CA2040419A1 - Soft gas permeable contact lens having improved clinical performance - Google Patents

Abstract

A hydrophilic soft gas permeable contact lens having substantially improved clinical performance by the provision of a sufficient higher proportion of hydroxy acrylic units to silicon units in the lens surface layer, as compared to that existing in the lens core, by the surface treatment of the lens, such as by reacting of the lens surface with polyols and base or acid or by radiation treatment of the base lens to graft, deposit or coat thereon hydroxy acrylic units.

Description

~vo ~91/1~428~ 1 2 0 ~ O ~ 1 9 P~/US90/0~032 SOFT GAS PERMEA~LE CONTACT LEMS
HAVING IMPROVED CLINI CAL PERFORMANCE

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BACKGROUND_OF THE INVENTION

This application is a continuation-in-part of prior applications, Serial Nos. 07/407,261, ~iled September 14, 1989;.07/132,174, filed December 14, 1987 (which in turn is a con~inuation-in-part of prior application Serial Mo.
OQ1,149, filed January 7, 1987); and 07/381,587, filed July 18, 1989.

The present invention relates to contact lenses, and more particularly to hydrophilic soft gas permeable contact lenses having improved clinical performance.
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Among the most important properties and require-ments of contact lenses axe substantial permeabili~y to oxygen (commonly referred to as DK ~, and a highly wettable : and deposition-resistan~ surface~
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The development and use of plastic materials and compositions for contact lenses has been the subject of much attention over the years.

Among the firs~ such developments was the so-called hard lens utilizing the hard plastic polymethylmethacry-late (P~MAI. However, this material does not exhibit a significant degree of oxygen permeability and has very poor surface wettability characteristicsO The art then progressed to soft lenses based upon poly 2-hydroxyethyl methacrylate (poly HEMA), a material having significantly better oxygen permeability and surface quality than the .. . , _ .. . . .

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WV 9l/042B3 ~ ' Pcr/us9o/oso32 hard PMMA plastic. Neverth~less, these characteristics were still not as high as desirable or necessary, and lenses of this type often resulted in serious problems of coxneal staining, swelling, ulcers, thickness and infection.

Somewhat more recently, based upon better under-standing of the corneal reguirement o~ substantial oxygen permeability, the art proposed the use of so-called hard gas permeable (HGP) lenses composed of either of two types o~ plastic materials, acrylic silicone or acrylic fluoro-silicone. See, e.g., U~S. Patent No. 3,~08,178. General-ly, the oxygen permeabili~y of H~P lenses can progressive-ly be increased with increasing amoun~s of the silicone and/or fluorosilicone in the- composition; at the sarne time, however, the surface wettability of the lens becomes progressively poorer. In order to overcome this problem, it is known to incorporate a relatively large amount of methacrylic acid (MAAi, an ionic material, into the formu-lation, resulting in the lens surface being negatively charged to a certain extent. While this expedient does lead to improved surface wettability, the negatively-charged surface has a very high absorptivity leading to serious deposition problems. As a conse~uence, the HGP
lens is of only limited potential.

Most recently, hydrophilic soft gas permeable (SGP) lenses have been developed based upon compositions contain ing, e.g., a polymeri~able vinylic siloxane monvmer and a hydrophilic vinylic monomer. See, eOg., U.S. Patent Nos .
4,136,250; 4,182,82~; 4,261,875; 4,343,927; 4,~26,389;
4,486,577; 4,605,712; 4,711,943 and 4,837,289. The SGP
lenses of this type, which generally have a water content of from about 25 ~o 75% by weight, have excellent oxysen permeability and hydrophilicity. Surprisingly, however, thé clinical performance of SGP lenses, includlng . . , : . . . . . . ............... . . . .

,. ~ -~09~283 2 0 ~ 0 41 9 PCT/VS90/0SD32 3~

functional (i.e., on the eye) wettability, deposition resistance, dehydration resistance and/or comfort, is very poor, making such lenses unsuitable for extended wear.
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Thus, notwithstanding the advances made to date, -there still exists a need for plastic contact lenses of the SGP type which not only possess a high degree of oxygen permeability, but also exhibit excellent clinical performance, such as functional wettability, deposition resistance, and com~ort, thus making the lenses suitable for extended wear. The foregoing is the principal object of the invention.

