IP Library Granted Patent US 9,255,929
Granted Patent B2
US 9,255,929 · App. 12/891,524 · Granted Feb 9, 2016

Zwitterionic polymers having biomimetic adhesive linkages

Inventors: Shaoyi Jiang (Redmond, WA); Changlu Gao (Fukuoka, JP); Guozhu Li (Shanghai, CN); Hong Xue (Seattle, WA); Norman David Brault, Jr. (Seattle, WA)
Assignee: University of Washington
G01N33/6845
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Quick Facts
Patent No.
US 9,255,929
App. No.
12/891,524
Granted
Feb 9, 2016
Kind
B2
Abstract

Zwitterionic polymers having adhesive groups, methods for making the polymers, surfaces having the polymers grafted thereto and grafted therefrom, and methods for making and using the polymer-modified surfaces.

Claims (29)

1. A polymer, comprising:

(a) polymer backbone;

(b) a plurality of cationic centers, each cationic center covalently coupled to the polymer backbone by a first linker;

(c) an anionic center covalently coupled to each cationic center by a second linker; and

(d) one or more dihydroxyphenyl groups covalently coupled to the terminus of the polymer backbone.

2. The polymer of claim 1 , wherein the cationic center is selected from the group consisting of ammonium, imidazolium, triazolium, pyridinium, morpholinium, oxazolidinium, pyrazinium, pyridazinium, pyrimidinium, piperazinium, pyrrolidinium, and phosphonium.

3. The polymer of claim 1 , wherein the anionic center is selected from the group consisting of a carboxylic acid group (CO 2 − ), a sulfuric acid group (SO 4 −2 ), a sulfonic acid group (SO 3 − ), a sulfinic acid group (SO 2 − ), a phosphonic acid group (PO 4 −2 ), and a phosphinic acid group (PO 3 − ).

4. The polymer of claim 1 , wherein the dihydroxyphenyl group is a 3,4-dihydroxyphenyl group.

5. The polymer of claim 1 having the formula:

(DHP) m -L 3 -PB-(L 1 -N + (R a )(R b )-L 2 -A(=O)—OR c ) n

wherein

PB is the polymer backbone having n pendant groups L 1 -N + (R a )(R b )-L 2 -A(=O)—OR c ) and m dihydroxyphenyl groups covalently coupled to the polymer backbone through a linker moiety L 3 ;

DHP is a dihydroxyphenyl group;

N + is the cationic center;

R a and R b are independently selected from alkyl and aryl, or taken together with the nitrogen to which they are attached form a cationic center;

A(=O)—OR c is the anionic center, wherein R c is hydrogen or a counterion, and wherein A is selected from the group consisting of C, S, SO, P, or PO;

L 1 is a linker that covalently couples the cationic center to the polymer backbone;

L 2 is a linker that covalently couples the cationic center to the anionic center;

L 3 is a linker moiety that covalently couples the m dihydroxyphenyl groups to the polymer backbone;

n is an integer from 1 to about 1,000; and

m is from 1 to 20.

6. The polymer of claim 5 , wherein R a and R b are independently selected from the group consisting of C1-C5 straight chain and branched alkyl groups.

7. The polymer of claim 5 , wherein L 1 is selected from the group consisting of —C(═O)O—(CH 2 ) n — and —C(═O)NH—(CH 2 ) n —, wherein n is an integer from 1 to 10.

8. The polymer of claim 5 , wherein L 2 is —(CH 2 ) n —, where n is an integer from 1 to 5.

9. The polymer of claim 5 , wherein A is selected from the group consisting of C, SO, and PO 2 .

10. The polymer of claim 5 , wherein n is from about 10 to about 500.

11. The polymer of claim 5 , wherein m is 1 or 2.

12. A surface of a substrate coated with a plurality of polymers of claim 1 .

13. A method for treating a surface comprising applying a polymer of claim 1 to the surface.

Assignments (3)
CONFIRMATORY LICENSE Recorded Oct 27, 2014
From: WASHINGTON, UNIVERSITY OF
To: NAVY, SECRETARY OF THE UNITED STATES OF AMERICA
Reel/Frame 034095/0045 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 30, 2011
From: JIANG, SHAOYI; GAO, CHANGLU; LI, GUOZHU; XUE, HONG; BRAULT, NORMAN DAVID, JR.
To: WASHINGTON, UNIVERSITY OF
Reel/Frame 026051/0298 →
CONFIRMATORY LICENSE Recorded Nov 12, 2010
From: UNIVERSITY OF WASHINGTON
To: UNITED STATES GOVERNMENT; DEFENSE THREAT REDUCTION AGENCY
Reel/Frame 025356/0424 →
Continuity (2)
Provisional Application 61245892 · Sep 25, 2009
Related Publication 20110105712A1 · May 5, 2011