IP Library Granted Patent US 7,229,836
Granted Patent B2
US 7,229,836 · App. 10/311,328 · Granted Jun 12, 2007

Polymers for binding of phenols

Assignee: The Horticulture and Food Research Institute of New Zealand Limited
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Quick Facts
Patent No.
US 7,229,836
App. No.
10/311,328
Granted
Jun 12, 2007
Kind
B2
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 polymerizing a polymerizable 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 (32)

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 said 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 claim 1 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 claim 1 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 sa claimed in claim 10 wherein the porous polymer membrane is a PTFE membrane.

12. A method as claimed in claim 1 wherein the phenol is substituted with 1 to 3 C 1 –C 3 alkyl groups.

13. A method as claimed in claim 12 where the phenol is substituted with 1 to 3 substituents selected from C 1 –C 6 alkyl, halogen, C 5 –C 6 alkoxy, C 1 –C 6 alkylthio, amino, C 1 –C 6 alkylamino, di(C 1 –C 3 alkyl) amino, —CONH 2 , —CN, carboxy, hydroxy, C 1 –C 6 alkylsulfonyl, nitro, and substituted C 1 –C 6 alkoxy or alkoxy wherein the substituent is selected from halogen, hydroxy, C 1 –C 3 alkoxy, amino, —CONH 2 , —CN and carboxy.

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

15. A sensor for detecting/measure propofol, comprising a probe having an imprinted polymer as defined in claim 1 .

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.

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.

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.

20. An imprinted polymer prepared by preparing or crosslinking a polymer in the presence of a phenol substituted with from 1 to 3 C 1 –C 6 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.

23. An imprinted polymer as claimed in claim 16 wherein the phenol is substituted with 1 to 3 C 1 –C 3 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 tire phenol is propofol.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 13, 2017
From: THE NEW ZEALAND INSTITUTE FOR PLANT AND FOOD RESEARCH LIMITED
To: LIGAR LIMITED PARTNERSHIP
Reel/Frame 044111/0351 →
AMALGAMATION Recorded Apr 30, 2009
From: THE HORTICULTURE AND FOOD RESEARCH INSTITUTE OF NEW ZEALAND LIMITED; NEW ZEALAND INSTITUTE FOR CROP AND FOOD RESEARCH LIMITED
To: THE NEW ZEALAND INSTITUTE FOR PLANT AND FOOD RESEARCH LIMITED
Reel/Frame 022619/0383 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 25, 2003
From: PETCU, MIRUNA; COONEY, JANINE; COOK, CHRISTIAN; LAUREN, DENIS
To: THE HORTICULTURE AND FOOD RESEARCH INSTITUTE OF NEW ZEALAND LIMITED
Reel/Frame 014207/0234 →
Priority Claims (1)
NZ 505525 · Jun 30, 2000 · national
Continuity (1)
Related Publication 20040096979A1 · May 20, 2004