JPS5948701A - Dimming lens made of synthetic resin - Google Patents

Abstract

PURPOSE:To obtain a lens made of a synthetic resin having superior dimming performance and transparency, and good surface characteristics, by coating the surface of the lens made of a transparent resin with a film of a compsn. contg. two specified kinds of org. silicon compds. and silver halide. CONSTITUTION:A coating material is prepared by feeding 67pts. compd. having formula I (R<1> is an org. group, such as vinyl; R<2> is 1-6C hydrocarbon group; (a) is 1 or 2; (b) is 0 or 1; (a)+(b)<=2), a compd. having formula II (R<4> is H or 1-6C hydrocarbon; R<5> is 1-5C alkoxyalkyl; and (c) is an integer of 0-2), and 35pts. isobutanol into a reactor, adding 77pts. hydrochloric acid of 0.05N at room temp. to hydrolyze the mixture, while violent agitation is continued during and after the reaction, aging it after stop of agitation for 24hr, and then, adding a silicone type surfactant to the hydrolyzate with stirring, and finally 9pts. silver bromide having 100mum average particle size with stirring. The lens film formed by coating it with such a coating material provides a dimming lens made of synthetic resin having good dimming performance and high transparency, etc., and superior abrasion resistance, etc.

Description

Detailed Description of the Invention The present invention provides improved dimming performance, scratch resistance, light resistance, chemical resistance, etc. by applying a highly hard coating film containing silver halide to the surface of all five-ring resin lenses. Blowing: # Also relates to a synthetic resin photochromic lens having surface characteristics.

The safety of eyeglass lenses was reviewed in 1972 with the adoption of FDA standards in the United States, and safer synthetic resins began to be used as lens materials in place of inorganic glass. In Japan, synthetic resin lenses are increasing year by year.
Air is expanding. On the other hand, the ratio of lenses made of diethylene gelicol bisallyl carbonate (hereinafter abbreviated as 0R-39) resin, which is the mainstream of synthetic resin lenses, is said to be about 50% in the United States;
It is said that the glass stops elongating once it reaches 1%/).
It is speculated that the OR-59L/lens is a photochromic lens that exhibits excellent dimming performance.

This is the only lens on the market that exhibits blue photochromism. The light control 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. The same thing can be said about photochromic lenses made of thermoplastic resin. On the other hand, the mainstream consumer's request for coloring photochromic lenses is to change from colorless to brown or gray due to original absorption. Tip 9: Combined DI It is no exaggeration to say that there is nothing I am satisfied with about photochromic lenses made of resin lenses.

In view of the above points, the present inventors have developed a synthetic resin photochromic lens having excellent photochromic performance, scratch resistance, solvent resistance, light resistance, and impact resistance. As a result of intensive research, we have arrived at the present invention described below.1 That is, the present invention is a conventional method in which silver halide is added to a coating composition containing the following (7) A and B. of·
It is a 6-inch and 53-inch synthetic resin lens.

R1 Povinyl, propyl, butyl, amino.

Imino, Gridki7. at least one organic group selected from methacryloquine, phenyl, and SH group; R2 is hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, or a vinyl group; R3 is a hydrocarbon group having 1 to 5 carbon atoms; -γrucoquin-rlkyl group or monoγnru group with 1 to 4 carbon atoms, a is 1'i or 2, b (is 0 or 1, and a -4-
b≦2), one type of silicon compound is a hydrolyzate of two or more types.

Skin General formula R'c B i -R54-0 (in the formula,
R4 is hydrogen or a hydrocarbon group having 1 to 6 carbon atoms, R5 (1
Hydrocarbon group having 1 to 5 carbon atoms, alkoxyalkyl group, -
or an acyl group having 1 to 4 carbon atoms;

Specific examples of the silicon compound used in the present invention include vinyltrimethane silane, vinyltrimethane silane, ethylenediminoprobyltrimethanesilane,
γ-Aminopropyl trimethoxine, γ-Glyndquin propyltrimethoxine, γ-Glyndquin propyltrimethoxy 77, γ-Glydquipropylmethyldimethoxy silane, β-Glyndquin ethyltrimethoxy 7, β -(3,4-epoquininclohexyl)ethyltritquine 7ran, γ-(5゜4-epoquinencrohexyl)furobyltrimethoxy/nran, γ
-methacryloquine probiltrimethoquine 7ran, γ-methacryloquine brobylmethyldimethogine 7ran, phenyltrimethquine 7ran, γ-mercaptopropyltrimethquine 7ran, etc. can be mentioned.

