Substrates and compounds bonded thereto

• US 20050142296A1
• Filed: 07/22/2004
• Published: 06/30/2005
• Est. Priority Date: 12/30/2003
• Status: Active Grant

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Lakshmi, Brinda B.
• Granted Patent: US 7,658,994 B2
• Time in Patent Office: Days
• US Class Current: 427/301
• CPC Class Codes: G01N 33/54353 with ligand attached to the carrier via a chemical coupling agent coatings G01N33/54393
• CPC Class Codes: Y10T 428/249953 Composite having voids in a component [e.g., porous, cellular, etc.]
• CPC Class Codes: Y10T 428/28 Web or sheet containing structurally defined element or component and having an adhesive outermost layer
• CPC Class Codes: Y10T 428/2804 Next to metal
• CPC Class Codes: Y10T 428/2852 Adhesive compositions

Abstract

Articles and methods for the use of such articles are described for use in immobilizing nucleophile-containing materials. In one aspect, the invention provides an article comprising: a substrate having a first surface and a second surface; and a phosphonitrilic tethering group affixed to the first surface of the substrate, the phosphonitrilic tethering group comprising a reaction product of a complementary functional group on the first surface of the substrate with a phosphonitrilic tethering compound. A method of immobilizing a nucleophile-containing material to a substrate is also described, the method comprising: providing a phosphonitrilic tethering compound; providing a substrate having a complementary functional group capable of reacting with phosphonitrilic tethering compound; preparing a substrate-attached phosphonitrilic tethering group by reacting the phosphonitrilic tethering compound with the complementary functional group on the substrate resulting in an ionic bond, covalent bond, or combinations thereof; and reacting the substrate-attached phosphonitrilic tethering group with a nucleophile-containing material to immobilize the nucleophile-containing material.

Claims

22. A method of immobilizing a nucleophile-containing material to a substrate, the method comprising:

Providing a phosphonitrilic tethering compound;

Providing a substrate having a functional group capable of reacting with the phosphonitrilic tethering compound;

Preparing a substrate-attached phosphonitrilic tethering group by reacting the phosphonitrilic tethering compound with the functional group on the substrate resulting in an ionic bond, covalent bond, or combinations thereof; and

Reacting the substrate-attached phosphonitrilic tethering group with a nucleophile-containing material to immobilize the nucleophile-containing material.

1. An article comprising:

a substrate having a first surface and a second surface;

a phosphonitrilic tethering group attached to the first surface of the substrate, the phosphonitrilic tethering group comprising a reaction product of a functional group on the first surface of the substrate with a phosphonitrilic tethering compound.

2. The article according to claim 1 wherein the first surface of the substrate comprises diamond-like glass.

3. The article according to claim 2 wherein the diamond-like glass comprises at least 30 weight percent carbon, at least 25 weight percent silicon, and up to 45 weight percent oxygen.

4. The article according to claim 1 wherein the substrate is a multilayered construction comprising first and second layers, the first layer comprising a polymer and the second layer comprising diamond-like glass.

5. The article according to claim 4 wherein the polymer comprises a microporous structure comprising pores having a pore diameter within the range from about 80 nm to about 0.5 micrometer.

6. The article according to claim 4 wherein the polymer comprises a thermally induced phase separated membrane comprising a material selected from the group consisting of high density polyethylene, polypropylene, polyvinylidenefluoride, polyethylene-vinyl alcohol copolymer and combinations of two or more of the foregoing.

7. The article according to claim 6 wherein the thermally induced phase separated membrane comprises high density polyethylene comprising a plurality of pores having a pore size between about 0.5 micrometer and 0.0229 mm.

8. The article according to claim 7 wherein the diamond like glass is coated on the thermally induced phase separated membrane, the diamond-like glass extending into the pores of the thermally induced phase separated membrane.

9. The article according to claim 1 wherein the substrate is a multilayered construction comprising first, second and third layers, the first layer comprising a polymer, the second layer comprising diamond-like carbon and the third layer comprising diamond-like glass affixed to the diamond-like carbon.

10. The article according to claim 9 wherein the polymer is polyimide.

11. The article according to claim 1 wherein the substrate is a multilayered construction comprising first and second layers, the first layer comprising glass and the second layer comprising diamond-like glass affixed to the glass.

12. The article according to claim 1 wherein the substrate comprises metal or metal oxide.

13. The article according to claim 1, wherein the substrate comprises metal or metal oxide selected from the group consisting of gold, silver, titanium, platinum, palladium, aluminum, copper, chromium, iron, cobalt, nickel, zinc, stainless steel, indium tin oxide, and combinations of two or more of the foregoing.

14. The article according to claim 12, wherein the substrate further comprises a support layer supporting the metal.

15. The article according to claim 14, wherein the support layer comprises a polymer.

16. The article according to claim 1 wherein the phosphonitrilic tethering compound comprises a structure according to Formula I

17. The article according to claim 16 wherein the first surface of the substrate comprises diamond-like glass having a complementary functional group capable of reacting with an X group of Formula I.

18. The article according to claim 17 wherein the complementary functional group is an aminosilane of the formula —

Si(OR¹)_3-n[(R²)NH₂]_n where n is an integer of 0 to 2 and R¹ is an alkyl having a carbon chain length less than 5, R² is another alkyl group having a carbon chain length of at least 2.

