Classifications

• • G—PHYSICS
  • G02—OPTICS
  • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
  • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
  • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
• • G—PHYSICS
  • G02—OPTICS
  • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
  • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
  • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
  • G02B1/041—Lenses
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
  • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
  • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
  • C08G63/16—Dicarboxylic acids and dihydroxy compounds
  • C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
  • C08G63/19—Hydroxy compounds containing aromatic rings
  • C08G63/193—Hydroxy compounds containing aromatic rings containing two or more aromatic rings
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
  • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
  • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
  • C08G63/16—Dicarboxylic acids and dihydroxy compounds
  • C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
  • C08G63/19—Hydroxy compounds containing aromatic rings
  • C08G63/193—Hydroxy compounds containing aromatic rings containing two or more aromatic rings
  • C08G63/197—Hydroxy compounds containing aromatic rings containing two or more aromatic rings containing condensed aromatic rings
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
  • C08G63/64—Polyesters containing both carboxylic ester groups and carbonate groups
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
  • C08G64/04—Aromatic polycarbonates
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
  • C08G64/04—Aromatic polycarbonates
  • C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
  • C08G64/16—Aliphatic-aromatic or araliphatic polycarbonates
  • C08G64/1608—Aliphatic-aromatic or araliphatic polycarbonates saturated
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
  • C08G64/20—General preparatory processes
  • C08G64/30—General preparatory processes using carbonates
  • C08G64/307—General preparatory processes using carbonates and phenols