Further, specific examples of the silicon compound of component B include tetramethquine 7ran and tetraethquine 7ran.

Tetrapropoxine run, Tetraethquine 7 run.

Methyltrimethquine, methyltriethquine, methyltripropoquine, methyltryptoquine, ethyltriethquine, silane.

Examples include propyltriethoxy 7ran, butyltriethoxy 77ran, and the like.

In order to hydrolyze the above-mentioned 7-ranium compound proboscis, as is well known, in the presence of fusing alcohol etc., ma/ζ is in the non-ordered presence, water or water 'FJ' such as hydrochloric acid, sulfuric acid, acetic acid, phosphoric acid etc. It can be easily obtained by using tN. Also, A, B
The 7-ranium compound of
A mixture of the above may be used, and a mixture containing the above-mentioned mixtures may also be used. Solvents that may be included in the coating composition include alcohols, ketones, esters, ethers, tenorosolves, norogenides, carboxylic acids, and aromatic compounds. !
I+! l4 (il- can be given, among these,
1st edition 1st or 2nd floor! It can be used as a mixed solvent for soil. If necessary, it is possible to add compatible polymers, curing catalysts, and surfactants to these materials to impart the milling properties, viscosity, drying properties, etc. necessary for the paint. .

Silver halides include silver bromide and silver chloride.

Iodized silver can be used, and beautified silver is preferred.

The coating liquid consisting of the above-mentioned mixed edges can be applied by any of the common methods such as immersion, spraying, spin coating, flow coating, coating, etc. This is determined by the properties of the substrate.It is preferable that the thickness of the cured film is +rii~5Uμ. Trench shield, 1μ or less 0)
In the case of 1-1: T4 resistance, it is difficult to fully demonstrate the performance of the film because the damage is not overcome, and even if the film thickness is 30μ or more, the effect of increasing the total film thickness cannot be expected. .

In this way, 14 years of coaching and 1
j7! Of course 1-1, polycarbonate (σ(I!), acrylic, C, R-59 resin, polystyrene, etc.)
1. Excellent transparency, optical rotation performance, practical use and must-have oxidation resistance, chemical resistance, and 5 cm.

16; Synthesis with 1 heat 4, 11 prefecture-made photochromic lenses.

The present invention will be explained in more detail by way of example below.
The uninventiveness is 151 (fixed round thing and 1・f).

In addition, the part that is currently being implemented is the city floor capital. The method shown in ]- was used to evaluate the amount of damage.

3 Shukou jt'iU: Photochromino cleanse old Shu)
“Otsu Lens Tester HE-223 (Hasegawa Picault Co., Ltd.)
Momme) f: Used, the average attenuation rate in the visible range is 6 in one test.
0 received [Those above were considered good.]

[Resistance] Ceramic damage: A load of I Kg was applied with #0O00 steel wool, and the surface was rubbed 10 times back and forth, and evaluated by dividing it into the stages of hot-temperature alloy machining.

A: No burns occur within the range of 1on x 5m.

B: 1 to 10 scratches within the above range.

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

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

1): Due to the coating on the surface, no smooth surface remains.

Coat armpit adhesion 1st grade: Based on cross force notebook test. In other words, use a knife to cross-cut the face of the 112 people to make >100 squares of 1 x 1 x g, and then put cellophane or tape on top of it, then peel off the tape and make 100 squares. It is expressed by the same number of squares that do not peel off.

