JP2000314088A - Production of colored plastic lens for optical purpose and colored plastic-made optical lens - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a production process for colored plastic lens for optical purpose by efficiently dyeing plastic lenses for optical purpose in an arbitrary color tone and concentration with economical advantage and provide colored plastic lenses for optical purpose that are produced by this production process. SOLUTION: A cured coating layer of water-soluble polymer is formed on the surface of a plastic lens for optical purpose, then the resultant coated lens is dyed with an aqueous dyeing bath including a dispersion dye. In this case, the concentration of the dye in the dyed lens is adjusted by the amount of the dye retained in the cured coating layer or by this amount of the retained dye and the heating condition. This invention also provides a colored plastic lens for optical purpose prepared by this production process.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an improved method for producing a colored optical plastic lens and to a colored optical plastic lens obtained by the method. More specifically, the present invention provides a method for producing a colored optical plastic lens economically and advantageously by dyeing an optical plastic lens efficiently to a desired color tone and density, and a contact lens obtained by this method. The present invention relates to a plastic lens for coloring optics suitable as a spectacle lens, a camera lens, a projector lens, a telescope lens, a magnifying lens, and the like.

[0002]

2. Description of the Related Art In recent years, plastic lenses for optical use have been used in various fields instead of glass lenses. Among them, contact lenses and eyeglass lenses used for correcting vision have a cosmetic effect or a medical effect (for example, from ultraviolet rays). For the purpose of protecting the lens, etc.), the use of colored lenses has been actively performed. The reason why the glass lens is replaced by the plastic lens is that the plastic lens can be easily dyed in addition to its light weight and safety (hard to break).

Various methods have been used for dyeing plastic lenses for optical use. For example, as a method of dyeing a plastic lens for optics, particularly a plastic lens for spectacles, (1) a method of immersing the lens in a heated dye bath and then heating the lens to fix the dye, and (2) a plastic A method of preliminarily dissolving a dye in a raw material monomer of a lens substrate and then polymerizing the dye,
A method in which a dyed film is transferred by attaching a colored film to a spectacle lens, and (4) a method in which an organic dye is heated and sublimated in a gas phase to be colored (Japanese Patent Publication No. 35-13 / 1973)
No. 84) is known.

The above method (1) is a conventional method for coloring spectacle lenses, in which a disperse dye having a coloring ability for an optical plastic lens is dissolved and / or dissolved in water.
Or after heating the suspended dye solution, and immersing the optical plastic lens to be dyed therein for a predetermined time,
This is a method in which the optical plastic lens is heated to stabilize the dye that has penetrated therein by further diffusing into the inside. However, recently, in response to market needs for high added value, the diversification of optical plastic lens materials has progressed, and as a result, materials that are difficult to dye by conventional methods have increased. Therefore, methods such as raising the temperature of the dyeing solution as much as possible, adding a dyeing accelerator, a so-called carrier, to the dyeing solution, or extending the time of immersion in the dyeing solution are performed.

However, even with these methods,
There is a limit in the attained concentration, and there is a problem that it is not possible to dye at a high concentration even if it takes a long time to reach the target concentration.

A method of dyeing a coating film applied on a plastic lens material instead of directly dyeing the material (Japanese Patent Laid-Open No. 60-235101) has also been used. The method of coloring the optical plastic lens is a method of applying an organic hard coat solution in which a dye is dissolved on the surface of the optical plastic lens and then performing a curing treatment. The application method includes a dipping method, a spray method, and a spinning ( (Spin coating) method or the like is used. However, also in this method, since it is difficult to contain a large amount of dye in the thin film, the attained concentration is still limited, and dyeing at a high concentration cannot be performed.

Instead of applying an organic hard coat solution in which a dye is dissolved to the surface of an optical plastic lens, an organic hard coat solution that can be dyed is applied, and then a method similar to the above-described method for dyeing a plastic lens substrate is applied. A method of dyeing may be performed. However, also in this case, since it is difficult to contain a large amount of dye in the thin film, the attained concentration is still limited, and dyeing at a high concentration cannot be performed.

The method (2) is a method in which a dye is dissolved in a raw material monomer solution of an optical plastic lens substrate and then polymerized. However, the coloring density of the formed lens depends on the thickness of the lens. For example, in a concave lens in which the central part of the lens is thinner than the peripheral part, the color of the central part becomes lighter,
The periphery becomes darker, causing color shading throughout the lens, and in eyeglass lenses with different powers on the left and right,
Because there is a problem that the color density differs between the left and right,
This method is not practical. Furthermore, it is actually impossible to prepare many kinds of colored optical plastic lens base materials by preparing a large number of raw material liquids having different colors and densities according to market needs.

