Resin composition

Abstract

Provided is a resin composition that is highly fluid and has good moldability, and that has excellent optical properties. More specifically, provided is a resin composition that contains a thermoplastic resin and a specific compounding agent containing a naphthalene structure and / or a fluorene structure.

Description

[Technical Field]

[0001] The present invention relates to a resin composition. More specifically, the present invention relates to a resin composition containing a thermoplastic resin and specific compounding agents. [Background technology]

[0002] Optical glass or optical resin is used as a material for optical lenses used in the optical systems of various cameras, such as cameras with integrated film, video cameras, etc. Optical glass is excellent in heat resistance, transparency, dimensional stability, chemical resistance, etc., but has problems such as high material costs, poor moldability, and low productivity.

[0003] On the other hand, optical lenses made of optical resins have the advantage that they can be mass-produced by injection molding, and polycarbonate, polyester carbonate, polyester resin, etc. are used as high refractive index materials for camera lenses.

[0004] When an optical resin is used as an optical lens, in addition to optical properties such as refractive index and Abbe number, it is required to have heat resistance, transparency, low water absorption, chemical resistance, low birefringence, moist heat resistance, etc. In particular, in recent years, there has been a demand for optical lenses with high refractive index and high heat resistance, and various resins have been developed (Patent Documents 1 to 5).

[0005] However, there is still a demand for a thermoplastic resin composition that has high flowability, good moldability, and excellent optical properties without impairing the properties required for an optical resin composition. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] Japanese Patent Application Publication No. 2018-2893 [Patent Document 2] Japanese Patent Application Laid-Open No. 2018-2894 [Patent Document 3] Japanese Patent Application Publication No. 2018-2895 [Patent Document 4] Japanese Patent Application Publication No. 2018-59074 [Patent Document 5] WO 2017 / 078073 Summary of the Invention [Problem to be solved by the invention]

[0007] The present invention provides a thermoplastic resin composition that has high flowability and good moldability without impairing the properties of optical resin compositions, and that has excellent optical properties. [Means for solving the problem]

[0008] As a result of extensive research aimed at solving the problems of the past, the present inventors have discovered that by adding specific compounding agents to a thermoplastic resin, it is possible to obtain a thermoplastic resin composition having a low Tg, high flowability, good moldability, and excellent optical properties, and have completed the present invention.

[0009] That is, the present invention includes the following aspects. <1> A thermoplastic resin; a compounding agent having a naphthalene structure and / or a fluorene structure; A resin composition comprising: The resin composition, wherein the compounding agent having a naphthalene structure and / or a fluorene structure comprises one or more compounds selected from compounds containing a structural unit represented by any one of the following general formulas (1) to (3): [ka] (In formula (1), R a and R b each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms which may contain a heterocyclic atom selected from O, N, and S, an alkenyl group having 2 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms; X represents a saturated carbon group having 1 to 5 carbon atoms; a and b each independently represent an integer of 0 to 10. [ka] (In formula (2), R c and R d are each independently 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≡CR h is selected from R h represents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 6 to 20 carbon atoms and containing one or more hetero ring atoms selected from O, N, and S, X represents a saturated carbon group having 1 to 5 carbon atoms; c and d each independently represent an integer of 0 to 10. [ka] (In formula (3), R e and R f each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms which may contain a heterocyclic atom selected from O, N, and S, an alkenyl group having 2 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms; X represents a saturated carbon group having 1 to 5 carbon atoms; e and f each independently represent an integer of 0 to 10. <2> The compounding agent having a naphthalene structure and / or a fluorene structure is at least one selected from the group consisting of a diol monomer having a structural unit represented by any one of general formulas (1) to (3) and a polycarbonate oligomer containing a structural unit represented by any one of general formulas (1) to (3) as a diol structure. <1> The resin composition according to claim 1. <3> The polycarbonate oligomer containing a constitutional unit represented by any one of the general formulas (1) to (3) as a diol structure is represented by any one of the following formulas, wherein R a , R b , R c , R d , R e , R f , a, b, c, d, e, and f are respectively <1> As described in <2> The resin composition according to claim 1. [ka] <4> The 5% thermal mass loss starting temperature (5% thermal mass loss temperature) of the compounding agent is 260°C or higher. <1> ~ <3> The resin composition according to any one of the preceding claims. <5> The weight average molecular weight of the compounding agent is less than 10,000. <1> ~ <4> The resin composition according to any one of the preceding claims. <6> The mass ratio of the thermoplastic resin to the compounding agent is thermoplastic resin: compounding agent=99:1 to 70:30. <1> ~ <5> The resin composition according to any one of the preceding claims. <7> The polystyrene-equivalent molecular weight (Mw) of the thermoplastic resin is 10,000 to 100,000. <1> ~ <6> The resin composition according to any one of the preceding claims. <8> The thermoplastic resin is selected from the group consisting of polycarbonate resin, polyester resin, and polyester carbonate resin. <1> ~ <7> The resin composition according to any one of the preceding claims. <9> The thermoplastic resin contains a structural unit derived from a compound represented by the following general formula (a): <1> ~ <8> The resin composition according to any one of the preceding claims. [ka] (In formula (a), R c and R d are each independently 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≡CR h is selected from R h represents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 6 to 20 carbon atoms and containing one or more hetero ring atoms selected from O, N, and S, X represents a saturated carbon group having 1 to 5 carbon atoms; c and d each independently represent an integer of 0 to 10. <10> <1> ~ <9> An optical member comprising the resin composition according to any one of the above items. <11> <1> ~ <9> An optical lens comprising the resin composition according to any one of the above items. <12> <1> ~ <9> An optical film comprising the resin composition according to any one of the above items. [Effects of the Invention]

[0010] The present invention can provide a thermoplastic resin composition that has high flowability and good moldability without impairing the properties of an optical resin composition, and that has excellent optical properties. DETAILED DESCRIPTION OF THE INVENTION

[0011] 1.Resin composition The resin composition of the present invention contains a thermoplastic resin and a specific compounding agent having a naphthalene structure and / or a fluorene structure. By compounding the specific compounding agent having a naphthalene structure and / or a fluorene structure with a thermoplastic resin, a thermoplastic resin composition with high flowability, good moldability, and excellent optical properties can be obtained without impairing the properties of the optical resin composition.

[0012] 1-1. Combination Agents In the resin composition of the present invention, the compounding agent having a naphthalene structure and / or a fluorene structure contains one or more compounds selected from compounds containing a structural unit represented by any one of the following general formulas (1) to (3): The compounds containing a structural unit represented by any one of the following general formulas (1) to (3) may be used singly or in combination of two or more. [ka] (In formula (1), R a and R b each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms which may contain a heterocyclic atom selected from O, N, and S, an alkenyl group having 2 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms; X represents a saturated carbon group having 1 to 5 carbon atoms; a and b each independently represent an integer of 0 to 10. [ka] (In formula (2), R c and R dare each independently 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≡CR h is selected from R h represents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 6 to 20 carbon atoms and containing one or more hetero ring atoms selected from O, N, and S, X represents a saturated carbon group having 1 to 5 carbon atoms; c and d each independently represent an integer of 0 to 10. [ka] (In formula (3), R e and R f each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms which may contain a heterocyclic atom selected from O, N, and S, an alkenyl group having 2 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms; X represents a saturated carbon group having 1 to 5 carbon atoms; e and f each independently represent an integer of 0 to 10.

[0013] Building blocks of compounded drugs <Constituent unit represented by formula (1)> In one embodiment of the present invention, the compounding agent having a naphthalene structure and / or a fluorene structure may be a compound containing a constitutional unit represented by the following general formula (1). [ka] (In formula (1), R a and Rb each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms which may contain a heterocyclic atom selected from O, N, and S, an alkenyl group having 2 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms; X represents a saturated carbon group having 1 to 5 carbon atoms; a and b each independently represent an integer of 0 to 10.

