Process for preparing guanidino-functional monomers

Patent metadata

Field	Value
Publication number	US-2017183299-A1
Application number	US-201715459475-A
Country	US
Kind code	A1
Filing date	Mar 15, 2017
Priority date	Jun 17, 2013
Publication date	Jun 29, 2017
Grant date	—

Abstract

A process for preparing guanidino-functional, free radically polymerizable compounds comprises (a) combining (1) an amine compound comprising (i) at least one primary aliphatic amino group and (ii) at least one secondary aliphatic amino group, primary aromatic amino group, or secondary aromatic amino group, and (2) a guanylating agent; (b) allowing or inducing reaction of the amine compound and the guanylating agent to form a guanylated amine compound; (c) combining (1) the guanylated amine compound, and (2) a reactive monomer comprising (i) at least one ethylenically unsaturated group and (ii) at least one group that is reactive with an amino group; and (d) allowing or inducing reaction of the guanylated amine compound and the reactive monomer to form a guanidino-functional, free radically polymerizable compound.

First claim

We claim:

1 . A guanidino-functional, free radically polymerizable compound represented by the following general formula
CH 2 ═CHR 1 —C(═O)—O—R 5 —NH—C(═O)—NR 4 —R 2 —NH—C(═NR 3 )—N(R 3 ) 2   (I)
wherein
R 1 is selected from hydrogen, alkyl, aryl, and combinations thereof;
R 2 is selected from hydrocarbylene, heterohydrocarbylene, and combinations thereof;
each R 3 is independently selected from hydrogen, hydrocarbyl, heterohydrocarbyl, and combinations thereof;
R 4 is selected from hydrogen, hydrocarbyl, heterohydrocarbyl, and combinations thereof;
R 5 is selected from hydrocarbylene, heterohydrocarbylene, and combinations thereof;
with the proviso that R 2 and/or R 4 comprise(s) at least one aromatic moiety.

2 . A polymer comprising polymerized units of at least one compound of claim 1 .

3 . An article comprising a substrate bearing the polymer of claim 2 .

4 . The article of claim 3 , wherein the substrate is a microporous membrane.

5 . The article of claim 3 , wherein the polymer is grafted to the substrate.

6 . The article of claim 3 , wherein said article comprises at least one filter element.

7 . A method of capture or removal of a target biological species comprising
(a) providing at least one article of claim 6 ; and (b) allowing a moving biological solution containing a target biological species to impinge upon the upstream surface of said filter element for a time sufficient to effect binding of said target biological species.

8 . The compound of claim 1 , wherein R 1 is hydrogen or methyl.

9 . The compound of claim 1 , wherein R 2 is alkylene or aralkylene.

10 . The compound of claim 9 , wherein R 2 is ethylene, propylene, phenethylene, or benzylene.

11 . The compound of claim 1 , wherein R 3 is independently selected from hydrogen, isopropyl, or cyclohexyl.

12 . The compound of claim 11 , wherein R 3 is hydrogen.

13 . The compound of claim 1 , wherein R 4 is hydrogen, alkyl, aralkyl, aryl, or guanidino-substituted alkyl and combinations thereof.

14 . The compound of claim 13 , wherein R 4 is aralkyl or aryl.

15 . The compound of claim 13 , wherein R 4 is hydrogen, alkyl, aralkyl, aryl, or —R 2 —NH—C(═NR 3 )—N(R 3 ) 2 and combinations thereof.

16 . The compound of claim 1 , wherein R 3 is hydrogen, and R 4 is hydrogen, alkyl, aralkyl, aryl, or —R 2 —NH—C(═NR 3 )—N(R 3 ) 2 and combinations thereof.

17 . The compound of claim 1 , wherein R 5 is propylene or ethylene.

18 . The compound of claim 1 , wherein R 3 is hydrogen, and R 4 is benzyl or phenyl.

19 . The compound of claim 1 , wherein R 1 is hydrogen or alkyl, R 2 is alkylene, R 3 is hydrogen, and R 4 is benzyl or phenyl.

Assignees

• 3M Innovative Properties Co

Inventors

• Rasmussen Jerald K
• Griesgraber George W
• Hembre James I

Classifications

• C07C279/12

  being further substituted by nitrogen atoms not being part of nitro or nitroso groups · CPC title

• C07C277/08 Primary

  of substituted guanidines · CPC title

• C09D4/00

  Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16} · CPC title

• B01J20/327

  Polymers obtained by reactions involving only carbon to carbon unsaturated bonds · CPC title

• G01N1/405

  by adsorption or absorption · CPC title