On the other hand, the method (3) for transferring a dye is effective if it is a flat plate, but it is difficult to cleanly attach a film to a curved optical plastic lens. In practice, it is actually impossible to perform uniform dyeing. Furthermore, in the method of (4), in which the dye is sublimated in the gas phase to be colored, the degree of sublimation of the dye is different for blue, red, and yellow, so that it is difficult to obtain a stable color development. It is not a tactical method.

[0010]

SUMMARY OF THE INVENTION Under such circumstances, the present invention efficiently dyes an optical plastic lens to a desired color tone and density to produce a colored optical plastic lens economically and advantageously. It is an object of the present invention to provide an industrial method.

[0011]

DISCLOSURE OF THE INVENTION The present inventors have developed an industrial method for efficiently dyeing an optical plastic lens to a desired color tone and density and economically and advantageously producing a colored optical plastic lens. As a result of intensive research,
Focusing on the fact that the disperse dye penetrates the inside of the plastic lens and dyes the lens when dyeing the lens, it depends on the amount of dye on the lens surface and the heat treatment conditions. Omitting the step of immersing the lens inside, instead, a cured film of a water-soluble polymer is formed in advance on the surface of the optical plastic lens, and an aqueous dyeing solution containing a disperse dye as a coloring component is brought into contact with the lens at room temperature. Once the disperse dye is once held in the cured film, heat treatment is performed to diffuse the inside of the lens. Preferably, the cured film and the dye present on the lens surface are further washed and removed with water, The objective can be achieved by controlling the amount of the dye held in the cured film or the amount of the dye and the heat treatment conditions when diffusing the dye into the inside of the lens. Heading the door, and have completed the present invention based on this finding.

That is, the present invention provides (1) forming a cured film of a water-soluble polymer on the surface of an optical plastic lens, and then contacting the lens with an aqueous dyeing solution containing a disperse dye as a coloring component; A method of dyeing a lens by temporarily holding a dye in the cured film, and then performing a heat treatment to diffuse the inside of the lens,
By the amount of the disperse dye once held in the cured film,
(2) a method for producing a colored optical plastic lens, which comprises adjusting the lens staining density; and (2) adjusting the lens staining density by adjusting the amount of the disperse dye once held in the cured film and the heat treatment conditions. (3) An optical plastic lens having a cured film of a water-soluble polymer formed on a surface thereof is immersed in a water-based dyeing solution containing a disperse dye as a coloring component, and then heat-treated. ,
Method (2), (4) A water-based dyeing solution containing a disperse dye as a coloring component is applied to the surface of an optical plastic lens having a cured film of a water-soluble polymer formed on the surface, and then heated. The methods of (1) and (2) above,
(5) After the heat treatment, the water-soluble polymer and disperse dye remaining on the surface of the optical plastic lens are washed away with water, and the methods (1) to (4) described above and (6) the methods obtained by these production methods. And a plastic lens for colored optics.

[0013]

BEST MODE FOR CARRYING OUT THE INVENTION In the method for producing a colored optical plastic lens of the present invention, first, a cured film of a water-soluble polymer is formed on the surface of the optical plastic lens to be dyed. The water-soluble polymer is excellent in solubility in an aqueous medium, high in safety, inexpensive, and may be any one that does not react with or hardly react with a disperse dye, and is not particularly limited. Can be appropriately selected from various compounds. Examples of such a water-soluble polymer include polyvinyl alcohol, polyacrylic acid, metal salts of polyacrylic acid, polyacrylamide, polyvinylpyrrolidone, polyethylene glycol, and the like. Polyethylene glycol and the like are preferred. These water-soluble polymers may be used alone or in combination of two or more.

The method for forming the cured film of the water-soluble polymer on the surface of the plastic lens for optics is not particularly limited. For example, the water-soluble polymer is dissolved in an aqueous medium to prepare an aqueous solution of the water-soluble polymer. It is advantageous to form a cured film of a water-soluble polymer by preparing and applying a coating treatment to the surface of an optical plastic lens using this, followed by heating. The aqueous solution of the water-soluble polymer is prepared by adding and dissolving the water-soluble polymer in an amount of preferably 2 to 20 parts by weight, more preferably 5 to 10 parts by weight, based on 100 parts by weight of the aqueous medium. The viscosity of the aqueous solution of the water-soluble polymer is preferably in the range of 5 × 10 ^{−3 to} 500 × 10 ⁻³ Pa · s (pascal · second) at room temperature, and particularly preferably in the range of 10 × 10 ^{−3 to} 100 × 10 ^−3.
A range of × 10 ⁻³ Pa · s is preferable. If the viscosity is too low, the aqueous solution of the water-soluble polymer coated on the surface of the optical plastic lens easily flows, and it is difficult to form a cured film of the water-soluble polymer having a required thickness. It becomes difficult to coat the lens surface with a uniform thickness. As the aqueous medium, water is used, but if necessary, water to which an organic solvent miscible with water is appropriately added can be used as long as the object of the present invention is not impaired.

