The Dow Chemical Company

George A Doorakian

Lawrence G Duquette

James L Bertram

Marsha A Paul

Adolphus V Gist

Ross C Whiteside, Jr

Philip W McGraw

Joseph W Hanafin

Martin C Cornell, Iii

Dennis L Schmidt

John F Arnett

Donald L Schmidt

Horst G Langer

Randall C Rains

Thomas P Brady

Paul E Strege

Bruce L Burton

John Martin

Wanda S Smith

The invention is a process for the preparation of halohydroxyalkyl 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 the further presence of an acid scavenger capable of forming a salt with the hydrogen halide by-product formed, in an amount sufficient to prevent the formation of unwanted by-products, in a polar organic solvent under conditions such that a halohydroxyalkyl carbamate, wherein the carbamate nitrogen is tertiary, is prepared. Another aspect of this invention is the further step of contacting the 3-halo-2-hydroxyalkyl carbamate with an ion-exchange resin with pendant moieties containing hydroxide moieties in a lower alkanol solvent under conditions such that the 3-halo-2-hydroxyalkyl moieties are converted to 2,3-epoxyalkyl moieties so as to prepare a 2,3-epoxyalkyl carbamate.

Process for the preparation of halohydroxyalkyl carbamates and 2,3-epoxy

A process for preparing a phosphate ester which contains at least one terminal epoxide moiety, the process comprising contacting under reaction conditions, optionally in the presence of water, at least one phosphoric acid ester with an amount of an epoxide having an epoxy equivalent greater than one. The product compositions can be cured by standard epoxide curing agents to provide protective coatings having intumescent properties.

Epoxy phosphate compositions

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

Epoxy resins having improved properties are prepared by reacting an epoxy resin with a dihydric phenol in the presence of a sufficient quantity of a phosphonium trifluoroacetate catalyst such that the product resulting from reacting a mixture of the catalyst, epoxy resin and dihydric phenol has a % epoxide difference from the theoretical percent epoxide of from about 0.5 to about 4.0.

Process for preparing epoxy resins employing a phosphonium

Immobilized epoxy advancement initiators

An improved process for reacting vicinal epoxides with phenols or thiophenols is described. This process is conducted at essentially anhydrous conditions and temperatures less than 175.degree. C. The resulting resins are generally more linear and less colored than advanced resins produced via prior art processes. Also the phosphonium catalyst remains active to promote subsequent advancement or curing reactions. The catalyst can be deactivated in a separate step to produce a resin of exceptional purity.

Process for producing epoxy resins

Epoxy resins having improved properties are prepared by reacting an epoxy resin with a dihydric phenol in the presence of a sufficient quantity of a phosphonium catalyst such that the product resulting from reacting a mixture of the catalyst, epoxy resin and dihydric phenol has a % epoxide difference from the theoretical percent epoxide of from about 0.5 to about 4.0.

Process for preparing epoxy resins having improved physical properties

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

Certain tetrahydrocarbyl phosphonium phenoxide salts are described herein which are novel compounds and/or novel catalysts for promoting the reaction between vicinal epoxides and phenols and/or carboxylic acids or anhydrides. These catalysts are particularly useful in preparing high molecular weight epoxy resins by the advancement reaction of diglycidyl ether of bisphenol A with bisphenol A.

Phosphonium phenoxide catalysts for promoting reaction of epoxides with

Epoxy resins having improved physical properties when cured

Blocked isocyanates are deblocked by heating in the presence of an organo phosphorus-containing compound.

Organo phosphorus-containing compounds as catalysts for deblocking

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

A tetrahydrocarbylphosphonium phenoxide salt is prepared by reacting a tetrahydrocarbylphosphonium halide salt with an alkali metal or ammonium hydroxide in a liquid reaction medium in the presence of at least an equivalent amount of a phenol. This method of preparation is especially effective where the hydroxide salt of the tetrahydrocarbylphosphonium is unstable. For example, benzyltriphenylphosphonium salt of bisphenol A complexed with bisphenol A is prepared by adding 1 equivalent of sodium hydroxide to a methanol solution containing 1 equivalent of benzyltriphenylphosphonium bromide and 2 equivalents of bisphenol A at 30.degree. C.

Growing community of inventors

Bedford, MA, United States of America

George A Doorakian