[0014] In a preferred embodiment of the present invention, in formula (1), R a and R b each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms which may contain a heterocyclic atom selected from O, N, and S, an alkenyl group having 2 to 15 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, or an aralkyl group having 7 to 17 carbon atoms.

[0015] In formula (1), the alkyl group may more preferably be an alkyl group having 1 to 6 carbon atoms, and even more preferably methyl.

[0016] In formula (1), the aryl group may be an aryl group having more preferably 6 to 16 carbon atoms, even more preferably 6 to 14 carbon atoms, even more preferably 6 to 12 carbon atoms, and even more preferably 6 to 10 carbon atoms.

[0017] In formula (1), the alkenyl group may more preferably be an alkenyl group having 2 to 10 carbon atoms.

[0018] In the formula (1), the alkoxy group may more preferably be an alkoxy group having 1 to 3 carbon atoms.

[0019] In formula (1), the aralkyl group may more preferably be an aralkyl group having 7 to 10 carbon atoms.

[0020] In formula (1), X may more preferably be an alkylene group having 1 to 4 carbon atoms, even more preferably an alkylene group having 1 to 3 carbon atoms, and even more preferably an alkylene group having 2 carbon atoms.

[0021] In formula (1), a and b may each independently be an integer of 0 to 5, more preferably an integer of 1 to 5, even more preferably an integer of 1 to 3, and even more preferably 1.

[0022] <Constituent unit represented by formula (2)> In one embodiment of the present invention, the compounding agent having a naphthalene structure and / or a fluorene structure may be a compound containing a constitutional unit represented by the following general formula (2). [ka] (In formula (2), R c and R d are each independently 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≡CR h is selected from R h represents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 6 to 20 carbon atoms and containing one or more hetero ring atoms selected from O, N, and S, X represents a saturated carbon group having 1 to 5 carbon atoms; c and d each independently represent an integer of 0 to 10.

[0023] In a preferred embodiment of the present invention, in formula (2), R c and R deach independently represents 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 Selected from R h represents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 6 to 20 carbon atoms and containing one or more hetero ring atoms selected from O, N and S.

[0024] In formula (2), the aryl group more preferably has 6 to 18 carbon atoms, more preferably has 6 to 16 carbon atoms, more preferably has 6 to 14 carbon atoms, more preferably has 6 to 12 carbon atoms, and even more preferably has 6 to 10 carbon atoms.

[0025] In formula (2), the heteroaryl group more preferably has 6 to 18 carbon atoms, more preferably has 8 to 16 carbon atoms, and even more preferably has 10 to 14 carbon atoms.

[0026] In formula (2), the aryloxy group more preferably has 6 to 18 carbon atoms, more preferably has 6 to 16 carbon atoms, and even more preferably has 6 to 14 carbon atoms.

[0027] In formula (2), X may more preferably be an alkylene group having 1 to 4 carbon atoms, even more preferably an alkylene group having 1 to 3 carbon atoms, and even more preferably an alkylene group having 2 carbon atoms.

[0028] In formula (2), c and d may each independently be an integer of 0 to 5, more preferably an integer of 1 to 5, even more preferably an integer of 1 to 3, and even more preferably 1.

[0029] In a preferred embodiment of the present invention, in formula (2), R c and R d may each independently be selected from the group consisting of a phenyl group, a naphthyl group, or [ka] X represents an alkylene group having 1 to 4 carbon atoms, more preferably an alkylene group having 1 to 3 carbon atoms, and even more preferably an alkylene group having 2 carbon atoms; c and d each independently represent an integer of 0 to 5, more preferably an integer of 1 to 5, even more preferably an integer of 1 to 3, and even more preferably 1.

[0030] <Constituent unit represented by formula (3)> In one embodiment of the present invention, the compounding agent having a naphthalene structure and / or a fluorene structure may be a compound containing a constitutional unit represented by the following general formula (3). [ka] (In formula (3), R e and R f each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms which may contain a heterocyclic atom selected from O, N, and S, an alkenyl group having 2 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms; X represents a saturated carbon group having 1 to 5 carbon atoms; e and f each independently represent an integer of 0 to 10.

[0031] In a preferred embodiment of the present invention, in formula (3), R e and R f each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms which may contain a heterocyclic atom selected from O, N, and S, an alkenyl group having 2 to 15 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, or an aralkyl group having 7 to 17 carbon atoms.

[0032] In formula (3), the alkyl group may more preferably be an alkyl group having 1 to 6 carbon atoms, and even more preferably methyl.

[0033] In formula (3), the aryl group may be an aryl group having more preferably 6 to 16 carbon atoms, even more preferably 6 to 14 carbon atoms, even more preferably 6 to 12 carbon atoms, and even more preferably 6 to 10 carbon atoms.

[0034] In the formula (3), the alkenyl group may more preferably be an alkenyl group having 2 to 10 carbon atoms.

[0035] In the formula (3), the alkoxy group may more preferably be an alkoxy group having 1 to 3 carbon atoms.

[0036] In the formula (3), the aralkyl group may more preferably be an aralkyl group having 7 to 10 carbon atoms.

[0037] In formula (3), X may more preferably be an alkylene group having 1 to 4 carbon atoms, even more preferably an alkylene group having 1 to 3 carbon atoms, and even more preferably an alkylene group having 2 carbon atoms.

[0038] In formula (3), e and f may each independently be an integer of 0 to 5, more preferably an integer of 1 to 5, even more preferably an integer of 1 to 3, and even more preferably 1.

[0039] Form of compounding agent In one embodiment of the present invention, the compounding agent having a naphthalene structure and / or a fluorene structure may be one or more compounds selected from the group consisting of diol monomers having a structural unit represented by any one of general formulas (1) to (3) and polycarbonate oligomers containing a structural unit represented by any one of general formulas (1) to (3) as a diol structure. The compound containing a structural unit represented by any one of general formulas (1) to (3) may be used alone or in combination of two or more compounds.

[0040] <Diol Monomer> In one embodiment of the present invention, the compounding agent having a naphthalene structure and / or a fluorene structure may be a diol monomer having a structural unit represented by any one of general formulas (1) to (3), and the diol monomer may be used alone or in combination of two or more.

[0041] <Polycarbonate oligomer> In one embodiment of the present invention, the compounding agent having a naphthalene structure and / or a fluorene structure may be a polycarbonate oligomer containing a structural unit represented by any one of general formulas (1) to (3) as a diol structure, and the polycarbonate oligomer may be used alone or in combination of two or more.

[0042] In a preferred embodiment of the present invention, the polycarbonate oligomer containing a constitutional unit represented by any one of general formulas (1) to (3) as a diol structure may be represented by any one of the following formulas: a , R b , R c , R d , R e , R f , a, b, c, d, e, and f are respectively <1> As described in. [ka]

[0043] In one embodiment of the present invention, the polycarbonate oligomer may have 1 to 6 repeating units, preferably 1 to 3 repeating units, and more preferably 3 repeating units.

[0044] Manufacturing method for polycarbonate oligomer compounding agent Polycarbonate oligomers are obtained by a transesterification method, for example, by mixing a diol with an excess amount of bisaryl carbonate and reacting them at high temperature under reduced pressure in the presence of a transesterification catalyst. The molar ratio of diol to bisaryl carbonate is preferably diol:bisaryl carbonate = 1:1.3 to 10, more preferably 1:1.5 to 5. Polycarbonate oligomers do not have a uniform number of repeating units, but are an aggregate of molecular chains with different numbers of repeating units, and are a mixture that may also contain unreacted bisaryl carbonate and diol.