As a method of coating an aqueous solution of a water-soluble polymer on the surface of an optical plastic lens,
Any method may be used as long as it can uniformly coat the surface of the optical plastic lens without unevenness, and there is no particular limitation, and a conventionally known method, for example, a method of directly coating the lens surface by a method such as brush coating or spin coating, or a dipping method , A spray method or the like can be used. Any of these methods can be suitably used, taking care to coat the lens surface with the aqueous solution of the water-soluble polymer as uniformly as possible.

After coating the surface of the plastic lens for optical use with the aqueous solution of the water-soluble polymer in this way, the lens is subjected to a temperature of usually 100 to 200 ° C., preferably 120 to 150 ° C. for 10 minutes. By heating and drying for about 6 to 6 hours, preferably about 30 minutes to 3 hours, a cured film of a water-soluble polymer is formed.

As described above, by forming a cured film of a water-soluble polymer on the surface of an optical plastic lens, when a water-based dyeing solution is brought into contact and adhered in the next step, the dyeing solution is absorbed by the water-soluble polymer. As a result, the disperse dye is uniformly held in the cured film, and the effect of preventing the attached dyeing liquid from flowing down from the surface of the optical plastic lens, agglomerating, or unevenly distributing is exhibited. Further, as described later, the plastic lens for optics to which the staining solution has adhered is subjected to a heat treatment to disperse and disperse the disperse dye held in the water-soluble polymer film into the inside of the plastic lens. When the water-soluble polymer is washed away with water, the disperse dye remaining on the surface also flows, and the disperse dye can be easily removed. In addition, since the water-soluble polymer has poor affinity for the disperse dye, it also plays a role in facilitating the penetration and diffusion of the disperse dye into the plastic lens during heat treatment.

In the method of the present invention, an optical plastic lens having a cured film of a water-soluble polymer formed on its surface as described above is dyed with an aqueous dye solution containing a disperse dye as a coloring component. The above disperse dye is generally a poorly soluble dye in water, and is widely used as a suspension dissolved and / or dispersed in water for dyeing optical plastic lenses. Sometimes called a sublimation dye or a sublimation dye. As particularly preferred dyes, Dianix Blue (Dianix Blue) AC-E and Dynix Red (Dianix Red) AC-E manufactured by Dystar Japan Co., Ltd., Nippon Kayaku
Kayalon Polyester Colors Yellow 4G
-E and Kayalon Polyester Colors Scarlet 2R-E.

In the present invention, these disperse dyes are
An aqueous staining solution is prepared by dissolving and / or suspending in an aqueous medium. The concentration of the disperse dye in the aqueous dyeing solution is preferably as high as possible in order to increase the dyeing concentration of the optical plastic lens. In addition, when used as an ink for an ink jet printer, to avoid clogging of the ink jet printer nozzle, the particle diameter of the disperse dye that is completely dissolved or suspended without being completely dissolved is equal to or smaller than the diameter of the ink jet printer nozzle. In other words, it is preferable that the treatment be performed by a method such as filtration or centrifugation so that the particle size is tens of microns or less, preferably 20 microns or less. The concentration of the disperse dye in the aqueous dyeing solution is selected in the range of usually 0.1 to 20% by weight, preferably 3 to 10% by weight.

As the aqueous medium, water is used, and if necessary, as long as the object of the present invention is not impaired.
Water to which an organic solvent having miscibility with water, a pH adjuster, a surfactant, an antifoaming agent, a preservative and the like are appropriately added can also be used.

The method of bringing the aqueous dye solution into contact with the surface of the optical plastic is not particularly limited as long as the dye solution can be uniformly and uniformly contacted with the surface of the optical plastic lens. A method of directly applying to the lens surface by a known method, for example, a method such as brush coating, spin coating, or application by an ink jet printer, or a dipping method, a spray method, or the like can be used. Among these methods, a method of directly applying to the lens surface and a dipping method are preferable. In particular, an application method using an ink-jet printer is applicable to (1) effective use of ink, (2) a database and an application stored in a computer. It is suitable because it can be applied to a desired color tone and density, and (3) it can be applied in a short time.

