IP Library Granted Patent US 11,873,350
Granted Patent B2
US 11,873,350 · App. 17/233,694 · Granted Jan 16, 2024

Dissolution of oxidized cellulose

Inventors: Valentino J. Tramontano (Brockton, MA); Joshua Kennedy (Somerville, MA); Philip D. Blaskovich (Salem, MA); Rachit Ohri (Framingham, MA); Daniel S. Costa (Somerville, MA); Sajida Farooqi (Hamden, CT)
Assignee: Covidien LP
C08B16/00C08B15/02C08J3/091C08J3/096C08J3/12C08K3/16C08K5/20C08K5/3415C08L1/04A61K9/1652C08J2301/02C08J2301/04
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Quick Facts
Patent No.
US 11,873,350
App. No.
17/233,694
Granted
Jan 16, 2024
Kind
B2
Abstract

A process for dissolving modified cellulose is disclosed. The process includes contacting modified cellulose with a solvent in a mixture to form swelled modified cellulose and then contacting the mixture with a salt to dissolve the swelled modified cellulose.

Claims (40)

1. A process comprising:

forming a mixture by contacting an oxidized cellulose with a solvent to form a swelled oxidized cellulose;

adjusting the mixture to a first temperature;

contacting the swelled oxidized cellulose with a salt to form an oxidized cellulose solution; and

adjusting the oxidized cellulose solution to a second temperature lower than the first temperature, wherein dissolved oxidized cellulose of the oxidized cellulose solution retains from about 80% to about 120% of a degree of oxidation of the oxidized cellulose prior to dissolution or from about 80% to about 120% of a molecular weight of the oxidized cellulose prior to dissolution.

2. The process according to claim 1 , wherein the first temperature is adjusted to a temperature of from about 115° C. to about 145° C.

3. The process according to claim 1 , wherein the first temperature is adjusted to a temperature of from about 120° C. to about 140° C.

4. The process according to claim 1 , wherein the first temperature is adjusted to a temperature of from about 130° C. to about 135° C.

5. The process according to claim 1 , wherein the second temperature is adjusted to a temperature of from about 90° C. to about 120° C.

6. The process according to claim 1 , wherein the second temperature is adjusted to a temperature of from about 100° C. to about 110° C.

7. The process according to claim 1 , wherein the solvent is selected from the group consisting of N,N-Dimethylacetamide, N-methyl-2-pyrrolidinone, and combinations thereof.

8. The process according to claim 1 , wherein the salt is selected from the group consisting of lithium halides, sodium halides, potassium halides, and combinations thereof.

9. The process according to claim 1 , wherein the mixture and the oxidized cellulose solution are formed under an inert atmosphere.

10. A process comprising:

forming a mixture by contacting an oxidized cellulose with a solvent to form a swelled oxidized cellulose;

adjusting the mixture to a first temperature;

contacting the swelled oxidized cellulose with a salt to form an oxidized cellulose solution;

adjusting the oxidized cellulose solution to a second temperature lower than the first temperature; and

forming a plurality of microspheres from the oxidized cellulose solution.

11. The process according to claim 10 , further comprising:

forming an emulsion from the oxidized cellulose solution.

12. The process according to claim 11 , further comprising:

contacting the oxidized cellulose solution with at least one bioactive agent to form a discontinuous phase liquid;

contacting the discontinuous phase liquid with a continuous phase liquid to form the emulsion; and

contacting the emulsion with a third phase liquid to extract the solvent from the emulsion, thereby forming a plurality of modified cellulose microspheres.

13. The process according to claim 12 , wherein the continuous phase liquid is selected from the group consisting of plant-based oils, petroleum-based oils, silicone-based oils, and combinations thereof.

14. The process according to claim 12 , wherein the third phase liquid is miscible with the continuous phase liquid and the discontinuous phase liquid.

15. The process according to claim 14 , wherein the third phase liquid is selected from the group consisting of isopropyl myristate, hexane, triglycerides and combinations thereof.

16. The process according to claim 14 , wherein the third phase liquid is present in an amount from about 130% by volume to about 170% by volume of the continuous phase liquid.

17. The process according to claim 10 , wherein the mixture and the oxidized cellulose solution are formed under an inert atmosphere.

18. A microsphere comprising:

solubilized oxidized cellulose having from about 80% to about 120% of a degree of oxidation of undissolved oxidized cellulose prior to dissolution or from about 80% to about 120% of a molecular weight of the undissolved oxidized cellulose prior to dissolution; and

at least one bioactive agent.

19. The microsphere according to claim 18 , wherein the bioactive agent is selected from the group consisting of a hydrophilic bioactive agent, a protein therapeutic, a biologic, and combinations thereof.

20. The microsphere according to claim 18 , wherein the microsphere is formed by:

contacting an oxidized cellulose solution comprising a solvent with the at least one bioactive agent to form a discontinuous phase liquid;

contacting the discontinuous phase liquid with a continuous phase liquid to form an emulsion; and

contacting the emulsion with a third phase liquid to extract the solvent from the emulsion.

21. The microsphere according to claim 20 , wherein the third phase liquid is miscible with the continuous phase liquid and the discontinuous phase liquid.

22. The microsphere according to claim 20 , wherein the third phase liquid is selected from the group consisting of isopropyl myristate, hexane, triglycerides and combinations thereof.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 19, 2021
From: TRAMONTANO, VALENTINO J.; KENNEDY, JOSHUA; BLASKOVICH, PHILIP; OHRI, RACHIT; COSTA, DANIEL S.; FAROOQI, SAJIDA
To: COVIDIEN LP
Reel/Frame 055955/0963 →
Continuity (4)
Continuation 15353997 · Nov 17, 2016
Continuation 14129187
Provisional Application 61502567 · Jun 29, 2011
Related Publication 20210238314A1 · Aug 5, 2021