WO1997001114A1 - Contact and intraocular lenses containing ultraviolet absorbers and method of their production - Google Patents
Contact and intraocular lenses containing ultraviolet absorbers and method of their production Download PDFInfo
- Publication number
- WO1997001114A1 WO1997001114A1 PCT/CZ1996/000016 CZ9600016W WO9701114A1 WO 1997001114 A1 WO1997001114 A1 WO 1997001114A1 CZ 9600016 W CZ9600016 W CZ 9600016W WO 9701114 A1 WO9701114 A1 WO 9701114A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- methacrylates
- acrylates
- alkyl
- alkyloxy
- contact
- Prior art date
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Classifications
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
- G02B1/043—Contact lenses
Definitions
- the invention relates to contact and intraocular lenses containing absorbers of ultraviolet radiation and to the method of their production.
- the undamaged eye possesses the ability to resist, for a certain time, the ultraviolet radiation that is a constituent of daylight. Slow biochemical and physiological changes caused by the radiation in the eye are accelerated to a considerable extent if the eye is damaged in whatever way. On long-term action of ultraviolet radiation, the protecting mechanism of the eye fails and an irreversible damage of cornea, lens or retina results. According to the latest findings, the danger of damaging the vision considerably increases if the atmospheric ozone layer deteriorates.
- UV absorbers are substances capable of absorbing the radiation in this wavelength range.
- a self-evident prerequisite for these substances is that,if used, they are incorporated into the lens material in such a way that they cannot be removed by common extraction procedures since only thus they can form an effective protection of the eye against ultraviolet radiation.
- the aim of this invention is contact and intraocular lenses containing UV absorbers and their preparation by polymerization of a mixture of suitable monomers, initiators, crosslinking agent and polymerizable UV absorbers in such a way that the resulting contact or intraocular lens absorbs all the transmitting ultraviolet light.
- the object of the invention is contact and intraocular lenses with UV absorbers formed by a polymer consisting of 89 to 99.6 wt. % of vinyl monomers, 0.2 to 6 wt.% of polymerizable UV absorbers, 0.1 to 3 wt. % of a crosslinking
- the contact and intraocular lenses according to the invention are formed by a polymer containing vinyl monomers selected from the group comprising alkyl acrylates and methacrylates, hydroxyalkyl acrylates and methacrylates,
- fluoroalkyl acrylates and methacrylates (alkyloxy)alkyl acrylates and methacrylates, (acyloxy) lkyl acrylates and methacrylates, acylaminoalkyi acrylates and methacrylates, (alkylsulfinyl)alkyl acrylates and methacrylates, (alkylsul ⁇ fonyl)alkyl acrylates andmethacrylates, tris(alkyloxy)silyl-
- alkyl acrylates and methacrylates N-vinylpyrrolidone, N-vinylpiperidone and their combinations, where alkyl is an alkyl with 1 to 4 carbon atoms.
- the polymer for the contact and intraocular lenses according to this invention contains, as polymerizable UV
- absorbers substances selected from the group of substances comprising the substances of general formula I or II,
- Rl, R2 are hydrogen, acryloyloxy, methacryloyloxy,
- R3, R4 are hydrogen, hydroxy, halogen, cyano, alkylox , alkyl, (alkyloxy)alkyl, hydroxyalkyl groups, the alkyls being alkyls with 1 to 4 carbon atoms or III or IV
- R is acryloyl or methacryloyl group or their mixtures.
- crosslinking agents substances selected from the group comprising acrylic and methacrylic esters of dihydric alcohols, amino alcohols, amines, allyl acrylates and methacrylates and diallyl esters of dicarboxylic acids are suitable.
- polymerization initiators azo and peroxy initiators and initiators cleavable by UV radiation are used.
- the method of preparation of contact and intraocular lenses consists in polymerization or copolymerization of vinyl monomers performed in the presence of polymerizable UV absorbers, a crosslinking agent and a polymerization initiator straight in the respective moulds.