In the case where ink is applied to the surface of the optical plastic lens by an ink jet printer, the surface of the optical plastic lens and the discharge direction of the ink jet printer nozzle are adjusted so that the ink droplets strike the surface of the optical plastic lens at right angles. Is preferably adjusted so that data controlled by the computer is faithfully reproduced on the surface of the optical plastic lens. To make such an adjustment, refer to Japanese Patent Application No. 10-0242.
For example, the optical lens coloring system described in the specification of JP-A No. 01 can be used. In addition, by these methods,
When the dyeing solution is brought into contact with the surface of the plastic lens for optics, it is preferably carried out at room temperature.

In the present invention, the aqueous dyeing solution containing the disperse dye as a coloring component is brought into contact with the cured film in this manner, and the disperse dye is once held in the cured film, and then subjected to a heat treatment to form the inside of the lens. The dyeing density is adjusted by adjusting the amount of the disperse dye retained in the cured film, or the amount of the retained disperse dye and the heat treatment conditions.

The amount of disperse dye retained in the cured coating is
It can be controlled by the thickness of the cured film and / or the amount of the disperse dye to be brought into contact with the surface of the cured film. The amount of the disperse dye to be brought into contact with the surface of the cured film can be adjusted by adjusting the amount of the aqueous dye discharged from the nozzle of the ink jet printer when applying using the ink jet printer, or by applying the aqueous dye to the ink jet printer. It is preferable to control by adjusting.

On the other hand, the adjustment of the lens staining density according to the heat treatment conditions can be performed by controlling the heat treatment temperature and / or the heat treatment time. To actually adjust the lens dyeing concentration, a coloring database for each dye and lens relating to the thickness of the cured film, the amount of the disperse dye to be brought into contact, the heat treatment temperature and the heat treatment time is created in advance, and this database is prepared. Is used to determine individual coloring data (thickness of the cured film, amount of disperse dye to be contacted, heat treatment temperature, heat treatment time) relating to a desired dye concentration and color tone, and dyeing is performed based on this data. desirable.

In the present invention, the disperse dye held in the cured film is subjected to heat treatment by contacting the surface of the cured film with a dyeing solution by the direct coating method or the dipping method as described above. Spread inside. The heating temperature at this time is usually 80 to 200 ° C., preferably 85
１５０150 ° C. The heating time is selected in the range of usually 10 minutes to 24 hours, preferably 30 minutes to 3 hours. In general, when the heating temperature is high and the heating time is long, the dyeing density becomes high, so that the surface shape of the optical plastic lens is deformed or yellowed. It is desirable to select the optimal values of the heating temperature and the heating time for each lens material and desired dyeing concentration in consideration of the balance of the above. The heating furnace used for this heat treatment is not particularly limited as long as it can uniformly heat the plastic lens for optical use, and is not particularly limited. For example, an electric furnace, a hot-air circulation furnace, an infrared oven, a microwave oven, or the like is used. be able to.

After the heating is completed, a water-soluble polymer (cured film) and a disperse dye that has not been completely diffused remain on the surface of the optical plastic lens. It is desirable to perform a wiping process. In that case, if the water-soluble polymer in which the disperse dye remains is removed, the lens surface becomes almost clean.Therefore, in order to efficiently clean a large number of optical plastic lenses in a short time, a water washing treatment, especially in water, is required. It is preferable to perform ultrasonic cleaning or the like.

Examples of the optical plastic lens to which the staining method of the present invention is applied include optical lenses used for contact lenses, spectacle lenses, camera lenses, projector lenses, telescope lenses, magnifying lenses, and the like. In particular, vision correction lenses such as contact lenses and spectacle lenses are suitable. Specifically, polydiethylene glycol bisallyl carbonate, methyl methacrylate homopolymer, copolymer of methyl methacrylate and one or more other monomers, polycarbonate, polystyrene, polyethylene terephthalate, polyurethane, polythiourethane, and other sulfur-containing compounds A plastic lens made of a polymer or the like can be given.

The present invention also provides a colored optical plastic lens obtained by the above method. The plastic lens for coloring optics is suitably used, for example, as a contact lens, an eyeglass lens, a camera lens, a projector lens, a telescope lens, a magnifying lens, and the like.

[0030]

Next, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples.

Example 1 (1) Preparation of Staining Solution Dianix Blue AC-E5 manufactured by Dystar Japan Co., Ltd. was added to 100 parts by weight of distilled water.
A part by weight was added and stirred at room temperature to prepare a dyeing solution in which a part of the disperse dye was suspended.

(2) Coating of water-soluble polymer 100 parts by weight of distilled water was added to polyvinyl alcohol # 500
[Kanto Chemical Co., Ltd., molecular weight about 500, hydrolysis degree 8
6.5-89 mol%] and stirred at room temperature for 24 hours to completely dissolve. After immersing a lens made of polydiethylene glycol bisallyl carbonate (degree: 0.00, thickness: 2.0 mm, outer diameter: 70 mm) at room temperature in the aqueous solution, place the lens on a donut-shaped jig that can be fixed around the lens. The sample was placed and heated in an oven at 120 ° C. for 30 minutes to form a polyvinyl alcohol # 500 film on the surface.

