JPS5978302A - Synthetic resin photochromic lens - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a photochromic lens made of a synthetic resin having a surface hardness of 1 and having an antifogging function and excellent stainability with a disperse dye and durability.

With the enactment of FDA standards in the United States in 1972, the safety of eyeglass lenses was reviewed, and safer plastics began to be used as lens materials in place of inorganic glass. Even in Japan, the share of plastic lenses is increasing and is said to be in the 30s, at λ1. In addition to the safety, lightness, and fashionability (dyeability) of plastic, numerous manufacturers have conducted extensive research to add functions such as anti-reflective coating, hard coating, hard anti-reflective coating, and rust prevention. This is thought to be because the products were rejected one after another.

On the other hand, the main Mt of plastic lenses is diethylene glycol pisallyl carbide (hereinafter referred to as a R-3).
The market share of plastic lenses (referred to as 9) in the United States is said to be 50%11, and it is said that the market share has almost stopped growing after reaching 50%. This 1
．． It is speculated that this is due to the fact that it is more easily scratched compared to the glass of the O'FI-'39 lens, and also because of the photochromic lens, which has an excellent dimming function in the 1l-tOB-39 lens. Currently, only lenses exhibiting dark blue photochromism are commercially available. The a11jl light performance of this lens is not satisfactory compared to the light control performance of a glass lens in terms of light attenuation rate, coloring speed, and fading speed.

Almost the same thing can be said about photochromic lenses made of plastic resin. On the other hand, when it comes to the coloring of photochromic lenses, the majority of consumers desire a change from colorless to brown or gray due to absorption of light. It is no exaggeration to say that there are no satisfactory optical lenses made of thin synthetic resin.

Furthermore, fogging of glasses is uncomfortable for eyeglass wearers and can sometimes be dangerous. Helping lenses to prevent health problems are on sale from companies such as Hattori Watch Store, but no photochromic lenses with anti-fog functionality have been released yet.

In view of the above points, the inventor of the tree decided to stop i1. fc (As a result of intensive research to complete a synthetic resin g-shine lens that has dyeability with long-lasting disperse dyes, 4L scratch resistance, permanence resistance, and R-single light function, we found that Synthetic resin V photochromic lenses with durability, scratch resistance, anti-fog function, and photochromic function were discovered by combining a component that has strong properties and a component that has photochromic properties. The present invention relates to a synthetic resin photochromic lens having an anti-fog function and coated with a coating composition f consisting of the following A%B and C components.

A General formula P″b R”a　-Si-(oFIE　4□.

(However, F1 vinyl, amino, imino, epoxy,
An organic compound containing at least one compound selected from methacryloxy, phenyl, and phenyl.
~5 carbon, bihydrogen group, ano 1 koxyalkyl group, acylno to sentence 1 ~, a, 0, 1, 2.
A hydrolyzate of one or two or more silicon compounds having a bliO concentration of 1 and a≦2.

B A compound having a hydroxyl group with a molecular weight of 100 or more.

Next, each component constituting the coating composition of the present invention will be described.

The silicon-11 compound of component A in the present invention is an important component for improving scratch resistance, and specific examples thereof include vinyltrimethoxysilane, vinyltriethoxysilane, ethylenediminoproxytrimethoxysilane, γ - Ding minopropyltrimethoxysilane.

γ-Dalisidoxypropyltrimethoxysilane, γ-glycidoxypropyltriethyltriethyltriethoxysilane, γ-glycidoxypropylmethyldi4toxysilane, β-glycidoxypropyltrimethoxysilane, β-(p, A -epoxycyclohegycyl)ethyltrimethoxysilane, γ-(3
%4-Evogysicyclohexylnopropyltrimethoxysilane, γ-methacrylogycibrobyltrimethoxysilane, γ-methacryloxypropylmethyldimethoxysilane, fluorhiltriethoxysilane, γ-merbunoptopropyltrimethoxysilane, Tetramethoxysilane, tetraethoxysilane, tetrapro-4-oxysilane, tetrabutoxysilane, methyl-11-methoxysilane, methyltriethoxysilane, methyltripropoxysilane/
, methoxyA/t11) ethoxysilane, ethyltriethoxysilane, fluoroyltriethoxysilane, butyltriethoxysilane, and the like.

As is well known, the hydrolysis P+i of the above 79711 compound can be obtained by adding water, nitric acid, phosphoric acid, alcohol ((1st class water RIV), in the presence or absence of a solvent such as alcohol, etc. It can be easily done by machining.Also, silane f1 of A
'The compounds are 1114 each! It is also possible to use a mixture of 2 or more layers of lI, and those that have been hydrolyzed with the corresponding Ryolkoxy group in advance, '+7j k: J partially dehydrated shoes, and those that have been partially dehydrated are also equivalent in terms of wood quality. , even if these are included, the same result can be obtained.