- the preparation of both contact and intraocular lenses proceeds in such a way that polymerization mixtures containing a polymerizable UV absorber are charged into moulds and polymerized.
- transmittance is plotted of a contact lens prepared from a mixture of monomers containing N-vinylpyr ⁇ rolidone and 2-(acetyloxy)ethyl methacrylate and a UV absorber, 2-hydroxy-4-(2-(methacryloyloxy)ethyloxy)benzo ⁇ phenone, in given concentrations prepared according to Example 2.
- Central thickness of the lens is 0.13 mm.
- Figure 3 is UV spectrum of 2-hydroxy-4-(2-(methacryloyl ⁇ oxy)ethyloxy)benzophenone.
- a stock solution of the polymerizable mixture contained: 25 ml 2-hydroxyethyl methacrylate containing 0.12 wt. % ethylene dimethacrylate, 30 1 ethylene dimethacrylate (its content in the polymerizable mixture is 0.3 wt. %) and 0.025g 2,2 ' -azobis(isobutyronitrile) . From the stock solution, the following mixtures containing various amounts of the UV absorber, 2-hydroxy-4-methacryloyloxy-2'-(methoxycarbonyl) benzophenone, were prepared:
- the following mixture of monomers wa ⁇ used for prepa- ration of intraocular lenses 1.02 g methacrylic acid, 31.4 g 2-hydroxyethyl methacrylate, 3.29 g glycerol, 0.07 g ethylene dimethacrylate, 0.14 g diisopropyl peroxycarbonate and 1.63 g 2-hydroxy-4-(2-(methacryloyloxy)ethyloxy)ben ⁇ zophenone.
- Argon was bubbled through the polymerization mixture which was then charged into polymerization moulds in amounts of 40 ⁇ l. Polymerization was performed in the atmosphere of carbon dioxide at 70°C for 2 hours. Intraocular lenses were soaked in a 5 % hydrogen carbonate solution and then in physiological solution.
- Intraocular lenses were prepared from the following polymerization mixture: 65 g 2-hydroxyethyl methacrylate, 6.5 g glycerol, 0.14 g ethylene dimethacrylate, 0.25 g 2,2'-azo- bis(isobutyronitrile) , 3.2 g 4-methacryloyloxy-2-hydroxy- benzophenone.
- the resulting lenses were worked up analogously to Example 4.
Abstract
The invention concerns contact and intraocular lenses formed by a polymer from 89 to 99.6 % of vinyl monomers, 0.2 to 6 wt.% of polymerizable absorbers of ultraviolet radiation, 0.1 to 3 wt.% of a crosslinker and 0.1 to 2 wt.% of a polymerization initiator. As vinyl monomers, the monomers are used selected from the group comprising alkyl acrylates and methacrylates, hydroxyalkyl acrylates and methacrylates, fluoroalkyl acrylates and methacrylates, (alkyloxy)alkyl acrylates and methacrylates, (acyloxy)alkyl acrylates and methacrylates, (acylamino)alkyl acrylates and methacrylates, (alkylsulfinyl)alkyl acrylates and methacrylates, (alkylsulfonyl)alkyl acrylates and methacrylates, tris(alkyloxy)silylalkyl acrylates and methacrylates, N-vinylpyrrolidone, N-vinylpiperidone and their combinations. As polymerizable absorbers of ultraviolet radiation, substances selected from the group of substances comprising substances of general formula (I) or (II) are used where R1, R2 are hydrogen, acryloyloxy, methacryloyloxy, (acryloyloxy)alkyloxy, (methacryloyloxy)alkyloxy, 3-(methacryloyloxy)-2-hydroxypropyloxy, vinyl, allyloxy, (acryloylamino)methyl, (methacryloylamino)methyl groups, R3, R4 are hydrogen, hydroxy, halogen, cyano, alkyloxy, alkyl, (alkyloxy)alkyl, hydroxyalkyl groups, the alkyls being alkyl groups with 1 to 4 carbon atoms or (III) or (IV), where R is acryloyl or methacryloyl group, or their mixture. As cross-linking agents, substances are used selected from the group comprising acrylic and methacrylic esters of dihydric alcolhols, amino alcohols, amines, allyl acrylates and methacrylates and diallyl esters of dicarboxylic acids and as polymerization initiators, common azo and peroxy initiators and initiators cleavable by UV radiation.
