Reilly Industries, Inc.

Reilly Tar and Chemical Corporation

James G Keay

Eric F Scriven

Gerald L Goe

Ramiah Murugan

Donald W McQuigg

Edward E Sowers

James R Stout

Michael L Prunier

Steven J Quimby

Tony Yantao Zhang

Ernest Crowe

Lowell M Huckstep

H.sub.2 O.sub.2 -catalyzed polymerizations for linear polyvinylpyridines

Processes for preparing pyridyl-substituted hydrazoles, dihydrothiadiazones or aminotriazinones by reaction of iminopyridines preformed in situ or otherwise with hydrazides or carbazides, or their sulfur counterparts, or with aminotriazinones.

Preparation of hydrazones, dihydrothiadiazoles and triazinones

Imines are synthesized by the hydrogenation of pyridinecarbonitriles with amines in the presence of a rhodium-loaded catalyst. The resulting imines are stable and may be transiminated and then hydrogenated to form selected secondary amine products or may be hydrolyzed to aldehydes. Further, a very useful class of unsymmetrical secondary amines represented by the formula RCH.sub.2 NHAr (in which R is not aliphatic and Ar is aromatic and not attached to R), which has heretofore been accessible only with some difficulty, can be synthesized by processes herein disclosed utilizing the reductive intermolecular coupling of nitriles and primary aromatic amines.

Processes for the synthesis of unsymmetrical secondary amines

Described are preferred processes for producing linear polyvinylpyridines. The processes involve the use of hydrogen peroxide to initiate polymerization of vinylpyridine monomers in an alcohol/water solvent. Processes of the invention provide good reaction rates and conversions, and are particularly advantageous in achieving control of the M.sub.w 's of the final product polymers.

H2O2-catalyzed solution polymerizations for linear polyvinylpyridines

Described are unique polymerization processes for preparing linear polyvinylpyridine polymers as well as unique linear polyvinylpyridine polymer compositions. The processes involve the use of an alkylpyridine anion as an anionic polymerization catalyst and result in linear polyvinylpyridines having alkylpyridine end groups homologous to the pendant pyridines of the polymer. Processes of the invention are particularly advantageous in preparing relatively low molecular weight linear polyvinylpyridines without the need to use large amounts of catalyst to achieve the same.

Linear polyvinylpyridine polymers and processes

Processes for the synthesis of imines, aldehydes, and unsymmetrical

A cross-linked polymer-supported 4-(N-benzyl-N-methylamino) pyridine material and process for its preparation in high yield and having effective physical and catalytic properties. The polymer supported catalyst is characterized by the suspension copolymerization of an organic phase containing the corresponding vinyl-substituted pyridine monomer, a styrene monomer, and a suitable cross-linking agent and free radical-generating catalyst in the presence of an aqueous phase containing a cellulose ether derivative as the stabilizing agent. A purified acid salt of the vinyl-substituted pyridine monomer useful in polymerizations and stable for storage as either a solid or an aqueous solution.

4-(N-benzyl-N-methylamino)pyridine acid salts and use in preparation of

A cross-linked polymer-supported 4-(N-benzyl-N-methylamino) pyridine material and process for its preparation in high yield and having effective physical and catalytic properties. The polymer-supported catalyst is characterized by the suspension copolymerization of an organic phase containing the corresponding vinyl-substituted pyridine monomer, a styrene monomer, and a suitable cross-linking agent and free radical-generating catalyst in the presence of an aqueous phase containing a cellulose ether derivative as the stabilizing agent. A purified acid salt of the vinyl-substituted pyridine monomer useful in polymerizations and stable for storage as either a solid or an aqueous solution.

A process for preparing a 4-amino-1,2,4-(4H)triazole derivative compositions having the formula ##STR1## wherein R is hydrogen or an alkyl group containing from 1 to about 10 carbon atoms, which alkyl group can be additionally substituted by one or more aryl, heteroaryl, hydroxy, or alkenyl substituents, comprising the step of reacting hydrazine or an aqueous hydrazine solution with a carboxylic acid having the formula RCO.sub.2 H in the presence of an insoluble polymer containing acidic functional groups sufficiently strong to cause the reaction to proceed under mild conditions to produce a product of high yield and purity.

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Indianapolis, IN, United States of America

James G Keay