agents, drying regulators, antisettling agents, surfactants, drying oils, waxes, fillers, reinforcing agents, surface smoothing agents, leveling agents, polymerization metal deactivators, and curing reaction accelerators, and molding aids may be added, provided the purpose of this embodiment is not impaired.

[0051] The ultraviolet absorber is preferably at least one ultraviolet absorber selected from the group consisting of benzotriazole ultraviolet absorbers, benzophenone ultraviolet absorbers, triazine ultraviolet absorbers, cyclic iminoester ultraviolet absorbers, and cyanoacrylate ultraviolet absorbers. That is, the ultraviolet absorbers listed below may be used alone or in combination of two or more.

[0052] Benzotriazole-based ultraviolet absorbers include 2-(2-hydroxy-5-methylphenyl)benzotriazole, 2-(2-hydroxy-5-tert-octylphenyl)benzotriazole, 2-(2-hydroxy-3,5-dicumylphenyl)phenylbenzotriazole, 2-(2-hydroxy-3-tert-butyl-5-methylphenyl)-5-chlorobenzotriazole, 2,2'-methylenebis[4-(1,1,3,3-tetramethylbutyl)-6-(2N-benzotriazol-2-yl)phenol], 2-(2-hydroxy-3,5-di-tert-butylphenyl)benzotriazole, 2-(2-hydroxy-3,5-di-tert-butyl phenyl)-5-chlorobenzotriazole, 2-(2-hydroxy-3,5-di-tert-amylphenyl)benzotriazole, 2-(2-hydroxy-5-tert-octylphenyl)benzotriazole, 2-(2-hydroxy-5-tert-butylphenyl)benzotriazole, 2-(2-hydroxy-4-octoxyphenyl)benzotriazole, 2,2'-methylenebis(4-cumyl-6-benzotriazolephenyl), 2,2'-p-phenylenebis(1,3-benzoxazin-4-one), 2-[2-hydroxy-3-(3,4,5,6-tetrahydrophthalimidomethyl)-5-methylphenyl]benzotriazole, and the like.

[0053] Benzophenone-based ultraviolet absorbers include 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-octoxybenzophenone, 2-hydroxy-4-benzyloxybenzophenone, 2-hydroxy-4-methoxy-5-sulfoxybenzophenone, 2-hydroxy-4-methoxy-5-sulfoxytrihydridolate benzophenone, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2',4,4'-tetrahydroxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxy-5-sodium sulfoxybenzophenone, bis(5-benzoyl-4-hydroxy-2-methoxyphenyl)methane, 2-hydroxy-4-n-dodecyloxybenzophenone, and 2-hydroxy-4-methoxy-2'-carboxybenzophenone.

[0054] Examples of triazine-based ultraviolet absorbers include 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-[(hexyl)oxy]-phenol and 2-(4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl)-5-[(octyl)oxy]-phenol.

[0055] Examples of cyclic iminoester-based ultraviolet absorbers include 2,2'-bis(3,1-benzoxazine-4-one), 2,2'-p-phenylenebis(3,1-benzoxazine-4-one), 2,2'-m-phenylenebis(3,1-benzoxazine-4-one), 2,2'-(4,4'-diphenylene)bis(3,1-benzoxazine-4-one), 2,2'-(2,6-naphthalene)bis(3,1-benzoxazine-4-one), 2,2'-(1,5-naphthalene)bis(3,1-benzoxazin-4-one), 2,2'-(2-methyl-p-phenylene)bis(3,1-benzoxazin-4-one), 2,2'-(2-nitro-p-phenylene)bis(3,1-benzoxazin-4-one), and 2,2'-(2-chloro-p-phenylene)bis(3,1-benzoxazin-4-one).

[0056] Examples of cyanoacrylate ultraviolet absorbers include 1,3-bis-[(2'-cyano-3',3'-diphenylacryloyl)oxy]-2,2-bis[(2-cyano-3,3-diphenylacryloyl)oxy]methyl)propane and 1,3-bis-[(2-cyano-3,3-diphenylacryloyl)oxy]benzene.

[0057] The content of the ultraviolet absorbing agent is preferably 0.01 to 3.0 parts by mass, more preferably 0.02 to 1.0 parts by mass, and further preferably 0.05 to 0.8 parts by mass, relative to 100 parts by mass of the polycarbonate resin. If the blending amount is within this range, it is possible to impart sufficient weather resistance to the polycarbonate resin depending on the application.

[0058] Examples of the bluing agent include Solvent Violet 13 (CA.No (Color Index No.) 60725; trademarks: LANXESS "Macrolex Violet B", Mitsubishi Chemical "Diaresin Blue G", and Sumitomo Chemical "Sumiplast Violet B"); Solvent Violet 14; Solvent Violet 31 (CA.No. 68210; trademark: Mitsubishi Chemical "Diaresin Violet D"); Solvent Violet 33 (CA.No. 60725; trademark: Mitsubishi Chemical "Diaresin Blue J"); Solvent Violet 36 (CA.No. 68210; trademark: LANXESS "Macrolex Violet 3R"); Solvent Blue 45 (CA.No. 61110; trademark: Sandoz "Tetrazole Blue RLS"); Examples of the bluing agent include Blue 94 [CA. No. 61500; trade name "Dia Resin Blue N" manufactured by Mitsubishi Chemical Corporation], Solvent Blue 97 [Macrolex Blue RR manufactured by Lanxess AG], Solvent Blue 45, Solvent Blue 87, and Disperse Violet 28. The bluing agent is added to eliminate the yellow color of the optical lens, and one type may be used alone or two or more types may be used in combination. The amount of the bluing agent added is preferably 0.00001 to 0.005 parts by mass, more preferably 0.00001 to 0.0005 parts by mass, and even more preferably 0.00001 to 0.0002 parts by mass, relative to 100 parts by mass of the polycarbonate resin.