[0045] Physical properties of compounding agents (1) 5% thermal mass reduction start temperature (5% thermal mass reduction temperature) In one embodiment of the present invention, the above-mentioned compounding agent may have a 5% thermal mass loss onset temperature (5% thermal mass loss temperature) of 260°C or higher, preferably 280°C or higher, and more preferably 300°C or higher. The 5% thermal mass loss onset temperature (5% thermal mass loss temperature) refers to the temperature at which the weight of the substance decreases by 5% when measured using a thermogravimetry / differential thermal analyzer (TG / TDA). In the present invention, if the 5% thermal mass loss onset temperature (5% thermal mass loss temperature) of the compounding agent is within the above range, it has sufficient heat resistance.

[0046] (2) Mass average molecular weight In one embodiment of the present invention, when the compounding agent is an oligomer, its weight average molecular weight may be less than 10,000, preferably 5,000 or less, and more preferably 3,000 or less. In the present invention, if the weight average molecular weight of the compounding agent is within the above range, a resin with high fluidity can be obtained. The weight average molecular weight of the compounding agent can be measured by a conventional method, for example, by measuring it by gel permeation chromatography (GPC) and calculating it in terms of standard polystyrene, or, when the compounding agent is an oligomer, 1 H-NMR and 13 It can be obtained by calculating the number of repeating units from the integral ratio of protons and carbons derived from the main skeleton and the integral ratio of protons and carbons derived from the terminal phenyl groups in C-NMR.

[0047] (3) Mass ratio of thermoplastic resin to compounding agent In one embodiment of the present invention, the above-mentioned compounding agents can be compounded so that the mass ratio of the thermoplastic resin to the compounding agents (polycarbonate thermoplastic resin: compounding agents) is 99.9:0.1 to 70:30. The mass ratio may be preferably 99:1 to 70:30, more preferably 98:2 to 70:30, and may be, for example, 99:1, 98:2, 97:3, 96:4, 95:5, 94:6, 93:7, 92:8, 91:9, 90:10, 85:15, 80:20, 75:25, 70:30, etc. In the present invention, when the mass ratio of the thermoplastic resin to the compounding agents is within the above range, a resin composition with high flowability and good moldability can be provided.

[0048] 1-2.Thermoplastic resin Thermoplastic resins that can be used in the resin composition of the present invention include, but are not limited to, polycarbonate resins, polyester resins, polyester carbonate resins, etc. In one embodiment of the present invention, the thermoplastic resin can be selected from the group consisting of polycarbonate resins, polyester resins, and polyester carbonate resins. In a preferred embodiment of the present invention, the thermoplastic resin can be a polycarbonate resin. In another preferred embodiment of the present invention, the thermoplastic resin can be a polyester resin. In yet another preferred embodiment of the present invention, the thermoplastic resin can be a polyester carbonate resin.

[0049] Thermoplastic resin properties (1) Refractive index One of the characteristics of the thermoplastic resin of the present invention is its high refractive index, and the refractive index (hereinafter sometimes abbreviated as "nd") measured at 25°C at a wavelength of 589 nm is preferably 1.650 to 1.720, more preferably 1.660 to 1.710, and even more preferably 1.670 to 1.700.

[0050] (2) Glass transition temperature Furthermore, one of the characteristics of the thermoplastic resin of the present invention is high heat resistance, and the glass transition temperature (hereinafter sometimes abbreviated as "Tg") is preferably 120 to 160°C, more preferably 130 to 155°C.

[0051] (3) Polystyrene equivalent molecular weight (Mw) In one embodiment of the present invention, the thermoplastic resin may have a polystyrene-equivalent molecular weight (Mw) of 10,000 to 100,000, preferably 15,000 to 70,000, and more preferably 20,000 to 50,000.

[0052] Thermoplastic resin composition In one embodiment of the present invention, the thermoplastic resin may contain one or more structural units derived from compounds represented by the following general formulas (a) to (e): In the present invention, the thermoplastic resin may contain one or more structural units derived from compounds represented by the following general formulas (a) to (e).

[0053] <Structural Unit Derived from a Compound Represented by General Formula (a)> [ka] (In formula (a), R c and R d are each independently 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≡CR h is selected from R h represents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 6 to 20 carbon atoms and containing one or more hetero ring atoms selected from O, N, and S, X represents a saturated carbon group having 1 to 5 carbon atoms; c and d each independently represent an integer of 0 to 10.

[0054] In a preferred embodiment of the present invention, in formula (a), R c and R d each independently represents 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 Selected from R h represents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 6 to 20 carbon atoms and containing one or more hetero ring atoms selected from O, N and S.

[0055] In formula (a), the aryl group more preferably has 6 to 18 carbon atoms, more preferably has 6 to 16 carbon atoms, more preferably has 6 to 14 carbon atoms, more preferably has 6 to 12 carbon atoms, and even more preferably has 6 to 10 carbon atoms.

[0056] In the formula (a), the heteroaryl group more preferably has 6 to 18 carbon atoms, more preferably has 8 to 16 carbon atoms, and even more preferably has 10 to 14 carbon atoms.

[0057] In the formula (a), the aryloxy group more preferably has 6 to 18 carbon atoms, more preferably has 6 to 16 carbon atoms, and even more preferably has 6 to 14 carbon atoms.

[0058] In formula (a), X may more preferably be an alkylene group having 1 to 4 carbon atoms, even more preferably an alkylene group having 1 to 3 carbon atoms, and even more preferably an alkylene group having 2 carbon atoms.

[0059] In formula (a), c and d may each independently be an integer of 0 to 5, more preferably an integer of 1 to 5, even more preferably an integer of 1 to 3, and even more preferably 1.

[0060] In a preferred embodiment of the present invention, in formula (a), Rc and R d may each independently be selected from the group consisting of a phenyl group, a naphthyl group, or [ka] X represents an alkylene group having 1 to 4 carbon atoms, more preferably an alkylene group having 1 to 3 carbon atoms, and even more preferably an alkylene group having 2 carbon atoms; c and d each independently represent an integer of 0 to 5, more preferably an integer of 1 to 5, even more preferably an integer of 1 to 3, and even more preferably 1.

[0061] When the thermoplastic resin of the present invention contains a structural unit derived from a compound represented by general formula (a), the thermoplastic resin is a polycarbonate resin, a polyester carbonate resin, or a polyester resin.

[0062] <Structural Unit Derived from a Compound Represented by General Formula (b)> [ka] (In formula (b), R a and R b each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms which may contain a heterocyclic atom selected from O, N, and S, an alkenyl group having 2 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms; X represents a saturated carbon group having 1 to 5 carbon atoms; a and b each independently represent an integer of 0 to 10.

[0063] In a preferred embodiment of the present invention, in formula (b), R a and R beach independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms which may contain a heterocyclic atom selected from O, N, and S, an alkenyl group having 2 to 15 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, or an aralkyl group having 7 to 17 carbon atoms;

[0064] In formula (b), the alkyl group may more preferably be an alkyl group having 1 to 6 carbon atoms, and even more preferably methyl.

[0065] In formula (b), the aryl group may be an aryl group having more preferably 6 to 16 carbon atoms, even more preferably 6 to 14 carbon atoms, even more preferably 6 to 12 carbon atoms, and even more preferably 6 to 10 carbon atoms.

[0066] In the formula (b), the alkenyl group may more preferably be an alkenyl group having 2 to 10 carbon atoms.

[0067] In the formula (b), the alkoxy group may more preferably be an alkoxy group having 1 to 3 carbon atoms.

