# US 6,723,815 B2 · Covalently-bound, hydrophilic coating compositions for surgical implants

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- Number: US 6,723,815 B2
- Document ID: US6723815B2
- Status: Granted
- Kind: B2
- Application number: 10/437,325
- Filed: 2003-05-13
- Published: 2003-11-06
- Granted: 2004-04-20
- Earliest claimed: 1999-09-02
- Assignees: Alcon Inc.
- Inventors: Thomas A. Callaghan; Albert R. Leboeuf
- Web page: https://patentgrep.com/patent/US6723815B2

## CPC

- A61L 27/34: Macromolecular materials
- A61L: METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K)

## Abstract

Covalently-bound, hydrophilic copolymer coatings for implants are disclosed. The copolymer coatings comprise a hydrophobic aryl acrylic monomer, a hydrophilic monomer selected from the group consisting of hydroxyalkyl (meth)acrylates, n-vinyl pyrrolidone and acrylamides, and a reactive plasticizer.

## Claims

### Claim 1

A copolymeric coating composition for a surgical implant wherein the coating composition is capable of absorbing from at least 5 to about 90% water and comprises
(i) a hydrophobic aryl acrylic monomer of the formula
wherein:
A is H, CH3, CH2CH3, or CH2OH;
B is (CH2)m or [O(CH2)2]n;
C is (CH2)w;
m is 2-6;
n is 1-10;
Y is nothing, O, S, or NR, provided that if Y is O, S, or NR, then B is (CH2)m;
R is H, CH3, CnH2n+1(n=1-10), iso-OC3H7, C6H5, or CH2C6H5;
w is 0-6, provided that m+w≦8; and
D is H, C1-C4 alkyl, C1-C4 alkoxy, C6H5, CH2C6H5 or halogen;
(ii) a hydrophilic monomer selected from the group consisting of hydroxyalkyl (meth)acrylates; n-vinyl pyrrolidone and acrylamides;
(iii) a reactive plasticizer selected from the group consisting of polyethylene glycol (200-2000) mono(meth)acrylates and polyethylene glycol (200-2000) monomethylether mono(meth)acrylates; and
(iv) a covalent cross-linking agent.

### Claim 2 (depends on 1)

The coating composition of claim 1 wherein the hydrophilic monomer is selected from the group consisting of hydroxyalkyl (meth)acrylates and n-vinyl pyrrolidone.

### Claim 3 (depends on 2)

The coating composition of claim 2 wherein the coating composition comprises a hydroxyalkyl (meth)acrylate and n-vinyl pyrrolidone.

### Claim 4 (depends on 1)

The coating composition of claim 1 wherein the hydrophilic monomer is selected from the group consisting of methacrylamide; ethacrylamide; propacrylamide; dimethyl (meth)acrylamide; diethyl (meth)acrylamide and dipropyl (meth)acrylamide.

### Claim 5 (depends on 1)

The coating composition of claim 1 wherein the coating composition is capable of absorbing from about 30 to about 80% water.

### Claim 6 (depends on 1)

The coating composition of claim 1 wherein the coating composition is capable of absorbing from about 40 to about 60% water.

### Claim 7 (depends on 1)

The coating composition of claim 1 wherein A is CH3, B is (CH2)m, m is 2-5, Y is nothing or O, w is 0-1, and D is H.

### Claim 8 (depends on 1)

The coating composition of claim 1 wherein the hydrophobic aryl acrylic monomer is selected from the group consisting of 2-phenylethyl methacrylate; 3-phenylpropyl methacrylate; 4-phenylbutyl methacrylate; 5-phenylpentyl methacrylate; 2-benzyloxyethyl methacrylate; and 3-benzyloxypropyl methacrylate.

### Claim 9 (depends on 1)

The coating composition of claim 1 wherein the coating composition comprises from about 10-60% of 2-phenylethyl (meth)acrylate, from about 5-70% of hydrophilic monomer and from about 20-40% of reactive plasticizer.

### Claim 10 (depends on 1)

The coating composition of claim 1 wherein the composition comprises from about 20-50% of 2-phenylethyl methacrylate, from about 5-20% of a mixture of 1,3- and 2,3-dihydroxypropyl methacrylate, from about 0-40% of n-vinyl pyrrolidone, and from 20-40% of polyethylene glycol (400) monomethylether monomethacrylate.

### Claim 11 (depends on 1)

The coating composition of claim 1 wherein the cross-linking agent is selected from the group consisting of blocked isocyanates and peroxides.

### Claim 12 (depends on 11)

The coating composition of claim 11 wherein the cross-linking agent is selected from the group consisting of imidazole blocked isocyanatoethyl methacrylate; di-imidazole blocked 1,12-isocyanatododecane; benzoyl peroxide; and 2,4-dichlorobenzoyl peroxide.

