Catechol-rich polymers from N-substituted maleimides

Patent metadata

Field	Value
Publication number	US-9540462-B2
Application number	US-201514960799-A
Country	US
Kind code	B2
Filing date	Dec 7, 2015
Priority date	Dec 5, 2014
Publication date	Jan 10, 2017
Grant date	Jan 10, 2017

Abstract

Monomers and polymers, and a method of making polymers that retain the ability of the polymer to form reversible and irreversible bonds are provided. Gels comprising the polymers have the ability to coordinate metal ions and bind biopolymers.

First claim

We claim:

1. A polymer, comprising a plurality of polymer blocks represented by Formula III:

wherein, independently for each occurrence:
Y is —OR 3 or —N(R 1 )(R 2 );
Z is hydrogen or optionally substituted alkyl, acyl, acyloxy, aryl, sulfonate, sulfone, sulfoxide, or sulfonamide;
L is —(C(R 1 ) 2 ) n —, or —(C(R 1 ) 2 ) n O—;
R is selected from the group consisting of hydrogen, hydroxyl, halogen, nitro, cyano, alkyl, alkenyl, acyl, aryl, alkylamino, acylamino, alkoxy, acyloxy, hydroxyalkyl, alkoxyalkyl, aminoalkyl, (alkylamino)alkyl, alkylthio, thioalkyl, (alkylthio)alkyl, alkynyl, carboxyl, sulfate, amino, ether, thioether, ester, amide, thioester, carbonate, carbamate, urea, sulfonate, sulfone, sulfoxide, sulfonamide, heteroaryl, carbocyclyl, heterocyclyl, aralkyl, arylalkoxy, heteroaralkyl, carbocyclylalkyl, heterocyclylalkyl, and —OR 2 ; provided that two instances of R represent —OR 2 ;
R 1 is hydrogen or alkyl;
R 2 is hydrogen or optionally substituted alkyl, acyl, or aryl;
R 3 is hydrogen or alkyl;
n is 1, 2, 3, 4, 5, or 6; and
m is 1 to 500,000.

2. The polymer of claim 1 , wherein said two instances of —OR 2 have an ortho relationship.

3. The polymer of claim 1 , wherein Z is hydrogen.

4. The polymer of claim 1 , wherein R 2 is acyl.

5. The polymer of claim 1 , wherein R 1 is hydrogen; Z is hydrogen; n is 2; L is —(C(R 1 ) 2 ) m —; —C 6 (R) 5 is 3,4-bis(R 2 O)phenyl; and R 2 is hydrogen or —C(O)CH 3 .

6. The polymer of claim 1 , further comprising a metal cation, wherein the metal cation is coordinated to the polymer.

7. The polymer of claim 6 , wherein the metal cation is a transition metal cation.

8. The polymer of claim 7 , wherein the transition metal cation is Fe 2+ or Fe 3+ .

9. The polymer of claim 1 , wherein R 1 is hydrogen or methyl.

10. The polymer of claim 1 , wherein R 1 is hydrogen.

11. The polymer of claim 1 , wherein n is 2, 3, or 4.

12. The polymer of claim 1 , wherein n is 2.

13. The polymer of claim 1 , wherein L is —(C(R 1 ) 2 ) n —.

14. The polymer of claim 1 , wherein three instances of R represent hydrogen.

15. The polymer of claim 4 , wherein R 2 is —C(O)CH 3 .

16. The polymer of claim 1 , wherein R 2 is hydrogen.

17. The polymer of claim 1 , wherein Y is —OR 3 .

18. The polymer of claim 17 , wherein R 3 is hydrogen.

19. The polymer of claim 1 , wherein m is 10 to 100,000.

20. The polymer of claim 1 , wherein m is 10,000 to 100,000.

Assignees

• Massachusetts Inst Technology

Inventors

• Glassman Matthew J
• Olsen Bradley D

Classifications

• C07D207/452

  with hydrocarbon radicals, substituted by hetero atoms, directly attached to the ring nitrogen atom · CPC title

• C08F22/40 Primary

  Imides, e.g. cyclic imides · CPC title