[0059] [Method for producing a resin containing structural unit (B) and / or structural unit (C)] When producing a polycarbonate resin containing the structural unit (B) used in the present invention, it can be preferably produced by using at least one of the compounds represented by the following general formula (2a') and the following general formula (2b') as a dihydroxy component and reacting it with a carbonate precursor such as a carbonic acid diester. Specifically, it can be produced by reacting the dihydroxy component and the carbonate precursor such as a carbonic acid diester by a melt polycondensation method in the presence of a basic compound catalyst or an ester exchange catalyst or a mixed catalyst consisting of both, or in the absence of a catalyst. [ka] In general formula (2a'), R a , R b , A, B, a and b are each defined as in formula (2a).

[0060] Examples of dihydroxy compounds represented by the general formula (2a') include 2,2'-bis(1-hydroxymethoxy)-1,1'-binaphthalene, 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene, 2,2'-bis(3-hydroxypropyloxy)-1,1'-binaphthalene, and 2,2'-bis(4-hydroxybutoxy)-1,1'-binaphthalene. Among these, 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene (hereinafter sometimes abbreviated as "BNE") is preferred. These may be used alone or in combination of two or more.

[0061] The compound in general formula (2a') where a and b are not the same (i.e., a≠b) is preferably present in a total amount of 50 ppm or less, and more preferably 20 ppm or less, in the monomer mainly composed of the compound of general formula (2a').

[0062] [ka] In general formula (2b'), R e , R f, A, B, a and b are each defined as in general formula (2b).

[0063] Examples of the compound of general formula (2b') include 9,9-bis(hydroxy(poly)alkoxynaphthyl)fluorenes. For example, examples of the compound of general formula (2b') include 9,9-bis[6-(1-hydroxymethoxy)naphthalene-2-yl]fluorene, 9,9-bis[6-(2-hydroxyethoxy)naphthalene-2-yl]fluorene, 9,9-bis[6-(3-hydroxypropoxy)naphthalene-2-yl]fluorene, and 9,9-bis[6-(4-hydroxybutoxy)naphthalene-2-yl]fluorene. Among them, 9,9-bis[6-(2-hydroxyethoxy)naphthalene-2-yl]fluorene is preferred. These may be used alone or in combination of two or more.

[0064] When producing the compound of general formula (2b'), fluorenone, one of the raw materials, may be contained as an impurity. The content of fluorenone in the monomer mainly composed of the compound of general formula (2b') is preferably 1000 ppm or less, more preferably 100 ppm or less, even more preferably 50 ppm or less, and particularly preferably 10 ppm or less. The fluorenone contained in the monomer mainly composed of the compound of general formula (2b') may remain in the resin after polymerization. The lower the content of fluorenone, the better the hue of the resin, which is preferable. Furthermore, although it is not an impurity, the compound in which a and b in general formula (2b') are not the same (i.e., a≠b) is preferably 50 ppm or less in total, more preferably 20 ppm or less in the monomer mainly composed of the compound of general formula (2b').

[0065] The compound of general formula (2b') can be produced by various synthesis methods. For example, as described in Japanese Patent No. 5442800, (a) a method of reacting fluorenones with hydroxynaphthalenes in the presence of hydrogen chloride gas and mercaptocarboxylic acid, (b) a method of reacting 9-fluorenones with hydroxynaphthalenes in the presence of an acid catalyst (and alkyl mercaptan), (c) a method of reacting fluorenones with hydroxynaphthalenes in the presence of hydrochloric acid and thiols (mercaptocarboxylic acid, etc.), (d) a method of reacting fluorenones with hydroxynaphthalenes in the presence of sulfuric acid and thiols (mercaptocarboxylic acid, etc.), and crystallizing the fluorenones with a crystallization solvent composed of a hydrocarbon and a polar solvent to produce bisnaphtholfluorene, etc., to obtain 9,9-bis(hydroxynaphthyl)fluorenes, which can then be reacted with compounds (such as alkylene oxides and haloalkanols) corresponding to the [AO]a group and the [BO]b group. For example, 9,9-bis[6-(2-hydroxyethoxy)naphthyl]fluorene may be obtained by reacting 9,9-bis[6-hydroxynaphthyl]fluorene with 2-chloroethanol under alkaline conditions.

[0066] When producing a polycarbonate resin containing the structural unit (C) used in the present invention, it can be preferably produced by using a compound represented by the following general formula (3a') as a dihydroxy component and reacting it with a carbonate precursor such as a carbonic acid diester. Specifically, it can be produced by reacting the dihydroxy component and a carbonate precursor such as a carbonic acid diester by a melt polycondensation method in the presence of a basic compound catalyst or an ester exchange catalyst or a mixed catalyst consisting of both, or in the absence of a catalyst. [ka] In general formula (3a'), R e , R f , A, B, a and b are each defined as in general formula (3a).

[0067] Examples of dihydroxy compounds represented by general formula (3a') include 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-methylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-tert-butylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-isopropylphenyl]fluorene, 9,9-bis[4-(2-hydroxyethoxy)-3-cyclohexylphenyl]fluorene, and 9,9-bis[4-(2-hydroxyethoxy)-3-phenylphenyl]fluorene (hereinafter sometimes abbreviated as "BPPEF"). Among them, 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene and 9,9-bis[4-(2-hydroxyethoxy)-3-phenylphenyl]fluorene are preferred, and 9,9-bis[4-(2-hydroxyethoxy)-3-phenylphenyl]fluorene (BPPEF) is more preferred. These may be used alone or in combination of two or more.

[0068] The total amount of compounds in which a and b in general formula (3a') are not the same (i.e., a≠b) in the monomer mainly composed of the compound of general formula (3a') is preferably 50 ppm or less, more preferably 20 ppm or less.

