JPS5946623A - Plastic lens - Google Patents

Abstract

PURPOSE:To obtain a photochromic lens where the resistance to wear is improved, by coating the surface layer with a composition containing an organic silane compound and/or its hydrolyzed material and a photochromic material. CONSTITUTION:The thickness of a coating film and the concentration of the photochromic material are adjusted to obtain a desired final transmittance, and photochromic materials are selected to obtain a desired color. Thus, the photochromic lens is not affected by chemicals and is difficult to damage. For the silicone coating composition, the method of the U.S. patent number 2404357 or the Patent Publication No.-Sho. 57-2735, or the like is adopted. Materials mentioned in Applied Physics Vol.39 No.11 or Industrial Materials 29(10) are used as photochromic materials. Further, molybdic acid, amino-acid, dithizone-Hg- polymer, or the like is used as materials whose capacity is improved in respect to the sensitivity of color development and the optical degradation. Salts such as a silver halide and copper halide can be added to the hard coat composition as it is or in the state where they are contained in a glass matrix or by making them into a slurry.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention C is a photochromic material that has excellent scratch resistance and has the property that when there is a lot of ambient light, the light absorption increases, and when the amount of ambient light is low, the absorption degree decreases. The present invention relates to a plastic eye continuation lens that has the properties of plastic.

The safety of eyeglass lenses was reviewed in 1972 with the adoption of FDA standards in the United States, and safer plastics began to be used as lens materials instead of inorganic glass. In Japan, the share of plastic lenses is increasing year by year. - Diethylene glycol bisallyl carbonate (hereinafter referred to as CR-39), which is the mainstream of plastic lenses.
The market rate for lenses made of A4 resin is approximately 5U in the United States.
%It is said that. Although plastic lenses have the above-mentioned advantages, it is assumed that the following two reasons are why plastic lenses do not replace inorganic glass lenses. That is, plastic lenses are inferior in scratch resistance compared to inorganic glass, and the other is that there are no plastic lenses that exhibit excellent photochromic performance. Currently, there is only one lens on the market that exhibits blue photochromism. The dimming performance of this lens is not satisfactory compared to that of glass lenses in terms of light attenuation rate, fading speed, and fading speed. The same thing can be said about photochromic lenses made of thermoplastic resin. on the other hand,
Consumers' requests for the coloring of photochromic lenses are mainly for a change from colorless to brown or gray depending on the LFI absorption of light. Tsume9go J3+i
It is not excessive to say that there are no satisfactory photochromic lenses made of resin lenses.

A highly profitable technology has been developed for inorganic glass photochromic eyeglass lenses, such as US Pat. No. 3,197,396, and various products have actually been commercialized. Regarding plastic cleansing, a few methods have been disclosed (for example, Japanese Patent Laid-Open No. 52-15288).
7, II-! 1: Kaisho 5S-121412), but the former cannot obtain sufficient d degree and it is difficult to make the surface completely W@, and the latter cannot be applied to thermosetting plastics such as 0R-39. It is impossible, and it is virtually impossible to produce a spectacle lens with a multilayer structure like the one in the embodiment due to cost and technical constraints. The biggest reason why it is difficult to produce photochromic plastic lenses like Q is that plastic is sensitive to heat. It is believed that this method cannot be used at any time, and that a photochromic material blade capable of dispersing a plastic base material for IL (LTM) such as cR59 has not been developed.

Therefore, with the aim of obtaining a photochromic lens that improves the poor abrasion resistance, which is a drawback of plastic lenses, as a result of intensive studies, we found that a photochromic substance lj! It was of course discovered that the object could be achieved by dispersing the particles, leading to the present invention.

That is, the present invention involves a plastic lens whose coating layer is coated with a composition containing an organic compound and/or a hydrolyzate thereof, and 7 otochromic substances gold.

The advantages of the present invention can be summarized as follows.

(1) By adjusting the thickness of the coating ID1a and the thickness of the photochromic substance, the desired M final transmittance (transmittance when no change in absorbance is observed when irradiated with light with a photochromic lens tester) can be obtained. is obtained.

(2) By selecting photochromic materials and using one or more types, it is possible to develop the desired color1.
By using a group of photochromic organic compounds in A5b, 42+, it is possible to create a 7<< color range.

(3) (]J, In (2), the surface is hard I
I'm so stiff in M that I can't get into the medicine.
Not easy to get to.

Therefore, silicon-based coating compositions for achieving the present invention include, for example, the US Q'-'j N'r No. 2,
4 I] No. 4.357, No. 3.429.846, and Special Publication No. 57-2735. 52-13818. 56-1
5743 etc. can be used. Get 1ζ, commercially available Nuricon type no-toko-toy'1
．． 'j, can also be used for one history.