Description
Description
Contact and intraocular lenses containing ultraviolet absorbers and method of their production
Technical Field
The invention relates to contact and intraocular lenses containing absorbers of ultraviolet radiation and to the method of their production.
Background Art
The undamaged eye possesses the ability to resist, for a certain time, the ultraviolet radiation that is a constituent of daylight. Slow biochemical and physiological changes caused by the radiation in the eye are accelerated to a considerable extent if the eye is damaged in whatever way. On long-term action of ultraviolet radiation, the protecting mechanism of the eye fails and an irreversible damage of cornea, lens or retina results. According to the latest findings, the danger of damaging the vision considerably increases if the atmospheric ozone layer deteriorates.
This is why it is important that contact and intraocular lenses also protect the eye against ultraviolet radiation. One ofthe basic requirements on modern polymer materials for preparation of contact and intraocular lenses is therefore their ability to absorb completely UV radiation C (180-280 μm) and UV radiation B (280-315μm). Substances capable of absorbing the radiation in this wavelength range are called UV absorbers. A self-evident prerequisite for these substances is that,if used, they are incorporated into the lens material in such a way that they cannot be removed by common extraction procedures since only thus they can form an effective protection of the eye against ultraviolet radiation.
The aim of this invention is contact and intraocular lenses containing UV absorbers and their preparation by polymerization of a mixture of suitable monomers, initiators,
crosslinking agent and polymerizable UV absorbers in such a way that the resulting contact or intraocular lens absorbs all the transmitting ultraviolet light.
5 Disclosure of Invention
The object of the invention is contact and intraocular lenses with UV absorbers formed by a polymer consisting of 89 to 99.6 wt. % of vinyl monomers, 0.2 to 6 wt.% of polymerizable UV absorbers, 0.1 to 3 wt. % of a crosslinking
10 agent and 0.1 to 2wt. % of a polymerization initiator.
The contact and intraocular lenses according to the invention are formed by a polymer containing vinyl monomers selected from the group comprising alkyl acrylates and methacrylates, hydroxyalkyl acrylates and methacrylates,
15. fluoroalkyl acrylates and methacrylates, (alkyloxy)alkyl acrylates and methacrylates, (acyloxy) lkyl acrylates and methacrylates, acylaminoalkyi acrylates and methacrylates, (alkylsulfinyl)alkyl acrylates and methacrylates, (alkylsul¬ fonyl)alkyl acrylates andmethacrylates, tris(alkyloxy)silyl-
20 alkyl acrylates and methacrylates, N-vinylpyrrolidone, N-vinylpiperidone and their combinations, where alkyl is an alkyl with 1 to 4 carbon atoms.
The polymer for the contact and intraocular lenses according to this invention contains, as polymerizable UV
25 absorbers, substances selected from the group of substances comprising the substances of general formula I or II,
II
35 where Rl, R2 are hydrogen, acryloyloxy, methacryloyloxy,
(acryloyloxy)alkyloxy, (methacryloyloxy)alkyloxy, 3-( etha¬ cryloyloxy)-2-hydroxypropyloxy, vinyl, allyloxy, (acryloyl- amino)methyl,( ethacryloylamino)methyl groups;
R3, R4 are hydrogen, hydroxy, halogen, cyano, alkylox , alkyl, (alkyloxy)alkyl, hydroxyalkyl groups, the alkyls being alkyls with 1 to 4 carbon atoms or III or IV
where R is acryloyl or methacryloyl group or their mixtures.
As crosslinking agents, substances selected from the group comprising acrylic and methacrylic esters of dihydric alcohols, amino alcohols, amines, allyl acrylates and methacrylates and diallyl esters of dicarboxylic acids are suitable.