SUMMARY OF THE INVENTION

This and other objec~s are achieved in the present invention by the provision of a soft gas permeable contact lens, composed of the polymerization produet of composi-tions containing a polymerizable vinylic siloxane monomer and a hydrophilic vinylic monomer, having on the lens surface a proportion of hydroxy acrylic monomer units to silicon units sufficient to provide an SGP lens having the requisite high DK, softness and rebound elasticity, and which at the same time possess a high degree of clinical performance, thus rendering the lenses eminently suitable for long-term extended wear~

The requisite sufficient proportion of hydroxy acrylic monomer units to silicon units on the lens surface can be attained by surface treatment o the lens in order to increase hydroxy acrylic monomer units and~or to reduce the silicon units on the surface. In preferred e~bodi-ments of the invention, the surface treatment is carried out either by reaction on the lens surface with a polyhyd-ric alcohol (polyol) and/or base or acid, ox by radiation treatment of the lens to graft, deposit or coat hydroxy acrylic monomer uni'-s on L he sur~ac2 thereof.
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WO91/~2g3 I~ a~ P~T/US90/05032 It should be noted that the present invention differs signi~icantly from prior art practices related to the provision, or attemp~ed provision, of a hydrophilic surface on a hydrophobic lens. Thus, hydrophobic lenses are known in the art which are made of silicone rubber, a cross-l.inked polysiloxane, such as illustrated in U.S.
Patent No. 3,228,741. These hydrophobic lenses are highly oxygen p~rmeable but are extremely poor in functional wettability, deposition resistance and comfort, and also exhibit a mysterious tight lens syndrome. It is known in the art to seek to improve the functional wettability of such lenses by provision of an ultrathin coating of hydro-philic polymer~ See, e.g., U.S. Patent Nos. 3,854,g82;
3,916,033; 3,925,178; and 4,143,949. Generally these e~forts have not in any event proven successful. One reason is because the silicone rubber lens is rather rigid, and as a consequence an ultrathin (i.e., Angstoms level) hydrophilic coating is easily rubbed away during routine cleaning cycles, with the result that the lens soon re-exhibits the poor wettability, poor deposition resistance, discomfort and tight lens syndrome character-istic of sili~one rubber hydrophobic lenses. Provision of thicker layers of hydrophilic polymer on the lens to resist rubbing off is impractical, since oxygen permeabi-lity of the lens is substantially reduced and since the differences between the refractive index of the silicone rubber and the thick hydrophilic polymer coating become such as to xesult in a highly u~desirable lens.

In the present invention, the lens per se is a hydrophilic SGP lens containing a substantial amount of water (eOg., generally at least 25% by weisht) such that its surface, in contrast to the silicone rubber lenses, is already highly hydrophilic and no apparent need would exist to provide ~ hydrophilic polymeric surface coating thereon as is taught with respect to hydrophoblc lens .. . . . ..

~o,~/~2B3 2 ~ 4 ~ ~ 3 9 P~T/U~90/0~032 ma~erials. In the present invention, it has surprisingly been found that the SGP lenses, even though having highly hydrophilic surfaces, neverthèless can still be véry poor in clinical performance, and that this problem can be over~
come by providing on the surface of the SGP lens a ratio of hydroxy,acrylic units to silicon units which is suffi-cient to bring about significant clinical improvemént.

~ lso in contrast with the treatment of hydrophobic silicone rubber lenses, it is found that the criteria employed in improving wettability o those lenses by hydro-philic monomer coatings is not correlatable to bringing about improved clinical perormance in the hydrophilic SGP
lenses to which the present invention is directed. For example, for hydrophobic lenses, acceptable wettability has been determined based upon contact angle (see, e.g., Col. 7, lines 13-16, of U.S. Pa~ent No. 4,143,949~, result-ing in findings that coatinys based upon amide monomers (e.g., ~-vinylpyrrolidone) are quite effec~ive in improv-ing wettability ~see, e.g., E~ample 1-2 of the above patent). In contrast, however, in the context of the hydrophilic SGP lenses of the present invention and parti-cular those of preferred center thickness of from 0~05 to O.OB mm, such amide group-containiny monomers are quite ineffective in improving the clinical performance of the SGP lenses.

Accordingly, the findings and techni~ues of the present invention would not have been derivable or pre-dictable from the known practices regarding improving the wettability of hydrophobic silicone rubber lenses.

