Hydrogen cyanide-based polymer surface coatings and hydrogels

Patent metadata

Field	Value
Publication number	US-9587141-B2
Application number	US-201314401310-A
Country	US
Kind code	B2
Filing date	May 17, 2013
Priority date	May 17, 2012
Publication date	Mar 7, 2017
Grant date	Mar 7, 2017

Abstract

The present invention provides a process of coating at least a portion of a substrate surface comprising contacting the surface with hydrogen cyanide monomeric units under conditions permitting polymerisation of the hydrogen cyanide monomeric units to form a polymer that coats the surface. Also provided is a substrate coated by a polymer according to the claimed process. Also provided is a method of forming a hydrocyanic acid-based hydrogel, the method comprising co-polymerisation in a solution, the solution comprising hydrogen cyanide monomer units and co-monomers.

First claim

The invention claimed is:

1. A process of coating at least a portion of a substrate surface comprising contacting the substrate surface with hydrogen cyanide monomeric units in a liquid solution, adding base to provide conditions permitting polymerisation of the hydrogen cyanide monomeric units, and forming a polymer coating on the at least a portion of the substrate surface.

2. A process according to claim 1 , wherein the hydrogen cyanide monomeric units are provided in an aqueous solution and the base increases the pH of the aqueous solution to provide the conditions permitting polymerisation.

3. A process according to claim 1 , wherein the base provides the conditions permitting polymerisation of the hydrogen cyanide monomeric units by neutralising protonated hydrogen cyanide monomeric units to form neutralised hydrogen cyanide monomeric units.

4. A process according to claim 1 , wherein the hydrogen cyanide monomeric units are selected from the group consisting of one or more of hydrogen cyanide, iminoacetonitrile, aminomalononitrile, diaminomaleonitrile, aminoacetonitrile, azidoacetonitrile and isomers of any one of these.

5. A process according to claim 1 , wherein the hydrogen cyanide monomeric units are selected from the group consisting of one or more of hydrogen cyanide, aminomalononitrile, aminoacetonitrile, and isomers of any one of these.

6. A process according to claim 1 , wherein the hydrogen cyanide monomeric units consist essentially of hydrogen cyanide or aminomalononitrile.

7. A process according to claim 3 , wherein the base neutralises the protonated hydrogen cyanide monomeric units in an aqueous solution, and wherein the process further comprises
extracting the neutralised hydrogen cyanide monomeric units from the aqueous solution using an organic solvent, wherein
the substrate surface is contacted with the organic solvent comprising the neutralised hydrogen cyanide monomeric units
to form the polymer coating on the at least a portion of the surface.

8. A process according to claim 1 , wherein the liquid solution of hydrogen cyanide monomeric units comprises one or more of fillers, pigments, wetting agents, viscosity modifiers, stabilizers, anti-oxidants, ligands, cross-linking agents, co-monomers, nanoparticles, biopolymers, and metals.

9. A process according to claim 1 , wherein the process has a further step of contacting the polymer coating with one or more reactive moieties, wherein the one or more reactive moieties reacts with and is bound to the polymer coating.

10. A process according to claim 1 , wherein the process has a further step of grafting a further polymer to the polymer coating by contacting the surface with the further polymer, wherein the further polymer reacts with and is bound to the polymer coating or any reactive moieties attached to the polymer coating.

11. A process according to claim 2 , wherein the pH is increased to above 7 and below 12.

12. A process according to claim 2 , wherein the pH is increased to from 8 to 9.

13. A process according to claim 1 , wherein the hydrogen cyanide monomeric units are provided as a stabilised salt of an acid selected from the group consisting of p-toluenesulfonic acid, hydrochloric acid, sulphuric acid or other acids.

14. A process according to claim 1 , wherein the liquid solution is acidic and comprises an acid selected form the group consisting of p-toluenesulfonic acid, methane sulfonic acid, trifluoroacetic acid, sulphuric acid, hydrochloric acid, nitric acid, triflic acid, trifluoroacetic acid, acetic acid, phosphoric acid, and perchloric acid.

15. A process according to claim 14 , wherein the acid is p-toluenesulfonic acid.

16. A process according to claim 9 , wherein the one or more reactive moieties comprises a silver salt.

17. A process according to claim 1 , wherein the substrate is of organic material.

18. A process according to claim 1 , wherein the liquid solution of hydrogen cyanide monomeric units further comprises a co-monomer that provides additional functionalisation of the polymer coating.

19. A process according to claim 1 , wherein the liquid solution of hydrogen cyanide monomeric units further comprises a co-monomer wherein the co-monomer comprises functional groups selected from the group consisting of amines, thiols, nitriles, aldehydes, imidazoles, azides, polyhexamethylene dithiocarbonate, hydrogen, hydroxyls, carboxylic acids, carboxylic esters, carboxamides, alkyl halides, benzylic halides, epoxides, thioepoxides, isocyanates and combinations thereof.

20. A process according to claim 1 , wherein the liquid solution of hydrogen cyanide monomeric units comprises a co-monomer selected from the group of compounds containing primary amines, secondary amines, thiols, acrylates, methacrylates, epoxides, thioepoxides, isothiocyanates, alkyl halides and arylmethyl halides.

21. A process according to claim 1 , wherein the hydrogen cyanide monomeric units consist essentially of multimers of hydrogen cyanic acid.

22. A process according to claim 1 , wherein the hydrogen cyanide monomeric units consist essentially of aminomalononitrile.

23. A process according to claim 1 , wherein the base is soluble in the liquid solution and is selected from the group consisting of sodium hydroxide, potassium hydroxide, ammonium hydroxide, calcium hydroxide, magnesium hydroxide, barium hydroxide, aluminium hydroxide, ferrous hydroxide, ferric hydroxide, zinc hydroxide, lithium hydroxide, 2-amino-2-hydroxymethyl-propane-1,3-diol, and ammonium di-methyl amine.

24. A process according to claim 1 , further comprising contacting the polymer coating with cells to form a surface having adherent cells.

25. A process of coating at least a portion of a substrate surface comprising contacting the substrate surface with hydrogen cyanide monomeric units comprising aminomalononitrile in a liquid solution, adding a soluble base to provide conditions permitting polymerisation of the hydrogen cyanide monomeric units, and forming a polymer coating on the at least a portion of the substrate surface.

Assignees

• Commw Scient Ind Res Org
• Commonwealth Scient And Ind Res Organization

Inventors

• Thissen Helmut
• Evans Richard
• Koegler Aylin

Classifications

• Y10T428/265

  1 mil or less · CPC title

• C09D179/02 Primary

  Polyamines · CPC title

• C01C3/10

  Simple alkali metal cyanides · CPC title

• C08G61/00

  Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule (C08G2/00 - C08G16/00 take precedence) · CPC title

• C08G73/06 Primary

  Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule · CPC title