COMPOSITION AND METHOD FOR MANUFACTURING ULTRAVIOLET-ABSORBING OPTICAL LENS - Patent application

A UV absorber composition with triazine or benzotriazole sites and aromatic rings, combined with acidic group-containing compounds, addresses dispersion issues in water-based systems, providing stable and transparent UV absorption.

JP7626290B1Active Publication Date: 2025-02-04TOYO INK MFG CO LTD
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Patent Information

Application Number
JP2024140737
Authority / Receiving Office
JP · JP
Patent Type
Patents
Current Assignee / Owner
Priority Date
2024-08-08
Filing Date
2024-08-22
Publication Date
2025-02-04
Estimated Expiration
2044-08-22

AI Technical Summary

Technical Problem

Conventional UV absorbers have low dispersion in water-based compositions, leading to large particle sizes, sedimentation, light scattering, and uneven distribution, resulting in low transparency and UV absorption.

Method used

A composition comprising UV absorber compounds with triazine or benzotriazole sites and aromatic rings, combined with acidic group-containing compounds, is used to enhance dispersion and stability in water, forming a uniform coating with improved UV absorption.

Benefits of technology

The composition achieves stable, transparent, and effective UV absorption by suppressing light scattering, maintaining uniform distribution, and ensuring long-term stability.

✦ Generated by Eureka AI based on patent content.

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Abstract

An object of the present invention is to provide a composition that has good stability over time, good transparency, suppresses light scattering in the visible light region, and is capable of forming a coating having good ultraviolet absorption properties. [Solution] The composition contains an ultraviolet absorber (A) having a triazine or benzotriazole moiety and an aromatic ring (but not having an acidic group), and an acidic group-containing compound (B) having a triazine or benzotriazole moiety (but excluding dyes).
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Description

[Technical field]

[0001] The present invention relates to a composition containing an ultraviolet absorber. [Background technology]

[0002] UV absorbers generally have a ring structure and are highly hydrophobic, making them difficult to dissolve in water. Therefore, when UV absorbers are processed into aqueous solutions or aqueous dispersions, they are difficult to disperse or dissolve, unlike when they are used in a solvent or without a solvent.

[0003] For example, Patent Document 1 discloses an aqueous fiber treatment composition (claimed) that contains a non-reactive ultraviolet absorber compound, an emulsifier or dispersant for the ultraviolet absorber compound, water, and optionally a polysiloxane-based product. Patent Document 2 discloses a composition containing an ultraviolet absorber, an anionic surfactant, and water (Example 8). Patent Document 3 discloses an ultraviolet absorber aqueous dispersion composition (claimed) that contains a benzotriazole-type ultraviolet absorber and a polyglycerin monoalkyl ester. Patent Document 4 discloses a fiber treatment composition (claimed) that contains an ultraviolet absorber (A) and an aromatic polycarboxylic acid derivative (B) that is an esterification reaction product of an aromatic polycarboxylic acid and a hydroxyl group-containing compound. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Application Publication No. 8-92874 [Patent Document 2] JP 2000-119261 A [Patent Document 3] JP 2009-120638 A [Patent Document 4] JP 2009-235606 A Summary of the Invention [Problem to be solved by the invention]

[0005] However, conventional aqueous dispersions of ultraviolet absorbers have low dispersion of the ultraviolet absorber, many coarse particles, and their average particle diameter is large. Therefore, the aqueous dispersions have low productivity because the ultraviolet absorber settles over time and needs to be re-stirred when used. In addition, the coating of the aqueous dispersion has low transparency because of light scattering in the visible light region due to the large average particle diameter. In addition, the aqueous dispersion has low ultraviolet absorption effect compared to the amount used because the ultraviolet absorber is unevenly distributed in the particles due to the large average particle diameter and coarse particles.

