Methyl 10,11-epoxyundecanoate was copolymerized with propane oxide and 1-butane oxide using a modified aluminumalkyl/water/acetylacetone (1:0.5:1) initiating system. Hydrolyses of the copolymers to a series of ionomers containing 10, 5, 2, and 1 mol.-% sodium carboxylate groups were accomplished.
EXPERIMENTAL
Purification of Solvents and Reagents10-Undecenoic acid was esterified to methyl 10-undecenoate, which was epoxidized to MEU with m-chloroperoxybenzoic acid.PO was refluxed for 30 min over calcium hydride, then distilled (b.p., 34°C) and stored at 5°C. BO was heated to reflux for 12 h over calcium hydride, then distilled (b.p., 63°C).AcAc was heated over phosphorous pentoxide, fractionally distilled (b.p., 139°C), and stored under nitrogen. 92 VOGL AND KILIMAN Downloaded by [Dalhousie University] at 15:59 26 December 2014 POLY(ALKYLENE OXIDE) IONOMERS 93
Polymeric esters and amides were prepared from the imidazolids of poly(10undecenoic acid, poly(10,11-epoxyundecanoic acid) and, poly(5,6-epoxyhexanoic acid. They include polymeric reaction products of 4-hydroxybisphenol, 4-cyano-4'-hydroxybisphenol, 4-aminobisphenol, cholesterol, and carbazole. The reactions were carried out via the imidazolids of the polyacids and gave yields between 75% to quantitative with conversions from 60-100%. Aromatic amines gave nearly quantitative conversion; for quantative substitution with alcohols, their alkali salts should be used. The polymeric esters and amides were briefly studied for their thermal and mesogenic properties.
The two most accessible ω-undecanoates, 5-hexenoate and 10-undecenoate have been epoxidized to the corresponding 5,6-epoxyhexanoate and improved polymerization techniques have allowed a large-scale production of the polymers. Quantitative hydrolysis made the polymeric acids available for their transformation with diimidazolylcarbonyl to the highly reactive polymeric carboxylic acids imidazolids.
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