A Combinatorial Approach to Studying the Effects of N-Alkyl Groups on Poly(N-alkyl and N,N-dialkylacrylamide) Solubility

Abstract

Soluble polymers including poly(N-alkylacrylamide)s with low mole percent loadings of pendant groups are of interest in applications in catalysis, synthesis, sequestration, and soluble affinity chromatography where their thermal and phase-dependent solubility facilitates purification and separation. This work describes a library synthesis and study of the effects of polymer composition on the phase-selective solubility of dye-labeled poly(N-n-octadecylacrylamide-co-N-n-butylacrylamide) copolymers. To study the relative importance of n-octadecyl versus n-butyl groups, copolymers with different ratios of n-octadecylacrylamide and n-butylacrylamide but with similar degrees of polymerization and polydispersity were prepared by a split-pool synthesis using a highly soluble poly(N-acryloxy-2-dodecylsuccinimide) as the precursor. Polymer sequestrants were used to remove excess amines and the byproduct N-hydroxyl-2-dodecylsuccinimide without fractionation of the polyacrylamides. Other studies of dye-labeled poly(N,N-dialkylacrylamide)s prepared by the polymerization of N,N-dialkylacrylamides with methyl, ethyl, propyl, butyl, pentyl, and hexyl N-alkyl groups in a variety of thermomorphic or latent biphasic polar/nonpolar solvent mixtures showed that poly(N,N-dialkylacrylamide)s like poly(N-alkylacrylamide)s have phase-selective solubility that is highly dependent on the size of the N-alkyl group.

Synthesis and characterization of novel twin‐tailed hydrophobically associated copolymers and their applications to Cr(III) removal from aqueous solutions

“…2,2′‐Azobis (2‐methylpropionamidine) dihydrochloride (AIBA, Qingdao Run Xing Photoelectric Materials Co.) and sodium dodecyl sulfate (SDS, Shanghai Chemical Reagent Co.) were used as received. The twin‐tailed hydrophobic monomer N,N ‐dibutylmethacrylamide (DBMAAM, 90%) was prepared according to the literature ; 1 H‐NMR (400 MHz, D 2 O): δ 0.95–0.98 (6H, t, N(CH 2 CH 2 CH 2 CH 3 ) 2 ), 1.30 (4H, m, N(CH 2 CH 2 CH 2 CH 3 ) 2 ), 1.55 (4H, m, N(CH 2 CH 2 CH 2 CH 3 ) 2 ), 3.30–3.38 (4H, t, N(CH 2 CH 2 CH 2 CH 3 ) 2 ), 1.95 (3H, s, CH 3 C), 4.95, 5.12 (2H, d, d, CH 2 ). Analytical reagents were used as received (Kermel).…”

“…2,2 0 -Azobis (2-methylpropionamidine) dihydrochloride (AIBA, Qingdao Run Xing Photoelectric Materials Co.) and sodium dodecyl sulfate (SDS, Shanghai Chemical Reagent Co.) were used as received. The twin-tailed hydrophobic monomer N,N-dibutylmethacrylamide (DBMAAM, 90%) was prepared according to the literature 19…”

Synthesis, Characterization and Properties of Hydrophobically Modified Polyacrylamides

“…The hydrophobic twin-tailed monomers (DOMAM) were synthesized using a process similar to originally described by McCormick et al 12 and others 13,14 . 10 mmol L -1 di-n-octylamine was initially dissolved Asian Journal of Chemistry; Vol.…”

Using Soluble Polymer Supports To Facilitate Homogeneous Catalysis

“…220,221 For example, in contrast to PNIPAM, poly(N-octadecylacrylamide) (PNODAM) is a lipophilic polymer that has heptane solubility. We prepared PNODAM-supported phosphine and SCS ligands using a procedure like that used earlier to prepare PNIPAM derivatives.…”