JP2012123236A - Coloring method for plastic optical member and plastic optical member colored by the method - Google Patents

Abstract

PROBLEM TO BE SOLVED: To color a plastic optical member in a desired color with high optical permeability and without causing unevenness in color and to overcome problems related to coloring processing such as wastewater disposal and energy loss.SOLUTION: In a coloring method for coloring a plastic optical member through irradiation with ionizing radiations such as gamma rays and electron beams, a dose of the radiation employed for irradiating the plastic optical member is selected from radiation doses precedently determined in accordance with colors to be obtained, and a color of the plastic optical member attained a prescribed period of time after the irradiation is employed as a color to be obtained.

Description

  The present invention relates to a coloring method of a colored plastic optical member having high light transmittance and a plastic optical member colored by this method.

  A description will be given of a vision correction eyeglass lens and a sunglasses lens, which are one of plastic optical products.

  In general, an ultraviolet absorber that absorbs ultraviolet rays in a high energy region of 430 nm wavelength or less is used for plastic lenses such as a vision correction eyeglass lens and a sunglasses lens in order to protect the eyes or give fashion. Of course, the lens is often colored.

  According to Sanseido Ojibayashi, “a lens is an optical element that refracts light to diverge or focus it. Usually, it is a transparent body with both spherical surfaces and spherical surfaces. "Aspherical lenses with one or both sides made of a spherical surface are also used", but here, those that simply transmit or reflect light, as well as lenses for correcting astigmatism used for spectacle lenses, etc. Will be described as a lens.

  As a method for coloring a lens, there is a method in which at least a part of a molded product to be a lens is immersed in a dye bath containing a dye for a predetermined time so that the molded product is infiltrated with a dye (patented). Reference 1).

  However, in this method, since the dye is dispersed in the lens, the light entering the lens is diffused by the dye to reduce the light transmittance. There was a phenomenon that felt darker than when seen with the naked eye. Further, since this coloring method uses a dye bath solution, uneven dispersion of the dye in the dye bath solution, and further uneven penetration of the dye when the molded product is immersed in the dye bath solution are generated. In some cases, quality problems occur. For this reason, it has been necessary to take a coloring treatment method using a pair of left-eye and right-eye lenses (preventing uneven coloring). At the same time, there are problems such as wastewater treatment of the liquid in which the dye used in the dyeing bath is mixed, and loss of energy used for temperature control during the dyeing process.

  As another method, the lens is quickly colored to function as sunglasses when exposed to light containing ultraviolet rays such as sunlight, and fading and transparent in an indoor environment without such light irradiation. Regarding the production of spectacles that function as ordinary spectacles, so-called photochromic plastic lenses, there are methods using a photopolymerization initiator (Patent Document 2) and (Non-Patent Document 1).

  However, since this method is a lens having photochromic properties, it is difficult to obtain a lens that is always colored, and it is difficult to perform predetermined coloring. Further, in order to place importance on photochromic properties, no consideration has been given to the transmittance of light transmitted through the lens.

  On the other hand, it is known that a synthetic resin such as a thermoplastic resin or a thermosetting resin used as a lens material is colored when irradiated with ionizing radiation in the manufacturing process or the process of using the resin (Patent Document 3). . However, this radiation irradiation is not intended to positively color the resin for use, but has been devised to treat coloring as an obstacle and prevent coloring.

  In addition, a coloring method is known in which a coating (resin composition containing a color former) formed on the surface of a substrate is colored by exposure to radiation (Patent Document 4).

  However, in this coloring method, it is necessary to coat the surface of the substrate with a resin composition to be colored, and the substrate itself cannot be colored.

JP 2005-508459 gazette JP 2004-285141 A JP 2010-059295 A Special table 2007-532707 gazette

Web literature: Color-changing molecules -chromic molecules- http://www.chem-station.com/yukitopics/photochromic.htm

  The present invention realizes a plastic optical member which is uniformly colored without unevenness and has a high light transmittance by simple processing process management in the coloring of the plastic optical member, and further, waste water related to the coloring treatment. It is to eliminate problems such as processing and energy consumption.