[0006] An object of the present invention is to provide a composition which has good stability over time, good transparency, suppresses light scattering in the visible light region, and is capable of forming a coating having good ultraviolet absorbing properties. [Means for solving the problem]

[0007] <1> The composition of the present invention contains an ultraviolet absorber (A) having a triazine or benzotriazole moiety and an aromatic ring (but not having an acidic group), and an acidic group-containing compound (B) having a triazine or benzotriazole moiety (but excluding dyes). <2> The mass ratio of the ultraviolet absorber (A) to the acidic group-containing compound (B) is 50:50 to 99:1. <1> Composition of. <3> The acidic group of the acidic group-containing compound (B) is a carboxy group or a sulfo group. <1> or <2> Composition of. <4> The ultraviolet absorber (A) is a compound having a naphthyl moiety. <1> ~ <3> Any composition. <5> A composition comprising: an ultraviolet absorber (A) having a triazine or benzotriazole moiety and an aromatic ring (but not having an acidic group); an acidic group-containing compound (B) having a triazine or benzotriazole moiety; and water. <6> <1> ~ <5> A method for producing an ultraviolet absorbing optical lens, comprising coating any one of the compositions onto an optical lens. Effect of the Invention

[0008] According to the present invention described above, it is possible to provide a composition capable of forming a coating material having good stability over time, good transparency, suppressing light scattering in the visible light region, and good ultraviolet absorbing properties. The present invention also provides a method for producing an ultraviolet absorbing optical lens. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0009] The composition of the present invention contains an ultraviolet absorber (A) having a triazine or benzotriazole moiety and an aromatic ring (but having no acidic group), and an acidic group-containing compound (B) having a triazine or benzotriazole moiety (but excluding dyes) (hereinafter referred to as acidic group-containing compound (B)). The ultraviolet absorber (A) of the present invention having a triazine or benzotriazole moiety and an aromatic ring (but having no acidic group) preferably has a maximum absorption wavelength in the range of 300 to 450 nm of 350 to 450 nm, more preferably 350 to 400 nm.

[0010] The mechanism by which the composition of the present invention can solve the problems is assumed to be as follows. The acidic group-containing compound (B) is a dispersing aid for the ultraviolet absorber (A), and when dispersed in water, the triazine or benzotriazole moiety adsorbs to the ultraviolet absorber (A) and the acidic group functions as a charge-repulsive site, thereby improving water dispersibility.

[0011] <Ultraviolet absorber (A)> The ultraviolet absorber (A) having a triazine moiety or a benzotriazole moiety and an aromatic ring (hereinafter referred to as ultraviolet absorber (A)) is a compound having no acidic group. The maximum absorption wavelength of the ultraviolet absorber (A) is preferably 300 to 450 nm, more preferably 350 to 450 nm, and further preferably 350 to 400 nm. The ultraviolet absorbent (A) has a triazine moiety or a benzotriazole moiety as a basic skeleton, and an aromatic ring is bonded to the basic skeleton, thereby obtaining the above-mentioned ultraviolet absorbency.

[0012] Examples of the aromatic ring of the ultraviolet absorber (A) include a phenyl group, a naphthyl group, a pyridyl group, a quinolyl group, etc. Among these, a naphthyl group is preferred from the viewpoint of ultraviolet absorption at a wavelength of 350 to 400 nm.

[0013] Examples of ultraviolet absorbers having a triazine moiety and an aromatic ring include 2-[4,6-di(2,4-xylyl)-1,3,5-triazin-2-yl]-5-octyloxyphenol, 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-[3-(dodecyloxy)-2-hydroxypropoxy]phenol, reaction products 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-(2,4-dibutoxyphenyl)-1,3-5-triazine, and 2,4-bis(2-hydroxy-4-butoxyphenyl)-6-(2,4-dibutoxyphenyl)-1,3-5-triazine. -butoxyphenyl)-6-(2,4-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-triazin-2-yl)-5-hexyloxyphenol (III-5) bisethylhexyloxyphenol methoxyphenyl triazine, and the like.

[0014] [ka] JPEG0007626290000002.jpg5143

[0015] 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 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, which may have a substituent such as 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 linked between each other via 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 such as 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.

[0016] In formulae (2) and (3), R4, R5, and R6 each independently represent any one selected from the group consisting of a hydroxyl group, R7, and Ar1.

[0017] General formula (4-1) [ka]

[0018] In the 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, provided that * in the general formula (4-1) represents a bonding site with the naphthalene ring of the general formulae (1) to (3).

[0019] General formula (4-2) [ka]

[0020] In the 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; R 10 represents R7 or Ar1, provided that * in general formula (4-2) represents the bonding site with the naphthalene ring in general formulae (1) to (3).