[0069] Other examples of aromatic dihydroxy compounds that can be used in combination with the above include bisphenol A, bisphenol AP, bisphenol AF, bisphenol B, bisphenol BP, bisphenol C, bisphenol E, bisphenol F, bisphenol G, bisphenol M, bisphenol S, bisphenol P, bisphenol PH, bisphenol TMC, and bisphenol Z.

[0070] Examples of the carbonic acid diester used in the present invention include diphenyl carbonate, ditolyl carbonate, bis(chlorophenyl) carbonate, m-cresyl carbonate, dimethyl carbonate, diethyl carbonate, dibutyl carbonate, and dicyclohexyl carbonate. Among these, diphenyl carbonate is particularly preferred. Diphenyl carbonate is preferably used in a ratio of 0.97 to 1.20 moles per mole of the total of the dihydroxy compounds, more preferably 0.98 to 1.10 moles, and even more preferably 1.00 to 1.10 moles.

[0071] Among the transesterification catalysts, examples of basic compound catalysts include, in particular, alkali metal compounds, alkaline earth metal compounds, and nitrogen-containing compounds.

[0072] Examples of the alkali metal compound used in the present invention include organic acid salts, inorganic salts, oxides, hydroxides, hydrides, and alkoxides of alkali metals.Specific examples include sodium hydroxide, potassium hydroxide, cesium hydroxide, lithium hydroxide, sodium hydrogencarbonate, sodium carbonate, potassium carbonate, cesium carbonate, lithium carbonate, sodium acetate, potassium acetate, cesium acetate, lithium acetate, sodium stearate, potassium stearate, cesium stearate, lithium stearate, sodium borohydride, sodium phenylborate, sodium benzoate, potassium benzoate, cesium benzoate, lithium benzoate, disodium hydrogen phosphate, dipotassium hydrogen phosphate, dilithium hydrogen phosphate, disodium phenylphosphate, disodium salt, dipotassium salt, dicesium salt, or dilithium salt of bisphenol A, and sodium salt, potassium salt, cesium salt, or lithium salt of phenol.

[0073] Examples of the alkaline earth metal compound include organic acid salts, inorganic salts, oxides, hydroxides, hydrides, and alkoxides of alkaline earth metal compounds.Specific examples include magnesium hydroxide, calcium hydroxide, strontium hydroxide, barium hydroxide, magnesium hydrogen carbonate, calcium hydrogen carbonate, strontium hydrogen carbonate, barium hydrogen carbonate, magnesium carbonate, calcium carbonate, strontium carbonate, barium carbonate, magnesium acetate, calcium acetate, strontium acetate, barium acetate, magnesium stearate, calcium stearate, calcium benzoate, and magnesium phenylphosphate.

[0074] Examples of the nitrogen-containing compound include quaternary ammonium hydroxides and their salts, amines, etc. Specifically, quaternary ammonium hydroxides having an alkyl group, an aryl group, etc., such as tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, and trimethylbenzylammonium hydroxide; tertiary amines such as triethylamine, dimethylbenzylamine, and triphenylamine; secondary amines such as diethylamine and dibutylamine; primary amines such as propylamine and butylamine; imidazoles such as 2-methylimidazole, 2-phenylimidazole, and benzimidazole; or bases or basic salts such as ammonia, tetramethylammonium borohydride, tetrabutylammonium borohydride, tetrabutylammonium tetraphenylborate, and tetraphenylammonium tetraphenylborate, etc., are used.

[0075] As the transesterification catalyst, a salt of zinc, tin, zirconium, lead or the like is preferably used, and these can be used alone or in combination.

[0076] Specific examples of the transesterification catalyst that can be used include zinc acetate, zinc benzoate, zinc 2-ethylhexanoate, tin(II) chloride, tin(IV) chloride, tin(II) acetate, tin(IV) acetate, dibutyltin dilaurate, dibutyltin oxide, dibutyltin dimethoxide, zirconium acetylacetonate, zirconium oxyacetate, zirconium tetrabutoxide, lead(II) acetate, and lead(IV) acetate.

[0077] These catalysts were used in a ratio of 1 × 10 to 1 mole of dihydroxy compounds. -9 ~1×10 -3 In terms of molar ratio, preferably 1 x 10 -7 ~1×10 -4 Used in molar ratios.

[0078] The melt polycondensation method uses the above-mentioned raw materials and catalyst and performs melt polycondensation under heating and at normal or reduced pressure while removing by-products through an ester exchange reaction.

[0079] In the melt polycondensation in this composition system, it is desirable to carry out the reaction in a state where the dihydroxy component and the carbonic acid diester are melted in a reaction vessel and the by-produced monohydroxy compound is retained. In order to retain the monohydroxy compound, the pressure can be controlled by blocking the reaction vessel, reducing pressure, or increasing pressure. The reaction time of this step is 20 minutes or more and 240 minutes or less, preferably 40 minutes or more and 180 minutes or less, and particularly preferably 60 minutes or more and 150 minutes or less. In this case, if the by-produced monohydroxy compound is distilled off immediately after production, the polycarbonate resin finally obtained has a low content of high molecular weight compounds. However, if the by-produced monohydroxy compound is retained in the reaction vessel for a certain period of time, the polycarbonate resin finally obtained has a high content of high molecular weight compounds.

[0080] The melt polycondensation reaction may be carried out continuously or batchwise. The reaction apparatus used for the reaction may be a vertical type equipped with an anchor-type impeller, a Maxblend impeller, a helical ribbon-type impeller, or the like, a horizontal type equipped with a paddle impeller, a lattice impeller, a spectacle impeller, or the like, or an extruder type equipped with a screw. In addition, it is preferable to use a reaction apparatus that is an appropriate combination of these reaction apparatuses, taking into consideration the viscosity of the polymer.