DETAILED DESCRIPTION OF THE INVENTION

The basic teachings and formulations and techniques, regarding formation of silicone-based SGP lenses are known . , - -- - - - - . , .
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Wo~1/04283 %~ i 9 -6- PCTtU~90/05~32 in the art, as reflected in the earlier-mentioned patents, the disclosures o~ which are!expxessly incorporated herein by reference. The SGP lens is formPd from the polymeriza-tion product of compositions containing at least one poly-merizable vinylic sîloxane IPVS) monomer, and at least one hydrophilic vinylic monomer. The polymerizable vinylic siloxane monomer contains at least one polymerizable vinylic group such as acrylic, styrenyl or vinylic group, at least one polysiloxanyl group, and at least one linkage connecting these two groups; thus, for example: ..

tris(trimethylsiloxy)silylpropyl-glycerol-ethyl methacrylate CH2=CCH3Coo(cH2~2oc~2cHoHcH2o(cHz)3si~os -CH3)3; and ~ -tris(trimethylsiloxy)silylpropyl methacrylate ~also sometimes referred tD hereinafter as TSM) CHz=CCH3COO(CH2) 3Si ( osi-c~3 ) 3 Hydrophilic vinylic monomers suitable for use in SGP lens compositions along with the PVS include, for example, N,N dimethylacrylamide (NNDMA), 2-hydroxyethyl methacrylate (HEMA), glyceryl methacrylate (GMA~, N-vinyl pyrrolidone and the likeO

The lenses Per se are formed by lathe cutting, cast molding, spin casting, or other like known techniques.

As earlier noted, SGP lenses made according to the known formulations possess a high oxygen permeability but exhibit poor clinical performance. In the present inven-tion, it has been discovered that by increase of the .. . . ....

~VO91/~83 P~T/US9~/05032 2t~0419 proportion of hydroxy acrylic monomer ~HAM) units, preEer-ably HEMA and/or G~A units, to silicon units at the lens sur~ace, the clinical performance can be substantially improved. As used herein, the units referred to are the structural monomeric units or the number of silicon atoms, including those as par~ o~ an overall copol~mer.ic structure.

Hydroxy acrylic monomer (HAM) suitable for the practice of this invention correspond to the formula H2C - C (: = O

wherein R is H or a substituted or unsubstituted alkyl, such as methyl or CH2COOH; and X is a radical selected ~rom the group consisting of hydroxyalkyloxy, hydroxy-alkyl amine, ~nd hydroxy; with the alkyl being substituted or unsubstituted, and preferably selected from Cl to C1O alkyls, most preferably C2 and C3 alkyls; and with the hydroxy on the alkyl being either a single hydroxy (e.g., as in 2-hydroxyethyl methacrylate) ox multiple hydroxy (e.g., as i~ glyceryl methacrylate ) .
Exemplary and preferred hydroxy acrylic monomers are:

1. 2-hydroxyethyl acxylate or methacrylate;

2. glyceryl acryla~e or methacrylate;

3. ethylene glycolato ethyl acrylate or methacry-late, i.e., CH2=CRCOO-CH2-CH2-O-CH2-CH2-OH

4. glycerolglyceryl acrylate or methacrylate, i.e., CH2=CRCOO-CH2C~(OH)-CH2-O~C~2-CH(OH)-CH2-OH

5. N-hydrox~methyl, N-methyl acrylamide or methacrylamide;

6. N-2-hydroxyethyl, N-methyl acrylamide or methacrylamide;

7. N-2,3-dihydroxypropyl, N-me~hyl acrylamide or - -methacrylamide;--8. acrylic acid, methacrylic acid or itaconic- -~-- - acid.~

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W~91/04~3 PC~/~S90/05032-As noted, the SGP lens of the invention is made from the known SGP lens compositions and, aftex lens formation, the lens is then treated to provide on its surface a pro-portion of H~ units to silicon units (e~g., by increase of HAM units and/or by decrease of silicon units) suffi-cient to provide improved clinical per~ormance o~ the lens,-such as functional wettability, deposition resist-ance, dehydration resistance and comfort.

One means ~or achieving the re~uisite surface proportion of HAM to silicon units is by reaction of the lens surface, preferably in the dehydrated state, with a pol yol of the formula Rl~OH)~ where Rl is a substituted or unsubstituted alkyl, preferably a C2 to C5 alkyl, and n is an integer of at least 2, such as glyceryl methacrylate, ethylene glycol, glycerine, glycerine-glycerine, polyglycerine, or the like. The reaction is preferably carried out in the presence of a base, such ~s sodium hydroxider preferably in a concentration of 0.1 to 10 mole percent based on the polyol, or an acid or acid-containing mixture, such as ethanol/sulfuric acid, the reaction beiny conducted to the extent that the physical properties of the base lens (e.gO, strength, oxygen permeability, softness, rebound elasticity, etc.) are essentially unaffected. This reaction is intended to increase the HAM units in the surface layer by transesterification and/or to reduce the silicon units by the cleavage of siloxane bonds catalyzed by base or acidO