As polymerization initiators, azo and peroxy initiators and initiators cleavable by UV radiation are used. The method of preparation of contact and intraocular lenses consists in polymerization or copolymerization of vinyl monomers performed in the presence of polymerizable UV absorbers, a crosslinking agent and a polymerization initiator straight in the respective moulds. The preparation of both contact and intraocular lenses proceeds in such a way that polymerization mixtures containing a polymerizable UV absorber are charged into moulds and polymerized.
In Figure 1, transmittance is plotted of a contact lens prepared from a mixture of monomers containing N-vinylpyr¬ rolidone and 2-(acetyloxy)ethyl methacrylate and a UV absorber, 2-hydroxy-4-(2-(methacryloyloxy)ethyloxy)benzo¬ phenone, in given concentrations prepared according to
Example 2. Central thickness of the lens is 0.13 mm.
In Figure 2 transmittance is plotted of a contact lens prepared from the monomer 2-hydroxyethyl methacrylate and the UV absorber 2-[2-hydroxy-3-( (methacryloyla ino)methyl)-5- methylphenyl]-2H-benzotriazole, in the concentrations given in Example 3.
Figure 3 is UV spectrum of 2-hydroxy-4-(2-(methacryloyl¬ oxy)ethyloxy)benzophenone.
In Figure 4, UV spectrum of 2-[2-hydroxy-3-( (methacryl- oylamino)methyl)-5-methylphenyl]-2H-benzotriazole is given.
The invention is elucidated in the examples without limiting its scope to them.
Examples
Example 1
A stock solution of the polymerizable mixture contained: 25 ml 2-hydroxyethyl methacrylate containing 0.12 wt. % ethylene dimethacrylate, 30 1 ethylene dimethacrylate (its content in the polymerizable mixture is 0.3 wt. %) and 0.025g 2,2'-azobis(isobutyronitrile) . From the stock solution, the following mixtures containing various amounts of the UV absorber, 2-hydroxy-4-methacryloyloxy-2'-(methoxycarbonyl) benzophenone, were prepared:
6 ml of stock solution + 0.048 g of UV absorber (0.8 wt. %) 6 ml of stock solution + 0.23 g of UV absorber (2 wt. %), 6 ml of stock solution + 0.18 g of UV absorber (3 wt. %). Argon was bubbled through the polymerization mixtures for 10 min, the mixtures were transferred to polypropylene dishes for preparation of contact lenses (volume 1 ml) and polymerized in argon stream at 60°C for 24 h. The resulting polymer blocks were heated to 105°C for 3 h. Lenses of a central thickness of 0.13 mm were prepared from the blocks by lathe cutting.
Example 2
Contact lenses were prepared analogously to Example 1
from the following mixture: 12 g 2-acetyloxyethylmeth- acrylate, 18 g N-vinylpyrrolidone, 0.09 g 3,3 '-ethylidene- bis(N-vinyl-2-pyrrolidone) , 0.015 g 2,2 '-azobisisobutyro¬ nitrile) (AIBN). 2-Hydroxy-4-( (2-methacryloyloxy)ethyl- oxy)benzophenone was used as an UV absorber. Polymerization mixtures were prepared where the content of the UV absorber ranged from 0.1 to 5 wt. %. The measured transmittances are plotted in Fig. 1.
Example 3
From the polymerization mixture according to Example 1 and UV absorber, 2-[2-hydroxy-3-( (methacryloylamino) methyl)- -5-methylphenyl]-2H-benzotriazole in the amount 0.8-2 wt.%, contact lenses were prepared by lathe cutting after polymeri- zation according to Example 1. The measured transmittances are plotted in Fig. 2.