[0081] In the method for producing the polycarbonate resin used in the present invention, the catalyst may be removed or deactivated after the polymerization reaction is completed in order to maintain thermal stability and hydrolytic stability. A method of deactivating the catalyst by adding a known acidic substance can be preferably carried out. Specific examples of the acidic substance include esters such as butyl benzoate, aromatic sulfonic acids such as p-toluenesulfonic acid, aromatic sulfonic acid esters such as butyl p-toluenesulfonate and hexyl p-toluenesulfonate, phosphoric acids such as phosphorous acid, phosphoric acid, and phosphonic acid, phosphoric acid esters such as triphenyl phosphite, monophenyl phosphite, diphenyl phosphite, diethyl phosphite, di-n-propyl phosphite, di-n-butyl phosphite, di-n-hexyl phosphite, dioctyl phosphite, and monooctyl phosphite, and phosphate esters such as triphenyl phosphate, diphenyl phosphate, monophenyl phosphate, dibutyl phosphate, and dioctyl phosphate. Phosphates such as phosphate esters, monooctyl phosphate, etc.; phosphonic acids such as diphenylphosphonic acid, dioctylphosphonic acid, dibutylphosphonic acid, etc.; phosphonic acid esters such as diethyl phenylphosphonate, etc.; phosphines such as triphenylphosphine, bis(diphenylphosphino)ethane, etc.; boric acid, phenylboric acid, etc.; aromatic sulfonates such as tetrabutylphosphonium dodecylbenzenesulfonate, etc.; organic halides such as stearic acid chloride, benzoyl chloride, p-toluenesulfonic acid chloride, etc.; alkyl sulfuric acid such as dimethyl sulfate, etc.; organic halides such as benzyl chloride, etc. are preferably used. These deactivators are used in an amount of 0.01 to 50 times by mol, preferably 0.3 to 20 times by mol, based on the amount of the catalyst. If the amount is less than 0.01 times by mol, the deactivation effect becomes insufficient, which is not preferable. If the amount is more than 50 times by mol, the heat resistance of the resin decreases, and the molded body becomes easily colored, which is not preferable.

[0082] After the catalyst is deactivated, a step may be provided in which low-boiling compounds in the polymer are removed by volatilization at a pressure of 0.1 to 1 mmHg and a temperature of 200 to 350° C. In this step, a horizontal apparatus equipped with stirring blades with excellent surface renewal ability, such as paddle blades, lattice blades, and spectacle blades, or a thin-film evaporator is preferably used.

[0083] The polycarbonate resin used in the present invention is desired to have as little foreign matter content as possible, and filtration of the molten raw material, filtration of the catalyst solution, etc. are preferably carried out. The mesh of the filter is preferably 5 μm or less, more preferably 1 μm or less. Furthermore, filtration of the produced resin with a polymer filter is preferably carried out. The mesh of the polymer filter is preferably 100 μm or less, more preferably 30 μm or less. Furthermore, the process of collecting the resin pellets must be in a low-dust environment, preferably class 6 or less, more preferably class 5 or less.

[0084] After preparing a polycarbonate resin containing the structural unit (B) and / or the structural unit (C), it is preferable to add an additive such as an antioxidant to the polycarbonate resin. The method of addition is not particularly limited and may be performed by any method. For example, the additive may be added to a container containing the polycarbonate resin later, the polycarbonate resin may be added to a container containing the additive in advance, or the polycarbonate resin and the additive may be simultaneously placed in one container. Specifically, the additive may be attached to the pellet-shaped polycarbonate resin using a turnbull mixer, a Henschel mixer, a ribbon blender, a super mixer, a roll mixer, or a tumbler mixer. According to such an addition method, the additive can be uniformly dispersed in the resin composition containing the polycarbonate resin, and the heat history can be reduced, which is preferable. In addition, the pellet-shaped polycarbonate resin may be mixed with pellets obtained by melt-kneading a high concentration of additive into a part of the polycarbonate resin.

[0085] It is preferable to add the additives to the polycarbonate resin and then melt-knead them. The melt-kneading method is not particularly limited, and may be performed by any method. For example, the melt-kneading may be performed by a known kneading method such as a single-screw or twin-screw extruder, a Banbury mixer, or a static mixer. The polycarbonate resin may be pelletized before the additives are added. The pelletizing method is not particularly limited, and any method may be used. In addition, the polycarbonate resin obtained by melt-kneading may be pelletized, and any method may be used for the pelletizing method here.

[0086] [Resin containing structural unit (D)] The resin composition of the present embodiment preferably further contains a resin containing a structural unit (D) represented by the following general formula (4). [ka] In formula (4), R4 represents a hydrogen atom, a methyl group, or an ethyl group, and R5 and R6 each independently represent a hydrogen atom or a methyl group. Preferably, R4, R5, and R6 all represent a hydrogen atom. The resin containing the structural unit (D) is preferably a polyester carbonate resin or a polycarbonate resin, and is particularly preferably a polycarbonate resin. In the resin composition of this embodiment, the mass ratio (A / D) of the structural unit (A) to the structural unit (D) is preferably from 99 / 1 to 1 / 99, more preferably from 90 / 10 to 50 / 50, and particularly preferably from 80 / 20 to 60 / 40.

[0087] The resin composition of this embodiment can be used in combination with resins other than the resin containing the structural unit (A) in this embodiment, the resin containing the structural unit (B) and / or the structural unit (C), and the resin containing the structural unit (D) in this embodiment, within a range that does not impair the desired effects of this embodiment. Such resins are not particularly limited, but examples thereof include polyester resins other than the polyester resin in this embodiment, polycarbonate resins other than the polycarbonate resin in this embodiment, (meth)acrylic resins, polyamide resins, polystyrene resins, cycloolefin resins, acrylonitrile-butadiene-styrene copolymer resins, vinyl chloride resins, polyphenylene ether resins, polysulfone resins, polyacetal resins, and methyl methacrylate-styrene copolymer resins. Various known resins can be used, and one type can be added alone or two or more types can be added in combination to the resin composition.