Alternatively, the core lens can be treated with a HAM, preferably 2-hydroxye~hyl acrylate or methacrylate, by grafting, deposition or coating to the lens surface so as to provide a sufficient proportion of HAM units to silicon units at the lens surface. The grafting, deposi-tion or coating can be carried out using known radiation-induced reactions, including reactions induce~ by W , . .
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~ 4283 2 ~ ~ ~ 4 ~ 9 P~T/US9010S03~
_9_ x-ray, ~ -ray, and other electromagnetic radiation, such as xadio frequency, micrawave and the like, electron beam radiation, including eleotrical discharge, and the like, with reactions induced by UV, ~-ray. or electron beam radiation being preferred. The treating techni~ues per se that can be ùsed in the practice of this invention are well known in the art, such as the grafting, deposition or coating cured by W , ~-ray or electron beam, i~lustrated in U.S. Patent Nos. 3,916,033 and 3,854,982; coatin~ by spin casting or cast molding of the lenses cured by radia-tion; or plasma treating techniques, such as those dis-closed in U.S. Patent Nos. 3,925,1~8 and 4,143,949, as is well known in the art. The disclosures of these pxior art patents are expressly incorporated herein by referenceO
In the preferred embodiment of the invention, the surface treatment produces on the lens surface a thin coating consisting essentially of poly(hydroxy alkyl acrylate and/or methacrylate), more preferably poly~2-hydroxyethyl acrylate and/or methacrylate).

The re~uired sufficient proportion of HAM units to silicon units on the lens surface that produces the desir-able clinic~l performance will vary primarily depending upon the type and amount of particular PVS and hydrophilic monomer employed. However, the sufficient proportion in the surface layer will, at any proportion, be higher than that existing in the lens body or core. Preferably, the proportion of HAM units to silicon units in the surface layer is at least 0.5. Generall~, the higher the propor-tion the better the clinical perfonmance of the lens, and the thicker the treated surface layer the better the durability of the lens wettability. However, the treated layer can not be so thick that the desired properties of the lens are adversely affected. The extent of accep~able surface treatment can be monitored by high resolution photoelectron spectroscopy ~ESCAj or based on the clinical response as lllustrated ln the ~amples of this spec fic2-3, ~_~ ~n, tn~ ~iS~l~s~ ~`~ Ih' ~ ,; ~n~
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~. , ' .
~, WO91/04~g3 æ~ PCT/VS90/05032--the sufficient proportion of H~M units to silicon units on the lens surface can easily be determined by those skilled in the art.

Although not wishing to be bound by any theory as such, it is postulated that the improvément in the clini-cal perormance of ~he lens comes about, at least in part, by virtue of establishment of compatibility between the delicate corneal wetting mechanism of the eye and the composition and structure of the lens surface. The known SGP lens having insufficient proportion of HAM units to silicon units or containing too high a level of silicon units on the surface are too hydropho~ic for the spreading and binding of mucin to the lens surface. Mucin is the excellent wetting agent used in the cornea and contains a certain proportion of hydrophilic sites to hydrophobic sites. With increasing amount of HAM units on the lens surface, there are provided increased sites for hydrogen bonding with the hydrophilic sites on the mucin, while reduction of silicon surface units provides fewer hydro-phobic sites and thus better spreading of mucin on the lens surface. As a consequence of the preferred embodi-ment of the invention herein, which results in the lens surface having a sufficient proportion of HAM units to silicon units, the lens surface becomes more closely matched to, and receptive to, tear mucin. As a result, the mucin can better spread on and bind to the lens surface so as to provide the improved clinical perform-ance. Thus, when the wet~ing angle of the lens is controlled to that of the corneal surface free of mucin, the best results of this inven~ion may resul~.

The invention is further illustrated with reference to the following examples.

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~0 gltO4283 2 ~ ~ ~ 4 1 9 Pcr/US90,05~32 SGP lenses were fabricated from buttons which were made according to the formulations and procedures set forth in U.S. Patent No. 4,182,822, the starting formu-lation consisting of 36% (by weight), ~tris~trimethyl-siloxy) silylpropyl methacryla~e ~TSM) prepared according to Example 1 of the above patent, 59% N,N-dimethylacryl-amide ~NNDMA), and 5% methyl me~hacrylate (MMA) with 0.3%
~-~utylperoxypyvalate included as a catalyst. The formu-lation was placed in a Teflon tube. Aftex deoxygenation by nitrogen for 15 minutes, the tube was sealed and the formulation was polymerized in a 40C water bath for six houxs, followed by a 100C treatment for another six hours. ~he buttons cut fr~m the rods were post-cured a~
110C under high vacuum (0.5 Torr~ for six hours.

