Polymers for binding of phenols

• US 20040096979A1
• Filed: 06/25/2003
• Published: 05/20/2004
• Est. Priority Date: 06/30/2000
• Status: Active Grant

• Current Assignee: Ligar Limited Partnership
• Original Assignee: The Horticulture And Food Research Institute Of New Zealand Limited
• Inventors: Lauren, Denis Richard, Petcu, Miruna, Cooney, Janine, Cook, Christian
• Granted Patent: US 7,229,836 B2
• Time in Patent Office: Days
• US Class Current: 436/131
• CPC Class Codes: C08F 218/24 Esters of carbonic or haloformic acids, e.g. allyl carbonate
• CPC Class Codes: C08F 222/102 of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
• CPC Class Codes: C08F 2810/20 leading to a crosslinking, either explicitly or inherently
• CPC Class Codes: C08F 2810/50 wherein the polymer is a copolymer and the modification is taking place only on one or more of the monomers present in minority
• CPC Class Codes: C08F 8/12 Hydrolysis
• CPC Class Codes: G01N 2600/00 Assays involving molecular imprinted polymers/polymers created around a molecular template
• CPC Class Codes: G01N 33/5308 for analytes not provided for elsewhere, e.g. nucleic acids, uric acid, worms, mites
• CPC Class Codes: G01N 33/9406 Neurotransmitters
• CPC Class Codes: Y10T 436/20 Oxygen containing
• CPC Class Codes: Y10T 436/203332 Hydroxyl containing

Abstract

The invention relates to a method for the detection and/or measurement of a phenol comprising: (a) contacting the sample to be tested with a polymer imprinted with the phenol or an analogue thereof; and (b) measuring binding of the phenol to the polymer. The polymer may be prepared by polymerising a polymerisable monomer, to which a phenol is covalently bound by a hydrolysable linker, and subsequently removing the phenol by hydrolysis. Propofol is a preferred phenol for use in the invention.

Claims

18. An imprinted polymer prepared by polymerising a polymerisable monomer, to which a phenol is covalently bound by a hydrolysable linker, and subsequently removing the phenol by hydrolysis.

1. A method for the detection and/or measurement of a phenol comprising:

(a) contacting the sample to be tested with a polymer imprinted with the phenol or an analogue thereof;

(b) measuring binding of the phenol to the polymer.

2. A method as claimed in claim 1 wherein said imprinted polymer was prepared by polymerising a polymerisable monomer, to which a phenol is covalently bound by a hydrolysable linker, and subsequently removing the phenol by hydrolysis.

3. A method as claimed in claim 2 wherein said monomer has the formula MXP wherein;

P is a (substituted) phenoxy group;

M is a polymerisable group containing an alkenyl group;

X is a bond or a linker group susceptible to hydrolysis under conditions which do not result in destruction of the polymer backbone.

4. A method as claimed in claim 3 wherein X or X together with M and/or P contains an —

O—

CO—

O—

group.

5. A method as claimed in claim 4 wherein M is a vinylphenyl group, and X and the oxy group of P form an —

O—

CO—

O—

group.

6. A method as claimed in claim 1 wherein aid imprinted polymer was prepared by preparing or crosslinking a polymer in the presence of the phenol, with subsequent removal of phenol.

7. A method as claimed in claim 6 wherein the polymer is a crosslinked polyacrylate or polymethacrylate.

8. A method as claimed in claim 7 wherein the polymer is a polymethacrylate crosslinked with ethylenedimethacrylate.

9. A method as claimed in any preceding claim wherein the particle size of at least 50% (by weight) of the polymer is in the range 0.5-5 microns.

10. A method according to any preceding claim wherein the imprinted polymer is formed by placing the polymerisation mixture on a porous polymer membrane and allowing the mixture to polymerise.

11. A method as claimed in claim 10 wherein the porous polymer membrane is a PTFE membrane.

12. A method as claimed in any one of the preceding claims wherein the phenol is phenol or is a mono- di- or tri-substituted phenol.

13. A method as claimed in claim 12 where the phenol is substituted with 1 to 3 substituents selected from C₁-C₆ alkyl, halogen, C₁-C₆ alkoxy, C₁-C₆ alkylthio, amino, C₁-C₆ alkylamino, di(C₁-C₃ alkyl) amino, —

CONH₂, —

CN, carboxy, hydroxy, C₁-C₆ alkylsulfonyl, nitro, and substituted C₁-C₆ alkyl or alkoxy wherein the substituent is selected from halogen, hydroxy, C₁-C₃ alkoxy, amino, —

CONH₂, —

CN and carboxy.

14. A method as claimed in claim 13 wherein the phenol is substituted with 1 to 3 C₁-C₃ alkyl groups.

15. A method as claimed in claim 14 wherein the phenol is propofol or a cresol.

16. A method as claimed in claim 15 wherein the phenol is propofol.

17. A sensor for detecting/measure propofol, comprising a probe having an imprinted polymer as defined in any previous claim.

19. An imprinted polymer as claimed in claim 18 wherein said monomer has the formula MXP and wherein;

P is a (substituted) phenoxy group;

M is a polymerisable group containing an alkenyl group;

23. An imprinted polymer as claimed in ane one of claims 16-22 wherein the phenol is substituted with 1 to 3 C₁-C₃ alkyl groups.

24. An imprinted polymer as claimed in claim 23 wherein the phenol is propofol or a cresol.

25. An imprinted polymer as claimed in claim 24 wherein the phenol is propofol.

19-1. An imprintedpolymer as claimed in claim 18 wherein M is a vinylphenyl group, and X and the oxy group of P form an —

O—

CO—

O—

group.

20. An imprinted polymer prepared by preparing or crosslinking a polymer in the presence of a phenol substituted with from 1 to 3 C₁-C₆ alkyl groups and subsequently chemically or physically removing the substituted phenol.

21. An imprinted polymer as claimed in claim 20 wherein the polymer is a crosslinked polyacrylate or polymethacrylate.

22. An imprinted polymer as claimed in claim 21 wherein the polymer is a polymethacrylate crosslinked with ethylenedimethacrylate.