Browse Prior Art Database

NOVELTLC POLYESTERS BY MELT POLYESTERIFICATION

IP.com Disclosure Number: IPCOM000026485D
Original Publication Date: 1992-Apr-30
Included in the Prior Art Database: 2004-Apr-06
Document File: 4 page(s) / 145K

Publishing Venue

Xerox Disclosure Journal

Abstract

A process for the preparation of novel thermotropic liquid crystalline (TLC) polymers for use in ultra low melt toner compositions is disclosed. The process comprises formation of a mesogenic diester unit followed by a melt polyesterification of the mesogenic diester unit with diols.

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XEROX DISCLOSURE JOURNAL

NOVELTLC POLYESTERS BY Proposed Classification MELT POLYESTERIFICATION U.S. C1.430/106.6
Bik
Wah Anissa Yeung Int. C1. G03g 09/83 Lupu Alexandru

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XEROX DISCLOSURE JOURNAL - Vol. 17, No. 2 March/Aprill992 115

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NOVEL TLC POLYESTERS BY MELT POLYESTERIFICATION

(Cont'd)

A process for the preparation of novel thermotropic liquid crystalline (TLC) polymers for use in ultra low melt toner compositions is disclosed. The process comprises formation of a mesogenic diester unit followed by a melt polyesterification of the mesogenic diester unit with diols.

TLC polymers have unique properties resulting from ordering of the TLC molecules in a melt mesophase. These materials have been prepared previously by conventional solution polymerization processes but may be accompanied by complications such as low yields and high cost. A mesogenic unit used previously, di(p-hydroxymethylphenyl) terephthalate, contains labile ester linkages which may undergo undesirable transesterification reactions under melt polyesterification conditions. Therefore new mesogenic units and new TLC polyester structures are required for melt polyesterification processing.

These new TLC polyester materials are better suited for ultra low melt toner applications because of their low melt temperatures, rheological and fusing properties compared to conventional toner resins.

Preparation of the Mesogenic Unit

To a solution of trans-1,4-cyclohexanedimethanol (5.0 g, 34.7 mmol) in 50 mL pyridine was added mesyl chloride (7.6 mL, 98.2 mmol) dropwise at 0°C. The mixture was allowed to stir vigorously for 16 hours, then poured into 300 mL ice cold 2 N HC1. The precipitate was collected and washed successively with 2 N HC1, water, aqueous sodium bicarbonate, and water, providing 9.7 g (95% theory) of the dimesylate of trans-l,4-cyclohexanedimethanol, mp 166°C (by DSC).

The dimesylate of trans- 1,4-trans-cyclohexanedimethanol( 10.00 g, 33.0 mmol), methyl 4-hydroxybenzoate (10.14 g, 66.7 mmol) and anhydrous potassium carbonate (11.95 g, 86.6 mmol) were mixed together in 260 mL of N,N- dimethylformamide. The mixture was heated at 120°C for 12 hours with vigorous stirring. The resulting mixture was poured into 3 liters of...