Definitions

• the present invention relates to an optical lens containing a thermoplastic resin. More particularly, the present invention relates to optical lenses comprising polycarbonate resin.
• 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.
• 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.
• Patent Documents 1 to 5 When optical resins are used as optical lenses, heat resistance, transparency, low water absorption, chemical resistance, low birefringence, resistance to moist heat, etc. are required in addition to optical properties such as refractive index and Abbe number. Especially in recent years, there has been a demand for optical lenses having a high refractive index and high heat resistance, and various resins have been developed (Patent Documents 1 to 5).
• thermoplastic resins made from 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene have excellent optical properties and are useful as various optical materials (Patent Document 6. ).
• Patent Document 6. thermoplastic resins made from 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene have excellent optical properties and are useful as various optical materials.
• An object of the present invention is to provide an optical lens using a thermoplastic resin that is excellent in optical properties such as refractive index and Abbe number, and is also excellent in mass change rate and dimensional change rate.
• the present inventors have found that by blending a specific amount of a diol compound having a specific structure, optical properties such as refractive index and Abbe number are excellent, and mass The inventors have found that it is possible to obtain an optical lens containing a thermoplastic resin which is excellent in rate of change and rate of dimensional change, and have completed the present invention.
• thermoplastic resin containing a structural unit (A) derived from a monomer represented by the following general formula (1) and a structural unit (B) derived from BPEF or BPPEF represented by the following structural formula an optical lens,
• the optical lens wherein the molar ratio (A:B) of the structural unit (A) and the structural unit (B) is 5:95 to 79:21.
• each of R 1 to R 4 is independently a hydrogen atom, a halogen atom, an optionally branched alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or a carbon represents an aryl group of numbers 6 to 15.
• the thermoplastic resin further contains a structural unit (C) derived from BCFL represented by the following structural formula.
• the structural unit (A) accounts for 5 to 50 mol % of all structural units in the thermoplastic resin.
• thermoplastic resin has a Tg of 120°C to 160°C.
• thermoplastic resin has a refractive index (nD) of 1.600 to 1.660.
• thermoplastic resin has an Abbe number of 21.0 to 27.0.
• thermoplastic resin has a mass change rate of 0.47% or less.
• thermoplastic resin has a dimensional change rate of 0.060% or less.
• an optical lens containing a thermoplastic resin that is excellent in optical properties such as refractive index and Abbe number, and also excellent in mass change rate and dimensional change rate.
• the optical lens of the present invention comprises a monomer-derived structural unit (A) represented by the following general formula (1), and BPEF (9,9-bis[4-(2-hydroxyethoxy)) represented by the following structural formula. phenyl]fluorene) or BPPEF (9,9-bis[4-(2-hydroxyethoxy)-3-phenylphenyl]fluorene).
• R 1 to R 4 are each independently a hydrogen atom, a halogen atom, or a branched group having 1 to 10 carbon atoms (preferably 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms).
• R 1 to R 4 more preferably each independently represent a hydrogen atom, a methyl group, or a phenyl group.
• the monomer represented by the general formula (1) is BPM (1,3-bis[2-(4-hydroxyphenyl)-2-propyl]benzene) represented by the following structural formula. is particularly preferred. This compound is also called bisphenol-M.
• the molar ratio (A:B) between the structural unit (A) and the structural unit (B) is 5:95 to 79:21, preferably 8:92 to 77:23. , more preferably 10:90 to 70:30.
• BPEF and BPPEF may be commercially available products or synthesized products.
• thermoplastic resin further contains a structural unit (C) derived from BCFL (biscresol fluorene) represented by the following structural formula.
• BCFL biscresol fluorene
• the proportion of the structural unit (A) in all structural units in the thermoplastic resin is 5 to 50 mol%, more preferably 8 to 48 mol%, and the structural unit
• the ratio of (B) is 11 to 95 mol%, more preferably 14 to 92 mol%
• the ratio of the structural unit (C) is 0 to 50 mol%, more preferably 0 to 38. in mol %.
• thermoplastic resin used in the optical lens of the present invention is not particularly limited and may be polyester resin, polycarbonate resin, polyester carbonate resin, epoxy resin, polyurethane resin, polyacrylic acid ester resin, polymethacrylic acid ester resin, or the like. , polyester resin or polyester carbonate resin, and more preferably polycarbonate resin.
