Synthesis and properties of polyamides derived from anhydro‐ and dianhydroalditols

Abstract

The three isomeric 1,4:3,6-dianhydroalditols with D-gluco-(2), D-manno-(11) and L-id0 (17) configuration and both 1,4-anhydroalditoIs with threo (22) and erythro (27) configuration were efficiently transformed into the corresponding diamino derivatives. Interfacial polycondensation of these chiral heterocyclic diamines with purchasable aromatic and aliphatic carboxylic acid chlorides gave polyamides 35 and 36a-f, 37, 38 and 39a-d. The polymers were characterized using IR and 'H/13C NMR spectroscopy. Number-average molecular weights were obtained from gel-permeation chromatography to be an = 5 000-25 000 corresponding to a number-average degree of polymerization up to Fn = 100. Inherent viscosities were measured, and differential scanning calorimetry gave information on the thermal properties of the polymers. 0 1991, Huthig & Wepf Verlag, Base1 CCC 0025-1 16)</91/$05.00 ( 32 R = NH2.HCI 29 R' = H, R2 = Ts 30 R' -B z j R 2 = H 29 3 3 R = H b, ( 3 4 R = Ts a1 H,SO,/heat bl TsCl/pyridine I T s = C H 3~~)

A highly rigid diamine monomer derived from naturally occurringmyo-inositol and its use for polyamide synthesis

“…In the thermograms of polyamide 6a , a glass transition was observed at 160 °C. This T g was much higher than those reported (ranging 50 − 130 °C) for the polyamides obtained by polycondensation of the isohexide‐derived diamines with sebacoyl chloride, indicative of the increased stiffness of the polymer main chain due to the highly rigid 5‐6‐5 fused ring system. The T g of polyamide 6d was high, at 270 °C.…”

“…In addition, isohexides have been derived into amino‐functionalized compounds . Among these, diamines have been used as monomers for the preparation of polyamides with several advantageous properties such as high T g 's and semicrystallinity, making them suitable for engineering applications …”

Computed tomography coronary angiographic demonstration of a single coronary artery with the right coronary artery arising as a continuation from the left circumflex coronary artery

“…Among the numerous publications dealing with polymers based on 1 , only a limited number of them are devoted to polyamides. Thiem and Bachmann15 thus carried out the interfacial polycondensation of terephthaloyl or isophthaloyl chlorides with 2,5‐diamino‐1,4:3,6‐dianhydro‐2,5‐dideoxy‐ D ‐sorbitol dihydrochloride to obtain the corresponding polyamides.…”

Polymers with shape memory effect from renewable resources: crosslinking of polyesters based on isosorbide, itaconic acid and succinic acid

“…It is also reported that the use of catalysts like Lewis acids or enzymes is indispensable for successful polycondensations of isosorbide with diacids. Isosorbide is an interesting monomer too for the synthesis of aromatic polyesters, polyamides, polyurethanes and polyethers …”