19. The article according to claim 17 wherein the complementary functional group is an aminosilane selected from the group consisting of 3-aminopropyl triethoxysilane, 3-amino trimethoxy silane, and combinations of the foregoing.

20. The article according to claim 16 wherein each X is chlorine.

21. The article according to claim 1 further comprising a monofunctional, difunctional, or multifunctional moiety affixed to the phosphonitrilic tethering group.

23. The method of claim 22 wherein providing the phosphonitrilic tethering compound comprises providing a compound of the Formula I

24. The method of claim 23 wherein each X is chlorine.

25. The method of claim 22 wherein providing a substrate having a functional group capable of reacting with a phosphonitrilic tethering compound comprises providing a substrate having a first surface and a second surface, the first surface comprised of diamond-like glass.

26. The method of claim 25 wherein the diamond-like glass comprises at least 30 weight percent carbon, at least 25 weight percent silicon, and up to 45 weight percent oxygen.

27. The method of claim 22 wherein the substrate is a multilayered construction comprising first and second layers, the first layer comprising a polymer and the second layer comprising diamond-like glass affixed to the polymer.

28. The method of claim 27 wherein the polymer comprises a thermally induced phase separated membrane comprising material selected from the group consisting of high density polyethylene, polypropylene, polyvinylidenefluoride, polyethylene-vinyl alcohol copolymer and combinations of two or more of the foregoing.

29. The method of claim 28 wherein the thermally induced phase separated membrane comprises high density polyethylene having a plurality of pores therein, the pore size being between about 0.5 micrometer and 0.0229 mm.

30. The method of claim 22 wherein the substrate is a multilayered construction comprising first, second and third layers, the first layer comprising a polymer, the second layer comprising diamond-like carbon and the third layer comprising diamond-like glass.

31. The method of claim 30 wherein the polymer is a polyimide.

32. The method of claim 22 wherein the substrate is a multilayered construction comprising first and second layers, the first layer comprising glass and the second layer comprising diamond-like glass affixed to the glass.

33. The method of claim 22 wherein providing a substrate having a complementary functional group capable of reacting with a phosphonitrilic tethering compound comprises providing a substrate having a first surface and a second surface, the first surface comprised of metal or metal oxide.

34. The method of claim 22, wherein the substrate comprises a metal or metal oxide selected from the group consisting of gold, silver, titanium, platinum, palladium, aluminum, copper, chromium, iron, cobalt, nickel, zinc, stainless steel, indium tin oxide, and combinations of two or more of the foregoing.

35. The method of claim 34, wherein the substrate further comprises a support layer supporting the metal.

36. The method of claim 35, wherein the support layer comprises a polymer.

37. The method of claim 22 wherein reacting the substrate-attached phosphonitrilic tethering group with a nucleophile-containing material to immobilize the nucleophile-containing material comprises reacting the phosphonitrilic tethering group to a nucleophile-containing material selected from amine-containing analyte, amino acid, peptide, DNA, RNA, protein, enzyme, organelle, immunoglobulin, and fragments and combinations of two or more of the foregoing.

38. The method of claim 22, wherein reacting the substrate-attached phosphonitrilic tethering group with a nucleophile-containing material to immobilize the nucleophile-containing material comprises reacting the phosphonitrilic tethering group to an amine-containing material.

39. The method of claim 38, wherein the amine-containing material is an antigen and the antigen is further bound to an antibody.

40. The method of claim 39, wherein the amine-containing material is an immunoglobulin.

41. The method of claim 38, wherein the amine-containing material is further bound to a bacterium.

42. The method of claim 41, wherein the bacterium is Staphylococcus aureus.

43. The method of claim 22 wherein the substrate-attached phosphonitrilic tethering group further comprises a monofunctional, difunctional, or multifunctional moiety affixed to the phosphonitrilic tethering group.

44. The method of claim 22 wherein the substrate-attached phosphonitrilic tethering group further comprises a first phosphonitrilic affixed to the substrate, a difunctional or multifunctional group affixed to the first phosphonitrilic group and a second phosphonitrilic group affixed to the difunctional or multifunctional group, the difunctional or multifunctional group forming a linking group between the first and second phosphonitrilic groups.

45. The method of claim 44 wherein reacting the substrate-attached phosphonitrilic tethering group with a nucleophile-containing material to immobilize the nucleophile-containing material comprises reacting the second phosphonitrilic group to the nucleophile-containing material.

46. The method of claim 45 wherein the nucleophile-containing material is selected from amine-containing analyte, amino acid, peptide, DNA, RNA, protein, enzyme, organelle, immunoglobulin, and fragments and combinations of two or more of the foregoing.

47. The method of claim 45, wherein reacting the substrate-attached phosphonitrilic tethering group with a nucleophile-containing material to immobilize the nucleophile-containing material comprises reacting the phosphonitrilic tethering group to an amine-containing material.

48. The method of claim 47, wherein the amine-containing material is an antigen and the antigen is further bound to an antibody.

49. The method of claim 47, wherein the amine-containing material is further bound to a bacterium.

50. The method of claim 49, wherein the bacterium is Staphylococcus aureus.

48-1. The method of claim 47, wherein the amine-containing material is an immunoglobulin.