JPH0381381A - Method for bonding contact lens material to its support - Google Patents

Abstract

PURPOSE:To improve the working environment and efficiency by refraining from using any organic solvent, by bonding contact lens material to its support with a specified photocurable adhesive and curing the adhesive by ultraviolet radiation. CONSTITUTION:A photocurable adhesive is prepared by compounding (a) a photocurable monomer, oligomer or polymer which is a hydrophilic monomer preferably of formula I (wherein R<1> is H or CH3; n is 1-100; X is a group of formula II; R<2> is R<1>; y is OH, OR<3> or X; and R<3> is lower alkyl), having at least one radical-polymerizable group in its molecule, being liquid at room temperature, not impairing contact lens material, and yielding a water-soluble or swellable polymer, its oligomer or its polymer, respectively, with (b) 0.1-10wt.%, based on component (a), photoreaction initiator having absorptions in the ultraviolet region and, if necessary, (c) a photosensitizer. A contact lens material is bonded to its support with the above adhesive and the adhesive is cured by ultraviolet radiation to fasten the bonding.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method of adhering contact lens materials and their supports. More specifically, the present invention relates to a method of adhering a contact lens material and its support using ultraviolet light.

[Prior Art] Conventionally, in the production of contact lenses and intraocular lenses, when processing the lens material such as cutting, polishing, and other necessary treatments, the lens material is bonded and fixed to a suitable support with an adhesive. However, the support is fixed to those processing machines and processed. The adhesive needs to be able to be easily removed from the lens material after processing and without damaging the lens material.

As an example of such an adhesive, molten wax is conventionally known and used, but in the method of using molten wax, when the molten wax comes into contact with the contact lens material, the temperature of the wax decreases and the temperature of the wax decreases rapidly. Since the viscosity increases, it is difficult to adhere the adhesive layer to a constant thickness even if pressure is applied immediately between the contact lens material and its support. For this reason, even if this is cut and polished, the thickness of the completed contact lens tends to vary greatly.

As an adhesive method to solve this problem, JP-A-1-101319
The specification of this issue proposes an adhesive technology using a purple nine ray curable adhesive.

[Problems to be Solved by the Invention] In the method using ultraviolet rays proposed above, although the ultraviolet rays do not damage the lens material, since an organic solvent is used for desorption, there are problems such as odor and adhesion to the skin. This causes a deterioration of the environment for workers engaged in the manufacturing process. Another disadvantage is that the organic solvent swells the contact lens material, which is an organic material, and as a result, the lens is easily cracked or deformed. Therefore, it is necessary to take measures to prevent the odor and droplets of the organic solvent from affecting workers, such as installing a dedicated room, shielding the equipment, and wearing safety glasses, which impairs work efficiency.

SUMMARY OF THE INVENTION It is therefore an object of the present invention to provide a bonding method that does not have the above-mentioned problems.

[Means for Solving the Problem] In order to achieve the above object, the inventor has made extensive studies,
By using a photocurable monomer, a photocurable oligomer, or a photocurable polymer that produces a water-soluble polymer or a polymer that swells with water, a system that can be removed by water or a water-based solvent has been discovered, and the present invention has been achieved. .

That is, the present invention uses an adhesive consisting of at least a photocurable monomer, a photocurable oligomer or a photocurable polymer that produces a water-soluble polymer or a polymer that swells with water, and a photoinitiator to form a contact lens material and its support. This is a method of adhering a contact lens material and its support, which is characterized in that the contact lens material and its support are fixed by adhering the body in advance and then curing the adhesive with ultraviolet rays.

Contact lens material as referred to herein is a solid mass of polymeric material used to form a contact lens, commonly referred to as a button. Further, the support is, for example, when the contact lens material is a material whose one end is cut into a narrow shape, and is a member made of metal, polymer, etc. with a convex surface that is adhered to correspond to the concave shape. It is used by being fixed to a processing machine such as a lathe.

The photocurable monomer used in the present invention, the photocurable oligomer or the photocurable polymer, has at least one radically polymerizable group in one molecule and is liquid at room temperature, and is suitable for contact lens materials. It is a hydrophilic monomer, oligomer, or polymer that does not attack the material and also makes the polymer water-soluble or water-swellable.

Among such hydrophilic monomers, oligomers or polymers, in particular formula (I):
is an integer from 100 to 100, and X is the formula: CH2=C-
A group represented by C-1 R''0 (wherein R2 is a hydrogen atom or a methyl group), and Y is -OH or 10R3 or X (wherein R3 is a lower alkyl group). Compounds represented by are preferred.

