Composition for dyeing optical lenses and method for manufacturing ultraviolet-absorbing optical lenses

Abstract

The present invention aims to provide an optical lens dyeing composition that exhibits good temporal stability and can dye optical lenses with an ultraviolet absorber. [Solution] An optical lens staining composition comprising a UV absorber (A) having a triazine moiety, a dispersant (B), and water (C), wherein the dispersant (B) is a polymer comprising styrene monomer units and maleic acid ester monomer units, and the maleic acid ester monomer units are units having a carboxyl group and one or more esters selected from the group consisting of alkoxy(poly)ethylene oxyesters and alkoxy(poly)propylene oxyesters.

Description

[Technical Field]

[0001] The present invention relates to a composition containing an ultraviolet absorber used for dyeing optical lenses. [Background technology]

[0002] A method has been disclosed in which an optical lens is formed by melt-kneading a resin and an ultraviolet absorber to impart ultraviolet absorption properties to the optical lens (Patent Document 1). In recent years, a composition has been disclosed in which an ultraviolet absorber having a triazine moiety capable of blocking blue light has been applied to an optical lens in order to block blue light originating from liquid crystal displays (Patent Document 2). [Prior art documents] [Patent Documents]

[0003] [Patent Document 1] Japanese Patent Publication No. 2010-168462 [Patent Document 2] International Publication No. 2018 / 123267 [Overview of the Initiative] [Problems that the invention aims to solve]

[0004] However, among UV absorbers, those containing a triazine moiety are poorly water-soluble, making it impossible to dye optical lenses with UV absorbers by methods other than melt kneading.

[0005] The present invention aims to provide an optical lens dyeing composition that exhibits good temporal stability and allows for the dyeing of optical lenses with an ultraviolet absorber. [Means for solving the problem]

[0006] The optical lens dyeing composition of the present invention comprises a UV absorber (A) having a triazine moiety, a dispersant (B), and water (C). The dispersant (B) is a polymer containing styrene monomer units and maleic acid ester monomer units. The maleic acid ester monomer unit is a unit having a carboxyl group and one or more esters selected from the group consisting of alkoxy(poly)ethylene oxyesters and alkoxy(poly)propylene oxyesters. [Effects of the Invention]

[0007] According to the present invention described above, it is possible to provide an optical lens dyeing composition that has good temporal stability and can dye optical lenses with an ultraviolet absorber. Furthermore, the present invention can provide a method for manufacturing ultraviolet absorbing optical lenses. [Modes for carrying out the invention]

[0008] This specification defines the following terms. A monomer is the state before polymerization, and a monomer unit is the state in which it constitutes part of a polymer after polymerization. Dyeing means that an optical lens can be impregnated into the composition so that an ultraviolet absorber can be contained inside the optical lens. Dyeing also includes the embodiment in which the composition is coated onto the optical lens to form an ultraviolet absorbing layer for use. (Poly)ethylene oxy means an embodiment containing one or more ethylene oxy moieties. The same applies to (poly)propylene oxy.

[0009] The optical lens staining compositions of this specification (hereinafter referred to as "compositions") comprise a triazine moiety-containing ultraviolet absorber (A) (hereinafter referred to as "ultraviolet absorber (A)") and a dispersant (B), The dispersant (B) is a polymer containing styrene monomer units and maleic acid ester monomer units. The maleic acid ester monomer unit is a unit having a carboxyl group and one or more esters selected from the group consisting of alkoxy(poly)ethylene oxyesters and alkoxy(poly)propylene oxyesters. The ultraviolet absorber (A) having a triazine moiety preferably contains one or more selected from the group consisting of a phenyl moiety and a naphthyl moiety.

[0010] The mechanism by which the composition of the present invention can solve the problem is hypothesized as follows. The styrene-maleic acid ester polymer of the dispersant (B) is adsorbed by the aromatic rings of the styrene monomer units stacking on the phenyl and naphthyl moieties of the ultraviolet absorber (A). Furthermore, the carboxyl group of the maleic acid ester moiety acts as an electrostatic repulsion site, contributing to dispersion stability. This improves the temporal stability of the composition. In addition, the molecular chains derived from one or more selected from the group consisting of alkoxy(poly)ethylene oxyesters and alkoxy(poly)propylene oxyesters of the maleic acid ester monomer units have a moderate affinity for water, thus contributing to improved water dispersibility of the ultraviolet absorber (A) and achieving dispersion stability of the composition. As a result, in this specification, an optical lens dyeing composition is obtained in which the ultraviolet absorber (A) can be dispersed in water, enabling the dyeing of optical lenses.