[0068] In the formula (b), the aralkyl group may more preferably be an aralkyl group having 7 to 10 carbon atoms.

[0069] In formula (b), X may more preferably be an alkylene group having 1 to 4 carbon atoms, even more preferably an alkylene group having 1 to 3 carbon atoms, and even more preferably an alkylene group having 2 carbon atoms.

[0070] In formula (b), a and b may each independently be an integer of 0 to 5, more preferably an integer of 1 to 5, even more preferably an integer of 1 to 3, and even more preferably 1.

[0071] When the thermoplastic resin of the present invention contains a structural unit derived from a compound represented by general formula (b), the thermoplastic resin is a polycarbonate resin, a polyester carbonate resin, or a polyester resin.

[0072] <Structural Unit Derived from a Compound Represented by General Formula (c)> [ka] (In formula (c), R e and R f each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms which may contain a heterocyclic atom selected from O, N, and S, an alkenyl group having 2 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or an aralkyl group having 7 to 17 carbon atoms; X represents a saturated carbon group having 1 to 5 carbon atoms; e and f each independently represent an integer of 0 to 10.

[0073] In a preferred embodiment of the present invention, in formula (c), R e and R f each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms which may contain a heterocyclic atom selected from O, N, and S, an alkenyl group having 2 to 15 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, or an aralkyl group having 7 to 17 carbon atoms;

[0074] In formula (c), the alkyl group may more preferably be an alkyl group having 1 to 6 carbon atoms, and even more preferably methyl.

[0075] In formula (c), the aryl group may more preferably be an aryl group having 6 to 16 carbon atoms, even more preferably 6 to 14 carbon atoms, even more preferably 6 to 12 carbon atoms, and even more preferably 6 to 10 carbon atoms.

[0076] In the formula (c), the alkenyl group may more preferably be an alkenyl group having 2 to 10 carbon atoms.

[0077] In the formula (c), the alkoxy group may more preferably be an alkoxy group having 1 to 3 carbon atoms.

[0078] In the formula (c), the aralkyl group may more preferably be an aralkyl group having 7 to 10 carbon atoms.

[0079] In formula (c), X may more preferably be an alkylene group having 1 to 4 carbon atoms, even more preferably an alkylene group having 1 to 3 carbon atoms, and even more preferably an alkylene group having 2 carbon atoms.

[0080] In formula (c), e and f may each independently be an integer of 0 to 5, more preferably an integer of 1 to 5, even more preferably an integer of 1 to 3, and even more preferably 1.

[0081] When the thermoplastic resin of the present invention contains a structural unit derived from a compound represented by general formula (c), the thermoplastic resin is a polycarbonate resin, a polyester carbonate resin, or a polyester resin.

[0082] <Structural Unit Derived from a Compound Represented by General Formula (d)> [ka] (In formula (d), R represents a hydrogen atom, a methyl group, or an ethyl group.)

[0083] In a preferred embodiment of the present invention, in formula (d), R represents a hydrogen atom.

[0084] When the thermoplastic resin of the present invention contains a structural unit derived from a compound represented by general formula (d), the thermoplastic resin is a polycarbonate resin, a polyester carbonate resin, or a polyester resin.

[0085] <Constituent unit represented by general formula (e)> [ka] (In formula (e), R5 and R6 each independently represent 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≡CR h is selected from R h represents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 6 to 20 carbon atoms and containing one or more hetero ring atoms selected from O, N, and S, p and q each independently represent an integer of 0 to 10.

[0086] In a preferred embodiment of the present invention, in formula (e): R5 and R6 each independently represent 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, as well as -C≡CR h Selected from R h represents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 6 to 20 carbon atoms and containing one or more hetero ring atoms selected from O, N and S.

[0087] In formula (e), the aryl group more preferably has 6 to 18 carbon atoms, more preferably has 6 to 16 carbon atoms, more preferably has 6 to 14 carbon atoms, more preferably has 6 to 12 carbon atoms, and even more preferably has 6 to 10 carbon atoms.

[0088] In formula (e), the heteroaryl group more preferably has 6 to 18 carbon atoms, more preferably has 8 to 16 carbon atoms, and even more preferably has 10 to 14 carbon atoms.

[0089] In the formula (e), the aryloxy group more preferably has 6 to 18 carbon atoms, more preferably has 6 to 16 carbon atoms, and even more preferably has 6 to 14 carbon atoms.

[0090] In formula (e), p and q may each independently be an integer of more preferably 0 to 5, and even more preferably an integer of 0 to 1.

[0091] In a more preferred embodiment of the present invention, in formula (e): R5 and R6 may each independently be selected from the group consisting of a phenyl group, a naphthyl group, or [ka]

[0092] The structural unit represented by formula (e) is even more preferably derived from 2,2'-bis(hydroxycarbonylmethoxy)-1,1'-binaphthyl and compounds represented by the following structural formula, and is particularly preferably derived from 2,2'-bis(hydroxycarbonylmethoxy)-1,1'-binaphthyl. [ka]

[0093] When the thermoplastic resin of the present invention contains a structural unit represented by general formula (e), the thermoplastic resin is a polyester resin or a polyester carbonate resin.

[0094] <Polycarbonate resin> The polycarbonate resin used in the resin composition of the present invention may contain one or more of the structural units derived from the compounds represented by the general formulas (a) to (d) above as a diol component. In the present invention, the polycarbonate resin may contain one or more of the structural units derived from the compounds represented by the general formulas (a) to (d) above. The polycarbonate resin used in the resin composition of the present invention may contain other diol components as structural units. The structural units derived from the compounds represented by the general formulas (a) to (d) are as described above.

[0095] In one embodiment of the present invention, the diol component may be derived from a compound represented by the general formula (a) above. In one embodiment of the present invention, the diol component may be derived from a compound represented by the general formula (b) above. In one embodiment of the present invention, the diol component may be derived from a compound represented by the general formula (c) above. In one embodiment of the present invention, the diol component may be derived from a compound represented by the general formula (d) above.

[0096] <Manufacturing method of polycarbonate resin> The polycarbonate resin can be produced by a conventional method.

[0097] In the phosgene method, diol and phosgene are typically reacted in the presence of an acid binder and a solvent. Examples of acid binders include pyridine and alkali metal hydroxides such as sodium hydroxide and potassium hydroxide. Examples of solvents include methylene chloride and chloroform. To accelerate the condensation polymerization reaction, it is preferable to use a catalyst such as a tertiary amine (e.g., triethylamine) or a quaternary ammonium salt (e.g., benzyltriethylammonium chloride). Furthermore, to control the degree of polymerization, it is preferable to add a monofunctional compound (e.g., phenol, pt-butylphenol, p-cumylphenol, or alkyl-substituted phenol) as a molecular weight regulator. If desired, a small amount of an antioxidant (e.g., sodium sulfite or hydrosulfite) or a branching agent (e.g., phloroglucin or isatin bisphenol) may be added. The reaction temperature is typically 0 to 150°C, preferably 5 to 40°C. The reaction time varies depending on the reaction temperature, but is typically 0.5 minutes to 10 hours, preferably 1 minute to 2 hours. It is also desirable to maintain the pH of the reaction system at 10 or higher during the reaction.

[0098] On the other hand, in the transesterification method, a diol and a bisaryl carbonate are mixed and reacted at high temperature under reduced pressure. Examples of bisaryl carbonates include bisaryl carbonates such as diphenyl carbonate, di-p-tolyl carbonate, phenyl-p-tolyl carbonate, di-p-chlorophenyl carbonate, and dinaphthyl carbonate. These compounds can be used alone or in combination. The reaction is usually carried out at a temperature ranging from 150 to 350°C, preferably from 200 to 300°C, and the final pressure reduction is preferably 1 mmHg or less, allowing phenols derived from the bisaryl carbonate produced by the transesterification reaction to be distilled out of the system. The reaction time varies depending on the reaction temperature and the degree of vacuum, but is usually about 1 to 24 hours. The reaction is preferably carried out under an inert gas atmosphere such as nitrogen or argon.

