Alternating copolymers of functionalized α-methyl styrene monomers and maleic anhydride

Abstract

Alkyl and tertiary amine functionalized α-methyl styrene (AMS) monomers have been synthesized via reactive coupling of 3-isopropenyl-α,α-dimethylbenzyl isocyanate (TMI) with primary amines. Primary amines utilized include hexylamine, octadecylamine and N,N-dimethylethylenediamine to synthesize monomers,urea (AMSDMA), respectively. The structures of these functionalized AMS monomers have been confirmed by 1 H-NMR, 13 C-NMR and FT-IR. AMS, AMSC 6 or AMSC 18 was then successfully copolymerized with maleic anhydride (MalA) via free radical polymerization initiated by azobisisobutyronitrile to synthesize alternating copolymers. Free radical homopolymerizations of AMS, AMSC 6 , AMSC 18 and MalA were performed to reveal no monomer conversion by gas chromatography and no formation of polymer chains by gel permeation chromatography (GPC). Alternating copolymers were characterized by GPC, 1 H-NMR, FT-IR and MALDI-TOF MS. Finally, post-polymerization modification of P[(AMSC 18 )-a-(MalA)] by imidization of the MalA repeat unit with a primary amine was performed. This leads to the synthesis of alternating dual functionalized copolymers in an efficient and simple way. † Electronic supplementary information (ESI) available. See

Orthogonal Click Postfunctionalization of Alternating Copolymers Prepared by Nitroxide‐Mediated Polymerization

“…Alternating radical polymerization has been achieved with nearly perfect sequence control . Along these lines, we have recently introduced alternating nitroxide‐mediated polymerization (NMP) of 1,1,1,3,3,3‐hexafluoroisopropyl acrylate (HFIPA) 1 and (7‐octenyl)vinyl ether (OVE).…”

Comparison of the Kinetic Hydrate Inhibition Performance of Block and Statistical N-Alkylacrylamide Copolymers

“…11 In addition, sterically bulky monomers or polymerization transition states involving transition metals can lead to more ordered monomer sequences in the resulting copolymer. 12 We have recently employed an aqueous single electron transfer living radical polymerization (SET-LRP) to synthesize multiblock homopolymers and copolymers of a range of acrylamide monomers including N-isopropylacrylamide (NIPAM), 2hydroxyethyl acrylamide (HEAA), N,N-dimethylacrylamide (DMA), and N,N-diethylacrylamide (DEA) (Figure 2). 13 This allows for an entry point to study the KHI performance of block vs statistical copolymers of these acrylamides.…”