The lens can be made by the lathe technigue known in the art. The hydrated lenses were extracted and condition-ed in physiological saline solution for a time sufficient to insure no substantial irritation.

The lens thus made has high DK, about 4 to 5 times higher than that of the conventional poly HEMA soft lens, and contains abou~ 50% by weîght of water, and thu.s has softness, rebound elasticity and a highly hydrophilic lens surface. The proportion HAM units to silicon units on the lens surface is equal to zero. Clinically~ the lenses were very poor in performance such as functional wettabi-lity, deposition resistance and comfort, making the lens unsuitable for extended wear.

Provision of 6% by weight HEMA in the formulation, such that the formula~ion comprised 36% TSM, 58% NNDMA and 6% HEMA, results in a lens having high DK, softness, rebound elasticity, a highly. hydrophilic surface and a .
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WO~l/0~283 ,~ `9 -12- PCT/US90/0;032 proportion of HAM~to silicon units equal to 0.15, and thus an improved SGP lens having improved clinic 1 performance, such as functional wett~bility, deposition resistance and comfort as compared to the control lens above. Clinical-ly, the lenses could be worn for up to s~veral hours by test patients.

In the same manner, using 20% by wei~ht HEMA, such that the lens formulation contains 36% TSM, 44% NNDMA and 20% HEMA, results in a l~ns having high DK, so~tness, rebound elasticity, a highly hydrophilic surface and a proportion of HAM units to silicon uni~s e~ual to 0.5, and thus even more improved clinical performance, such as functional wettability, deposition resistance and comfort, as compared to the control lens. Clinically, the lenses could be worn continuously for up to several days by test patients, with wettability marginally u~acceptable in certain circumstances.

Further increase of the H~ to silicon proportion by increase of the amount of HEMA in the composition is at the expense of TSM, and thus reduces the oxygen permeabi-lity of the lens and/or causes the formation of opa~ue material. As shown in the follswing examples, further increase of the HAM to silicon proportion can be achieved by surface treatment.

EXAMPL~ 2 The lens containing 20% HEMA as made in Example 1, after being hydrated in physiological saline solution, is then extracted in isopropanol for 24 hours, followed by treatment in the dry state with glycerine (96% pllri~y, Colgate Palmolive Co~) containing 1 mole% NaOH at 70C for 30 minutes by stirring. The strength of the lens after the treatment was not significantly affected. The result-ing lens could be used for at least weekly extended wear ... . . . . ..

20~0~19 I/04~83 PCT/US~0/05032 by the test patients. The clinical of long texm wearing on one patient showed that the lenses could indeed con-tinuously be worn for up to 3 months for at least certain patients. - Thus, the- surface treatment resulted in sub-stantially improved clinical performance.
- . , `EXAMPLE 3 . : .
A SGP lens comprising 47~ IbY weight) TSM, 45% NNDMA
and 3% H~M~, having 38% water content, high DK, softness, highly hydrophilic lens surface and a proportion of HAM
units to silicon units equal to about 0.15, was found to be unsuitable ~or extended wear. Clinically, the lens produced poor vision, discomfort and en~ountered serious deposition problems within less than four hours of wear.
However, treatment of the same lens in dehydrated state by stirring the lens in a glycerine reagent (96% purity, Colgate Palmolive Co.) containins 10 mole% NaOH at 70C
for 2 hours converted the lens to one which on the same patient could be used for weekly exte~ded wear ~or a three week testing period with stable vision and no observable deposition, and demonstrated a liquid layer over the lens sur~ace.

According to an independent surface study (about 100 A surface layer) by photoelectron spectroscopy (ESCA) analysis of the lens after being treated as described in Example 3 showed that there was ~ reduction of about 18%
silicon or about 30% siloxy group and an increase of over-all carbon content from 62.5 to 65% in which the C in the CO group increased from 10.5 to 12.5% and the C in the COOR group increased from 5.3 to 6~3% after the txeatmen~.
The increase of CO and COOR content should indicate that the transesterification of glycerine occurs, i.e.,- the .