  The present invention irradiates a plastic optical member with ionizing radiation, and adopts the color after the lapse of a predetermined period from the irradiation as the color of the plastic optical member, thereby reforming the plastic optical member and transmitting the sight It achieves predetermined coloring with a high rate (hereinafter referred to as transmittance).

1st invention is the coloring method of the plastic optical member which colors this plastic optical member by irradiating the plastic optical member with ionizing radiation,
The plastic optical member coloring method is characterized in that the amount of radiation applied to the plastic optical member is set by selectively setting a predetermined amount of radiation according to the color to be colored.

  According to a second invention, in the first invention, the plastic optical member is at least one of a resin composition based on a raw material monomer of a (thio) urethane resin and a resin composition based on an allyl monomer. This is a method for coloring a plastic optical member.

  A third invention is the plastic optical member coloring method according to any one of the first to second inventions, wherein the ionizing radiation to be irradiated is a gamma ray or an electron beam.

  A fourth invention is a plastic optical member characterized by being colored according to any one of the first to third inventions.

  The coloring method of the plastic optical member of the present invention is a coloring process by irradiating the plastic optical member with a predetermined radiation dose and allowing a predetermined period of time after irradiation with the radiation. The uniform coloring can be realized.

  The effect will be described in detail by taking as an example a coloring method for plastic lenses for spectacles. The coloring of plastic lenses is a coloring treatment by irradiation with ionizing radiation, and the material permeability of ionizing radiation is very high, so that there is no unevenness in the radiation processing lots of the single lens and multiple lenses. Coloring can be realized.

  From this, it is possible to reduce unnecessary management work such as coloring processing for the pair of left-eye and right-eye lenses as in the prior art coloring, and to achieve uniform coloring of a large number of lenses simultaneously. it can.

  In addition, since the substance permeability of ionizing radiation is very high, ultraviolet absorbers, infrared absorbers, light stabilizers, internal mold release agents, antioxidants, dyes, photochromic dyes, pigments, antistatic agents, Even a lens to which various known additives such as a polarizing agent (polarizing film) are added can be uniformly colored in a predetermined color although it is slightly different from the color when the additives are not added.

  Furthermore, since the material permeability of ionizing radiation is very high, the time required for the coloring treatment work is several hours compared to the conventional coloring treatment, which takes several hours. By this, the coloring process work can be completed.

  In addition, regarding the selection of the color to be colored, it is possible to realize coloring of a predetermined color by selecting a radiation dose corresponding to a preset color as the radiation dose to be irradiated.

  Moreover, since it is a coloring treatment by irradiation with ionizing radiation, it is not necessary to penetrate the lens with a foreign substance such as a dye for coloring the lens, and a bright colored lens having a transmittance equal to or higher than that of coloring with a dye or the like. Can be obtained.

  In addition, since it is ionizing radiation irradiation and is a coloring process that does not require a dye, the wastewater treatment of the liquid mixed with the dye used in the dyeing bath liquid, which has been performed in the prior art, and further, during the dyeing process Loss of energy used for temperature control or the like can be reduced.

  In addition, since the present invention is not a method of dyeing a molded member by infiltrating a dye, it can realize a coloring process by irradiation with ionizing radiation. The coloring treatment can be performed by performing ionizing radiation irradiation as it is. Thus, even in the case of glasses in use, it is possible to easily perform a coloring process to a predetermined color, and the glasses can be used instead of fashionable glasses.

  Furthermore, the lens irradiated with the ionizing radiation of the present invention absorbs light having a short wavelength (light having a wavelength of about 480 nm or less) having a large amount of energy without performing special light shielding treatment, and light having other wavelengths. Therefore, it can function as a light-shielding lens that absorbs light in the ultraviolet region. This effect becomes more prominent as the radiation dose to be irradiated increases. In addition, since short-wavelength light that causes glare is absorbed, it is easy to determine the intensity of light of other wavelengths, and a high-contrast lens can be obtained.

