JPS59107301A - Plastic dimming lens - Google Patents

Abstract

PURPOSE:To obtain the titled dimming lens having superior dimming performance, scratch resistance and light resistance by coating a plastic lens with a mixture of the hydrolyzate of a specified silicon compound with an epoxy compound, a curing catalyst and finely powdered phototropic glass. CONSTITUTION:A coating composition is prepd. by mixing the hydrolyzate (A) of a silicon compound represented by the formula (where R<1> is vinyl, amino, imino, epoxy, methacryloxy, phenyl or SH; R<2> is H, 1-6C hydrocarbon, alkoxyalkyl or 1-4C acyl; (a) is 0-2; (b) is 0 or 1; and a+b<=2), e.g. vinyltrimethoxysilane with an epoxy compound (B) such as ethylene glycol diglycidyl ether and a curing catalyst (C) such as BF3. Finely powdered phototropic glass is dispersed in the composition, and the surface of a transparent plastic lens of acrylic resin or the like is coated with the composition and dried to obtain the desired plastic dimming lens.

Description

Detailed Description of the Invention: The present invention improves dimming performance, scratch resistance, light resistance, and chemical resistance by applying a highly hard coating film containing finely powdered 7-ototopic glass to the surface of a synthetic resin lens. This invention relates to a synthetic resin photochromic lens that has excellent surface properties such as being dyeable with 9 disperse dyes.

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. In Japan, the share of plastic lenses is increasing year by year. On the other hand, the market share of resin lenses made of diethylene glycol bisallyl carbonate (hereinafter referred to as 0R-3q), which is the mainstream of plastic lenses, is said to be 50% in the United States;
It is said that growth has almost stopped after reaching 0%. This is thought to be due to the ease with which the OR-39 resin looks when compared to glass, and the second reason is that the OR-39 lens does not have a photochromic lens that exhibits excellent dimming performance. Currently, there is only one lens on the market that exhibits blue photochromic properties. The light control performance of this lens is not satisfactory compared to the light control performance of a glass lens in both the coloring speed and the fading speed. Almost the same thing can be said about photochromic lenses made of thermoplastic resin. On the other hand, the mainstream consumer's desire for coloring photochromic lenses is for the lens to change from colorless to brown or gray due to absorption of light. In other words, it is no exaggeration to say that the only thing that satisfies synthetic resin photochromic lenses is heat.

In view of the above points, the present inventors have completed a synthetic resin photochromic lens that has excellent dimming performance, abrasion resistance, solvent resistance, light resistance, impact resistance, and dyeability with disperse dyes. As a result of intensive research, we have arrived at the present invention.

That is, the present invention is a synthetic resin photochromic lens characterized by containing finely powdered phototropic glass in a coating composition containing the following A, B, and 0.

J.A. General formula R4Si (OR3)4-cL-6 (where R1 is an organic group containing at least one selected from vinyl, amine, imino, epoxy, methacryloxy, phenyl, and SH group, R2 is hydrogen, and has 1 to 6 carbon atoms) a hydrocarbon group or a vinyl group, R3 is a hydrocarbon group having 1 to 5 carbon atoms,
an alkoxyalkyl group or an acyl group having 1 to 4 carbon atoms,
α is 0, 1 or 2, b(l-1:o or 1, and a hydrolyzate of one or more silicon compounds represented by a+b≦2).

B, at least one selected from epoxy compounds 0, F
fJ! Specific examples of the silicon compound as component A used in the present invention include vinyltrimethoxysilane, vinyltriethoxysilane, ethylenediaminopropyltrimethoxysilane, r
-aminopropyltrimethoxysilane, r-glycidoxypropyltrimethoxysilane, r-glycidoxypropyltriethoxysilane, γ-glycidoxypropylmethyldimethoxysilane, β-glycidoxyethyltrimethoxysilane, β-(5,4-epoxycyclohexyl)ethyltrimethoxysilane, r-(3゜4-epoxycyclohexyl)propyltrimethoxysilane, γ-methacryloxypropylmethyldimethoxysilane, phenyltrimethoxysilane, r-mercaptopropyltrimethoxy Silane.

Tetramethoxysilane, tetraethoxysilane.

Tetraproxysilane, tetrabutoxysilane.

Methyltrimethoxysilane, methyltriethoxysilane, methyltripropoxysilane, methyltriptoxysilane, ethyltriethoxysilane.

Examples include propyltriethoxysilane, methyltriethoxysilane, and butyltriethoxysilane.