Siran f above father? The hydrolyzate of the compound has a particle size of 5~
It is also possible to add finely divided silica of 2 EI Om'p.

The compound having a hydroxyl group as component B is an essential component for imparting dyeability with disperse dyes and antifogging properties.Specific examples include (poly)ethylene glycol, (poly)propylene gel 11col, (poly) Ethylene oxide + tV on one or more hydroxyl groups of glycerol, and polyhydric alcohols such as glycerin, trimethylolpropane, diglycerin, benthae lythritol, adonitol, sorbitol, and inositol? Additives, polyvinyl alcohol, polymeric hydroxyethyl methacrylate, etc. having more than 100 molecules can be mentioned. A particularly preferred range for the molecular weight of polyhydric fluorol is 200 to 3,000. It is also possible to mix two or more of these polyhydric alcohols.

Examples of silver halide for C include silver bromide and silver chloride.

Iodor (Hl) is preferred.

In addition to the above components, it is also possible to add Ou and monovalent or divalent metal ions.
-1 alcohol gi, ketan A1 ester IF, nitrides, cellosolves, halogens, carboxylic acids, aromatic compounds, etc. Or it can be used as a mixed solvent for Type 2 buried soil.

X If necessary, hardeners, catalysts (particularly useful when component B' of component A contains an epoxy group), surfactants, thiisotropic agents, and organic polymers can be added to impart properties necessary for paints. .

The method for applying the coating liquid, which consists of the above components A, E, G, solvent, and other additives, is to apply the coating liquid by a commonly used method such as a dipping method, a spray method, a spin coating method, or a flow coating method. By heating and drying, it becomes a hard film.

The heating temperature and heating time vary depending on the properties of the base material. It is preferable that the thickness of the obtained hard fF film is 1 to 50μ.
If it is less than 1 μm, satisfactory surface abrasion resistance cannot be obtained, and it is difficult to fully demonstrate the properties of the film.
Even if the film thickness is greater than μ, the effect of increasing the film thickness cannot be expected.

In addition, it is also possible to pre-treat the lens surface with two types of bleach or active gas, acid, alkali, etc. in order to improve the adhesion to the fabric being coated. It is.

The coating composition thus obtained is applied to the surface of a lens made of a transparent resin such as polycarpomate resin, acrylic resin, 0R-39# resin, polystyrene, etc., to improve transparency, antifogging performance, and light control performance. ＞%h, and it is also possible to obtain a synthetic resin spotlight lens that has the essential scratch resistance, durability, dispersion, and dyeability.

The present invention will be explained in detail below with reference to Examples, but it is not limited to these examples.

Note that parts in the examples indicate parts by weight. Moreover, the method shown below was used to evaluate the film.

Dimming performance, Photochromic Lens Dimming Lens Tester HE-225 (manufactured by Sega Wabiko Co., Ltd.) was evaluated as good if the average dimming cold 1 in the visible range was 30 coefficients or higher in one test.

Scratch resistance: The surface was rubbed 10 times under a load of 1 kg with 5oooo steel and wool, and the degree of scratching was divided into the following grades and evaluated.

A: There are no burns in the iko and llh of 1cInx5crn.

B: 1 to 10 wood scratches within the above range.

C: 10 to 100 scratches are made within the above range.

D: There are immobile scratches, but a smooth surface remains.

E: Due to scratches on the surface, no smooth surface remains.

Tightness of coating film: Based on cross-cut tape test.

That is, cross-cut with a knife on the surface of the coating, and
Make 100 m x 1 square ft, leave cellophane adhesive tape on it for a few days, then peel off the tape and remove 100 squares from among the 100 squares. I held it and displayed it.

Anti-fog performance: Those that did not cause fogging when exposed to an atmosphere at a temperature of 5 to 25 degrees Celsius and a humidity of 60% were rated as good.

Hot water resistance: The state of the film after being immersed in boiling water for 30 minutes. Chemical resistance: The state of the film after being immersed in 95% ethanol for 2+1 hours.

Dyeability with disperse dyes Disperse 2g of Niterasil Black B (manufactured by Ciba Geigy) in warm water at 85°C, immerse the lens in this solution for 5 minutes, and evaluate the quality if the average #light index in the visible range is 25% or less. And so.

Example 1 (1) 9+ of hydrolyzate of γ-clindoxyprobyltrimethosesisilane and tetramethoxysilane 4.
(r.

110 parts of γ-glycidoxypropyltrimethoxysilane, 80 parts of tetramethoxysilane, and 200 parts of ethyl cellosolve were placed in a reaction vessel equipped with a stirring device and a cooling tube, and the mixture was stirred vigorously until the temperature was reduced to 0.05N at room temperature. Nitrogen was added to the solution in a nitric acid water bath (76 parts), and stirring was continued for 1 hour at room temperature to effect hydrolysis. Thereafter, stirring was stopped, and the mixture was aged at room temperature overnight.