[0021] General formula (4-3) [ka]

[0022] In the 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. In addition, * in general formula (4-3) represents a bonding site with the naphthalene ring of general formulae (1) to (3).

[0023] Commercially available products include "KEMISORB 102" manufactured by Chemipro Chemicals, "TINUVIN 400", "TINUVIN 405", "TINUVIN 460", "TINUVIN 477-DW", "TINUVIN 479", and "TINUVIN 1577" manufactured by BASF Japan, "ADK STAB LA-46" and "ADK STAB LA-F70" manufactured by ADEKA Corporation, and "CYASORB UV-1164" manufactured by Sun Chemical Company.

[0024] Examples of ultraviolet absorbers having a benzotriazole moiety and an aromatic ring include 2-(5-methyl-2-hydroxyphenyl)benzotriazole, 2-(2-hydroxy-5-t-butylphenyl)-2H-benzotriazole, octyl-3[3-tert-butyl-4-hydroxy-5-(5-chloro-2H-benzotriazol-2-yl)phenyl]propionate, and 2-ethylhexyl-3-[3-tert-butyl-4-hydroxy-5-(5-chloro-2H-benzotriazol-2-yl)phenyl]propionate. A mixture of 2-[2-hydroxy-3,5-bis(α,α-dimethylbenzyl)phenyl]-2H-benzotriazole, 2-(3-t-butyl-5-methyl-2-hydroxyphenyl)-5-chlorobenzotriazole, 2-(3,5-di-t-amyl-2-hydroxyphenyl)benzotriazole, 2-(2'-hydroxy-5'-t-octylphenyl)benzotriazole, 5% 2-methoxy-1-methylethyl acetate and 95% benzenepropanoic acid, 3-(2H-benzotriazol-2-yl)-(1,1-diphenyl ether)-2H-benzotriazole. methylethyl)-4-hydroxy, C7-9 side chain and straight chain alkyl ester compounds, 2-(2H-benzotriazol-2-yl)-4,6-bis(1-methyl-1-phenylethyl)phenol, 2-(2H-benzotriazol-2-yl)-6-(1-methyl-1-phenylethyl)-4-(1,1,3,3-tetramethylbutyl)phenol, 2-(2'-hydroxy-3',5'-di-t-amylphenyl)benzotriazole, 2-(3-t-butyl-5-methyl-2-hydroxyphenyl)-5-chlorobenzaldehyde, 2-(2-hydroxy-5-t-octylphenyl)benzotriazole, 2-ethylhexyl-3-[3-t-butyl-4-hydroxy-5-(5-chloro-2H-benzotriazol-2-yl)phenyl]propionate, 2-(2H-benzotriazol-2-yl)-6-dodecyl-4-methyl-phenol, 2-(2H-benzotriazol-2-yl)-3-t-butylphenol, 2-(2H-benzotriazol-2-yl)-6-(1-methyl-1-phenylethyl)-4-(1,1-3,3-tetramethylbutyl)phenol, 2-(2H-benzotriazol-2-yl)-3-methylphenol, 2-(2H-benzotriazol-2-yl)-6-dodecyl-4-methyl-phenol, 2,2'-methylenebis[6-(2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol], etc.

[0025] Examples of commercially available products include "TINUVIN P", "TINUVIN PS", "TINUVIN 109", "TINUVIN 234", "TINUVIN 326", "TINUVIN 328", "TINUVIN 329", "TINUVIN 360", "TINUVIN 384-2", "TINUVIN 900", "TINUVIN 928", "TINUVIN 970", "TINUVIN 99-2", and "TINUVIN 1130" manufactured by BASF Japan Ltd., "ADEKA STAB LA-29" manufactured by ADEKA Corporation, and "RUVA-93" manufactured by Otsuka Chemical Co., Ltd.

[0026] The ultraviolet absorbents (A) can be used alone or in combination of two or more kinds.