[0011] <UV absorber (A)> The ultraviolet absorber (A) having a triazine moiety is a compound having one or more moieties selected from the group consisting of a phenyl moiety and a naphthyl moiety bonded to the triazine ring. The presence of phenyl and naphthyl moieties shifts the maximum absorption wavelength of light to the longer wavelength side, allowing it to absorb blue light when applied to optical lenses. The maximum absorption wavelength of the ultraviolet absorber (A) is preferably 300-450 nm, more preferably 350-450 nm, and even more preferably 350-400 nm. The maximum absorption wavelength of the ultraviolet absorber (A) is proportional to the number of phenyl and naphthyl moieties bonded to the triazine moiety. Compounds having 1-3 moieties appropriately selected from phenyl and naphthyl moieties are preferred, compounds having 2-3 moieties are more preferred, and compounds having 3 moieties are even more preferred. The phenyl and naphthyl moieties may have substituents with aromatic rings.

[0012] Examples of aromatic rings in the UV absorber (A) include phenyl, naphthyl, pyridyl, and quinolyl groups. Among these, the naphthyl group is preferred from the viewpoint of UV absorption at wavelengths of 350-400 nm.

[0013] The ultraviolet absorber (A) having a triazine moiety and a phenyl moiety is preferably a compound having a hydroxyl group on a carbon atom adjacent to the carbon atom of the phenyl moiety directly bonded to the triazine skeleton.

[0014] UV absorbers having a triazine and a phenyl moiety include, for example, 2-[4,6-di(2,4-xylyl)-1,3,5-triazine-2-yl]-5-octyloxyphenol, 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine-2-yl]-5-[3-(dodecyloxy)-2-hydroxypropoxy]phenol, reaction product of 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine and (2-ethylhexyl-glycidic acid ester), 2,4-bis"2-hydroxy-4-butoxyphenyl"-6-(2,4-dibutoxyphenyl)-1,3-5-triazine, 2,4-bis(2-hydroxy-4-butoxyphenyl)-6-(2, Examples include 4-dibutoxyphenyl)-1,3,5-triazine, 2-[4-[(2-hydroxy-3-(2'-ethyl)hexyl)oxy]-2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-[4-[(2-hydroxy-3-(2'-ethyl)hexyl)oxy]-2-hydroxyphenyl-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-(4,6-diphenyl-1,3,5-triazine-2-yl)-5-hexyloxyphenol(III-5)bisethylhexyloxyphenolmethoxyphenyltriazine, and 2,4,6-tris[4-(hexyloxy)-2-hydroxy-3-methylphenyl]-1,3,5-triazine.

[0015] The ultraviolet absorber (A) having a triazine moiety and a naphthyl moiety is, for example, a compound selected from the group consisting of the following general formulas (1), (2), and (3).

[0016] [ka] JPEG2026112633000002.jpg4740

[0017] In general formulas (1) to (3), R 1b ~R 1g , R 2a ~R 2g , and R 3a ~R 3g each independently represents any one selected from the group consisting of a hydrogen atom, a hydroxyl group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a nitrile group, a nitro group, R7, Ar1, and the groups represented by the following general formulas (4-1) to (4-3). R7 represents any one selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, and an alkenyloxy group having 1 to 20 carbon atoms, and may have a substituent of a hydroxyl group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a nitrile group, or a nitro group, and the carbon atoms of the alkyl group having 1 to 20 carbon atoms, the alkenyl group having 1 to 20 carbon atoms, the alkoxy group having 1 to 20 carbon atoms, and the alkenyloxy group having 1 to 20 carbon atoms may be connected by one or more -O-, -CO-, -COO-, -OCO-, -CONH-, or -NHCO-. Ar1 represents any one selected from the group consisting of an aryl group having 6 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, and a biphenyl group, and may have a substituent of a hydroxyl group, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkenyloxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a nitrile group, or a nitro group.

[0018] In general formulas (2) to (3), R4, R5, and R6 each independently represent any one selected from the group consisting of a hydroxyl group, R7, and Ar1.

[0019]

Chemical formula

[0020] In general formula (4-1), X1 represents any one selected from the group consisting of -CO-, -COO-, -OCO-, -CONH-, and -NHCO-, and R8 represents any one selected from the group consisting of a hydrogen atom, a hydroxyl group, R7, and Ar1. However, * in general formula (4-1) represents the bonding site with the naphthalene ring of general formulas (1) to (3).

[0021]

Chemical formula

[0022] In general formula (4-2), X2 and X3 each independently represent any one selected from the group consisting of -CO-, -COO-, -OCO-, -CONH-, and -NHCO-, R9 represents an arylene group having 6 to 20 carbon atoms, and R 10 represents R7 or Ar1. However, * in general formula (4-2) represents the bonding site with the naphthalene ring of general formulas (1) to (3).

[0023]

Chemical formula

[0024] In general formula (4-3), X4 and X5 each independently represent any one selected from the group consisting of -CO-, -COO-, -OCO-, -CONH-, and -NHCO-, R 11 represents a linear or branched alkylene group having 1 to 20 carbon atoms, or an arylene group having 6 to 20 carbon atoms, R 12 represents R7 or Ar1, and n is 1 to 20. However, * in general formula (4-3) represents the bonding site with the naphthalene ring of general formulas (1) to (3).

[0025] Preferred compounds of the ultraviolet absorber (A) having a triazine moiety are exemplified below. Note that the ultraviolet absorber (A) having a triazine moiety is not limited to the following compounds.