(3) Dyeing of plastic lens for optics The dyeing solution prepared in the above (1) is stirred with a magnetic stirrer, and the lens obtained in the above (2) is immersed at room temperature in the dyeing solution on both sides. Then, the lens was placed on a donut-shaped jig that can be fixed around the lens, and heated in an oven at 120 ° C. for 30 minutes. After cooling, the lens was taken out and the lens surface was washed with water to remove the dried water-soluble polymer and the remaining disperse dye. Wiping with a cloth to which acetone was applied did not cause discoloration, and the dyeing density at the central portion was 35% as measured by a spectrophotometer at a light transmittance of 400 nanometers. Moreover, the whole was uniformly dyed.

Example 2 In the dyeing of the optical plastic lens of (3) in Example 1, the heating time in an oven at 120 ° C. was 30 minutes.
The same operation as in Example 1 was performed except that the time was changed from 60 minutes to 60 minutes. The colored lens obtained in this way is
Wiping with a cloth to which acetone was applied did not cause color fading, and the dyeing density at the center was 50% as measured by a spectrophotometer at a light transmittance of 400 nanometers. Moreover, the whole was uniformly dyed.

Example 3 In the dyeing of the optical plastic lens of (3) in Example 1, the heating temperature in the oven was changed from 120 ° C. to 1
The same operation as in Example 1 was performed except that the temperature was changed to 35 ° C. Even if the colored lens thus obtained was wiped with a cloth to which acetone was applied, no color fading occurred, and the dyeing density of the central portion measured using a spectrophotometer at a light transmittance of 400 nm was found. 60%. Moreover, the whole was uniformly dyed.

Example 4 In the dyeing of the optical plastic lens of (3) in Example 1, the heating temperature in the oven was changed from 120 ° C. to 1
The same operation as in Example 1 was performed except that the temperature was changed to 05 ° C. Even if the colored lens thus obtained was wiped with a cloth to which acetone was applied, no color fading occurred, and the dyeing density of the central portion measured using a spectrophotometer at a light transmittance of 400 nm was found. 7%. Moreover, the whole was uniformly dyed.

Example 5 (1) Preparation of Dyeing Solution In 100 parts by weight of distilled water, Dianix Red (Dianix Red) AC-E10 manufactured by Dystar Japan Ltd. was used.
A part by weight was added and stirred at room temperature to prepare a dyeing solution in which a part of the disperse dye was suspended.

(2) Coating of water-soluble polymer 100 parts by weight of distilled water was added to polyvinyl alcohol # 200
0 [manufactured by Kanto Chemical Co., Ltd., molecular weight: about 2,000, degree of hydrolysis: 78 to 82 mol%] was added, and the mixture was stirred at room temperature for 24 hours to completely dissolve. A base lens (degree: -3.00 diopters, center thickness: 1.2 m) of a polythiourethane-based lens (trade name: IAS) of HOYA CORPORATION was added to the aqueous solution.
m, concave lens with an outer diameter of 75 mm) at room temperature
The lens was placed on a donut-shaped jig that could be fixed around the lens, and heated in an oven at 110 ° C. for 30 minutes to form a polyvinyl alcohol # 2000 coating on the surface.

(3) Dyeing of plastic lens for optics The dyeing solution prepared in the above (1) is applied to the concave surface of the lens obtained in the above (2) on the first stage at 800 rpm / 15 sec.
The second stage was spin-coated at 3000 rpm / 30 seconds. Place the lens with the staining solution attached to the concave surface on a donut-shaped jig that can be fixed around the lens.
For 30 minutes. After cooling, the lens was taken out and the lens surface was washed with water to remove the dried water-soluble polymer and the remaining disperse dye. Next, the convex surface was spin-coated in the same manner as the concave surface, and heat-treated under the same conditions as the concave surface. After cooling, the lens was taken out and the lens surface was washed with water to remove the dried water-soluble polymer and the remaining disperse dye. Even when wiped with a cloth to which acetone was applied, no discoloration occurred, and the dyeing concentration near the center was 28% as measured by a light transmittance of 700 nanometers using a spectrophotometer. Moreover, the whole was uniformly dyed.

