IP Library › Granted Patent US 12,234,314

Granted Patent B2

US 12,234,314 · App. 17/047,716 · Granted Feb 25, 2025

Zwitterionic polymers for biomedical applications

Inventors: Gang Cheng (Chicago, IL); Huifeng Wang (Chicago, IL)

Assignee: The Board of Trustees of the University of Illinois

C08G18/0833 A61L27/18 A61L29/06 A61L31/06 C08G18/10 C08G18/3206 C08G18/3275 C08G18/3821 C08G18/4833 C08G18/73 C08G2210/00

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Patent No.: US 12,234,314
App. No.: 17/047,716
Granted: Feb 25, 2025
Kind: B2

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Abstract

Provided herein are polymers having a polymer backbone including a zwitterionic precursor monomeric unit having a secondary or tertiary amine in the polymer backbone, as well as methods of making and using the same.

Claims (50)

1. A polymer, comprising:

a polymer backbone:

comprising a first monomeric unit, wherein the first monomeric unit is derived from a combination consisting of an isocyanate and a diol or polyol; and

one or more second monomeric units, wherein the one or more second monomeric units comprise a zwitterionic precursor monomeric unit having a structure according to one or more of Formula (A1) and (B1):

wherein in Formulas (A1) and (B1):

each X is independently O, NR a , S or Se; and,

each R 1 , R 2 , and R 3 is independently selected from —(CH 2 ) n —, —(CH 2 ) n O(CH 2 ) m —, —(CH 2 CH 2 OCH 2 CH 2 ) n —, —(CH 2 CH 2 O) n CH 2 CH 2 —, —((CH 2 ) 1-8 C(O)O) n (CH 2 ) m —, —((CH 2 ) 1-8 C(O)O) n (CH 2 CH 2 O) m (OC(O)(CH 2 ) 1-8 ) p —, —((CH 2 ) 1-8 C(O)O) n (CH 2 CH 2 ) m (OC(O)(CH 2 ) 1-8 ) p —, —(CH 2 C(O)O) m (CH 2 CH 2 ) n (OC(O)CH 2 ) m —, —(CH(CH 3 )C(O)O) m (CH 2 CH 2 ) n (OC(O)CH(CH 3 )) m —, —(CH(CH 3 )C(O)O) m (CH 2 CH 2 ) n (OC(O)CH(CH 3 )) m —, —((CH 2 ) n OC(O)O)(CH 2 CH 2 ) m , —(CH 2 ) n NHC(O)(CH 2 ) m —, and —(CH 2 ) n C(O)NH(CH 2 ) m ;

each R a and R 4 is independently selected from —H, —(CH 2 CH 2 O) n CH 3 , —(CH 2 CH 2 O) n (CH 2 ) m CH 3 , —(CH 2 CH 2 O) n (CH 2 ) m OH, —((CH 2 ) n O) m ((CH 2 ) p O) q (CH 2 ) r OH, —(CH 2 CH 2 O) n H, —(CH 2 ) n OH, —(CH 2 ) n O(CH 2 ) m OH, —(CH 2 CH 2 OCH 2 CH 2 ) n OH, —(CH 2 CH 2 O) n CH 2 CH 2 OH, —((CH 2 ) 1-8 C(O)O) n (CH 2 ) m OH, —((CH 2 ) 1-8 C(O)O) n (CH 2 CH 2 O) m (OC(O)(CH 2 ) 1-8 ) p OH, —((CH 2 ) 1-8 C(O)O) n (CH 2 CH 2 ) m (OC(O)(CH 2 ) 1-8 ) m OH, —(CH 2 C(O)O) n (CH 2 CH 2 ) m (OC(O)CH 2 ) p OH, —(CH(CH 3 )C(O)O) n (CH 2 CH 2 ) m (OC(O)CH(CH 3 )) p OH, —((CH 2 ) n OC(O)O)(CH 2 CH 2 ) m OH, —(CH 2 ) n NHC(O)(CH 2 ) m OH, and —(CH 2 ) n C(O)NH(CH 2 ) m OH, C 1-n alkyl, C 1-n alkenyl, C 1-n alkynyl, C 6-10 aryl, and succinimidyl, wherein any one or more H atoms of R a or R 4 can optionally be replaced with an F atom; and

each n, m, p, q, r, and s is independently 1 to 10,000.