It is a coloring state figure which shows one Example of coloring of the thermosetting resin by ionizing radiation irradiation of this invention. It is the characteristic view which analyzed the spectrum of the transmitted light of the lens colored with the coloring method of this invention. It is process drawing which shows the manufacturing process of a plastic optical member.

  The present invention relates to a plastic optical member that irradiates a plastic optical member with ionizing radiation and colors the plastic optical member by adopting a color after a predetermined period of time has passed as the color of the plastic optical member. A coloring method and a plastic optical member produced thereby. The radiation dose applied to the plastic optical member is selected by selecting a radiation dose that is predetermined according to the color of the plastic optical member.

  The plastic optical member is composed of at least one of a resin composition based on a raw material monomer of a (thio) urethane resin and a resin composition based on an allyl monomer. The following are mentioned as a monomer used for the lens material based on the raw material monomer of (thio) urethane type resin.

  Examples thereof include a combination of a polyisocyanate compound and a polyol compound, a combination of a polyisocyanate compound and a polythiol compound, a combination of a polyisocyanate compound and a thiol compound having a hydroxy group, and the like.

  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, Examples thereof include polyiso (thio) cyanate compounds having two or more iso (thio) cyanate groups in the molecule, 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 ether) E) 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 Natomethyl-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-isocyanate) Anatopropyl) -5- (2-isocyanatoethyl) -bicyclo- [2,2,1] -heptane, 2-isocyanatomethyl-2- (3-isocyanatopropyl) -6- (2-isocyanate) Alicyclic polyisocyanates such as ethyl) -bicyclo- [2,2,1] -heptane; phenylene diisocyanate, tolylene diisocyanate, ethylphenylene diisocyanate, isopropylphenylene diisocyanate, dimethylphenylene diisocyanate , Diethylphenylene diisocyanate, diisopropylphenylene diisocyanate, trimethylbenzene triisocyanate, benzene triisocyanate, naphthalene diisocyanate, methyl naphthalene diisocyanate, biphenyl diisocyanate, toluidine diisocyanate Narate, 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 , F Sahydrobenzene 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 Aromatic polyisocyanates such as diisocyanate, dibenzofurandiocyanate, carbazole diisocyanate, ethylcarbazole diisocyanate, dichlorocarbazole diisocyanate; thiodiethyl diisocyanate, thiodipropyl diisocyanate, thiodihexyl di Isocyanate, dimethylsulfone diisocyanate, dithiodimethyl diisocyanate, dithi Sulfur-containing aliphatic polyisocyanates such as odiethyl diisocyanate and dithiodipropyl diisocyanate, diphenyl sulfide-2,4′-diisocyanate, diphenyl sulfide-4,4′-diisocyanate, 3,3 ′ -Aromatic sulfides such as dimethoxy-4,4'-diisocyanate dibenzylthioether, bis (4-isocyanatomethylbenzene) sulfide, 4,4'-methoxybenzenethioethylene glycol-3,3'-diisocyanate Diisocyanate; diphenyl disulfide-4,4′-diisocyanate, 2,2′-dimethyldiphenyl disulfide-5,5′-diisocyanate, 3,3′-dimethyldiphenyl disulfide-5,5′-diisocyanate Nate, 3,3'-dimethyldiphenyl disulfide- , 6′-diisocyanate, 4,4′-dimethyldiphenyl disulfide-5,5′-diisocyanate, 3,3′-dimethoxydiphenyl disulfide-4,4′-diisocyanate, 4,4′-dimethoxy Aromatic disulfide polyisocyanates such as diphenyl disulfide-3,3′-diisocyanate; 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 Narate, 3,3′-dimethoxy-4,4′-diisocyanate dibenzyl Ruhon, 4,4′-dimethyldiphenylsulfone-3,3′-diisocyanate, 4,4′-di-tert-butyldiphenylsulfone-3,3′-diisocyanate, 