[0026]

Chemical formula

[0027] Among these, (A-15) and (A-18) to (A-31) are preferred for their blue light-cutting properties.

[0028] UV absorber (A) can be used alone or in combination of two or more types.

[0029] The amount of ultraviolet absorber (A) is preferably 1 to 50% by mass, and more preferably 5 to 30% by mass, of the nonvolatile content of the composition.

[0030] The volume-average particle size D50 of the UV absorber (A) is preferably 100 nm to 700 nm, and more preferably 100 nm to 500 nm. This range is preferable because it reduces aggregation of the UV absorber (A) in the composition, allowing it to be dispersed to a level close to primary particles, improving the stability of the composition and the transparency of the optical lens after dyeing. Furthermore, a smaller volume-average particle size D50 of the UV absorber (A) increases the amount of UV absorber (A) incorporated into the optical lens during dyeing, thus further improving UV absorption. The volume-average particle size D50 is determined from the volume-based particle size distribution measured using a particle size analyzer (FPAR-1000, manufactured by Otsuka Electronics Co., Ltd.) that measures by dynamic light scattering.

[0031] <Dispersant (B)> The dispersant (B) is a polymer (hereinafter referred to as "polymer") containing styrene monomer units and maleic acid ester monomer units. The maleic acid ester monomer unit is a unit having a carboxyl group and one or more esters selected from the group consisting of alkoxy(poly)ethylene oxyesters and alkoxy(poly)propylene oxyesters. Styrene monomers include styrene and other styrene-based monomers. Maleic acid ester monomer units have a carboxyl group and an ester bond.

[0032] Examples of styrene monomers include styrene, α-methylstyrene, styrene macromers, 2-methylstyrene, 4-methylstyrene, 4-n-octylstyrene, 4-methoxystyrene, 4-aminostyrene, and 4-nitrostyrene.

[0033] Styrene monomer units can be used alone or in combination of two or more types.

[0034] The styrene monomer unit content is preferably 1 to 70% by mass, and more preferably 5 to 50% by mass, of the total monomer units of the polymer.

[0035] The maleic acid ester monomer unit is a unit having a carboxyl group and one or more esters selected from the group consisting of alkoxy(poly)ethylene oxyesters and alkoxy(poly)propylene oxyesters. The maleic acid ester monomer unit is formed by polymerizing maleic anhydride and then reacting the acid anhydride group with the ester-forming compound to generate a carboxyl group and an ester. Alternatively, a maleic acid ester monomer having a carboxyl group and one or more esters selected from the group consisting of alkoxy(poly)ethylene oxyesters and alkoxy(poly)propylene oxyesters can be polymerized to produce a maleic acid ester monomer unit.

[0036] The maleic acid ester monomer unit preferably contains alkoxy(poly)ethylene oxyester and alkoxy(poly)propylene oxyester. This further improves the appropriate affinity with water.

[0037] Examples of the ester-forming compounds include compounds containing an alkoxy(poly)ethyleneoxy moiety, compounds containing an alkoxy(poly)propyleneoxy moiety, and compounds containing both an alkoxy(poly)ethyleneoxy moiety and a (poly)propyleneoxy moiety. Examples of compounds containing the alkoxy(poly)ethyleneoxy moiety include polyoxyethylene monomethyl ether, polyethylene glycol monomethyl ether, polyethylene glycol monoethyl ether, and polyethylene glycol monopropyl ether. Among these, polyethylene glycol monomethyl ether is preferred. Examples of compounds containing the alkoxy(poly)propyleneoxy moiety include polypropylene glycol monomethyl ether, polypropylene glycol monoethyl ether, polypropylene glycol monobutyl ether, and polypropylene glycol 2-ethylhexyl ether. Among these, polypropylene glycol monobutyl ether is preferred.

[0038] The content of maleic acid ester monomer units is preferably 1 to 70% by mass, and more preferably 5 to 50% by mass, of the total monomer units of the polymer (dispersant B).

[0039] Maleate ester monomer units can be used alone or in combination of two or more types.

[0040] [Other monomer units] The polymer may contain monomer units other than styrene monomer units and maleic acid ester monomer units. Other monomer units include, for example, (meth)acrylic acid ester monomers, (poly)alkylene oxy group-containing monomers, and other vinyl monomers.

[0041] (Meth)acrylic acid monomers include, for example, methyl (meth)acrylate, butyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclohexane (meth)acrylate, furfuryl (meth)acrylate, isobornyl (meth)acrylate, adamantane (meth)acrylate, 2-methyladamantane (meth)acrylate, phenyl (meth)acrylate, benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, phenoxydiethylene glycol (meth)acrylate, and phenoxypolyethylene glycol. Examples include chol(meth)acrylate, pentafluorophenyl(meth)acrylate, 2-hydroxy-3-phenoxypropyl(meth)acrylate, 2-(meth)acryloyloxyethylphthalic acid, 2-(meth)acryloyloxyethyl-2-hydroxyethyl-phthalic acid, neopentyl glycol(meth)acrylate benzoate, 4-[(6-(meth)acryloyloxy)hexyloxy]-4'-cyanobiphenyl, N-phenyl(meth)acrylamide, allylphenyl acetate, allylphenyl ether, allylphenoxyacetate, etc.

