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Poly(N,N-diallylaspartic acid-alt-sulfur dioxide): its synthesis and application

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Abstract

Monomer pairs, dimethyl N,N-diallylaspartate hydrochloride [(CH2=CH–CH2)2NH+CH(CO2Me)CH2CO2Me Cl−] (I)/SO2 and N,N-diallylaspartic acid hydrochloride [(CH2=CH-CH2)2NH+CH(CO2H)CH2CO2H Cl−] (II)/SO2, underwent alternate cyclocopolymerization to give cationic polyelecyrolytes (CPEs), poly(I-alt-SO2) (III) and poly(II-alt-SO2) (IV), respectively, in very good yields. (+) III upon acid hydrolysis was converted to cationic (+) IV, bearing in each repeating unit the triprotic acid residues [(NH+…(CO2H)2] of aspartic acid hydrochloride. Under the influence of pH, (+) IV has been equilibrated to water-insoluble diprotic polyzwitterionic acid (±) V, water-soluble monoprotic poly(zwitterion-anion) (± −) VI and finally its conjugate base polydianion (=) VII. Basicity constants of CO2 − and amine group have were determined. The pH-responsive polymer was demonstrated to be an efficient antiscalant against CaSO4 scaling. For potential separation and purification of biomolecules, a recyclable aqueous two-phase system (ATPS) was constructed using water-soluble (=) VII and urethanized polyvinyl alcohol; the ionic polymer can be recycled by precipitating it as (±) V at a lower pH.

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Acknowledgments

This project was funded by the National Plan for Science, Technology and Innovation (MAARIFAH), King Abdulaziz City for Science and Technology, through the Science & Technology Unit at King Fahd University of Petroleum & Minerals (KFUPM), the Kingdom of Saudi Arabia, award number (11-ADV2132-04). The authors gratefully acknowledge the facilities provided by KFUPM.

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  1. Chemistry Department, King Fahd University of Petroleum and Minerals, Dhahran, 31261, Saudi Arabia

    Shaikh A. Ali & Zakariyah A. Jamiu

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  1. Shaikh A. Ali
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  2. Zakariyah A. Jamiu
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Correspondence to Shaikh A. Ali.

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Ali, S.A., Jamiu, Z.A. Poly(N,N-diallylaspartic acid-alt-sulfur dioxide): its synthesis and application. Polym. Bull. 73, 2179–2198 (2016). https://doi.org/10.1007/s00289-016-1602-x

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  • DOI: https://doi.org/10.1007/s00289-016-1602-x

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