4,4′-methoxybenzeneethylene Aromatic sulfone polyisocyanates such as disulfone-3,3′-diisocyanate and 4,4′-dichlorodiphenylsulfone-3,3′-diisocyanate; 4-methyl-3-isocyanatobenzenesulfonyl-4 '-Isocyanate phenol ester, 4-methoxy-3-isocyanatobenzenesulfonyl-4'-isocyanate phenol ester and other sulfonate ester type polyisocyanates; 4-methyl-3-isocyanatobenzenesulfonylanilide-3'- Methyl-4'-isocyanate, dibenzenesulfonyl -Ethylenediamine-4,4'-diisocyanate, 4,4'-methoxybenzenesulfonyl-ethylenediamine-3,3'-diisocyanate, 4-methyl-3-isocyanatobenzenesulfonylanilide-4-methyl-3 ' -Aromatic sulfonic acid amides such as isocyanate; sulfur-containing heterocyclic compounds such as thiophene-2,5-diisocyanate, and other 1,4-dithiane-2,5-diisocyanate, etc. It is not limited to. In addition, they 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 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, dolitol, idiitol, glycol, inositol, hexanetriol, triglycerose, diglycerol, triethylene glycol, polyethylene glycol, tris (2 -Hydroxyethyl) isocyanurate, cyclobutanediol, cyclopen Diol, cyclohexanediol, cycloheptanediol, cyclooctanediol, cyclohexanedimethanol, hydroxypropylcyclohexanol, tricyclo [5,2,1,02.6] 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, trihydroxynaphthal Talen, 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, 6-oxocyclohexanepropionic acid, dimer acid, phthalic acid, isophthalic acid, salicylic acid, -Condensation reaction product of organic polybasic acid such as bromopropionic acid, 2-bromoglycolic acid, dicarboxycyclohexane, pyromellitic acid, butanetracarboxylic acid, bromophthalic acid and the like with the polyol, the polyol with ethylene oxide or propylene oxide Examples include addition reaction products with alkylene oxides, and 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, (2,3-dihydroxypropyl) sulfide, tetrakis (4-hydroxy-2-thiabutyl) methane, bis (4-hydroxyphenyl) sulfone (trade name bisphenol S), tetrabromobisphenol S, tetramethylbisphenol S, 4, Examples thereof include 4′-thiobis (6-tert-butyl-3-methylphenol) and 1,3-bis (2-hydroxyethylthioethyl) -cyclohexane, but are not particularly limited thereto. These 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] pepta-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-mercapto-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), pentaerythritol Aliphatic tetrathiols such as 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 (mercaptomethylene) Oxy) benzene, 1,4-bis (mercaptomethyleneoxy) ) 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, 1,3,5 -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) benzene 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 (mercaptoethyl) ) Benzene, 1,2,3,5-tetrakis (mercaptoethyl) benzene, 1,2,4,5-tetrakis (mer) Ptoethyl) 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-naphthalene Dithiol, 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,
2,5-dichlorobenzene-1,3-dithiol, 1,3-di (p-chlorophenyl) propane-2,2-dithiol, 3,4,5-tribromo-1,2-dimercaptobenzene, 2, Halogen-substituted aromatic polythiols such as chlorine-substituted products such as 3,4,6-tetrachloro-1,5-bis (mercaptomethyl) benzene and bromine-converted products;
Further, 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 -Polythiols containing heterocycles such as triazine, 2-thiobenzeneoxy-4,6-dithiol-sym-triazine, 2-thiobutyloxy-4,6-dithiol-sym-triazine, and their chlorine-substituted products, bromine Examples include halogen-substituted compounds such as substituted compounds, but are not limited thereto. 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.

  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), hydroxyethylthiomethyl-tris) mercaptoethylthiomethyl) methane, etc. It is not limited. These may be used alone or in combination of two or more.

