The Dow Chemical Company

John W Bozzelli

Kent S Dennis

George D Shier

Felipe A Donate

Nancy J Morris

Charles W Martin

Roberta C Cheng

Roscoe L Pearce

Nancy B Tefertiller

Thomas W Regulski

Sharon L Oriel

Donald N Bremer

A process is disclosed for the chemical immobilization of biological material such as bacteria and enzymes containing an active hydrogen with a vinyl addition polymer of an isocyanatoalkyl ester of an ethylenically unsaturated carboxylic acid. The vinyl addition polymer is versatile in that it can be copolymerized with varying amounts and types of comonomers.

Immobilization of biological matter via copolymers of isocyanatoalkyl

1,3-pentadiene is polymerized from a mixture of saturated and unsaturated hydrocarbon compounds, the compounds having primarily 5 carbon atoms per molecule, with an anionic polymerization initiator. The mixture of saturated and unsaturated hydrocarbon compounds is contacted, in an inert atmosphere, with an anionic polymerization initiator to form a reaction mixture. The anionic polymerization initiator is present in an amount sufficient to inactivate polymerization-terminating compounds present in the mixture and to initiate polymerization of 1,3-pentadiene from the mixture. The reaction mixture is heated with stirring to a temperature sufficient to inactivate the polymerization terminating compounds. After inactivation of the polymerization terminating compounds, the reaction mixture is then heated with stirring to a temperature sufficient to initiate polymerization of 1,3-pentadiene from the reaction mixture. Polymer recovery and subsequent functionalization, if any, follow thereafter.

Anionic polymerization of cis- and trans-1,3-pentadiene from a mixture

1,3-Pentadiene is polymerized in an inert gaseous atmosphere from a mixture of saturated and unsaturated hydrocarbon molecules. At least 50 percent by weight of said molecules have 5 carbon atoms. An anionic polymerization initiator in conjunction with an organic polar solvent is used to effect polymerization. Cyclopentadiene, active hydrogen compounds and other polymerization-terminating compounds may be inactivated and separated from the mixture of hydrocarbon compounds before starting polymerization. As an alternative, inactivation and separation of cyclopentadiene, active hydrogen compounds and polymerization-terminating compounds may be omitted provided the anionic polymerization initiator is employed in an amount to (a) inactivate such compounds and (b) initiate polymerization of 1,3-pentadiene. The polymer of 1,3-pentadiene so prepared is then hydrogenated or functionalized by further reaction.

Curable compositions containing (1) an epoxy resin containing a plurality of active hydrogens and (2) and addition polymer of an isocyanatoalkyl ester of an .alpha., .beta.-ethylenically unsaturated carboxylic acid such as 2-isocyanatoethyl methacrylate are usefully employed as coatings for metal substrates and in other applications which require hard surface coatings exhibiting resistance to chemicals and light.

Epoxy resin coating compositions

Quaternary ammonium salts of the formula ##STR1## where R, R', R' and R'' are typically individually alkyl or inertly-substituted alkyl radicals and Y.sup..crclbar. is a neutralizing anion, are facilely prepared by amidating the carbonyl carbon and subsequently quaternizing the ring nitrogen of an N-alkyl morpholinone. These quaternary ammonium salts demonstrate biological, antistatic and surfactant activity.

Method of preparing quaternary ammonium salts from various morpholinones

Quaternary ammonium salts of the formula ##STR1## where R, R' and R' are typically individually alkyl or inertly-substituted alkyl radicals and Y.sup..crclbar. is a neutralizing anion, are readily prepared by quaternizing the nonamide ring nitrogen of an N-alkyl piperazinone. These quaternary ammonium salts demonstrate biological activity.

Oxopiperazinium salts, their preparation and their use

Relatively large amounts of initiator and short reaction times produce high molecular weight copolymers of phenylmaleic anhydride with a monomer such as styrene whereas normally these conditions would be expected to produce low molecular weight copolymers. Additionally, it was found that the molar ratio of phenylmaleic anhydride and comonomers such as styrene should be controlled to about 1:3 to 1:6 to obtain the high molecular weight desired. Limited use of inert solvents is possible.

High molecular weight polymers of phenylmaleic anhydride

Hydrogen sulfide and lower alkyl mercaptans are selectively extracted from a gas stream by contacting the stream with piperazinone or an alkyl substituted piperazinone which may contain a substantial proportion of water. The absorbed sulfur compounds can be regenerated by heating the extraction liquid to about 85.degree.-150.degree. C.

Absorption of sulfur compounds from gas streams

The hydrolysis of carbon oxysulfide is catalyzed by piperazinone and alkyl-substituted piperazinones at ambient or below ambient temperatures. The hydrolysis step can be combined with a sour gas purification process in the treatment of refinery gases, coal gasification streams, and other such gases which contain COS and other acidic contaminants.

Hydrolysis of carbon oxysulfide

Morpholinones are efficient selective solvents for aromatic hydrocarbons from hydrocarbon mixtures containing same. For example, N-methyl-3-morpholinone is an efficient selective solvent for benzene, toluene, and xylene from a hydrocarbon stream obtained from a catalytic reformer.

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Midland, MI, United States of America

John W Bozzelli