METHOD FOR PRODUCING AN ALDEHYDE CONTAINING COATING

• US 20110177255A1
• Filed: 03/24/2006
• Published: 07/21/2011
• Est. Priority Date: 03/24/2005
• Status: Abandoned Application

• Current Assignee: University of Durham
• Original Assignee: University of Durham
• Inventors: Schofield, Wayne Christopher Edward, Badyal, Jas Pal Singh, McGettrick, James
• Application Number:
  US12/085,985
• Publication Number:
  US 20110177255A1
• Time in Patent Office: Days
• US Class Current: 427/488
• CPC Class Codes: B05D 1/62 Plasma-deposition of organic layers plasma deposition in general C23C14/00, C23C16/00
• CPC Class Codes: C23C 18/1851 of surfaces of non-metallic or semiconducting in organic material
• CPC Class Codes: C23C 18/2006 by other methods than those of C23C18/22 - C23C18/30
• CPC Class Codes: C23C 18/42 Coating with noble metals
• CPC Class Codes: D06M 10/025 Corona discharge or low temperature plasma
• CPC Class Codes: D06M 10/08 Organic compounds
• CPC Class Codes: D06M 14/18 using wave energy or particle radiation
• CPC Class Codes: D06M 14/20 on to materials of natural origin
• CPC Class Codes: D06M 14/26 on to materials of synthetic origin
• CPC Class Codes: G01N 33/54353 with ligand attached to the carrier via a chemical coupling agent coatings G01N33/54393
• CPC Class Codes: G01N 33/54393 Improving reaction conditions or stability, e.g. by coating or irradiation of surface, by reduction of non-specific binding, by promotion of specific binding

Abstract

A method is provided for applying a reactive aldehyde containing coating to a substrate. The method includes subjecting a substrate to a plasma discharge in the presence of a compound of formula (I):

Where X is an optionally substituted straight or branched alkylene chain(s) or aryl group(s); R¹, R² or R³ are optionally substituted hydrocarbyl or heterocyclic groups, and m is an integer greater than 0.

Claims

1. A method for applying a reactive aldehyde containing coating to a substrate, said method comprising the following step:

subjecting the substrate to a plasma discharge in the presence of a compound of formula (I)

2. The method according to claim 1 wherein the reactive aldehyde containing compound is a compound of formula (II)

3. The method according to claim 2 wherein the compound of formula (II) is a compound of formula (III)

where n=1-20.

4. The method according to claim 2 wherein the compound of formula (II) is a compound of formula (IIIa)

where n=1-20.

5. The method according to claim 1 wherein the aldehyde containing compound of formula (I) is a compound of formula (IV)

6. The method according to claim 5 wherein the compound of formula (IV) is a compound of formula (V)

7. The method according to claim 5 wherein the compound of formula (IV) is a compound of formula (Va)

where n=1-20.

8. The method according to claim 1 wherein the plasma discharge is pulsed.

9. The method according to claim 8 wherein the average power of the pulsed plasma discharge is less than 0.05 W/cm³.

10. The method according to claim 8 wherein the pulsed plasma discharge is applied such that the power is on for from 10 μ

s to 100 μ

s, and off for from 1000 μ

s to 20000 μ

s.

11. The method according to claim 8 wherein the pulsed plasma discharge is applied such that the pulsing regime changes in a controlled manner throughout the course of a single coating deposition.

12. The method according to claim 1 wherein the plasma discharge contains the compound of formula (I) in the absence of any other material.

13. The method according to claim 1 wherein additional materials to the compound of formula (I) are added to the plasma discharge.

14. The method according to claim 13 wherein said additional materials are inert and are not incorporated within the reactive aldehyde containing product coating.

15. The method according to claim 13 wherein said additional materials are non-inert and possess the capability to modify and/or be incorporated into the reactive aldehyde containing product coating.

16. The method according to claim 15 wherein the use of said non-inert additional materials results in a copolymer coating that contains reactive aldehyde functionality.

17. The method according to claim 1 wherein the introduction of the compound of formula (I) and/or any additional materials into the plasma discharge is pulsed.

18. The method according to claim 1 wherein the compound of formula (I) and/or any additional materials are introduced into the plasma discharge in the form of atomised liquid droplets.

19. The method according to claim 1 wherein the means for applying the coating is a reel-to-reel equipped plasma deposition apparatus.

20. The method according to claim 1 wherein the plasma deposition chamber is heated.

21. A substrate having an aldehyde containing coating thereon obtained by a process according to claim 1.

22. The method according to claim 1 which further includes the step of derivatization or reaction of the aldehyde groups after the deposition of the coating.

23. The method according to claim 22 wherein the step of the derivatization or reaction of the aldehyde groups is performed with an amine group.

24. The method according to claim 23 wherein a solution of said amine is contacted with the surface under conditions in which the amine functionality reacts with aldehyde groups on the surface.

25. A method for the immobilisation of an amine-containing reagent at a surface, said method including the application of a reactive aldehyde containing coating to a surface by a method according to claim 1, and then contacting the surface with a solution of said amine-containing agent under conditions such that the amine group reacts with the aldehyde groups.

26. The method according to claim 25 wherein immobilisation of the amine solution is spatially addressed onto the reactive aldehyde containing surface, such that amine immobilisation occurs only in given spatial locations.

27. The method according to claim 23 in which the amine is an amine-terminated biomolecule.

28. The method according to claim 27 wherein a modified surface is utilized for DNA hybridisation.

29. The method according to claim 22 wherein a solution of a silver containing salt reacts with surface aldehyde groups, resulting in silver metallization of the polymer surface.

30. The method according to claim 29 wherein Tollens reaction is used to generate metallic silver on the reactive aldehyde surface.

31. The method according to claim 1 wherein the substrate is any or any combination of metal, glass, semiconductor, ceramic, polymer, woven or non-woven fibres, natural fibres, cellulosic material or powder.

32. The method according to claim 1 wherein R¹, R² and/or R³ include fluoro, chloro, bromo and/or iodo substituents.

33. The method according to claim 3 wherein the compound of formula III, where m=1 and n=1, is ethylaldehyde acrylate.

34. The method according to claim 6 wherein the compound of formula V is 3-vinylbenzaldehyde.

35. The method according to claim 7 wherein the compound of formula Va, where m=1 and n=8, is 10-undecenal.

36. The method according to claim 9 wherein an average power of the pulsed plasma discharge is less than 0.0025 W/cm³.