# US 2014/0155555 A1 · Molecularly Imprinted Polymers Selective for Tobacco Specific Nitrosamines and Methods of Using Same

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- Number: US 2014/0155555 A1
- Document ID: US20140155555A1
- Status: Published application
- Kind: A1
- Application number: 14/175,885
- Filed: 2014-02-07
- Published: 2014-06-05
- Earliest claimed: 2006-12-07
- Assignees: British American Tobacco (Investments) Limited
- Applicants: British American Tobacco (Investments) Limited
- Inventors: Anthony Rees; Johan Billing; Ecevit Yilmaz
- Web page: https://patentgrep.com/patent/US20140155555A1

## CPC

- C08F 222/102: {of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate}
- A24B 15/245: {Nitrosamines}
- A24B 15/30: by organic substances {(A24B15/281 takes precedence)}
- A24B 15/32: by acyclic compounds
- A24D 3/14: of organic materials as additive (of ion exchange materials A24D3/12)
- B01D 15/3852: {using imprinted phases or molecular recognition}
- B01J 20/268: {Polymers created by use of a template, e.g. molecularly imprinted polymers}
- C08F 220/68: Esters
- C08F 222/104: {of tetraalcohols, e.g. pentaerythritol tetra(meth)acrylate}
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- A24B: MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24D: CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES OF CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
- B01D: SEPARATION (separating solids from solids by wet methods B03B, B03D; by pneumatic jigs or tables B03B; by other dry methods B07; magnetic or electrostatic separation of solid materials from solid materials or fluids, separation by high-voltage electric fields B03C; centrifuges, vortex apparatus B04; presses per se for squeezing-out liquid from liquid-containing material B30B9/02; treatment of water C02F, e.g. softening by ion-exchange C02F1/42; {arrangements of air intake cleaners in gas turbine plants F02C7/05} ; arrangements or mounting of filters in air-conditioning, air-humidification or ventilation F24F13/28)
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS

## Abstract

A class of molecularly imprinted polymers that specifically recognizes and binds to TSNAs are useful, for example, in analysis and separation of TSNAs from biological fluids. Such polymers are also useful in methods of treating and manufacturing tobacco products and materials.

## Claims

### Claim 1

A molecularly imprinted polymer selective for at least one tobacco specific nitrosamine (TSNA), the polymer having been prepared using materials comprising:
a TSA or a structural analogue thereof;
a neutral functional monomer; and
a hydrophobic cross-linker.

### Claim 2 (depends on 1)

A polymer according to claim 1, wherein said structural analogue of a TSNA is an enamine analogue of a TSNA.

### Claim 3 (depends on 1)

A polymer according to claim 1, wherein said structural analogue of a TSNA is an amide analogue of a TSNA.

### Claim 4 (depends on 1)

A polymer according to claim 1, wherein said structural analogue of a TSNA is a sulfonamide analogue of a TSNA.

### Claim 5 (depends on 1)

A polymer according to claim 1, wherein said neutral functional monomer is selected from the group consisting of 2-hydroxyethylmethacrylate (HEMA), acrylamide, methacrylamide, glycerol monoacrylate, and glycerol monomethacrylate.

### Claim 6 (depends on 1)

A polymer according to claim 1, wherein said hydrophobic cross-linker is selected from the group consisting of ethylene glycol dimethacrylate (EDMA), trimethylolpropane trimethacrylate (TRIM), and divinylbenzene (DVB).

### Claim 7 (depends on 1)

A polymer according to claim 1, wherein the polymer is selective for NNK.

### Claim 8 (depends on 1)

A polymer according to claim 1, wherein the polymer is selective for NNA.

### Claim 9 (depends on 1)

A polymer according to claim 1, wherein the polymer is selective for NNN.

### Claim 10 (depends on 1)

A polymer according to claim 1, wherein the polymer is selective for NAB.

### Claim 11 (depends on 1)

A polymer according to claim 1, wherein the polymer is selective for NAT.

### Claim 12 (depends on 1)

A polymer according to claim 1, wherein the polymer is selective for NNAL.

### Claim 13 (depends on 1)

A polymer according to claim 1, wherein the polymer is selective for iso-NNAL.

### Claim 14 (depends on 1)

A polymer according to claim 1, wherein the polymer is selective for iso-NNAC.

### Claim at position 15

15-16. (canceled)

### Claim 17

A kit, comprising:
a molecularly imprinted polymer selective for at least one tobacco specific nitrosamine (TSNA), the polymer prepared using materials comprising:
a TSNA or a structural analogue thereof;
a neutral functional monomer selected from the group consisting of 2-hydroxyethylmethacrylate (HEMA), acrylamide, methacrylamide, glycerol monoacrylate, and glycerol monomethacrylate;
a hydrophobic cross-linker selected from the group consisting of ethylene glycol dimethacrylate (EDMA), trimethlyolpropane trimethacrylate (TRIM), and divinylbenzene (DVB); and
instructions for using the molecularly imprinted polymer to perform at least one of detecting, quantifying, and separating nitrosamines in a sample.

### Claim 18

A method of preparing a molecularly imprinted polymer selective for TSNAs, comprising:
co-polymerizing at least one neutral functional monomer and at least one hydrophobic cross-linker in the presence of at least one TSNA structural analogue in a polymerization medium containing at least one free radical initiator to produce a molecularly imprinted polymer bound to a TSNA structural analogue; and
removing the TSNA structural analogue from the molecularly imprinted polymer.

### Claim 19 (depends on 18)

A method according to claim 18, wherein the functional monomer is selected from the group consisting of: HEMA, acrylamide, methacrylamide, glycerol monoacrylate, and glycerol monomethacrylate.

### Claim 20 (depends on 18)

A method according to claim 18, wherein the cross-linker is selected from the group consisting of: EDMA, TRIM, and DVB.

### Claim 21 (depends on 18)

A molecularly imprinted polymer produced by the method of claim 18.

### Claim at position 21

22-27. (canceled)