• the total ratio of structural units (A), (B) and (C) to all structural units in the thermoplastic resin is 80 to 100 mol% of all structural units. It is preferably 90 to 100 mol %, particularly preferably 100 mol %. That is, the thermoplastic resin used in the present invention, in addition to the structural units (A) to (C), is generally used as a structural unit of a polycarbonate resin or a polyester carbonate resin within a range that does not impair the effects of the present invention. It can contain a structural unit derived from an aliphatic dihydroxy compound and a structural unit derived from an aromatic dihydroxy compound.
• various aliphatic dihydroxy compounds can be mentioned, and in particular, 1,4-cyclohexanedimethanol, tricyclodecanedimethanol, 1,3-adamantanedimethanol, 2,2-bis( 4-hydroxycyclohexyl)-propane, 3,9-bis(2-hydroxy-1,1-dimethylethyl)-2,4,8,10-tetraoxaspiro[5.5]undecane, 2-(5-ethyl -5-hydroxymethyl-1,3-dioxan-2-yl)-2-methylpropan-1-ol, isosorbide, 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol, etc.
• aromatic dihydroxy compounds can be mentioned, but in particular 2,2-bis(4-hydroxyphenyl)propane [bisphenol A], bis(4-hydroxyphenyl)methane, 1,1-bis( 4-hydroxyphenyl)ethane, 2,2-bis(4-hydroxy-3,5-dimethylphenyl)propane, 4,4'-dihydroxydiphenyl, bis(4-hydroxyphenyl)cycloalkane, bis(4-hydroxyphenyl) ) oxide, bis(4-hydroxyphenyl) sulfide, bis(4-hydroxyphenyl) sulfone, bis(4-hydroxyphenyl) sulfoxide, and bis(4-hydroxyphenyl) ketone, bisphenoxyethanol fluorene, and the like.
• bisphenol A 2,2-bis(4-hydroxyphenyl)propane
• 1,1-bis( 4-hydroxyphenyl)ethane 1,1-bis( 4-hydroxyphenyl)ethane
• the thermoplastic resin also preferably contains structural units derived from at least one monomer selected from the following monomer group.
• R 1 and R 2 each independently represent a hydrogen atom, a methyl group or an ethyl group
• R 3 and R 4 each independently represent a hydrogen atom, a methyl group, an ethyl group or a represents an alkylene glycol of ⁇ 5.
• the polycarbonate resin of a preferred embodiment of the present invention contains alcohol-based compounds such as phenol-based compounds that may be produced as by-products during production, and diol components or carbonic acid diesters that remain unreacted as impurities.
• Alcoholic compounds such as phenolic compounds and carbonic acid diesters, which are impurities, can cause a decrease in strength and generation of odor when formed into a molded article.
• the content of the remaining phenolic compound is preferably 3000 mass ppm or less, more preferably 1000 mass ppm or less, and particularly preferably 300 mass ppm or less based on 100 mass% of the polycarbonate resin.
• the content of the remaining diol component is preferably 1000 mass ppm or less, more preferably 100 mass ppm or less, and particularly preferably 10 mass ppm or less based on 100 mass% of the polycarbonate resin.
• the content of the remaining carbonic acid diester is preferably 1000 mass ppm or less, more preferably 100 mass ppm or less, and particularly preferably 10 mass ppm or less based on 100 mass% of the polycarbonate resin.
• it is preferable that the content of compounds such as phenol and t-butylphenol is small, and that the content of these compounds is within the above range.
• the content of the phenolic compound remaining in the polycarbonate resin can be measured by a method of analyzing the phenolic compound extracted from the polycarbonate resin using gas chromatography.
• the content of the alcohol-based compound remaining in the polycarbonate resin can also be measured by a method of analyzing the alcohol-based compound extracted from the polycarbonate resin using gas chromatography.
• the contents of diol components and carbonic acid diesters remaining in the polycarbonate resin can also be measured by extracting these compounds from the polycarbonate resin and analyzing them using gas chromatography.
• by-product alcoholic compounds such as phenolic compounds, diol components, and carbonic acid diesters may be reduced to the extent that they are not detected. good too. Moreover, if the amount is very small, the plasticity can be improved when the resin is melted.
• each of the remaining phenolic compound, diol component, or diester carbonate is, for example, 0.01 mass ppm or more, 0.1 mass ppm or more, or 1 mass ppm or more with respect to 100 mass% of the polycarbonate resin.
• the content of the remaining alcohol compound may be, for example, 0.01 mass ppm or more, 0.1 mass ppm or more, or 1 mass ppm or more with respect to 100 mass% of the polycarbonate resin.
• by-product alcohol compounds such as phenolic compounds, diol components, and carbonic acid diesters in the polycarbonate resin are adjusted so as to fall within the above ranges by appropriately adjusting the polycondensation conditions and equipment settings. It is possible. It can also be adjusted by the conditions of the extrusion process after polycondensation.
• the residual amount of by-product alcoholic compounds such as phenolic compounds is related to the type of diester carbonate used in the polymerization of the polycarbonate resin, the polymerization reaction temperature, the polymerization pressure, and the like. By adjusting these, the residual amount of by-product alcoholic compounds such as phenolic compounds can be reduced.
• the content of the remaining by-product alcohol compound in the obtained polycarbonate resin is preferably 3000 mass ppm or less with respect to the polycarbonate resin (100 mass %).
• the content of the remaining alcohol-based compound is preferably 3000 mass ppm or less, more preferably 1000 mass ppm or less, and particularly preferably 300 mass ppm or less based on 100 mass% of the polycarbonate resin.
