Sensing elements and methods for making and using same

• US 5,296,381 A
• Filed: 08/08/1991
• Issued: 03/22/1994
• Est. Priority Date: 08/08/1991
• Status: Expired due to Term

• Current Assignee: Terumo Cardiovascular Systems Corporation (Terumo Corporation)
• Original Assignee: Minnesota Mining and Manufacturing Co (3M Company)
• Inventors: Yan, Cheng, Carlock, John T., Korkowski, Paul F., Mader, Roger A., Yafuso, Masao
• Primary Examiner(s): Johnston, Jill A.
• Application Number:
  US07/742,002
• Time in Patent Office: 957 Days
• Field of Search: 436/68, 436/172, 422/55, 422/58, 422/57, 422/82.07, 422/82.08, 528/10, 528/15, 528/30-32, 528/43
• US Class Current: 436/172
• CPC Class Codes: A61B 5/1459 invasive, e.g. introduced into the body by a catheter A61B5/1464 takes precedence
• CPC Class Codes: G01N 2021/772 Tip coated light guide
• CPC Class Codes: G01N 2021/773 Porous polymer jacket; Polymer matrix with indicator
• CPC Class Codes: G01N 2021/7786 Fluorescence
• CPC Class Codes: G01N 21/7703 using reagent-clad optical fibres or optical waveguides using measurement of total internal reflection or attenuated total reflection G01N21/552; optical fibres or waveguides per se G02B

Abstract

A sensing element for sensing the concentration of an analyte in a medium is disclosed. The sensing element comprises a matrix material having at least one indicator component covalently bonded thereto. The indicator component is capable of providing a signal dependent on the concentration of a analyte in a medium. The indicator component is derived from at least one indicator compound having an aromatic ring to which is directly bonded a group including a functional portion which is conjugated relative to this aromatic ring.

Claims

1. A sensing element for sensing the concentration of an analyte in a medium comprising:

a matrix material having at least one indicator component covalently bonded thereto, said indicator component being capable of providing a signal dependent on the concentration of an analyte in a medium and being derived from at least one indicator compound having an aromatic ring to which is directly covalently bonded a group including a functional portion which is conjugated relative to said aromatic ring.

2. The sensing element of claim 1 wherein said at least one indicator compound is a polynuclear aromatic compound.

3. The sensing element of claim 2 wherein said polynuclear aromatic compound is selected from decacyclene, derivatives of decacylene, perylene, derivatives of perylene, benzo[ghi]perylene, derivatives of benzo[ghi]perylene, coronene, derivatives of coronene and mixtures thereof.

4. The sensing element of claim 1 wherein said functional portion is a multiple bond which includes an atom to which said aromatic ring is directly covalently bonded.

5. The sensing element of claim 4 wherein said group is a vinyl group.

6. The sensing element of claim 4 wherein said at least one indicator compound is selected from the group consisting of vinyl benzo[ghi]perylenes and mixtures thereof.

7. The sensing element of claim 1 wherein said functional portion is a carbon-carbon double bond.

8. The sensing element of claim 1 wherein said matrix material is a polymeric matrix material which is highly permeable to said analyte.

9. The sensing element of claim 8 wherein said polymeric matrix material is a silicone-based polymeric material.

10. The sensing element of claim 1 wherein said analyte is oxygen.

11. A method for sensing the concentration of an analyte in a medium comprising:

exposing a sensing element to said medium, said sensing element comprising a matrix material having at least one indicator component covalently bonded thereto, said indicator component being capable of providing a signal dependent on the concentration of said analyte in said medium and being derived from at least one indicator compound having an aromatic ring to which is directly covalently bonded a group including a functional portion which is conjugated relative to said aromatic ring;

causing said indicator component to provide said signal; and

analyzing said signal in determining the concentration of said analyte in said medium.

