JP5286624B2 - Method for manufacturing optical plastic article for infrared communication - Google Patents

Description

The present invention relates to a method of manufacturing an optical plastic article for infrared communication used for infrared communication and control ports of various electronic devices.

An infrared communication system using infrared rays is generally used in various electronic devices such as personal computers, PDAs (Personal Digital Assistants) and portable information terminals such as electronic notebooks, digital cameras, and cellular phones. A device capable of infrared communication is equipped with a predetermined (for example, IrDA standard) infrared communication port. In order to prevent malfunctions due to disturbance light of the light receiving element that is sensitive to visible light in the window part of such an infrared communication port, only infrared is used as a light receiving part for infrared communication in order to prevent the inside of the device from being seen. A transparent dark plastic plate is arranged.
However, the infrared communication light receiving unit using such a plate has a black appearance color, and therefore may not match the entire device or a component to be combined due to the design of the electronic device. There was a problem. Although it is possible in principle to color the appearance of the infrared communication light-receiving part in any color by adding a colorant to the transparent plastic substrate or painting, it is possible to maintain transparency in the infrared region. It is extremely difficult to adjust the appearance color to various colors.
Therefore, the applicant has developed a light receiving part for infrared communication having a dielectric multilayer film that transmits infrared light on a substrate as disclosed in Patent Document 1. In such infrared communication light receiving parts, it is possible to design various appearance colors using dielectric multilayer films while maintaining infrared transparency, providing electronic devices with an increased degree of design freedom I was able to do that.
However, although the infrared light receiving part using a dielectric multilayer film as disclosed in Patent Document 1 has a much higher degree of freedom in design than the conventional case where a dark plastic plate is used, the dielectric multilayer is improved. Since a metal color is inevitably accompanied when a film is colored, for example, this patent document does not necessarily apply to a white system (which is of course not necessarily limited to a white system) as the color of a housing of a device. In some cases, the light-receiving part 1 does not fit as a design. For this reason, in particular, a white light receiving part for infrared communication has been demanded from a request for further design freedom.

JP 2006-165493 A

Since white means that external light is diffusely reflected, for example, even if a white pigment is applied to the substrate, the wavelength range of the visible light range to the infrared communication band is scattered almost over the entire area. Therefore, it was not possible to transmit only the wavelength range of the required infrared communication band. Further, even if a thin color such as frosted glass that allows transmission through the wavelength band of the infrared communication band is applied, the visible light range is received and there is a risk of malfunction of the device due to ambient light. In addition, when the white coloring is not sufficient, there is a possibility that an unfavorable state may occur in terms of design in which the inside of the device can be seen through.
Therefore, the applicant has proposed the prior invention of Japanese Patent Application No. 2009-066556 prior to the present application. The invention of the same prior application is capable of transmitting a large number of wavelengths in the infrared communication band, and is an optical article for infrared communication and a light receiving section for infrared communication that visually reflects and reflects light in the visible light range to give white. It is invention regarding.
In the invention of the prior application, a method of adding a metal oxide fine particle to give a white color was adopted. However, when metal oxide fine particles are used, the smaller the metal oxide fine particles, the easier it is to aggregate, and even though a smaller primary particle size is selected, the actual particle size (secondary particle size) may increase. In some cases, the variation in the particle diameter may increase. Therefore, an optical plastic article for infrared communication that can transmit a large number of wavelengths in the infrared communication band without using metal oxide fine particles, and that also visually scatters and reflects light in the visible light range and exhibits white color. Was demanded.
The present invention is an improved invention of the above-mentioned prior application, and its object is to have good dispersibility of fine particles, and stably scatter-reflect light in the visible light region and exhibit white color for infrared communication. The object is to provide a method of manufacturing an optical plastic article.

In order to achieve the above object, in the invention described in claim 1, as a method for producing an optical plastic article for infrared communication, the weight average molecular weight is greater than 1,000 and greater than 500,000 in a urethane or allyl monomer. The following small vinyl copolymer (C) is added and stirred or heated or photocured to disperse the vinyl copolymer (C) in the cured product of the monomer to form microphase-separated fine particles. The gist of this is to do this.
(1) 5 to 45% by weight of a vinyl monomer (A) having a SP value of less than 3 and a molecular weight of 180 or more, compared to the SP value of the cured product of the urethane-based or allyl-based monomer,
(2) Vinyl copolymer weight obtained by copolymerizing 10 to 95% by weight of a vinyl monomer (B) having a SP value of 3 or more with respect to the SP value of the cured product of the urethane or allyl monomer. Combined (C)
Further, in the invention according to claim 2, in addition to the constitution of the invention according to claim 1, the vinyl copolymer (C) contains a vinyl monomer other than the vinyl monomers (A) and (B) as a copolymerization component. The gist is to contain 0 to 85% by weight.
Further, in the invention according to claim 3, in addition to the constitution of the invention according to claim 1 or 2, fine particles derived from the vinyl copolymer (C) dispersed in a cured product of the urethane-based or allyl-based monomer. The gist of this is that the average particle size is 0.05 μm or more.

  In the present invention, a urethane-based or allyl-based monomer and the following vinyl copolymer (C) are added, and the vinyl copolymer (C) is dispersed in a cured product of the monomer by stirring and heating or photocuring. The present invention provides an optical plastic article for infrared communication that exhibits white by forming fine particles having a microphase separation structure.

