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STABLE FREE RADICAL POLYMERIZATION PROCESS BASED ON THE OXIDATION OF HINDERED AMINES AND THE THERMOLYSIS OF N-OXIDES

IP.com Disclosure Number: IPCOM000027397D
Original Publication Date: 1996-Aug-31
Included in the Prior Art Database: 2004-Apr-07
Document File: 2 page(s) / 88K

Publishing Venue

Xerox Disclosure Journal

Abstract

Disclosed is Stable Free Radical Polymerization (SFRP) a process modification whereby the critical nitroxide species used is made in situ by the oxidation of a tertiary amhe or the thermolysis of an N-oxide. The main advantages of in situ generation is a saving on the high cost of the nitroxide species.

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XEROX DISCLOSURE JOURNAL

STABLE FREE RADICAL Proposed Classification POLYMERIZATION PROCESS BASED ON
THE OXIDATION OF HINDERED AMINES

Peter M. Kazmaier Michael K. Georges Richard P. N. Veregin Barkev Keoshkerian Gordon K. Hamer Karen A Moffat Marko D. Saban

U. S. C1.430/110 Int. C1. G03g 09/97

AND THE THERMOLYSIS OF N-OXIDES

Disclosed is Stable Free Radical Polymerization (SFRP) a process modification whereby the critical nitroxide species used is made in situ by the oxidation of a tertiary amhe or the thermolysis of an N-oxide. The main advantages of in situ generation is a saving on the high cost of the nitroxide species.

Stable free radicals such as TEMPO enable the preparation of a wide variety of resins with narrow polydispersities and enable the preparation of block copolymers by a free radical process. Although the process works very well, the cost of the Stable Free Radical (SFR) coreagents is somewhat high and adds to the cost of the resin.

Process for Preparing Tertiary Amine

Amine, 2,2,6,6-tetramethylpiperidine (1 mol), benzophenone (1 mol), toluenesulfonic acid (1 g) and toluene (100 mL) are heated to reflux for 1 hour. After cooling, excess methanolic sodium borohydride is added and the mixture is poured into water (300 mL) and extracted with diethyl ether (3x50 mL). After drying over sodium sulfate and evaporation of the ether, the product is isolated and purified by distillation under high vacuum.

Oxidation of Tertiary Amine with Hvdrogen Peroxide...