Polyureas from carbon dioxide and diamines by means of triphenyl phosphite and pyridine hydrochloride

Abstract

SynopsisThe reaction of carbon dioxide with aniline using triphenyl phosphite in pyridine is greatly facilitated by the addition of hydrochlorides of tertiary amines such as pyridine and triethylamine, and has been successfully applied to the preparation of polyureas of high molecular weight from carbon dioxide and aromatic diamines. The presence of a catalytic amount of pyridine hydrochloride significantly increased the inherent viscosity of the resulting polymers, the highest value being obtained with about an equivalent of the chloride. Optimal temperatures and pressures varied with diamines used, and were M " C and 40-50 atm of carbon dioxide. The polycondensation reaction was also affected by the solvent compositions of pyridine and N-methylpyrrolidone, its optimum being dependent on diamines used.

Copolymerizations of carbon dioxide and epoxides in the presence of rare earth coordinate catalyst

“…Structure of copolymer epoxide-CO 2 IR analyses were made for the synthesized copolymer. It was found that there were characteristic absorption peaks for carbonyl and COO of the carbonate group for every polymer around 1750 and 1260 cm…”

“…1 Over the past several years, large advances have been made in the development of CO 2 for polymer synthesis applications. [2][3][4][5][6][7][8][9][10] It is a new and important research area in C1 chemistry.…”

Synthesis of Polyurea via the Addition of Carbon Dioxide to a Diamine Catalyzed by Organic and Inorganic Bases

“…[14] Recently, a new route was reported for the nonisocyanate polyurea synthesis by using dicarbamates and diamines as monomers. [8e,10a-c,17] Polyurea was also synthesized via addition of CO 2 to diamine compounds under catalytic conditions, using triphenyl phosphate, [18] ethylene chlorophosphite, [19] ionic liquid., [10d,20] and inorganic base [17c] as catalysts. [16] Our group synthesized a series of polyureas using CO 2 and diamine without catalyst.…”

Manufacturing and Properties of Aramid Reinforced Composites

“…Another polymerization scheme towards aramids not requiring transformation of the diacid into the more expensive and difficult to handle diacyl chlorides is possible with the so-called condensing agents. The latter, being derived from phosphorus and sulfur containing compounds, activate the aromatic acid in situ during polymerization [12]. The reaction has not been utilized commercially because the costs of recovering and regenerating the condensing agents by far outweigh the cost advantage of using unmodified diacids.…”