  When a (thio) urethane-based monomer is used, a polymerization catalyst such as dimethyltin dichloride, dibutyltin dichloride, dibutyltin dilaurate, or 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 ( (Meth) attalylate, n-hexyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, methoxydiethylene glycol (meth) acrylate, methoxy polyethylene glycol (meth) acrylate, 3-chloro 2- (Hydroxypropyl) (meth) acrylate, stearyl (meth) acrylate, lauryl (meth) acrylate, phenyl (meth) acrylate, glycidyl (meth) acrylate, benzyl methacrylate, etc. Kind;
2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 3-phenoxy-2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meta ) Mono (meth) acrylates having hydroxy groups 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 , 6-hexanediol di (meth) acrylate, neopentylglycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, 2-hydroxy-1,3-di (meth) acryloxypropane, 2,2 -Bis [4-((meth) acryloxyethoxy) phenyl] propane, 2,2-bis [4-((meth) acryloxy-diethoxy) phenyl] propane, 2,2-bis [4-((meth) acryloxy)・ Di (meth) atarire such as polyethoxy) phenyl] propane Door like;
Tri (meth) acrylates such as trimethylolpropane trimethacrylate and tetramethylolmethanetrimethacrylate; tetra (meth) acrylates such as tetramethylolmethanetetra (meth) acrylate [provided that (meth) acrylate in this specification Means methacrylate or acrylate]; diallyl phthalate, diallyl isophthalate, diallyl terephthalate and the like. 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.

  In addition, various known additives such as ultraviolet absorbers, infrared absorbers, light stabilizers, internal mold release agents, antioxidants, dyes, photochromic dyes, pigments, antistatic agents, and polarizing agents (polarizing films) are added. Thus, specific effects may be given by mixing and / or polymerizing. In the present invention, this specific effect is expressed and described as an additional process of function enhancement.

  The radiation to be irradiated may be either a gamma ray or an electron beam, but an electron beam is preferable in consideration of convenience such that the coloring treatment work can be performed in a short time.

  Further, as one of the plastic optical members, even in the state of spectacles in which the lens and the frame are integrated, the lens can be colored by performing the radiation treatment on the spectacles.

  As Example 1, a spectacle lens of a plastic optical member colored by ionizing radiation irradiation (hereinafter referred to as a lens) will be described with reference to the drawings.

  As shown in FIG. 3, the production of a lens using plastic (thermosetting resin composition) is generally performed by a generally performed method: [casting process] → [cutting / polishing] [Process] → [Optical inspection process] → [Dyeing process] → [Coating process] → [Ball shape processing process] → [Final inspection process]

  However, in the practice of the present invention, the ionizing radiation irradiation process is performed as the dyeing process, and the process sequence at that time is [coating process] → [radiation irradiation process] → [lens processing process]. → [Final inspection process] will be performed. However, after the [radiation irradiation step], a [predetermined period elapsed step] is preferably interposed between the [radiation irradiation step] and the [lens processing step].

  In addition, the manufacturing process of this lens shows a general procedure, and the order of the processes can be changed as appropriate depending on the type of additional processing for function enhancement.

  The outline of each process is as follows.

[Casting process]
In the casting process, a monomer (liquid plastic material) containing a resin that is the raw material for the lens base material is prepared, poured into a mold called a mold, and then heated in an electric furnace to homogenize the molecular structure. It is a process of hardening and manufacturing a prototype of the lens.

[Cutting and polishing process]
The cutting / polishing process consists of four stages: rough cutting, precision grinding, polishing and cleaning. Rough cutting is a stage in which the lens base is blocked by the shaft and center marking, and a machine called a generator is used to cut the back surface in accordance with a specified frequency. At this stage, the cutting surface is rough, and the fine adjustment of the curve is performed by the next precision grinding. Precision grinding is a stage where the surface machined by the generator is further finely cut by a machine using a diamond blade to form an error curve of 0.1 mm or less. Polishing is a stage in which the curved surface of a precision-ground lens substrate is polished with an abrasive mixed with polishing powder to polish the surface. Cleaning is a process of removing dirt and foreign matter after polishing.

[Optical inspection process]
The optical inspection step is a step of inspecting the surface accuracy, optical accuracy, and appearance accuracy of the lens substrate by comparison with design values.

