Polymers, preparation and use thereof

Patent metadata

Field	Value
Publication number	US-10077324-B2
Application number	US-201414766191-A
Country	US
Kind code	B2
Filing date	Jan 14, 2014
Priority date	Feb 6, 2013
Publication date	Sep 18, 2018
Grant date	Sep 18, 2018

Abstract

The present teachings provide novel polymers, and methods of preparing and using thereof. The novel polymers each includes a sulfide, sulfonyl, or sulfonyl bond. The novel polymer are used to make polycations and/or polyanions, which can be used, for example, to produce adhesive complex coacervates.

First claim

What is claimed is:

1. A coacervate comprising a polycation and a polyanion, wherein the polycation and/or the polyanion comprises a moiety of Formula II:

wherein
A at each occurrence is O, NR 2 , or C(R 3 ) 2 ;
A′ at each occurrence is O, NR 2 , C(R 3 ) 2 or CR 3 ;
R 1 and R 2 at each occurrence independently is hydrogen, alkyl, alkenyl, aryl, arylalkyl, cycloalkyl, heteroaryl, or heterocyclyl, wherein each of the alkyl, alkenyl, aryl, arylalkyl, cycloalkyl, heteroaryl, and heterocyclyl optionally is substituted with one or more substituents selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, heterocyclyl, heteroaryl, alkoxy, aryloxy, cyano, hydroxyl, oxo, imino, halo, amino, phosphate, phosphonate, sulfate, sulfonate and borate;
R 1′ at each occurrence is hydrogen, alkyl, alkenyl, aryl, arylalkyl, cycloalkyl, heteroaryl, or heterocyclyl, wherein each of the alkyl, alkenyl, aryl, arylalkyl, cycloalkyl, heteroaryl, and heterocyclyl optionally is substituted with one or more substituents selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, heterocyclyl, heteroaryl, alkoxy, aryloxy, cyano, hydroxyl, oxo, imino, halo, amino, phosphate, phosphonate, sulfate, sulfonate and borate, wherein at least one R 1′ comprises a vinyl or ethynyl group;
R 3 at each occurrence is hydrogen, alkyl, alkenyl, aryl, arylalkyl, cycloalkyl, heteroaryl, heterocyclyl, hydroxyl, alkoxyl, aroxyl, ester, sulfide, sulfinyl, sulfonyl, halo, cyano, nitro, carbonyl, or carboxylate, wherein each of the alkyl, alkenyl, aryl, arylalkyl, cycloalkyl, heteroaryl, heterocyclyl, alkoxyl, aroxyl, ester, sulfide, sulfinyl, sulfonyl, carbonyl, and carboxylate optionally is substituted with one or more substituents selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, heterocyclyl, heteroaryl, alkoxy, aryloxy, cyano, hydroxyl, oxo, imino, halo, amino, phosphate, phosphonate, sulfate, sulfonate and borate; or
two R 3 groups are combined to form oxo or imino;
R 4 at each occurrence is hydrogen or alkyl;
x is 0, 1, or 2;
m′, m″, n′, and n″ at each occurrence is an integer; and
J represents other parts of the polycation or polyanion.

2. The coacervate of claim 1 , wherein A at each occurrence is O or C(R 3 ) 2 .

3. The coacervate of claim 1 , wherein at least one A is C(R 3 ) 2 , wherein R 3 is hydrogen or optionally substituted alkyl.

4. The coacervate of claim 1 , wherein at least one A′ is oxygen.

5. The coacervate of claim 1 , wherein the moiety of Formula II is of Formula IIIa or Formula IIIb:

wherein p′ and p″ each at each occurrence is an integer.

6. The coacervate of claim 1 , wherein the polycation comprises the moiety of Formula II.

7. The coacervate of claim 6 , wherein the polycation comprises one or more amino groups.

8. The coacervate of claim 6 , wherein the polycation comprises a peptide or an engineering protein.

9. The coacervate of claim 1 , wherein the polyanion comprises the moiety of Formula II.

10. The coacervate of claim 9 , wherein the polyanion comprises a sulfate, a sulfonate, a carboxylate, a borate, a boronate, a phosphonate, or a phosphate group.

11. The coacervate of claim 1 , wherein the polycation and/or the polyanion is cross-linked.

12. The coacervate of claim 1 , wherein the coacervate is an adhesive complex coacervate.

Assignees

• Kci Licensing Inc

Inventors

• Vail Neal

Classifications

• A61L24/0015 Primary

  Medicaments; Biocides · CPC title

• C08G83/00

  Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00 · CPC title

• C08F28/02 Primary

  by a bond to sulfur · CPC title

• A61L24/043

  Mixtures of macromolecular materials · CPC title