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IIIHIIII US005374663A United States Patent (19) 11 Patent Number: 5,374,663 Daicho Et Al

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IIIHIIII US005374663A United States Patent (19) 11 Patent Number: 5,374,663 Daicho Et Al IIIHIIII US005374663A United States Patent (19) 11 Patent Number: 5,374,663 Daicho et al. 45 Date of Patent: Dec. 20, 1994 54 PROCESS FOR PRODUCING 4,390,676 6/1983 Loshack.......................... 351/160 H. CYANOPSLA-CORRECTABLE 4,559,059 12/1985 Su ........................................ 351/162 4,795,461 1/1989 Lundquist et al. .................. 523/106 INTRAOCULARLENS 4,863,466 9/1989 Schlegel ............. ... 351/162 75 Inventors: Masanori Daicho, Kodama; Yuuichi 4,921,205 5/1990 Drew, Jr. et al. ................... 264/1.7 Yokoyama, Kounosu; Makoto Tsuchiya, Honjo, all of Japan FOREIGN PATENT DOCUMENTS 73) Assignee: Hoya Corporation, Tokyo, Japan 2255901 11/1987 Japan ................................... 351/177 21 Appl. No.: 7,027 OTHER PUBLICATIONS 22 Filed: Jan. 21, 1993 CA 110(12): 96748p, May 1988 (Frontini). Primary Examiner-Paul R. Michl Related U.S. Application Data Assistant Examiner-Andrew E. C. Merriam I63) Continuation of Ser. No. 815,611, Jan. 7, 1992, aban Attorney, Agent, or Firm-Nixon & Vanderhye doned, which is a continuation of Ser. No. 432,758, 57 ABSTRACT filed as PCT/JP89/00230, Mar. 3, 1989, abandoned. The present invention relates to a process for producing 30 Foreign Application Priority Data a cyanopsia-correctable intraocular lens, which process Mar. 3, 1988 JP Japan ........................................ 63-50394 is characterized by, in polymerizing a monomer capable 51) Int. Cl.............................................. A61 L 27/00 of forming a transparent lens material upon polymeriza 52 U.S.C. .................................... 523/106; 351/162; tion to obtain an intraocular lens, adding, as an essential 623/6; 514/912; 514/972 component, at least one member of yellow, yellowish 58) Field of Search ........................ 351/162; 523/106; brown and orange colorants and, as an optional compo 623/6; 514/912,972 nents, an U.V. absorber and a crosslinking monomer. The intraocular lens obtained by the present invention (56) References Cited has a light absorption characteristic close to that of U.S. PATENT DOCUMENTS human crystalline lens and is effective for correction of 4,102,567 7/1978 Cuffe et al. ......................... 351/162 cyanopsia. 4,260,768 4/1981 Lorenz et al. ....................... 526/259 4,328,148 5/1982 Kuzma ................................ 523/06 16 Claims, 5 Drawing Sheets OO 3O 2O g 3OO 35C 4OO 45O 5OO 55O 6OO 65O 7OO WAVENUMBER (nm) U.S. Patent Dec. 20, 1994 Sheet 1 of 5 5,374,663 F G. OO 9O 3O 2O O O 3OO 35O 4OO 45O 5OO 55O 6OO 65O 70O WAVENUMBER (nm) F G. 2 OO 9O 3O 2O O 3OON 350 4OO 45O 5OO 55O 6OO 650 7OO WAVENUMBER - (n-n) U.S. Patent Dec. 20, 1994 Sheet 2 of 5 5,374,663 F G. 3 OO 9O 3O 2O O O 3OO 35O 4OO 45O 5OO 55O 6OO 650 7OO WAVENUMBER (nm) F G. 4 OO 9O 8O 7O 6O 5O 4O 3O 2O O O 3OO 350 4OO 45O 5OO 55O 6OO 650 7OO WAVENUMBER (nm) U.S. Patent Dec. 20, 1994 Sheet 3 of 5 5,374,663 F G. 5 OO 90 3O 2O O O 3OO 35O 4OO 45O 5OO 55O 6OO 65C 7OO WAVENUMBER (nm) F G. 6 OO 9O. 8O 7O 6O 5O 4O 3O 2O O O 3OO 35O 4OO 45O 5OO 55O 6OO 650 7OO WAVENUMBER (nm) U.S. Patent Dec. 20, 1994 Sheet 4 of 5 5,374,663 F G. 7 OO 90 4O 3O 2O O O 3OO 350 4OO 45O 5OO 55O 6OO 650 7OO WAVENUMBER (nm) F G. 8 IOO 90 5O EXAMPLE 8 4O 3O 2O O O 3OO 35C 4OO 45O 5OO 55O 6OO 65O 7OO WAVENUMBER (nm) U.S. Patent Dec. 20, 1994 Sheet 5 of 5 5,374,663 FIG. 9 OO 5O 4O 3O 2O O oL4N 3OO 35C 4OO 45O 5OO 55O 6OO 650 7OO WAVENUMBER (nm) FIG. IO OO 90 8O 7O 6O 5O 4O 3O 2O O O 3OO 350 4OO 45O 5OO 55O 6OO 650 7OO WAVENUMBER (nm) 5,374,663 1. 2 close to that originally possessed by human crystalline PROCESS FOR PRODUCING lenses. However, U.V. absorbers show a very low ab CYANOPSLA-CORRECTABLE INTRAOCULAR sorption in a visible light region and is unable to absorb LENS a visible blue light, though they can absorb an U.V. 5 light of 400 nm or less regarded to be a harmful wave This is a continuation of application Ser. No. length; therefore, with the U.V. absorber-containing 07/815,611, filed Jan. 7, 1992, now abandoned, which is intraocular lenses, the correction of cyanopsia is incom a continuation of 07/432,758, filed as PCT/- plete. When a large amount of an U.V. absorber is used JP89/00230, Mar. 3, 1989, now abandoned. in an intraocular lens in order to allow the lens to have TECHNICAL FIELD O an increased absorption in a visible light region, other properties of lens material are decreased or worsened in The present invention relates to a process for produc many cases, which is not preferable. ing a cyanopsia-correctable