[Coating process]
The coating process consists of three stages: hard coat treatment, cleaning and multi-coat treatment. In the hard coat treatment, after removing dirt and dust from the lens substrate by ultrasonic cleaning or the like, a silicon resin hard coat solution is applied to the surface of the lens substrate and cured by heat treatment. In the cleaning process, dirt and dust on the surface of the lens substrate are removed by ultrasonic cleaning or the like. In multi-coat treatment, an anti-reflection film is deposited on the back surface of the lens substrate by vacuum deposition to suppress reflection on the surface of the lens substrate, as well as a film that increases reflection as needed, and dirt and water. A film for preventing burn is formed as necessary.
In addition, although the dyeing process before the coating process is not usually performed, an ultraviolet absorber, an infrared absorber, a light stabilizer, an internal mold release agent, an antioxidant, a dye, a photochromic dye, a pigment, an antistatic agent, This is appropriately performed when an addition treatment is required by adding known various additives such as a polarizing agent (polarizing film).

[Radiation irradiation process]
The radiation irradiation step is to irradiate the lens substrate with radiation by selecting the radiation irradiation intensity and time from a predetermined reference for the radiation dose, time, etc. corresponding to the color to be colored on the lens substrate, Irradiation is performed in the atmosphere at room temperature, and the irradiation dose is appropriately selected from 10 to 300 kGy (kilo gray) according to the color to be colored. The radiation to be irradiated is a gamma ray or an electron beam, and an electron beam is preferable in consideration of convenience such as being able to perform a color treatment for a short time.

[Ball processing process]
In the target lens processing step, target lens processing is performed to cut the outer peripheral surface of the lens base material in accordance with the shape of the frame in response to a request from an eyeglass store. A jig is attached to the outer peripheral surface of the lens base material without changing the size.

[Final inspection process]
In the final inspection process, the final inspection of the optics, appearance, and color tone of the lens finished through each process and inspection is performed.

  The coloring of the lens is completed when the color development is stabilized by allowing a predetermined period (about 100 days) to elapse in a natural environment after irradiation.

  However, as will be described later, since the lens color can clearly correspond to the lens color immediately after radiation irradiation and after a predetermined period of time for each radiation irradiation dose, the lens immediately after radiation irradiation can be used as it is. it can. In this case, the lens color changes with time in the course of the predetermined period.

  The lens shown in FIG. 1 is a resin composition in which a small amount of an ultraviolet absorber that absorbs ultraviolet rays having a wavelength of 430 nm or less is mixed with isocyanate-based and polythiol-based monomers in a ratio of 50%: 50% (equal amount). The thickness is 2.0 mm and there is no degree. In addition, as a representative example of the functional enhancement addition process, the coloring state of the same lens subjected to the hard coat process is also displayed.

  The ionizing radiation to be irradiated uses gamma rays from cobalt 60, and the irradiated radiation dose has seven levels of 10, 50, 100, 150, 200, 250, and 300 kGy. And the environment of ionizing radiation irradiation is in air | atmosphere and room temperature.

  In accordance with the sample number in FIG. 1, the radiation dose of gamma rays irradiated by cobalt 60 is increased, and the coloration status of the lens displays changes in the coloration status immediately after the ionizing radiation irradiation and after 100 days from the ionizing radiation irradiation. did. In addition, the photograph for each sample number: The left side is a normal lens that has not been subjected to additional processing (indicated as a normal product), and the right side is a lens that has been subjected to a hard coat treatment as a representative of additional processing for functional enhancement (hardware) This shows a photo of “With coat”. The color display under the photograph for each sample number in FIG. 1 is described in comparison with JIS Z 8102: 2001 “Color Name of Object”.

  The term “immediately after radiation irradiation” refers to the time when the lens is obtained after the radiation irradiation is performed by the radiation irradiation engine, and is about one week after the radiation irradiation date.

  As a result, the coloration of the lens by ionizing radiation irradiation develops a reddish color as a whole immediately after the ionizing radiation irradiation, but changes to a greenish color when viewed 100 days after the ionizing radiation irradiation. I understood it. Although not shown here, this color change becomes the same color as that of about 100 days after 10 to 20 days have passed since the ionizing radiation irradiation, and the color change is small thereafter. In the course of 100 days, it was found that the change in the developed color is almost stable to the desired color.

