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WO2018216897A2 - Composition de résine pour lentille optique à indice de réfraction moyen à base d'acryle époxy et son procédé de préparation - Google Patents

Composition de résine pour lentille optique à indice de réfraction moyen à base d'acryle époxy et son procédé de préparation Download PDF

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Publication number
WO2018216897A2
WO2018216897A2 PCT/KR2018/003996 KR2018003996W WO2018216897A2 WO 2018216897 A2 WO2018216897 A2 WO 2018216897A2 KR 2018003996 W KR2018003996 W KR 2018003996W WO 2018216897 A2 WO2018216897 A2 WO 2018216897A2
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WIPO (PCT)
Prior art keywords
phosphite
epoxy
weight
resin composition
optical lens
Prior art date
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Ceased
Application number
PCT/KR2018/003996
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English (en)
Korean (ko)
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WO2018216897A3 (fr
Inventor
장동규
노수균
홍길표
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KOC Solution Co Ltd
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KOC Solution Co Ltd
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Priority to CN201880033188.6A priority Critical patent/CN110637060A/zh
Publication of WO2018216897A2 publication Critical patent/WO2018216897A2/fr
Publication of WO2018216897A3 publication Critical patent/WO2018216897A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • C08L33/062—Copolymers with monomers not covered by C08L33/06
    • C08L33/068—Copolymers with monomers not covered by C08L33/06 containing glycidyl groups
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
    • B29D11/00—Producing optical elements, e.g. lenses or prisms
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
    • B29D11/00—Producing optical elements, e.g. lenses or prisms
    • B29D11/00009—Production of simple or compound lenses
    • 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
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
    • C08K5/5313—Phosphinic compounds, e.g. R2=P(:O)OR'
    • 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
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
    • C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
    • C08K5/5333—Esters of phosphonic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • 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

Definitions

  • the present invention relates to an epoxy acrylic optical lens, and more particularly, to a resin composition for an epoxy acrylic medium refractive optical lens having excellent releasability, thermal stability, compressive strength, transparency, and color of a refractive index of 1.53 to 1.58, and a method of manufacturing the same.
  • Lenses made of PMMA (polymethyl-methacrylate), an acrylic resin introduced in 1936, are also called acrylic lenses and have a high transparency with Abbe number 57, but have a low refractive index of 1.49 and heat resistance compared to CR-39 with similar refractive index. And there is a disadvantage of low surface strength.
  • PMMA polymethyl-methacrylate
  • acrylic resin introduced in 1936
  • Japan's DISO Co., Ltd. developed acrylic high refractive resin for the first time in 1992 by mixing a reactive diluent such as styrene with dibromobisphenol A diacrylate. It didn't work.
  • Japanese Patent Laid-Open Nos. Hei 6-49133 and Hei 7-206974 have suggested a method of manufacturing a lens by mixing divinylbenzene, styrene, benzyl methacrylate, isocyanate and the like with tetrabromobisphenol A diacrylate. These optical lenses have improved light resistance and heat resistance, but have low thermal stability, causing color change during hard coating.
  • Korean Patent Publication No. 10-2004-0083942 discloses thermal stability and light resistance of spectacle lenses by mixing a reactive diluent such as styrene and methyl styrene to tetrabromobisphenol A diacrylate and adding an acidic phosphate ester thereto.
  • the lens of the refractive index 1.58-1.61 is greatly improved.
  • Such an epoxy acrylic lens has advantages of high refractive index and high Abbe's number, excellent optical properties such as transparency, light weight, and heat resistance, and low cost of materials.
  • reactive diluents are needed to control the viscosity and reaction rate.
  • Such reactive diluents are conventionally styrene, divinylbenzene, alphamethylstyrene, alphamethylstyrenedimer, benzyl methacrylate, chlorostyrene, bromostyrene, Toxy styrene, dibenzyl maleate, etc. are used individually or in mixture of 2 or more types.
  • the choice of diluent affects the productivity and optical properties of the lens and also the production cost. For example, styrene, which is frequently contained at present and in a high content in the resin, causes a decrease in strength.
  • optical resins such as polyethylene glycol bisallylcarbonate, polymethyl methacrylate, diallyl phthalate, polystyrene, and polycarbonate are conventionally used as optical lenses in the medium refractive index range.