The vinyl copolymer (C) has a SP value of less than 3 and a molecular weight of 180 or more with respect to the SP value of the cured product of these monomers, which is a component compatible with the cured product of the urethane or allyl monomer. The vinyl monomer (B) having an SP value of 3 or more is different from the SP value of the cured product of the urethane-based or allyl-based monomer, which is a component incompatible with the cured product of the vinyl monomer (A). Consists of
As shown in FIG. 1, the fine particles of vinyl copolymer (C) formed in the cured product of urethane-based or allyl-based monomer are contained in the vinyl monomer (B) component due to the effect of SP value. And the outside of the particle is formed by the component of the vinyl monomer (A). The vinyl monomer (B) forms an interface with a cured product (dispersion medium) of a urethane or allyl monomer as an incompatible site. On the other hand, the vinyl monomer (A), which is a compatible site, is compatible with a cured product of a urethane-based or allyl-based monomer and becomes a skeleton that stably holds particles in a dispersion medium.
When the skeleton of the vinyl copolymer (C) is formed, the vinyl monomer (A) side having a small difference with respect to the SP value of the cured product of the urethane or allyl monomer is coordinated to the outside. The large vinyl monomer (B) side is coordinated inside.
The fine particles of vinyl copolymer (C) are cured of urethane or allyl monomers because the outer part of the particles composed of monomer (A) is compatible with the cured product of urethane or allyl monomers. Fine particles are stably formed on the product, and a stable microphase separation structure is formed and exists in a dispersed state in the cured product of the monomer. Since the fine particles are phase-separated from the monomer cured product, irregular reflection occurs at the interface, and the microscopic appearance is as if the solid particles (for example, metal oxide fine particles) are dispersed in the monomer cured product. Become.
The “monomer” in the present invention is a substrate that serves as a reference material for polymerization, and is used in a concept that includes some low polymers such as oligomers.

In order to disperse fine particles having such a microphase separation structure as a dispersoid using a cured product of a urethane or allyl monomer as a dispersion medium, the vinyl monomer (A) and vinyl monomer (C) in the vinyl copolymer (C) ( The blending ratio of B) is a point.
In the present invention, the vinyl monomer (A) needs to contain 5 to 45% by weight of a monomer having a difference from an SP value of less than 3 and a molecular weight of 180 or more when a urethane or allyl monomer is cured.
This is because if the molecular weight is less than 180, fine particles cannot be stably present in the optical member, and the particles cause problems such as sedimentation and unevenness when the monomer is cured.
The reason why the content is 5% by weight or more is that when the monomer is less than 5% by weight, fine particles cannot exist stably when the monomer is cured, causing problems such as sedimentation and bias in the optical member. is there.
Further, the content is 45% by weight or less because if the content exceeds 45% by weight, the compatibility becomes too high and the vinyl copolymer C becomes an optical member regardless of the proportion of the vinyl monomer (B). This is because they are compatible with each other and fine particles cannot be formed.

On the other hand, the vinyl monomer (B) in the present invention has an SP value of 3 or more when the urethane or allyl monomer is cured, and needs to be contained in an amount of 10 to 95% by weight.
The reason why the content is set to 10% by weight or more is that if the content is less than 10% by weight, it is compatible with the cured product of the monomer and particles cannot be formed. The upper limit of the blending ratio of the vinyl monomer (B) is 95% by weight because the vinyl monomer (A) has a lower limit of 5% by weight. As can be seen from this weight distribution, when the vinyl monomer (A) is 5% by weight and the vinyl monomer (B) is 95% by weight, the vinyl copolymer (C) is composed only of the vinyl monomers (A) and (B). Polymerized. Moreover, since the minimum of the mixture ratio of a vinyl monomer (A) is 5 weight%, the minimum of the total mixture ratio of the vinyl monomer (A) (B) in a vinyl copolymer (C) will be 15 weight%. As described above, when the vinyl copolymer (C) is not 100% by weight only with the vinyl monomers (A) and (B), other vinyl monomers are blended (maximum 85% by weight) to be 100% by weight. There is a need to.
The vinyl monomer used in the present invention can be used as needed without any particular limitation in kind and number as long as it is selected from the calculated SP value and molecular weight.

  Furthermore, in the present invention, the vinyl copolymer (C) needs to have a weight average molecular weight of more than 1,000 and less than 500,000. When the molecular weight is 1,000 or less, the particles are miniaturized and sufficient white turbidity cannot be obtained. In addition, if the molecular weight is extremely large, the particles cannot be stably present due to sedimentation in the optical member. In order that the particles can be dispersed without settling, the weight average molecular weight needs to be less than 500,000.

Fine particles having a microphase separation structure can be produced with a particle size of about 0.01 to 100 μm. However, in order to obtain white or an arbitrary color optical article for infrared communication which is the gist of the present invention, the particle diameter is controlled to a certain size, and visually, light in the visible range is scattered to present white. Therefore, it is necessary to transmit only a large wavelength range of the infrared communication band.
The particle diameter for that purpose is preferably 0.05 to 10.0 μm. When the particle size is less than 0.05, the particle size is too small to scatter light in the visible range, and when the particle size is more than 10.0 μm, the fine particle density is such that a level of white that cannot transmit visible light is exhibited. As a transmission characteristic in this case, there is a problem that the transmittance of infrared rays is lowered. In other words, the smaller the particle size, the greater the transmittance in the infrared region (that is, the smaller the reflectance) compared to the visible region, but the larger the particle size than 10.0 μm, the both the infrared region and the visible region. This is because the transmittance (about 12%) necessary for this type of optical plastic article for infrared communication cannot be maintained when white is at a level where visible light cannot be transmitted.

The solubility parameter (SP value) is used as a value representing the polarity of the compound. When mixing two things, if the difference of SP value is small, it will be compatible, and if large, it will not be compatible.
In the present invention, a value derived by substituting the cohesive energy constant of each atomic group of Hoy into the Small calculation formula of the following formula 1 is applied.

