Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/04—Oxygen-containing compounds
  • C08K5/10—Esters; Ether-esters
  • C08K5/109—Esters; Ether-esters of carbonic acid, e.g. R-O-C(=O)-O-R
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
  • C07C69/96—Esters of carbonic or haloformic acids
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L101/00—Compositions of unspecified macromolecular compounds
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
  • C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
  • C08L69/005—Polyester-carbonates
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K2201/00—Specific properties of additives
  • C08K2201/001—Conductive additives

Definitions

• Optical glass or optical resin is used as the material for the optical lenses used in 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., but has problems of high material cost, poor moldability, and low productivity.
• thermoplastic resin and a compounding agent As a thermoplastic resin and a compounding agent, the set n number is 3 or more and less than 15, or the average number of repeating units obtained by mass spectrometric measurement by electrolytic desorption mass spectrometry (FD-MS) is 2 A thermoplastic resin composition containing an aromatic carbonate oligomer (A) having a molecular weight of ⁇ 6.
• FD-MS electrolytic desorption mass spectrometry
• R c and R d 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, or a cycloalkyl group having 5 to 20 carbon atoms.
• thermoplastic resin composition according to any one of ⁇ 1> to ⁇ 6> above, wherein the thermoplastic resin has a set n number of 15 to 1,000.
• R c and R d 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, or a cycloalkyl group having 5 to 20 carbon atoms.
• thermoplastic resin composition of the present invention comprises a thermoplastic resin and a compounding agent with a set n number of 3 or more and less than 15, or a mass determined by electrolytic desorption mass spectrometry (FD-MS) and an aromatic carbonate oligomer (A) having an average number of repeating units of 2 to 6 as determined by analytical measurement.
• FD-MS electrolytic desorption mass spectrometry
• A aromatic carbonate oligomer
• R c and R d each independently represent one or more hetero groups selected from aryl groups having 6 to 20 carbon atoms, O, N and S.
• the aryl group preferably has 6 to 18 carbon atoms, more preferably 6 to 16 carbon atoms, still more preferably 6 to 14 carbon atoms, and even more preferably 6 carbon atoms. 12, preferably 6 to 10 carbon atoms.
• the heteroaryl group preferably has 6 to 18 carbon atoms, more preferably 8 to 16 carbon atoms, and still more preferably 10 to 14 carbon atoms.
• the aryloxy group preferably has 6 to 18 carbon atoms, more preferably 6 to 16 carbon atoms, and still more preferably 6 to 14 carbon atoms.
• X is preferably an alkylene group having 1 to 4 carbon atoms, more preferably an alkylene group having 1 to 3 carbon atoms, and particularly preferably an alkylene group having 2 carbon atoms.
• c and d are each independently preferably an integer of 0 to 5, more preferably an integer of 1 to 5, still more preferably an integer of 1 to 3, especially 1 is preferred.
• R e and R f are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, an alkyl group having 1 to 10 carbon atoms, or a heterocyclic atom selected from O, N and S represents an aryl group having 6 to 18 carbon atoms, 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, which may contain .
• R e and R f each independently preferably represent a hydrogen atom, a methyl group or a phenyl group.
• the alkyl group may preferably be an alkyl group having 1 to 6 carbon atoms, more preferably methyl.
• the aryl group preferably has 6 to 16 carbon atoms, more preferably 6 to 14 carbon atoms, still more preferably 6 to 12 carbon atoms, and particularly preferably 6 to 10 carbon atoms.
• the alkenyl group may preferably be an alkenyl group having 2 to 10 carbon atoms.
• the alkoxy group may preferably be an alkoxy group having 1 to 3 carbon atoms.
• the aralkyl group may preferably be an aralkyl group having 7 to 10 carbon atoms.
• the structural unit represented by general formula (2) is particularly preferably a structural unit represented by the following formula.
• p-tert-butylphenol (PTBP) dissolved in dichloromethane is added, emulsified by vigorous stirring for a predetermined time, then a polymerization catalyst is added, and polymerized for about 10 to 60 minutes.
• the aromatic carbonate oligomer (A) can be obtained from this purified substance by evaporating off the organic solvent.
• thermoplastic resin of the present invention has high heat resistance, and the glass transition temperature (hereinafter sometimes abbreviated as “Tg”) is 120 to It is preferably 160°C, more preferably 130 to 155°C.
• thermoplastic resin is particularly preferably a polycarbonate resin represented by the following structural formula.
