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TONER RESINS FROM ZIEGLER-NATTA POLYMERIZATION OF FUNCTIONAL OLEFINS

IP.com Disclosure Number: IPCOM000026411D
Original Publication Date: 1991-Oct-31
Included in the Prior Art Database: 2004-Apr-05
Document File: 2 page(s) / 139K

Publishing Venue

Xerox Disclosure Journal

Abstract

Toner resins from Ziegler-Natta polymerization of functional olefins that are useful in electophotographic toner compositions are disclosed. The toner compositions are comprised of semicrystalline copolymer resin particles with a melting point of from about 30 "C to about 100 "C and contain functional groups comprising, for example, hydroxy, carboxy, amino, amido, ammonium or halo, and pigment particles.

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XEROX DISCLOSURE JOURNAL

TONER RESINS FROM ZIEGLER- NATTA POLYMERIZATION OF U.S. C1.430/109 FUNCTIONAL OLEFINS
Timothy J. Fuller
Stephan Drappel
Thomas W. Smith
Michael J. Levy
Richard B. Lewis
Ralph W. Moser

Proposed Classification

Int. C1. GOlg 09/08

Toner resins from Ziegler-Natta polymerization of functional olefins that are useful in electophotographic toner compositions are disclosed. The toner compositions are comprised of semicrystalline copolymer resin particles with a melting point of from about 30 "C to about 100 "C and contain functional groups comprising, for example, hydroxy, carboxy, amino, amido, ammonium or halo, and pigment particles.

Toner resins from Ziegler-Natta polymerization of functional olefins include copolymers of type poly(A,-B,), wherein n is a number of from 10 to about 21,000; and m is a number of from 10 to about 21,000. For example, the following pairs of A and B monomers maybe copolymerized, wherein A is eicosene and B is selected from the group comprising: styrene, undecylenyl alcohol, undecylenyl halides, undecylenic acid, idodoeicosene, undecylene quaternary ammonium salts, aminoundecylene, amidoundecylene, trialkylsilyl undecylenic acid esters, amidoeicosene, alkyl undecylenate, undecylenic acid metal salts, undecylenyl halide incorporating side chains of graft polyethyloxazoline.

The copolymers are prepared by Ziegler-Natta polymerization of the alkene eicosene with olefinic monomers such as styrene, undecylenyl chloride, bromide, and iodide, undecylenyl alcohol (as the trimethyl silyl ether); and undecylenic acid (as the trimethyl silyl ester). The catalyst used is TiC13- AA/Et2AlCl, a highly specific isotactic catalyst for the polymerization of alpha-olefins. The polymerization reactions are generally carried out by preparing an anhydrous solution of the olefin monomers, thereafter adding catalytic amounts of, for example a toluene solution containing diethyl aluminum chloride, and then titanium trichloride. Stirring under inert atmosphere for several hours followed by quenching with, for example methanol, and precipatating with acidic methanol affords the copolymer product. Amino-, amido-, and quaternary ammonium salt- derivatives are prepared by nucleophilic substitution reactions of mines on halo- containing monomers such as undecylenyl iodide and p...