[0088] To the resin composition of the present embodiment, various additives such as antioxidants, release agents, ultraviolet absorbers, colorants, light stabilizers, lubricants, plasticizers, flow modifiers, thickeners, flame retardants, crystal nucleating agents, compatibilizers, reinforcing agents, extenders, dyes, antistatic agents, antibacterial agents, matting agents, drying regulators, antisettling agents, surfactants, drying oils, waxes, fillers, reinforcing agents, surface smoothing agents, leveling agents, polymerization metal deactivators, and curing reaction accelerators, and molding aids may be added, as long as the desired effects of the present embodiment are not impaired.

[0089] [Antioxidants] The resin composition of the present embodiment preferably contains an antioxidant from the viewpoint of preventing deterioration of the resin during molding and preventing mold fouling to perform stable molding. The amount of the antioxidant contained in the resin composition is preferably 0.001 to 0.50 parts by mass, more preferably 0.01 to 0.40 parts by mass, and particularly preferably 0.05 to 0.30 parts by mass. By making the amount of the antioxidant 0.001 parts by mass or more, the effect of improving thermal stability is achieved, and by making it 0.50 parts by mass or less, the decrease in refractive index and the decrease in Tg due to the amount of the antioxidant being too large can be suppressed.

[0090] As the antioxidant, one type of antioxidant may be used, or multiple types of antioxidants may be used in combination. When multiple types of antioxidants are used, the total amount of the antioxidants may be adjusted so as to be within the above numerical range.

[0091] The antioxidant used in the present invention includes phosphite-based antioxidants, phenol-based antioxidants, sulfur-based antioxidants, epoxy-based antioxidants, and hindered amine-based antioxidants. In particular, phosphite-based antioxidants and phenol-based antioxidants are preferred, and it is more preferred to use a phosphite-based antioxidant and a phenol-based antioxidant in combination. Examples of the phosphite antioxidant include tricresyl phosphite, tris(2-ethylhexyl) phosphite, tridecyl phosphite, trilauryl phosphite, tris(tridecyl) phosphite, and trioleyl phosphite, as well as ADK STAB PEP-8, ADK STAB PEP-36, ADK STAB HP-10, ADK STAB 2112, ADK STAB 2112RG, ADK STAB 1178, ADK STAB 1500, ADK STAB C, ADK STAB 135A, ADK STAB 3010, and ADK STAB TPP manufactured by ADEKA CORPORATION, but are not limited thereto. Note that ADK STAB PEP36 (manufactured by ADEKA CORPORATION), ADK STAB 1500 (manufactured by ADEKA CORPORATION), and ADK STAB 2112 (manufactured by ADEKA CORPORATION) each have the following structure. [ka]

[0092] Preferred examples of the phenol-based antioxidant include compounds represented by the following general formula: [ka] In the above general formula, R p1 and R p2are each independently a hydrocarbon group having 1 to 10 carbon atoms. A is a hydrocarbon group having 1 to 20 carbon atoms which may contain a functional group selected from an ester group, an ether group and an amide group and / or a phosphorus atom. B is a hydrocarbon group having 1 to 6 carbon atoms which may contain an oxygen atom and / or a nitrogen atom, a sulfur atom or a single bond. g is an integer of 1 to 4. Specific examples include 1,6-hexanediol-bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], 2,2-thio-diethylenebis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], tris(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurate, and N,N'-hexamethylenebis(3,5-di-tert-butyl-4-hydroxy-hydrocinnamide), as well as ADEGASTAB AO-20, ADEGASTAB AO-30, ADEGASTAB AO-50, ADEGASTAB AO-50F, ADEGASTAB AO-60, ADEGASTAB ASO-60GAO-80G, and ADEGASTAB AO-330 manufactured by ADEKA CORPORATION, but are not limited thereto. It should be noted that ADK STAB AO60 (manufactured by ADEKA CORPORATION), ADK STAB AO80 (manufactured by ADEKA CORPORATION), and ADK STAB AO50 (manufactured by ADEKA CORPORATION) each have the following structure. [ka]

[0093] [Release agent] The resin composition of the present embodiment preferably contains a release agent from the viewpoint of reducing friction between the resin composition and a molding machine during molding, thereby preventing a decrease in the molecular weight of the resin and coloring. The amount of the release agent contained in the resin composition is preferably 0.001 to 0.50% by mass, more preferably 0.01 to 0.40% by mass, and particularly preferably 0.05 to 0.30% by mass.

[0094] The release agent is preferably one that is composed of 90% by mass or more of an ester of alcohol and fatty acid. Specific examples of the ester of alcohol and fatty acid include ester of monohydric alcohol and fatty acid, and partial or full ester of polyhydric alcohol and fatty acid. The ester of monohydric alcohol and fatty acid is preferably an ester of monohydric alcohol having 1 to 20 carbon atoms and saturated fatty acid having 10 to 30 carbon atoms. In addition, the partial or full ester of polyhydric alcohol and fatty acid is preferably a partial or full ester of polyhydric alcohol having 1 to 25 carbon atoms and saturated fatty acid having 10 to 30 carbon atoms.

[0095] Specifically, examples of esters of monohydric alcohols and saturated fatty acids include stearyl stearate, palmityl palmitate, butyl stearate, methyl laurate, isopropyl palmitate, etc. Examples of partial or complete esters of polyhydric alcohols and saturated fatty acids include complete or partial esters of dipentaerythritol, such as stearic acid monoglyceride, stearic acid monoglyceride, stearic acid diglyceride, stearic acid triglyceride, stearic acid monosorbitate, behenic acid monoglyceride, capric acid monoglyceride, lauric acid monoglyceride, pentaerythritol monostearate, pentaerythritol tetrastearate, pentaerythritol tetrapelargonate, propylene glycol monostearate, biphenyl biphenate, sorbitan monostearate, 2-ethylhexyl stearate, and dipentaerythritol hexastearate. Of these esters, stearyl stearate, stearate monoglyceride, stearate diglyceride or stearate triglyceride is preferred.