• the polycarbonate resin used in the thermoplastic resin composition of the present invention may contain, as a diol component, one or more structural units derived from the compound represented by the general formula (3).
• the polycarbonate resin may contain one of the structural units derived from the compound represented by the general formula (3), or may contain two or more of them.
• the polycarbonate resin used in the thermoplastic resin composition of the present invention may contain other diol components as its constituent units.
• a monofunctional compound such as phenol, pt-butylphenol, p-cumylphenol, alkyl-substituted phenol
• a small amount of an antioxidant such as sodium sulfite or hydrosulfite or a branching agent such as phloroglucin or isatin bisphenol may be added.
• the reaction temperature is generally 0 to 150°C, preferably 5 to 40°C. Although the reaction time depends on the reaction temperature, it is usually 0.5 minutes to 10 hours, preferably 1 minute to 2 hours. Moreover, it is desirable to keep the pH of the reaction system at 10 or higher during the reaction.
• a diol and a bisaryl carbonate are mixed and reacted at a high temperature under reduced pressure.
• bisaryl carbonates include bisaryl carbonates such as diphenyl carbonate, di-p-tolyl carbonate, phenyl-p-tolyl carbonate, di-p-chlorophenyl carbonate, dinaphthyl carbonate, and the like. These compounds can be used singly or in combination of two or more.
• the reaction is usually carried out at a temperature in the range of 150 to 350°C, preferably 200 to 300°C. Phenols derived from are distilled out of the system.
• the reaction time depends on the reaction temperature, degree of pressure reduction, etc., but is usually about 1 to 24 hours.
• the reaction is preferably carried out under an inert gas atmosphere such as nitrogen or argon.
• Aliphatic dicarboxylic acid components monocyclic aromatic dicarboxylic acid components such as phthalic acid, isophthalic acid and terephthalic acid, 2,7-naphthalenedicarboxylic acid, 2,3-naphthalenedicarboxylic acid, 1,4-naphthalenedicarboxylic acid, 1 , polycyclic aromatic dicarboxylic acid components such as 8-naphthalenedicarboxylic acid, anthracenedicarboxylic acid and phenanthenedicarboxylic acid; biphenyldicarboxylic acid components such as 2,2′-biphenyldicarboxylic acid; 1,4-cyclodicarboxylic acid; Examples include alicyclic dicarboxylic acid components such as 6-decalinedicarboxylic acid.
• Acid chlorides and esters may also be used as these derivatives.
• a monocyclic aromatic dicarboxylic acid component, a polycyclic aromatic dicarboxylic acid component, and a biphenyldicarboxylic acid component are preferred because they tend to increase heat resistance and refractive index.
• polyester resins include aliphatic diol components such as ethylene glycol, propanediol, butanediol, pentanediol, hexanediol, heptanediol, octanediol, nonanediol, etc.
• 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 at usually 120 to 350°C, preferably 150 to 300°C. .
• the degree of pressure reduction is changed step by step until finally 0.13 kPa or less to distill off the produced water or alcohol from the system, and the reaction time is usually about 1 to 10 hours.
• a polyester carbonate resin can be produced by a conventional method.
• the polyester carbonate resin used in the thermoplastic resin composition of the present invention is a phosgene method in which a dicarboxylic acid and a diol compound are added to an esterification reaction or a transesterification reaction, and a dicarboxylic acid chloride or phosgene is reacted, or a diol, a dicarboxylic acid and It can be produced by combining a transesterification method in which biaryl carbonate is reacted.
• the esterification reaction and transesterification reaction, and the phosgene method and transesterification method are as described above.
• Phosphite antioxidants such as 2-ethylhexyldiphenylphosphite, isodecyldiphenylphosphite, triisodecylphosphite, triphenylphosphite, 3,9-bis(octadecyloxy)-2,4,8,10- Tetraoxy-3,9-diphosphaspiro[5.5]undecane, 3,9-bis(2,6-di-tert-butyl-4-methylphenoxy)-2,4,8,10-tetraoxa- 3,9-diphosphaspiro[5.5]undecane, 2,2′-methylenebis(4,6-di-tert-butylphenyl) 2-ethylhexylphosphite, tris(2,4-ditert-butylphenyl ) phosphite, tris(nonylphenyl)phosphite, tetra-C12-15-alky
• the content of the antioxidant in the thermoplastic resin composition is preferably 0.01% by mass to 1% by mass based on the total mass of the resin composition.