Examples of vinyl monomers that can be used in the present invention include carboxylic acid-containing monomers such as αβ-unsaturated carboxylic acids such as acrylic acid, methacrylic acid, itaconic acid, fumaric acid, maleic acid,
Methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, -butyl (meth) acrylate, 2-ethylhexyl C1-C35 linear and branched alkyl vinyl monomers such as (meth) acrylate and n-octyl (meth) acrylate,
Aromatic vinyl such as phenyl (meth) acrylate, benzyl (meth) acrylate, styrene, α-methylstyrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, p-tert-butylstyrene, vinyltoluene monomer,
Cyclopentyl (meth) acrylate, cyclohexyl (meth) acrylate, cycloheptyl (meth) acrylate, cyclooctyl (meth) acrylate, adamantyl (meth) acrylate, isobornyl (meth) acrylate, methylcyclohexyl (meth) acrylate, ethylcyclohexyl (meth) Fats such as acrylate, methyladamantyl (meth) acrylate, 4-butylcyclohexyl (meth) acrylate, dihydrodicyclopentadienyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, tricyclodecanyl (meth) acrylate Vinyl monomers having a cyclic hydrocarbon substituent,
NN-dimethylaminoethyl (meth) acrylate, NN-diethylaminoethyl (meth) acrylate, NN-dimethylaminopropyl (meth) acrylate, NN-di-t-butylaminoethyl (meth) acrylate, NN-dimethylaminobutyl (meth) ) NN-dialkylaminoalkyl (meth) acrylate such as acrylate, NN-dimethylaminoethyl (meth) acrylamide, NN-diethylaminoethyl (meth) acrylamide, NN-dialkylaminoalkyl (NN) such as NN-dimethylaminopropyl (meth) acrylamide ( Amino group-containing vinyl monomers such as (meth) acrylamide,
Epoxy group-containing vinyl monomers such as glycidyl (meth) acrylate, 34-epoxycyclohexylmethyl (meth) acrylate,
Unsaturated carboxylic acid esters such as itaconic acid esters such as benzyl itaconic acid, maleic acid esters such as dimethyl maleate, fumaric acid esters such as dimethyl fumarate,
Vinyl monomers such as acrylonitrile, methacrylonitrile, vinyl acetate,
-Vinyl esters, each containing various (per) fluoroalkyl groups, such as perfluorocyclohexyl (meth) acrylate, di-perfluorocyclohexyl fumarate or N-isopropyl perfluorooctanesulfonamidoethyl (meth) acrylate, Various vinyl-containing monomers such as vinyl ethers,-(meth) acrylates or -unsaturated polycarboxylic acid esters,
Vinylethoxysilane, γ- (meth) acryloxypropyltrimethoxysilane, γ- (meth) acryloxypropyltriethoxysilane, γ- (meth) acryloxypropyltripropoxysilane, γ- (meth) acryloxypropylmethoxydimethoxy Silane, γ- (meth) acryloxypropylmethoxydiethoxysilane, γ- (meth) acryloxypropylmethoxydipropoxysilane, γ- (meth) acryloxybutylphenyldimethoxysilane, γ- (meth) acryloxybutylphenyldi Ethoxysilane, γ- (meth) acryloxybutylphenyl dipropoxysilane, γ- (meth) acryloxypropyldimethylmethoxysilane, γ- (meth) acryloxypropyldimethylethoxysilane, γ- (meth) acryloxypropyl dimethyl Such as Le ethoxysilane, various silane-based vinyl monomer,
And polyorganosiloxane-containing vinyl monomers such as polydimethylsiloxypropyl (meth) acrylate.

The copolymer (C) of the present invention is produced, for example, by heating and aging the above-mentioned various vinyl monomers, a non-reactive solvent and a polymerization initiator in a reaction vessel.
The non-reactive solvent is an aliphatic hydrocarbon solvent such as hexane, heptane or cyclohexane, an aromatic hydrocarbon solvent such as benzene, toluene or xylene, an ester solvent such as ethyl acetate or butyl acetate, methanol or butanol. Examples include alcohol solvents, aprotic polar solvents such as dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, pyridine, and ketone solvents such as acetone, methyl ethyl ketone, and methyl isobutyl ketone. These solvents can be used alone or in combination. .
As the polymerization initiator, known polymerization initiators that can be used in the polymerization reaction can be arbitrarily used. For example, azo compounds, peroxide compounds, sulfides, sulfines, sulfinic acids, diazo compounds, redox compounds Radical polymerization initiators such as

  The urethane-based monomer in the present invention is a raw material monomer of a urethane-based resin (including a thiourethane-based resin), and includes a polyisocyanate compound and a polythiol compound for generating a thiourethane-based resin or a urethane-based resin. Examples thereof include a combination, a combination of a polyisocyanate compound and a polyol compound, and a combination of a polyisocyanate compound and a thiol compound having a hydroxy group.