In order to hydrolyze the above-mentioned silane compound, it can be easily obtained by using water or an aqueous solution of hydrochloric acid, sulfuric acid, acetic acid, phosphoric acid, etc. in the presence or absence of a well-known solvent such as alcohol. can. In addition, each of the silane compounds of A may be used alone or in a mixture of two or more, and those in which the corresponding alkoxy group has been previously hydrolyzed or partially dehydrated and condensed are essentially equivalent. , the same effect can be obtained even if these are included.

Epoxy compounds of component B include (poly)ethylene glycol, (poly)propylene glycol, glycerol, neopentyl glycol, 1,6-hexadiol, trimethylolpropane, pentaerythritol,
Mono-, di-, tri-, and tetraglycidyl ale of polyhydric alcohols such as diglycerol, sorbitol, and bis7er/-A (OH groups may remain) and double bonds of unsaturated fatty acids such as oleic acid. Part or all of it is epoxidized.

Various epoxy curing agents can be used as the zero-component curing catalyst. For example, B F 3 , S n O
t4,5nO14, Zn012, Fe01B, aluminum chelate compound, and HOL, HBr, H
OtOsH3''04scarboxylic acid, sulfonic acid, etc.

Examples of solvents that may be included in the coating composition include alcohols, ketones, esters, Or it can be used as a mixed solvent of two or more kinds. Further, if necessary, surfactants, thixotropic agents, organic polymers, inorganic silica fine particles, etc. can be added to impart properties necessary as a paint.

``Phototropic glass containing silver halide (silver chloride, silver bromide, silver iodide, and mixtures thereof) was used, and copper oxide was used as a photosensitizer. Fo)) Lobby glass can be manufactured using a well-known method.
This advantage in the present invention! The phototropic glass thus obtained is crushed into approximately 2,000 mesh pieces and dispersed in a coating composition. When used in eyeglass lenses, since it is coated on the surface, unlike materials that are dispersed into the lens, it is possible to obtain a uniform intensity of light regardless of the thickness of the lens. Since it is a fine powder, it is uniformly dispersed in the coating composition.

The coating liquid made of the above-mentioned mixture is applied by a commonly used method such as a dipping method, a spray coating method, a spin coating method, or a flow coating method.
A cured film is formed by heating and drying. The heating humidity and heating time are determined by the properties of the base material. The thickness of the obtained cured film is preferably 1.5 to 30μ, and 1
, 5μ or less, sufficient dimming performance cannot be obtained, and 30
When the thickness is μ or more, the dimming property is sufficient, but the effect of thickening cannot be expected on effects such as scratch resistance.

The coating composition obtained in this way is made of a transparent resin such as polycarbonate resin, acrylic resin, 0R-59 resin, polyester, etc., and is applied to the surface of the lens, and has excellent transparency and dimming performance, and is necessary for practical use. A synthetic resin photochromic lens having excellent scratch resistance, chemical resistance, light resistance, and hot water resistance can be obtained.

The present invention will be explained in more detail with reference to Examples below, but the present invention is not limited thereto.

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

Light control performance: Using a photochromic lens light control lens tester HE-223 (manufactured by Hasegawa Biko), those with an average light attenuation rate of 30% or more in the visible range were evaluated as good in one test.

Scratch resistance: *oooo A load of 1 to 9 was applied with steel wool, and the surface was rubbed 10 times back and forth, and the degree of scratching was divided into the following grades and evaluated.

A: There is no field at all within the icInX3cm range.

B: 1 to 10 scratches are made within the above range.

0: 10 to 100 sticks are formed within the above range.

D: There are countless scratches, but no smooth surface remains.

E: No smooth surface remains due to scratches on the surface.

Adhesion of coating film; by cross-cut tape test,
That is, cross-cut with a knife on the surface of the coating, lmm
After making 100 1mm squares and attaching cellophane adhesive tape to them, peel off the tape and make 10° squares.
The number of squares that did not peel off was expressed as the number of squares that did not peel off.

Hot water resistance: The state of the film was examined after being immersed in boiling water for 1 hour.

Heat resistance: The state of the film was examined after it was kept in a hot air drying oven at 130°C for 2 hours.

Chemical resistance: 95% ethanol, acetone, 5% sulfuric acid aqueous solution, 1% hydroxide) The state of the film was examined after 48 hours of immersion in IJum aqueous solution.

Dyeability with scattering dyes: Disperse Terrasil Black B (manufactured by Chilgaiki) 2f in warm water at 85°C, immerse the lens in this solution for 5 minutes, and the average light attenuation rate in the visible range is 25% or more. was rated as good.