• a preferred embodiment of the polycarbonate resin of the present invention can be produced in the presence of a basic compound catalyst, a transesterification catalyst, or a mixed catalyst consisting of both as a polycondensation catalyst.
• Examples of basic compound catalysts include alkali metal compounds, alkaline earth metal compounds, and nitrogen-containing compounds.
• alkali metal compounds include organic acid salts, inorganic salts, oxides, hydroxides, hydrides and alkoxides of alkali metals.
• alkaline earth metal compounds include organic acid salts, inorganic salts, oxides, hydroxides, hydrides and alkoxides of alkaline earth metal compounds.
• magnesium hydroxide, calcium acetate, strontium acetate, barium acetate, magnesium stearate, calcium stearate, calcium benzoate, magnesium phenylphosphate and the like are used.
• nitrogen-containing compounds include quaternary ammonium hydroxides and salts thereof, amines, and the like.
• quaternary ammonium hydroxides having an alkyl or aryl group such as tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, trimethylbenzylammonium hydroxide, triethylamine , dimethylbenzylamine, tertiary amines such as triphenylamine, secondary amines such as diethylamine and dibutylamine, primary amines such as propylamine and butylamine, 2-methylimidazole, 2-phenylimidazole, benzimidazole, etc.
• bases or basic salts such as ammonia, tetramethylammonium borohydride, tetrabutylammonium borohydride, tetrabutylammonium tetraphenylborate and tetraphenylammonium tetraphenylborate.
• Salts of zinc, tin, zirconium, and lead are preferably used as transesterification catalysts, and these can be used alone or in combination. It may also be used in combination with the alkali metal compound or alkaline earth metal compound described above.
• transesterification catalysts include zinc acetate, zinc benzoate, zinc 2-ethylhexanoate, tin (II) chloride, tin (IV) chloride, tin acetate (II), tin acetate (IV), and dibutyltin.
• Dilaurate, dibutyltin oxide, dibutyltin dimethoxide, zirconium acetylacetonate, zirconium oxyacetate, zirconium tetrabutoxide, lead acetate (II), lead acetate (IV) and the like are used.
• These catalysts are preferably used in a ratio of 1 ⁇ 10 ⁇ 9 to 1 ⁇ 10 ⁇ 3 mol, more preferably 1 ⁇ 10 ⁇ 7 to 1 ⁇ 10 ⁇ 4 mol, per 1 mol of the total diol compound. Used in molar proportions.
• thermoplastic resin ⁇ Physical properties of thermoplastic resin> (1) Refractive index (nD)
• one of the characteristics of the thermoplastic resin is that it has a high refractive index. is more preferable.
• the refractive index can be measured by the method described in Examples below.
• the Abbe number of the thermoplastic resin is preferably 21.0 to 27.0, more preferably 22.0 to 26.5.
• the Abbe number can be measured by the method described in Examples below.
• one of the characteristics of the thermoplastic resin is high heat resistance, and the glass transition temperature (Tg) is preferably 120 to 160 ° C., preferably 125 to 155 ° C. It is more preferable to have In the present invention, the glass transition temperature can be measured by the method described in Examples below.
• the polystyrene equivalent weight average molecular weight of the thermoplastic resin is preferably 10,000 to 100,000, more preferably 20,000 to 70,000, 30,000 to 60,000 is particularly preferred.
• one of the characteristics of the thermoplastic resin is that it has a low mass change rate, and the mass change rate is preferably 0.47% or less, and is 0.43% or less. is more preferable. Although the lower limit is not particularly limited, it is about 0.20%. In the present invention, the mass change rate can be measured by the method described in Examples below.
• one of the characteristics of the thermoplastic resin is that it has a low dimensional change rate, and the dimensional change rate is preferably 0.060% or less, and is 0.050% or less. is more preferable. Although the lower limit is not particularly limited, it is about 0.010%. In the present invention, the dimensional change rate can be measured by the method described in Examples below.
• the optical lens of the present invention may contain a thermoplastic resin composition containing the thermoplastic resin and additives described above.
• the thermoplastic resin composition of the present embodiment contains the above-described structural units (A) and (B), or the structural units (A), (B) and ( A resin other than the thermoplastic resin containing C) can be used in combination.
• Such resins include, but are not limited to, polycarbonate resins, polyester resins, polyester carbonate resins, (meth)acrylic resins, polyamide resins, polystyrene resins, cycloolefin resins, acrylonitrile-butadiene-styrene copolymer resins, chloride At least one resin selected from the group consisting of vinyl resins, polyphenylene ether resins, polysulfone resins, polyacetal resins and methyl methacrylate-styrene copolymer resins can be used. Various known ones can be used as these, and they can be added to the thermoplastic resin composition singly or in combination of two or more.
• the thermoplastic resin composition preferably contains an antioxidant as the additive.
• an antioxidant it is preferable to contain at least one of a phenolic antioxidant and a phosphite antioxidant.