  Therefore, according to the coloring method of the present invention, the color of the lens is selected based on the color sample at the final completion stage (100 days after irradiation with ionizing radiation) in response to the customer's request for coloring. By selecting the radiation dose, coloring to a predetermined color is possible.

  However, as described above, the coloring of the lens can clearly correspond to the lens color immediately after radiation irradiation and after the lapse of a predetermined period for each radiation irradiation dose, so the lens immediately after radiation irradiation can be used as it is. it can. In this case, the lens color changes with time in the course of the predetermined period.

  About this color change over time, the plastic resin mixed as the lens material is cross-linked by irradiation with ionizing radiation, and further, the cross-linking is promoted over time and stabilized over time. I guess that.

  Thus, it is possible to select a color to be colored by selecting and irradiating the radiation dose of ionizing radiation, and although not shown here, an ultraviolet absorber, an infrared absorber, a light stabilizer, The same ionizing radiation is applied to lenses subjected to addition treatment by adding various known additives such as internal mold release agents, antioxidants, dyes, photochromic dyes, pigments, antistatic agents, and polarizing agents (polarizing films). Although coloring by irradiation was performed, it was confirmed that the color to be colored can be selected by selecting and irradiating the radiation dose of the ionizing radiation as in the case of the normal product. In this case, although it became a slightly dull color compared with coloring of a normal product, the almost same coloring tendency was able to be obtained.

  As Example 2, the transmittance most relevant to the brightness of a lens colored by ionizing radiation irradiation will be described with reference to Table 1.

  The lens used was subjected to a test for confirming the transmittance of the lens using the same plastic resin as in Example 1 under the following test conditions.

〔lens〕
The lens functions as a plastic resin in which isocyanate and polythiol monomers are mixed in a ratio of 50%: 50% (equal amount) and a trace amount of UV absorber that absorbs UV rays of about 430 nm wavelength or less. Two types of lenses (HMC) that have been subjected to both hard coating and multi-coating treatments (non-up-added lens (normal product)) and those that have been irradiated with an electron beam (electron) Line irradiation) and those not irradiated with an electron beam (for comparison).

[Ionizing radiation irradiation]
The ionizing radiation to be irradiated is an electron beam, and the radiation dose is selected stepwise between 10 kGy and 300 kGy. Test 1 is 10 kGy, Test 2 is 50 kGy, Test 3 is 100 kGy, Test 4 is 200 kGy, Test 5 Was 300 kGy.

[Permeability measurement period]
The transmittance was measured by tracking and checking for about 4 months based on the fact that the above-mentioned change in coloring changes with time.

[Confirmation test results]
Although the lens of the present invention was also described in the coloring of Example 1 above, there is a change with time, and it takes about 100 days for the effect of ionizing radiation irradiation to be stabilized. The rightmost numerical value (transmittance when 110 to 120 days passed) was evaluated.

As a result, the following could be confirmed.
1) When the radiation dose is as low as about 10 to 100 kGy, the transmittance can be maintained higher than that for comparison in both the normal electron beam irradiation product and the HMC.
2) When the radiation dose is 200 to 300 kGy, the comparative transmittance tends to be high, but the difference is about 7% (relative).
3) Comparing the HMC with the normal product irradiated with the electron beam, the transmittance of the product irradiated with the HMC as compared with the normal product is small but high.

  In this confirmation test, when the radiation dose of the electron beam is 200 to 300 kGy, the fact that the transmittance of the electron beam irradiation tends to be lower than the transmittance for comparison will be described as “Ionizing radiation irradiation”. The lens colored by absorbing the light of the short wavelength that causes glare makes it easy to distinguish the intensity of the light of other wavelengths and can make the lens with a high contrast. A decrease of about 7% (relative) is sufficiently absorbed, and a bright field lens can be achieved.

  The property of light transmitted through a lens colored by irradiation with ionizing radiation will be described with reference to FIG.

