Covalent modification of metal surfaces

• US 8,066,824 B2
• Filed: 07/09/2007
• Issued: 11/29/2011
• Est. Priority Date: 07/07/2006
• Status: Active Grant

• Current Assignee: Intezyne Technologies
• Original Assignee: Intezyne Technologies
• Inventors: Breitenkamp, Rebecca, Skaff, Habib, Breitenkamp, Kurt, Sill, Kevin N.
• Primary Examiner(s): King; Roy
• Assistant Examiner(s): ZHENG, LOIS L
• Application Number:
  US11/825,791
• Publication Number:
  US 20080035243A1
• Time in Patent Office: 1,604 Days
• Field of Search: 148/251, 148/240, 525/482, 525/523
• US Class Current: 148/251
• CPC Class Codes: A61F 2/82 Devices providing patency to, or preventing collapsing of, tubular structures of the body, e.g. stents stent-grafts for tubular structures of the body other than blood vessels A61F2/04; stent-grafts for blood vessels A61F2/07; instruments specially adapted for placement or removal of stents or stent-grafts A61F2/95; for closing wounds, or holding wounds closed A61B17/04 - A61B17/115; dilators A61M29/00
• CPC Class Codes: A61L 2400/18 Modification of implant surfaces in order to improve biocompatibility, cell growth, fixation of biomolecules, e.g. plasma treatment
• CPC Class Codes: A61L 27/04 Metals or alloys
• CPC Class Codes: A61L 27/50 Materials characterised by their function or physical properties , e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
• CPC Class Codes: A61L 31/022 Metals or alloys
• CPC Class Codes: A61L 31/14 Materials characterised by their function or physical properties , e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
• CPC Class Codes: B05D 1/185 applying monomolecular layers B05D1/204 takes precedence
• CPC Class Codes: B05D 2202/00 Metallic substrate
• CPC Class Codes: B05D 3/102 Pretreatment of metallic substrates C23C takes precedence
• CPC Class Codes: B05D 3/142 Pretreatment
• CPC Class Codes: B82Y 30/00 Nanotechnology for materials or surface science, e.g. nanocomposites
• CPC Class Codes: B82Y 40/00 Manufacture or treatment of nanostructures
• CPC Class Codes: C07D 498/02 in which the condensed system contains two hetero rings

Abstract

The present invention provides modified metal surfaces, methods of preparing the same, and intermediates thereto. These materials are useful in a variety of applications including biomaterials.

Claims

1. A method for preparing a covalently modified metal surface, comprising the steps of:

(a) modifying a metal substrate to incorporate thereon a plurality of hydroxyl groups;

(b) providing a compound of formula I;

2. The method according to claim 1, wherein the metal substrate comprises iron.

3. The method according to claim 1, wherein the metal substrate is selected from a stainless steel, a cobalt alloy, a titanium alloy, an iron alloy, steel, stainless steel, austenitic stainless steel, Type 316 stainless steel, ferritic stainless steel, martensitic stainless steel, duplex stainless steel, cobalt, a cobalt alloy, a cobalt-chromium alloy, stellite alloys, titanium, titanium alloy, or a super-alloy.

4. The method according to claim 1, wherein step (c) is performed by condensation or dehydration reaction.

5. A method for preparing a covalently modified metal surface, comprising the steps of:

(a) providing a metal surface having a plurality of hydroxyl groups;

(b) providing a compound of formula I;

6. The method according to claim 5, wherein R¹ is a group of formula II:

7. The method according to claim 6, wherein R¹ is a group of formula II-d:

8. The method according to claim 6, further comprising the step of coupling the azide-terminal end to a suitable group via Click chemistry.

9. The method according to claim 5 wherein R¹ is selected from any of the following groups:

10. The method according to claim 5, wherein the metal substrate comprises iron.

11. The method according to claim 5, wherein the metal substrate is selected from a stainless steel, a cobalt alloy, a titanium alloy, an iron alloy, steel, stainless steel, austenitic stainless steel, Type 316 stainless steel, ferritic stainless steel, martensitic stainless steel, duplex stainless steel, cobalt, a cobalt alloy, a cobalt-chromium alloy, stellite alloys, titanium, titanium alloy, or a super-alloy.