### Claim 13 (depends on 1)

The coating composition of claim 1 wherein the coating composition further comprises one or more ingredients selected from the group consisting of UV absorbers that are copolymerizable with the hydrophobic aryl acrylic monomer and hydrophilic monomer; blue-light blocking colorants that are copolymerizable with the hydrophobic aryl acrylic monomer and hydrophilic monomer; and chain transfer agents.

### Claim 14 (depends on 1)

The coating composition of claim 1 wherein the reactive plasticizer is polyethylene glycol (400) monomethylether monomethacrylate.

### Claim 15 (depends on 13)

The coating composition of claim 13 wherein the coating composition comprises a chain transfer agent selected from the group consisting of 1-dodecanethiol and 2-mercaptoethanol.

### Claim 16

A coated surgical implant comprising a coating and a substrate wherein the coating and the substrate are not identical, the coating is attached to the substrate by covalent bonds, the coating is from about 0.01 to about 1 μm thick, and the coating comprises a covalently cross-linked copolymer comprising
(i) a hydrophobic aryl acrylic monomer of the formula
wherein:
A is H, CH3, CH2CH3, or CH2OH;
B is (CH2)m or [O(CH2)2]n;
C is (CH2)w;
m is 2-6;
n is 1-10;
Y is nothing, O, S, or NR, provided that if Y is O, S, or NR, then B is (CH2)m;
R is H, CH3, CnH2n+1(n=1-10), iso-OC3H7, C6H5, or CH2C6H5;
w is 0-6, provided that m+w≦8; and
D is H, C1-C4 alkyl, C1-C4 alkoxy, C6H5, CH2C6H5 or halogen;
(ii) a hydrophilic monomer selected from the group consisting of hydroxyalkyl (meth)acrylates; n-vinyl pyrrolidone and acrylamides;
(iii) a reactive plasticizer selected from the group consisting of polyethylene glycol (200-2000) mono(meth)acrylates and polyethylene glycol (200-2000) monomethylether mono(meth)acrylates;
and a covalent cross-linking agent, and wherein the covalently cross-linked copolymer is capable of absorbing from at least 5 to about 90% water.

### Claim 17 (depends on 16)

The coated surgical implant of claim 16 wherein the substrate comprises a hydrophobic acrylic material.

### Claim 18 (depends on 16)

The coated surgical implant of claim 16 wherein the covalently cross-linked copolymer comprises a hydrophilic monomer selected from the group consisting of hydroxyalkyl (meth)acrylates and n-vinyl pyrrolidone.

### Claim 19 (depends on 17)

The coated surgical implant of claim 17 wherein the covalently cross-linked copolymer comprises a hydroxyalkyl (meth)acrylate and n-vinyl pyrrolidone.

### Claim 20 (depends on 16)

The coated surgical implant of claim 16 wherein the covalently cross-linked copolymer is capable of absorbing from about 30 to about 80% water.

### Claim 21 (depends on 16)

The coated surgical implant of claim 16 wherein the covalently cross-linked copolymer comprises from about 10-60% of the hydrophobic aryl acrylic monomer, from about 5-70% of hydrophilic monomer and from about 20-40% of reactive plasticizer.

### Claim 22 (depends on 16)

The coated surgical implant of claim 16 wherein the implant is selected from the group consisting of intraocular lenses and contact lenses.

### Claim 23

A method of applying a coating to a surgical implant comprising the steps of:
a) preparing an uncross-linked copolymer comprising (i)
wherein:
A is H, CH3, CH2CH3, or CH2OH;
B is (CH2)m or [O(CH2)2]n;
C is (CH2)w;
m is 2-6;
n is 1-10;
Y is nothing, O, S, or NR, provided that if Y is O, S, or NR, then B is (CH2)m;
R is H, CH3, CnH2n+1(n=1-10), iso-OC3H7, C6H5, or CH2C6H5;
w is 0-6, provided that m+w≦8; and
D is H, C1-C4 alkyl, C1-C4 alkoxy, C6H5, CH2C6H5 or halogen;
(ii) a hydrophilic monomer selected from the group consisting of hydroxyalkyl (meth)acrylates; n-vinyl pyrrolidone; and acrylamides; and (iii) a reactive plasticizer selected from the group consisting of polyethylene glycol (200-2000) mono(meth)acrylates and polyethylene glycol (200-2000) monomethylether mono(meth)acrylates, and optionally (iv) a latent covalent cross-linking agent, such that the copolymer is capable of absorbing from at least 5 to about 90% water;
b) forming a coating solution by dissolving the copolymer in an organic solvent and if the copolymer does not contain a latent cross-linking agent then adding covalent a cross-linking agent to the solution;
c) applying the coating solution to the implant; and
d) drying the coating solution on the implant, such that the latent cross-linking agent or covalent cross-linking agent is activated and the copolymer is covalently bound to the implant.