IP Library › Granted Patent US 8,653,226
Granted Patent B2
US 8,653,226 · App. 13/132,731 · Granted Feb 18, 2014

Polyesteracetals

Inventors: Stephen A. Miller (Gainesville, FL); Ryan T. Martin (Gainesville, FL)
Assignee: University of Florida Research Foundation, Inc.
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Quick Facts
Patent No.
US 8,653,226
App. No.
13/132,731
Granted
Feb 18, 2014
Kind
B2
Abstract

A polyesteracetal contains —[C(O)(CR 3 R 4 ) x (C(O)) y OCR 1 R 2 O]— repeating unit where x is 0 to 5, y is 0 or 1, and R 1 , R 2 , R 3 and R 4 are independently H, C 1 to C 24 alkyl, C 2 to C 24 alkenyl, C 6 to C 14 aryl, C 7 to C 24 alkylaryl, heteroatom interrupted C 1 to C 24 alkyl, heteroatom interrupted C 2 to C 24 alkenyl, heteroatom interrupted C 4 to C 14 aryl, or heteroatom interrupted C 5 to C 24 alkylaryl, and wherein on average x>1 or y>0. The polyesteracetal can be a homopolymer or copolymer. A method of preparing the polyesteracetal comprises a ring-opening polymerization of a cyclic esteracetal monomer using a metal alkolate, metal alkoxide or metal alkyl initiator.

Claims (21)

1. A polyesteracetal, comprising repeating units of the structure:

wherein: x is 0 to 5; y is 0 to 1; R 1 , R 2 , R 3 and R 4 are independently H, C 1 to C 24 alkyl, C 2 to C 24 alkenyl, C 6 to C 14 aryl, C 7 to C 24 alkylaryl, heteroatom interrupted C 1 to C 24 alkyl, heteroatom interrupted C 2 to C 24 alkenyl, heteroatom interrupted C 4 to C 14 aryl, or heteroatom interrupted C 5 to C 24 alkylaryl; wherein said polyesteracetal is a copolymer comprising a plurality of repeating unit structures, and wherein for said plurality of repeating unit structures, on average, x>1 and y >0.

2. The polyesteracetal of claim 1 , wherein for at least one of said plurality of repeating unit structures said x is 1 or 2 and y is 0, and wherein for said plurality of repeating unit structures, on average, x>1 and y>0.

3. The polyesteracetal of claim 2 , wherein for at least one of said plurality of repeating unit structures said x is 2, y is 0 and R 1 , R 2 , R 3 and R 4 are H, and wherein for said plurality of repeating unit structures, on average, x>1 and y>0.

4. A polyesteracetal, comprising repeating units of the structure:

wherein: x is 0 to 2; y is 1; R 1 , R 2 , R 3 and R 4 are independently H, C 1 to C 24 alkyl, C 2 to C 24 alkenyl, C 6 to C 14 aryl, C 7 to C 24 alkylaryl, heteroatom interrupted C 1 to C 24 alkyl, heteroatom interrupted C 2 to C 24 alkenyl, heteroatom interrupted C 4 to C 14 aryl, or heteroatom interrupted C 5 to C 24 alkylaryl; wherein said x is 0, 1 or 2, and y is 1.

5. The polyesteracetal of claim 4 , wherein said x is 0, 1 or 2, y is 1 and R 1 , R 2 , R 3 and R 4 are H.

6. The polyesteracetal of claim 5 , wherein said x is 0, y is 1 and R 1 and R 2 are H.

7. The polyesteracetal of claim 1 , wherein said polyesteracetal is biodegradable.

8. The polyesteracetal of claim 1 , wherein said polyesteracetal is a thermoplastic.

9. The polyesteracetal of claim 1 , wherein said copolymer further comprises non-esteracetal repeating units.

10. The polyesteracetal of claim 9 , wherein said non-esteracetal repeating units comprise caprolactone or lactide repeating units.

11. A method of preparing a polyesteracetal comprising the steps of:

providing a polymerization mixture comprising a plurality of at least two cyclic esteracetal monomers of the structure:

wherein x is 0 to 5, y is 0 to 1, R 1 , R 2 , R 3 and R 4 are independently H, C 1 to C 24 alkyl, C 2 to C 24 alkenyl, C 6 to C 14 aryl, C 7 to C 24 alkylaryl, heteroatom interrupted C 1 to C 24 alkyl, heteroatom interrupted C 2 to C 24 alkenyl, heteroatom interrupted C 4 to C 14 aryl, or heteroatom interrupted C 5 to C 24 alkylaryl, and wherein for said plurality of at least two cyclic esteracetal monomers, on average, x>1 and y>0; and

polymerizing said cyclic monomers upon addition of an initiator to said polymerization mixture.

12. The method of claim 11 , wherein said polymerization mixture further comprises a solvent.

13. The method of claim 11 , wherein said initiator comprises a metal alkolate, metal alkoxide, or metal alkyl.

14. The method of claim 13 , wherein said metal alkolate comprises tin (II) alkolate, or an aluminum alkoxide.

15. The method of claim 11 , wherein said polymerization mixture further comprises a non-esteracetal monomer.

16. The method of claim 15 , wherein said non-esteracetal monomer comprises caprolactone or cyclic lactide dimer.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 14, 2012
From: MILLER, STEPHEN A.; MARTIN, RYAN T.
To: UNIVERSITY OF FLORIDA RESEARCH FOUNDATION, INC.
Reel/Frame 027698/0280 →
Continuity (2)
Provisional Application 61119911 · Dec 4, 2008
Related Publication 20110237772A1 · Sep 29, 2011