[0042] Examples of (poly)alkylene oxy group-containing monomers include polyethylene glycol allyl ether, polyethylene glycol allyl ether, polyethylene glycol polypropylene glycol allyl ether, polypropylene glycol allyl ether, methoxy(poly)ethylene glycol (meth)acrylate, ethoxy(poly)ethylene glycol (meth)acrylate, 2-ethylhexyl(poly)ethylene glycol acrylate, methoxy(poly)propylene glycol (meth)acrylate, ethoxy(poly)propylene glycol (meth)acrylate, ethoxy(poly)ethylene(poly)propylene glycol (meth)acrylate; and the like. Among these, polyethylene glycol allyl ether, polyethylene glycol polypropylene glycol allyl ether, and polypropylene glycol allyl ether represented by the following formula (1) are preferred.

[0043] Formula (1) [ka]

[0044] In formula (1), m is 0 or an integer greater than or equal to 1, n is 0 or an integer greater than or equal to 1, and m+n≧1. R1 represents a hydrogen atom or a methyl group. R2 represents an alkyl group or aryl group having 1 to 30 carbon atoms, which may have substituents. Also, when m≧1, n≧1, and m+n≧2, the bonding order of the CH2CH2O group (ethylene oxy group) and the CH(CH3)CH2O group (propylene oxy group) may be random, alternating, or in a block.

[0045] In formula (1), m is preferably 0 to 20. n is preferably 0 to 20. m+n is preferably 1 to 40. R1 is preferably a hydrogen atom or a methyl group. R2 is preferably a methyl group, ethyl group, propyl group, isopropyl group, butyl group, hexyl group, cyclohexyl group, decyl group, phenyl group, phenylcarboxyl group, or phenol group.

[0046] Other vinyl monomers include vinyl ethers such as ethyl vinyl ether, n-propyl vinyl ether, isopropyl vinyl ether, n-butyl vinyl ether, and isobutyl vinyl ether; Vinyl compounds such as 1-hexene, 1-octene, 1-decene, 1-dodecene, 1-tetradecene, 1-hexadecene, 1-octadecene, 4-vinylphenyl acetate, 2-vinylquinoline, 2-vinylnaphthalene, 4-vinylbiphenyl, 9-vinylanthracene, and 9-vinylphenanthrene; N-substituted (meth)acrylamide monomers such as (meth)acrylamide, dimethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide, N-isopropyl(meth)acrylamide, diacetone(meth)acrylamide, and acryloylmorpholine; Nitrile monomers such as (meth)acrylonitrile; alkylene oxy group-containing (meth)acrylic acid monomers such as methoxy(poly)ethylene glycol (meth)acrylate, ethoxy(poly)ethylene glycol (meth)acrylate, 2-ethylhexyl(poly)ethylene glycol acrylate, methoxy(poly)propylene glycol (meth)acrylate, and ethoxy(poly)propylene glycol (meth)acrylate; Examples include vinyl acetate and vinyl propionate, which are fatty acid vinyl monomers; and so on.

[0047] Other monomers can be used individually or in combination of two or more types.

[0048] The content of other monomer units is preferably 1 to 60% by mass, and more preferably 2 to 40% by mass, of the total monomer units of the polymer (dispersant B).

[0049] The dispersant (B) can be synthesized by known polymerization methods such as random polymerization, block polymerization, living radical polymerization, and alternating copolymerization.

[0050] The acid value of the dispersant (B) is preferably 1 to 350 mg KOH / g, and more preferably 10 to 250 mg KOH / g. By setting the acid value within the above range, the dispersion stability due to charge repulsion is further improved.

[0051] The number-average molecular weight (Mn) of the dispersant (B) is preferably 1,000 to 100,000, more preferably 5,000 to 50,000, and even more preferably 7,000 to 30,000. Furthermore, the polydispersity (Mw / Mn), obtained by dividing the weight-average molecular weight (Mw) by the number-average molecular weight (Mn), is preferably 3.0 or less, more preferably 2.0 or less, even more preferably 1.5 or less, and particularly preferably 1.2 or less. A polydispersity of 1 or more is preferred.

[0052] The content of the dispersant (B) is preferably 10 to 200 parts by mass, more preferably 20 to 150 parts by mass, and even more preferably 50 to 150 parts by mass, per 100 parts by mass of the ultraviolet absorber (A).

[0053] Examples of commercially available dispersants (B) include DISPER-BYK190 from Big Chemie, XIRAN1440 and XIRAN2625 from Polyscope, and Alastor 700 and Alastor 700S from Arakawa Chemical Corporation.

[0054] <Water(C)> The composition of the present invention may contain water (C). The water is preferably deionized water, distilled water, or purified water. The total amount of metal ions contained in the water is preferably 10 ppm or less, more preferably 1 ppm or less, and even more preferably 100 ppb or less.