12. The method of claim 11 wherein said at least one indicator compound is a polynuclear aromatic compound.

13. The method of claim 12 wherein said polynuclear aromatic compound is selected from decacyclene, derivatives of decacylene, perylene, derivatives of perylene, benzo[ghi]perylene, derivatives of benzo[ghi]perylene, coronene, derivatives of coronene and mixtures thereof.

14. The method of claim 11 wherein said functional portion is a multiple bond which includes an atom to which said aromatic ring is directly covalently bonded.

15. The method of claim 14 wherein said functional portion is a carbon-carbon double bond.

16. The method of claim 14 wherein said group is a vinyl group.

17. The method of claim 14 wherein said at least one indicator compound is selected from the group consisting of vinyl benzo[ghi]perylenes and mixtures thereof.

18. The method of claim 11 wherein said matrix material is a polymeric matrix material which is highly permeable to said analyte.

19. The method of claim 18 wherein said polymeric matrix material is a silicone-based polymeric material.

20. The method of claim 11 wherein said analyte is oxygen.

21. A method for producing a sensing element useful for sensing the concentration of an analyte in a medium comprising:

contacting at least one precursor of an indicator component with a reactable material at conditions effective to form a matrix material having said indicator component covalently bonded thereto, said at least one precursor of said indicator component including an indicator compound having an aromatic ring to which is directly covalently bonded a group including a functional portion which is conjugated relative to said aromatic ring and which is capable of chemically reacting at said conditions, said covalently bonded indicator component being capable of providing a signal dependent on the concentration of said analyte in said medium.

22. The method of claim 21 wherein said indicator compound is a polynuclear aromatic compound.

23. The method of claim 21 wherein said polynuclear aromatic compound is selected from decacyclene, derivatives of decacylene, perylene, derivatives of perylene, benzo[ghi]perylene, derivatives of benzo[ghi]perylene, coronene, derivatives of coronene and mixtures thereof.

24. The method of claim 21 wherein said functional group is a multiple bond which includes an atom to which said aromatic ring is directly covalently bonded.

25. The method of claim 24 wherein said functional portion is a carbon-carbon double bond.

26. The method of claim 24 wherein said group is a vinyl group.

27. The method of claim 24 wherein said at least one precursor of said indicator component is selected from the group consisting of vinylbenzo[ghi]perylenes and mixtures thereof.

28. The method of claim 21 wherein said matrix material is a polymeric matrix material which is highly permeable to said analyte.

29. The method of claim 28 wherein said polymeric matrix material is a silicone-based polymeric material.

30. The method of claim 21 wherein said analyte is oxygen.

31. A method for producing a sensing element useful for sensing the concentration of an analyte in a medium comprising:

contacting a composition containing at least one precursor of an indicator component and at least one of a silicone-based polymer and a precursor of a silicone-based polymer at conditions effective to form a cross-linked, silicone-based polymeric matrix material having said indicator component covalently bonded thereto, said covalently bonded indicator component being capable of providing a signal dependent on the concentration of said analyte in said medium, said at least one precursor of said indicator component including an indicator compound having an aromatic ring to which is covalently bonded a group including a functional portion which is conjugated relative to said aromatic ring and which is capable of chemically reacting at said conditions.

32. The method of claim 31 wherein said at least one indicator compound is a polynuclear aromatic compound.

33. The method of claim 32 wherein said polynuclear aromatic compound is selected from decacyclene, derivatives of decacylene, perylene, derivatives of benzo[ghi]perylene, derivatives of benzo[ghi]perylene, coronene, derivatives of coronene and mixtures thereof.

34. The method of claim 31 where in said functional portion is a multiple bond which includes an atom to which said aromatic ring is directly covalently bonded.

35. The method of claim 34 wherein said functional portion is a carbon-carbon double bond.

36. The method of claim 34 wherein said group is a vinyl group.

37. The method of claim 34 wherein said at least one precursor of said indicator component is selected from the group consisting of vinyl benzo[ghi]perylene and mixtures thereof.

38. The method of claim 31 wherein said analyte is oxygen.

39. The method of claim 31 wherein said group includes a heteroatom.