Alternating ring-opening metathesis polymerization

Patent metadata

Field	Value
Publication number	US-9803047-B2
Application number	US-201715438305-A
Country	US
Kind code	B2
Filing date	Feb 21, 2017
Priority date	Jul 22, 2013
Publication date	Oct 31, 2017
Grant date	Oct 31, 2017

Abstract

The invention relates to the field of polymers and olefin polymerization, and more specifically olefin metathesis polymerization. The invention provides regioregular alternating polymers and methods of synthesizing such polymers. To demonstrate, polymers were synthesized and modified with a FRET pair (Trp/Dansyl) post-polymerization.

First claim

We claim:

1. A polymer comprising the repeating unit (Ib) or (Ic):

wherein R is selected from the group consisting of H, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 3 -C 8 cycloalkyl, heterocyclyl, aryl, C 1 -C 20 alkoxy, C 1 -C 20 alkenyloxy, C 3 -C 6 cycloalkyloxy, aryloxy, heterocyclyloxy, C 1 -C 20 alkylamino, C 1 -C 20 alkenylamino, C 3 -C 8 cycloalkylamino, heterocyclylamino, or arylamino and may be optionally substituted with up to three substituents selected from halo, CN, NO 2 , oxo, alkyl, cycloalkyl, alkenyl, alkynyl, aralkyl, aryl, and a heterocyclic group;
n is a number between 2 and 20;
R 1 through R 6 are independently selected from the group consisting of H, aldehyde, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 3 -C 6 cycloalkyl, aryl, heterocyclyl, C 1 -C 20 alkoxy, C 1 -C 20 acyloxy, C 2 -C 20 alkenyloxy, C 3 -C 6 cycloalkyloxy, aryloxy, heterocyclyloxy, C 1 -C 20 alkylamino, C 2 -C 20 alkenylamino, C 3 -C 8 cycloalkylamino, heterocyclylamino, arylamino, or halogen;
R 1 through R 6 may be taken together to form a 5- to 7-membered ring which may be optionally substituted with up to three substituents selected from halo, CN, NO 2 , oxo, alkyl, cycloalkyl, alkenyl, alkynyl, aralkyl, aryl, or a heterocyclic group;

A is a C 2 -C 20 alkyl;
with the proviso that any carbon-carbon double bonds in R or in R 1 through R 6 are essentially unreactive toward metathesis reactions with the catalyst.

2. The polymer of claim 1 , wherein the polymer comprising the repeating unit (Ib) or (Ic) is a cyclic polymer.

3. The polymer of claim 1 , wherein polymer comprising the repeating unit (Ib) or (Ic) is a block in a block copolymer.

4. A method of inhibiting microbial growth or inhibiting biofilm formation on a surface comprising the step of contacting one or more microbes with a polymer of claim 1 .

5. A method of preparing a therapeutic agent for delivery to a subject comprising combining the therapeutic agent with a polymer of claim 1 .

6. The method of claim 5 , wherein the therapeutic agent is conjugated to the polymer.

7. The method of claim 5 , wherein the therapeutic agent is contained in a micelle comprising the polymer.

Assignees

• Univ New York State Res Found

Inventors

• Sampson Nicole S
• Tan Li
• Parker Kathlyn

Classifications

• C08G2261/228

  Polymers, i.e. more than 10 repeat units · CPC title

• A61K47/48192

  Human Necessities · mapped topic

• C09D165/00

  Coating compositions based on macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain (C09D107/00 - C09D157/00, C09D161/00 take precedence); Coating compositions based on derivatives of such polymers · CPC title

• C08G2261/1424

  containing ether groups, including alkoxy · CPC title

• C08G2261/418

  Ring opening metathesis polymerisation [ROMP] · CPC title