  As a polyisocyanate compound, a polyisocyanate compound having two or more isocyanate groups in one molecule, a polyisocyanate compound having two or more isocyanate groups in one molecule and containing a sulfur atom in the molecule, one molecule Examples thereof include polyiso (thio) cyanate compounds having two or more iso (thio) cyanate groups, but are not particularly limited thereto. Specifically, ethylene diisocyanate, trimethylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate, octamethylene diisocyanate, nonamethylene diisocyanate, 2,2′-dimethylpentane diisocyanate 2,2,4-trimethylhexane diisocyanate, decamethylene diisocyanate, butene diisocyanate, 1,3-butadiene-1,4-diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate 1,6,11-undecatriisocyanate, 1,3,6-hexamethylene triisocyanate, 1,8-diisocyanate-4-isocyanatomethyloctane, 2,5,7-trimethyl-1,8 -Diisocyanate-5-isocyanate methyl octa , Bis (isocyanate ethyl) carbonate, bis (isocyanate ethyl) ether, 1,4-butylene glycol dipropyl ether-w, w'-diisocyanate, lysine diisocyanate methyl ester, lysine triisocyanate, 2 -Isocyanatoethyl-2,6-diisocyanatohexanoate, 2-isocyanatopropyl-2,6-diisocyanatohexanoate, xylylene diisocyanate, bis (isocyanatoethyl) benzene, bis (isocyanate) Propyl) benzene, α, α, α ′, α′-tetramethylxylylene diisocyanate, bis (isocyanatobutyl) benzene, bis (isocyanatomethyl) naphthalene, bis (isocyanatomethyl) diphenyl ether, bis (isocyanate ethyl) ) Aliphatic polyisocyanates such as phthalate, mesityrylene triisocyanate, 2,6-di (isocyanatomethyl) furan; isophorone diisocyanate, bis (isocyanatomethyl) cyclohexane, dicyclohexylmethane diisocyanate, cyclohexane Diisocyanate, norbornene diisocyanate, methylcyclohexane diisocyanate, dicyclohexyldimethylmethane diisocyanate, 2,2′-dimethyldicyclohexylmethane diisocyanate, bis (4-isocyanate-n-butylidene) pentaerythritol, dimer acid Diisocyanate, 2-isocyanatomethyl-3- (3-isocyanatopropyl) -5-isocyanatomethyl-bicyclo- [2.2.1] -heptane, 2-isocyanate Tomethyl-3- (3-isocyanatopropyl) -6-isocyanatomethyl-bicyclo- [2.2.1] -heptane, 2-isocyanatomethyl-2- (3-isocyanatopropyl) -5-isocyanate Methyl-bicyclo- [2.2.1] -heptane, 2-isocyanatomethyl-2- (3-isocyanatopropyl) -6-isocyanatomethyl-bicyclo- [2.2.1] -heptane, 2- Isocyanatomethyl-3- (3-isocyanatopropyl) -5- (2-isocyanatoethyl) -bicyclo- [2.2.1] -heptane, 2-isocyanatomethyl-3- (3-isocyanatopropyl) ) -6- (2-isocyanatoethyl) -bicyclo- [2.2.1] -heptane, 2-isocyanatomethyl-2- (3-isocyana) Topropyl) -5- (2-isocyanatoethyl) -bicyclo- [2.2.1] -heptane, 2-isocyanatomethyl-2- (3-isocyanatopropyl) -6- (2-isocyanatoethyl) -Alicyclic polyisocyanates such as bicyclo- [2.2.1] -heptane; phenylene diisocyanate, tolylene diisocyanate, ethylphenylene diisocyanate, isopropylphenylene diisocyanate, dimethylphenylene diisocyanate, diethyl Phenylene diisocyanate, diisopropylphenylene diisocyanate, trimethylbenzene triisocyanate, benzene triisocyanate, naphthalene diisocyanate, methyl naphthalene diisocyanate, biphenyl diisocyanate, toluidine diisocyanate 4,4′-diphenylmethane diisocyanate, 3,3′-dimethyldiphenylmethane-4,4′-diisocyanate, bibenzyl-4,4′-diisocyanate, bis (isocyanatophenyl) ethylene, 3, 3′-dimethoxybiphenyl-4,4′-diisocyanate, triphenylmethane triisocyanate, polymeric MDI, naphthalene triisocyanate, diphenylmethane-2,4,4′-triisocyanate, 3-methyldiphenylmethane-4, 6,4′-triisocyanate, 4-methyl-diphenylmethane-3,5,2 ′, 4 ′, 6′-pentaisocyanate, phenylisocyanatemethylisocyanate, phenylisocyanateethylisocyanate, tetrahydronaphthylenediisocyanate Nate, hexahydrobenzene Diisocyanate, hexahydrodiphenylmethane-4,4'-diisocyanate, diphenyl ether diisocyanate, ethylene glycol diphenyl ether diisocyanate, 1,3-propylene glycol diphenyl ether diisocyanate, benzophenone diisocyanate, diethylene glycol diphenyl ether diisocyanate Aromatic polyisocyanates such as dibenzofurandiocyanate, carbazole diisocyanate, ethylcarbazole diisocyanate, dichlorocarbazole diisocyanate, etc .; thiodiethyl diisocyanate, thiodipropyl diisocyanate, thiodihexyl diisocyanate, Dimethyl sulfone diisocyanate, dithiodimethyl diisocyanate, dithiodiethyl diisocyanate Anato, sulfur-containing aliphatic polyisocyanates such as dithiodipropyl diisocyanate, diphenyl sulfide-2,4′-diisocyanate, diphenyl sulfide-4,4′-diisocyanate, 3,3′-dimethoxy-4 Aromatic sulfide isocyanates such as 4,4'-diisocyanate dibenzylthioether, bis (4-isocyanatomethylbenzene) sulfide, 4,4'-methoxybenzenethioethylene glycol-3,3'-diisocyanate; Diphenyl disulfide-4,4′-diisocyanate, 2,2′-dimethyldiphenyl disulfide-5,5′-diisocyanate, 3,3′-dimethyldiphenyl disulfide-5,5′-diisocyanate, 3, 3'-dimethyldiphenyl disulfide-6,6'-diisocyanate, 4,4 '-Dimethyldiphenyl disulfide-5,5'-diisocyanate, 3,3'-dimethoxydiphenyl disulfide-4,4'-diisocyanate, 4,4'-dimethoxydiphenyl disulfide-3,3'-diisocyanate Aromatic disulfide polyisocyanates such as: diphenylsulfone-4,4′-diisocyanate, diphenylsulfone-3,3′-diisocyanate, benzylidenesulfone-4,4′-diisocyanate, diphenylmethanesulfone-4 , 4′-diisocyanate, 4-methyldiphenylsulfone-2,4′-diisocyanate, 4,4′-dimethoxydiphenylsulfone-3,3′-diisocyanate, 3,3′-dimethoxy-4, 4′-diisocyanate dibenzylsulfone, 4,4′-dimethyldiphenylsulfone-3, 3′-diisocyanate, 4,4′-di-tert-butyldiphenylsulfone-3,3′-diisocyanate, 4,4′-methoxybenzeneethylenedisulfone-3,3′-diisocyanate, 4, Aromatic sulfone polyisocyanates such as 4'-dichlorodiphenylsulfone-3,3'-diisocyanate; 4-methyl-3-isocyanatobenzenesulfonyl-4'-isocyanate phenol ester, 4-methoxy-3- Sulfonic ester polyisocyanates such as isocyanate benzenesulfonyl-4'-isocyanate phenol ester; 4-methyl-3-isocyanatobenzenesulfonylanilide-3'-methyl-4'-isocyanate, dibenzenesulfonyl-ethylenediamine -4,4'-diisocyanate, 4,4'-meth Aromatic sulfonic acid amides such as xybenzenesulfonyl-ethylenediamine-3,3′-diisocyanate, 4-methyl-3-isocyanatobenzenesulfonylanilide-4-methyl-3′-isocyanate; thiophene-2,5- Examples thereof include sulfur-containing heterocyclic compounds such as diisocyanate, and other 1,4-dithian-2,5-diisocyanate, but are not particularly limited thereto. They may be used alone or in combination of two or more.