  • Japanese Patent Laid-Open No. 53-7787 provides an optical lens in which 85% by weight of diallyl isophthalate and 15% by weight of diethylene glycol bisallylcarbonate are polymerized. In the case of this lens, the lens has been successfully thinned. There is still a problem of weak impact resistance.
  • Republic of Korea Patent Publication 10-0431434 discloses a monomer composition for a medium refractive lens in the range of 1.53 ⁇ 1.55, consisting of diallyl ester oligomer, dialkyl maleate, diethylene glycol bisallylcarbonate and diallyl adipate. This has improved properties in light stability and impact resistance compared to the existing mid-refractive lens, but has a problem of low transparency and low heat resistance with Abbe's number.
  • Patent Document 1 Japanese Laid-Open Patent Digestion 53-7787
  • Patent Document 2 Japanese Patent Laid-Open No. 62-235901
  • Patent Document 3 Japanese Patent Laid-Open No. 64-45412
  • Patent Document 4 Japanese Patent Publication No. 1-60494
  • Patent Document 5 European Patent 06905
  • Patent Document 6 Republic of Korea Patent Publication 10-0431434
  • Patent Document 7 Republic of Korea Patent Registration 10-0496911
  • Patent Document 8 Republic of Korea Patent Registration 10-0498896
  • Patent Document 9 Republic of Korea Patent Publication 10-2015-0071170
  • the problem of release, thermal stability and light resistance which are often unknown cause is related to the content of the epoxy group-containing compound remaining in the manufacturing process of the epoxy acrylate It aims to clarify and solve this problem.
  • Methyl methacrylate is conventionally used as a reactive diluent together with styrene, divinylbenzene, alphamethylstyrene, and alphamethylstyrene dimer, but when used in more than 20% by weight of resin, there are problems in physical properties in many aspects such as whitening and polymerization imbalance. It is only used in small quantities. However, when the methyl methacrylate is used in a large amount, the compressive strength is improved as compared with the case of using styrene, and thus the compressive strength can be improved without the addition of the production cost.
  • the transparency, Abbe number, thermal stability, light resistance and release properties are all excellent, excellent in compressive strength and economical resin composition for epoxy acrylic mid-refraction optical lens It aims to provide.
  • the resin composition for the epoxy acrylic mid-refraction optical lens may further comprise an internal release agent in 0.001 to 10% by weight of the composition.
  • the resin composition for the epoxy acrylic medium refractive optical lens may further comprise a heat stabilizer in 0.01 to 5% by weight of the composition.
  • An epoxy acrylic medium refractive optical lens having a solid-state refractive index of 1.53 to 1.58 obtained by polymerizing a resin composition for an optical lens containing 1 to 17 wt% of a reactive diluent in a mold is provided.
  • an acrylic mesopore optical lens comprising the step of polymerizing the resin composition for epoxy acrylic mesopore optical lens into a mold.
  • the compressive strength is greatly improved at low production costs in the medium refractive lens of the solid-state refractive index of 1.53 ⁇ 1.58, release properties, thermal stability, light resistance,
  • the transparency and Abbe's number also provide the resin composition for epoxy-acrylic medium refractive optical lenses.
  • BPDA Bisphenol A epoxy acrylate
  • MMA Methylmethacrylate
  • the bisphenol A epoxy acrylate is usually obtained by reacting bisphenol A diglycidyl ether represented by the following formula (2) with acrylic acid, which is contained in bisphenol A epoxy acrylate in which an epoxy group-containing compound is prepared by unreacted and side reactions. Can be.
  • the inventors have found that the problem of releasability, thermal stability and light resistance, which are often unknown when manufacturing an epoxy acrylate-based lens, is caused by the content of the epoxy group-containing compound remaining in the manufacturing process of bisphenol A epoxy acrylate. I found a relationship.
  • the preferable content of the epoxy group containing compound contained in bisphenol A epoxy acrylate is 0.7 weight% or less, More preferably, it is 0.01 to 0.6 weight%.
  • an 'epoxy group-containing compound' is defined as a compound including one or more epoxy groups in the compound, including a compound represented by the following Chemical Formulas 2-3.
  • the epoxy group-containing compound particularly preferably includes a compound represented by the following Chemical Formulas 2 to 3.
  • the epoxy group-containing compound in bisphenol A epoxy acrylate can be controlled by controlling the equivalent of acrylic acid. Specifically, after 18 hours after the progress of the synthesis reaction of bisphenol A epoxy acrylate, the reaction sample in the reaction is taken, and the epoxy content in the sample is measured to calculate the epoxy content remaining in the reactant as an equivalent.