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W~91~04283 ' PCT/US90/~5032 formation of glyceryl methacrylate. The reduction of silicon units and/or the increase of glyceryl methacrylate units after the treatment increases the proportion of HAM
units ~o silicon units which provides the substantially improved clinical performance as described above. tNote:
ESCA data is the average value of the treated surface with 100 A depth. Thus, the value right at the surface is substantially higher than ~hose reported above.) EX~MPLE S

An unhydrated optically polished lens button was made according to U.S. Patent No. 4,182,822 employing 36%
(by weight) TSM, 42% NNDMA and 22% HEMA, and glycerine surface treated as set forth in Example 3 herein. The button was fully hydrated in physiological saline solu-tion, and its surface was subjected to a number o~
simulated cleaning cycles, each cycle involving thumb-rubbing 10 times in tap water, followed by wetting in physiological saline solution. The surface wettability to the physiological saline solution was substantially the same based on visual inspection after sixty (60) cleaning cycles, e~uivalent to about one years service life of the lens in weekly extended wear.

The surface of the untreated button was substan-tially not wettable by physiological saline solution under the same testing condition.

Although the invention has been described in connection with particular preferred embodiments, it is not intended to limit the invention to particulax forms set forth, but on the contrary, it is intended to cover such alternatives, modifications and equivalents as may be included within the spirit and scspe of the invention as defined by the appended claims~

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Claims (17)

WHAT IS CLAIMED IS:

1. A hydrophilic soft gas permeable contact lens having high oxygen permeability, softness and rebound elasticity, comprised of a polymerization product of a composition comprising a polymerizable vinylic siloxane monomer and a hydrophilic vinylic monomer, and containing in its surface layer a sufficiently higher proportion of hydroxy acrylic monomer units to silicone units than exists in the lens body so as to additionally provide a high degree of clinical performance to said contact lens.

2. A contact lens according to claim 1, wherein said sufficiently higher proportion results from treatment of the surface of said lens so as to provide in said surface layer a sufficient proportion of hydroxy acrylic monomer units to silicon units.

3. A contact lens according to claim 2, wherein said hydroxy acrylic is hydroxyalkyl acrylate and/or methacrylate.

4. A contact lens according to claim 3, wherein said treatment comprises reaction of the lens surface with a polyol of the formula R1(OH)n, where R1 is a substituted or unsubstituted alkyl, and n is an integer of at least 2.

5. A contact lens according to claim 4, wherein said polyol is selected from the group consisting of ethylene glycol, glycerine, and mixture thereof.

6. A contact lens according to claim 2, wherein said treatment comprises reacting onto said lens surface, by radiation-initiated reaction, hydroxy acrylic monomer.

7. A contact lens according to claim 6, wherein said hydroxy acrylic monomer is hydroxyalkyl acrylate and/or methacrylate.
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8. A contact lens according to claim 7, wherein said radiation is electromagnetic radiation.

9. A contact lens according to claim 7, wherein said radiation is ?-ray or UV.

10. A contact lens according to claim 7, wherein said radiation is selected from the group consisting of electron beam, electrical discharge and radio frequency.

11. A contact lens according to claim 7, wherein said polymerizable vinylic siloxane monomer is ?-tris(tri-methylsiloxy)silylpropyl methacrylate and wherein said hydrophilic vinylic monomer is N,N-dimethylacrylamide.

12. A contact lens according to claim 3, wherein said hydroxyalkyl acrylate and/or methacrylate is selected from the group consisting of 2-hydroxyethyl methacrylate and glyceryl methacrylate.

13. A contact lens according to claim 12, wherein said polymerizable vinylic siloxane monomer is ?-tris(tri-methylsiloxy)silylpropyl methacrylate and wherein said hydrophilic vinylic monomer is N,N-dimethylacrylamide.

14. A contact lens according to claim 7 wherein said treatment produces on said lens surface a thin coating consisting essentially of poly(hydroxy alkyl acrylate and/or methacrylate).

AMENDED CLAIMS
[received by the International Bureau on 19 March 1991 (19.03.91);
original claims 15-17 amended; other claims unchanged (1 page)]

15. A contact lens of claim 14, wherein said poly(hydroxy alkyl acrylate and/or methacrylate) is poly(2-hydroxyethyl acrylate and/or methacrylate).

16. A contact lens of claim 11, wherein said treatment produces on said lens surface a thin coating consisting essentially of poly (hydroxyalkyl acrylate and/or methacrylate).

17. A contact lens of claim 16, wherein said poly (hydroxy alkyl acrylate and/or methacrylate) is poly (2-hydroxyethyl acrylate and/or methacrylate).