Covalently-bound, hydrophilic coating compositions for surgical implants
AssigneeAlcon Inc.
InventorsThomas A. Callaghan, Albert R. Leboeuf
Life of this patent
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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.
Claims23
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.
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.
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.
Dependencies are inferred from the claim text.