Examples of the photocurable monomers mentioned above include vinyl monomers such as N-vinylpyrrolidone, 2-hydroxyethyl (meth)acrylate, tripropylene glycol di(meth)acrylate, tetraethylene glycol mono(meth)acrylate, and tetraethylene. Glycol di(meth)acrylate, octaethylene glycol mono(meth)acrylate, octaethylene glycol di(meth)acrylate, nanoethylene glycol mono(meth)
Acrylate, nano ethylene glycol di(meth)acrylate, nanopropylene glycol mono(meth)acrylate, nanopropylene glycol di(meth)acrylate, tetradecaethylene glycol mono(meth)acrylate, tetradecaethylene glycol mono(meth)acrylate
acrylate, trimethylolpropane tri(meth)acrylate, glycerol mono(meth)acrylate,
Glycerol di(meth)acrylate, polyethylene glycol (meth)acrylate, polypropylene glycol (meth)acrylate, methoxytetraethylene glycol (meth)acrylate, methoxy nanoethylene glycol (meth)acrylate, methoxypolyethylene glycol (meth)acrylate, (meth)acrylate Examples include (meth)acrylate monomers such as acrylic acid.

Examples of photocurable oligomers include polyether (meth)acrylate.

Further, as the photocurable polymer, a photocurable polymer having a group capable of radical polymerization, such as a highly polymerized polyethylene glycol poly(meth)acrylate having an acryloyl group, can be used.

These photocurable monomers, photocurable oligomers, or photocurable polymers may be used alone or in combination of two or more types.

The photoinitiator is preferably one that has absorption in the ultraviolet region, such as 4-phenoxydichloroacetophenone, 4-t-butyldichloroacetophenone, 1-(4-
Acetophenone-based products such as (isopropylphenyl) 2-hydroxy-2-methylpropan-1-one, benzoin-based products such as benzoin, benzoin methyl ether, and benzoin isopropyl ether, and benzophenone-based products such as benzophenone, benzoylbenzoic acid, and hydroxybenzophenone. , thioxanthone, 2-
Thioxanthone such as methylthioxanthone, 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 2,4-cyclothioxanthone, others, camphorquinone, benzyl, 3-ketocoumarin, anthraquinone, 2 -ethyl anthraquinone, α-naphthyl, acenaphthene, 1).

p'-dimethoxybenzyl, p, p'-dichlorobenzyl, 2,4.6-trimethylbenzoyl phenyl phosphine oxide, 2,6-dimethylbenzoyl diphenyl phosphine oxide, benzoyl jetoxyphosphine oxide, eosin Y and photoinitiators known by trade names such as Cantacure PDO and CM3 (manufactured by NOF Corporation), and these 1f! Or use a combination of two or more.

These photoinitiators can be used on a weight basis based on the photocurable monomer, photocurable oligomer or photocurable polymer.
It is used in a proportion of 1 to 10%, more preferably in a proportion of 0.2 to 5%.

In the present invention, a photosensitizer can be used in addition to the photoinitiator, if necessary. This photosensitizer exhibits an excellent curing effect when used together with a photoinitiator. Examples of photosensitizers include aliphatic amines such as triethanolamine, methylgetanolamine, triisopropanolamine, n-butylamine, N-methylgetanolamine, diethylaminoethyl methacrylate, Michler's ketone, 4,4 '-diethylaminophenone, ethyl 4-dimethylaminobenzoate,
(11-butoxy)ethyl 4-dimethylaminobenzoate,
Examples include aromatic amines such as isoamyl 4-dimethylaminobenzoate and 2-ethylhexyl 4-dimethylaminobenzoate, tri-n-butylphosphine, allylthiourea, etc., and these can be used alone or in combination of two or more. use.

In the present invention, the contact lens material and its support are bonded in advance using the above-mentioned adhesive, and then the adhesive is cured with ultraviolet light, and such light beams have a wavelength of 200 to 400 nrn. There is no particular limitation as long as it is within the range, and for example, a low-pressure mercury lamp, a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, an ultraviolet ray lamp, a xenon lamp, etc. can be used.

In addition to these, solvents, thermal polymerization inhibitors,
There is no problem in adding fillers, stabilizers, etc. to the extent that they do not interfere with the quality of the contact lens material.

To manufacture contact lenses using the method of the present invention, first, one side of the contact lens material is processed into a concave (or convex) spherical shape by cutting, polishing, etc., and a convex surface corresponding to the internuclear (or convex) spherical A support body having a (or concave) spherical surface at the end is adhered in advance using the above-mentioned adhesive which is liquid at room temperature, and then the adhesive is cured by irradiation with ultraviolet rays to form a contact lens material. Fix it to the support. Next, the adhered contact lens material and the support side of the support are fixed to the spindle of a processing machine such as a cutting machine or a polishing machine, and processed by cutting, polishing, etc., and further, by an appropriate method such as dipping in an aqueous solvent. Contact lenses can be manufactured by removing the lenses from the support.

The aqueous solvent used in the present invention must be able to be detached from the contact lens support and not attack the contact lens material, and must be compatible with the contact lens material and adhesive. They are appropriately selected and used depending on the type. For example, just water is fine. Furthermore, water containing a surfactant, salts, and a water-soluble organic solvent may be used, if necessary.

Since the photocured product of the present invention has the property of being water-soluble or swelling with water, by immersing it in the above water-based solvent, the photocured product dissolves or swells in water, and the contact lens and its support can be easily detached. It is possible to do so.

A specific method for desorption can be carried out, for example, by immersion in an aqueous solvent, and if necessary, by using ultrasound in combination.

The most important feature of the present invention is that the contact lens material and its support can be removed using an aqueous solvent. The advantages of this include, for example, being inexpensive, odorless, harmless to the human body, and easy to dispose of.

[Example] Next, the present invention will be specifically explained with reference to Examples, but the present invention is not limited to these in any way.

Example 1 Octaethylene glycol monomethacrylate) 10.0
g of benzoin isobutyl ether as a photoinitiator.
2 g was added and dissolved to prepare a photocurable adhesive.

Next, the bottom surface of a cylindrical methyl methacrylate polymer having a diameter of 15 mm was cut into a concave shape and polished to obtain a contact lens material. The curvature of this concave surface was measured using a digital contact gauge manufactured by Knights, and was found to be 7.80.
It was mm. This was adhered in advance to a convex brass support having the same radius of curvature as the above using the above photocurable adhesive.

Then, when the methyl methacrylate polymer was irradiated with 20W ultraviolet light for 8 hours from the side, the polymer and support were
was firmly attached.

This was fixed to the spindle of a spherical lathe, and the polymer was cut by a conventional method to form a convex surface into a lens shape.

Next, when this was left immersed in water, the lens could be easily peeled off after 30 minutes. After cleaning this lens, the curvature of the concave surface was measured and found to be 7.80 mm, which was the same as before bonding. Furthermore, no problematic scratches or clouding were observed on the lens surface.

Example 2 io of tetradecaethylene glycol diacrylate,
0.2 g of benzyl as a photoinitiator and 0.2 g of 2-ethylhexyl 4-dimethylaminobenzoate as a photosensitizer were added and dissolved in Og to prepare a photocurable adhesive.

Cylindrical methyl methacrylate (PMMA) with a diameter of 15 mm.
) The bottom surface of the polymer was cut into a concave shape and polished to obtain a contact lens material. The curvature of this concave surface is 8.05 mm
Met. This was adhered to a convex PMMA support having the same radius of curvature as the above using the photocurable adhesive.

Next, when the support was irradiated with a xenon lamp for 30 seconds from the side, the polymer and the support were firmly adhered.

This was fixed to the spindle of a spherical lathe and cut using a conventional method to form a convex surface into a lens shape. Next, when this lens was left immersed in water containing 0.5% nonionic surfactant, the lens could be easily peeled off after 30 minutes.

The concave curvature of the obtained contact lens was 8°05mm.
It was the same as before adhesion.

Example 3 Methoxytetraethylene glycol methacrylate 1
0.0g, benzophenondyl 0.2 as a photoinitiator
g, and 4-dimethylaminobenzoic acid 2 as a photosensitizer.
-0.2 g of ethylhexyl was added and dissolved to prepare a photocurable adhesive.

Cylindrical methyl methacrylate (PMMA) with a diameter of 15 mm.
) The bottom surface of the polymer was cut into a concave shape and polished to obtain a contact lens material. The curvature of this concave surface is 7.45 mm
Met. This was adhered to a convex PMMA support having the same radius of curvature as the above using the photocurable adhesive.

Next, when the support was irradiated with a xenon lamp for 30 seconds from the side, the polymer and the support were firmly adhered.

This was fixed to the spindle of a spherical lathe and cut using a conventional method to form a convex surface into a lens shape. Next, when this lens was left immersed in water containing 0.5% nonionic surfactant, the lens could be easily peeled off after 30 minutes.

The concave curvature of the obtained contact lens was 7°45mm.
It was the same as before adhesion.

Example 4 io of methoxy nanoethylene glycol methacrylate
, Og, 0.2 g of benzyl as a photoinitiator and 0.2 g of 2-ethylhexyl 4-dimethylaminobenzoate as a photosensitizer were added and dissolved to prepare a photocurable adhesive.

Cylindrical methyl methacrylate (PMMA) with a diameter of 15 mm.
) The bottom surface of the polymer was cut into a concave shape and polished to obtain a contact lens material. The curvature of this concave surface is 7.85 mm
Met. This was adhered to a convex PMMA support having the same radius of curvature as the above using the photocurable adhesive.

Next, when the support was irradiated with a high-pressure mercury lamp for 50 seconds from the side, the polymer and the support were firmly adhered.

This was fixed to the spindle of a spherical lathe and cut using a conventional method to form a convex surface into a lens shape. Next, when this lens was left immersed in water containing 0.5% nonionic surfactant, the lens could be easily peeled off after 30 minutes.

The concave curvature of the obtained contact lens was 7°85mm.
It was the same as before adhesion.

[Effects of the Invention] The present invention can provide a method for easily adhering and detaching a contact lens material and its support.

In addition, in the method of the present invention, water that is harmless to the body is used to detach the contact lens from its support, which not only improves work efficiency but also improves the working environment in the contact lens manufacturing process. is very useful.

Claims (1)

[Claims] A photocurable monomer that produces a water-soluble polymer that can be removed by an aqueous solvent or a polymer that swells with water;
A contact lens material and its support are brought into close contact with each other in advance using an adhesive consisting of a photocurable oligomer or a photocurable polymer and a photoinitiator, and then the adhesive is cured with ultraviolet rays to form a contact lens material. A method of adhering a contact lens material and its support, the method comprising adhering the support together.