[0099] The content of the dicarboxylic acid chloride, phosgene, or biaryl carbonate component is preferably less than 42 mol%, more preferably less than 30 mol%, and even more preferably less than 20 mol%, based on 100 mol% of the dicarboxylic acid component.

[0100] <Polyester resin> The polyester resin used in the resin composition of the present invention may contain a structural unit represented by the general formula (e) as a carboxylic acid diester component. The structural unit represented by the general formula (e) is as described above. The polyester resin used in the resin composition of the present invention can use any diol component as its structural unit.

[0101] In the polyester resin used in the resin composition of the present invention, the diol component may be, for example, bisphenols, binaphthols, etc., but is not limited thereto. In one embodiment of the present invention, the polyester resin used in the resin composition of the present invention may contain one or more types of structural units derived from the compounds represented by the above general formulas (a) to (d) as the diol component. In the present invention, the polyester resin may contain one or more types of structural units derived from the compounds represented by the above general formulas (a) to (d). The polyester resin used in the resin composition of the present invention may further contain other diol components as structural units. The structural units derived from the compounds represented by the general formulas (a) to (d) are as described above.

[0102] In one embodiment of the present invention, the diol component may be derived from a compound represented by the general formula (a) above. In one embodiment of the present invention, the diol component may be derived from a compound represented by the general formula (b) above. In one embodiment of the present invention, the diol component may be derived from a compound represented by the general formula (c) above. In one embodiment of the present invention, the diol component may be derived from a compound represented by the general formula (d) above.

[0103] The polyester resin used in the resin composition of the present invention may contain, as other polymerization components, dicarboxylic acid components other than the structural units represented by the general formula (e) above, and / or diol components other than the structural units derived from the compounds represented by the general formulas (a) to (d) above.

[0104] In one embodiment of the present invention, other dicarboxylic acid components that can be used in the polyester resin include aliphatic dicarboxylic acid components such as malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, methylmalonic acid, and ethylmalonic acid; monocyclic aromatic dicarboxylic acid components such as phthalic acid, isophthalic acid, and terephthalic acid; polycyclic aromatic dicarboxylic acid components such as 2,7-naphthalenedicarboxylic acid, 2,3-naphthalenedicarboxylic acid, 1,4-naphthalenedicarboxylic acid, 1,8-naphthalenedicarboxylic acid, anthracenedicarboxylic acid, and phenanthrenedicarboxylic acid; biphenyl dicarboxylic acid components such as 2,2'-biphenyldicarboxylic acid; and alicyclic dicarboxylic acid components such as 1,4-cyclodicarboxylic acid and 2,6-decalindicarboxylic acid. These may be used alone or in combination. Acid chlorides and esters may also be used as derivatives of these. Among these, monocyclic aromatic dicarboxylic acid components, polycyclic aromatic dicarboxylic acid components, and biphenyl dicarboxylic acid components are preferred because they tend to increase heat resistance and refractive index.

[0105] In one embodiment of the present invention, other diol components that can be used in the polyester resin include aliphatic diol components such as ethylene glycol, propanediol, butanediol, pentanediol, hexanediol, heptanediol, octanediol, and nonanediol; alicyclic diol components such as tricyclo[5.2.1.02,6]decanedimethanol, cyclohexane-1,4-dimethanol, decalin-2,6-dimethanol, norbornanedimethanol, pentacyclopentadecanedimethanol, cyclopentane-1,3-dimethanol, spiroglycol, and isosorbide; hydroquinone, resorcinol, 2,2-bis(4-hydroxyphenyl)propane, 2,2-bis(3-methyl-4-hydroxyphenyl)propane, 1,1-bis(4-hydroxyphenyl)-1-phenylethane, bis(4-hydroxyphenyl)diphenylmethane, and 1,3-bis(2-(4-hydroxyphenyl)-2-propane). Examples of aromatic diol components include bis(4-hydroxyphenyl)benzene, bis(4-hydroxyphenyl)sulfone, bis(4-(2-hydroxyethoxy)phenyl)sulfone, bis(4-hydroxyphenyl)sulfide, 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane, 1,1-bis(4-hydroxyphenyl)cyclohexane, biphenol, 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthyl, 1,1'-bi-2-naphthol, dihydroxynaphthalene, bis(2-hydroxyethoxy)naphthalene, and 10,10-bis(4-hydroxyphenyl)anthrone. These may be used alone or in combination of two or more. Among these, ethylene glycol and 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthyl are preferred because they improve moldability while easily suppressing decreases in heat resistance and refractive index.

[0106] <Method of manufacturing polyester resin> The polyester resin can be produced by a conventional method.

[0107] The polyester resin used in the resin composition of the present invention may be prepared by subjecting a dicarboxylic acid and a diol compound to an esterification reaction or an ester exchange reaction, and then subjecting the resulting reaction product to a polycondensation reaction to obtain a polymer having a desired molecular weight.

[0108] Specifically, for example, it is preferable to mix a diol component and a dicarboxylic acid component or a diester thereof in the presence of an inert gas and react them under reduced pressure, typically at 120 to 350° C., and preferably at 150 to 300° C. The degree of reduced pressure is changed stepwise, and finally reduced to 0.13 kPa or less to distill off the produced water or alcohols from the system, and the reaction time is typically about 1 to 10 hours.

[0109] As the polymerization catalyst, known compounds can be used, and preferred examples include antimony compounds, titanium compounds, germanium compounds, tin compounds, and aluminum compounds. Examples of such compounds include oxides, acetates, carboxylates, hydrides, alcoholates, halides, carbonates, and sulfates of antimony, titanium, germanium, tin, and aluminum. These compounds can also be used in combination of two or more. Among these, tin, titanium, and germanium compounds are preferred from the viewpoint of the melt stability and color of the thermoplastic resin.

[0110] The transesterification catalyst may be a known one, such as a compound containing manganese, magnesium, titanium, zinc, aluminum, calcium, cobalt, sodium, lithium, or lead. Specific examples include oxides, acetates, carboxylates, hydrides, alcoholates, halides, carbonates, and sulfates containing these elements. Among these, oxides, acetates, alcoholates, and other compounds of manganese, magnesium, zinc, titanium, and cobalt are preferred from the viewpoints of the melt stability, color, and minimal polymer insoluble matter of the thermoplastic resin. Manganese, magnesium, and titanium compounds are particularly preferred. These compounds may be used in combination of two or more.

[0111] As described above, the polyester resin of the present invention may contain, as copolymerization components, other dicarboxylic acid components other than the structural units represented by the formula (e) and / or other diol components other than the structural units derived from the compounds represented by the general formulas (a) to (d).

[0112] <Polyester carbonate resin> The polyester carbonate resin used in the resin composition of the present invention may contain one or more structural units derived from the compounds represented by the general formulas (a) to (d) above, and / or a structural unit represented by the general formula (e). In the present invention, the polyester carbonate resin may contain one or more structural units derived from the compounds represented by the general formulas (a) to (d) above, as a dicarboxylic acid component. The structural units derived from the compounds represented by the general formulas (a) to (d) and the structural unit represented by the general formula (e) are as described above.