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

Heat resistance = 1 after storage in hot air drying oven at 130℃ for 2 hours
(Check out the status of Kasumi.

llI+chemical properties: immersed in 95% ethanol, acetone, 6% sulfuric acid aqueous solution, and 1% sthorium hydroxide aqueous solution for 48 hours (the state of the film after A was examined).

Actual sister example 1゜(1)
Control of hydrolyzate of orchid, tetra 7j, and quince f'
Into a reactor equipped with a stirrer, γ-grindquinprovil trimethquine 7 runs 67'jf') + tetramethquine 7 runs I U 1 part + 135 parts of isopropyl alcohol were charged, and the mixture was stirred vigorously at room temperature with 0.0. 05
77 parts of salt water was added to the mixture, and υ11 parts of water were added, and the mixture was kept at room temperature for an additional hour and a half.

After that, the stirring was completely stopped, and the hole was aged for 1 day and night at room temperature.(2)
Adjustment of paint and painting ()
1 part, add 0.2 parts of silicone surfactant, and add 30 parts of silicone surfactant at room temperature.
After stirring for 1 minute, 9 groups of silver bromide with an average particle size of 100 mμ were added, and the mixture was stirred with a homogenizer at 20,000 rpm for 1 hour.
A mixed dispersion was obtained and used as a paint. This paint is 5EIKO
Black, X (cR-sq lens), N, erX method (
The coating was applied at a pulling rate of 20 cm/jth), and heated 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 3 μm, and the film was transparent although it had a faint yellow tinge. Table 1 shows the characteristics of the lens.

Example 2 γ-gly7doxypropyltrimethoxysilane 141i
(S, 142 parts of 0.01N hydrochloric acid bath solution was added to 61 parts of tetramethquinone and 180 parts of methyl cellosolve at room temperature with stirring.The following steps were carried out in the same manner as in Example 1). A hydrolyzate of Grindquinproviltrimethoxysilane and tetramethoxysilane was added.To this vinegar solution, 1 part of lead chloride and 0.4 part of chloride surfactant were added.
After stirring at room temperature for 1 hour, silver iodide having an average particle size of 50 mμ was dispersed and stirred for 60 minutes to obtain a *liquid. The resulting coating, made entirely of polycarbonate, was immersed, dried, and cured under the same conditions as Example 1. The obtained lens is a bright t/lens with a slight yellowish tinge, and the film thickness is
It was 5.6μ. Table 1 shows the characteristics of the lens.

Example 6 97 parts of β-(3,4-ehoquinencrohexyl)ethyltrimethoxy 7rane, 16 parts of methyltrimethine silane, 15 parts of Aerosil of about 50 nμ (Nippon Aerosil (manufactured by Kiki), Tetrafitokin After adding 4.5 parts of titanium and stirring at room temperature for 4 hours, water was added.

After dropping 4.5 parts over 10 minutes with strong stirring, 24 parts at room temperature.
It was left to mature for some time.

To the solution thus obtained, 7 parts of silver bromide of approximately 50 mμ was added and stirred at room temperature with a homogenizer at 20,000 rpm for 60 minutes to form a coating solution. The coating was applied using the dipping method (pulling speed i 0t14/acid) at 60°C for 1 hour.
It was dried and cured at aO 0 C for 6 hours. The lens has a light yellowish tint to it. : It was a transparent 1% lens, and the thickness of the coating was 25μ. Table 1 shows the characteristics of the lens.

Example 4 γ-methacryloquinepropyltrimethquine silane 149
1 part, 83 parts of tetraethoxysilane, 155 pL of isopropyl alcohol, and 0.7 parts of licon-based surfactant were placed in a reaction vessel equipped with a stirrer, and 80 parts of 0.05 N aqueous hydrochloric acid solution was added all at once while stirring at room temperature. In addition, 1 more
Stir for hours. Aged this g at room temperature for 24 hours, added 12 parts of silver bromide of about 50 mμ, stirred at room temperature for 1 hour,
A dispersion mixture was obtained. The thus obtained f″ coating liquid was applied to a 5EIKO Highroad lens by the dipping method (pulling speed 5 cm/m), dried and cured under the same conditions as Example 1, and high refractive index dimming. A lens was obtained. The obtained f''L lens had a slightly yellowish, transparent coating, and the thickness of the coating was 2.5 μm. The characteristics of the lens are shown in Figure 1.

