Aerojet-general Corporation

Roger B Steele

Arthur Katzakian, Jr

Herman H Weyland

Marvin H Gold

Edward E Hamel

Joseph J Scigliano

This patent describes the catalytic promotion of the reaction of oxirane-containing compounds with carboxylic acid compounds at high, ambient, and low temperature. Specifically, this patent describes the method of reacting oxirane-containing compounds with carboxyl-containing compounds, preferably at temperatures at or around ambient, in the presence of active chromium III tricarboxylate salts which have unoccupied coordination sites. More specifically this patent describes the preparation of catalytically active chromium III-tricarboxylates from normally catalytically inactive chromium III tri-carboxylate hydrates. These compounds are powerful catalysts for the reactions of oxirane compounds with both organic carboxylic acids and cyclic primary imides.

Preparation of 2-hydroxyalkyl esters

This patent describes a method of catalyzing the reaction of organic polybasic acid anhydrides with at least one oxirane which comprises carrying out the reaction in the presence of an effective catalytic amount of a synergistic catalyst mixture comprising an active chromium III tricarboxylate salt having unoccupied coordination sites and any compound capable of polarizing the carboxylic acid anhydride to yield a reactive carboxylic acid moiety. Preferred compounds as the cocatalyst member include one or more members selected from the group consisting of the alkyl, aryl, aralkyl, and alkaryl tri-substituted compounds of the following types: quaternary ammonium hydroxides; quarternary phosphonium halides; arsines; amine oxides; sulfoxides; tertiary aminophenols; trihydrocarbon phosphine oxides; trihydrocarbon phosphines; tertiary amines, and combinations thereof, each alone or in combination with a phenol or other reactive promoter such as, carboxylic acids and alcohols; and compounds containing two or more co-catalytic functional groups in the same molecule such as alkyl phosphoramides, alone or in combination with any and all of (1) any of the members, (2) phenols or other reactive promoters. Also the invention pertains to a novel class of mixed catalysts which act synergistically for promoting the reaction of oxirane oxygen groups with curing (crosslinking) or chain extension agents.

Catalysts for the oxirane-anhydride reaction

This patent describes a method of catalyzing the reaction of organic polybasic acid anhydrides with at least one oxirane which comprises carrying out the reacton in the presence of an effective catalytic amount of a synergistic catalyst mixture comprising an active chromium III tricarboxylate salt haing unoccupied coordination sites and any compound capable of polarizing the carboxlyic acid anhydride to yield a reactive carboxylic acid moiety. Preferred compounds as the cocatalyst member include one or more members selected from the group consisting of the alkyl, aryl, aralkyl, and alkaryl tri-substituted compounds of the following types: quaternary ammonium hydroxides; quarternary phosphonium halides; arsines; amine oxides; sulfoxides; tertiary aminophenols; trihydrocarbon phosphine oxides; trihydrocarbon phosphines; tertiary amines, and combinations thereof, each alone or in combination with a phenol or other reactive promoter such as, carboxylic acids and alcohols; and compounds containing two or more co-catalytic functional groups in the same molecule such as alkyl phosphoramides, alone or in combination with any and all of (1) any of the members, (2) phenols or other reactive promoters. Also the invention pertains to a novel class of mixed catalysts which act synergistically for promoting the reaction of oxirane oxygen groups with curing (crosslinking) or chain extensions. agents.

Catalysts of the oxirane-anhydride reaction

Chromium salt catalysts

This patent discloses and claims the reaction of oxirane-containing compounds with primary cyclic imide-containing compounds, at temperatures of from about 0.degree. to 225.degree.C, in the presence of active chromium III tricarboxylate salts which have unoccupied coordination sites.

Imide oxirane reactions

Mobile mixtures of an oxirane compound and a labile hydrogen compound such as an acid, anhydride, imide or sulfonimide can be stored at long periods of time under ambient conditions in the presence of a latent chromium III chelate. At an elevated temperature, the catalyst is activated and rapidly converts the mixture into a more advanced state of cure.

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Fair Oaks, CA, United States of America

Roger B Steele