Preparation and Properties of N-Methylol, N-Alkoxymethyl and N-Alkylthiomethyl Polyamides

Abstract

The pyrolysis method used previously to transform the acetyl derivatives of N,N-dimethyllactamide into , -dimethylacrylamide was applied to the preparation of other N-alkyl acrylamides and methacrylamides. N,N-Diethylacrylamide was obtained in good yield by the thermal decomposition of N,N-diethyl-a-acetoxypropionamide, but pyrolysis of N-methyl-and N,N-di-ro-butyl-acetoxypropionamide was less satisfactory for the preparation of the corresponding acrylamides.N-Methyl-and N,N-dimethylmethacrylamides were made successfully by pyrolyzing the corresponding N-alkyl -acetoxyisobutyramides. Apparently methacrylamides can be made more readily than acrylamides by the pyrolysis method.Philadelphia 18, Pennsylvania

Recent advances in electrochromic polymers

“…Cairns et al [41] synthesised polyamides that can be converted to the N-mercaptomethyl form by redox reactions with formaldehyde, but it took until 1995 for the first electrochemical study of polyamides to be conducted by Tsutsumi et al [42], who also continued studying the electrochemical behaviour of polyamide-containing disulphide bonds [43] in 1996. A year later, in 1997, Agrawal et al [44] prepared EC polymeric solid films from in situ electromagnetic radiation of a low viscosity EC monomer, which includes polyamides.…”

The case against using soluble nylon in conservation work

“…These chains pack together so that the oxygen atoms of one molecule are opposite the -NH groups of an opposite molecule providing abundant opportunity for the formation of hydrogen bonds between adjacent chains. This results in very high interchain forces [2]. It was subsequently found that by chemically modifying these nylons a wide variety of polymers could be produced with vastly different properties from the parent nylons.…”

“…The commonest modified nylons are N-alkoxymethyl derivatives [22]. These are produced when nylons are reacted with formaldehyde and an alcohol or mercaptan in the presence of an acid to substitute alkoxymethyl groups on the nitrogen atom [2,3]:…”

Fiber structure-property relationships: a disulfide-crosslinked self-crimping polyamide

“…E arly work by Cail'l1s and coworkers [4,5] describ ed the prep aration and so me properties of Nm ethylol, N-alkoxymethyl, and N -alkylthiom ethyl polyamides. Al though th ese reactions were carried out while the polymers were in the dissolved state, they are of interest as potential precursors for crosslinking.…”

“…of strong acids, producing an N -methoxy-methylated polycaprolactam (II). Th e structure of t hi s product has already been es tablished [4] from the facts (a) N -m ethoxy-methyl ated polyamides produce form aldehyde in good agreement with the expected quantities predicted from m ethoxyl analyses, (b) polyarnides prepared from N,N'-alkylated diamines do not r eact wi th the hemiacetal of form aldehyde and methyl alcohol, and (c) infrared absorption spectroscopy indicates a substantial decr ease in th e intensity of cer tain -NH absorption bands in th e N -methoxy methylated polyamides.…”