Example 1 (1) Preparation of hydrolyzate of γ-glycidoxypropyltrimethoxysilane and tetramethoxysilane.

γ-Glycidoxyprobyltrimethoxysilane in a reaction vessel equipped with a stirrer and a cooling tube.

110 parts of tetramethoxysilane, 80 parts of tetramethoxysilane, and 230 parts of isopropyl alcohol were added thereto, and 76 parts of a 0.05 N nitric acid aqueous solution was added at room temperature while stirring vigorously. Stirring was further continued at room temperature for 1 hour to effect hydrolysis. Thereafter, stirring was stopped and the mixture was aged at room temperature overnight.

(2) Preparation and coating of paint To the hydrolyzate obtained in (1), 1,6-hexanesiol diglycidyl ether (Evolite 1600, Kyoeisha Yushi Kagaku 7 = 115 parts, stannous chloride 1.2 parts, 0.2 parts of silicone surfactant was added, stirred at room temperature for 30 minutes, and further ground into 2000 meshes of phototropic glass (A) (composition shown in Table 1) 90 as described below.
The mixture was stirred for 1 hour to obtain a mixed dispersion, which was used as a paint. This paint was applied to an OR-39 lens by the dipping method at a polishing rate of 15 crn/pongee, and cured in a hot air dryer at 80°C for 30 minutes and then at 120°C for 90 minutes. The thickness of the film after curing was 5 μm, and the film had a light yellowish tinge but was transparent. Table 2 shows the characteristics of the lens.

Example 2 The same procedure as in Example 1 was carried out except that 60 parts of a 0.01 N nitric acid aqueous solution was added to 100 parts of r-glycidoxypropyltrimethoxysilane, 60 parts of vinyltrimethoxysilane, and 200 parts of ethyl heptasol at room temperature. A hydrolyzate of γ-glycidoxypropyltrimethoxysilane and vinyltrimethoxysilane was obtained. To this solution, 100 parts of ethylene glycol diglycidyl ether (Evolai) 40 E #manufactured by Kyoeisha Oil and Fat Chemical Co., Ltd. + B7sO (OtHs)
1 part of phototropic glass (B) was added, stirred for 1 hour, and ground into 2000 meshes (composition shown in Table 1).
Add 70 parts and disperse, and add 0.2 parts of the flow control agent "Disbaron AQ4200-1ON, Kusumoto Kasei".
and mixed with a homogenizer at 2000 rpm for 2 hours to prepare a paint. The obtained coating liquid was immersed in SM Engineering KO Neulord under the same conditions as in Example 1, dried, and cured. The obtained lens was a transparent lens with a slight yellow tinge, and the thickness of the coating was 6 μm. Table 2 shows the characteristics of the lens.

Example 3 100 parts of β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 35 parts of methyltrimethoxysilane
15 parts of Aerosil (manufactured by Nippon Aerosil Co., Ltd.), about 10 to 50 mμ, and 180 parts of isopropyl alcohol without stirring. 44 parts of Q 5 N sulfuric acid aqueous solution was added, and hydrolysis was carried out in the same manner as in Example 1.

To the thus obtained liquid, 80 parts of trimethylolpropane triglycidyl ether (Evolite 10QMF, manufactured by Kyoeisha Yushi Kagaku) and 1.5 parts of tin tetrachloride were added and stirred at room temperature for 30 minutes. 60 parts of Tropy Glass (0) (composition shown in Table 1) was added and stirred vigorously at room temperature to obtain a mixed dispersion, which was used as a paint.

The above coating liquid was applied to a lens obtained by injection molding of polymethyl methacrylate by a dipping method (pulling speed: 837 M), and dried and cured at 60° C. for 1 hour and at 80° C. for 6 hours. The obtained lens is a transparent lens with a slight yellowish tinge.
The thickness of the coating film was 8μ. Table 2 shows the characteristics of the lens.

Claims (1)

[Claims] (1) Synthetic resin dimming R1 is characterized by containing finely powdered Japanese pine folio glass in a coating composition containing A, B and C below. epoxy. An organic group containing at least one selected from methacryloxy, phenyl, and SH group R2 is hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, an alkoxyalkyl group, or 1 to 4 carbon atoms
acyl group, α is O or 1 or 2, b is 0 or 1
A hydrolyzate of one or more silicon compounds represented by α+6≦2). B, at least one selected from epoxy compounds; C0 curing catalyst