Phthalonitriles derived from polyphenols

A phthalonitrile monomer made by a method comprising;

• reacting a polyphenol with a base and optionally a dihaloaromatic compound to form an organic salt;
• wherein the polyphenol is resveratrol;
• dihydroresveratrol;
• 4,4′-(but-2-ene-1,4-diyl)bis-2-methoxyphenol;
• 4,4′-(1,4-butane-diyl)bis-2-methoxyphenol;
• 1-ethyl-2-methyl-3-(4-hydroxyphenyl)-5-hydroxyindane;
• 4,4′-(ethane-1,1-diyl)diphenol;
• 5,5′-methylenebis(2-methoxy-4-methylphenol);
• 4,4′-methylenebis(5-isopropyl-2-methylphenol);
• 4,4′-(1-ethyl-2-methyl-1,3-propanediyl)bisphenol;
• or
• 5,5′-(ethane-1,1-diyl)bis(2-methoxy-4-methylphenol);
• wherein the dihaloaromatic compound if present comprises a carbonyl group, a sulfonyl group, a sulfinyl group, or a phosphoryl group;
• and
• wherein there is a molar excess of the hydroxy groups of the polyphenol relative to halo groups of the dihaloaromatic compound if present;
• and
• reacting the organic salt with 4-nitrophthalonitrile to form the phthalonitrile monomer.

A method comprising:

• providing a first phthalonitrile monomer made by a method comprising:
• reacting a first polyphenol with a first base and optionally a first dihaloaromatic compound to form a first organic salt;
• wherein there is a molar excess of the hydroxy groups of the first polyphenol relative to halo groups of the first dihaloaromatic compound if present;
• and
• reacting the first organic salt with 4-nitrophthalonitrile to form the first phthalonitrile monomer;
• optionally, providing a second phthalonitrile monomer made by a method comprising:
• reacting a second polyphenol with a second base and optionally a second dihaloaromatic compound to form a second organic salt;
• wherein there is a molar excess of the hydroxy groups of the second polyphenol relative to halo groups of the second dihaloaromatic compound if present;
• and
• reacting the second organic salt with 4-nitrophthalonitrile to form the second phthalonitrile monomer;
• wherein the first polyphenol and the second polyphenol if present are independently selected from resveratrol;
• dihydroresveratrol;
• 4,4′-(but-2-ene-1,4-diyl)bis-2-methoxyphenol;
• 4,4′-(1,4-butane-diyl)bis-2-methoxyphenol;
• 1-ethyl-2-methyl-3-(4-hydroxyphenyl)-5-hydroxyindane;
• 4,4′-(ethane-1,1-diyl)diphenol;
• 5,5′-methylenebis(2-methoxy-4-methylphenol);
• 4,4′-methylenebis(5-isopropyl-2-methylphenol);
• 4,4′-(1-ethyl-2-methyl-1,3-propanediyl)bisphenol;
• or
• 5,5′-(ethane-1,1-diyl)bis(2-methoxy-4-methylphenol);
• wherein the first dihaloaromatic compound if present and the second dihaloaromatic compound if present each comprise a group independently selected from a carbonyl group, a sulfonyl group, a sulfinyl group, or a phosphoryl group;
• wherein the first base and the second base if present are the same or different;
• wherein the first phthalonitrile monomer and the second phthalonitrile monomer if present are different;
• and
• making a phthalonitrile mixture by mixing the first phthalonitrile monomer with one or more of:
• the second phthalonitrile monomer if present;
• a monophthalonitrile compound;
• 1,3,5-tris(3,4-dicyanophenoxy)benzene;
• wherein n is a positive integer;
• and
• curing the phthalonitrile mixture to form a thermoset.

A method comprising:

• making a phthalonitrile mixture by mixing 1,3,5-tris(3,4-dicyanophenoxy)benzene with
• wherein n is a positive integer;
• and
• curing the phthalonitrile mixture to form a thermoset.