  Examples of the polythiol compound include a polythiol compound having two or more mercapto groups in one molecule, a polythiol compound having two or more mercapto groups in one molecule and a sulfur atom in the molecule, and the like. The invention is not particularly limited to this. Specifically, methanedithiol, 1,2-ethanedithiol, 1,1-propanedithiol, 1,2-propanedithiol, 1,3-propanedithiol, 2,2-propanedithiol, 1,6-hexanedithiol, 1,2,3-propanetrithiol, 1,1-cyclohexanedithiol, 1,2-cyclohexanedithiol, 2,2-dimethylpropane-1,3-dithiol, 3,4-dimethoxybutane-1,2-dithiol, 2-methylcyclohexane-2,3-dithiol, bicyclo [2,2,1] peptor exo-cis-2,3dithiol, 1,1-bis (mercaptomethyl) cyclohexane, bis-thiomalate (2-mercaptoethyl ester) 2,3-dimercaptosuccinic acid (2-mercaptoethyl ester), 2,3 Dimercapto-1-propanol (2-mercaptoacetate), 2,3-dimercapto-1-propanol (3-mercaptoacetate), diethylene glycol bis (2-mercaptoacetate), diethylene glycol bis (3-mercaptopropionate), 1, 2-dimercaptopropyl methyl ether, 2,3-dimercaptopropyl methyl ether, 2,2-bis (mercaptomethyl) -1,3-propanedithiol, bis (2-mercaptoethyl) ether, ethylene glycol bis (2- Mercaptoacetate), ethylene glycol bis (3-mercaptopropionate), trimethylolpropane bis (2-mercaptoacetate), trimethylolpropane bis (3-mercaptopropionate), pentaerythris Aliphatic polythiols such as tall tetrakis (2-mercaptoacetate) and pentaerythritol tetrakis (3-mercaptopropionate), and halogen-substituted compounds such as chlorine- and bromine-substituted compounds, 1,2-dimercaptobenzene, 1 , 3-dimercaptobenzene, 1,4-dimercaptobenzene, 1,2-bis (mercaptomethyl) benzene, 1,3-bis (mercaptomethyl) benzene, 1,4-bis (mercaptomethyl) benzene, 1, 2-bis (mercaptoethyl) benzene, 1,3-bis (mercaptoethyl) benzene, 1,4-bis (mercaptoethyl) benzene, 1,2-bis (mercaptomethyleneoxy) benzene, 1,3-bis (mercapto) Methyleneoxy) benzene, 1,4-bis (mercaptomethyleneoxy) B) benzene, 1,2-bis (mercaptoethyleneoxy) benzene, 1,3-bis (mercaptoethyleneoxy) benzene, 1,4-bis (mercaptoethyleneoxy) benzene, 1,2,3-trimercaptobenzene, 1,2,4-trimercaptobenzene, 1,3,5-trimercaptobenzene, 1,2,3-tris (mercaptomethyl) benzene, 1,2,4-tris (mercaptomethyl) benzene, 1,3,3 5-tris (mercaptomethyl) benzene, 1,2,3-tris (mercaptoethyl) benzene, 1,2,4-tris (mercaptoethyl) benzene, 1,3,5-tris (mercaptoethyl) benzene, 1, 2,3-tris (mercaptomethyleneoxy) benzene, 1,2,4-tris (mercaptomethyleneoxy) ben 1,3,5-tris (mercaptomethyleneoxy) benzene, 1,2,3-tris (mercaptoethyleneoxy) benzene, 1,2,4-tris (mercaptoethyleneoxy) benzene, 1,3,5- Tris (mercaptoethyleneoxy) benzene, 1,2,3,4-tetramercaptobenzene, 1,2,3,5-tetramercaptobenzene, 1,2,4,5-tetramercaptobenzene, 1,2,3 4-tetrakis (mercaptomethyl) benzene, 1,2,3,5-tetrakis (mercaptomethyl) benzene, 1,2,4,5-tetrakis (mercaptomethyl) benzene, 1,2,3,4-tetrakis (mercapto) Ethyl) benzene, 1,2,3,5-tetrakis (mercaptoethyl) benzene, 1,2,4,5-tetrakis (me Captoethyl) benzene, 1,2,3,4-tetrakis (mercaptomethyleneoxy) benzene, 1,2,3,5-tetrakis (mercaptomethyleneoxy) benzene, 1,2,4,5-tetrakis (mercaptomethyleneoxy) Benzene, 1,2,3,4-tetrakis (mercaptoethyleneoxy) benzene, 1,2,3,5-tetrakis (mercaptoethyleneoxy) benzene, 1,2,4,5-tetrakis (mercaptoethyleneoxy) benzene, 2,2′-dimercaptobiphenyl, 4,4′-dimercaptobiphenyl, 4,4′-dimercaptobibenzyl, 2,5-toluenedithiol, 3,4-toluenedithiol, 1,4-naphthalenedithiol, 1 , 5-Naphthalenedithiol, 2,6-naphthalenedithiol, 2,7-naphtha Range thiol, 2,4-dimethylbenzene-1,3-dithiol, 4,5-dimethylbenzene-1,3-dithiol, 9,10-anthracene dimethanethiol, 1,3-di (p-methoxyphenyl) propane Aromatic polythiols such as -2,2-dithiol, 1,3-diphenylpropane-2,2-dithiol, phenylmethane-1,1-dithiol, 2,4-di (p-mercaptophenyl) pentane, 5-dichlorobenzene-1,3-dithiol, 1,3-di (p-chlorophenyl) propane-2,2-dithiol, 3,4,5-tribromo-1,2-dimercaptobenzene, 2,3,4 Halogen-substituted aromatic polythiols such as chlorine-substituted products, bromine-substituted products such as 1,6-tetrachloro-1,5-bis (mercaptomethyl) benzene, 2-methylamino-4,6-dithiol-sym-triazine, 2-ethylamino-4,6-dithiol-sym-triazine, 2-amino-4,6-dithiol-sym-triazine, 2-morpholino-4,6- Dithiol-sym-triazine, 2-cyclohexylamino-4,6-dithiol-sym-triazine, 2-methoxy-4,6-dithiol-sym-triazine, 2-phenoxy-4,6-dithiol-sym-triazine, 2 -Polythiols containing heterocycles such as thiobenzeneoxy-4,6-dithiol-sym-triazine, 2-thiobutyloxy-4,6-dithiol-sym-triazine, and their chlorine- and bromine-substituted products Although a halogen substituted compound is mentioned, it is not specifically limited to this. Each of these may be used alone or in combination of two or more.