[0027] <Acidic group-containing compound (B)> The acidic group-containing compound (B) is a dispersing aid for the ultraviolet absorber (A), and the triazine or benzotriazole moiety is adsorbed to the ultraviolet absorber (A), and the acidic group acts on water dispersibility. The acidic group-containing compound (B) is a compound other than a dye. Since the acidic group-containing compound (B) does not have a tinting power like a dye, for example, when the composition of this specification is used together with a transparent resin to produce a molded product, the transparency of the molded product is not easily impaired. The ultraviolet absorber (A) also does not have a tinting power. In this specification, the tinting power refers to the ability to be colored chromatically. The acidic group-containing compound (B) is adsorbed to the ultraviolet absorber (A) regardless of whether the basic skeleton of the ultraviolet absorber (A) is a triazine moiety or a benzotriazole moiety, and good water dispersibility is obtained. The reason for this is that the triazine moiety and benzotriazole moiety of the acidic group-containing compound (B) are planar structures, and therefore are sufficiently adsorbed to the planar structures of the triazine moiety and benzotriazole moiety of the ultraviolet absorber (A). Therefore, even in the subsequent dispersion process, stirring process, and aging conditions of the composition, the acidic group-containing compound (B) is unlikely to be detached from the ultraviolet absorber (A) and the dispersibility is unlikely to be impaired. In addition, when the acidic group-containing compound (B) has the same skeleton as the ultraviolet absorber (A), it is adsorbed by the ultraviolet absorber (A), and even better water dispersibility is obtained.

[0028] Examples of the acidic group of the acidic group-containing compound (B) include a carboxyl group, a sulfo group, a phosphate group, etc. Among these, from the viewpoint of dispersibility, a carboxyl group and a sulfo group are preferred, and a sulfo group is more preferred.

[0029] Examples of the acidic group-containing compound (B) are given below. It goes without saying that the acidic group-containing compound (B) is not limited to the exemplified compounds.

[0030] [ka]

[0031] The acidic group-containing compound (B) may be used alone or in combination of two or more kinds.

[0032] The mass ratio of the ultraviolet absorber (A) to the acidic group-containing compound (B) is preferably from 50:50 to 99:1, and more preferably from 70:30 to 95:5, from the viewpoint of dispersibility.

[0033] The content of the ultraviolet absorber (A) is preferably from 5 to 50 mass %, more preferably from 5 to 30 mass %, and even more preferably from 5 to 20 mass %, of the non-volatile content of the composition.

[0034] The composition of the present invention is preferably a dispersion of an ultraviolet absorber (A) (having no acidic group), an acidic group-containing compound (B), and water. A solvent can be used in place of or in combination with the water. The composition can also be prepared by kneading without using water or a solvent.

[0035] Water is the dispersion medium. In this specification, the dispersion medium may be a solvent other than water. The solvent may be a water-soluble solvent or a non-aqueous solvent. Examples of the water-soluble solvent include ketones such as acetone, diacetone alcohol, and γ-butyrolactone; alcohols such as methyl alcohol, ethyl alcohol, isopropyl alcohol, and n-propyl alcohol; glycol ethers such as propylene glycol monomethyl ether, methyl cellosolve, and ethyl cellosolve; and highly polar solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide. Examples of the non-water-soluble solvent include ketones such as methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc., esters such as ethyl acetate, butyl acetate, propylene glycol monomethyl ether acetate, etc., and hydrocarbons such as hexane, toluene, etc. These may be used alone or in combination of two or more kinds.

[0036] The composition of the present invention may contain additives such as dispersants, binder resins, surfactants, dye derivatives, antifoaming agents, thickeners, and surface conditioners, as necessary.

[0037] The composition of the present invention can be prepared, for example, by dispersing the ultraviolet absorber (A), the acidic group-containing compound (B) and water. If necessary, the above-mentioned additives can be added and mixed by stirring to prepare the composition. The dispersion treatment can be carried out multiple times. The timing of adding the additives is optional.

[0038] Examples of dispersing machines used in the dispersion treatment include a kneader, an ultrasonic dispersing machine, a three-roll mill, a ball mill, a bead mill, and a jet mill.

[0039] After dispersion, the composition can be separated or filtered to remove coarse particles. The separation may be performed by centrifugation at a gravitational acceleration of 3,000 to 25,000 G, and the filtration may be performed by filtration using a sintered filter or a membrane filter, dead-end filtration, cross-flow filtration, or the like.