[0055] The composition of the present invention can be used in combination with water (C) and a water-soluble solvent.

[0056] [Water-soluble solvent] Water-soluble solvents are water-soluble organic solvents that are miscible with water. Examples of water-soluble organic solvents include alcohols, polyhydric alcohol alkyl ethers, polyhydric alcohol aryl ethers, nitrogen-containing heterocyclic compounds, amides, sulfur-containing compounds, propylene carbonate, ethylene carbonate, and other water-soluble solvents.

[0057] Alcohols include, for example, methanol, ethanol, propanol, butanol, pentanol, 3-methoxy-3-methylbutanol, glycerin, ethylene glycol, diethylene glycol, dipropylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, 1,2-propanediol, 1,3-propanediol, propylene glycol, dipropylene glycol, tripropylene glycol, polypropylene glycol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 1,2-pentanediol, 1,3-pentanediol, 1,4-pentanediol, 1,5-pentanediol, 1,2-hexanediol, 1,3-hexa Examples include hexanediol, 1,4-hexanediol, 1,5-hexanediol, 1,6-hexanediol, 3-methyl-1,3-butanediol, trimethylolethane, trimethylolpropane, 1,2,6-hexanetriol, 1,2,4-butanetriol, 1,2,3-butanetriol, petriol, 2-ethyl-2-methyl-1,3-propanediol, 3,3-dimethyl-1,2-butanediol, 2,2-diethyl-1,3-propanediol, 2-methyl-2-propyl-1,3-propanediol, 2,4-dimethyl-2,4-pentanediol, 2,5-dimethyl-2,5-hexanediol, 5-hexen-1,2-diol, 2-ethyl-1,3-hexanediol; and others.

[0058] Examples of polyhydric alcohol alkyl ethers include ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, tetraethylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, and the like.

[0059] Examples of polyhydric alcohol aryl ethers include ethylene glycol monophenyl ether, diethylene glycol monophenyl ether, tetraethylene glycol chlorophenyl ether, ethylene glycol monobenzyl ether, ethylene glycol monoallyl ether, and the like.

[0060] Examples of nitrogen-containing heterocyclic compounds include 2-pyrrolidone, N-methyl-2-pyrrolidone, N-hydroxyethyl-2-pyrrolidone, 1,3-dimethylimidazolidinone, ε-caprolactam, and γ-butyrolactone.

[0061] Examples of amides include formamide, N-methylformamide, N,N-dimethylformamide, and so on.

[0062] Examples of sulfur-containing compounds include dimethyl sulfoxide, sulfolane, thiodiethanol, and the like.

[0063] Water-soluble solvents can be used alone or in combination of two or more.

[0064] <Carrier agent> The composition of the present invention may contain a carrier agent. Using a carrier agent facilitates the penetration of the ultraviolet absorber into the optical lens, improving the dyeing efficiency. Examples of carrier agents include aromatic compounds. Examples of aromatic compounds include alcohols having aromatic substituents such as benzyl alcohol and cinnamyl alcohol; phenolic compounds such as orthophenylphenol and paraphenylphenol; methylnaphthalene; various benzophenone compounds; monochlorobenzene, o-dichlorobenzene, m-dichlorobenzene, 1,2,4-trichlorobenzene, 1,2,5-trichlorobenzene, 1,3,5-trichlorobenzene, 1,2,3-trichlorobenzene, tetrachlorobenzene, pentachlorobenzene, hexachlorobenzene, monochloronaphthalene; and various polychloronaphthalene compounds. Among these, from the viewpoint of improving the penetration of the ultraviolet absorber, alcohols having aromatic substituents are preferred, benzyl alcohol and cinnamyl alcohol are more preferred, and benzyl alcohol is even more preferred. Carrier agents can be used alone or in combination of two or more types.

[0065] The carrier agent content is preferably 1 to 40 parts by mass per 100 parts by mass of ultraviolet absorber.

[0066] The composition of the present invention may optionally contain additives such as ultraviolet absorbers other than ultraviolet absorber (A), binder resins, surfactants, dispersing aids, defoaming agents, thickeners, and surface modifiers.

[0067] The composition of the present invention is preferably prepared by dispersing a mixture containing an ultraviolet absorber (A), a dispersant (B), water (C), and a dispersion medium. Alternatively, the composition can be prepared by adding the above-mentioned additives as needed and then dispersing or stirring and mixing the mixture. The dispersion process can be performed multiple times. The timing of adding the additives is arbitrary.

[0068] Dispersers used in the dispersion process include, for example, kneaders, ultrasonic dispersers, three-roll mills, ball mills, bead mills, and jet mills. Dispersion media include, for example, glass beads, alumina beads, and zirconia beads. The average particle size of the dispersion media is approximately 0.1 to 3 mm.

[0069] Examples of equipment used for stirring and mixing include Henschel mixers, tumbler mixers, and dispersers.