[0096] [Optical lenses] The optical lens manufactured using the resin composition of the present invention has a high refractive index, a low Abbe number, and high thermal stability, and is therefore very useful in fields where expensive high refractive index glass lenses have been used in the past, such as telescopes, binoculars, and television projectors. It is preferable to use it in the form of an aspherical lens as necessary. Since an aspherical lens can substantially reduce spherical aberration to zero with a single lens, it is not necessary to remove spherical aberration by combining multiple spherical lenses, and it is possible to reduce weight and production costs. Therefore, the aspherical lens is particularly useful as a camera lens among optical lenses. The optical lens is molded by any method, such as injection molding, compression molding, injection compression molding, etc. According to the present invention, it is possible to more easily obtain a high refractive index, low birefringence aspheric lens, which is technically difficult to process using glass lenses.

[0097] In order to prevent foreign matter from getting into the optical lens as much as possible, the molding environment must naturally be a low-dust environment, preferably class 6 or less, and more preferably class 5 or less.

[0098] [Optical film] The optical film produced by using the resin composition of the present invention has excellent transparency and thermal stability, and is therefore suitable for use as a film for liquid crystal substrates, optical memory cards, and the like.

[0099] Examples of molding methods include, in addition to injection molding, compression molding, casting, rolling, extrusion molding, and stretching, but are not limited to these.

[0100] When the polycarbonate resin of the present invention is used for injection molding, the glass transition temperature (Tg) is preferably 90 to 180°C, more preferably 95 to 175°C, even more preferably 100 to 170°C, even more preferably 130 to 170°C, and particularly preferably 135 to 150°C. If Tg is lower than 90°C, the use temperature range becomes narrow, which is not preferable. If it exceeds 180°C, the melting temperature of the resin becomes high, which is not preferable because decomposition or coloring of the resin is likely to occur. If the glass transition temperature of the resin is too high, the difference between the mold temperature and the resin glass transition temperature becomes large in a general-purpose mold temperature regulator. Therefore, in applications where strict surface accuracy is required for the product, it is difficult and not preferable to use a resin with a too high glass transition temperature. In addition, from the viewpoint of molding flowability and molding heat resistance, the lower limit of Tg is preferably 130°C, more preferably 135°C, and the upper limit of Tg is preferably 160°C, more preferably 150°C.

[0101] In order to prevent foreign matter from being mixed into the optical film as much as possible, the molding environment must naturally be a low-dust environment, preferably class 6 or less, and more preferably class 5 or less. EXAMPLES

[0102] The present invention will be described below with reference to examples, but the present invention is not limited to these examples. The values ​​in the examples were measured using the following methods or devices.

[0103] <Evaluation methods for polyester resins, polycarbonate resins, and resin compositions> (1) Copolymer composition of polyester resin 1 H-NMR and 13 C-NMR was measured, and the copolymer composition of the polyester resin was calculated from the peak area ratio derived from each structural unit. A nuclear magnetic resonance device (manufactured by Bruker Biospin, product name: AVANCE III 500 / Ascend 500) was used as the measurement device, and measurements were performed at 500 MHz. Deuterated chloroform was used as the solvent.

[0104] (2) Weight average molecular weight (Mw) The weight average molecular weight of the resin and the resin composition was measured by gel permeation chromatography (GPC) and calculated in terms of standard polystyrene. The apparatus, column, and measurement conditions used are as follows: GPC equipment: Tosoh Corporation, HLC-8420GPC Column: Tosoh Corporation, TSKgel SuperHM-M x 3 1 x TSKgel guardcolumn SuperH-H, manufactured by Tosoh Corporation Tosoh Corporation, TSKgel SuperH-RC x 1 Detector: RI detector Standard polystyrene: Standard polystyrene kit PStQuick C manufactured by Tosoh Corporation Sample solution: 0.2% by mass tetrahydrofuran solution Eluent: Tetrahydrofuran ·Eluent flow rate: 0.6mL / min Column temperature: 40℃

[0105] (3) Glass transition temperature (Tg) The glass transition temperature of the resin and the resin composition was measured using a differential scanning calorimeter (manufactured by Shimadzu Corporation, product name: DSC-60 / TA-60WS). 5 to 10 mg of the sample was placed in an aluminum non-sealed container, heated to 280°C at a heating rate of 10°C / min in a nitrogen gas (50 mL / min) flow, and then rapidly cooled. This was heated again under the same conditions, and the temperature at which the DSC curve changed by 1 / 2 the difference in the baseline before and after the transition (midpoint glass transition temperature) was taken as the glass transition temperature.

[0106] (4) Refractive index (nd) and Abbe number (νd) The refractive index and Abbe number of the resin and resin composition were measured by cutting a disk-shaped body having a diameter of 44 mmφ and a thickness of 3 mm, which was prepared by the method described below, at a right angle from the center to prepare a measurement sample, which was then annealed in a dryer at 100°C for 12 hours and then measured using a precision refractometer (KPR-200, manufactured by Kalnew Optical Co., Ltd.). The refractive index was measured at a temperature of 23°C for wavelengths of 486.1 nm (F line), 587.6 nm (d line), and 656.3 nm (C line). The Abbe number was calculated from the refractive index at each wavelength using the following formula (1). Equation (1) νd=(nd-1) / (nF-nC) (In formula (1), νd is the Abbe number, nF is the refractive index at a wavelength of 486.1 nm, nd is the refractive index at a wavelength of 587.6 nm, and nC is the refractive index at a wavelength of 656.3 nm).