[0040] The composition of the present invention has excellent UV absorption and dispersibility, and is excellent in dispersibility even after long-term storage, and therefore can be suitably used for various applications such as various resin molded bodies, synthetic rubber, fiber materials, inks, cosmetics, and optical lenses. Optical lenses can be used in smartphones, tablet terminals, notebook PCs, glasses, cameras, video cameras, microscopes, telescopes, medical devices, and the like. The composition of the present specification may contain a dye to arbitrarily color resins, molded bodies, and the like.

[0041] <Optical lenses> In the method for producing an ultraviolet absorbing optical lens of the present invention, the composition is preferably applied to the optical lens. It is sufficient that the composition adheres to the surface of the optical lens or is impregnated into the interior of the optical lens by the application, thereby obtaining the desired ultraviolet absorbing properties. Note that the application also includes an impregnation method.

[0042] The coating can be performed by a general method such as (1) forming a coating 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 a composition, impregnating the lens with an ultraviolet absorber (A) and an acidic group-containing compound (B), and then removing the lens to produce an ultraviolet absorbing optical lens. After coating, the lens can be left at room temperature or dried using a dryer or the like as necessary. In the method for producing an ultraviolet absorbing optical lens of the present specification, the optical lens is a lens before the composition of the present specification is coated. Also, the ultraviolet absorbing optical lens is a lens after the composition of the present specification is coated on the optical lens. EXAMPLES

[0043] The present invention will be described in more detail below with reference to examples. However, the present invention is not limited to these examples. In addition, "parts" means "parts by mass" and "%" means "% by mass".

[0044] <Ultraviolet absorber (A)> [ka] [ka] [ka] [ka] [ka]

[0045] <Acidic group-containing compound (B)> [ka] [ka] [ka] [ka]

[0046] <Production of Dispersion Composition> [Example 1] (Dispersion composition (C-1)) A mixture of the following composition was stirred and mixed uniformly, and then dispersed in an Eiger mill using zirconia beads having a diameter of 0.5 mm for 3 hours, and then filtered through a 0.5 μm filter to prepare a dispersion composition. Ultraviolet absorber (A-1): 10.0 parts Acidic group-containing compound (B-1): 1.0 part Defoamer (BYK-024, manufactured by BYK-Chemie): 0.3 parts Purified water: 88.7 parts

[0047] [Examples 2 to 22, Comparative Examples 1 to 4] (Dispersion composition (C-2~C-26)) Dispersion compositions (C-2 to C-26) were prepared in the same manner as dispersion composition (C-1), except that the blending of dispersion composition (C-1) was changed to the compositions and amounts shown in Table 1.

[0048] [Table 1]

[0049] The terms in the table are as follows: Additive A: Dye derivative Compound represented by the following chemical formula [ka]

[0050] Additive B: Dispersant Efka PX 4701 (BASF Japan, 100% non-volatile content)

[0051] <Evaluation of Dispersion Composition> The resulting dispersion composition was evaluated as follows, and the results are shown in Table 2.

[0052] (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.) and evaluated according to the following criteria. ◎: Less than 5mPa·s, extremely good ○: 5 mPa·s or more, less than 10 mPa·s Good △: 10mPa·s or more, less than 30mPa·s Practical range ×: 30 mPa·s or more Not practical

[0053] (Storage stability) The obtained dispersion composition was stored in a thermostatic chamber at 40°C for one week to accelerate aging, and then the viscosity was measured in the same manner as in the viscosity evaluation, and the viscosity change rate of the dispersion composition before and after aging was calculated. Evaluation was based on the following criteria. ◎: Change rate is less than ±3% - Very good ○: Change rate is ±3% or more, less than ±5% Good △: Change rate is ±5% or more and less than ±15%. Practical range ×: Change rate is ±15% or more. Not practical.

[0054] (UV absorbency-1) The concentration of the obtained dispersion composition was adjusted with purified water so that the non-volatile content of the dispersion composition was 300 ppm, and then the absorbance of the dispersion composition was measured using a UV-visible spectrophotometer "U-4100" (manufactured by Hitachi, Ltd.) and evaluated according to the following criteria. ○: Absorbance at 380 nm is 1.0 or more. Good △: absorbance at 380 nm is 0.5 or more and less than 1.0 (practical range) ×: absorbance at 380 nm is less than 0.5. Not practical.