[0070] After dispersion treatment, the composition can be separated and filtered to remove coarse particles. The separation can be achieved through centrifugal separation at a gravitational acceleration of 3000 to 25000 G, and the filtration can be achieved through sintered filters, membrane filters, dead-end filtration, cross-flow filtration, etc.

[0071] The composition of the present invention exhibits excellent ultraviolet absorption and dispersibility, and maintains excellent dispersibility even after long-term storage. The composition is preferably applied to optical lenses. Optical lenses can be used in smartphones, tablet devices, notebook PCs, eyeglasses, cameras, video cameras, microscopes, telescopes, medical devices, etc. The composition described herein does not prevent the inclusion of dyes for the purpose of arbitrarily coloring resins, molded articles, etc.

[0072] <UV-absorbing optical lenses> The ultraviolet-absorbing optical lens of the present invention is a lens obtained by dyeing an optical lens with the above-mentioned optical lens dyeing composition. Preferably, the above-mentioned ultraviolet-absorbing optical lens has an ultraviolet absorber (A) and a dispersant (B) having a triazine moiety from the above-mentioned optical lens dyeing composition on at least the surface and / or inside the lens.

[0073] The present invention's method for manufacturing an ultraviolet-absorbing optical lens preferably involves dyeing the optical lens with a composition. The dyeing process should be sufficient to ensure that the composition adheres to and / or impregnates the surface of the optical lens, thereby achieving the desired ultraviolet absorption properties. Note that dyeing also includes coating.

[0074] The aforementioned dyeing can be carried out using general methods such as (1) forming a film of the composition on the surface of an optical lens using a spin coater to produce an ultraviolet-absorbing optical lens, or (2) immersing an optical lens in the composition to impregnate the lens with the composition, then removing it to produce an ultraviolet-absorbing optical lens. After coating, the lens can be dried at room temperature or using a dryer as needed. In the method for producing an ultraviolet-absorbing optical lens described herein, the optical lens is the lens before dyeing with the composition described herein. The ultraviolet-absorbing optical lens is the lens after dyeing with the composition described herein.

[0075] Examples of materials for optical lenses include polycarbonate resin, urethane urea resin, (thio)urethane resin, episulfide resin, polyamide resin, and polyester resin. (Thio)urethane resin is at least one selected from thiourethane resin and urethane resin. Among these, polycarbonate resin, urethane urea resin, (thio)urethane resin, and episulfide resin are preferred. The thickness of optical lenses should be set appropriately according to their intended use, such as in eyeglasses, microscopes, or cameras.

[0076] [Example of an embodiment] Examples of embodiments of the present invention are given below. The present invention is not limited to the following.

[0077] <1> The optical lens staining compositions described herein are optical lens staining compositions comprising a triazine moiety-containing ultraviolet absorber (A), a dispersant (B), and water (C), The dispersant (B) is a polymer containing styrene monomer units and maleic acid ester monomer units. The maleic acid ester monomer unit is a unit having a carboxyl group and one or more esters selected from the group consisting of alkoxy(poly)ethylene oxyesters and alkoxy(poly)propylene oxyesters. <2> The average D50 particle size of the aforementioned ultraviolet absorber (A) is 100 to 700 nm. <1> A composition for staining optical lenses. <3> The dispersant is contained in 10 to 200 parts by mass per 100 parts by mass of the ultraviolet absorber (A). <1> or <2> A composition for staining optical lenses. <4> <1> ~ <3> An ultraviolet-absorbing optical lens obtained by dyeing an optical lens with an optical lens dyeing composition. <5> The method for producing the optical lens staining composition described herein involves dispersing a mixture containing a triazine moiety-containing ultraviolet absorber (A), a dispersant (B), and a dispersion medium. The dispersant (B) is a polymer containing styrene monomer units and maleic acid ester monomer units. The maleic acid ester monomer unit is a unit having a carboxyl group and one or more esters selected from the group consisting of alkoxy(poly)ethylene oxyesters and alkoxy(poly)propylene oxyesters. <6> Optical lenses <1> ~ <3> Any optical lens staining composition, or <5> A method for manufacturing an ultraviolet-absorbing optical lens, comprising coating it with an optical lens dyeing composition obtained from the above. [Examples]

[0078] The present invention will be described in more detail below with reference to examples. However, the present invention is not limited to these examples. Note that "parts" refers to "parts by mass" and "%" refers to "percentage by mass".

[0079] (Number average molecular weight (Mn)) Measurements were performed using gel permeation chromatography (GPC) equipped with an RI detector. An HLC-8220GPC (Tosoh Corporation) was used, with two separation columns connected in series. Both columns were packed with two TSK-GEL SUPER HZM-N columns. The oven temperature was 40°C, THF solution was used as the eluent, and the flow rate was 0.35 ml / min. The sample was dissolved in a 1% solution of the above eluent and injected in 20 microliters. Molecular weight is expressed as polystyrene equivalent.

