Reactive compounding of hydrogels

• US 7,947,784 B2
• Filed: 11/16/2007
• Issued: 05/24/2011
• Est. Priority Date: 11/16/2007
• Status: Expired due to Fees

• Current Assignee: Zimmer Incorporated (Zimmer Biomet Holdings, Inc.)
• Original Assignee: Zimmer Incorporated (Zimmer Biomet Holdings, Inc.)
• Inventors: Charlebois, Steven, Yakimicki, Donald L., Thomas, Brian H.
• Primary Examiner(s): Jagannathan; Vasu
• Assistant Examiner(s): Kaucher; Mark S
• Application Number:
  US11/941,478
• Publication Number:
  US 20090131590A1
• Time in Patent Office: 1,285 Days
• Field of Search: 525/57, 525/61, 525/386, 524/916
• US Class Current: 525/386
• CPC Class Codes: C08F 116/06 Polyvinyl alcohol ; Vinyl alcohol
• CPC Class Codes: C08F 8/00 Chemical modification by after-treatment graft polymers, block polymers, crosslinking with unsaturated monomers or with polymers C08F251/00 - C08F299/00; of conjugated diene rubbers C08C
• CPC Class Codes: C08F 8/30 Introducing nitrogen atoms or nitrogen-containing groups
• CPC Class Codes: C08J 3/075 Macromolecular gels
• CPC Class Codes: C08J 3/24 Crosslinking, e.g. vulcanising, of macromolecules mechanical aspects B29C35/00; crosslinking agents C08K
• CPC Class Codes: Y10S 524/916 Hydrogel compositions

Abstract

This invention provides methods to form modified hydrogel materials using reactive compounding. The method includes mixing a hydrogel material with a plasticizer in a compounding apparatus. During mixing, a reactive chemical compound is added to the mixture that reacts with the hydrogel material to form a modified hydrogel material.

Claims

1. A method of forming a modified hydrogel material by reactive compounding, comprising:

mixing a hydrogel material in an extrusion reactor at a temperature of about 70°

C. to about 400°

C.; and

during mixing, adding to the extrusion reactor a reactive chemical compound selected from the group consisting of carboxyl-terminated poly-N-vinylpyrrolidone, carboxyl-terminated poly-2-vinyl pyridine, carboxyl-terminated poly-N-vinyl imidazole, and alpha-methoxy-omega-succinic acid terminated polyethylene glycol, and combinations thereof to react with the hydrogel material to form a modified hydrogel material, and wherein the modified hydrogel material has a polymer concentration of greater than about 30% w/v.

2. The method of claim 1 wherein the hydrogel material comprises at least one polymer that is a hydrophilic polymer.

3. The method of claim 2 wherein the hydrophilic polymer is polyvinyl alcohol, polyvinyl pyrillodone, poly(ethylene-co-vinyl alcohol), or polyacrylamide, or a derivative thereof.

4. The method of claim 1 further comprising adding a solvent to the mixed hydrogel material and the reactive chemical compound wherein the solvent is selected from the group consisting of dimethyl sulfoxide, tetrahydrofurane, methylene chloride, ether, toluene, and dimethylforamide, and combinations thereof.

5. The method of claim 1 wherein the extrusion reactor is a twin screw extruder.

6. The method of claim 5 further comprising the step of pelletizing the modified hydrogel material as it is extruded from the twin screw extruder.

7. The method of claim 6 wherein the pelletized, modified hydrogel material is formed at a rate of at least about 2 kg/hr.

8. A method of forming a modified hydrogel material by reactive compounding, comprising:

mixing a hydrogel material comprising polyvinyl alcohol or a derivative thereof in an extrusion reactor at a temperature of about 70°

C. to about 400°

C.;

during mixing, adding to the extrusion reactor a reactive chemical compound selected from the group consisting of carboxyl-terminated poly-N-vinylpyrrolidone, carboxyl-terminated poly-2-vinyl pyridine, carboxyl-terminated poly-N-vinyl imidazole, and alpha-methoxy-omega-succinic acid terminated polyethylene glycol, and combinations thereof to react with the hydrogel material to form a modified hydrogel material having a polyvinyl alcohol concentration of greater than about 30% w/v; and

extruding the modified hydrogel material from the extrusion reactor and pelletizing the modified hydrogel material as it is extruded from the extrusion reactor.

9. The method of claim 8 wherein the extruding and pelletizing are carried out at a rate of at least about 2 kg/hr.

10. A method comprising:

mixing a hydrogel material in an extrusion reactor; and

during mixing, adding to the extrusion reactor a reactive chemical compound during continuous melt extrusion in the extrusion reactor at a temperature of about 70°

C. to about 400°

C., the reactive chemical compound selected from the group consisting of carboxyl-terminated poly-N-vinylpyrrolidone, carboxyl-terminated poly-2-vinyl pyridine, carboxyl-terminated poly-N-vinyl imidazole, and alpha-methoxy-omega-succinic acid terminated polyethylene glycol, and combinations thereof to react with the hydrogel material to form a modified hydrogel material, and wherein the modified hydrogel material has a polymer concentration of greater than about 30% w/v;

extruding the modified hydrogel material from the extrusion reactor;

pelletizing the extruded, modified hydrogel material; and

post-molding the pelletized, modified hydrogel material.

11. The method of claim 10, further comprising selecting the hydrogel material to be polyvinyl alcohol.

12. The method of claim 10, further comprising selecting the reactive chemical compound to be carboxyl-terminated poly-2-vinyl pyridine.

13. The method of claim 10, further comprising selecting the reactive chemical compound to be alpha-methoxy-omega-succinic acid terminated polyethylene glycol.

14. The method of claim 10, further comprising selecting the reactive chemical compound to be carboxyl-terminated poly-N-vinyl imidazole.