Table 1゜Applicant for Kyo-Senju Suwa Seikosha Co., Ltd. Agent Ben [1st Priest, Saido Legal Procedures Amendment Export] Showa 5-ken August 18, 1988 Patent Application No. 157852 Yumi 2, Kyomei Name: Synthetic resin photochromic lens 3, relationship to the case of the person making the correction Applicant: 2-4-1 Nishi-Shinjuku, Shinjuku-ku, Tokyo (256) Suwa Seiko Co., Ltd. 4 Agent: Representative Director Tsuneya Nakamura 150 2-6-8-5 Jingumae, Shibuya-ku, Tokyo, Number of inventions increased by amendment Procedural amendment (voluntary) 1, Specification 4, Shiroshita 71) et al., line 1 [B, General formula R' c-8i -h' 4-c-l
, r B, general formula R' c-8i (O
R') Apply pressure to 4-cl.

Groups 2 and 4 (Line 55i "Gold component used in the present invention" Corrected to [component A used in the present invention]. .

6. In the 16th line of the 8th line of the specification, it says, ``The part in progress indicates the hi'part.'' It is replaced by ``In addition, the real flu 1γri Kō no Miyako beats the 147 losing part.

”.

4. Lines 7 to 8 of Specification 12 [Actual Mjiri 113 B-(6,4-ehoquinecyclohexyl)J] ``Implemented 6° Stirring device a was added to 11 #f. Counter pressure, 1?0 parts of methyl cellosolve in Taninobu, B-(5,4-evo-thousandicyclohexyl)
”.

Claims (1) A synthetic anti-fat anti-slip lens characterized by containing silver halogen in a coating composition containing the following A and B (().

R1 havinyl, propyl, butyl, amino.

Imino, glycidoxy. Methacryloxy.

] An organic group containing at least one selected from earth and SH groups, R2 is hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a vinyl group, and R3 is a hydrocarbon group having 1 to 5 carbon atoms. ,
an alkoxyaryl group or an acyl group having 1 to 4 carbon atoms;
ai1 or 2, b is 0 sun or 1, and a -1-
A hydrolyzed product of one or more silicon compounds represented by b≦2).

B, -1 throw bar 92 S i, -1 (C small') 4-C
(In the formula, R4 is hydrogen or a hydrocarbon group having 1 to 6 carbon atoms,
R5 is carbon u, a hydrocarbon group having 1 to 5 carbon atoms, alkyl dialkyl 2IIi8 or an acyl group having 1 to 4 carbon atoms, and C is O
1 or 2 or more hydrolysates selected from the silicon compounds represented by (an integer of 2 to 2).

6-

Claims (1)

[Claims] (1) A photochromic lens made of a synthetic resin patented in that the following A, Bi gold-containing coating composition contains silver halogenide. R1 is vinyl, propyl, butyl, amino. Imino, Darishidokin, and Metakurikuchikin. +i'iso group containing at least one selected from phenyl and SH group; R2 is hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, or a vinyl group; R3 is a hydrocarbon group having 1 to 5 carbon atoms; alkoxyalkyl; group or an acyl group having 1 to 4 carbon atoms, a is 1 hole is 2, b (is 0 or 1, and a+b
≦2) A hydrolyzate of mono- or di- or more silicon compounds. B, General formula R'c-8i-R54-CC In the formula, R4 is hydrogen or a hydrocarbon having 1 to 6 carbon atoms, and B5 is 1 carbon number.
-5 hydrocarbon groups, alcogine alkyl groups, or acyl groups having 1 to 4 carbon atoms, C is an integer of θ to 2) or a 21- or more-fold hydrolyzate.