The Dow Chemical Company

Joseph W Hanafin

George A Doorakian

Robert L Reierson

Bart J Bremmer

The invention is a process for the preparation of such 3-halo-2-hydroxyalkyl carbamates which comprises contacting an epihalohydrin carbonate with a secondary amine-containing compound, wherein the secondary amine has a pKa at which the secondary amine will react with the epihalohydrin carbonate and which does not catalyze the formation of unwanted by-products, in a polar organic solvent under conditions such that a 3-halo-2-hydroxyalkyl carbamate, wherein the carbamate nitrogen is tertiary, is prepared.

Process for preparing novel 3-halo-2-hydroxyalkyl carbamates

The invention is a compound which comprises one or more 3-halo-2-hydroxyalkyl carbamate moieties; wherein the carbamate nitrogen is tertiary. In preferred embodiments, the carbamate nitrogen is tertiary, and the carbamate nitrogen is further substituted by an alicyclic or aliphatic moiety or is part of a heterocyclic ring, wherein the heterocyclic ring can contain an oxygen or sulfur atom or may contain another tertiary 3-halo-2-hydroxyalkyl carbamate moiety; or wherein two or more of such 3-halo-2-hydroxyalkyl carbamates are linked by an aliphatic or alicyclic moiety. Another aspect of the invention is a process for the preparation of such 3-halo-2-hydroxyalkyl carbamates which comprises contacting an epihalohydrin carbonate with a secondary amine-containing compound, wherein the secondary amine has a pKa at which the secondary amine will react with the epihalohydrin carbonate and which does not catalyze the formation of unwanted by-products, in a polar organic solvent under conditions such that a 3-halo-2-hydroxyalkyl carbamate, wherein the carbamate nitrogen is tertiary, is prepared.

Novel 3-halo-2-hydroxyalkyl carbamates

Novel advanced epoxy resins are prepared using phosphine or phosphonium salt initiators bearing at least one hydroxyphenyl or thiophenyl groups. These phosphonium salt initiators are novel compositions of matter. The resulting resins contain reduced quantities of extractable phosphorus containing moieties.

Tetrahydrocarbyl phosphonium salts

This invention is novel compounds containing one or more 2,3-epoxyalkyl carbamate moieties wherein the carbamate nitrogen is tertiary; prepared by a process which comprises

2,3-Epoxy carbamates

Immobilized epoxy advancement initiators

Hydraulic fluids having high wet equilibrium reflux boiling points, good chemical stability and other desirable characteristics are made from certain cyano-substituted derivatives of cyclic ketals or acetals of the formula ##STR1## wherein A, B and R are specified radicals.

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Framingham, MA, United States of America

Joseph W Hanafin