[0113] In one embodiment of the present invention, the diol component may be derived from a compound represented by the general formula (a) above. In one embodiment of the present invention, the diol component may be derived from a compound represented by the general formula (b) above. In one embodiment of the present invention, the diol component may be derived from a compound represented by the general formula (c) above. In one embodiment of the present invention, the diol component may be derived from a compound represented by the general formula (d) above. The polyester carbonate resin used in the resin composition of the present invention may contain, as its constituent units, diol components other than the constituent units derived from the compounds represented by the general formulas (a) to (d) and dicarboxylic acid components other than the constituent units represented by the general formula (e).

[0114] <Method for producing polyester carbonate resin> The polyester carbonate resin can be produced by a conventional method.

[0115] The polyester carbonate resin used in the resin composition of the present invention can be produced by combining a phosgene method in which a dicarboxylic acid and a diol compound are subjected to an esterification reaction or a transesterification reaction, followed by a reaction with a dicarboxylic acid chloride or phosgene, or a transesterification method in which a diol, a dicarboxylic acid, and a biaryl carbonate are reacted. The esterification reaction, the transesterification reaction, the phosgene method, and the transesterification method are as described above.

[0116] <Additives> The thermoplastic resin of the present invention can be used as a thermoplastic resin composition by appropriately adding additives such as a heat stabilizer, an antioxidant, a release agent, a plasticizer, a filler, an ultraviolet absorber, a rust inhibitor, a dispersant, an antifoaming agent, and a leveling agent, as needed.

[0117] The release agent is preferably one comprising 90% by weight or more of an ester of alcohol and fatty acid. Specific examples of the ester of alcohol and fatty acid include esters of monohydric alcohol and fatty acid and / or partial or complete esters of polyhydric alcohol and fatty acid. The ester of monohydric alcohol and fatty acid is preferably an ester of a monohydric alcohol having 1 to 20 carbon atoms and a saturated fatty acid having 10 to 30 carbon atoms. Furthermore, the partial or complete ester of a polyhydric alcohol and fatty acid is preferably a partial or complete ester of a polyhydric alcohol having 1 to 25 carbon atoms and a saturated fatty acid having 10 to 30 carbon atoms. Specific examples of the ester of monohydric alcohol and saturated fatty acid include stearyl stearate, palmityl palmitate, butyl stearate, methyl laurate, isopropyl palmitate, etc., with stearyl stearate being preferred.

[0118] Specific examples of partial or full esters of polyhydric alcohols and saturated fatty acids include stearic acid monoglyceride, stearic acid diglyceride, stearic acid triglyceride, stearic acid monosorbitate, behenic acid monoglyceride, pentaerythritol monostearate, pentaerythritol tetrastearate, pentaerythritol tetrapelargonate, propylene glycol monostearate, biphenyl biphenate, sorbitan monostearate, 2-ethylhexyl stearate, and full or partial esters of dipentaerythritol such as dipentaerythritol hexastearate. Among these esters, stearic acid monoglyceride, stearic acid triglyceride, pentaerythritol tetrastearate, and mixtures of stearic acid triglyceride and stearyl stearate are preferably used.

[0119] The amount of the ester in the release agent is preferably 90% by weight or more, and more preferably 95% by weight or more, when the release agent is taken as 100% by weight.

[0120] The release agent to be blended in the thermoplastic resin composition is preferably in the range of 0.005 to 2.0 parts by weight, more preferably 0.01 to 0.6 parts by weight, and even more preferably 0.02 to 0.5 parts by weight, per 100 parts by weight of the thermoplastic resin.

[0121] Examples of the heat stabilizer include phosphorus-based heat stabilizers, sulfur-based heat stabilizers, and hindered phenol-based heat stabilizers.

[0122] Among the phosphorus-based heat stabilizers, tetrakis(2,4-di-tert-butylphenyl)-4,4'-biphenylene diphosphonite is preferably used.

[0123] The content of the phosphorus-based heat stabilizer in the thermoplastic resin is preferably 0.001 to 0.2 parts by weight relative to 100 parts by weight of the thermoplastic resin.

[0124] Of the hindered phenol-based heat stabilizers, octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate is particularly preferably used.

[0125] The content of the hindered phenol-based heat stabilizer in the thermoplastic resin is preferably 0.001 to 0.3 parts by weight relative to 100 parts by weight of the thermoplastic resin.

[0126] The ultraviolet absorber is preferably at least one ultraviolet absorber selected from the group consisting of benzotriazole-based ultraviolet absorbers, benzophenone-based ultraviolet absorbers, triazine-based ultraviolet absorbers, cyclic iminoester-based ultraviolet absorbers, and cyanoacrylate-based ultraviolet absorbers.

[0127] Among benzotriazole-based UV absorbers, 2-(2-hydroxy-5-tert-octylphenyl)benzotriazole and 2,2'-methylenebis[4-(1,1,3,3-tetramethylbutyl)-6-(2H-benzotriazol-2-yl)phenol] are more preferred. Benzophenone-based UV absorbers include 2-hydroxy-4-n-dodecyloxybenzophenone and 2-hydroxy-4-methoxy-2'-carboxybenzophenone. Triazine-based UV 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. As the cyclic iminoester-based ultraviolet absorber, 2,2'-p-phenylenebis(3,1-benzoxazin-4-one) is particularly suitable.

[0128] The amount of ultraviolet absorber to be blended is preferably 0.01 to 3.0 parts by weight per 100 parts by weight of the thermoplastic resin, and within this range of blending amount, it is possible to impart sufficient weather resistance to the thermoplastic resin molded product depending on the application.

[0129] <Method of manufacturing resin composition> The method for producing the resin composition is not particularly limited, and the resin composition can be produced by a known method. In one embodiment, the method for producing the resin composition includes a step of mixing a thermoplastic resin with compounding agents. The method may further include a step of mixing at least one of a solvent and an additive. For example, the resin composition can be produced by adding the compounding agents and additives to the thermoplastic resin sequentially or simultaneously and mixing them. The mixing step can be carried out by a conventional method, such as a method of kneading using an extruder or a method of dissolving the resin and compounding agents in a solvent (e.g., methylene chloride, THF, etc.) to prepare solutions and then mixing the solutions.

[0130] <Physical properties of resin composition> The resin composition of the present invention has a low Tg and high flowability. Therefore, the resin composition of the present invention can be injection molded. The physical properties of the resin composition will be described in detail in the examples.

[0131] 2. Molded products The resin composition of the present invention can be suitably used for optical components. In one embodiment of the present invention, an optical component comprising the resin composition of the present invention is provided. In one embodiment of the present invention, optical components include, but are not limited to, optical disks, transparent conductive substrates, optical cards, sheets, films, optical fibers, lenses, prisms, optical films, substrates, optical filters, hard coat films, and the like. The resin composition of the present invention can be molded by a casting method with high flow, and is therefore particularly suitable for producing thin optical components. In a preferred embodiment of the present invention, the optical component produced using the resin composition of the present invention may be an optical lens. In another preferred embodiment of the present invention, the optical component produced using the resin composition of the present invention may be an optical film.

[0132] When an optical element containing the resin composition of the present invention is produced by injection molding, molding is preferably performed under conditions of a cylinder temperature of 260 to 350°C and a mold temperature of 90 to 170°C. More preferably, molding is performed under conditions of a cylinder temperature of 270 to 320°C and a mold temperature of 100 to 160°C. If the cylinder temperature is higher than 350°C, the resin composition will decompose and discolor, and if it is lower than 260°C, the melt viscosity will be high, making molding difficult. Furthermore, if the mold temperature is higher than 170°C, it will be difficult to remove a molded piece made of the resin composition from the mold. On the other hand, if the mold temperature is lower than 90°C, the resin will harden too quickly in the mold during molding, making it difficult to control the shape of the molded piece and making it difficult to sufficiently transfer the shape of the molded piece.