  • the epoxy group-containing compound in the bisphenol A epoxy acrylate may be less than 0.01% by weight, but considering the lens quality and production cost, the preferred content of the epoxy group-containing compound is 0.01 to 0.6% by weight, more preferably 0.01 to 0.55% by weight.
  • the content of the epoxy group-containing compound in bisphenol A epoxy acrylate is measured by the following method.
  • the bisphenol A epoxy acrylate (BPDA) is contained in the resin composition for epoxy acrylic mid-refraction optical lens of the present invention 50 to 70% by weight, preferably 55 to 65% by weight.
  • Methyl methacrylate (MMA) included in the resin composition of the present invention has been used as a reactive diluent in conventional epoxy acrylic optical resins together with styrene, divinylbenzene, alphamethylstyrene, and alphamethylstyrene dimer.
  • MMA is not included in a large amount and is usually used in a small amount of 3% or less but less than 20%. This is because when MMA is contained in an optical lens resin of 20% by weight or more, there are problems in the physical properties of the lens in various aspects such as whitening and polymerization imbalance.
  • MMA in the resin composition of the present invention is preferably included in 21 to 45% by weight, more preferably may be included in 25 to 40% by weight.
  • the reactive diluent included in the resin composition of the present invention serves to appropriately control the viscosity and polymerization rate of the composition, and can be used as long as it is used as a reactive diluent in the resin for epoxy acrylic optical lens, and is not particularly limited. .
  • the reactive diluent is styrene, divinylbenzene, alphamethylstyrene, alphamethylstyrene dimer, benzyl methacrylate, chlorostyrene, bromostyrene, methoxystyrene, monobenzylmaleate, monobenzyl fumalate, di Benzyl maleate, dibenzyl fumarate, methyl benzyl maleate, dimethyl maleate, diethyl maleate, dibutyl maleate, dibutyl fumarate, monobutyl maleate, monopentyl maleate, dipentyl maleate, monopentyl fumal
  • the reactive diluent is one or two or more compounds selected from the group consisting of styrene, divinylbenzene, alphamethylstyrene, alphamethylstyrene dimer, benzyl methacrylate, chlorostyrene, bromostyrene, methoxystyrene
  • MMA which is essentially included in the resin composition of the present invention, serves as a reactive diluent
  • other reactive diluents are contained in a small amount of 1 to 17% by weight. If the total content of reactive diluents including MMA and other reactive diluents exceeds 60% by weight, the viscosity of the composition may be too low to melt the tape adhesive, which may lead to tape bleaching and leakage during curing after injection. As a result, whitening and stria may occur in the lens.
  • the resin composition of the present invention comprising MMA and a reactive diluent has a liquid viscosity of 20-200 cps at 25 ° C., suitable for template polymerization, and a liquid refractive index (nD, 20 ° C.) of the resin composition is 1.48-1.55, and solid phase refractive index (nE). , 20 ° C.) is 1.53-1.58. If the viscosity of the liquid is less than 20 cps, the composition flows out of the mold when the liquid resin composition is injected into a glass mold assembled with a synthetic resin gasket or adhesive tape, and the composition flows out of the mold if the viscosity of the liquid exceeds 200 cps. There is a problem that is difficult to inject. More preferable viscosity is 30-100 cps.
  • the resin composition of the present invention may further include an internal mold release agent.
  • an internal mold release agent By adding an internal mold release agent in a resin composition before mold polymerization, mold release property after superposition
  • the internal mold release agent may preferably be included in an amount of 0.001 to 10% by weight in the polymerizable composition.
  • a phosphate ester compound As an internal mold release agent, a phosphate ester compound, a silicone type surfactant, a fluorine type surfactant, an alkyl quaternary ammonium salt, etc. can be used individually or in combination of 2 or more types, respectively.
  • Fluorine-based nonionic surfactants are compounds having a perfluoroalkyl group in the molecule, such as Eudin DS-401 TM (Japan, Daishin Industrial Co., Ltd.), Unidin DS-403 TM (Japan, Daikin Industrial Co., Ltd.), Eftop EF. 122A TM (Japan, Shin-Avada Chemical Co., Ltd.), Effope EF 126 TM (Japan, Shin-Avada Chemical Co., Ltd.), and Eftop EF 301 TM (Japan, Shin-Avada Chemical Co., Ltd.).