  Examples of the bifunctional or higher polythiol containing at least one sulfur atom in addition to the mercapto group include 1,2-bis (mercaptomethylthio) benzene, 1,3-bis (mercaptomethylthio) benzene, and 1,4-bis. (Mercaptomethylthio) benzene, 1,2-bis (mercaptoethylthio) benzene, 1,3-bis (mercaptoethylthio) benzene, 1,4-bis (mercaptoethylthio) benzene, 1,2,3-tris ( Mercaptomethylthio) benzene, 1,2,4-tris (mercaptomethylthio) benzene, 1,3,5-tris (mercaptomethylthio) benzene, 1,2,3-tris (mercaptoethylthio) benzene, 1,2,4 -Tris (mercaptoethylthio) benzene, 1,3,5-tris (mercaptoeth Thio) benzene, 1,2,3,4-tetrakis (mercaptomethylthio) benzene, 1,2,3,5-tetrakis (mercaptomethylthio) benzene, 1,2,4,5-tetrakis (mercaptomethylthio) benzene, 1 2,3,4-tetrakis (mercaptoethylthio) benzene, 1,2,3,5-tetrakis (mercaptoethylthio) benzene, 1,2,4,5-tetrakis (mercaptoethylthio) benzene, and the like Aromatic polythiol such as bis (mercaptomethyl) sulfide, bis (mercaptoethyl) sulfide, bis (mercaptopropyl) sulfide, bis (mercaptomethylthio) methane, bis (2-mercaptoethylthio) methane, bis ( 3-mercaptopropylthio) methane, 1,2- Sus (mercaptomethylthio) ethane, 1,2-bis (2-mercaptoethylthio) ethane, 1,2-bis (3-mercaptopropyl) ethane, 1,3-bis (mercaptomethylthio) propane, 1,3-bis (2-mercaptoethylthio) propane, 1,3-bis (3-mercaptopropylthio) propane, 1,2,3-tris (mercaptomethylthio) propane, 1,2,3-tris (2-mercaptoethylthio) Propane, 1,2,3-tris (3-mercaptopropylthio) propane, tetrakis (mercaptomethylthiomethyl) methane, tetrakis (2-mercaptoethylthiomethyl) methane, tetrakis (3-mercaptopropylthiomethyl) methane, bis ( 2,3-dimercaptopropyl) sulfide, 2,5-dimercapto- 1,4-dithiane, bis (mercaptomethyl) disulfide, bis (mercaptoethyl) disulfide, bis (mercaptopropyl) disulfide, and the like, esters of thioglycolic acid and mercaptopropionic acid, hydroxymethyl sulfide bis (2-mercaptoacetate ), Hydroxymethyl sulfide bis (3-mercaptopropionate), hydroxyethyl sulfide bis (2-mercaptoacetate), hydroxyethyl sulfide bis (3-mercaptopropionate), hydroxypropyl sulfide bis (2-mercaptoacetate), Hydroxypropyl sulfide bis (3-mercaptopropionate), hydroxymethyl disulfide bis (2-mercaptoacetate), hydroxymethyldisulfi Bis (3-mercaptopropionate), hydroxyethyl disulfide bis (2-mercaptoacetate), hydroxyethyl disulfide bis (3-mercaptopropionate), hydroxypropyl disulfide bis (2-mercaptoacetate), hydroxypropyl disulfide bis ( 3-mercaptopropionate), 2-mercaptoethyl ether bis (2-mercaptoacetate), 2-mercaptoethyl ether bis (3-mercaptopropionate), 1,4-dithiane, 2,5-diol bis (2- Mercaptoacetate), 1,4-dithian-2,5-diol bis (3-mercaptopropionate), thiodiglycolic acid bis (2-mercaptoethyl ester), thiodipropionic acid bis (2-mercaptoethyl) Ester), 4,4-thiodibutyric acid bis (2-mercaptoethyl ester), dithiodiglycolic acid bis (2-mercaptoethyl ester), dithiodipropionic acid bis (2-mercaptoethyl ester), 4,4-dithiodiphtylic acid Bis (2-mercaptoethyl ester), thiodiglycolic acid bis (2,3-dimercaptopropyl ester), thiodipropionic acid bis (2,3-dimercaptopropyl ester), dithioglycolic acid bis (2,3- Examples thereof include aliphatic polythiols such as dimethylcaptopropyl ester) and bis (2,3-dimercaptopropyl ester) dithiodipropionate, and heterocyclic compounds such as 3,4-thiophenedithiol and bismuthiol. Is not to be done. These may be used alone or in combination of two or more.

  Examples of the polyol compound include a polyol compound having two or more hydroxyl groups in one molecule, a polyol compound having two or more hydroxyl groups in one molecule and containing a sulfur atom in the molecule, and the like. The invention is not particularly limited to this. Specifically, ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, butylene glycol, neopentyl glycol, glycerin, trimethylolethane, trimethylolpropane, butanetriol, 1,2-methylglucoside, pentaerythritol, dipenta Erythritol, tripentaerythritol, sorbitol, erythritol, threitol, ribitol, arabinitol, xylitol, altol, mannitol, dolcitol, iditol, glycol, inositol, hexanetriol, triglycerose, diglycerol, triethylene glycol, polyethylene glycol, tris (2 -Hydroxyethyl) isocyanurate, cyclobutanediol, cyclopen Diol, cyclohexanediol, cycloheptanediol, cyclooctanediol, cyclohexanedimethanol, hydroxypropylcyclohexanol, tricyclo [5,2,02.6] decane-dimethanol, bicyclo [4,3,0] nonanediol, Dicyclohexanediol, tricyclo [5,3,1,1] dodecanediol, bicyclo [4,3,0] nonanedimethanol, tricyclo [5,3,1,1] dodecane-diethanol, hydroxypropyltricyclo [5, 3,1,1] dodecanol, spiro [3,4] octanediol, butylcyclohexanediol, 1,1-bicyclohexylidenediol, cyclohexanetriol, maltitol, lactitol, dihydroxynaphthalene, trihydroxynaphth Len, tetrahydroxynaphthalene, dihydroxybenzene, benzenetriol, biphenyltetraol, pyrogallol, (hydroxynaphthyl) pyrogallol, trihydroxyphenanthrene, bisphenol A, bisphenol F, xylylene glycol, di (2-hydroxyethoxy) benzene, bisphenol A- In addition to polyols such as bis (2-hydroxyethyl ether), tetrabromobisphenol A, tetrabromobisphenol A-bis (2-hydroxyethyl ether), dibromonepentyl glycol, epoxy resin, oxalic acid, glutamic acid, adipic acid, acetic acid , Propionic acid, cyclohexanecarboxylic acid, β-oxocyclohexanepropionic acid, dimer acid, phthalic acid, isophthalic acid, salicylic acid, 3- Condensation reaction products of organic polybasic acids such as lomopropionic acid, 2-bromoglycolic acid, dicarboxycyclohexane, pyromellitic acid, butanetracarboxylic acid, bromophthalic acid and the like with the polyol, the polyol with ethylene oxide, propylene oxide, etc. Examples include addition reaction products with alkylene oxides, addition reaction products between alkylene polyamines and alkylene oxides such as ethylene oxide and propylene oxide, but are not particularly limited thereto. These may be used alone or in combination of two or more.

