Preparation of high molecular weight compounds on the basis of cyclic imides and diimides of dicarboxylic acids

Abstract

Investigation has been conducted in two directions: incorporation of the imide cycles into the macromolecule owing to the reactivity of double bonds, and preparation of polyamides involving the aminolysis of the imide cycles. Citraconimides are shown to polymerize by radical mechanism forming linear macromolecules consisting of the imide cycles. At the initial period the polymerization rate is proportional to the square root of the initiator concentration. The absolute values of the polymerization rates are low. Conversions attains 3% for 75 min. at 70°C. with 0.102 × 10−3 mole/liter of the initiator. The intrinsic viscosities are 0.07–0.1% Low polymerization rates and low molecular weights are due to the structure of this cyclic derivative of 1,2,2‐substituted ethylene with the methyl group at the double bond. An attempt to polymerize N‐methylcitraconimide by UV irradiation resulted in the formation of a mixture of crystalline oligomers; a tetramer was isolated and characterized. Migration copolymerization of diamines with diimides of unsaturated and saturated acids was also investigated. It was shown that the reaction depends on pH of the medium. In neutral medium in the absence of water diamines are added to the double bonds of maleindiimides forming poly‐alkylene‐polyimides of asparagic acid. In aqueous alcohol at pH 9–9.5 aminolysis of succinimides occurs and mixed polysueeinamides are formed with regular structure and molecular weight up to 20,000.

Fixation on Wool of Dyes Containing a Maleimide Group

“…Comparison of the infrared spectra of the original dye and the dye hydrolysis product showed the disappearance of the peaks characteristic for -%=Oh a five-membered ring [11,12]. Dye I was heated in buffer solutions of pH 3, 4, 5 and 6 at 80°C and 100°C and samples examined after various times using t.1.c.…”

“…Elemental analysis was inconclusive, as the composition did not differ significantly from that of the original dye. Comparison of the infrared spectra of the original dye and the dye hydrolysis product showed the disappearance of the peaks characteristic for -%=Oh a five-membered ring [11,12]. This indicates that the hydrolysis is a ring-opening reaction as shown in Eqn 3.…”