2. A polymer comprising:

a polymer backbone comprising:

a first monomeric unit derived from a compound consisting of an isocyanate and a diol or a polyol, and

one or more second monomeric units, the one or more second monomeric units comprising a zwitterionic precursor monomeric unit, wherein the zwitterionic precursor monomeric unit comprises a secondary or a tertiary amine within the polymer backbone; and wherein the polymer backbone comprises repeating units of Formula (I):

wherein

each R 1 and R 2 is independently selected from —(CH 2 ) n —, —(CH 2 ) n O(CH 2 ) m —, —(CH 2 CH 2 OCH 2 CH 2 ) n —, —(CH 2 CH 2 O) n CH 2 CH 2 —, —((CH 2 ) 1-8 C(O)O) n (CH 2 ) m —, —((CH 2 ) 1-8 C(O)O) n (CH 2 CH 2 O) m (OC(O)(CH 2 ) 1-8 ) p —, —((CH 2 ) 1-8 C(O)O) n (CH 2 CH 2 ) m (OC(O)(CH 2 ) 1-8 ) p —, —(CH 2 C(O)O) m (CH 2 CH 2 ) n (OC(O)CH 2 ) m —, —(CH(CH 3 )C(O)O) m (CH 2 CH 2 ) n (OC(O)CH(CH 3 )) m —, —(CH(CH 3 )C(O)O) m (CH 2 CH 2 ) n (OC(O)CH(CH 3 )) m —, —((CH 2 ) n OC(O)O)(CH 2 CH 2 ) m , —(CH 2 ) n NHC(O)(CH 2 ) m —, and —(CH 2 ) n C(O)NH(CH 2 ) m ;

R 3 is —(CH 2 ) 1-5 —;

each R 4 is independently selected from —H, —(CH 2 CH 2 O) n CH 3 , —(CH 2 CH 2 O) n (CH 2 ) m CH 3 , —(CH 2 CH 2 O) n (CH 2 ) m OH, —((CH 2 ) n O) m ((CH 2 ) p O) q (CH 2 ) r OH, —(CH 2 CH 2 O) n H, —(CH 2 ) n OH, —(CH 2 ) n O(CH 2 ) m OH, —(CH 2 CH 2 OCH 2 CH 2 ) n OH, —(CH 2 CH 2 O) n CH 2 CH 2 OH, —((CH 2 ) 1-8 C(O)O) n (CH 2 ) m OH, —((CH 2 ) 1-8 C(O)O) n (CH 2 CH 2 O) m (OC(O)(CH 2 ) 1-8 ) p OH, —((CH 2 ) 1-8 C(O)O) n (CH 2 CH 2 ) m (OC(O)(CH 2 ) 1-8 ) m OH, —(CH 2 C(O)O) n (CH 2 CH 2 ) m (OC(O)CH 2 ) p OH, —(CH(CH 3 )C(O)O) n (CH 2 CH 2 ) m (OC(O)CH(CH 3 )) p OH, —((CH 2 ) n OC(O)O)(CH 2 CH 2 ) m OH, —(CH 2 ) n NHC(O)(CH 2 ) m OH, and —(CH 2 ) n C(O)NH(CH 2 ) m OH, C 1-n alkyl, C 1-n alkenyl, C 1-n alkynyl, C 6-10 aryl, and succinimidyl, wherein any one or more H atoms of R a or R 4 can optionally be replaced with an F atom;

each of R 5 and R 6 is independently —(CH 2 ) n —, —(CH 2 ) n O(CH 2 ) m —, —(CH 2 CH 2 O) n CH 2 CH 2 —, —(CH 2 CH 2 ) n (CH 2 ) m —, —(CH 2 ) n (CH 2 CH 2 O)) n (CH 2 ) p —, —((CH 2 ) 1-8 C(O)O) n (CH 2 ) m —, —((CH 2 ) 1-8 C(O)O) n (CH 2 CH 2 O) m (OC(O)(CH 2 ) 1-8 ) p —, —((CH 2 ) 1-8 C(O)O) n (CH 2 CH 2 ) m (OC(O)(CH 2 ) 1-8 ) p —, —(CH 2 C(O)O) n (CH 2 CH 2 ) m (OC(O)CH 2 ) p —, —(CH(CH 3 )C(O)O) n (CH 2 CH 2 ) m (OC(O)CH(CH 3 )) p —, —(CH(CH 3 )C(O)O) n (CH 2 CH 2 ) m (OC(O)CH(CH 3 )) p —, —((CH 2 ) n OC(O)O)(CH 2 CH 2 ) m —, —(CH 2 ) n NHC(O)(CH 2 ) m —, —(CH 2 ) n C(O)NH(CH 2 ) m , or —(CH 2 ) n CH(OH)(CH 2 ) m —

each n, m, p, q, and r is independently 1 to 10,000;

a is 1 to 100,000; and,

b is 0 to 100,000.