On the other hand, examples of photochromic materials include substances described in Applied Physics V01.39 Tomb 11, 1υ39 (1970) and Kogyo (-4 Phase, 29 (10), 56 (1981). , as a product with improved performance in terms of color development sensitivity and light deterioration,
Molybdate amines disclosed in No. 485, J.
, Appl, Po'1m, Sci.

17.745 (1973), dithizone-1 (g polymer, etc.) can be used. Among these inorganic substances and organic substances, silver halogenide and/or copper halogenide, etc. The material, either by itself or while still incorporated in the glass matrix, can be added to the hard coat composition by the pulverizing method or by slurrying with a suitable solvent.

The coating liquid is mixed with the photochromic injection material in the D liquid obtained by the method described in the patent. At this time, surfactants, chirotropy agents, organic polymers, inorganic fine particles, metal powders, curing catalysts, and ultraviolet absorbers may be added as necessary.

The coating liquid made of the above-mentioned mixture is applied by a commonly used method such as dipping, spraying, spin coating, flow coating, etc., and is then heated and dried to form a cured viIQ. The heating temperature and heating time are determined by the properties of the base material. The thickness of the obtained cured film is preferably 1 to 60μ, and if it is less than 1μ, satisfactory scratch resistance cannot be obtained and it is difficult to fully demonstrate the performance of the film. 6
Even if the film thickness is less than 0μ, the effect of decreasing the film thickness cannot be expected.

No. 1 obtained in this way. The coating composition is polycarbonate II't1 resin, acrylic resin, 0R
-591 By coating the lens surface made of transparent resin such as liquor fat or polystyrene, transparency and light control 1i1:
Excellent performance, scratch resistance, and excellent quality that are necessary for practical use.
It is possible to obtain a composite resin light control lens having 0 old light and 1 anti-thermal water properties.

EXAMPLES Hereinafter, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited thereto. Note that parts in the examples indicate parts by weight. Additionally, the method shown below was used to determine the +i'F value of the coating.

Dimming performance: Using Photochromic Lens Dimming Lens Tester HE-223 (manufactured by Hasegawa Picault Co., Ltd.), the average dimming rate in the Machishiri area was 60% or more in one test, and the dark reaction-C original transmission box was Those who returned were considered good.

Scratch resistance: A load of IK9 was applied with #ouuu steel wool, and the surface was scratched 1txL for 10 times, and the degree of scratching was evaluated according to the following grades.

A: There are no burns within the four 1cm x 6cm radius.

B: 1 to 10 positives within the above range.

C: 10 to 100 scratches were found within the above 11 areas.

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

E: One scratch on the surface, no smooth surface remaining.

Adhesion of coating film: Based on cross cut tape test.

In other words, cut the surface of the ruptured membrane with a knife. Loss cut and IMXlm square Make 100 pieces and put cellopha on top. After applying one more piece of adhesive tape, Peel off the loop and make 100 squares. Also, the individual squares that do not peel off. It was displayed.

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

Heat resistance: After storage for 2 hours in a hot air drying oven at 16℃℃
Check the state of r+Q.

IAII drug 1 raw: 95% ethanol, acetone, 6%
IAe acid aqueous solution, 4% sodium hydroxide in a water bath, 4%
The state of the film after 8 hours of dt was examined.

Impact Resistance/Metal In accordance with FDA standards, a so-called steel ball drop method was used to drop a 16.21 inch ball from a height of 127 cm, and test whether the lens would break 7 times when it fell downward. Example 1 γ-Grindkinpropylmethyldiethoxychloride 77 was added to a 12 glass reaction vessel equipped with a stirrer and a cooling tube.
124 parts of run was added, and while stirring, 18 parts of a 0.05N acid aqueous solution was added. After reacting at 40°C for 1 hour, methanol-dispersed colloid (catalyst chemical 1 scoop methanol licage gel, solid content 30%) 135 tt [S, aluminum acetylacetonate 4.5 yen ft S fI:'
In addition, 4.5 parts of a thiocarbazonate polymer of P-acrylamidophenylmercury was mixed with 50 parts of dimethylformamide and a solution prepared by SM-mixing was gradually added to In 1ζ.
. At this time, liquid m was pale orange in color. Here, 0.0
2 parts of silicone surfactant (Nippon Unicar)
7006'') and Phenyl Sero Tsurbuta↑;b were mixed to prepare a paint.The viscosity measured by a B-type viscometer was 5 centiboise.

This paint was applied to an 0R-39 lens ((□□□Suwa Kozue Kosha Pasei Co., Ltd.) using the immersion method, with a pulling speed history of 2 U.
It was coated at cs/min and heated and cured in an air drying oven at 80°C for 1 hour and then at 130°C for 2 hours.

