Polymeric materials made from vanillin

Patent metadata

Field	Value
Publication number	US-9815775-B1
Application number	US-201615141930-A
Country	US
Kind code	B1
Filing date	Apr 29, 2016
Priority date	Nov 21, 2011
Publication date	Nov 14, 2017
Grant date	Nov 14, 2017

Abstract

A vanillin is found to be a useful starting material for preparing new monomers that can be further applied to make high Tg composite resins that are in turn useful for making composite parts.

First claim

What is claimed is:

1. A bis(cyanate) ester monomer (A) produced by the method, comprising:
treating vanillin with hydrogen pressure in the presence of a metal catalyst to afford 4-methyl-2-methoxyphenol;
treating said 4-methyl-2-methoxyphenol with oxidative coupling agents that induce a coupling of the aromatic rings at the 6-position to afford 6,6-dimethyl-3,3-dimethoxy-2,2-dihydroxybiphenyl;
treating said 6,6-dimethyl-3,3-dimethoxy-2,2-dihydroxybiphenyl with at least one cyanogen halide and base in an organic solvent to create a new biphenyl cyanate ester monomer, and

purifying said monomer by recrystallizing or precipitating from an organic solvent.

2. A bis(cyanate) ester monomer (A) produced by the method, comprising:
treating vanillin with hydrogen Pressure ranging from 1 psig to about 6000 psig in the presence of a metal catalyst to afford 4-methyl-2-methoxyphenol, wherein said metal catalyst is selected from the group consisting of nickel, palladium, and platinum used as single metals, mixtures thereof, supported on carbon and other inorganic supports;
treating said 4-methyl-2-methoxyphenol with oxidative coupling agents that induce a coupling of the aromatic rings at the 6-position to afford 6,6-dimethyl-3,3-dimethoxy-2,2-dihydroxybiphenyl;
treating said 6,6-dimethyl-3,3-dimethoxy-2,2-dihydroxybiphenyl with at least one cyanogen halide and base in an organic solvent to create a new biphenyl cyanate ester monomer, wherein said cyanogen halide is selected from the group consisting of cyanogen bromide, cyanogen iodide, and cyanogen chloride; and

purifying said monomer by recrystallizing or precipitating from an organic solvent.

3. A bis(cyanate) ester monomer (A) produced by the method, comprising:
treating vanillin with hydrogen pressure in the presence of a metal catalyst to afford 4-methyl-2-methoxyphenol;
treating said 4-methyl-2-methoxyphenol with oxidative coupling agents that induce a coupling of the aromatic rings at the 6-position to afford 6,6-dimethyl-3,3-dimethoxy-2,2-dihydroxybiphenyl, wherein said oxidative coupling agents is an oxidative enzyme of biological origin, or said oxidative coupling agents used in the chemical reaction is regenerated by electrochemical methods, or wherein said oxidative enzyme is horseradish peroxidase;
treating said 6,6-dimethyl-3,3-dimethoxy-2,2-dihydroxybiphenyl with at least one cyanogen halide and base in an organic solvent to create a new biphenyl cyanate ester monomer; and

purifying said monomer by recrystallizing or precipitating from an organic solvent.

4. A bis(cyanate) ester monomer, comprising the following structure:

Assignees

• Us Gov Sec Navy
• Us Navy

Inventors

• Wright Michael E
• Harvey Benjamin G

Classifications

• C08G65/38 Primary

  derived from phenols · CPC title

• C07C253/04 Primary

  by reaction of cyanogen halides, e.g. ClCN, with organic compounds · CPC title

• C07C37/002

  by transformation of a functional group, e.g. oxo, carboxyl · CPC title

• C12P13/002

  Nitriles (-CN) · CPC title

• D06M2101/40

  Fibres of carbon · CPC title