End-capped polymers and compositions containing such compounds

• US 7,241,813 B2
• Filed: 12/20/2002
• Issued: 07/10/2007
• Est. Priority Date: 12/21/2001
• Status: Active Grant

• Current Assignee: Isotis Orthobiologics, Inc. (Orthofix Medical Inc.)
• Original Assignee: Isotis Orthobiologics, Inc. (Orthofix Medical Inc.)
• Inventors: Kay, John F., Eisch, John J.
• Primary Examiner(s): Woodward; Michael P.
• Assistant Examiner(s): Silverman; Eric E.
• Application Number:
  US10/326,339
• Publication Number:
  US 20030175322A1
• Time in Patent Office: 1,663 Days
• Field of Search: None
• US Class Current: 514/772.1
• CPC Class Codes: C08G 2650/04 End-capping
• CPC Class Codes: C08G 2650/58 Ethylene oxide or propylene oxide copolymers, e.g. pluronics
• CPC Class Codes: C08G 65/32 Polymers modified by chemical after-treatment
• CPC Class Codes: C08G 65/322 containing hydrogen
• CPC Class Codes: C08G 65/323 containing halogens
• CPC Class Codes: C08G 65/328 containing other elements
• CPC Class Codes: C08G 65/337 containing other elements organic compounds containing halogens only as halides of a carboxyl group C08G65/332

Abstract

End-capped polymers, methods for making those end-capped polymers and compositions containing those end-capped polymers are disclosed. One of the disclosed end-capped copolymers has the formula:

and may be combined with demineralized bone particles to form a tissue repair composition.

Claims

1. A polyoxyethylene-polyoxypropylene-polyoxyethylene triblock copolymer wherein both terminal hydroxyl groups in the triblock copolymer have been replaced with terminal methoxy groups and wherein the polyoxyethylene-polyoxypropylene-polyoxyethylene triblock copolymer

is derived from a dilithium salt of a dihydroxy starting material, and wherein both of the terminal hydroxyl groups have been replaced with terminal methoxy groups as a result of chemical modification.

2. The compound of claim 1, wherein the degree of polymerization of both polyoxyethylene blocks is about 101 and the degree of polymerization of the polyoxypropylene block is about 56.

3. A method of making polyoxyethylene-polyoxypropylene-polyoxyethylene triblock copolymer wherein both terminal hydroxyl groups in the triblock copolymer have been replaced with terminal methoxy groups and wherein the polyoxyethylene-polyoxypropylene-polyoxyethylene triblock copolymer has no hydroxyl groups comprising:

(a) providing a polyoxyethylene-polyoxypropylene-polyoxyethylene triblock copolymer with two terminal hydroxyl groups

(b) contacting the polyoxyethylene-polyoxypropylene-polyoxyethylene triblock copolymer defined in step (a) with butyllithium or lithium aluminum hydride to form a dilithium salt and

(c) contacting the product of step (b) with methyl iodide, resulting in complete conversion of all hydroxyl groups in the polyoxyethylene-polyoxypropylene-polyoxyethylene triblock copolymer of step (a) into methyl ethers.

4. The method of claim 3, wherein the degree of polymerization of both polyoxyethylene blocks is about 101 and the degree of polymerization of the polyoxypropylene block is about 56.

5. A composition comprising:

(i) demineralized bone particles, and

(ii) a polyoxyethylene-polyoxypropylene-polyoxyethylene triblock copolymer wherein both terminal hydroxyl groups in the triblock copolymer have been replaced with terminal methoxy groups and wherein the polyoxyethylene-polyoxypropylene-polyoxyethylene triblock copolymer wherein the polyoxyethylene-polyoxypropylene-polyoxyethylene triblock copolymer

derived from a dilithium salt of a dihydroxy starting material and wherein all of the dihydroxy starting material is completely etherified as a result of chemical modification.

6. The composition according to claim 5, wherein the polyoxyethylene-polyoxypropylene-polyoxyethylene triblock copolymer defined in part (ii) is dispersed in water.

7. The composition according to claim 6, wherein the dispersion of the polyoxyethylene-polyoxypropylene-polyoxyethylene triblock copolymer defined in part (ii) in water exhibits reverse phase behavior.

8. The composition according to claim 5, wherein the composition is a tissue repair composition.

9. The composition according to claim 5, wherein the composition further comprises collagen, gelatin, BMIPs, bone mineral, hydroxyapatite, tricalcium phosphate, biphasic calcium phosphate, calcium sulfate, biological glasses, a natural polymer or a synthetic polymers.