  • Silicone-based nonionic surfactants are compounds having a dimethylpolysiloxane group in a molecule, such as Q2-120A TM of Dow, USA.
  • Alkyl quaternary ammonium salts are commonly known as cationic surfactants, and include halogen salts, phosphates, sulfates, and the like.
  • double chloride salts include trimethylcetyl ammonium chloride, trimethyl stearyl ammonium chloride, dimethylethylcetyl ammonium chloride, and triethyl. Decylammonium chloride, trioctylmethyl ammonium chloride, decylammonium chloride and the like.
  • a phosphate ester compound can be used as an internal mold release agent.
  • the phosphate ester compound is a compound having a phosphate ester group, and is, for example, isopropyl acid phosphate, diisopropyl acid phosphate, butylic acid phosphate, dibutyl phosphate, octylic acid phosphate, dioctyl acid phosphate, isodecyl acid phosphate or diisode.
  • polyoxyethylene nonylphenol ether phosphate 5% by weight of 5 mole of ethylene oxide added, 80% by weight of 4 mole added, 10% by weight of 3 mole added, 1 mole added
  • polyoxyethylenenonylphenyl phosphate 5% by weight of 9 mol of ethylene oxide added, 80% by weight of 8 mol of ethylene oxide, 10% by weight of 7 mol of ethylene oxide, ethylene 5% by weight of oxide added up to 6 mol
  • polyoxyethylenenonylphenol ether phosphate 3% by weight of 11 moles of ethylene oxide added, 80% by weight of 10 moles added, 5% by weight of 9 moles added, 7 mole added 6% by weight, 6 mole added 6% by weight
  • polyoxyethylene nonylphenol ether phosphate 13 mole added by ethylene oxide 3% by weight, 12 mole added by 80% by weight, 11 mole added 8% by weight, 9% by weight added 3% by weight,
  • the resin composition of the present invention may further include a heat stabilizer.
  • Heat stabilizer Preferably it may be included in 0.01 to 5.00% by weight in the resin composition of the present invention.
  • the thermal stabilizer is used at less than 0.01% by weight, the thermal stability effect is weak.
  • the thermal stabilizer is used at more than 5.00%, the polymerization failure rate during curing may be high and the thermal stability of the cured product may be lowered.
  • thermal stabilizer examples include calcium stearate, barium stearate, zinc stearate, cadmium stearate, lead stearate, magnesium stearate, aluminum stearate, potassium stearate and zinc octoate, which are metal fatty acid salts.
  • One or two or more compounds selected from the compounds can be used.
  • triphenyl phosphite diphenyldecyl phosphite, phenyldidecyl phosphite, diphenyldodecyl phosphite, diphenylisodecyl phosphate, trinolylphenyl phosphite, diphenylisooctyl phosphite, tri
  • One or two or more compounds selected from butyl phosphite, tripropyl phosphite, triethyl phosphite, trimethyl phosphite, tris (monodecyl phosphite) and tris (monophenyl) phosphite can be used.
  • diphenylisodecyl phosphate can be used.
  • organotin-based dibutyltin diaurate dibutyltin maleate, dibutyltin bis (isooctyl maleate), dioctyl maleate, dibutyltin bis (monomethyl maleate), dibutyltin bis (la Uryl mercaptide), dibutyl bis (isooxyl mercaptoacetate), monobutyl tin tris (isooctyl mercapto acetate), dimethyl tin bis (isooctyl mercapto acetate), tris (isooctyl mercapto acetate), fertility Tiltin bis (isooctyl mercaptoacetate), dibutyl tin bis (2-mercapto ethyl laurate), monobutyl tin tris (2- mercapto ethyl laurate), dimethyl tin bis (2- mercapto ethylate)
  • the thermal stability of the optical lens can be greatly improved without deteriorating not only the initial color of the molded lens but also optical properties such as transparency, impact strength, heat resistance, and polymerization yield.
  • the resin composition of the present invention may further include ultraviolet absorbers, organic dyes, inorganic pigments, anti-colorants, antioxidants, light stabilizers, catalysts, and the like, in addition to conventional techniques in the field of plastic optical lenses.
  • the epoxy acrylic mid-refraction optical lens according to the present invention can be produced by putting the resin composition of the present invention into a mold and polymerizing the same. According to a preferred embodiment, after injecting the resin composition into the mold, the mold is placed in a forced circulation oven and gradually heat-cured from 30 °C to 120 °C, and then cooled to 70 ⁇ 10 °C to remove the mold to obtain a lens.
