Oxyethylation of carbochain and heterochain polyamides

Abstract

Carbochain and heterocha in polyamides are highly reactive compounds, and can be rather easily t ransform ed in to various polymer a na log whi ch in clude t hose with graft side cha ins. Thus, heterochain polyamides during reaction with formaldehyde in the presence of an acid or base, or in the presence of alcohol a nd mercaptan, easily fo rm, accordingly, N-methyl, N-alkoxymethyl, and N -alkylthiomethyl deri vatives. 1 In a reaction with ethylene ox ide, there a re formed graft N -oxyethylated derivatives of heterochain pol yam ides. 2Carbochain polyamides (fo r example, polyacry lamide and its homolog ') are capable of a ll reaction s of an amide group. Thu~, there are such polymer-a na log reactions of polyacrylamide and its homologs as saponification, imide formation , reaction with formald ehyde, reaction with forma ldehyde and a sulfite, reaction with sodium hypoch lori te (Hoffma n reaction), reaction with carboxyli c acid anhydrides, etc. 3 We inve tigated the regularity of oxyethylation of so me hetcroehain and carbochain polyamides having different structures a nd t he dependence of the physicochemi cal an d mechani cal properties upon t he content of ethylene oxide unit .The oxyethylation reaction wa studied under heterogeneous conditions. As the original heterocbain polyamides we selected polycaprolactam film s and powder, films of a mixed polyamide (Anide G-669), a filam ent (both oriented and unoriented) of polycaprolactam (Capwn) , polyhexamethylenc adipamide (Anid) , and a polyam ide from thiodivaleric ac id and hexamethylen<'diamine.We obtai ned oxyethylated polyamides containing from 5 to 54% polyethylene oxide.The use of a large exce s of ethy lene oxide promotes the synthesis of polyoxyethylated polyamides whieh have a high co ntent of polyethylene oxide.As indicated by the evenness of swell ing, the polyoxyethylation of polyamide films proceeds not only on the surface, but a lso t hroughout the entire body of the film. In some in tances, there is a lso complete solubili ty of the films following the reaction. However, on the surface of the 75

Synthesis and thermal behavior of poly(ethylene oxide) poly(N‐substituted urethane)

“…Phenols, alcohols, carboxylic acids, and amines are among the active compounds mostly used. Primary amides are also frequently ethoxylated in industrial processes, whereas only a few reports on ethoxylation or alkylation of urethane are found in the literature 17–19…”

Ionic graft copolymerization. VII. Ionic graft copolymerization of β‐propiolactone onto the trunk polymers containing pyridine, amide, sulfonyl chloride, and carboxylic acid anhydride groups

“…a It is supposed that the active species (VI) has a cyclic structure by the formation of an intramolecular ion pair. Homopolymer might be obtained by reaction (9) or chain transfer reaction to monomer and graft copolymer by reaction (8) or (10). On the other hand, the electronegativity of substituted groups increases in the following order": C.5H.5-> CH-CH-> H-> CH3-> CzHs-.…”