Photochemical methods and photoactive compounds for modifying surfaces

• US 9,454,077 B2
• Filed: 01/05/2015
• Issued: 09/27/2016
• Est. Priority Date: 11/09/2005
• Status: Expired due to Fees

• Current Assignee: Trustees Of Columbia University In The City Of New York (Columbia University)
• Original Assignee: Trustees Of Columbia University In The City Of New York (Columbia University)
• Inventors: Carroll, Gregory T., Koberstein, Jeffrey T., Wang, Denong, Turro, Nicholas J.
• Primary Examiner(s): Jackson, Shawquia
• Application Number:
  US14/589,306
• Publication Number:
  US 20160231649A1
• Time in Patent Office: 631 Days
• US Class Current: 1/1
• CPC Class Codes: B05D 3/06 by exposure to radiation B05D3/02 takes precedence ; plasma treatment B05D3/141
• CPC Class Codes: B05D 3/067 Curing or cross-linking the coating
• CPC Class Codes: B05D 5/00 Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures
• CPC Class Codes: B05D 7/02 to macromolecular substances, e.g. rubber treatment or coating of shaped articles made of macromolecular substances C08J7/00
• CPC Class Codes: B05D 7/14 to metal, e.g. car bodies involving a chemical reaction between the metal and the coating C23
• CPC Class Codes: C07C 49/303 to a six-membered ring
• CPC Class Codes: C07C 69/76 Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
• CPC Class Codes: C07D 209/48 with oxygen atoms in positions 1 and 3, e.g. phthalimide
• CPC Class Codes: C23C 18/1612 through irradiation means
• CPC Class Codes: C23C 18/1641 Organic substrates, e.g. resin, plastic
• CPC Class Codes: C23C 18/30 Activating or accelerating or sensitising with palladium or other noble metal
• CPC Class Codes: C23C 18/32 Coating with nickel, cobalt or mixtures thereof with phosphorus or boron C23C18/50 takes precedence
• CPC Class Codes: G03F 7/0045 with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
• CPC Class Codes: G03F 7/20 Exposure; Apparatus therefor photographic printing apparatus for making copies G03B27/00

Abstract

Compounds and methods for controlling the surface properties are described. Compounds of the invention can form radicals upon exposure to irradiation, which can then react with nearby molecules to alter the surface properties of various substrates. The invention can provide surfaces that are resistant to dewetting, surfaces that have immobilized molecules such as carbohydrates and polymers immobilized, and surfaces that have metals deposited on the surface. The invention can be utilized in a wide range of application, such as sensors, microreactors, microarrays, electroless deposition of metals, and the like.

Claims

1. A method for forming a dewetting-resistant surface, the method comprising:

depositing a molecule to at least a part of the surface, wherein the molecule is a polymer selected from the group consisting of polystyrene, polyether, polyester, polyamide, polyvinyl, polysaccharide, and mixtures thereof;

depositing a photoactive compound which comprises a compound of formula (I)

2. The method of claim 1, wherein said irradiating is carried out with at least one wavelength from about 290 to about 350 nm.

3. The method of claim 1, wherein the surface comprises an inorganic material, an organic material, a second polymer, silicon, wafers, or combinations thereof.

4. The method of claim 3, wherein the photoactive compound is

5. The method of claim 4, wherein said depositing the photoactive compound is carried out using a robotic spotter to obtain a pattern of crosslinked polymer and uncrosslinked polymer after said irradiation.

6. The method of claim 4, wherein said irradiating is carried out through a photomask having a desired pattern to obtain a pattern of crosslinked polymer and uncrosslinked polymer after said irradiation.

7. The method of claim 6, further comprising heating the surface to a temperature above the glass transition temperature or the melting temperature of the polymer.

8. The method of claim 7, wherein at least a portion of the uncrosslinked polymer has migrated to the interface of the crosslinked polymer and the uncrosslinked polymer to form a vertically rising structure.

9. The method of claim 3, wherein the photoactive compound is

10. The method of claim 9, wherein said depositing the photoactive compound is carried out using a robotic spotter to obtain a pattern of crosslinked polymer and uncrosslinked polymer after said irradiation.

11. The method of claim 9, wherein said irradiating is carried out through a photomask having a desired pattern to obtain a pattern of crosslinked polymer and uncrosslinked polymer after said irradiation.

12. The method of claim 11, further comprising heating the surface to a temperature above the glass transition temperature or the melting temperature of the polymer.

13. The method of claim 12, wherein at least a portion of the uncrosslinked polymer has migrated to the interface of the crosslinked polymer and the uncrosslinked polymer to form a vertically rising structure.