intraocular lens and partic Incidentally, a so-called prepolymer process is ularly to a process for producing an intraocular lens for known as a process for producing the U.V. absorber correction of the cyanopsia which arises in aphakic eye 15 containing intraocular lens mentioned above. In this patients after operation of cataract. prepolymer process, a monomer solution comprising a BACKGROUND ART monomer capable of forming a transparent lens material In recent years, with the increase in population of old upon polymerization, an U.V. absorber and a polymeri people, patients of senile cataract have increased. In 20 zation initiator is introduced into a reactor and then aphakic eye patients whose crystalline lens(es) has heated for a given length of time at a given temperature (have) been enucleated by operation of cataract, the to obtain a prepolymer of high viscosity; thereafter, the correction for eyesight is generally effected by the use prepolymer is filtered through a filter, casted into a cell of any of spectacles, contact lenses and intraocular constituted by, for example, two glass plates and a gas lenses. 25 ket, and then further heated for a given length of time at In effecting the above eyesight correction by specta a given temperature to obtain a transparent lens mate cles, the lenses for correction are thick convex lenses rial. having an unattractive appearance, and the image This prepolymer process has such advantages that formed on the retina is larger than that in normal eyes. the prepolyemr casted into the cell scarcely leaks out Accordingly, particularly when one eye is aphakic, 30 therefrom because of its high viscosity and that the there arises aniseikonia, thus making larger the fatigue shrinkage degree in the step of obtaining a transparent of optic nerve and cranial nerves and giving a big bur lens material from the prepolymer is small, enabling the den to the spectacles users. production of a transparent lens material having a de Hence, in recent years, there have been developed sired shape. On the other hand, the prepolymer process contact lenses which are superior in oxygen supply to 35 has problems such as (i) polymerization is effected in the cornea and which give a smaller burden to the cor two steps thereby making the operation complicated, nea even when worn for a long time, thus providing a (ii) the control of the polymerization degree and viscos very effective means for eyesight correction in aphakic ity of the prepolymer obtained in the first polymeriza eye patients. tion step is difficult; for example, when the polymeriza Further, there have been developed intraocular tion degree is high and resultantly the prepolyemr vis lenses which are implanted into eyes and accordingly cosity is high, the filtration treatment of the prepolymer require no detachment, and these lenses are gaining conducted before its casting into the cell is difficult (the acceptance in the market. The intraocular lenses, as filtration treatment of the prepolymer of high viscosity compared with the above mentioned spectacles, etc., is extremely difficult particularly when there is used, for have many advantages and are expected to further 45 spread in the future. example, a filter of 0.2 in pore diameter in order to Incidentally, many of the aphakic eye patients after remove not only dust but also bacteria), and (iii) when a cataract operation complain of glare, a difference of crosslinking monomer is used in order to allow the color vision, etc. In particular, cyanopsia in which ob polymer obtained to have a hardness, etc., an insoluble jects look bluish is known generally. Cyanopsia is a SO polymer is formed in the step of obtaining a prepolymer disease in which, owing to the removal of the crystal and the filtration treatment becomes difficult also in this line lens(es) originally having an yellow to yellowish case, and further an insoluble polyemr is formed even in brown color, a blue light (a complementary color to an the step of polymer production after the filtration treat yellow to yellowish brown color) reaches the retina ment and the polymer obtained (an intraocular lens without being weakened and consequently objects look 55 material) becomes non-uniform. more blue than in normal eyes. Even when artificial Hence, an object of the present invention is to pro intraocular lenses of conventional type have been im vide a process for producing a cyanopsia-correctable planted into eyes, a blue light reaches the retina without intraocular lens, which lens is able to eliminate the being weakened, in the case of eyes implanted with drawbacks of conventional intraocular lenses contain posterior chamber intraocular lenses made of poly ing an U.V.
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