3. The polymer of claim 2 , wherein the isocyanate comprises hexamethylene diisocyanate (HDI).

4. The polymer of claim 1 , wherein the zwitterionic precursor monomeric unit has a structure:

5. The polymer of claim 2 , wherein R 6 is —(CH 2 )CH(OH)(CH 2 )—.

6. A polymer comprising:

a polymer backbone comprising:

a first monomeric unit derived from a compound consisting of an isocyanate and a diol or a polyol, and

wherein the polymer backbone comprises repeating units of Formula (II):

wherein each R 4 is independently selected from —H, —(CH 2 CH 2 O) n CH 3 , —(CH 2 CH 2 O) n (CH 2 ) m CH 3 , —(CH 2 CH 2 O) n (CH 2 ) m OH, —((CH 2 ) n O) m ((CH 2 ) p O) q (CH 2 ) r OH, —(CH 2 CH 2 O) n H, —(CH 2 ) n OH, —(CH 2 ) n O(CH 2 ) m OH, —(CH 2 CH 2 OCH 2 CH 2 ) n OH, —(CH 2 CH 2 O) n CH 2 CH 2 OH, —((CH 2 ) 1-8 C(O)O) n (CH 2 ) m OH, —((CH 2 ) 1-8 —C(O)O) n (CH 2 CH 2 O) m (OC(O)(CH 2 ) 1-8 ) p OH, —((CH 2 ) 1-8 C(O)O) n (CH 2 CH 2 ) m (OC(O)(CH 2 ) 1-8 ) m OH, —(CH 2 C(O)O) n (CH 2 CH 2 ) m (OC(O)CH 2 ) p OH, —(CH(CH 3 )C(O)O) n (CH 2 CH 2 ) m (OC(O)CH(CH 3 )) p OH, —((CH 2 ) n OC(O)O)(CH 2 CH 2 ) m OH, —(CH 2 ) n NHC(O)(CH 2 ) m OH, and —(CH 2 ) n (C(O)NH(CH 2 ) m OH, C 1-n alkyl, C 1-n alkenyl, C 1-n alkynyl, C 6-10 aryl, and succinimidyl, wherein any one or more H atom of R 4 can optionally be replaced with an F atom;

R 5 is —(CH 2 ) n —, —(CH 2 ) n O(CH 2 ) m —, —(CH 2 CH 2 OCH 2 CH 2 ) n —, —(CH 2 CH 2 O) n CH 2 CH 2 —, —(CH 2 CH 2 ) n (CH 2 ) m —, —(CH 2 ) n (CH 2 CH 2 O) n (CH 2 ) p —, —((CH 2 ) 1-8 C(O)O) n (CH 2 ) m —, —((CH 2 ) 1- 8 C(O)O) n (CH 2 CH 2 O) m (OC(O)(CH 2 ) 1-8 ) p —, —((CH 2 ) 1-8 C(O)O) n (CH 2 CH 2 ) m (OC(O)(CH 2 ) 1-8 ) p —, —(CH 2 C(O)O) n (CH 2 CH 2 ) m (OC(O)CH 2 ) p —, —(CH(CH 3 )C(O)O) n (CH 2 CH 2 ) m (OC(O)CH(CH 3 )) p —, —(CH(CH 3 )C(O)O) n (CH 2 CH 2 ) m (OC(O)CH(CH 3 )) p —, —((CH 2 ) n OC(O)O)(CH 2 CH 2 ) m, —(CH 2 ) n NHC(O)(CH 2 ) m —, —(CH 2 ) n C(O)NH(CH 2 ) m —, or —(CH 2 ) n CH(OH)(CH 2 ) m —; and

each n, m, p, q, and r is independently 1 to 10,000;

or wherein the polymer backbone comprises repeating units of Formula (III), (IV), or (VI):

wherein x is 1 to 1,000,000;

or wherein the polymer backbone comprises repeating units of Formula (V):

or wherein the polymer backbone comprises repeating units of Formula (VII):

wherein Z is O or NH, and x is 1 to 30.

7. The polymer of claim 2 , wherein:

R 5 is —(CH 2 ) 6 —; and,

each R 4 is —(CH 2 ) 2 OH or —CH 2 CH 3 .

