Tagged polymers and methods of use

Patent metadata

Field	Value
Publication number	US-9238712-B2
Application number	US-201313827155-A
Country	US
Kind code	B2
Filing date	Mar 14, 2013
Priority date	Aug 2, 2012
Publication date	Jan 19, 2016
Grant date	Jan 19, 2016

Abstract

A polymer includes a monomeric repeat unit represented by Formula I:

In Formula I, R 1 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, or heterocyclyl; R 2 is alkyl, haloalkyl, alkenyl, alkynyl; R 3 is alkyl, OH, halo, or alkoxy; R 4 is alkyl, OH, halo, or alkoxy; Y is absent, C(O), C 1 -C 4 alkylidene, or C 1 -C 4 alkylideneamino; L is alkylidene, alkylidene-O-alkylidene, alkylidene-S-alkylidene, alkenylidene, cycloalkylidene, arylene, heteroarylene, C(O)O, or C(O)S; n1 is 0, 1, 2, 3, or 4; and n2 is 0, 1, 2, 3, or 4.

First claim

What is claimed is:

1. A polymer comprising a monomeric repeat unit represented by Formula I:

wherein:
R 1 is alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, or heterocyclyl;
R 2 is alkyl, haloalkyl, alkenyl, or alkynyl;
R 3 is alkyl, OH, halo, or alkoxy;
R 4 is alkyl, OH, halo, or alkoxy;
Y is absent, C(O), C 1 -C 4 alkylidene, or C 1 -C 4 alkylideneamino;
L is alkylidene, alkylidene-O-alkylidene, alkylidene-S-alkylidene, alkenylidene, cycloalkylidene, arylene, heteroarylene, C(O)O, or C(O)S;
n1 is 0, 1, 2, 3, or 4; and
n2 is 0, 1, 2, 3, or 4.

2. The polymer of claim 1 , wherein the monomeric repeat unit is represented by Formula IA:

wherein:
Z 1 is absent, CO, SO 2 , a residue derived from an acrylate, or a residue derived from an epoxide; and
Z 2 is absent, CO, SO 2 , a residue derived from an acrylate, or a residue derived from an epoxide.

3. The polymer of claim 1 , wherein the monomeric repeat unit is

4. The polymer of claim 1 , wherein the monomeric repeat unit is

5. The polymer of claim 1 , wherein R 1 is a chromophore, or fluorophore, or wherein R 1 contains a radioisotope.

6. The polymer of claim 1 , wherein R 4 is halo.

7. A polymer represented by Formula II:

wherein:
R 1 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, or heterocyclyl;
R 2 is alkyl;
R 5 , R 6 , R 7 , and R 8 are independently H or alkyl;
Y is absent, C(O), C 1 -C 4 alkylidene, or C 1 -C 4 alkylideneamino;
L is alkylidene, alkylidene-O-alkylidene, alkylidene-S-alkylidene, alkenylidene, cycloalkylidene, arylene, heteroarylene, C(O)O, or C(O)S; and
m, p, and q are independently an integer of 1 to 10,000.

8. The polymer of claim 7 , wherein the polymer is represented by Formula III:

9. The polymer of claim 7 , wherein R 5 , R 6 , R 7 , and R 8 are H.

10. The polymer of claim 7 , wherein L is —CH 2 CH 2 —.

11. The polymer of claim 7 , wherein Y is absent.

12. The polymer of claim 7 , wherein Y is C(O).

13. The polymer of claim 7 , wherein Y is —(C 1 -C 4 alkylidene)-N(C 1 -C 4 alkyl)-.

14. The polymer of claim 13 , wherein Y is —CH 2 CH 2 —N(CH 2 CH 3 )—.

15. The polymer of claim 7 , wherein R 1 is alkyl.

16. The polymer of claim 15 , wherein R 1 is 13 CH 3 .

17. The polymer of claim 7 , wherein R 1 is

18. The polymer of claim 7 , wherein R 1 is

19. The polymer of claim 7 , wherein R 1 is

20. A method of preparing a polymer, the method comprising:
contacting a compound of Formula IV with a compound of Formula V

to form a compound of Formula VI

and
contacting the compound of Formula VI with a linking compound to form the polymer, wherein the linking compound comprises OC(O)O, SO 2 , or an epoxide and the polymer comprises a monomeric repeat unit represented by Formula I

wherein:
R 1 is alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, or heterocyclyl;
R 2 is alkyl;
R 3 is alkyl, OH, halo, or alkoxy;
R 4 is alkyl, OH, halo, or alkoxy;
Y is absent, C(O), C 1 -C 4 alkylidene, or C 1 -C 4 alkylideneamino;
L is alkylidene, alkylidene-O-alkylidene, alkylidene-S-alkylidene, alkenylidene, cycloalkylidene, arylene, heteroarylene, C(O)O, or C(O)S;
n1 is 0, 1, 2, 3, or 4; and
n2 is 0, 1, 2, 3, or 4.

Assignees

• Empire Technology Dev Llc
• Empire Technology Developments LLC

Inventors

• Carlson William Brenden
• Phelan Gregory David
• Casasanta Iii Vincenzo

Classifications

• C08G65/42

  Phenols and polyhydroxy ethers · CPC title

• C08G2650/56

  Polyhydroxyethers, e.g. phenoxy resins · CPC title

• C08G65/38 Primary

  derived from phenols · CPC title

• C08G65/405

  in ring structure, e.g. phenolphtalein · CPC title

• C08G65/40

  from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group · CPC title