Methods for manufacturing copolymers having 1-methyl-2-methoxyethyl moieties and use of same

• US 8,063,151 B2
• Filed: 11/19/2007
• Issued: 11/22/2011
• Est. Priority Date: 11/21/2006
• Status: Active Grant

• Current Assignee: Abbott Laboratories Incorporated
• Original Assignee: Abbott Laboratories Incorporated
• Inventors: Pacetti, Stephen
• Primary Examiner(s): Jagannathan; Vasu
• Assistant Examiner(s): PAK, HANNAH J
• Application Number:
  US11/942,707
• Publication Number:
  US 20080146696A1
• Time in Patent Office: 1,464 Days
• Field of Search: 523/113, 526/319, 526/320, 526/329, 526/329.6, 526/329.7, 526/328.5, 526/330, 525/330.1, 525/330.6, 525/384, 525/385
• US Class Current: 525/330.1
• CPC Class Codes: A61L 2300/00 Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
• CPC Class Codes: A61L 27/34 Macromolecular materials
• CPC Class Codes: A61L 27/54 Biologically active materials, e.g. therapeutic substances A61L27/227 takes precedence
• CPC Class Codes: A61L 29/085 Macromolecular materials
• CPC Class Codes: A61L 29/16 Biologically active materials, e.g. therapeutic substances A61L29/048 takes precedence
• CPC Class Codes: A61L 31/10 Macromolecular materials
• CPC Class Codes: A61L 31/16 Biologically active materials, e.g. therapeutic substances A61L31/047 takes precedence
• CPC Class Codes: A61P 29/00 Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: A61P 37/08 Antiallergic agents antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14
• CPC Class Codes: A61P 7/02 Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
• CPC Class Codes: C08L 27/18 Homopolymers or copolymers or tetrafluoroethene

Abstract

The copolymers include a hydrophobic monomer and an acryloyl or methacryloyl ester of a propylene glycol monomethyl ether, also referred to as 1-methyl-2-methoxyethyl acrylate (“MMOEA”). The combination of the hydrophobic monomer and the MMOEA monomer advantageously provides desired mechanical strength, biocompatibility, and drug permeability in the copolymers. The copolymers can advantageously be used on medical devices.

Claims

1. A method for manufacturing a biocompatible copolymer, comprising:

polymerizing a plurality of acrylate monomers to yield a copolymer having the following formula,

2. A method as in claim 1, in which the copolymer is formed by reacting a hydrophobic monomer with a 1-methyl-2-methoxyethyl acrylate monomer.

3. A method as in claim 1, in which the R₁ group is coupled to an acrylate monomer of the intermediate polymer.

4. A method as in claim 3, in which the coupling of the R₁ group to the intermediate polymer is carried out by a transesterification process in which an ester bond is formed between a hydrophobic compound and an acrylate monomer of the intermediate polymer.

5. A method as in claim 1, in which the 1-methoxy-2-methoxyethyl group is coupled to an acrylate monomer of the intermediate polymer.

6. A method as in claim 5, in which the coupling of the 1-methyl-2-methoxyethyl group to the intermediate polymer is carried out by a transesterification process in which an ester bond is formed between a 1-methoxy-2-propanol and an acrylate monomer of the intermediate polymer.

7. A method as in claim 1, in which R₁ is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, 2-ethyl-hexyl, n-hexyl, cyclohexyl, n-hexyl, isobornyl, trimethylcyclohexyl and combination thereof.

8. A method as in claim 1, further comprising forming the 1-methyl-2-methoxyethyl acrylate monomer by reacting a polymerizable compound with 1-methoxy-2-propanol to yield the 1-methyl-2-methoxyethyl acrylate monomer.

9. A method as in claim 2, in which the concentration of the hydrophobic monomer and the concentration of the 1-methyl-2-methoxyethyl acrylate monomer are selected to yield a thermoplastic polymer with a hydrated glass transition temperature in a range from about −

30°

C. to about 37°

C.

10. A method as in claim 2, in which the concentration of the hydrophobic monomer and the concentration of the 1-methyl-2-methoxyethyl acrylate monomer are selected to yield a thermoplastic polymer with a hydrated glass transition temperature in a range from about 0°

C. to about 37°

C.

11. A method as in claim 2, in which the concentration of the hydrophobic monomer and the concentration of the 1-methyl-2-methoxyethyl acrylate monomer are selected to yield a thermoplastic polymer with a dry glass transition temperature in a range from about −

30°

C. to about 100°

C.

12. A method as in claim 2, in which the concentration of the hydrophobic monomer and the concentration of the 1-methyl-2-methoxyethyl acrylate monomer are selected to yield a thermoplastic polymer with a dry glass transition temperature in a range from about 0°

C. to about 70°

C.

13. A method as in claim 1, in which the copolymer has a number average molecular weight in a range from about 20K to about 800K.

14. A method as in claim 1, in which the copolymer has a number average molecular weight in a range from about 100K to about 600K.

15. A method as in claim 1, in which the copolymer has a number average molecular weight in a range from about 2K to about 200K.

16. A method as in claim 1, in which the copolymerization reaction is carried out using free radical polymerization, atom transfer radical polymerization, cationic polymerization, anionic polymerization, or iniferter polymerization.