Example 6 (1) Preparation of Ink for Inkjet Printer 60 parts by weight of distilled water, 7 parts by weight of glycerin, 18 parts by weight of ethylene glycol, 8 parts by weight of urea, 2 parts by weight of diethanolamine, surfactant [manufactured by Nikko Chemicals Co., Ltd. , Polyoxyethylene alkyl phenyl ether, trade name NP-
7.5) Disperse dye Kayalon polyester color manufactured by Nippon Kayaku Co., Ltd. in 0.2 parts by weight of aqueous solvent
Yellow (Kayalon Polyester Colors Yellow) 4
5 parts by weight of GE-E was added, and the mixture was stirred at room temperature for 24 hours to prepare a dyeing solution in which some disperse dyes were suspended. This suspension was subjected to suction filtration using Whatman filter paper No. 3 to remove a small amount of insoluble matter, thereby preparing an ink for an ink jet printer.

(2) Coating of Water-Soluble Polymer To 100 parts by weight of distilled water was added 5 parts by weight of N-vinylpyrrolidone polymer [manufactured by Wako Pure Chemical Industries, Ltd., molecular weight: about 25,000], and the mixture was stirred at room temperature for 24 hours. Completely dissolved. At room temperature, the base lens of a sulfur-containing plastic lens (trade name: Teslalid) of HOYA CORPORATION
1.00 diopter, center thickness 2.5mm, outer diameter 75m
m), and the lens was placed on a donut-shaped jig that can be fixed around the lens and heated in an oven at 120 ° C. for 30 minutes to form a coating of N-vinylpyrrolidone polymer on the surface. .

(3) Dyeing of Plastic Lens for Optical Use Using the ink prepared in (1) above, a dyeing pattern was printed on one side of the lens obtained in (2) by an ink jet printer. Place the lens with the ink on a donut-shaped jig that can be fixed around
Heat in oven at 30 ° C. for 60 minutes. After cooling, it was taken out, ink was adhered to the opposite surface in the same manner, and heated under the same conditions. After cooling, both surfaces of the lens were washed with water to remove the dried water-soluble polymer and the remaining disperse dye. Even when wiped with a cloth to which acetone had been applied, no color fading occurred, and the dyeing density near the center was 30% as measured by a light transmittance of 550 nm using a spectrophotometer. Also,
The whole was uniformly dyed.

Example 7 (1) Preparation of ink for ink jet printer 60 parts by weight of distilled water, 7 parts by weight of glycerin, 18 parts by weight of ethylene glycol, 8 parts by weight of urea, 2 parts by weight of diethanolamine, a surfactant [manufactured by Nikko Chemicals Co., Ltd.] , Polyoxyethylene alkyl phenyl ether, trade name NP-
7.5) Into 0.2 parts by weight of an aqueous solvent, use Dianix B (Dianix B) manufactured by Dystar Japan Co., Ltd.
lue) 5 parts by weight of AC-E was added, and the mixture was stirred at room temperature for 24 hours to prepare a dyeing solution in which some disperse dyes were in a suspended state. This suspension was subjected to suction filtration using Whatman filter paper No. 3 to remove a small amount of insoluble matter, thereby preparing an ink for an ink jet printer.

(2) Coating of water-soluble polymer 100 parts by weight of distilled water was mixed with polyvinyl alcohol # 500
[Kanto Chemical Co., Ltd., molecular weight about 500, hydrolysis degree 8
6.5-89%], and stirred at room temperature for 24 hours to completely dissolve. After dipping a lens made of polydiethylene glycol bisallyl carbonate (degree: 0.00, thickness: 2.0 mm, outer diameter: 70 mm) in the aqueous solution at room temperature, a donut-shaped jig that can be fixed around the lens is provided.
The lens was placed and heated in an oven at 120 ° C. for 30 minutes to form a polyvinyl alcohol # 500 coating on the surface.

(3) Dyeing of plastic lens for optics Using the ink prepared in (1) above, a dyeing pattern was printed on one side of the lens obtained in (2) by an ink jet printer. The lens with the ink attached was placed on a donut-shaped jig that can be fixed around and heated in an oven at 120 ° C. for 30 minutes. After cooling, it was taken out, ink was adhered to the opposite surface in the same manner, and heated under the same conditions. After cooling, both surfaces of the lens were washed with water to remove the dried water-soluble polymer and the remaining disperse dye.
No color fading occurred even when wiped with a cloth to which acetone was applied, and the dyeing concentration at the center was 30% as measured by a light transmittance of 400 nanometers using a spectrophotometer. Moreover, the whole was uniformly dyed.

Example 8 In the dyeing of the optical plastic lens (3) in Example 7, instead of attaching the ink to the opposite surface,
The same operation as in Example 7 was performed except that the ink was attached to the same surface. The colored lens obtained in this way is
No discoloration occurred when the cloth was wiped with a cloth to which acetone was applied, and the dyeing concentration at the center was 28% as measured by a light transmittance of 400 nanometers using a spectrophotometer. Moreover, the whole was uniformly dyed.