• the content of the antioxidant in the thermoplastic resin composition is more preferably 0.05% by mass to 0.5% by mass, and particularly preferably 0.08% by mass to 0.3% by mass.
• the release agent is preferably contained in an amount of 0.01% by mass to 1% by mass based on the total mass of the resin composition.
• the content of the release agent in the thermoplastic resin composition is more preferably 0.05% by mass to 0.5% by mass, and particularly preferably 0.08% by mass to 0.3% by mass.
• thermoplastic resin composition The method for producing the thermoplastic resin composition is not particularly limited, and it can be produced by a known method.
• a method of making a thermoplastic resin composition includes mixing a thermoplastic resin and an ingredient. A step of mixing at least one of a solvent and an additive may be further included.
• the resin composition can be produced by adding compounding agents and additives sequentially or simultaneously to a thermoplastic resin and mixing them.
• the mixing step can be carried out by a conventional method, for example, a method of kneading with an extruder, or a method of dissolving the thermoplastic resin and the compounding agent in a solvent (e.g., methylene chloride, THF, etc.) to form a solution and then forming a solution.
• a solvent e.g., methylene chloride, THF, etc.
• an optical member containing the thermoplastic resin composition of the present invention is produced by injection molding, it is preferable to perform molding under the conditions of a cylinder temperature of 260 to 350°C and a mold temperature of 90 to 170°C. More preferably, molding is carried out 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 color, and if it is lower than 260°C, the melt viscosity will be high and molding will be difficult. Moreover, when the mold temperature is higher than 170° C., it tends to be difficult to remove the molded piece made of the resin composition from the mold.
• the mold temperature is less 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, or the mold applied to the mold will not be sufficiently transferred. It is easy to become difficult.
• Tg ⁇ Glass transition temperature (Tg, unit: ° C.)> The Tg of the thermoplastic resin composition was measured using the following equipment and conditions. Differential thermal scanning calorimeter: DSC, "DSC7000X” manufactured by Hitachi High-Tech Science Co., Ltd. Measurement method: JIS K7211 Measurement conditions: sample amount of 5 mg, nitrogen gas atmosphere, temperature increase condition of 10 ° C./min
• thermoplastic resin composition ⁇ Mold contamination> Using an injection molding machine (“SE7MII” manufactured by Sumitomo Heavy Industries, Ltd.), the pellets of the obtained thermoplastic resin composition were molded at a cylinder temperature of 280 ° C., a mold shape of a drop shape, and a mold temperature of 80 ° C. After 500 shots were molded under the conditions, the state of adhesion to the mold was visually evaluated according to the following criteria. A: Few deposits observed B: Deposits observed C: Many deposits observed
• Thermoplastic resin S-3000 Iupilon (registered trademark) S-3000 manufactured by Mitsubishi Engineering-Plastics Co., Ltd. was used. This resin was a bisphenol A-type aromatic polycarbonate resin produced by an interfacial polymerization method and represented by the following structural formula.
• the set n number of this resin represented by the following structural formula was 25.
• the resulting polycarbonate resin had an intrinsic viscosity of 0.291 dl/g and a viscosity average molecular weight (Mv) of 13,000.
• PTBP p-tert-butylphenol
• the set n number of the obtained oligomer was 3.
• the resulting oligomer had an intrinsic viscosity of 0.068 dl/g and a viscosity average molecular weight (Mv) of 3,700.
• BNE 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene
• 65.12 g (0.3042 mol) of DPC mol) and 2.21 ⁇ 10 ⁇ 4 g (2.63 ⁇ 10 ⁇ 6 mol) of sodium bicarbonate were placed in a 500 ml reactor equipped with a stirrer and distiller, and after nitrogen substitution, a nitrogen atmosphere of 760 Torr was introduced. Then, the mixture was heated to 205° C. over 1 hour and stirred.
• the resulting carbonate oligomer had an average number of repeating units of 3 as determined by mass spectrometry by electrolytic desorption mass spectrometry (FD-MS), and a mass average molecular weight of 1,400 as determined by GPC. That is, the obtained carbonate oligomer was subjected to mass spectrometry, and the average number of repeating units was calculated to be 3 by dividing the mass number by the BNE monomer unit molecular weight.
• FD-MS electrolytic desorption mass spectrometry
• the resin composition of the present invention is a thermoplastic resin composition excellent in the effect of reducing birefringence without impairing the properties of the optical resin composition.
• optical members such as optical lenses and optical films can be precisely molded from this resin composition.

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• Polymers & Plastics (AREA)
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• 2022
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