  The lens is a normal product of Example 1, and is irradiated with gamma rays of cobalt 60 as ionizing radiation in 10, 50, 100, 150, 200, 250, and 300 kGy radiation doses, and 100 days have passed after irradiation. Spectral spectra were measured using a sample and a normal product that was not irradiated with gamma rays. A tungsten lamp / D2 lamp was used as a light source for spectral spectrum measurement, and U3500 (manufactured by Hitachi, Ltd.) was used as a spectral spectrum measuring instrument.

  As a result, ordinary products generally absorb light with a wavelength of about 430 nm or less due to the action of an ultraviolet absorber generally added and used as a plastic lens, but light with a wavelength longer than that is about 90%. In contrast to the transmittance, the one irradiated with gamma rays from cobalt 60 has an expanded light absorption range, almost absorbs light in the wavelength range of 480 nm or less, and the transmittance at wavelengths longer than that is cobalt. It was found that the radiation dose of gamma rays due to 60 decreased as the radiation dose increased, and the total transmission amount decreased.

  Here, the gamma ray irradiated with cobalt 60 decreases the transmission amount of light having a wavelength of 480 nm or more, reduces the total transmission amount of light, and darkens the field of view. On the other hand, since light in a wavelength region of 480 nm or less is hardly absorbed and transmitted, light having a high energy wavelength that causes a glare phenomenon is eliminated, and the lens as a whole can have a high contrast.

  The coloring of glasses by ionizing radiation irradiation will be described.

  The spectacles were irradiated with ionizing radiation in the state of spectacles with the lens attached to the frame, and the thermosetting resin lens attached to the spectacles was colored in a predetermined manner.

  About the coloring condition of a lens, predetermined | prescribed coloring can be obtained by implementing according to the conditions of the said Examples 1-3.

  In addition, since the lens and the frame are irradiated together with ionizing radiation, the frame needs to be made of a radiation resistant material.

  Although the embodiments of the present invention have been described with reference to the first to fourth embodiments, the use of eyeglass lenses for coloring will be described.

  Since the coloration of lenses is expected to be particularly fashionable, customer demands for lens colors vary greatly.

  In order to meet this customer's request, the first step is “selection by color sample of the lens as the final product”. The color sample as the final product needs to be stored in a database in correspondence with the ionizing radiation irradiation conditions for coloring the color of the lens. Of course, when the lens materials are different, it is necessary to verify the coloring condition data based on the relationship between the lens material and the radiation dose to be irradiated in advance and create a database.

  In accordance with the color sample of the lens as the final product, the lens color to be colored is selected according to the customer's request.

  And based on the database of the said ionizing radiation irradiation conditions, the radiation dose required for irradiation is selected from the color selected by the customer. The lens is irradiated with ionizing radiation in accordance with this radiation dose, and is a finished product after being left for a predetermined period of stabilization (about 100 days in Examples 1 and 2 above). By taking such a form, the lens of the thermosetting resin of the present invention can be colored.

  On the other hand, the coloration of the lens can clearly correspond to the lens color immediately after the irradiation with radiation and after the elapse of a predetermined period for each irradiation dose, so that the lens immediately after the irradiation can be used as it is. In this case, the lens color changes with time in the course of the predetermined period.

  The coloring method of the present invention can be applied to coloring of various forms of plastic optical members other than lenses.

Claims (4)

In the plastic optical member coloring method of coloring the plastic optical member by irradiating the plastic optical member with ionizing radiation,
A method for coloring a plastic optical member, wherein the radiation dose of the ionizing radiation applied to the plastic optical member is selected and irradiated according to a color to be colored on the plastic optical member.   2. The plastic optical member according to claim 1, wherein the plastic optical member is composed of at least one of a resin composition based on a raw material monomer of a (thio) urethane resin and a resin composition based on an allyl monomer. A method for coloring a plastic optical member according to the description.   3. The method for coloring a plastic optical member according to claim 1, wherein the ionizing radiation to be irradiated is a gamma ray or an electron beam.   A plastic optical member colored by any one of the inventions according to claims 1 to 3.

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