Example 4
The following mixture of monomers waε used for prepa- ration of intraocular lenses: 1.02 g methacrylic acid, 31.4 g 2-hydroxyethyl methacrylate, 3.29 g glycerol, 0.07 g ethylene dimethacrylate, 0.14 g diisopropyl peroxycarbonate and 1.63 g 2-hydroxy-4-(2-(methacryloyloxy)ethyloxy)ben¬ zophenone. Argon was bubbled through the polymerization mixture which was then charged into polymerization moulds in amounts of 40 μl. Polymerization was performed in the atmosphere of carbon dioxide at 70°C for 2 hours. Intraocular lenses were soaked in a 5 % hydrogen carbonate solution and then in physiological solution.
Example 5
Intraocular lenses were prepared from the following polymerization mixture: 65 g 2-hydroxyethyl methacrylate, 6.5 g glycerol, 0.14 g ethylene dimethacrylate, 0.25 g 2,2'-azo- bis(isobutyronitrile) , 3.2 g 4-methacryloyloxy-2-hydroxy- benzophenone. The resulting lenses were worked up analogously to Example 4.
Claims
Contact and intraocular lenses with absorbers of ultraviolet radiation characterized in that they are formed by a polymer consisting of 89 to 99.6 wt. % of vinyl monomers, 0.2 to 6 wt. % of polymerizable absorbers of ultraviolet radiation, 0.1 to 3wt.% of a crossiinker and 0.1 to 2 wt.% of a polymer initiator.
2. Contact and intraocular lenses according to claim 1, characterized in that they are formed by a polymer containing vinyl monomers selected from the group comprising alkyl acrylates and methacrylates, hydroxyalkyl acrylates and methacrylates, fluoroalkyl acrylates and methacrylates, (alkyloxy)alkyl acrylates and methacrylates, (acyloxy) lkyl acrylates and methacrylates, (acylamino)alkyl acrylates and methacrylates, (alkylsulfinyl)alkyl acrylates and methacrylates, ( lkylsulfonyl)alkyl acrylates and methacrylates, tris(alkylox )silylalkyl acrylates and methacrylates, N-vinylpyrrolidone, N-vinylpiperidoneand their combinations, where the alkyls are alkyl groups with 1 to 4 carbon atoms.
3. Contact and intraocular lenses according to claims 1 and 2 characterized in that they are formed by a polymer containing, as polymerizable absorbers of ultraviolet light, the substances selected from the group of substances comprising substances of the general formula I or II
II where Rl, R2 are hydrogen, acryloyloxy, methacryloyloxy, (acryloyloxy)alkyloxy, (methacryloyloxy)alkyloxy, 3-(methacryloyloxy)-2-hydroxypropyloxy, vinyl, allyloxy, (aeryloylamino)methyl, (methacryloylamino)methyl groups; R3, R4 are hydrogen, hydroxy, halogen, cyano, alkyloxy, alkyl, (alkyloxy)alkyl, hydroxyalkyl groups, the alkyls being alkyl groups with 1 to 4 carbon atoms or III or IV
where R is acryloyl or methacryloyl group, or their mixture.
4. Contact and intraocular lenses according to claims 1 to 3 characterized in that they are formed by a polymer containing, as crosslinking agents, substances selected from the group comprising acrylic and methacrylic esters of dihydric alcohols, amino alcohols, amines, allyl acrylates and methacrylates and diallyl esters of dicarboxylic acid.
5. Contact and intraocular lenses according to claims 1 to 4 characterized in that they are formed by a polymer containing, as polymerization initiators, azo and peroxy initiators and initiators cleavable by UV radiation.
