A series of renewable bisphenols has been synthesized from creosol (2-methoxy-4-methylphenol) through stoichiometric condensation with short chain aldehydes. Creosol can be readily produced from lignin, potentially allowing for the large scale synthesis of bisphenol A replacements from abundant waste biomass. The renewable bisphenols were isolated in good yield and purity without resorting to solvent intense purification methods. Zinc acetate was shown to be selective catalyst for ortho-coupling of formaldehyde but was unreactive with more sterically demanding aldehydes. Dilute HCl and HBr solutions were shown to be effective catalysts for the selective coupling of aldehydes in the position meta to the phenol. Acid solutions could be recycled and used multiple times without decreases in activity or yield.

Electrolytes and electrolyte additives for energy storage devices comprising cyanate based compounds are disclosed. The energy storage device comprises a first electrode and a second electrode, wherein at least one of the first electrode and the second electrode is a Si-based electrode, a separator between the first electrode and the second electrode, an electrolyte comprising at least two electrolyte co-solvents, wherein at least one electrolyte co-solvent comprises a cyanate based compound.

Electrolytes and electrolyte additives for energy storage devices comprising cyanate based compounds are disclosed. The energy storage device comprises a first electrode and a second electrode, wherein at least one of the first electrode and the second electrode is a Si-based electrode, a separator between the first electrode and the second electrode, an electrolyte comprising at least two electrolyte co-solvents, wherein at least one electrolyte co-solvent comprises a cyanate based compound.

The invention describes a high yield process that utilizes selective catalysts for the conversion of abundant, naturally occurring terpenes into bisphenols, and their derivative bis(cyanate)esters, resins, and polymers. High performance, low-cost composite materials with low moisture uptake and high glass transition temperatures suitable for aerospace applications can be prepared from these renewable starting materials.

The invention describes a high yield process that utilizes selective catalysts for the conversion of abundant, naturally occurring terpenes into bisphenols, and their derivative bis(cyanate)esters, resins, and polymers. High performance, low-cost composite materials with low moisture uptake and high glass transition temperatures suitable for aerospace applications can be prepared from these renewable starting materials.

The present invention provides a novel cyanate ester compound which has excellent solvent solubility and from which a hardened product having a low coefficiency of thermal expansion and excellent flame retardancy and heat resistance is obtained. The present invention is a cyanate ester compound obtained by cyanating a naphthol-dihydroxynaphthalene aralkyl resin or a dihydroxynaphthalene aralkyl resin.

The present invention provides a novel cyanate ester compound which has excellent solvent solubility and from which a hardened product having a low coefficiency of thermal expansion and excellent flame retardancy and heat resistance is obtained. The present invention is a cyanate ester compound obtained by cyanating a naphthol-dihydroxynaphthalene aralkyl resin or a dihydroxynaphthalene aralkyl resin.

The present invention is a cyanate ester compound represented by the following formula (1): ##STR00001## wherein Ar represents an aromatic ring; R.sub.1 each independently represents a hydrogen atom, an alkyl group, or an aryl group; n each independently represents an integer of 1 to 3; m+n is the same as the total number of hydrogen atoms in a monovalent aromatic group containing the aromatic ring and the hydrogen atoms; R.sub.2 represents a hydrogen atom (excluding a case where Ar represents a benzene ring; n each represents 1; R.sub.1 represents a hydrogen atom; m each represents 4, and a cyanate group is bonded to the benzene ring in the 4-position relative to an adamantyl group), or an alkyl group having 1 to 4 carbon atoms; and R.sub.3 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

The present invention is a cyanate ester compound represented by the following formula (1): ##STR00001## wherein Ar represents an aromatic ring; R.sub.1 each independently represents a hydrogen atom, an alkyl group, or an aryl group; n each independently represents an integer of 1 to 3; m+n is the same as the total number of hydrogen atoms in a monovalent aromatic group containing the aromatic ring and the hydrogen atoms; R.sub.2 represents a hydrogen atom (excluding a case where Ar represents a benzene ring; n each represents 1; R.sub.1 represents a hydrogen atom; m each represents 4, and a cyanate group is bonded to the benzene ring in the 4-position relative to an adamantyl group), or an alkyl group having 1 to 4 carbon atoms; and R.sub.3 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

A material for forming an underlayer film for lithography, in which a compound represented by the following formula (0) is used.

##STR00001##

(in formula (0), each X independently represents an oxygen atom or a sulfur atom, or a non-crosslinked state, R.sup.1 represents a 2n-valent group having 1 to 30 carbon atoms, or a single bond, each R.sup.0 independently represents a straight, branched or cyclic alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, a straight, branched or cyclic alkenyl group having 2 to 30 carbon atoms, a thiol group, a halogen group, a nitro group, an amino group, a carboxylic acid group or a hydroxyl group, the alkyl group, the alkenyl group and the aryl group each optionally include a cyanato group, a thiol group, a halogen group, a nitro group, an amino group, a carboxylic acid group, a hydroxyl group, an ether bond, a ketone bond or an ester bond, each m.sub.1 is independently an integer of 0 to 4, in which at least one m.sub.1 is an integer of 1 to 4, each m.sub.2 is independently an integer of 0 to 3, n is an integer of 1 to 4, and each p is independently 0 or 1.)