[0080] Uniox M-550: Polyoxyethylene monomethyl ether (manufactured by NOF Corporation, molecular weight: 550) Uniox M-1000: Polyoxyethylene monomethyl ether (manufactured by NOF Corporation, molecular weight: 1000) Poly(propylene glycol) monobutyl ether: Manufactured by Sigma-Ardrich, Molecular weight: 1000

[0081] <Synthesis of dispersant (B)> • Synthesis of dispersant (B-1) In a reaction vessel equipped with a gas inlet tube, thermometer, condenser, dropping funnel, and stirrer, 14 parts (50 mol%) of styrene, 13 parts (50 mol%) of maleic anhydride, 22 parts of toluene, and 1 part of octyl thioglycolate as a chain transfer agent were charged as a monomer mixture. After purging with nitrogen, the mixture was heated to 105°C with stirring. A mixture of 0.5 parts of dimethyl azobisisobutyrate (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., trade name: V-601) and 5 parts of MEK was added dropwise over 1 hour as a radical polymerization initiator. Subsequently, while stirring at a temperature of 85°C, a mixture of 1 part of V-601 and 10 parts of toluene was added dropwise over 6 hours, and the reaction was continued for 1 hour while maintaining the temperature at 85°C to obtain a polymer having maleic anhydride as an acid anhydride group. Next, 73 parts (50 mol%) of Uniox M-550, 50 parts of toluene, and 0.1 parts of diazabicycloundecene as a catalyst were added, and the mixture was stirred at 120°C for 6 hours to react, thereby ring-opening and half-esterifying maleic anhydride. The solvent of the resulting product was concentrated under reduced pressure to completely remove it, and a dispersant (B-1) (number-average molecular weight (Mn): 17,940) was prepared.

[0082] <Dispersants (B-2~B-10)> Dispersants (B-2 to B-10) were synthesized in the same manner as dispersant (B-1), except that the materials and masses used were changed as shown in Table 1.

[0083] [Table 1]

[0084] <Manufacturing of Dispersion Compositions> [Example 1] (Dispersion composition (C-1)) After uniformly stirring and mixing the mixture with the following composition, the mixture was dispersed using 0.3 mm diameter zirconia beads in an Eiger mill for 2 hours, and then filtered through a 0.5 μm filter to prepare the dispersed composition. UV absorber (A-1): 10.0 parts Dispersant (B-1): 10.0 parts Antifoaming agent (BYK-024, manufactured by Big Chemie Co., Ltd.): 0.2 parts Purified water: 79.8 parts

[0085] [Examples 2-20, Comparative Examples 1-2] (Dispersion composition (C-2~C-22)) Dispersion compositions (C-2 to C-22) were prepared in the same manner as dispersion composition (C-1), except that the composition and quantities of dispersion composition (C-1) were changed as shown in Table 2.

[0086] [Table 2]

[0087] <Evaluation of Dispersion Compositions> The obtained dispersion compositions were evaluated as follows. The results are shown in Table 3.

[0088] (Viscosity evaluation) The viscosity of the obtained dispersion composition was measured at 25°C and 50 rpm using an E-type viscometer (ELD-type viscometer manufactured by Toki Sangyo Co., Ltd.). The following criteria were used for evaluation. ◎: Less than 5 mPa·s - Excellent ○: 5 mPa·s or higher, less than 10 mPa·s - Good △: 10 mPa·s or more, less than 30 mPa·s (Practical range) ×: Above 30 mPa·s - Not practical for use.

[0089] (Storage stability) The obtained dispersion composition was stored in a 40°C incubator for one week to accelerate the time course, and then the viscosity was measured in the same manner as for viscosity evaluation to determine the percentage change in viscosity of the dispersion composition before and after the time course. The following criteria were used for evaluation. ◎: Change rate less than ±3% - Excellent ○: Change rate of ±3% or more, less than ±5% - Good △: Change rate of ±5% or more, and less than ±15% (Practical range) ×: Change rate of ±15% or more - Not practical.

[0090] (particle size) The volume-average particle size D50 of the obtained dispersion composition was measured using a particle size analyzer FPAR-1000 (manufactured by Otsuka Electronics Co., Ltd.). The average value of three measurements was used for the particle size. ◎: Particle size 100nm or larger, less than 300nm - Excellent ○: Particle size 300nm or larger, less than 500nm - Good △: Particle size between 500nm and 700nm (Practical range) ×: Particle size 700nm or larger - Not practical for use.

[0091] (uniformity) The uniformity of the dispersion state of the obtained dispersion composition was visually evaluated. The evaluation criteria were as follows: ○: No coarse particles visible to the naked eye. Good. △: Coarse particles can be visually confirmed. (Practical range) ×: Coarse particles have settled. Not practical.

[0092] [Table 3]

[0093] The results in Table 3 show that the compositions of Examples 1 to 20 can stably disperse the ultraviolet absorber (A) in water due to the action of the styrene-maleate polymer dispersant (B). As a result, they showed good results in viscosity, storage stability, and uniformity evaluations.