Example 9 Example 7 was repeated except that the following changes were made in the dyeing of the optical plastic lens (3) in Example 7.
The same operation as described above was performed. That is, in the dyeing of the optical plastic lens of (3), a dyeing pattern was printed on one side of the lens obtained in (2) using an ink jet printer, using the ink prepared in (1). The lens with the ink attached was placed on a donut-shaped jig that can be fixed around and heated in an oven at 120 ° C. for 30 minutes. After cooling, it was taken out, ink was adhered to the opposite surface in the same manner, and heated under the same conditions. After cooling, the above method was repeated once again to print a dyed pattern on both sides. Both sides of the lens were washed with water to remove the dried water-soluble polymer and the remaining disperse dye.

The colored lens thus obtained did not lose color even if it was wiped with a cloth soaked with acetone, and was dyed at the central part measured with a spectrophotometer at a light transmittance of 400 nanometers. The concentration was 50%. Also,
The whole was uniformly dyed.

Comparative Example 1 (1) Preparation of Staining Solution Dianix Blue AC-E5 manufactured by Dystar Japan Co., Ltd. was added to 100 parts by weight of distilled water.
A part by weight was added and stirred at room temperature for 24 hours to prepare a dyeing solution in which a part of the disperse dye was suspended.

(2) Dyeing of plastic lens for optics The dyeing solution prepared in the above (1) was heated to 90 ° C., and a lens made of polydiethylene glycol bisallyl carbonate (frequency 0.00, thickness 2.0 mm, outer diameter) 70mm)
After immersion for an hour, the lens surface was cooled and the lens surface was washed with water.
In addition, discoloration occurred when the cloth was wiped with a cloth soaked with acetone. The dyeing density at the center was 10% as measured using a spectrophotometer at a light transmittance of 400 nanometers. While the dyeing solution heated to 90 ° C. was repeatedly used, the dye deteriorated after about 15 hours in total, and could not be dyed in the same color tone as the first time.

COMPARATIVE EXAMPLE 2 (1) Preparation of Dyeing Solution In 100 parts by weight of distilled water, Dianix Red (Dianix Red) AC-E10 manufactured by Dystar Japan Ltd. was used.
A part by weight was added and stirred at room temperature to prepare a dyeing solution in which a part of the disperse dye was suspended.

(2) Coating of Water-Soluble Polymer Polyvinyl alcohol # 200 was added to 100 parts by weight of distilled water.
0 [manufactured by Kanto Chemical Co., Ltd., molecular weight: about 2,000, degree of hydrolysis: 78 to 82 mol%] was added, and the mixture was stirred at room temperature for 24 hours to completely dissolve. A base lens (degree: -3.00 diopters, center thickness: 1.2 m) of a polythiourethane-based lens (trade name: IAS) of HOYA CORPORATION was added to the aqueous solution.
m, a concave lens having an outer diameter of 75 mm) was immersed at room temperature, pulled up, and allowed to stand at room temperature. Although a coating of an aqueous solution of polyvinyl alcohol # 2000 was formed on the lens surface, the coating was sticky because no heat treatment was performed.

(3) Dyeing of plastic lens for optics A lens having an adhesive film of an aqueous solution of polyvinyl alcohol # 2000 formed on the surface was immersed in the staining solution prepared in the above (1) at room temperature. alcohol#
Part of the adhesive film of the 2,000 aqueous solution was dissolved in the dyeing solution, and the adhered state of the disperse dye solution was not uniform. The lens was placed on a donut-shaped jig that can be fixed around the lens, and heated in an oven at 110 ° C. for 30 minutes. After cooling, the lens was taken out and the lens surface was washed with water to remove the dried water-soluble polymer and the remaining disperse dye. No color fading occurred even when wiped with a cloth to which acetone was applied, but the dyeing density near the center measured with a spectrophotometer at a light transmittance of 700 nanometers using a spectrophotometer in a stained state with unevenness throughout. It varied in the range of 15 to 20%.

Comparative Example 3 (1) Preparation of Dye Solution Disperse dye Kayalon Polyester Color Yellow (Kayalon Po) manufactured by Nippon Kayaku Co., Ltd. was added to 100 parts by weight of distilled water.
5 parts by weight of (Liester Colors Yellow) 4GE-E were added, and the mixture was stirred at room temperature to prepare a dyeing solution in which a part of a disperse dye was suspended.

(2) Surface Coating of Plastic Lens for Optical Use Base lens of sulfur-containing plastic lens (trade name: Teslalid) of HOYA CORPORATION (power: 1.00 diopter, center thickness: 2.5 mm, convex lens having an outer diameter of 75 mm) ) To a polyester oligomer (Adipic acid polyester manufactured by Asahi Denka Kogyo Co., Ltd., trade name: Adecaizer PN-1)
010], and the lens was placed on a donut-shaped jig that can be fixed around the lens, and heated in an oven at 120 ° C. for 30 minutes. When cooled to room temperature, a flexible polyester-based oligomer film was formed.