• phenolic antioxidants 1,3,5-tris(3,5-di-tert-butyl-4-hydroxyphenylmethyl)-2,4,6-trimethylbenzene, 1,3,5-tris(3 ,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5-triazine e-2,4,6(1H,3H,5H)-trione, 4,4′,4′′-(1 -methylpropanyl-3-ylidene)tris(6-tert-butyl-m-cresol), 6,6'-di-tert-butyl-4,4'-butylidenedi-m-cresol, ocladecyl 3-(3, 5-di-tert-butyl-4-hydroxyphenyl)propionate, pentaery
• 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 antioxidant is preferably contained in an amount of 1 ppm to 3000 ppm by weight based on the total weight of the resin composition.
• the content of the antioxidant in the thermoplastic resin composition is more preferably 50 ppm to 2500 ppm by weight, more preferably 100 ppm to 2000 ppm by weight, and particularly preferably 150 ppm to 1500 ppm by weight. and more preferably 200 ppm to 1200 ppm by weight.
• the thermoplastic resin composition preferably contains a release agent as the additive.
• release agents include ester compounds such as glycerin fatty acid esters such as mono- and diglycerides of glycerin fatty acid, glycol fatty acid esters such as propylene glycol fatty acid esters and sorbitan fatty acid esters, higher alcohol fatty acid esters, aliphatic polyhydric alcohols and aliphatic carboxylic acids. Full esters with acids, mono fatty acid esters, and the like can be mentioned.
• ester of an aliphatic polyhydric alcohol and an aliphatic carboxylic acid is used as the release agent, either a monoester, a full ester, or the like can be used.
• release agents include the following. Namely, sorbitan fatty acid esters such as sorbitan stearate, sorbitan laurate, sorbitan oleate, sorbitan trioleate, sorbitan tribehenate, sorbitan stearate, sorbitan tristearate, sorbitan caprylate; Propylene glycol fatty acid esters such as propylene glycol monostearate, propylene glycol monooleate, propylene glycol monobehenate, propylene glycol monolaurate, and propylene glycol monopalmitate; Higher alcohol fatty acid esters such as stearyl stearate; Glycerin monostearate, glycerin mono-12-hydroxystearate, etc.
• sorbitan fatty acid esters such as sorbitan stearate, sorbitan laurate, sorbitan oleate, sorbitan trioleate, sorbitan tribehenate, sorbitan stea
• the release agent is preferably contained in an amount of 1 ppm to 5000 ppm by weight based on the total weight of the resin composition.
• the content of the release agent in the thermoplastic resin composition is more preferably 50 wt ppm to 4000 wt ppm, still more preferably 100 wt ppm to 3500 wt ppm, and particularly preferably 500 wt ppm to 13000 wt ppm. and more preferably 1000 ppm to 2500 ppm by weight.
• additives may be added to the thermoplastic resin composition in addition to the antioxidant and release agent described above.
• additives that may be contained in the thermoplastic resin composition include compounding agents, catalyst deactivators, heat stabilizers, plasticizers, fillers, ultraviolet absorbers, rust inhibitors, dispersants, antifoaming agents, leveling agents, Examples include flame retardants, lubricants, dyes, pigments, bluing agents, nucleating agents, and clarifying agents.
• the content of additives other than antioxidants and release agents in the thermoplastic resin composition is preferably 10 wt ppm to 5.0 wt %, more preferably 100 wt ppm to 2.0 wt %. and more preferably 1000 ppm by weight to 1.0% by weight, but not limited thereto.
• the above additives may adversely affect the transmittance and should not be added in excess, eg the total amount added is within the above range.
• the catalyst may be removed or deactivated in order to maintain thermal stability and hydrolytic stability after the completion of the polymerization reaction, but it is not necessarily deactivated. no need to let When deactivating, the known method for deactivating the catalyst by adding an acidic substance can be suitably carried out.
• acidic substances include esters such as butyl benzoate; aromatic sulfonic acids such as p-toluenesulfonic acid; aromatic sulfonate esters such as butyl p-toluenesulfonate and hexyl p-toluenesulfonate.
• Phosphoric acid phosphoric acid, phosphoric acid such as phosphonic acid
• triphenyl phosphite monophenyl phosphite, diphenyl phosphite, diethyl phosphite, di-n-propyl phosphite, di Phosphites such as n-butyl, di-n-hexyl phosphite, dioctyl phosphite, monooctyl phosphite
• Phosphonic acid esters such as dioctyl and monooctyl phosphate
• Phosphonic acids such as diphenylphosphonic acid, dioctylphosphonic acid and dibutylphosphonic acid
• Phosphonic acid esters such as diethyl phenylphosphonate
• P-toluene or butyl sulfonate is particularly preferred from the viewpoint of the effect of the deactivator, the stability to the resin, and the like.
• These deactivators are used in an amount of 0.01 to 50 times mol, preferably 0.3 to 20 times mol, relative to the catalyst amount. If it is less than 0.01 times the molar amount of the catalyst, the deactivation effect becomes insufficient, which is not preferable. On the other hand, when the amount is more than 50 times the molar amount of the catalyst, the heat resistance of the resin is lowered, and the molded article tends to be colored, which is not preferable.