8. The polymer of claim 2 , wherein the zwitterionic precursor monomeric unit has a structure according to Formula (C1), (D1), or (E1):

wherein:

each X is independently O, NR a , S, or Se;

each R 7 , R 8 , R 9 , R 11 , R 12 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 and R 20 is independently selected from —(CH 2 ) n —, —((CH 2 ) n O) m ((CH 2 ) p O) q (CH 2 ) r —, —(CH 2 ) n O(CH 2 ) m —, —(CH 2 CH 2 OCH 2 CH 2 ) n —, —(CH 2 CH 2 O) n CH 2 CH 2 —, —((CH 2 ) 1-8 C(O)O) m (CH 2 ) n —, —((CH 2 ) 1-8 C(O)O) m (CH 2 CH 2 O)(OC(O)(CH 2 ) 1-8 ) p —, —((CH 2 ) 1-8 C(O)O) m (CH 2 CH 2 ) n (OC(O)(CH 2 ) 1-8 ) p —, —(CH 2 C(O)O) m (CH 2 CH 2 ) n (OC(O)CH 2 ) p —, —(CH(CH 3 )C(O)O) m (CH 2 CH 2 ) n (OC(O)CH(CH 3 )) p —, —(CH(CH 3 )C(O)O) m (CH 2 CH 2 ) n (OC(O)CH(CH 3 )) p —, —((CH 2 ) n OC(O)O)(CH 2 CH 2 ) m , —(CH 2 ) n NHC(O)(CH 2 ) m —, and —(CH 2 ) n C(O)NH(CH 2 ) m ;

each R a , R 10 , R 13 , R 21 , and R 22 is independently —H, —(CH 2 CH 2 O) n CH 3 , —(CH 2 CH 2 O) n (CH 2 ) m CH 3 , —(CH 2 CH 2 O) n (CH 2 ) m OH, —((CH 2 ) n O) m ((CH 2 ) p O) q (CH 2 ) r OH, —(CH 2 CH 2 O) n H, —(CH 2 ) n OH, —(CH 2 ) n O(CH 2 ) m OH, —(CH 2 CH 2 OCH 2 CH 2 ) n OH, —(CH 2 CH 2 O) n CH 2 CH 2 OH, —(CH 2 CH 2 OCH 2 CH 2 ) n OH, —((CH 2 ) 1-8 C(O)O) n (CH2) m OH, —((CH 2 ) 1-8 C(O)O) n (CH 2 CH 2 O) m (OC(O)(CH 2 ) 1-8 ) p OH, —((CH 2 ) 1-8 C(O)O) n (CH 2 CH 2 ) m (OC(O)(CH 2 ) 1-8 ) p OH, —(CH 2 C(O)O) n (CH 2 CH 2 ) m (OC(O)CH 2 ) p OH, —(CH(CH 3 )C(O)O) n (CH 2 CH 2 ) m (OC(O)CH(CH 3 )) p OH, —(CH(CH 3 )C(O)O) n (CH 2 CH 2 ) m (OC(O)CH(CH 3 )) p OH, —((CH 2 ) n OC(O)O)(CH 2 CH 2 ) m OH, —(CH 2 ) n NHC(O)(CH 2 ) m OH, —(CH 2 ) n C(O)NH(CH 2 ) m OH, C 1-n alkyl, C 1-n alkenyl, C 1-n alkynyl, or C 6-10 aryl, wherein any one or more H atoms of R a , R 10 , R 13 , R 21 , or R 22 can optionally be replaced with an F atom; and,

each n, m, p, q and r is independently 1 to 10,000.

9. The polymer of claim 8 , wherein the zwitterionic precursor monomeric unit has a structure:

10. The polymer of claim 2 , wherein the ratio of hydroxyl groups in the zwitterionic precursor monomeric unit:hydroxyl groups in the diol or polyol:isocyanate groups in the isocyanate is selected from the group of 2:8:10, 4:6:10, 6:4:10, 8:2:10, 75:25:100, 50:50:100, and 25:75:100.

11. The polymer of claim 10 , wherein the ratio is selected from the group consisting of 2:8:10, 4:6:10, 6:4:10, and 8:2:10.

12. The polymer of claim 2 , wherein the polymer is hydrolyzed.

Assignments (1)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 1, 2021

From: CHENG, GANG; WANG, HUIFENG

To: THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS

Reel/Frame 055442/0165 →

Continuity (2)

Provisional Application 62659939 · Apr 19, 2018

Related Publication 20210163657A1 · Jun 3, 2021

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