Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Processes of preparing a desired or intentional composition...
Reexamination Certificate
2001-07-05
2003-05-06
Yoon, Tae H. (Department: 1714)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Processes of preparing a desired or intentional composition...
C523S108000, C526S243000, C526S244000, C526S245000, C526S270000, C524S544000, C351S16000R
Reexamination Certificate
active
06559198
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to novel formulation of monomers, to produce polymers for the purpose of manufacturing hydrophilic contact lenses and other optical devices, including optical medical devices. In particular, one important use of the materials made from the invention is the manufacture of corneal contact lenses.
2. Description of the Related Art
In recent years, hydrophilic corneal contact lenses have become more and more popular in the United States, Canada and throughout the world. In an attempt to create contact lenses which are comfortable and oxygen permeable and essentially clean from deposits it requires incorporation of a longer fluorocarbon chain component in order to make the surface of the lens slick, permitting easy movement on the eye without any friction, and wettable to accomplish necessary comfort for the patient.
Previous hydrophilic contact lenses are based on 2-hydroxyethyl methacrylate (HEMA) or derivatives thereof which produce reasonable comfort to the patient while they are clean; however, when worn for a longer period of time they have a tendency to accumulate deposits or debris on the surface of the lens and then require constant cleaning or in other cases become disposable, that patient has to dispose of contact lenses and get new ones.
While such materials accumulate proteinaceous matter as a deposit on the lens surface, the lens is impaired to proper transparency or if the deposits on the lens are too large, the lens could cause abrasion to the wearer's eyes.
SUMMARY OF THE INVENTION
The present invention, therefore is intended to improve performance of a hydrophilic contact lens on the human eyes. The copolymers of the present invention will give very good optical clarity when hydrated and also because they contain fluorocarbon chain monomer, which gives very good slick surface of the lens which remains free of debris or deposits, even when lenses are worn for longer periods of time. The copolymer plastic, when hydrated, will have increased strength over HEMA hydrophilic contact lenses. The copolymer plastic of the present invention can be prepared by polymerization in the rod form and then processed to the contact lens blanks and ultimately to the contact lenses, or can be directly cast molded in specific molds directly into the form of contact lenses.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
A still further facet of the invention includes synthesis of the copolymer plastic which, when hydrated in saline solution, gives water content between 25% to 60% which can be used for other medical devices, such as intra-ocular lenses, lenses for instruments used for body contact and health diagnostic instruments. The present invention includes the following monomers: [2-(N-Ethylperfluorooctanesulfonamido)methacrylate]
wherein R
1
and R
2
, which maybe the same or different, are hydrogen, alkyl, cyclic or phenyl groups, n is an integer from 1 to 5 and m is an integer from 0 to 10. Typical monomers are: 2-(N ethylperfluoroalkylsulfonamido)ethylmethacrylate, 2-(N ethylperfluoroalkylsulfonamido)ethylacrylate, or mixtures thereof.
Representative of the hydroxyalkyl monomer of acrylic or methacrylic acid are those having the following general formula:
wherein n is an integer from 1 to 5, and 2,3 dihydroxypropyl acrylate and 2,3 dihydroxyproply methacrylate or mixtures thereof. Representative of heteroatom hydrophilic monomer are those having the following general formula:
CH
2
═CH—(CH
2
)
4
NH
N-Vinyl 2-pyrrolidinone
An additional sulfone monomer can be incorporated into copolymeric plastic of the present invention. The preferable monomers are:
methyl vinyl sulfone,
methyl styrene sulfone,
ethyl vinyl sulfone,
ethyl styrene sulfone,
propyl vinyl sulfone,
propyl styrene sulfone,
phenyl vinyl sulfone,
phenyl styrene sulfone,
cyclohexyl vinyl sulfone,
cyclohexyl styrene sulfone,
pentyl vinyl sulfone,
pentyl styrene sulfone,
butyl vinyl sulfone,
butyl styrene sulfone,
phenoxyethyl vinyl sulfone,
phenoxyethyl styrene sulfone,
divinyl sulfone,
methacryloxyethyl methyl sulfone,
methacryloxyethyl ethyl sulfone,
methacryloxyethyl propyl sulfone,
methacryloxyethyl butyl sulfone,
methacryloxyethyl phenyl sulfone,
methacryloxyethyl pentyl sulfone,
methacryloxyethyl styrene sulfone,
or mixtures thereof.
The hydrophilic contact lens material can be further modified by the addition of methacrylic acid or acrylic acid and a small amount of cross-linking agent to improve overall performance of the contact lenses. Representative cross-linking agents are ethyleneglycol dimethacrylate, diethyleneglycol dimethacrylate, triethyleneglycol dimethacrylate, tetraethyleneglycol dimethacrylate, ethyleneglycol diacrylate, diethyleneglycol diacrylate, triethyleneglycol diacrylate, tetraethyleneglycol diacrylate, divinyl benzene, divinyl sulfone, trimethylolpropane trimethacrylate or mixtures thereof.
The preferred composition of the present invention comprises:
(a) from about 5 to 65 weight percent of ethylenically unsaturated fluorosulfonamidoethyl ester monomer of acrylic or methacrylic acid or mixtures thereof.
(b) from about 5 to 70 weight percent of ethylenically unsaturated hydroxyalkyl monomer of acrylic or methacrylic acid or mixtures thereof.
(c) from about 2 to 40 weight percent of N-Vinyl 2-pyrrolidinone.
(d) from about 0.1 to 8 weight percent of acrylic or methacrylic acid or mixtures thereof.
(e) from about 0.1 to 7 weight percent of cross-linking agent monomer (preferably ethyleneglycol dimethacrlate, diethyleneglycol dimethacrylate, triethyleneglycol dimethacrylate and tetraethyleneglycol dimethacryalte or mixtures thereof).
The polymerization of the oxygen permeable wettable contact lens material is disclosed in the prior art using free-radical polymerization techniques such as disclosed in Novicky U.S. Pat. No. 4,861,850.
REFERENCES:
patent: 4861850 (1989-08-01), Novicky
patent: 5079319 (1992-01-01), Mueller
patent: 5824719 (1998-10-01), Kunzler et al.
patent: 6107015 (2000-08-01), Anderson et al.
patent: 6245854 (2001-06-01), Obioha et al.
patent: 6380336 (2002-04-01), Soane et al.
Stevens Davis Miller & Mosher L.L.P.
Yoon Tae H.
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