  Examples of the bifunctional or higher polyol containing a sulfur atom include bis [4- (hydroxyethoxy) phenyl] sulfide, bis [4- (2-hydroxypropoxy) phenyl] sulfide, and bis [4- (2, 3-dihydroxypropoxy) phenyl] sulfide, bis [4- (4-hydroxycyclohexyloxy) sulfide, bis [2-methyl-4 (hydroxyethoxy) -6-butylphenyl] sulfide and these compounds on average 3 molecules per hydroxyl group Compounds to which ethylene oxide and / or propylene oxide are added, di (2-hydroxyethyl) sulfide, 1,2-bis (2-hydroxyethylmercapto) ethane, bis (2-hydroxyethyl) disulfide, 1,4- Dithian-2,5-diol, bi (2,3-dihydroxypropyl) sulfide, tetrakis (4-hydroxy-2-thiabutyl) methane, bis (4-hydroxyphenyl) sulfone (trade name bisphenol S), tetrabromobisphenol S, tetramethylbisphenol S, 4,4 '-Thiobis (6-tert-butyl-3-methylphenol), 1,3-bis (2-hydroxyethylthioethyl) -cyclohexane and the like can be mentioned, but are not particularly limited thereto. These may be used alone or in combination of two or more.

  The thiol compound having a hydroxy group includes those containing at least one sulfur atom in addition to the mercapto group. Specifically, 2-mercaptoethanol, 3-mercapto-1,2-propanediol, glycerin di (mercaptoacetate), 1-hydroxy-4-mercaptocyclohexane, 2,7-dimercaptophenol, 2-mercaptohydroquinone, 4-mercaptophenol, 3,4-dimercapto-2-propanol, 1,3-dimercapto-2-propanol, 2,3-dimercapto-1-propanol, 1,2-dimercapto-1,3-butanediol, pentaerythritol Tris (3-mercaptopropionate), pentaerythritol mono (3-mercaptopropionate), pentaerythritol bis (3-mercaptopropionate), pentaerythritol tris (thioglycolate), pentaerythritol pen Kiss (3-mercaptopropionate), hydroxymethyl-tris (mercaptoethylthiomethyl) methane, 1-hydroxyethylthio-3-mercaptoethylthiobenzene, 4-hydroxy-4'-mercaptodiphenylsulfone, 2- (2 -Mercaptoethylthio) ethanol, dihydroxyethyl sulfide mono (3-mercaptopropionate), dimercaptoethane mono (sulcylate), hydroxyethylthiomethyltris) mercaptoethylthiomethyl) methane, and the like. It is not limited. These may be used alone or in combination of two or more.

  When a urethane monomer is used, a polymerization catalyst such as dimethyltin dichloride, dibutyltin dichloride, dibutyltin dilaurate, azobisdimethylvaleronitrile is generally added.

  The allylic monomer corresponds to diethylene glycol bisallyl carbonate alone or a mixed monomer of a monomer copolymerizable with diethylene glycol bisallyl carbonate. Specific examples of the copolymerizable monomer include aromatic vinyl compounds such as styrene, α-methylstyrene, vinyltoluene, chlorostyrene, chloromethylstyrene, and divinylbenzene; methyl (meth) acrylate, n-butyl (meta ) Acrylate, n-hexyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, methoxydiethylene glycol (meth) acrylate, methoxypolyethylene glycol (meth) acrylate, 3-chloro-2-hydroxypropyl (meth) ) Acrylates, stearyl (meth) acrylates, lauryl (meth) acrylates, phenyl (meth) acrylates, glycidyl (meth) acrylates, mono (meth) acrylates such as benzyl methacrylate 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 3-phenoxy-2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) Mono (meth) acrylates having a hydroxy group such as acrylate; ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, 1,3- Butylene glycol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, 2-hydride Roxy-1,3-di (meth) acryloxypropane, 2,2-bis [4-((meth) acryloxyethoxy) phenyl] propane, 2,2-bis [4-((meth) acryloxydiethoxy) Di (meth) acrylates such as phenyl] propane and 2,2-bis [4-((meth) acryloxy polyethoxy) phenyl] propane; tri (meth) acrylates such as trimethylolpropane trimethacrylate and tetramethylolmethane trimethacrylate Tetra (meth) acrylates such as tetramethylolmethane tetra (meth) acrylate [wherein (meth) acrylate means methacrylate or acrylate]; diallyl phthalate, diallyl isophthalate, diallyl terephthalate, etc. Is mentioned. Needless to say, the mixture of diethylene glycol bisallyl carbonate and a copolymerizable monomer corresponds to the diethylene glycol bisallyl carbonate monomer in the present invention.

  Various known additions such as ultraviolet absorbers, infrared absorbers, light stabilizers, internal mold release agents, antioxidants, dyes, photochromic dyes, pigments, antistatic agents, etc., to the urethane or allyl monomers in the present invention An agent may be added to provide specific effects by mixing and / or polymerizing.

  According to the present invention, since an optical plastic article for infrared communication that exhibits white color visually can be provided, the degree of freedom in designing the design of a device having an infrared port is expanded. In addition, since the article is formed by forming fine particles having a microphase separation structure in the monomer as a coloring method, the article has good dispersibility and can exhibit a stable white color.

Explanatory drawing which illustrates typically the structure of microparticles | fine-particles of the micro phase-separation structure of this invention.

