Aqueous polyglycidol synthesis with ultra-low branching

Patent metadata

Field	Value
Publication number	US-11820864-B2
Application number	US-202117487053-A
Country	US
Kind code	B2
Filing date	Sep 28, 2021
Priority date	Jan 24, 2014
Publication date	Nov 21, 2023
Grant date	Nov 21, 2023

Abstract

Disclosed herein are glycidol-based polymers, nanoparticles, and methods related thereto useful for a variety of applications, including, but not limited to, drug delivery. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

First claim

What is claimed is:

1. A polymer comprising repeating units selected from

and repeating units selected from

wherein R 0 is selected from H, alkyl, NH 2 , and R 1 ;
wherein R 1 comprises a crosslinking functionality;
wherein repeating units A1, A2, B1, and B2 account for at least about 50 wgt % of the polymer;
wherein the ratio of (A1+A2):(B1+B2) is greater than 1, and
wherein the polymer does not comprise an initiator other than glycidol.

2. The polymer of claim 1 , wherein the polymer does not comprise a metal catalyst residue.

3. The polymer of claim 2 , wherein the metal catalyst residue is a tin catalyst residue.

4. The polymer of claim 1 , wherein the degree of branching is between 0.15 and 0.30.

5. The polymer of claim 4 , wherein the degree of branching is between 0.20 and 0.30.

6. The polymer of claim 1 , wherein the polymer is further conjugated to a protein.

7. The polymer of claim 6 , wherein the protein is albumin.

8. The polymer of claim 1 , wherein the polymerization step is performed at a temperature from 60° C. to 100° C.

9. The polymer of claim 8 , wherein the polymerization step is performed at a temperature of about 80° C.

10. A pharmaceutical composition comprising a polymer of claim 1 and a pharmaceutically acceptable carrier.

11. The pharmaceutical composition of claim 10 , wherein the pharmaceutical composition further comprises a pharmaceutically active agent or a biologically active agent.

12. A method for making a polymer, the method comprising the step of polymerizing glycidol in an aqueous solution, wherein the method makes a polymer that comprises repeating units selected from:

and repeating units selected from:

wherein R 0 is selected from H, alkyl, NH 2 , and R 1 ;
wherein R 1 comprises a crosslinking functionality;
wherein repeating units A1, A2, B1, and B2 account for at least about 50 wgt % of the polymer;
wherein the ratio of (A1+A2):(B1+B2) is greater than 1, and
wherein the polymer does not comprise an initiator other than glycidol.

13. The method of claim 12 , wherein the aqueous solution is a buffer.

14. The method of claim 12 , wherein the aqueous solution does not comprise a metal catalyst.

15. The method of claim 12 , wherein the aqueous solution has a pH from about 3.0 to about 9.0.

16. The method of claim 12 , wherein the polymerization is initiated from a macromolecular structure.

17. The method of claim 12 , wherein the polymerization step is performed at a temperature from about 50° C. to about 120° C.

18. The method of claim 12 , wherein the polymer does not comprise a

moiety.

19. The method of claim 12 , wherein the polymer further comprises at least one repeating unit formed from a monomer selected from:

or a combination thereof.

Assignees

• Univ Vanderbilt

Inventors

• Harth Eva M
• Spears Benjamin R

Classifications

• C08G65/34 Primary

  from hydroxy compounds or their metallic derivatives {(C08G65/26 takes precedence)} · CPC title

• C08G65/22 Primary

  Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring · CPC title

• C08G2650/24

  Polymeric initiators · CPC title

• C08G2650/38

  containing oxygen in addition to the ether group · CPC title

• C08G2650/56

  Polyhydroxyethers, e.g. phenoxy resins · CPC title