[0107] (5) Fabrication of a disk-shaped body (diameter 44 mmφ, thickness 3 mm) Using an injection molding machine (manufactured by The Japan Steel Works, Ltd., J55AD), injection molding was carried out under conditions of a cylinder temperature of 260 to 270° C. and a mold temperature of 110 to 120° C. to produce a disk-shaped product of the resin composition.

[0108] (6) Continuous moldability Using an injection molding machine (FANUC Corporation, ROBOSHOT α-S30iA) and a mold for forming eight aspheric lenses with an outer diameter of 4.7 mm and a center thickness of 0.26 mm, continuous injection molding was performed under the conditions of a cylinder temperature of 290°C, a mold temperature of Tg-10°C, and a molding cycle time of 25 to 40 sec / shot. If any damage occurred to the lens part, sprue, or runner during molding, the continuous molding was stopped at that point, and the continuous moldability was evaluated according to the following criteria. A: Continuous molding is possible for 30 shots or more. B: Continuous molding is possible for less than 30 shots, and the degree of damage is small when visually inspected. B': Continuous molding is possible for less than 30 shots, and the degree of damage is large when visually observed.

[0109] <Synthesis of polyester resin> <Synthesis Examples 1 to 4> A 30L reactor equipped with a stirrer, a heater, a nitrogen inlet tube, a partial condenser, a total condenser, a cold trap, and a vacuum pump was charged with the raw material monomers and manganese(II) acetate tetrahydrate in the amounts shown in Table 1 below, and the temperature was raised to 235-245°C under a nitrogen atmosphere, and the mixture was stirred to carry out an ester exchange reaction. After the reaction conversion rate of the hydroxycarboxylic acid ester component and the diester component calculated from the amount of methanol distilled from the reactor reached 90% or more, germanium(IV) oxide and phosphoric acid in the amounts shown in Table 1 below were added, and the temperature and pressure were gradually raised and reduced, and a polycondensation reaction was carried out at 270-280°C and 133 Pa or less. After it was confirmed that the reaction liquid had an appropriate melt viscosity, the stirring was stopped, nitrogen was blown into the reactor to pressurize it to 0.3 MPa, and the produced polyester resin was recovered while being pelletized. The evaluation results of the obtained polyester resin are shown in Table 1 below.

[0110] [Table 1]

[0111] D-NHEs: Decahydro-1,4:5,8-dimethanonaphthalene-2-methoxycarbonyl-6(7)-methanol [ka]

[0112] DMCD: 1,4-Dimethylcyclohexanedicarboxylate (cis / trans=7 / 3) [ka]

[0113] FDPM: 9,9-bis(2-methoxycarbonylethyl)fluorene (dimethyl fluorene dipropionate) [ka]

[0114] BPEF: 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (bisphenoxyethanolfluorene) [ka]

[0115] EG: Ethylene glycol [ka]

[0116] <Synthesis of polycarbonate resin> <Synthesis Example 5> 20.00 kg (45.61 mol) of 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene (BPEF), 10.16 kg (47.43 mol) of diphenyl carbonate (DPC), and 30.00 mg (3.6 × 10 -4 (mol) was placed in a 50L reactor equipped with a stirrer and a distillation device, heated to 205 ° C. over 60 minutes under a nitrogen atmosphere of 760 Torr, and stirred. Subsequently, the pressure was reduced to 200 Torr over 20 minutes, and the mixture was held under the conditions of 205 ° C. and 200 Torr for 30 minutes. After that, the temperature was raised and the pressure was reduced to 215 ° C. and 180 Torr over 20 minutes, then to 230 ° C. and 150 Torr over 50 minutes, and then to 240 ° C. and 1 Torr or less over 60 minutes, and finally held for 20 minutes under the conditions of 240 ° C. and 1 Torr or less. After confirming that the reaction liquid had an appropriate melt viscosity, the stirring was stopped, nitrogen was blown into the reactor to apply pressure, and the produced polycarbonate resin was recovered while being pelletized. The polycarbonate resin thus obtained had a polystyrene-equivalent weight average molecular weight (Mw) of 23,000 and a glass transition temperature (Tg) of 145°C.

[0117] BPEF: 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene (bisphenoxyethanolfluorene) [ka]

[0118] <Synthesis Example 6> 23.50 kg (105.70 mol) of decahydro-1,4:5,8-dimethanonaphthalene-2,6(7)-dimethanol (also referred to as "D-NDM") represented by the following structural formula (a), 22.98 kg (107.27 mol) of diphenyl carbonate (also referred to as "DPC"), and 130.00 mg (1.5×10 -3 mol) was placed in a 50L reactor equipped with a stirrer and a distillation device, heated to 205 ° C. over 60 minutes under a nitrogen atmosphere of 760 Torr, and stirred. Subsequently, the pressure was reduced to 200 Torr over 30 minutes, and the mixture was held under the conditions of 205 ° C. and 200 Torr for 30 minutes. After that, the temperature was raised and the pressure was reduced to 215 ° C. and 180 Torr over 20 minutes, then to 230 ° C. and 150 Torr over 40 minutes, and then to 240 ° C. and 1 Torr or less over 60 minutes, and finally held for 20 minutes under the conditions of 240 ° C. and 1 Torr or less. After confirming that the reaction liquid had an appropriate melt viscosity, the stirring was stopped, nitrogen was blown into the reactor to apply pressure, and the produced polycarbonate resin was recovered while being pelletized. The polycarbonate resin thus obtained had a polystyrene-equivalent weight average molecular weight (Mw) of 27,000 and a glass transition temperature (Tg) of 132°C.

