IP Library Granted Patent US 12,295,369
Granted Patent B2
US 12,295,369 · App. 17/597,488 · Granted May 13, 2025

Articles containing a crosslinked guanidinyl-containing polymer and uses thereof

Inventors: Andrew W. Vail (Bayport, MN); Jerald K. Rasmussen (Woodville, WI); Robert A. Schmitz (St. Paul, MN)
Assignee: Solventum Intellectual Properties Company
A01N47/44A01N25/10A01N25/34
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Quick Facts
Patent No.
US 12,295,369
App. No.
17/597,488
Granted
May 13, 2025
Kind
B2
Abstract

An article, and method of use, wherein the article includes: a substrate; a cationic coating bound to the substrate, wherein the cationic coating includes a guanidinyl-containing polymer that is crosslinked on the substrate; wherein the guanidinyl-containing polymer is of the following Formula (I), wherein: R 3 is a H, C 1 -C 12 (hetero)alkyl, C 5 -C 12 (hetero)aryl, or Polymer; each R 4 is independently H, C 1 -C 12 (hetero)alkyl, or C 5 -C 12 (hetero)aryl; each R 5 is H, C 1 -C 12 (hetero)alkyl, C 5 -C 12 (hetero)aryl, or N(R 4 ) 2 ; Polymer is a residue of an aminopolymer chain; m is 1 or 2; and x is an integer of at least 1; and wherein the guanidinyl-containing polymer is crosslinked with an amine-reactive polyepoxy compound having pendant —OH groups.

Claims (23)

1. An article comprising:

a substrate;

a cationic coating bound to the substrate, wherein the cationic coating comprises a guanidinyl-containing polymer that is crosslinked on the substrate; wherein the guanidinyl-containing polymer is of the following Formula (I):

wherein: R 3 is a H, C 1 -C 12 (hetero) alkyl, C 5 -C 12 (hetero) aryl, or polymer;

each R 4 is independently H, C 1 -C 12 (hetero) alkyl, or C 5 -C 12 (hetero) aryl;

each R 5 is H, C 1 -C 12 (hetero) alkyl, C 5 -C 12 (hetero) aryl, or N(R 4 ) 2 ;

Polymer is a residue of an aminopolymer chain;

m is 1 or 2; and

x is an integer of at least 1; and

wherein the guanidinyl-containing polymer is crosslinked with an amine-reactive polyepoxy compound having pendant —OH groups,

wherein no more than 25 mol-% of the amino groups of a polyethyleneimine precursor are functionalized with guanidinyl groups such that the guanidinyl polymer reduces washoff of the cationic coating from the substrate.

2. The article of claim 1 , wherein the guanidinyl-containing polymer is crosslinked by reaction of at least 5 mol-% of amino groups of the aminopolymer precursor with the amine-reactive polyepoxy compound having pendant —OH groups.

3. The article of claim 1 , wherein the amine-reactive polyepoxy compound having pendant —OH groups is selected from the group of glycerol diglycidyl ether, sorbitol diglycidyl ether, diglycerol diglycidyl ether, diglycerol triglycidyl ether, pentaerythritol diglycidyl ether, pentaerythritol triglycidyl ether, trimethylol propane diglycidyl ether, trimethylol ethane diglycidyl ether, and combinations thereof.

4. The article of claim 1 , wherein the amine-reactive polyepoxy compound having pendant-OH groups is glycerol diglycidyl ether.

5. The article of claim 1 , wherein at least 0.1 mole percent of amino groups of the aminopolymer precursor are functionalized with guanidinyl groups.

6. The article of claim 1 , wherein up to 95 mol-% of amino groups of the aminopolymer precursor are functionalized with guanidinyl groups.

7. The article of claim 1 , wherein the aminopolymer precursor is selected from the group of polyaminoamide, polyamidoamine, polyethylenimine, polypropylenimine, polyvinylamine, polyallylamine, polydiallylamine, and mixtures thereof.

8. The article of claim 1 , wherein the aminopolymer precursor is polyethylenimine.

9. The article of claim 1 , wherein the substrate is formed of a material selected from poly(meth)acrylates, poly(meth)acrylamides, polyolefins, poly(isoprenes), poly(butadienes), fluorinated polymers, chlorinated polymers, poly(esters), polyamides, polyimides, polyethers, poly(ether sulfones), poly(sulfones), poly(vinyl acetates), copolymers of vinyl acetate, poly(phosphazenes), poly(vinyl esters), poly(vinyl ethers), poly(vinyl alcohols), poly(carbonates), polyurethanes, cellulosic materials, and combinations thereof.

10. The article of claim 1 , wherein the substrate is porous.

11. The article of claim 10 , wherein the cationic coating is disposed on a surface of the substrate, distributed throughout at least a portion of the substrate, or both.

12. The article of claim 1 , wherein the article is a wipe.

13. A method of removing a contaminant from a contaminated surface, the method comprising contacting the article of claim 1 , in the presence of a liquid, with an area of the contaminated surface, wherein the contaminated surface is a solid surface.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 1, 2024
From: 3M INNOVATIVE PROPERTIES COMPANY
To: SOLVENTUM INTELLECTUAL PROPERTIES COMPANY
Reel/Frame 066430/0149 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 12, 2022
From: VAIL, ANDREW W.; RASMUSSEN, JERALD K.; SCHMITZ, ROBERT A.
To: 3M INNOVATIVE PROPERTIES COMPANY
Reel/Frame 058632/0346 →
Continuity (2)
Provisional Application 62883725 · Aug 7, 2019
Related Publication 20220279791A1 · Sep 8, 2022
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