Plasma deposition method for catechol/quinone functionalised layers

Patent metadata

Field	Value
Publication number	US-10843224-B2
Application number	US-201515515916-A
Country	US
Kind code	B2
Filing date	Aug 24, 2015
Priority date	Sep 30, 2014
Publication date	Nov 24, 2020
Grant date	Nov 24, 2020

Abstract

A solvent-free plasma method for depositing an adherent catechol and/or quinone functionalised layer to an inorganic or organic substrate from a precursor which comprises at least a quinone group; a protected or unprotected catechol group; a molecule substituted by a quinone group and/or a protected or unprotected catechol group; and/or a natural or synthetic derivative of a catechol group and/or a quinone group; wherein the quinone group is a 1,2-benzoquinone group and the catechol group is a 1,-dihydroxybenzene group.

First claim

The invention claimed is:

1. A method for adhering a catechol and quinone functionalized layer to a substrate wherein the method comprises the steps of:
a) providing a substrate;
b) providing a precursor comprising at least one monomer and a molecule with an unprotected catechol group;
c) applying a plasma procedure to said precursor and said substrate in order to form a coating comprising a catechol and quinone functionalized layer on said substrate,
wherein said molecule with an unprotected catechol group is at least one of

and

wherein R 2 and R 3 are the same or different, and independently represent a hydrogen atom, a saturated C 1-4 hydrocarbon group, and wherein P 1 represents separately and independently —NH 2 , —COOH, —OH, —SH,

wherein R 2 and R 3 are the same or different, and independently represent a hydrogen atom, a saturated C 1-4 hydrocarbon group, an halogen,

wherein each of A 1 and A 2 independently represents a hydrogen atom; or

wherein LG represents a linking group and is chosen from oligomers having chemical structure —[C(R 2 )(R 3 )] x —P 2 wherein R 2 and R 3 are the same or different, and independently represent a hydrogen atom, a saturated C 1-4 hydrocarbon group and wherein P 2 represents —NH 2 , —COOH, —OH, —SH, an halogen, —NH-A 5 -, —C(O)A 6 , —CH(NHA 5 )-c(O)-A 6 wherein A 5 represents —H, —C and A 6 represents —OH, —NH 2 .

2. The method according to claim 1 , wherein said monomer is vinyltrimethoxysilane.

3. The method according to claim 1 , wherein a step of cleaning the substrate by ultrasonic washing is carried out before step (a).

4. The method according to claim 1 , wherein a polymerisation initiator agent is injected into the precursor one of before step (c) or during step (c).

5. The method according to claim 4 , wherein said polymerization initiator agent is a free radical initiator.

6. The method according to claim 5 , wherein said free radical initiator is one of 4,4′-azobis(4-cyanopentano acid), 2,2′-azobis[2-methyl-N-(1,1-bis-(hydroxymethyl)-hydroxyethylpropionamide],2,2′-azobis(2-methylpropionamidine)dihydrochloride, 2,2′-azobis[2-methyl-N-(2-hydroxyethyl)propionamide], 2,2′-azobis(isobutyramidine hydrochloride), 2,2′-azobis[2-methyl-N-(1,1-bis(hydroxymethyl)-2-ethyl)-propionamide], 2,2′-azobis[2-(2-imidazolin-2-yl)propane]dihydrochloride, 2,2′-Azobis[N-(2-carboxyethyl)-2-methylpropionamidine] hydrate, 2,2′-Azobis{2-[1-(2-hydroxyethyl)-2-imidazolin-2-yl]propane}dihydrochloride, 2,2′-Azobis(1-imino-1-pyrrolidino-2 ethylpropane)dihydro chloride, 2,2′-Azobis{2-methyl-N-[1,1-bis(hydroxymethyl)-2-hydroxyethyl]propionamide},2,2′-azobis[2-methyl-N-(2-hydroxyethylpropionamide], 2,2′-azobis(isobutylamide) dihydrate, or azoinitiators having polyethylene glycol unit.

7. The method according to claim 1 , wherein the plasma used in step (c) is a non-equilibrium plasma process operating at atmospheric pressure.

8. The method according to claim 1 , wherein said plasma of step (c) is generated by an electrical excitation, said electrical excitation comprising an electrical signal which is delivered in a pulsed wave form.

9. The method according to claim 1 , wherein said monomer is at least one of an acrylate derivative, a methacrylate derivative, a styrene derivative, a vinyl ester derivative, a vinyl amide derivative, acrylonitrile, methacrylonitrile, acrylamide, methacrylamide, an unsaturated vegetable oil, a fatty acid, an acryclic acid, a methacrylic acid, a vinyl alkoxysilanes, ethylene, hexamethyldisiloxane, hexamethyldisilazane, octamethylcyclotetrasiloxane, decamethylcylcopentasiloxane, dodecamethylcyclohexasiloxane, hexaethyldisiloxane, tetraethylorthosilicate, tetramethyldisiloxane, pentamethylcyclopentasiloxane, octamethylcyclooctasiloxane, polydimethylsiloxane and derivatives of polydimethylsiloxane.

Assignees

• Luxembourg Inst Science & Tech List

Inventors

• Detrembleur Christophe
• Vandeweerdt Cecile
• Vreuls Christelle
• Mauchauffe Rodolphe
• Moreno-Couranjou Maryline
• Boscher Nicolas
• Choquet Patrick

Classifications

• B05D1/62 Primary

  Plasma-deposition of organic layers (plasma deposition in general C23C14/00, C23C16/00) · CPC title

• C09D133/04

  Homopolymers or copolymers of esters {(C09D143/04 takes precedence)} · CPC title

• C09D133/26

  Homopolymers or copolymers of acrylamide or methacrylamide · CPC title

• B05D5/00

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