[0119] D-NDM: Decahydro-1,4:5,8-dimethanonaphthalene-2,6(7)-dimethanol [ka]

[0120] <Method of producing resin composition> <Examples 1 to 8 and Comparative Examples 1 to 4> The polyester resins obtained in Synthesis Examples 1 to 4, the polycarbonate resins obtained in Synthesis Examples 5 or 6, the antioxidants, and the release agents were dry-mixed using a tumbler in the ratios (units: parts by mass) shown in Table 2 below. The mixture was melt-kneaded using a twin-screw extruder (IPEC Corporation, IPT-type 35 mm co-rotating twin-screw extruder) at a cylinder temperature of 260°C and a vent pressure of 25 Torr, extruded as strands, and then pelletized to obtain pellets of a transparent resin composition. The evaluation results of the obtained resin compositions are shown in Table 2 below.

[0121] [Table 2]

[0122] The meanings of the abbreviations in the table are as follows: AO-60: ADEKA STAB AO-60, manufactured by ADEKA Corporation PEP-36: ADEKA STAB PEP-36, manufactured by ADEKA Corporation NAA-180: NOF Corporation, NAA-180 M-2222SL: NOF Corp., Unistar M-2222SL

[0123] In Examples 1 and 2, the Abbe number could be reduced while maintaining the refractive index at approximately the same level as in Comparative Example 1, which used the same polyester resin, and a high Tg (improved heat resistance) was achieved. In Examples 5 to 7, the refractive index tended to be slightly higher than in Comparative Example 3, but a resin composition with a reduced Abbe number could be obtained. In Example 8, the Abbe number could be reduced slightly compared to Comparative Example 4, and continuous moldability could also be improved.

Claims

1. A resin including a structural unit (A) represented by the following general formula (1), A resin composition comprising a resin containing a structural unit (B) represented by the following general formula (2) and / or a structural unit (C) represented by the following general formula (3): 【Chemistry 1】 (In general formula (1), R １ represents a hydrogen atom, a methyl group, or an ethyl group; R ２ and R ３ each independently represents a hydrogen atom or a methyl group, and n represents 0 or 1. 【Chemistry 2】 (In general formula (2), R ａ and R ｂ each independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxyl group having 1 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, a cycloalkoxyl group having 5 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 6 to 20 carbon atoms containing one or more hetero ring atoms selected from O, N, and S, or an aryloxy group having 6 to 20 carbon atoms, and -C≡C-R ｈ is selected from the group consisting of R ｈ represents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 6 to 20 carbon atoms containing one or more hetero ring atoms selected from O, N, and S; X represents a fluorene group; A and B each independently represent an alkylene group having 1 to 4 carbon atoms; m and n each independently represent an integer of 0 to 6; a and b each independently represent an integer of 0 to 10. 【Chemistry 3】 (In general formula (3), R ｃ and R ｄ are each independently selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxyl group having 1 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, a cycloalkoxyl group having 5 to 20 carbon atoms, and an aryl group having 6 to 20 carbon atoms; Y represents a fluorene group; A and B each independently represent an alkylene group having 1 to 4 carbon atoms; p and q each independently represent an integer of 0 to 4; a and b each independently represent an integer of 0 to 10.

2. The resin containing the structural unit (A) represented by the general formula (1) is a polyester resin, and the resin containing the structural unit (B) represented by the general formula (2) and / or the structural unit (C) represented by the general formula (3) is a polycarbonate resin. The resin composition according to claim 1.

3. The resin composition according to claim 1 or 2, further comprising a resin containing a structural unit (D) represented by the following general formula (4): 【Chemistry 4】 (In general formula (4), R ４ represents a hydrogen atom, a methyl group, or an ethyl group; R ５ and R ６ each independently represents a hydrogen atom or a methyl group.

4. The resin composition according to claim 3, wherein the resin containing the structural unit (D) represented by the general formula (4) is a polycarbonate resin.

5. The resin composition according to any one of claims 1 to 4, wherein the structural unit (B) represented by the general formula (2) includes a structural unit represented by the following general formula (2b): 【Chemistry 5】 In the general formula (2b), A, B, a, and b are the same as those in the general formula (2). ｅ and R ｆ are each independently selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxyl group having 1 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, a cycloalkoxyl group having 5 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, and an aryloxy group having 6 to 20 carbon atoms.

6. R in the general formula (2) ａ and R ｂ The resin composition according to claim 1 , wherein each independently represents a hydrogen atom, a phenyl group, a naphthyl group, or a substituent selected from the group consisting of the following: 【Chemistry 6】

7. The resin composition according to claim 1 , wherein the structural unit (C) represented by the general formula (3) includes a structural unit represented by the following general formula (3a): 【Chemistry 7】 (In the general formula (3a), A, B, a, and b are the same as those in the general formula (3). R ｅ and R ｆ are each independently selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxyl group having 1 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, a cycloalkoxyl group having 5 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, and an aryloxy group having 6 to 20 carbon atoms.

8. The resin composition according to any one of claims 1 to 7, wherein the mass ratio (A / B) of the structural unit (A) to the structural unit (B) is 99 / 1 to 1 / 99.

9. The resin composition according to any one of claims 1 to 8, wherein the mass ratio (A / C) of the structural unit (A) to the structural unit (C) is 99 / 1 to 1 / 99.

10. The resin composition according to claim 3 or 4, wherein the mass ratio (A / D) of the structural unit (A) to the structural unit (D) is 99 / 1 to 1 / 99.

11. The resin composition according to claim 1 , further comprising an antioxidant.

12. The resin composition according to claim 11, wherein the antioxidant is a phosphite-based antioxidant and / or a phenol-based antioxidant.

13. R in the general formula (1) １ , R ２ and R ３ The resin composition according to claim 1 , wherein: represents a hydrogen atom; and n represents 1.

14. A molded article comprising the resin composition according to any one of claims 1 to 13.

15. The molded article according to claim 14, wherein the molded article is an optical lens.

16. The molded article according to claim 14, wherein the molded article is an optical film.

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