Photochemical methods and photoactive compounds for modifying surfaces

Patent metadata

Field	Value
Publication number	US-9454077-B2
Application number	US-201514589306-A
Country	US
Kind code	B2
Filing date	Jan 5, 2015
Priority date	Nov 9, 2005
Publication date	Sep 27, 2016
Grant date	Sep 27, 2016

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.

First claim

We claim:

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)

and/or a compound of formula (II)

(II), and
irradiating the photoactive compound to obtain the dewetting-resistant surface, wherein:
n is an integer from 1 to 1000;
Y is independently —CH 2 —, —C(O)—, —OC(O)—, —C(O)O—, —C(O)NR 3 —, or —NR 3 C(O)—;
each of the rings A, B, C, D, E, and F is substituted with one or more R 1 groups;
R 1 is independently a hydrogen, a halogen, a hydroxyl, an aryl, an amide, a cyano, a substituted or unsubstituted straight- or branched-chain alkyl which contains 1 to 6 carbons, a substituted or unsubstituted alkene which contains 2 to 4 carbons, a substituted or unsubstituted alkyne which contains 2 to 4 carbons, —C(O)R 3 , —CO 2 R 3 , —OC(O)R 3 , —OR 3 , or —OC(O)R 5 ;
R 3 is independently a hydrogen, a substituted or unsubstituted C 1 -C 10 straight-chain or branched-chain alkyl, or a substituted or unsubstituted alkene; and
R 5 is independently a hydrogen, an unsubstituted straight- or branched-chain alkyl that contains 1-6 carbons, or a straight- or branched-chain alkyl that contains 1-6 carbons and is substituted by an alkyne.

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.

Assignees

• Univ Columbia

Inventors

• Carroll Gregory T
• Koberstein Jeffrey T
• Wang Denong
• Turro Nicholas J

Classifications

• C23C18/1612

  through irradiation means · CPC title

• G03F7/0045 Primary

  with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors · CPC title

• B05D5/00

  Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures · CPC title

• C23C18/32

  Coating with nickel, cobalt or mixtures thereof with phosphorus or boron (C23C18/50 takes precedence) · CPC title

• B05D7/14

  to metal, e.g. car bodies (involving a chemical reaction between the metal and the coating C23) · CPC title