[0055] (UV absorbency -2) The concentration of the obtained dispersion composition was adjusted with purified water so that the non-volatile content of the dispersion composition was 300 ppm, and then the absorbance of the dispersion composition was measured using a UV-visible spectrophotometer "U-4100" (manufactured by Hitachi, Ltd.) and evaluated according to the following criteria. ○: Absorbance at 400 nm is 0.5 or more. Good △: absorbance at 400 nm is 0.2 or more and less than 0.5 (practical range) ×: absorbance at 400 nm is less than 0.2. Not practical.

[0056] (uniformity) The dispersion state of the obtained dispersion composition was visually evaluated for uniformity, and 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.

[0057] [Table 2]

[0058] From the results in Table 2, the dispersion compositions of Examples 1 to 16 can stably disperse the ultraviolet absorbent (A) in water due to the action of the acidic group-containing compound (B). As a result, they showed good results in the evaluation of viscosity, storage stability, and uniformity. Among them, the combination of triazines or benzotriazoles was more preferable because the ultraviolet absorbent (A) and the acidic group-containing compound (B) were strongly adsorbed. And, as the acidic group of the acidic group-containing compound (B), a sulfo group having a strong charge repulsion force was particularly preferable. In addition, from the viewpoint of ultraviolet absorption, a dispersion composition containing an ultraviolet absorber having a triazine moiety or a benzotriazole moiety and an aromatic ring was good, and from the viewpoint of absorbance at 400 nm, a dispersion composition containing an ultraviolet absorber having a triazine moiety and a naphthalene ring was particularly good.

[0059] <Optical lens evaluation> [Example 23] Dispersion composition C-1 was kept at a liquid temperature of 95°C, and an optical lens "HILUX1.5" (manufactured by HOYA Corporation) made of diethylene glycol bisallyl carbonate and having a refractive index of 1.50 was immersed and penetrated for 1 hour. It was left at room temperature for 5 hours to obtain an ultraviolet absorbing optical lens (lens for glasses). The following evaluations were then performed.

[0060] [Examples 24 to 47, Comparative Examples 5 to 8] An ultraviolet absorbing optical lens was produced in the same manner as in Example 23, except that the materials in Example 23 were changed as shown in Table 3. The results are shown in Table 3.

[0061] [UV absorption] The ultraviolet absorbency of the obtained ultraviolet absorbing optical lens at a wavelength of 400 nm was measured using a UV-visible spectrophotometer "U-4100" (manufactured by Hitachi, Ltd.) to measure the transmission spectrum, and the ultraviolet absorptivity was calculated from the transmittance of light at a wavelength of 400 nm using the following formula, which was taken as the ultraviolet absorbency. UV absorption rate = [1-400 nm light transmittance] x 100 (%)

[0062] [Table 3]

[0063] The refractive indices in the table were determined using the following optical lenses. 1.50: "HILUX1.5" (HOYA, allyl carbonate resin) 1.53: "Phoenix" (HOYA, urethane urea resin) 1.60: "EYAS" (HOYA, thiourethane resin) 1.67: "EYNOA" (HOYA, thiourethane resin)

[0064] As shown in Table 3, the ultraviolet absorbing optical lens produced using the composition containing the ultraviolet absorber (A) and the acidic group-containing compound (B) has good ultraviolet absorption properties and can be suitably used as an ultraviolet absorbing eyeglass lens.

Claims

1. A composition containing an ultraviolet absorber (A) having a triazine or benzotriazole moiety and an aromatic ring (but not having an acidic group), an acidic group-containing compound (B) having a triazine or benzotriazole moiety (but excluding dyes), and water.

2. The composition according to claim 1, wherein a mass ratio of the ultraviolet absorber (A) to the acidic group-containing compound (B) is 50:50 to 99:

1.

3. 2. The composition according to claim 1, wherein the acidic group of the acidic group-containing compound (B) is a carboxy group or a sulfo group.

4. The composition according to claim 1 , wherein the ultraviolet absorber (A) is a compound having a naphthyl moiety.

5. A method for producing an ultraviolet absorbing optical lens, comprising coating the composition according to any one of claims 1 to 4 onto an optical lens.

Citation Information

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