(2) Paint preparation and coating The hydrolyzate obtained in (1) contains polyethylene glycol (molecules -tJ5on) 65FJ, 200 parts of ethyl cellosolve, 1 part of stannous chloride, and 0 silicone surfactants.
．． Add 2 parts, stir at room temperature for 30 minutes, and then reduce the average particle size to
35 parts of silver bromide of omμ was added and stirred for 1 hour to obtain a mixed dispersion, which was used as a paint. This paint was dipped into SF2 KO Blacks (lens made by OFI-39) at a pulling rate of 20.
cm/-, and hardened fP by heating in a hot air dryer at 80°C for 50 minutes and then at 120°C for 90 minutes. hard f[later demand 11
Table 1 shows the properties of the lens, which had a pale yellow tinge but was transparent.

Example 2 γ-Glinodocybrovirtrimethogynosilane 100M
, vinyl trimethogiciplan 6 og B, 200 parts of ethyl cellosolve and 60 parts of 0.01 N nitric acid aqueous solution
A hydrolyzed product of γ-glycidoxib-biltrimethogine silane and pyrutrimethogine-silane was obtained in the same manner as in Example 1, except that 10% of the compound was added. Add to this solution polyoxyethyl fhisorbitol (60 parts with a molecular weight of 80,
Methyl cellosolve 150 parts, B F s O (C fowlHh
> Add 1 part of silver iodide, stir for 1 hour, disperse 20 parts of 50-100 mμ silver iodide, add 20 parts of silicone surfactant, and remove 20 parts with a homogenizer.
n (mixed for 1 hour at rpm to form a paint. All of the body fluid obtained was applied to Polycarbo f, -t sunglasses.
Dipping, drying, and hardening were performed under the same conditions as in fi3H Example 1. The lens obtained was a transparent lens with a slight color tint.The characteristics of the lens are shown in Table 1.

Example 10 parts of β-(31,a-ehophocycyclohexyl)ethyltrimethoxysilane, 35 parts of methicyto 11 methoxysilane, 15 parts of γ-rosil of about 10 to 50 mμ (
Nippon Aerosil Co., Ltd.), Inprohil Alcohol 180
0.0% without stirring. o5N (add AA part of a saturated acid aqueous solution and perform hydrolysis in the same manner as in Example 1) ◎ To the thus obtained solution, 70 parts of polyvinyl alcohol (molecular weight: 900, If9S), 50 parts of water, and methyl cellosolve were added. Add 150 parts and 1.5 parts of JH Zinc for 30 minutes at room temperature!
The AO section of the V steel was placed under the vortex of the enrichment chamber, and the mixture dispersion was 0, and 4 materials were obtained.

The sunglasses obtained by pultrusion molding of polymethyl methacrylate were coated with the female liquid by dipping and dried at 60 DEG C. for 1 hour and at 80 DEG C.A for 1 hour. The obtained lens was a transparent lens with a slight yellow tinge. Table 1 shows the %tj characteristics of l/lens.

Example 1 γ-Metac 1) Roxiprobilt 1) 9 parts of Methgocinelan 1A, 93 parts of Tetraetya Disilane, Isopropyl alcohol 11Q 1191+% Sili: 17 series b'+
Then, put 07 parts of the fh sex agent into the prepared J6 volume container (ii; This solution was aged for 2A hours at room temperature.
u, 7 parts, polymer hydroacetylmethac II
L'-) (min-i-chi-6rl[1) 65 copies, about 5
The mixture was vigorously stirred for 1 hour in a 0 mμ odor fl-button 55-g chamber for 1 hour to obtain a dispersion mixture. The obtained coating P is S E
It is applied to IKO/・Erod by the dipping method, dried in the same article 1'lZ= as in Actual Example 1, and hardened (heath, high refractive index tone with anti-fog function)゛(゛lens (i- Table 1 shows the characteristics of the obtained lens.

Table 1

Claims (1)

[Claims] (1) A synthetic resin photochromic lens having an anti-fog function, characterized in that it is coated with a coating composition consisting of the following symbols A, B, and C components. A General formula Bri R'a B i (OB"') 4. (However, Pl is an organic material containing at least one glaze such as vinyl, amino, imino, epoxy, methacryloxy, phenyl, etc.) ? is a water group, a carbon number of 1 to 6 carbon f? hydrogen group, a vinyl group, py is a hydrocarbon group of 1 to 5 carbon atoms, an alkoxyargyl group, a ash group of 1 to t, a [Hydrolyzate B of silicon compound represented by 1 size 1 size 2.b 0 x 1, where a+b≦2) or 211 (or more) A compound having a hydroxyl group with a molecular weight of 100 or more・C halogen.