# US 11,299,591 B2 · Polyethyleneimine compounds containing N-halamine and derivatives thereof

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- Number: US 11,299,591 B2
- Document ID: US11299591B2
- Status: Granted
- Kind: B2
- Application number: 16/590,655
- Filed: 2019-10-02
- Published: 2020-04-23
- Granted: 2022-04-12
- Earliest claimed: 2018-10-18
- Assignees: Milliken & Company
- Applicants: Milliken & Company
- Inventors: Sudhanshu Srivastava; Wesley A. Freund; Sanjeev K. Dey; Dominick J. Valenti
- Web page: https://patentgrep.com/patent/US11299591B2

## CPC

- C08G 18/7621: {being toluene diisocyanate including isomer mixtures}
- C08G 73/0206: {Polyalkylene(poly)amines}
- C08G 18/165: {covered by C08G18/18 and C08G18/24}
- C08G 18/18: containing secondary or tertiary amines or salts thereof
- C08G 18/2081: {containing at least two non-condensed heterocyclic rings}
- C08G 18/244: {tin salts of carboxylic acids}
- C08G 18/302: {Water}
- C08G 18/4829: {Polyethers containing at least three hydroxy groups (C08G18/4833 - C08G18/5096 take precedence)}
- C08G 73/024: {Polyamines containing oxygen in the form of ether bonds in the main chain}
- C08J 9/0061: {characterized by the use of several polymeric components}
- C08L 75/04: Polyurethanes
- D06M 15/61: Polyamines {polyimines}
- D06M 16/00: Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
- C08G 2101/00: Manufacture of cellular products
- C08J 2375/04: Polyurethanes
- C08J 2479/02: Polyamines
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- D06M: TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS

## Abstract

This invention relates to odor control molecules comprised of polyethyleneimine compounds containing N-halamine and derivatives thereof.

## Claims

### Claim 1

An article comprising:
(a) at least one thermoset polyurethane foam material, and
(b) a polyethyleneimine compound comprising a plurality of amine groups, each amine group comprising a nitrogen atom, wherein:
i. at least one amine group comprises a nitrogen atom directly bonded to a functional group selected from the group consisting of alkanoyl groups, alkenoyl groups, aroyl groups, alkyl groups containing three or more carbon atoms, and aryl groups, and
ii. at least one amine group comprises a nitrogen atom directly bonded to a halogen.

### Claim 2 (depends on 1)

The article of claim 1, wherein the polyethyleneimine compound further contains at least one polyalkyleneoxy chain.

### Claim 3 (depends on 2)

The article of claim 2, wherein the at least one polyalkyleneoxy chain is a polymeric epoxide.

### Claim 4 (depends on 3)

The article of claim 3, wherein the polymeric epoxide is selected from the group consisting of polyethylene oxides; polypropylene oxides; polybutylene oxides; oxetanes;
tetrahydrafurans; copolymers of polyethylene oxides, polypropylene oxides and polybutylene oxides; and other copolymers including block copolymers, in which a majority of the polymeric substituent is polyethylene oxide, polypropylene oxide and/or polybutylene oxide.

### Claim 5 (depends on 1)

The article of claim 1, wherein the halogen is selected from the group consisting of chlorine, bromine, fluorine, and iodine.

### Claim 6 (depends on 5)

The article of claim 5, wherein the halogen is chlorine.

### Claim 7 (depends on 1)

The article of claim 1, wherein the polyethyleneimine compound is linear or branched.

### Claim 8 (depends on 1)

The article of claim 1, wherein the functional group is selected from the group consisting of C10-C26 alkanoyl groups, C10-C26 alkenoyl groups, aroyl groups, C10-C26 alkyl groups and aryl groups.

### Claim 9 (depends on 1)

The article of claim 1, wherein the polyethyleneimine compound has a molecular weight in a range from 400 to 50,000.

### Claim 10

An article comprising:
(a) at least one thermoset polyurethane foam material;
(b) a polyethyleneimine compound comprising a plurality of amine groups, each amine group comprising a nitrogen atom, wherein:
i. at least one amine group comprises a nitrogen atom directly bonded to a functional group selected from the group consisting of alkanoyl groups, alkenoyl groups, aroyl groups, alkyl groups containing three or more carbon atoms, and aryl groups, and
ii. at least one amine group comprises a nitrogen atom directly bonded to a halogen; and
(c) a polyethyleneimine compound comprising a plurality of amine groups, each amine group comprising a nitrogen atom, wherein:
i. at least one amine group comprises a nitrogen atom directly bonded to at least one alkyleneoxy group, and
ii. at least one amine group comprises a nitrogen atom directly bonded to a halogen.

### Claim 11 (depends on 10)

The article of claim 10, wherein the at least one alkyleneoxy group is a group of Formula (C):
wherein each R101 and R102 group is independently selected from the group consisting of hydrogen, alkyl, aryl, alkoxyalkyl, and aryloxyalkyl; wherein a is an integer equal to or greater than 1; and wherein R105 is selected from the group consisting of hydrogen, alkyl groups, and aryl groups.

### Claim 12 (depends on 10)

The article of claim 10, wherein the halogen is selected from the group consisting of chlorine, bromine, fluorine, and iodine.

### Claim 13 (depends on 12)

The article of claim 12, wherein the halogen is chlorine.

### Claim 14 (depends on 10)

The article of claim 10, wherein the polyethyleneimine compound is linear or branched.

### Claim 15 (depends on 10)

The article of claim 10, wherein the functional group is selected from the group consisting of C10-C26 alkanoyl groups, C10-C 26 alkenoyl groups, aroyl groups, C10-C26 alkyl groups and aryl groups.

### Claim 16 (depends on 10)

The article of claim 10, wherein the polyethyleneimine compound has a molecular weight in a range from 400 to 50,000.