• the deactivator may be kneaded immediately after completion of the polymerization reaction, or may be kneaded after pelletizing the polymerized resin. In addition to the deactivator, other additives can also be added by the same method.
• the optical lens of the present invention contains the above-described thermoplastic resin or thermoplastic resin composition (hereinafter simply abbreviated as "resin composition").
• resin composition thermoplastic resin or thermoplastic resin composition
• the mold temperature when the mold temperature is higher than 200° C., it tends to be difficult to take out the molded piece made of the resin composition from the mold. On the other hand, if 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.
• the optical lens manufactured using the above resin composition has a high refractive index and excellent heat resistance, so it can be used in fields such as telescopes, binoculars, television projectors, etc., where expensive high-refractive index glass lenses have conventionally been used. can be used and is extremely useful.
• R 1 and R 2 each independently represent a hydrogen atom, a methyl group or an ethyl group
• R 3 and R 4 each independently represent a hydrogen atom, a methyl group, an ethyl group or a represents an alkylene glycol of ⁇ 5.
• a lens molded from a resin containing a structural unit derived from any of the monomers of the above formulas can be superimposed and used as a lens unit.
• the optical lens of the present invention is preferably implemented in the form of an aspherical lens if necessary.
• Aspherical lenses can eliminate spherical aberration with a single lens, so there is no need to combine multiple spherical lenses to remove spherical aberration, which helps reduce weight and molding costs. be possible. Therefore, aspherical lenses are particularly useful as camera lenses among optical lenses.
• the optical lens of the present invention is particularly useful as a material for thin, compact, and complicated-shaped optical lenses because of its high molding fluidity.
• the thickness of the central portion is preferably 0.05 to 3.0 mm, more preferably 0.05 to 2.0 mm, still more preferably 0.1 to 2.0 mm.
• the diameter is preferably 1.0 mm to 20.0 mm, more preferably 1.0 to 10.0 mm, still more preferably 3.0 to 10.0 mm.
• the lens is a meniscus lens having a convex surface on one side and a concave surface on the other side.
• the optical lens of the present invention can be molded by any method such as mold molding, cutting, polishing, laser processing, electrical discharge machining, and etching. Among these, mold molding is more preferable from the viewpoint of manufacturing cost.
• refractive index (nD) Based on JIS B 7071-2: 2018, polycarbonate resin was molded to obtain a V block and used as a test piece. It was measured at 23°C with the following refractometer. Refractive index meter: Shimadzu KPR-3000
• Mass change rate (%) (M1-M0)/M0 x 100
• M1 Mass of test piece after storage for 72 hours at temperature of 85°C and humidity of 85%
• M0 Mass of test piece before storage at temperature of 85°C and humidity of 85% for 72 hours
• Example 1 As raw materials, 8000 g (18.24 mol) of 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene (BPEF) represented by the following structural formula, 1,3-bis 550 g (1.59 mol) of [2-(4-hydroxyphenyl)-2-propyl]benzene (BPM), 4375 g (20.42 mol) of diphenyl carbonate (DPC) and 0.10 mol/liter of sodium hydrogen carbonate 1.2 ml of aqueous solution (2.2 ⁇ 10 ⁇ 4 mol, i.e.
• BPEF 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene
• the obtained resin was dried at 100°C for 12 hours or more with an ADVANTEC blower constant temperature dryer DRM420DD, and then with a FANUC injection molding machine S-2000i30A at a cylinder temperature of 260°C and a mold temperature of 10°C lower than the glass transition temperature of the resin. Injection molded as temperature to obtain lenses with a diameter of 5 mm.
• Examples 2 to 7, Comparative Examples 1 to 5 A polycarbonate resin was obtained in the same manner as in Example 1, except that the raw materials shown in Table 2 below were used. The evaluation results of the obtained resin are shown in Table 1 below. Incidentally, in Comparative Examples 2 to 4, Tg was low and the mass change rate and dimensional change rate could not be measured.

Landscapes

• Chemical & Material Sciences (AREA)
• Health & Medical Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Organic Chemistry (AREA)
• Physics & Mathematics (AREA)
• General Physics & Mathematics (AREA)
• Optics & Photonics (AREA)
• Polyesters Or Polycarbonates (AREA)
• Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Priority Applications (5)

Applications Claiming Priority (2)

Publications (1)

Family

ID=86612090

Family Applications (1)

Country Status (7)

Citations (11)

Family Cites Families (3)

• 2022
  • 2022-11-28 KR KR1020247006133A patent/KR20240108368A/ko active Pending
  • 2022-11-28 WO PCT/JP2022/043650 patent/WO2023100778A1/ja not_active Ceased
  • 2022-11-28 US US18/709,191 patent/US20250110258A1/en active Pending
  • 2022-11-28 TW TW111145398A patent/TW202336083A/zh unknown
  • 2022-11-28 CN CN202280077964.9A patent/CN118382822A/zh active Pending
  • 2022-11-28 JP JP2023564944A patent/JPWO2023100778A1/ja active Pending
  • 2022-11-28 EP EP22901211.7A patent/EP4443199A4/en active Pending

Patent Citations (11)

Non-Patent Citations (1)

Also Published As

Similar Documents

Legal Events