Hereinafter, the present invention will be described in detail by way of examples.
First, a method for producing a vinyl copolymer dispersed in a urethane-based or allyl-based monomer will be described.
100 parts by weight of methyl ethyl ketone was introduced into the reactor, nitrogen was blown into the reactor, and the temperature was raised to 80 ° C. while stirring, and this temperature was maintained.
Next, 100 parts by weight of vinyl monomer mixture (prescription of A-1 to A-11 and B-1 to B-10) is measured for each of Examples 1 to 11 and Comparative Examples 1 to 10 shown in Table 1 and Table 2. Then, 3 parts by weight of t-butylperoxy 2-ethylhexaate as a polymerization catalyst was added dropwise over 3 hours with stirring, followed by cooling with stirring at 80 ° C. for 3 hours. And the vinyl copolymer resin solution of 50% of solid content corresponding to every Comparative Examples 1-10 was obtained.

Example 1
90 parts by weight of m-xylylene diisocyanate, 130 parts by weight of pentaerythritol tetrakis (3-mercaptopropionate), 0.115 parts by weight of Seesorb 709 manufactured by Cypro Kasei Co., Ltd. as an ultraviolet absorber, and dibutyltin dichloride 0 as a polymerization catalyst After mixing .018 parts by weight and stirring, 2.2 parts by weight of the vinyl copolymer resin solution prepared with the above A-1 was added and further stirred. When almost uniform, the mixture was degassed and stirred for 30 minutes, and then poured into a molding mold comprising a glass mold and a gasket, and the temperature was raised from 40 ° C. to 130 ° C. over 6 hours to obtain a molded product.

Examples 2-6
For Examples 2 to 6, all operations were performed in the same manner as in Example 1 except that the corresponding vinyl copolymer resin solutions (A-2 to A-6) were prepared, and molded bodies were obtained. .

Example 7
To 100 parts by weight of diethylene glycol bisallyl carbonate, 0.1 part by weight of 2- (2-hydroxy-4-octylphenyl) -benzotriazole as an ultraviolet absorber and 3 parts by weight of diisopropyl peroxycarbonate as a polymerization catalyst were mixed. After stirring, 2.2 parts by weight of the vinyl copolymer resin solution prepared with B-1 was added and stirred. When it became almost uniform, it was deaerated for 10 minutes, and then poured into a molding mold consisting of a glass mold and a gasket, and the temperature was raised from 30 ° C. to 80 ° C. over 15 hours to obtain a molded product.

Examples 8-11
For Examples 8 to 11, all operations were performed in the same manner as in Example 7 except that the corresponding vinyl copolymer resin solutions (B-2 to B-5) that were prepared respectively were used, and molded bodies were obtained. .

Comparative Examples 1-5
About Comparative Examples 1-5, except having used the said adjusted vinyl copolymer resin solution (A-7-A-11) respectively corresponding, it operated similarly to Example 1 and obtained the molded object. .

Comparative Examples 6-10
Comparative Examples 6 to 10 were all operated in the same manner as in Example 7 except that the corresponding vinyl copolymer resin solutions (B-6 to B-10) that were prepared were used to obtain molded articles.

Regarding the performance evaluation method, the evaluation standard of whiteness is as follows.
○: Molded body is uniformly cloudy ●: Molded body is colorless and transparent ×: Molded body is opaque (precipitation of fine particles)
The above was judged visually.
Infrared transmittance ◯: Transmittance at 1 mm thickness of 950 nm is 12% or more X: Transmittance at 1 mm thickness of 950 nm is less than 12% The spectrophotometer used is Hitachi spectrophotometer U-4100 Made by Hitachi Technologies).

About performance evaluation result The whiteness and infrared transmittance (950 nm) by the external appearance of the molded object obtained in the said Examples 1 and Comparative Examples 1-10 were evaluated, and it showed in Table 1 and Table 2. FIG.
As an evaluation result, in all of the examples, the molded body was uniformly clouded by visual observation, and could not be seen through the molded body. In addition, the transmittance of 12% necessary for this kind of optical plastic article for infrared communication can be secured at 950 nm which is an infrared region.
On the other hand, in Comparative Example 1 and Comparative Example 6, the molded product is already transparent at the stage where the vinyl copolymer resin has a portion corresponding to the vinyl monomer (A), which is slightly more than 45% by weight. Was confirmed. On the contrary, in Comparative Example 2 and Comparative Example 7, when the portion of the vinyl copolymer resin corresponding to the vinyl monomer (B) is less than 10% by weight, it becomes transparent even if the vinyl monomer (A) is contained in a relatively large amount. It was confirmed that. In particular, in Comparative Example 2 and Comparative Example 7, the SP value of the vinyl monomer occupying the portion other than the vinyl monomers (A) and (B) is not so low, but becomes transparent. ) Was confirmed.
In Comparative Example 4 and Comparative Example 9, the molded product is transparent because the weight average molecular weight of the vinyl copolymer resin is small. Similarly, in Comparative Example 5 and Comparative Example 10, opaque white turbidity, that is, sedimentation occurs, and a transmittance of 12% is not obtained. This is because the vinyl copolymer resin has a large weight average molecular weight.

Claims (3)

The following vinyl copolymer (C) having a weight average molecular weight larger than 1,000 and smaller than 500,000 is introduced into a urethane-based or allyl-based monomer, and the monomer is heated or photocured by stirring. A method for producing an optical plastic article for infrared communication, wherein the vinyl copolymer (C) is dispersed in a cured product to form microphase-separated fine particles.
(1) 5 to 45% by weight of a vinyl monomer (A) having a SP value of less than 3 and a molecular weight of 180 or more, compared to the SP value of the cured product of the urethane-based or allyl-based monomer,
(2) Vinyl copolymer weight obtained by copolymerizing 10 to 95% by weight of a vinyl monomer (B) having a SP value of 3 or more with respect to the SP value of the cured product of the urethane or allyl monomer. Combined (C)   2. The optical plastic for infrared communication according to claim 1, wherein the vinyl copolymer (C) contains 0 to 85% by weight of a vinyl monomer other than the vinyl monomers (A) and (B) as a copolymer component. Article manufacturing method.   3. The average particle size of the fine particles derived from the vinyl copolymer (C) dispersed in the cured product of the urethane-based or allyl-based monomer is 0.05 μm or more. A method of manufacturing an optical plastic article for infrared communication.

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