[0133] <Optical lenses> In one embodiment of the present invention, the resin composition can be suitably used for optical lenses. Optical lenses produced using the resin composition of the present invention have a high refractive index and excellent heat resistance, and are therefore extremely useful in fields where expensive high-refractive-index glass lenses have traditionally been used, such as telescopes, binoculars, and television projectors.

[0134] The optical lens of the present invention is preferably implemented as an aspherical lens, if necessary. Since a single aspherical lens can substantially eliminate spherical aberration, it is not necessary to eliminate spherical aberration by combining multiple spherical lenses, which allows for weight reduction and reduced molding costs. Therefore, aspherical lenses are particularly useful as camera lenses, among other optical lenses.

[0135] Furthermore, the optical lens of the present invention has high molding fluidity and is therefore particularly useful as a material for optical lenses that are thin, small, and have complex shapes. Specifically, the lens size preferably has a central thickness of 0.05 to 3.0 mm, more preferably 0.05 to 2.0 mm, and even more preferably 0.1 to 2.0 mm. The diameter is preferably 1.0 to 20.0 mm, more preferably 1.0 to 10.0 mm, and even more preferably 3.0 to 10.0 mm. The lens preferably has a meniscus shape, with one surface convex and the other concave.

[0136] The optical lens of the present invention can be formed by any method such as mold molding, cutting, polishing, laser processing, electrical discharge processing, etching, etc. Among these, mold molding is more preferred in terms of production costs.

[0137] <Optical film> In one embodiment of the present invention, the resin composition can be suitably used for optical films. Optical films produced using the polycarbonate resin of the present invention have excellent transparency and heat resistance, and are therefore suitably used for liquid crystal substrate films, optical memory cards, etc.

[0138] To prevent foreign matter from getting into the optical film as much as possible, the molding environment must naturally be a low-dust environment, preferably class 6 or less, more preferably class 5 or less. [Example]

[0139] Examples of the present invention will be shown below together with comparative examples to explain the details of the invention, but the present invention is not limited to these examples.

[0140] 1) Glass transition temperature (Tg) The glass transition temperature (Tg) was measured by a differential scanning calorimeter (DSC) under the following specific conditions: Equipment: Hitachi High-Tech Science Corporation DSC7000X Sample amount: 5 mg Atmosphere: Nitrogen gas atmosphere Temperature rise condition: 10°C / min

[0141] 2) Melt volume flow rate (MVR) (cm 3 / 10min) Measured using a Melt Indexer T-111 (manufactured by Toyo Seiki Seisakusho) at 260°C and a load of 2.16 kg according to the method of ISO 1133.

[0142] 3) Refractive index (nd) The 0.1 mm thick film made of polycarbonate resin produced in the examples was measured using an Abbe refractometer according to the method of JIS-K-7142.

[0143] 4) Abbe number (ν) The refractive index of a 0.1 mm thick film made of polycarbonate resin produced in the examples was measured at wavelengths of 486 nm, 589 nm, and 656 nm at 23°C using an Abbe refractometer, and the Abbe number was calculated using the following formula. ν=(nd-1) / (nF-nC) nd: Refractive index at a wavelength of 589 nm nC: Refractive index at a wavelength of 656 nm nF: Refractive index at a wavelength of 486 nm

[0144] 5) Mass average molecular weight (Mw) The mass average molecular weight of the resin and 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 × 3 Tosoh Corporation, TSKgel guardcolumn SuperH-H x 1 Tosoh Corporation, TSKgel SuperH-RC x 1 Detector: RI detector Standard polystyrene: Tosoh Corporation, Standard Polystyrene Kit PStQuick C Sample solution: 0.2% by mass tetrahydrofuran solution Eluent: tetrahydrofuran ·Eluent flow rate: 0.6mL / min Column temperature: 40℃

[0145] 6) Formability (fluidity) The resin composition was vacuum dried at 120°C for 4 hours, and then injection molded into a disk-shaped plate with a diameter of 50 mm and a thickness of 1.0 mm using an injection molding machine (FANUC ROBOSHOT α-S30iA) at a cylinder temperature of 270°C and a mold temperature of Tg-10°C. The moldability (fluidity) was evaluated visually. Flow marks in molding (visual observation) A: No flow marks Flow marks in molding (visual observation) B: Almost no flow marks Flow marks in molding (visual observation) C: Slight flow marks Flow marks in molding (visual observation) D: Flow marks present

[0146] 7) Thermogravimetric decrease starting temperature (℃) Measurement was performed using a thermogravimetric and differential thermal analyzer (TG / DTA) (manufactured by Hitachi High-Tech Science, TGDTA7300). The measurement sample was 2 mg and was weighed into a platinum pan (Pt open-type sample container, φ5.2 H2.5 mm). Measurements were performed under a nitrogen atmosphere (nitrogen flow rate: 250 ml / min). 0.00519 g of α-alumina was used as a reference substance in the reference cell. The sample temperature was adjusted to 30°C and heated to 550°C at a rate of 10°C / min. Measurements were performed at the temperature at which a weight loss of 5% by mass occurred, which was defined as the "thermal weight loss onset temperature."

[0147] (Resin Production Example 1) Resin 1: EP8000 The raw materials used were 13.000 kg (22.007 mol) of 9,9-bis(4-(2-hydroxyethoxy)-3-phenylphenyl)fluorene (BPPEF) having the following structure, 8.000 kg (21.365 mol) of 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene (BNE), 9.650 kg (45.048 mol) of DPC, and 2.21 × 10 sodium bicarbonate. -2 g (2.63 × 10 -4The resulting mixture (mol) was placed in a 50-liter reactor equipped with a stirrer and a distillation device, and after replacing the atmosphere with nitrogen, the mixture was heated to 205°C over 1 hour under a nitrogen atmosphere of 760 Torr and stirred. [ka]

[0148] After the raw materials were completely dissolved, the vacuum was adjusted to 150 Torr over 15 minutes and held at 205°C and 150 Torr for 20 minutes to carry out the transesterification reaction. The temperature was then raised to 240°C at a rate of 37.5°C / hr and held at 240°C and 150 Torr for 10 minutes. The pressure was then adjusted to 120 Torr over 10 minutes and held at 240°C and 120 Torr for 70 minutes. The pressure was then adjusted to 100 Torr over 10 minutes and held at 240°C and 100 Torr for 10 minutes. The pressure was then reduced to 1 Torr or less over 40 minutes, and the polymerization reaction was carried out under stirring at 240°C and 1 Torr for 10 minutes. After the reaction was completed, nitrogen was blown into the reactor to increase the pressure, and the resulting polycarbonate resin was pelletized and extracted to obtain Resin 1.