(3) Dyeing of Optical Plastic Lens The lens obtained in (2) was immersed in the dyeing solution prepared in (1) at room temperature. The stained solution flowed down or aggregated on the lens surface, and did not become uniform. The lens was placed on a donut-shaped jig that can be fixed around it and heated in an oven at 130 ° C. for 60 minutes. After cooling, the surface of the lens was washed with water, and the dried dye flowed out and entered the lens. Had no dye transfer.

[0057]

According to the present invention, an optical plastic lens, which is difficult to dye particularly with a disperse dye solution containing water as a dispersion medium, can be dyed efficiently and economically at an arbitrary color tone and density. The plastic lens for coloring optics dyed by the method of the present invention is suitably used as, for example, a contact lens, an eyeglass lens, a camera lens, a projector lens, a telescope lens, a magnifying lens, and the like.

Continuation of the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat II (reference) C09D 7/12 C09D 7/12 Z 201/00 201/00 D06P 3/00 D06P 3/00 E H 5/20 5 / 20 A G02B 1/10 G02C 7/02 G02C 7/02 G02B 1/10 Z // B29K 101: 00 F term (reference) 2K009 AA15 BB11 CC21 DD02 DD06 DD09 EE01 FF01 4F213 AA19 AA21 AA23 AB12 AD05 AD18 AH74 WA02 WA54 WA58 WA75 WA92 WB01 WB18 4H057 AA02 CA03 CB08 CC01 DA02 DA17 DA32 GA01 GA13 HA01 HA19 JA10 JB02 4J038 CE021 CG031 CG091 CG171 CK031 DF011 KA08 PA07 PC08

Claims (14)

[Claims] A cured film of a water-soluble polymer is formed on the surface of an optical plastic lens.
By contacting an aqueous dyeing solution containing a disperse dye as a coloring component, and once holding the disperse dye in the cured film, by heat treatment to diffuse into the lens,
What is claimed is: 1. A method for producing a colored optical plastic lens, comprising: adjusting the dyeing density of the lens by adjusting the amount of the disperse dye once held in the cured film. 2. The method according to claim 1, wherein the lens dyeing density is adjusted by the amount of the disperse dye once held in the cured film and the heat treatment conditions. 3. The amount of the disperse dye once held in the cured film is controlled by the thickness of the cured film and / or the amount of the disperse dye brought into contact with the surface of the cured film.
The method described in. 4. The method according to claim 2, wherein the adjustment of the lens staining density according to the heat treatment conditions is performed by controlling the heat treatment temperature and / or the heat treatment time. 5. The method according to claim 1, wherein the surface of the optical plastic lens is subjected to a coating treatment using an aqueous solution of a water-soluble polymer and then heated to form a cured film of the water-soluble polymer. The method described in. 6. An optical plastic lens having a cured film of a water-soluble polymer formed on a surface thereof is immersed in an aqueous dyeing solution containing a disperse dye as a coloring component, and then heat-treated. A method according to any one of the preceding claims. 7. An aqueous plastic solution containing a disperse dye as a coloring component is applied to the surface of an optical plastic lens having a cured film of a water-soluble polymer formed on the surface, followed by heat treatment. 6. The method according to any one of items 5 to 5. 8. The method according to claim 7, wherein the aqueous dyeing solution is applied to the surface of an optical plastic lens having a cured film of a water-soluble polymer formed on the surface thereof using an ink jet printer. 9. The method according to claim 8, wherein the amount of the aqueous dyeing liquid discharged from the ink jet printer nozzle is adjusted to control the amount of the disperse dye to be brought into contact with the surface of the cured film. 10. The method according to claim 8, wherein the number of application of the aqueous dyeing solution by the ink jet printer is adjusted to control the amount of the disperse dye to be brought into contact with the surface of the cured film. 11. The method according to claim 8, 9 or 10, wherein a heating temperature and / or a processing time is controlled when heating after applying the aqueous dyeing solution by an ink jet printer. 12. The method according to claim 1, wherein after the heat treatment, the water-soluble polymer and the disperse dye remaining on the surface of the optical plastic lens are washed away with water. 13. The method according to claim 1, wherein the water-soluble polymer is at least one selected from polyvinyl alcohol, polyacrylic acid, metal salts of polyacrylic acid, polyacrylamide, polyvinylpyrrolidone and polyethylene glycol. The method described in the section. 14. A plastic lens for colored optics, obtained by the method according to claim 1. Description: