JPH02255151A - Composition for forming intra-ocular lens - Google Patents

Abstract

PURPOSE:To facilitate the intra-ocular injection of the liquid compsn. contg. a photopolymerizable monomer and a photoinitiator and to cure the compsn. in a short period of time after the injection by polymerizing the compsn. in the eye. CONSTITUTION:The liquid compsn. which contains the photopolymerizable monomer and the photoinitiator and has a photosetting property is used as the injection material to be injected directly into the crystalline capsule after the crystalline lens is substantially removed in the state of allowing the crystalline lens to remain or to be injected into the balloon body inserted into the crystalline capsule. This compsn. is irradiated with prescribed light and is cured in a short period of time within the eye, by which the intra-ocular lens is formed. The direct injection of the photopolymerizable monomer into the crystalline capsule is possible as the bioadaptability is imparted in terms of toxicity and resilience, etc., in the case of adopting a silicone monomer for the photopolymerizable monomer. The injection material does not come into direct contact with the inside of the crystalline capsule in the case of using the compsn. by injecting the same into the balloon housed in the crystalline capsule and, therefore, the free selection of the photopolymerizable monomer is possible.

Description

Detailed Description of the Invention (Technical Field) The present invention involves removing the lens parenchyma while leaving the lens capsule, and then directly injecting it into the lens capsule or into a balloon body inserted into the lens capsule and hardening it. The present invention relates to an injection material for forming an intraocular lens, and particularly to a composition for forming an intraocular lens that can be cured in a short time by photopolymerization.

(Background technology) As an intraocular lens to replace the crystalline lens, a liquid material is inserted directly into the lens capsule after the lens parenchyma has been extracted, or a balloon body (thin film capsule) inserted into the lens capsule.
Some are formed by injecting the inside of the body. In addition, the liquid injection materials used include gel-like materials and materials that polymerize and solidify within the eye in order to prevent the injection materials from leaking from the lens capsule or balloon body through the injection port. etc. have been proposed.

For example, US Pat. No. 4,713,072 discloses that as a material to be injected into the balloon body of a balloon-type intraocular lens,
The use of a gel-like sodium hyaluronate aqueous solution has been disclosed. However, when using such a gel-like injection material, although leakage from the balloon body is reduced, its high viscosity makes it difficult to inject using a catheter, etc., reducing work efficiency. However, material leakage cannot be completely prevented. In addition, since the sodium hyaluronate aqueous solution has a low refractive index, there is also the problem that the thickness of the intraocular lens must be made thicker in order to obtain a refractive power similar to that of the crystalline lens.

In addition, Japanese Patent Application Laid-open No. 63-216574 discloses that so that the ratio of unsaturated aliphatic groups and hydrosilyl groups is about the same,
A composition containing two types of organopolysiloxanes having respective groups is disclosed. Injection materials with such compositions polymerize and harden over time, so
It can be easily injected in a liquid state and solidifies within the eye after injection, making it possible to prevent the intraocular lens material from leaking out. However, since this composition takes several hours to harden after being blended, the injection material leaks from the injection port after surgery and before the composition hardens, resulting in the formation of the desired intraocular shape. The problem is that lenses cannot be obtained.

As a countermeasure to this problem, in order to shorten the time from injection to curing, it is possible to prepare the mixture in advance and inject it once the polymerization has progressed to a certain extent, but it is difficult to inject due to the significant increase in viscosity. There is an inherent problem.

(Problem to be solved) The present invention has been made under these circumstances, and the problem to be solved is that when injected into the eye, it is in a liquid state and hardens within a short period of time after injection. An object of the present invention is to provide a composition for forming an intraocular lens.

(Solution Means) In order to solve this problem, in the present invention, an intraocular lens forming composition that is polymerized in the eye to give the desired intraocular lens is made of a photopolymerizable monomer. It was prepared to contain a photoinitiator.

In addition, when the composition for forming an intraocular lens according to the present invention is directly injected into the lens capsule in the eye, a silicone monomer is particularly advantageously selected as the photopolymerizable monomer; When the composition for forming an intraocular lens of the present invention is injected into a balloon body housed in a lens capsule, such monomers are not specified.

(Action/Effect) In other words, since the composition for forming intraocular lenses according to the present invention is liquid and has photocurability, it has a low viscosity and is easy to inject, and after injection, it is easy to inject with light. It can be cured within a few minutes by irradiation.

This prevents the injection material from leaking from the injection port, making it possible to form an intraocular lens with a desired shape.

Further, in the composition for forming an intraocular lens of the present invention, when the photopolymerizable monomer is a silicone monomer,
Since it can be made biocompatible in terms of toxicity and softness, it can be directly injected into the lens capsule. It is also possible to use the balloon housed in the body by injecting it into the body. In that case, the injection material does not come into direct contact with the lens capsule, so there is no need to consider the biocompatibility of the injection material, and there is no need to consider the biocompatibility of the injection material. Polymerizable monomers can be freely selected.

(Specific structure) By the way, the photopolymerizable monomer used in the composition of the present invention can be polymerized by irradiation with light under the action of a photoinitiator, which will be described later. Some are toxic to humans.

However, since the composition of the present invention can also be used as a material for injection into a balloon body housed in the lens capsule, there are no particular limitations on the monomer when using such a balloon body. do not have.

Specifically, the balloon body (JP-A-63-200755, U.S. Patent No. 45854-51, U.S. Patent No. t69)
As a photopolymerizable monomer that can be used only when injected into a hollow intraocular lens balloon (such as a hollow intraocular lens balloon body implanted in the lens capsule) as shown in No. 3717, No. 4713072, etc. The following monomers can be mentioned, and one or more monomers are appropriately selected and used from these monomers. Please note that below:
``(meth)acrylate'' refers to ``...acrylate'' or [...methacrylate].

2-ethylhexyl (meth)acrylate, 2hydroxyethyl (meth)acrylate, 2hydroxypropyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentenyloxyethyl (meth)acrylate , 1.3-butanediol di(meth)acrylate, 1.4-butanediol di(meth)acrylate, 1.6-hexanediol di(meth)acrylate,
Diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, neobentyl glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, hydroxypivalic acid ester neopentyl glycol di(meth)acrylate, tripropylene glycol Di(meth)acrylate, 1,3-bis(3°-(meth)acryloxyethoxy-2′-hydroxypropyl)-5,5 dimethylhydantoin, trimethylolpropane tri(meth)
acrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol hexa(meth)acrylate, 2,2-bis-(3-methacryl, 2-hydroxypropoxyphenyl)propane, and the like.

In addition, when injecting directly into the lens capsule without using a balloon body, the amount of polymer that can be used is limited due to safety reasons for the eye tissue, but silicone monomers have biocompatibility. It is preferable to have this.

The silicone monomer that can be used is an organopolysiloxane containing at least one polymerizable group in one molecule, for example, the polymerizable group shown below.

■-CH=CH2 ■-CH=CHCH3 ■ 0 0-(, -CH=CH.

■ OCH3 O-C-C=CH2 ■ -CHt CH=CH2 ■ (CH3).

→CH, product Si+○ (ORL ■ O CH3 C=C)I2)c In the polymerizable group shown by ■ above, R1 and RZ are the same or different unsubstituted or substituted monovalent hydrocarbon groups, and R3
is a hydrogen atom or a methyl group, and a is an integer of 1 to 3. Furthermore, in the polymerizable group shown in (■) above, R
is a monovalent hydrocarbon group, b is 2 or 3,
C is an integer of 1 to 3, d and e are each integers of 0 to 2, and the relationship c+d+e=3.

In such a silicone monomer, the number of repeating units of organosiloxane is preferably 10 or more and 1000 or less. This is because if the number of units is less than 10, the formed polymer becomes hard and it is difficult to obtain the softness that is a characteristic of silicone.
This is because when the number of units is larger than 00, the ratio of polymerizable groups to the entire monomer is small, and the polymerization rate may be slow or may not be polymerized. One or more of such monomers may be appropriately selected and used. It goes without saying that such a silicone monomer can also be used in a balloon body.

Next, a photoinitiator used as another essential component of the present invention will be described. In the present invention, common photoinitiators are used, including ultraviolet absorbers.

However, since the polymerization of the composition of the present invention takes place within the eye, it is preferable to use a light source that does not contain much light with a wavelength of less than 340 nm for eye safety. , it is desirable that the photoinitiator has a large initiation ability against such light.

The number of initiators used may be one, or two or more types may be used in combination for the purpose of improving the initiation ability. It is preferably blended in a proportion of about 0.05% to 5% by weight. If the blending amount is less than 0.01% by weight, the sensitivity will be low and curing may take a long time or may not occur at all. Furthermore, if it is added in an amount greater than 10% by weight, there is a risk of foaming, and an effect commensurate with the amount added may not be obtained.

Specific examples of photoinitiators include acetophenones such as acetophenone, di- and trichloroacetophenone, dialkoxyacetophenone, 2,2-dimethoxy-2phenylacetophenone, 4-dialkylaminoacetophenone, and 22-jethoxyacetophenone. benzophenones such as benzophenone, 4.4'-bis(dimethylamino)benzophenone (Michler's ketone), and 4.4'-bis(diethylamino)benzophenone;benzyl; benzoins such as benzoin and benzoin alkyl ether; benzyl dimethyl ketal; benzoyl Benzoate; α-aziroxime esters; tetramethylthiuram monosulfide; thioxanthone such as thioxanthone, 2-chlorothioxanthone, diethylthioxanthone; azo compounds such as azobisisobutyronitrile; benzoyl peroxide, di-tert -Peroxides such as 7'-chill peroxide; benzoyljethoxyphosphine oxide; trimethylbenzoyldiphenylphosphine oxide; camphorquinone; 5
-Butylbarbic acid and the like can be mentioned.

Since the composition of the present invention contains the photopolymerizable monomer and such a photoinitiator and has photocurability, it can be cured within the eye in a short time by irradiating it with a predetermined light. This prevents the injection material from leaking out of the injection port.

In addition to the photopolymerizable monomer and the photoinitiator, the composition for forming an intraocular lens of the present invention may optionally contain a sensitizer, a hardness adjusting component, a dye, etc. It goes without saying that this is the case.

A sensitizer alone cannot be activated by ultraviolet irradiation, but when used together with a photoinitiator, it exhibits a better effect than when the photoinitiator is used alone. The amount used is 0.0 based on the total amount of the composition.
The content will be approximately 1 to 10% by weight. This is because even if the amount exceeds 10 weight, no effect commensurate with the amount added can be expected. Specific examples thereof include amines such as n-butylamine, di-n-butylamine, and triethylamine; tri-n-butylphosphine-1allylthiourea; S-benzylisothiuronium-p-toluenesulfinate; dimethylaminoethyl methacrylate ; Diethylaminoethyl methacrylate and the like can be mentioned.

The hardness adjusting component is a component that is added to the monomer so that the intraocular lens after curing has a desired hardness, and a component that has good compatibility with the monomer and does not lose transparency even after curing is used. For example, silicone oil, polyethylene glycol, etc. are used.

The amount used is 0.01 to 7% based on the total amount of the composition.
It is said to be about 5% by weight. If it exceeds 75% by weight, it takes a long time to cure and may not cure, which is not preferable.

In addition, the human crystalline lens is not strictly transparent, but is colored in elderly people, who account for the majority of people who have IOLs inserted, so if an IOL is inserted in only one eye, the color vision of the left and right eyes will match. It is also possible to mix dyes for this purpose. The dye may be polymerizable or non-polymerizable, and may be used in amounts of 0. It will be blended at a ratio of about 1 to 1% by weight of OO. If the amount is more than 1% by weight, the coloring will be excessive and the light transmittance will be reduced. Then, each of these optional components is blended into the composition consisting of the photopolymerizable polymer and the photoinitiator to obtain the composition for forming an intraocular lens according to the present invention.

In order to inject such an intraocular lens forming composition into the lens capsule or into a balloon housed within the lens capsule, a catheter or the like is used and through a small incision according to the same method as in the past. However, since the composition of the present invention is in liquid form, it can be injected very easily.

By applying light irradiation after injection, polymerization can be completed in a short period of time, which prevents the injection material from leaking out of the injection port and allows the formation of a good intraocular lens. . In addition, by selecting the appropriate photoinitiator, 340 nm, which is harmful to the eye, can be
Since photopolymerization can be carried out without much use of shorter wavelength light, it is also safer.

(Examples) Below, some examples of the present invention will be shown to clarify the present invention more specifically, but the present invention is not limited in any way by the description of such examples. Needless to say, it is not something that can be accepted.

In addition to the following examples and the above-mentioned specific description, the present invention includes various changes, modifications, and changes based on the knowledge of those skilled in the art, as long as they do not depart from the spirit of the present invention. It should be understood that improvements and the like may be made.

The silicone monomers used in this example have the structures shown below, and are hereinafter referred to as organosiloxane A, organosiloxane B, and organosiloxane C, respectively.

<Organosiloxane A><OrganosiloxaneC> H3 <Organosiloxane B> I3 Example 1 100 parts by weight of organosiloxane A as a photopolymerizable monomer and 1 part by weight of 2,2-jethoxyacetophenone as a photoinitiator. Mix and prepare the injection material.

This injection material was injected through a catheter into a rabbit eye that had previously had its capsule left and the lens parenchyma removed. After injection,
Halogen light from a surgical microscope (Tokyo Kogaku Kikai 0M5-70, the same applies hereafter) (Philips bulb: 15, 1
When the injection material was continuously irradiated with 50 W (the same applies hereinafter) from a distance of 17 cm, the injection material hardened after several minutes. After that, the surgery was completed with sutures.

After 3 months, the rabbit's eye with the intraocular lens inserted was removed and the retina was observed, and no abnormality was found in the retina. Furthermore, when the intraocular lens was removed along with the lens capsule and observed, there was no leakage of the injection material and no wrinkles were observed on the surface of the lens capsule, indicating that the intraocular lens had good optical performance. .

Example 2 75 parts by weight of organosiloxane B as a photopolymerizable monomer, 1 part by weight of 2,2-jetoxyacetophenone as a photoinitiator, and 25 parts by weight of silicone oil as a hardness adjusting component were mixed and injected. Materials were prepared.

Next, this injection material was directly injected into the lens capsule of a rabbit eye in the same manner as in Example 1, and when irradiated with light under the same conditions, it hardened within a few minutes. After that, sutures were applied and the surgery was completed.

After 3 months, the retina and lens capsule were observed in the same manner as in Example 1. There were no retinal abnormalities, and no leakage of the injection material or wrinkles was observed in the lens capsule, indicating that the intraocular lens had good optical performance. A product with good performance and lower hardness than Example 1 was obtained.

Example 3 A pouring material was prepared by mixing 100 parts by weight of organosiloxane C as a photopolymerizable monomer and 0.2 parts by weight of camphorquinone as a photoinitiator.

This injection material was directly injected into the lens capsule of a rabbit eye in the same manner as in Example 1. After injection, use a UV cut filter (
Using a polymethyl methacrylate disc with a diameter of 90M and a thickness of 1 mm containing 1% by weight of hensifhenone (the same applies hereafter), only the visible light of the halogen light from a surgical microscope can be absorbed by 17C.
After a few minutes of continuous illumination from a distance of m, the injection material hardened. After that, the surgery was completed with sutures.

After 3 months, the retina and lens capsule were observed in the same manner as in Example 1. There was no retinal abnormality, and no leakage of the injected lens or wrinkles was observed in the lens capsule, and the intraocular lens was in good condition. It had optical performance.

Example 4 100 parts by weight of trimethylolpropane trimethacrylate as a photopolymerizable monomer, 0.1 part by weight of acetophenone as a photoinitiator, and 0.1 part by weight of n-butylamine as a sensitizer were mixed to form an injection material. Prepared.

This injection material was injected through a catheter into a balloon body serving as an intraocular lens body that had been previously inserted into a rabbit eye from which the lens capsule had been left and the lens parenchyma had been removed. After injection,
When irradiated with light under the same conditions as in Example 1, it was cured within a few minutes. After that, the surgery was completed with sutures.

After 3 months, the rabbit's eye with the intraocular lens inserted was removed and the retina was observed. No retinal abnormalities were found. Also, when the intraocular lens was removed and observed, there was no leakage of the injection material or the surface of the balloon. No wrinkles were observed, and the intraocular lens had good optical performance.

Example 5 As a photopolymerizable monomer, 70% of 2,2-bis-(3methacrylic, 2-hydroxypropoxyphenyl)propane
3 parts by weight and triethylene glycol dimethacrylate
An injection material was prepared by mixing 3 parts by weight of camphorquinone and 2 parts by weight of 5-butylbarbic acid as photoinitiators.

The obtained injection material was injected into the eye of a rabbit using a balloon body in the same manner as in Example 4. After injection, use a 17 CT Philips tungsten lamp (24 x 250 W).
Irradiation was continued from a distance of 11, and the injection material hardened after a few minutes. After that, sutures were performed and the surgery was completed.

After 3 months, the rabbit's eye with the intraocular lens inserted was removed and the retina was observed, and there was no retinal abnormality.When the intraocular lens was removed and observed, leakage of the injection material and wrinkles on the balloon surface were found. No defects were observed, and the intraocular lens had good optical performance.

Example 6 The same composition as in Example 4 was injected into the eye of a rabbit using a balloon body in the same manner as in Example 4. After the injection, we continued to irradiate only the visible light of halogen light from a surgical microscope from a distance of 17 cm using a UV cut filter.
The injection material did not harden even after several tens of minutes had passed. Then, U
■When the cut filter was removed and halogen light continued to be irradiated, the injection material hardened after a few minutes. After that, the surgery was completed with sutures.

After 3 months, the rabbit's eye with the intraocular lens inserted was removed and the retina was observed, and no retinal abnormalities were found. No wrinkles were observed, and the intraocular lens had good optical performance.

Comparative Example 1 A gel-like sodium hyaluronate aqueous solution was used as the injection material.

When this injection material was injected through a catheter into the balloon body, which serves as the intraocular lens body, that had been previously inserted into a rabbit eye from which the lens parenchyma had been removed, leaving the capsule behind, the injection material had a high viscosity and was quite difficult to inject. Met. After the injection, sutures were performed and the surgery was completed.

After 3 months, the above intraocular lens was extracted and observed, and it was confirmed that the injection material had leaked significantly and that it had hardly formed a lens shape.

Comparative Example 2 As monomers, 2 parts by weight of vinyl polydimethylsiloxane [the number of repeating siloxane units (n) is 560 and contains 3 vinylsilane units in the molecular chain] and hydrogenated polydimethylsiloxane [repeating siloxane] were used. Number of units (
n) is 190 and contains three silicon hydride units in the molecular chain], and a vinyltrimethoxysilane complex of platinic acid as a catalyst is mixed uniformly with
The injection material was prepared by mixing pp.

This injection material was injected through a catheter into a balloon body serving as an intraocular lens body that had been previously inserted into a rabbit eye from which the lens capsule had been left and the lens parenchyma had been removed. The injection material cured in a few hours at 37°C.

When the intraocular lens was then extracted and observed, evidence of leakage of the injection material from the injection port was observed, and wrinkles were observed on the balloon surface, making it impossible to obtain satisfactory optical performance.

As is clear from the above results, since the composition for forming an intraocular lens according to the present invention has photocurability, it has a low viscosity and is easy to inject, and cures within a few minutes using light after injection. This prevents the injection material from leaking out from the injection port, making it possible to obtain an intraocular lens with a desired shape. When using a silicone monomer, it can be injected directly into the lens capsule, whereas when using a balloon body, the photopolymerizable monomer can be freely selected. .

In addition, the light source used for polymerization may be a halogen lamp, a tungsten lamp, etc., which are commonly used for eye surgery and do not contain much light with a wavelength of less than 340 nm, which is considered harmful to the eyes. It is excellent.

Claims (3)

[Claims] (1) A composition for forming an intraocular lens, which contains a photopolymerizable monomer and a photoinitiator, and which is polymerized in the eye to provide a desired intraocular lens. (2) The composition for forming an intraocular lens according to claim 1, wherein the photopolymerizable monomer is a silicone monomer and is injected directly into the lens capsule of the eye. (3) The composition for forming an intraocular lens according to claim (1), which is injected into a balloon body housed in a lens capsule in the eye.