[0094] <Evaluation of optical lenses> [Example 21] 100 parts of dispersion composition C-1 were mixed with 1 part of benzyl alcohol as a carrier. The mixture was kept at a temperature of 95°C, and an optical lens "HILUX1.5" (manufactured by HOYA Corporation), made of diethylene glycol bisallyl carbonate with a refractive index of 1.50, was immersed in the mixture for 1 hour to allow it to permeate. After standing at room temperature for 5 hours, an ultraviolet-absorbing optical lens (eyeglass lens) was obtained. The following evaluations were then performed.

[0095] [Examples 22-43, Comparative Examples 3-4] An optical lens was fabricated in the same manner as in Example 21, except that the materials were changed as shown in Table 4. The results are shown in Table 4.

[0096] The refractive indices in Table 4 were obtained using the following optical lenses. 1.50: "HILUX 1.5" (manufactured by HOYA, allyl carbonate resin) 1.53: "Phoenix" (manufactured by HOYA, urethane urea resin) 1.60: "EYAS" (manufactured by HOYA, thiourethane resin) 1.67: "EYNOA" (manufactured by HOYA, thiourethane resin)

[0097] (UV absorption of the lens - 1) The transmittance of the obtained eyeglass lenses was measured using a UV-Vis spectrophotometer "U-4100" (manufactured by Hitachi, Ltd.) and evaluated according to the following criteria. ○: Transmittance of less than 5% at wavelengths of 380-400nm - Good △: Transmittance of 5% or more but less than 20% at wavelengths of 380-400nm (Practical range) ×: Transmittance of 20% or more at wavelengths of 380-400nm is unsuitable for practical use.

[0098] (UV absorption of the lens - 2) The transmittance of the obtained eyeglass lenses was measured using a UV-Vis spectrophotometer "U-4100" (manufactured by Hitachi, Ltd.) and evaluated according to the following criteria. ○: Transmittance of less than 10% at wavelengths of 400-410nm - Good △: Transmittance of 10% or more but less than 40% at wavelengths of 400-410nm (Practical range) ×: Transmittance of 400-410nm wavelength is 40% or higher. Not practical for use.

[0099] (Haze value) The obtained lenses were evaluated by measuring the haze value using a haze meter and according to the following criteria. ◎: Less than 0.2 - Very good ○: 0.2 or higher and less than 0.5 - Good △: 0.5 or higher and less than 2 (Practical range) ×: 2 or more - Not practical

[0100] (Storage stability of lenses) The obtained lenses were left to stand for up to 120 hours in an environment of 100°C, and observed with an optical microscope at 50x magnification to check for the presence of crystalline ultraviolet absorber of 0.5 mm or more within the lens. Separately, the obtained lenses were left to stand in an environment of -40°C, and the precipitates were observed in the same manner and evaluated according to the following criteria. ◎: Under all environmental conditions, one or fewer precipitates were found after 120 hours. Excellent. ○: In all environments, one or fewer precipitates after 80 hours indicates good performance. △: Under all environmental conditions, one or fewer precipitates are found after 50 hours. (Practical range) ×: In all environments, one or more precipitates are present after 50 hours. Not practical.

[0101] [Table 4]

[0102] As shown in Table 4, UV-absorbing optical lenses manufactured using compositions containing UV absorber (A) and styrene-maleate polymer dispersant (B) exhibited good UV absorption, transparency, and storage stability. On the other hand, the reason why comparative example 3, which did not use dispersant (B), showed good storage stability of haze and lenses was that no staining occurred at all.

Claims

1. A composition for staining optical lenses comprising a UV absorber (A) having a triazine moiety, a dispersant (B), and water (C), The dispersant (B) is a polymer containing styrene monomer units and maleic acid ester monomer units. The maleic acid ester monomer unit is a unit having a carboxyl group and one or more esters selected from the group consisting of alkoxy(poly)ethylene oxyesters and alkoxy(poly)propylene oxyesters, in a composition for staining optical lenses.

2. The optical lens dyeing composition according to claim 1, wherein the volume average particle diameter D50 of the ultraviolet absorber (A) is 100 to 700 nm.

3. The optical lens dyeing composition according to claim 1, comprising 30 to 200 parts by mass of the dispersant (B) per 100 parts by mass of the ultraviolet absorber (A).

4. An ultraviolet-absorbing optical lens obtained by dyeing an optical lens with the optical lens dyeing composition described in any one of claims 1 to 3.

5. A method for producing an optical lens dyeing composition, comprising dispersing a mixture containing a triazine moiety-containing ultraviolet absorber (A), a dispersant (B), and a dispersion medium. The dispersant (B) is a polymer containing styrene monomer units and maleic acid ester monomer units. A method for producing an optical lens staining composition, wherein the maleic acid ester monomer unit is a unit having a carboxyl group and one or more esters selected from the group consisting of alkoxy(poly)ethylene oxyesters and alkoxy(poly)propylene oxyesters.

6. A method for producing an ultraviolet-absorbing optical lens, comprising staining an optical lens with an optical lens staining composition described in any one of claims 1 to 3, or an optical lens staining composition obtained in claim 5.

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