6. The method of preparation of contact and intraocular lenses according to claims 1 to 5, characterized in that the polymerization or copolymerization of vinyl monomers is performed in the presence of polymerizable absorbers of ultraviolet radiation, a crosslinking agent and a polymerization initiator straight in the respective mould.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CZ951614A CZ284063B6 (en) | 1995-06-20 | 1995-06-20 | Contact and intraocular lenses with absorbers of ultraviolet radiation and process for producing thereof |
| CZPV1614-95 | 1995-06-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1997001114A1 true WO1997001114A1 (en) | 1997-01-09 |
Family
ID=5463546
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/CZ1996/000016 WO1997001114A1 (en) | 1995-06-20 | 1996-06-19 | Contact and intraocular lenses containing ultraviolet absorbers and method of their production |
Country Status (2)
| Country | Link |
|---|---|
| CZ (1) | CZ284063B6 (en) |
| WO (1) | WO1997001114A1 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0899590A2 (en) * | 1997-08-29 | 1999-03-03 | Nidek Co., Ltd | Ultraviolet absorbing base material |
| US6147170A (en) * | 1998-08-17 | 2000-11-14 | E. I. Du Pont De Nemours And Company | UV stabilized ethylene copolymers |
| EP1666537A1 (en) * | 2004-11-10 | 2006-06-07 | Nidek Co., Ltd. | Colorant for ocular lenses and material for colored ocular lenses using the colorant |
| CN115466349A (en) * | 2022-09-28 | 2022-12-13 | 长春工业大学 | Benzophenone derivative ultraviolet-proof silicone hydrogel contact lens and preparation method thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4304895A (en) * | 1973-06-20 | 1981-12-08 | Wesley-Jessen, Inc. | Ultraviolet absorbing corneal contact lenses |
| US4390676A (en) * | 1976-11-15 | 1983-06-28 | Schering Corporation | Ultraviolet absorbing lenses |
| EP0343996A2 (en) * | 1988-05-26 | 1989-11-29 | Alcon Laboratories, Inc. | Ultraviolet absorbing hydrogels |
| US5084537A (en) * | 1985-01-29 | 1992-01-28 | Bausch & Lomb, Incorporated | UV-absorbing extended-wear Lenses |
| EP0488145A2 (en) * | 1990-11-26 | 1992-06-03 | Menicon Co., Ltd. | Ultraviolet light absorbing ocular lens |
-
1995
- 1995-06-20 CZ CZ951614A patent/CZ284063B6/en not_active IP Right Cessation
-
1996
- 1996-06-19 WO PCT/CZ1996/000016 patent/WO1997001114A1/en active Application Filing
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4304895A (en) * | 1973-06-20 | 1981-12-08 | Wesley-Jessen, Inc. | Ultraviolet absorbing corneal contact lenses |
| US4390676A (en) * | 1976-11-15 | 1983-06-28 | Schering Corporation | Ultraviolet absorbing lenses |
| US5084537A (en) * | 1985-01-29 | 1992-01-28 | Bausch & Lomb, Incorporated | UV-absorbing extended-wear Lenses |
| EP0343996A2 (en) * | 1988-05-26 | 1989-11-29 | Alcon Laboratories, Inc. | Ultraviolet absorbing hydrogels |
| EP0488145A2 (en) * | 1990-11-26 | 1992-06-03 | Menicon Co., Ltd. | Ultraviolet light absorbing ocular lens |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0899590A2 (en) * | 1997-08-29 | 1999-03-03 | Nidek Co., Ltd | Ultraviolet absorbing base material |
| EP0899590A3 (en) * | 1997-08-29 | 2000-01-12 | Nidek Co., Ltd | Ultraviolet absorbing base material |
| US6096846A (en) * | 1997-08-29 | 2000-08-01 | Nidek Co., Ltd. | Ultraviolet absorbing base material |
| US6147170A (en) * | 1998-08-17 | 2000-11-14 | E. I. Du Pont De Nemours And Company | UV stabilized ethylene copolymers |
| EP1666537A1 (en) * | 2004-11-10 | 2006-06-07 | Nidek Co., Ltd. | Colorant for ocular lenses and material for colored ocular lenses using the colorant |
| US7232896B2 (en) | 2004-11-10 | 2007-06-19 | Nidek Co., Ltd. | Colorant for ocular lenses and material for colored ocular lenses using the colorant |
| CN115466349A (en) * | 2022-09-28 | 2022-12-13 | 长春工业大学 | Benzophenone derivative ultraviolet-proof silicone hydrogel contact lens and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CZ284063B6 (en) | 1998-08-12 |
| CZ161495A3 (en) | 1997-01-15 |
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