[0149] (Resin Production Example 2) Resin 2: EP10000 In Production Example 1, raw materials were 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene (BNE) 14.978 kg (40.000 mol), 9,9-bis[6-(2-hydroxyethoxy)naphthalen-2-yl]fluorene (BNEF) 24.239 kg (45.000 mol), DPBHBNA 7.899 kg (15.000 mol), DPC 22.236 kg (103.800 mol), sodium bicarbonate 5.09 × 10 -2 g (6.06 × 10 -4 The same procedure as in Production Example 1 was carried out except that the amount of methyl methyl ether was changed to methyl methyl ether (mol), to obtain a polycarbonate resin (Resin 2). [ka]

[0150] (Resin Production Example 3) Resin 3: EP6000 In Production Example 1, raw materials were 19.260 kg (43.921 mol) of 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (BPEF), 9.780 kg (45.655 mol) of diphenyl carbonate (DPC), and 2.21 × 10 sodium bicarbonate. -2 g (2.63 × 10 -4 The same procedure as in Production Example 1 was carried out except that the amount of methyl methyl ether was changed to methyl methyl ether (mol), to obtain a polycarbonate resin (Resin 3). [ka]

[0151] (Resin Production Example 4) Resin 4: EP3500 23.50 kg (105.70 mol) of decahydro-1,4:5,8-dimethanonaphthalene-2,6(7)-dimethanol (D-NDM) represented by the following structural formula (a), 22.98 kg (107.27 mol) of DPC, and 130.00 mg (1.5 × 10 -3 (mol) was placed in a 50L reactor equipped with a stirrer and 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 held at 205 ° C and 200 Torr for 30 minutes. The temperature was then increased 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 conditions of 240 ° C and 1 Torr or less. After confirming that the reaction solution had reached an appropriate melt viscosity, stirring was stopped, and nitrogen was blown into the reactor to pressurize, yielding a polycarbonate resin (Resin 4). [ka]

[0152] (Combination Drug Manufacturing Example 1) Oligomer compounding agent: BNE-3PC As raw materials, 84.38 g (0.2253 mol) of 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene (BNE), 65.12 g (0.3042 mol) of DPC, and 2.21 × 10 sodium bicarbonate were used. -4 g (2.63 × 10 -6 (mol) was placed in a 500-milliliter reactor equipped with a stirrer and distillation device, and after nitrogen substitution, the mixture was heated to 205°C over 1 hour under a nitrogen atmosphere of 760 Torr and stirred. After complete dissolution of the raw materials, the vacuum was adjusted to 150 Torr over 15 minutes and maintained at 205°C and 150 Torr for 20 minutes to carry out an ester exchange reaction. The temperature was then increased to 240°C at a rate of 37.5°C / hr and maintained at 240°C and 150 Torr for 10 minutes. The pressure was then adjusted to 120 Torr over 10 minutes and maintained at 240°C and 120 Torr for 70 minutes. The pressure was then adjusted to 100 Torr over 10 minutes and maintained at 240°C and 100 Torr for 10 minutes. The reaction was terminated by reducing the pressure to 1 Torr or less over 40 minutes. Nitrogen was blown into the reactor to pressurize it, and the resulting polycarbonate oligomer was removed from the reactor. The polycarbonate oligomer thus obtained had an average number of repeating units of 3 as determined by NMR, and a mass average molecular weight of 1,400 as determined by GPC.

[0153] (Examples 1 to 7, Comparative Examples 1 to 3) The resin, compounding agent, pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate] (ADEKA AO-60: antioxidant) 1000 ppm, stearic acid monoglyceride (Riken Vitamin S-100A: mold release agent) 1500 ppm, and 3,9-bis(2,6-di-tert-butyl-4-methylphenoxy)-2,4,8,10-tetrakis were mixed in the mass ratios shown in the table. The mixture was dry-mixed with 300 ppm of oxa-3,9-diphosphaspiro[5.5]undecane (PEP-36, manufactured by ADEKA Corporation: antioxidant) using a tumbler, and melt-kneaded using a twin-screw extruder (IPEC Corporation, IPT-type 35 mm co-rotating twin-screw extruder, L / D=38) at a cylinder temperature of 250°C, a vent pressure of 25 Torr, and a discharge rate of 20 kg / hour, and extruded as strands to obtain a pellet-shaped polycarbonate resin composition.

[0154] The glass transition temperature (Tg), melt volume flow rate (MVR), refractive index (nd), and Abbe number (ν) of the obtained resin composition were measured or calculated, and the moldability (fluidity) was visually observed. The results are shown in Table 1.

[0155] [Table 1]

[0156] As shown in Table 1, the resin composition of the present invention is a thermoplastic resin composition with excellent optical properties, exhibiting high flowability and moldability without impairing the properties of optical resin compositions. According to the present invention, optical components such as optical lenses and optical films can be precisely molded from this resin composition.

Claims

1. A thermoplastic resin, a compounding agent having a naphthalene structure and / or a fluorene structure; A resin composition comprising: The compounding agent having a naphthalene structure and / or a fluorene structure includes one or more compounds selected from compounds including a structural unit represented by any one of the following general formulas (1) to (3): the compounding agent having a naphthalene structure and / or a fluorene structure is at least one selected from the group consisting of a diol monomer having a structural unit represented by any one of general formulas (1) to (3) and a polycarbonate oligomer containing a structural unit represented by any one of general formulas (1) to (3) as a diol structure, a mass ratio of the thermoplastic resin to the compounding agent is thermoplastic resin: compounding agent=97:3 to 70:30; The thermoplastic resin contains a structural unit derived from a compound represented by the following general formula (a): the thermoplastic resin is selected from the group consisting of polycarbonate resin, polyester resin, and polyester carbonate resin; The polystyrene-equivalent molecular weight (Mw) of the thermoplastic resin is 10,000 to 100,000, The weight average molecular weight of the compounding agent is less than 10,000. Resin composition. [Chemical formula 1] (In formula (1), Ra and Rb each independently represent a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms which may contain a heterocyclic atom selected from O, N, and S, an alkenyl group having 2 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms; X represents a saturated carbon group having 1 to 5 carbon atoms; a and b each independently represent an integer of 0 to 10. [Case 2] (In formula (2), Rc and Rd are each independently selected from 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-Rh; Rh represents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 6 to 20 carbon atoms and containing one or more hetero ring atoms selected from O, N, and S; X represents a saturated carbon group having 1 to 5 carbon atoms; c and d each independently represent an integer of 0 to 10. [Chemical 3] (In formula (3), Re and Rf each independently represent a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms which may contain a heterocyclic atom selected from O, N, and S, an alkenyl group having 2 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms; X represents a saturated carbon group having 1 to 5 carbon atoms; e and f each independently represent an integer of 0 to 5. [C4] (In formula (a), Rc and Rd are each independently selected from 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-Rh; Rh represents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 6 to 20 carbon atoms and containing one or more hetero ring atoms selected from O, N, and S; X represents a saturated carbon group having 1 to 5 carbon atoms; c and d each independently represent an integer of 0 to 10.

2. The resin composition according to claim 1, wherein the compounding agent having a naphthalene structure and / or a fluorene structure is a polycarbonate oligomer containing, as a diol structure, a structural unit represented by any one of general formulas (1) to (3), wherein Ra, Rb, Rc, Rd, Re, Rf, a, b, c, d, e, and f are each as defined in claim 1.

3. The resin composition according to claim 2, wherein the polycarbonate oligomer containing a structural unit represented by any one of general formulas (1) to (3) as a diol structure is represented by any one of the following formulas, wherein Ra, Rb, Rc, Rd, Re, Rf, a, b, c, d, e, and f are each as defined in claim 1: [C5]

4. The resin composition according to any one of claims 1 to 3, wherein the compounding agent has a 5% thermal mass loss starting temperature (5% thermal mass loss temperature) of 260 ° C. or higher.

5. The resin composition according to any one of claims 1 to 4, wherein the compounding agent has a mass average molecular weight of 5,000 or less.

6. The resin composition according to any one of claims 1 to 5, wherein the mass ratio of the thermoplastic resin to the compounding agent is thermoplastic resin: compounding agent = 96:4 to 70:

30.

7. The resin composition according to any one of claims 1 to 6, wherein the thermoplastic resin has a polystyrene-equivalent molecular weight (Mw) of 15,000 to 70,000.

8. An optical member comprising the resin composition according to any one of claims 1 to 7.

9. An optical lens comprising the resin composition according to any one of claims 1 to 7.

10. An optical film comprising the resin composition according to any one of claims 1 to 7.

Images