The Dow Chemical Company

Lawrence G Duquette

George A Doorakian

James L Bertram

Robert H Heistand, Ii

Philip E Garrou

Philip W McGraw

A Dale Harley

Iwao Kohatsu

Issam A Khoury

John Martin

John F Arnett

Methods of producing ABO.sub.3 compounds in which A represents a first metal ion and B represents a second metal ion from mixed metal coordination complexes are disclosed. The methods involve reacting compounds serving as a source of the B metal ion with a substituted aromatic compound, in solution, and thereafter reacting the metal coordination complex formed with a compound serving as a source of the A metal, in solution. An example is the reaction of titanium tetraisopropoxide with catechol to form a titanium catecholate coordination complex which is thereafter reacted with barium hydroxide octahydrate to form a pentamethanol barium triscatecholatotitanate mixed metal coordination complex which can be calcined at elevated temperatures to produce the ABO.sub.3 compound, barium titanate (BaTiO.sub.3), which is known to have outstanding dielectric, ferroelectric and piezoelectric properties. Portions of the A and/or B ions can be substituted with other metals.

Preparation of ABO.sub.3 compounds from mixed metal aromatic

Preparation of a ceramic green body by hydrolyzing two groups of alkoxides to form a dispersion of their reaction product, concentrating the dispersion to a sediment without drying it, and admixing a binder solution, plasticizer and release agent with the sediment to make a ceramic slip formulation. The slip formulation is then cast as a ceramic green body. The proportions of alkoxides can be adjusted to produce a ceramic green body which is dielectric and useful for microcapacitors.

Dispersion process for ceramic green body

The invention is the process which comprises contacting a reaction mixture comprising between about 1 and 100 percent by weight of a polyethylene-substituted piperazine, a piperazine or mixtures thereof, wherein such compounds contain a primary or secondary nitrogen wherein one of the carbons adjacent to the nitrogen has a hydrogen atom bonded to the carbon atom, and between about 1 and 99 percent of a solvent, with a catalytic amount of palladium on a support, at a temperature of between about 150.degree. C. and 300.degree. C., under condition such that the product so prepared contains polyethylene polypiperazines.

Polyethylene polypiperazine compositions

Tetrahydrocarbyl phosphonium bicarbonate salts are employed as catalysts to promote the reaction between (a) vicinal epoxides and (b) carboxylic acids or anhydrides. These catalysts are particularly useful in the preparation of vinyl ester resins.

Phosphonium bicarbonate catalysts for promoting reaction of epoxides

Tetrahydrocarbyl phosphonium bicarbonate salts are described which are unexpectedly effective as catalysts for promoting the reaction between (a) vicinal epoxides and (b) phenols. These catalysts are particularly useful in preparing high molecular weight epoxy resins by the advancement reaction of an epoxy resin with a polyhydric phenol.

Novel amide acetals of the formula ##STR1## wherein R.sub.1 is hydrogen, methyl or Y and Y is the remnant of a hydroxyl-containing compound are claimed. The compounds are useful as water scavengers in fluid compositions.

Piperazine derivatives

Certain tetrahydrocarbylphosphonium bicarbonate salts are produced by reacting a trihydrocarbyl(hydrocarbylcarboxymethyl)phosphonium hydroxide inner salt with water. For example, methyl tri-n-butylphosphonium bicarbonate salt was prepared in quantitative yields by heating tri-n-butylcarboxymethylphosphonium hydroxide inner salt in an aqueous methanol solution at 100.degree. C. for 3 hours.

Process for preparing tetrahydrocarbylphosphonium bicarbonate salts

Compounds of formulas I and II are heat-activated catalysts used in making polyurethanes. ##STR1## wherein R, R.sub.1, and R.sub.2 are each independently H, hydrocarbyl or an inertly-substituted hydrocarbyl; R.sub.3 and R.sub.4 are each independently hydrocarbyl or an inertly-substituted hydrocarbyl; and X is an anion. Upon heating, Compounds I and II catalyze the reaction and may release gaseous by-products which cause the resulting polyurethane compound to foam. For example, the catalyst, t-butyl imidazole-N-carboxylate, when heated to 120.degree. C., catalyzes the reaction between a polyol and a polyisocyanate to give a foamed polyurethane which cured in 16 minutes.

Catalyst for making polyurethanes

The trisubstituted (2,5-dihydroxyphenyl)phosphonium hydroxide inner salts and their hydrolyzed derivatives are novel latent catalysts for promoting reaction between vicinal epoxides and phenols and/or carboxylic acids (or anhydrides). Precatalyzed epoxy resins are easily prepared using such catalysts.

Novel tributyl (2,5-dihydroxyphenyl)phosphonium hydroxide inner salts

Latent catalysts for promoting reaction of epoxides with phenols and/or

Ar-cyclic sulfonium arenethiol salts exemplified by the formula: ##STR1## may be converted to their corresponding zwitterion, exemplified by the formula: ##STR2## The latter polymerize very readily upon exposure to mild conditions of heat or radiative energy. The resultant polymers are water-insoluble resins useful as adhesives, coatings, films and the like. The zwitterions containing more than one arenesulfide and cyclic sulfonium group per molecule, crosslink upon exposure to heat to form thermoset resins.

Ar-cyclic sulfonium arenethiol salts and their zwitterions

The title compounds are prepared by reacting (a) a trihydrocarbylphosphine, (b) p-benzoquinone, and (c) a protic acid in a liquid reaction medium comprising a lower alkanol of from 1 to 4 carbon atoms, a 1,2-alkylene glycol, dialkylene glycol or trialkylene glycol or a lower alkyl mono-ether of said glycols. The glycols are either ethylene glycol, propylene glycol, or the indicated oligomers thereof. Methanol is the solvent of choice. As an example, tri-n-butyl (2,5-dihydroxyphenyl)phosphonium chloroacetate was prepared in excellent yields by slowly adding tri-n-butylphosphine, precooled to about 0.degree. C, to a vigorously stirred suspension of p-benzoquinone in a methanol solution of chloroacetic acid at a temperature of approximately -10.degree. C. A precatalyzed epoxy resin was obtained by merely adding the methanol solution of the phosphonium chloroacetate to a liquid epoxy resin (e.g., the diglycidyl ether of bisphenol-A).

Process for preparing trihydrocarbyl (2,5-dihydroxyphenyl) phosphonium

Novel epoxy resin compositions are disclosed which comprise (A) an epoxy resin, (B) a latent amine curing agent for said epoxy resin, and (C) a unique class of latent accelerators corresponding to formula I ##SPC1## wherein:

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Maynard, MA, United States of America

Lawrence G Duquette