The 4I-treated lens had a pale orange color, but when irradiated with a photochromic lens tester, it changed to dark red or brown, and returned to its original color within 1 minute, showing good photochromic performance. . The characteristics are shown in Table 1-f.

Example-2 Into a glass reactor equipped with a stirrer at f+tight, 80 parts of (2,3 evoki 7 propoquine) methyltrimethogine 7 run,
Mix 72 parts of tetramethoxysilane and 20 parts of prinzyl methacrylate, and γ-rays from 0o6U are mixed with I x 10
'Irradiate at room temperature for 2 hours at R/Hr to obtain a liquid,
Bath solution of isopropyl alcohol and methanol 1:1 40
part, 66 parts of 0.1N hydrochloric acid, persalt f, 0.5 part of acid, and 2.1 parts of 2-(2',4'-dinitrobenzyl)pyridine.
Part, silicone-based surfactant VL agent and flow control agent (Kusumoto Chemical Industry →.

Sedispa a 7 A Q 42 U C1-1014
) ', c) Add a small amount and use it as a paint. This material was applied in advance to 0R-394 with alkaline water/I'Sl (de-+1'α cleaning) using the υ dipping method, and placed in a hot air drying oven for 90 minutes.
It was heat-guarded at 110°C for 1 hour and 2 hours at 110°C. Obtained 7+: The lens was colorless and transparent, colored yellow by irradiation with light, and faded by irradiation with heat rays, showing good photochromic properties.

- Powder 1g of 6° silver bromide, add about 100 mts (7
) f get fl. Add 0.5 parts of silver bromide to 1:1 of isopropyl alcohol and dimenylformide. ai(i
=10 parts were added and mixed to form a slurry. Add this to a well-mixed solution of 50 parts of KP-80 (product of Shin-Etsu Chemical) A and 5 parts of B, and use a homogenizer to
It was heated at 100 rp+n for 60 minutes to form a paint.

A CR-59 lens that had been previously treated with a primer (a solution containing Primer PC (Shin-Etsu Chemical I product) AN and B at a ratio of 10=1) was immersed in this solution at a pulling rate of 35Cr/min. and then heated at 90℃ for 6 parts.
Heat cured for 7 days. The characteristics are shown in Table 1.

Example-4 Into a glass reactor, on one side, while stirring, 77
When 200 parts of Ran, 139.6 parts of ethanol, and a 0.1 N hydrochloric acid water bath of 0.44 M were added at room temperature, heat was generated and the liquid temperature reached 50°C. This solution was left at room temperature for one day and one time to ripen. Of this, take 66 Tokin, add 66 'r' of glacial acetic acid + 35 parts of IL-ethanol,
Further, 65 parts of 6-liquid ethanol containing 10% of a hydrolyzate of a tetrafluoroethylene vinyl acetate copolymer was mixed and dissolved.

On the other hand, 0.5 part of trimolybdate dimethylamine salt was mixed and suspended with 5 parts of ethanol, and then added to the above solution.
The mixture was stirred and dispersed using a homogenizer at 20 UU rpm for 60 minutes. Embrace it like this t*rg'IM
First, degrease and clean with alkaline water, apply to kOR-59 using the solo coat method, and heat at 80'C for 30 minutes at 160°C.
It was heated and cured for an hour. The thus obtained lens with a power of 4 was almost colorless, and turned dark brown when exposed to light using a tester. This material returned to its original colorless state after 2 minutes in a dark place, indicating good photochromic properties.

Incidentally, this process of color development and decolorization was performed at least 10 times or more. Table 1 shows this t1 characteristic.

Table 1゜ and above ``, Sequel IL!
13-・・t [1 Luha 2゛1f'Tofulastic Lens 1, hli if: t, j Ron 1 (2
56) Suwa O'a Kosha Co., Ltd., Representative Director Tsuneya Nakamura
, Akira (number of months (l supplement 1j (1 - 19! 1, l'JIN = 7 procedure correction '14 (voluntary) 1 specification 10 negative 2 ye - 5 ye [" 1 methanol 1 11 cichoroid" The statement has been corrected to 1-methanol part 11 (ko ["Ital/Rica"]).

2 Akii (Book 1, Line 10, I “Methanrun Rikagel”), [”08 (
jAL i + 52""K sleeve jEfru.

6 Akira, vIllnear 11o y211th line [Phenylcellonorbuta Yτ (~km combined,''), ``Phenylcellosolve part ke mixed,'' is the sleeve JE.

4 6th row from the bottom of Akira silk + ls white A certain gold that is ``almost colorless,'' ``It's almost colorless.''

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Claims (1)

[Claims] (1) A plastic lens whose surface layer is coated and cured with a composition containing an organic compound, a hydrolyzed product thereof, and a photochromic substance.