  • all raw materials are preferably high purity compounds with a purity of 70-99.99%.
  • the purity of all raw materials is checked to purify low purity compounds and use high purity compounds without purification.
  • the acryl-based medium refractive optical lens obtained by the above manufacturing method may be used in various fields as a medium refractive lens having a solid-state refractive index of 1.53-1.58, replacing the existing medium refractive lens. Specifically, it can be used as a plastic glasses lens, a 3D polarizing lens equipped with a polarizing film on the spectacle lens, a camera lens, etc. In addition to a variety of optical, such as recording media substrates, color filters and ultraviolet absorption filters used in prisms, optical fibers, optical disks, etc. Can be used in the product.
  • Refractive index and Abbe number It was measured using an Abbe refractometer, a DR-M4 model of Atago.
  • the epoxy acrylic resin composition was thermally cured when the optical lens was manufactured, and was marked with “ ⁇ ” and “ ⁇ ” according to breakage of the lens or mold when the optical lens and the mold were separated when demolded at 70 ° C.
  • ⁇ means that the lens or mold is not broken at all or one is broken during the separation of 100 optical lenses and the mold.
  • ⁇ means that 2 or 3 lenses or molds are removed during the separation of the 100 optical lenses and the mold.
  • "x" indicates that 4 or more lenses or molds are broken during separation of 100 optical lenses and molds.
  • Example 1 In the same manner as in Example 1 , an optical lens was manufactured according to the composition shown in Table 1 , and experiments were conducted to measure the physical properties thereof. The results are shown in Table 1 below.
  • An optical lens was manufactured according to the composition described in the same manner as in Comparative Example 1 , the physical properties thereof were measured, and the results are shown in Table 1 .
  • 4- PENPP polyoxyethylene nonylphenyl phosphate (5% by weight of 5 mol of ethylene oxide added, 80% by weight of 4 mol of ethylene oxide added, 10% by weight of 3 mol of ethylene oxide added, ethylene oxide 1 mole added 5% by weight)
  • 8- PENPP polyoxyethylene nonylphenyl phosphate (5% by weight of 9 mol of ethylene oxide added, 80% by weight of 8 mol of ethylene oxide added, 10% by weight of 7 mol of ethylene oxide added, ethylene oxide 5% by weight of 6 mol or less)
  • V65 2,2'-azobis (2,4-dimethylbarrenonitrile) (2,2'-azobis (2,4-dimethylvaleronitrile)
  • Epoxy acryl-based medium refractive optical lens with high compressive strength can also be manufactured at low production cost.
  • the optical lens according to the present invention can be widely used in the related art by replacing the existing medium refractive lens. In particular, it can be used in the field of plastic glasses, 3D polarizing lens with polarizing film on the spectacle lens, camera lens, and various optical products such as recording media substrates, coloring filters and ultraviolet absorbing filters used for prism, optical fiber, optical disk, etc. It can be used to.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Manufacturing & Machinery (AREA)
  • Ophthalmology & Optometry (AREA)
  • Mechanical Engineering (AREA)
  • Epoxy Resins (AREA)

Abstract

La présente invention concerne une lentille optique à base d'acryle époxy et, en particulier, une composition de résine pour une lentille optique à indice de réfraction moyen à base d'acryle époxy ayant une aptitude au moulage, une stabilité thermique, une résistance à la lumière et une résistance à la compression favorables, avec un indice de réfraction à l'état solide s'inscrivant dans une plage de 1,53 à 1,58, et son procédé de préparation. La présente invention concerne une composition de résine pour une lentille optique à indice de réfraction moyen à base d'acryle époxy ayant un indice de réfraction à l'état solide s'inscrivant dans la plage de 1,53 à 1,58, la composition de résine contenant : de 50 à 70 % en poids d'époxyacrylate de bisphénol A ayant une teneur en composé contenant un groupe époxy inférieure ou égale à 0,7 % en poids, de 21 à 45 % en poids de méthacrylate de méthyle et de 1 à 17 % en poids d'un diluant réactif. Selon la présente invention, il est possible de produire à un faible coût de production une lentille optique à indice de réfraction moyen à base d'acryle époxy ayant d'excellentes aptitude au moulage, stabilité thermique et résistance à la lumière ainsi qu'une haute résistance à la compression, tout en maintenant la transparence et le nombre d'Abbe à de bons niveaux, par une maîtrise de la teneur du composé contenant un groupe époxy restant pendant la procédure de préparation de l'acryle époxy et par calcul de la composition de sorte qu'elle contienne une grande quantité de MMA. La lentille optique à indice de réfraction moyen à base d'acryle époxy selon la présente invention peut être largement utilisée dans divers domaines par remplacement d'une lentille optique à indice de réfraction moyen existante.
