Biomedical devices with hydrophilic coatings

Details Biomedical devices with hydrophilic coatings Biomedical devices with hydrophilic coatings

2000-02-07

2003-03-18

Cain, Edward J. (Department: 1714)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Processes of preparing a desired or intentional composition...

Reexamination Certificate

active

06534559

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to coated devices. In particular, the invention provides biomedical devices on the surfaces of which stable, hydrophilic, antimicrobial coatings are formed via coupling of the coating to the surface by ester or amide linkages.
BACKGROUND OF THE INVENTION
Devices for use in and on the human body are well known. The chemical composition of the surfaces of such devices plays a pivotal role in dictating the overall efficacy of the devices. For example, many devices, including catheters, stents, lenses, and implants require biologically non-fouling surfaces, meaning that proteins, lipids, and cells will not adhere to the surface. Lenses also must be wettable by tear fluid in order to ensure wearer comfort. Additionally, providing such devices with an antimicrobial surface is advantageous.
A wide variety of methods have been developed to coat device surfaces to provide them with desired characteristics. However, the need still exists for a simple, efficient process that will provide a stable, hydrophilic, antimicrobial coating.
DETAILED DESCRIPTION OF THE INVENTION AND PREFERRED EMBODIMENTS
The present invention provides a simple, economical process for producing devices with stable surface coatings, which coatings are both hydrophilic and antimicrobial. By “antimicrobial” is meant that bacterial adherence to the device surface is reduced in comparison to the uncoated surface, by about 30 percent or more.
In one embodiment, the invention provides a method for manufacturing biomedical devices comprising, consisting essentially of, and consisting of contacting at least one surface of a biomedical device with a coating effective amount of a carboxyl-functional polymer and a coupling effective amount of at least one coupling agent to produce a stable, hydrophilic and antimicrobial coating on the surface. In another embodiment the invention provides biomedical devices comprising, consisting essentially of, and consisting of a biomedical device at least one surface of the device having a carboxyl functional polymer coating coupled thereto by at least one coupling agent.
By “biomedical device” is meant any device designed to be used while in or on either or both human tissue or fluid. Examples of such devices include, without limitation, stents, implants, catheters, and ophthalmic lenses. In a preferred embodiment, the biomedical device is an ophthalmic lens including, without limitation, contact or intraocular lenses. More preferably, the device is a contact lens.
It is an unexpected discovery of the invention that carboxyl functional polymers may be used to provide a stable, antimicrobial as well as hydrophilic coating for biomedical devices. By “stable” is meant that subjecting the coating to autoclaving, washing with a cleaning agent, and/or rinsing with a saline solution does not substantially alter the chemical properties of the coating. The coatings of the invention may be coupled to the device surface via ester linkages, amide linkages, or a combination thereof using certain coupling agents.
Coupling agents useful in the invention include, without limitation, carbodiimides, N, N′-carbonyldiimidazole, phosphoryl chloride, titanium tetrachloride, sulfuryl chloride fluoride, chlorosulfonyl isocyanate, phosphorus iodide, pyridinium salts of tributyl amine, phenyl dichlorophosphate, polyphosphate ester, chlorosilanes, and the like as well as mixtures of tributyl phosphorus and phenyl isocyanate, alkyl chloroformates and triethyl amine, 2-chloro-1,3,5-trinitrobenzene and pyridine, methyl sulfuryl chloride and diethyl amine, and triphenylphosphine, carbon tetrachloride and triethyl amine. Preferred coupling agents are carbodiimides. More preferred are 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide and dicyclohexyl carbodiimide.
Although any number of polymers, such as those containing primary or secondary amino groups, hydroxyl groups, carboxyl groups, or mixtures thereof, may be useful in providing a hydrophilic coating, it has been discovered that the use of a carboxyl functional hydrophilic polymer, preferably poly(acrylic acid), provides a coating that is superior in hydrophilicity when compared to other such coatings. Further, these coatings provide the additional advantage of being antimicrobial.
Examples of suitable carboxyl functional hydrophilic polymers include, without limitation, poly(acrylic acid), poly(methacrylic acid), poly(maleic acid), poly(itaconic acid), block or random copolymers of (meth)acrylic acid, acrylic acid, maleic acid, itaconic acid with any reactive vinyl monomer, and the like, and mixtures thereof Preferably, the carboxyl functional hydrophilic polymer is poly(acrylic acid) or poly(methacrylic acid). More preferably, poly(acrylic acid) is used.
The carboxyl functional polymers may be of any molecular weight. Preferably, the polymers are of a relatively high molecular weight, or about 10,0000 to 10,000,000, more preferably about 100,000 to about 4,000,000 g/mole, most preferably about 100,000 to about 1,000,000 g/mole.
One or more surfaces of a device may be coated using the process of the invention. Suitable surfaces for use in the invention are any surfaces with hydroxyl groups, amino groups, or mixtures thereof Preferably, the surface is made of a silicone elastomer, hydrogel, or silicone-containing hydrogel. More preferably, the surface is a siloxane including, without limitation, polydimethyl siloxane macromers, methacryloxypropyl polyalkyl siloxanes, and mixtures thereof, silicone hydrogel or a hydrogel, such as ETAFILCON™.
In the processes and devices of the invention, if the surface material to be coated does not contain the requisite functional group, such groups may be incorporated into the surface material. For example, hydroxyl groups may be incorporated by addition of one or more hydroxyl-containing monomers into the polymers used to form the surface. Examples of such hydroxyl containing monomers include, without limitation, mono(meth)acrylates of ethylene glycol, propylene glycol, glycerol, tetraethylene glycol, and the like. Amino groups may be incorporated using, without limitation, (meth)acrylates of aminoalcohols such as aminoethanol, tert-butylaminoethanol, or (meth)acrylamides of diamines such as bisaminopropane.
Alternatively, amine or hydroxyl functional, silicone-containing monomers or macromers may be used to incorporate the hydroxyl or amino functionalities into the surface. Suitable hydroxyl containing macromers include, without limitation, silicone containing linear or branched hydroxyalkylaniine functional monomers of the structure:
wherein: n is 0 to 500, m is 0 to 500, and n+m=10 to 500, preferably 20 to 250; R
2
, R
4
, R
5
, R
6
, and R
7
are each independently a substituted or, preferably, unsubstituted monovalent alkyl of 1 to 10 carbon atoms or a substituted or, preferably, unsubstituted aryl group, suitable substituents for which include alcohol, ester, amine, ketone, carboxylic acid, or ether groups; R
1
, R
3
, and R
8
are each independently a substituted or, preferably unsubstituted monovalent alkyl of 1 to 30 carbon atoms or a substituted or, preferably, unsubstituted aryl group suitable substituents for which are alcohol, ester, amine, ketone, carboxylic acid, or ether groups, and at least one of R
1
, R
3
, and R
8
is of the formula:
wherein R
9
is any group capable of linking N to Si, including without limitation, a linear or branched divalent alkyl of 1 to about 10 carbon atoms or an ether group, R
10
and R
11
are each independently H, a substituted or unsubstituted monovalent alkyl of 1 to 5 carbon atoms, a substituted or unsubstituted aryl group, suitable substituents for which are substituted with alcohol, ester, amine, ketone, carboxylic acid, or ether groups, or the structure:
wherein R
14
is H or a monovalent (meth)acryloyl, styryl, vinyl, allyl, or N-vinyl lactam polymerizable group and preferably H or methacryloyl; R
16
is H, a monovalent substituted or unsubstituted alkyl group of 1 to 6 carbon atoms, a substituted or unsubstitute

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