Antimicrobial polymers formed by bulk polyaddition

• US 9,642,360 B2
• Filed: 06/25/2015
• Issued: 05/09/2017
• Est. Priority Date: 06/25/2015
• Status: Expired due to Fees

• Current Assignee: Agency For Science Technology and Research (Government of Singapore), International Business Machines Corporation
• Original Assignee: Agency For Science Technology and Research (Government of Singapore), International Business Machines Corporation
• Inventors: Chan, Julian M. W., Hedrick, James L., Ono, Robert J., Teo, Jye Yng, Yang, Yi Yan, Zhang, Mu San
• Primary Examiner(s): FALKOWITZ, ANNA R
• Application Number:
  US14/749,764
• Publication Number:
  US 20160374335A1
• Time in Patent Office: 684 Days
• Field of Search: None
• CPC Class Codes: A01N 25/10 Macromolecular compounds
• CPC Class Codes: A01N 33/12 Quaternary ammonium compounds
• CPC Class Codes: C08G 73/02 Polyamines
• CPC Class Codes: C08G 73/0206 Polyalkylene(poly)amines
• CPC Class Codes: C08G 73/0213 Preparatory process
• CPC Class Codes: C08G 73/024 Polyamines containing oxygen in the form of ether bonds in the main chain

Abstract

Cationic antimicrobial polymers have been synthesized by a bulk addition polymerization of a nucleophilic agent comprising two tertiary amines and an electrophilic agent that comprises two leaving groups and an aromatic ring between the leaving groups. The reaction solvent for the polymerization is chosen to allow precipitation of the cationic polymer at the polymerization temperature, thereby limiting molecular weight. Quaternization and polymerization occur concurrently. The cationic polymers can be highly active against Gram-negative and Gram-positive microbes, and/or fungi. The cationic polymers can also be non-hemolytic and non-cytotoxic at the effective concentration against the microbes.

Claims

1. A cationic polymer comprising:

i) a cationic repeat unit of formula (C-1);

2. The cationic polymer of claim 1, wherein each X′

of formulas (C-1) and (C-3) is an independent anion selected from the group consisting of chloride, bromide, and iodide.

3. The cationic polymer of claim 1, wherein the cationic polymer is toxic to a microbe selected from the group consisting of Gram-positive microbes, Gram-negative microbes, fungi, and combinations thereof.

4. The cationic polymer of claim 1, wherein each R′

is ethyl.

5. The cationic polymer of claim 1, wherein the cationic polymer has a number average molecular weight of about 1,000 to about 10,000.

6. The cationic polymer of claim 1, wherein each R′

is methyl.

7. The cationic polymer of claim 1, wherein each X′

of formulas (C-1) and (C-3) is a chloride ion.

8. The cationic polymer of claim 1, wherein each R′

is propyl.

9. The cationic polymer of claim 1, wherein the cationic polymer is a random copolymer.

10. The cationic polymer of claim 1, wherein the cationic polymer comprises the cationic repeat units of formulas (C-1) and (C-3) in a (C-1):

(C-3) molar ratio of 90;

10 to 10;

90.

11. The cationic polymer of claim 1, wherein each R″

is methyl.

12. An antimicrobial composition, comprising the cationic polymer of claim 1 and a second component.

13. The antimicrobial composition of claim 12, wherein the composition is an aqueous mixture of the cationic polymer.

14. The antimicrobial composition of claim 12, wherein the antimicrobial composition is selected from the group consisting of laundry detergents, cosmetics, soaps, hand washes, lotions, and contact lens disinfectants.

15. The antimicrobial composition of claim 12, wherein the cationic polymer is a random copolymer of (C-1) and (C-3).

16. A method of killing a microbe, comprising contacting the microbe with the cationic polymer of claim 1.

17. The method claim 16, wherein the cationic polymer is a random copolymer of (C-1) and (C-3).

18. A method of forming the cationic polymer of claim 1, comprising:

forming a reaction mixture comprising i) a solvent, ii) an electrophilic agent of structure

19. A cationic polymer, comprising a cationic repeat unit of formula (C-3):

20. The cationic polymer of claim 19, wherein the cationic polymer is a homopolymer.

21. The cationic polymer of claim 19, wherein the cationic polymer is a random copolymer comprising a second cationic repeat unit of formula (C-5):

22. An antimicrobial composition, comprising the cationic polymer of claim 19 and a second component.

23. The antimicrobial composition of claim 22, wherein the cationic polymer is a homopolymer.