PCT/KR2018/003996 2017-05-23 2018-04-05 Composition de résine pour lentille optique à indice de réfraction moyen à base d'acryle époxy et son procédé de préparation Ceased WO2018216897A2 (fr)

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KR1020170063689A KR20180128296A (ko) 2017-05-23 2017-05-23 에폭시 아크릴계 중굴절 광학렌즈용 수지 조성물 및 그 제조방법

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Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS537787A (en) * 1976-07-12 1978-01-24 Toho Rayon Co Ltd Copolymers for use in lenses and their preparation
JPS5824101A (ja) * 1981-08-06 1983-02-14 Osaka Soda Co Ltd 光学用樹脂組成物
JPS62235901A (ja) * 1986-04-07 1987-10-16 Nippon Oil & Fats Co Ltd 合成樹脂製レンズ用組成物ならびに製造方法
JPS6445412A (en) * 1987-08-14 1989-02-17 Seiko Epson Corp Composition for lens made of synthetic polymer
JPH0649133A (ja) * 1992-08-04 1994-02-22 Daiso Co Ltd 重合性組成物およびそれより得られる高屈折率プラスチックレンズ
JPH06211960A (ja) * 1993-01-14 1994-08-02 Daiso Co Ltd 重合性組成物およびそれより得られる高屈折率プラスチックレンズ
JPH07206974A (ja) * 1994-01-11 1995-08-08 Daiso Co Ltd 重合性組成物およびそれより得られる高屈折率プラスチックレンズ
JPH07247331A (ja) * 1994-03-11 1995-09-26 Nippon Kayaku Co Ltd 樹脂組成物、光学材料用樹脂組成物及びその硬化物
KR20000058427A (ko) * 2000-05-22 2000-10-05 한정민 광학용 주형 성형 모노머
KR100496911B1 (ko) * 2000-11-07 2005-06-23 장동규 광학용 수지조성물
KR100474586B1 (ko) * 2002-06-12 2005-03-08 주식회사 두산 수지 조성물 및 그에 의해 제조된 광학 렌즈
KR100523083B1 (ko) * 2003-01-14 2005-10-20 주식회사 니드필 저비중, 중굴절률 광학 렌즈용 수지 조성물 및 그를이용하여 제조한 광학렌즈
KR100498896B1 (ko) * 2003-03-25 2005-07-04 장동규 에폭시 아크릴레이트를 주성분으로 하는 고굴절 광학 렌즈용 수지 조성물
CN101592860B (zh) * 2004-10-07 2012-04-04 日立化成工业株式会社 光学材料用树脂组合物、光学材料用树脂薄膜及使用其的光导
WO2008068205A1 (fr) * 2006-12-07 2008-06-12 Basf Se Compositions de résine époxy et leur procédé de fabrication
WO2013187539A1 (fr) * 2012-06-13 2013-12-19 주식회사 케이오씨솔루션 Procédé de polymérisation d'une coulée de résine destinée à être utilisée comme verre optique acrylique époxy et composition de résine contenant un agent de démoulage interne destinée à être utilisée comme verre optique acrylique époxy
CN104812834B (zh) * 2012-11-13 2017-04-26 可奥熙搜路司有限公司 环氧丙烯酸类的高折射光学材料用聚合性组合物及环氧丙烯酸类高折射光学材料的制备方法
KR102117129B1 (ko) * 2013-12-18 2020-06-02 주식회사 케이오씨솔루션 에폭시 아크릴계 중굴절 광학렌즈용 수지 조성물 및 그 제조방법
KR101816969B1 (ko) * 2014-12-29 2018-01-09 주식회사 엘지화학 광학시트
KR101816722B1 (ko) * 2017-04-21 2018-01-11 주식회사 케이오씨솔루션 에폭시 아크릴계 중굴절 광학렌즈용 수지 조성물 및 그 제조방법

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