Diallylbis(3-ethoxycarbonylpropyl)ammonium chloride: A symmetrically substituted monomer for the synthesis of an alternate zwitterionic-anionic cyclopolymer

Shaikh Asrof Ali; Shamsuddeen Abdullahi Haladu; Asma Mohammed Zamil El-Sharif

Macromolecular Research, Vol.24, No.2, 163-169, February, 2016

DOI10.1007/s13233-016-4024-6 Export Citation

Diallylbis(3-ethoxycarbonylpropyl)ammonium chloride: A symmetrically substituted monomer for the synthesis of an alternate zwitterionic-anionic cyclopolymer

Shaikh Asrof Ali^†, Shamsuddeen Abdullahi Haladu, and Asma Mohammed Zamil El-Sharif¹

Chemistry Department, King Fahd University of Petroleum & Minerals, Dhahran, 31261, Saudi Arabia
¹Chemistry Department, University of Dammam, Dammam, 31113, Saudi Arabia

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Diallylbis[(3-ethoxycarbonylpropyl)ammonium chloride] (CH2=CHCH2)2N+[(CH2)3CO2Et]2, a new symmetrical diallyl quaternary ammonium salt, has been cyclopolymerized to its cationic polyelectrolyte (CPE) (+) I having pyrrolidine rings embedded in the polymer backbone. Polymer I would exemplify for the first time a cyclopolymer with each repeating unit bearing two identical 3-carboxypropyl pendants. (CPE) (+) I upon hydrolysis afforded pH-responsive polycationic acid (+) II, which upon successive deprotonation was transformed into a polyzwitterion acid (±) III and polyzwitterion-anion (± -) IV. Because of similar degrees of polymerization for I-IV, a meaningful comparison of their solution properties was possible. While I, II, and IV demonstrated polyelectrolyte like viscosity behavior, (±) III showed anti-polyelectrolyte properties. The anionic portion in (± -) IV controlled its solution properties. Polymer (± -) IV demonstrated remarkable antiscalant behavior; at a concentration of 15 ppm, it inhibited the precipitation of CaSO4 from its supersaturated solution with a scale inhibition efficiency of ?100% even after 300 min. This study opens up the possibility of using the current polymer as an antiscalant in reverse osmosis plants.

Keywords:pH responsive polymers;cyclopolymerization;water-soluble polymers;antiscalant;calcium sulfate scale

[References]

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[2] Kudaibergenov SE, Jaeger W, Laschewsky A, Adv. Polym. Sci., 201, 157 (2006)

[3] Kwon HJ, Yasuda K, Gong JP, Ohmiya Y, Macromol. Res., 22(3), 227 (2014)

[4] Singh PK, Singh VK, Singh M, E-Polymers, 030, 1 (2007)

[5] Nag OK, Jeong JE, Nguyen TL, Woo HY, Macromol. Res., 23(5), 457 (2015)

[6] Laschewsky A, Polymer, 6, 1544 (2014)

[7] Kim J, Chung JS, Kang H, Yu YA, Choi WJ, Kim HJ, Lee JC, Macromol. Res., 22(9), 963 (2014)

[8] Kudaibergenov SE, Polyampholytes: Synthesis, Characterization and Application, Springer Science & Business Media, New York, 2002.

[9] Zurick K, Bernards M, J. Appl. Polym. Sci., doi: 10.1002/app.40069., 131 (2014)

[10] Dobrynin AV, Colby RH, Rubinstein M, J. Polym. Sci. B: Polym. Phys., 42(19), 3513 (2004)

[11] Salamone JC, Rice WC, in Encyclopedia of Polymer Science and Engineering, Wiley, New York, 1988. Vol. 17, 2nd ed., pp 513-530 and pp 578-586.

[12] Salamone JC, Rice WC, Watterson AC, J. Macromol. Sci. A, 28, 885 (1991)

[13] Butler GB, Cyclopolymerization and Cyclocopolymerization, Marcel Dekker, New York, 1992.

[14] Mazumder MAJ, Umar Y, Ali SA, Polymer, 45(1), 125 (2004)

[15] Haladu SA, Ali SA, J. Polym. Sci. A: Polym. Chem., 51(23), 5130 (2013)

[16] Ali SA, Al-Muallem HA, Al-Hamouz OCSO, Estaitie MK, React. Funct. Polym., 86, 80 (2015)

[17] Butt FH, Rahman F, Baduruthamal U, Desalination, 109(3), 323 (1997)

[18] Pike RM, Cohen RA, J. Polym. Sci., 44, 531 (1960)

[19] Wielema TA, Engberts JBFN, Eur. Polym. J., 23, 947 (1987)

[20] Skouri M, Munch JP, Candau SJ, Neyret S, Candau F, Macromolecules, 27(1), 69 (1994)

[21] Salamone JC, Volksen W, Olson AP, Israel SC, Polymer, 19, 1157 (1978)

[22] Soto VMM, Galin JC, Polymer, 25, 254 (1984)

[23] Higgs PG, Joanny JF, J. Chem. Phys., 94, 1543 (1991)

[24] Rullens F, Devillers M, Laschewsky A, Macromol. Chem. Phys., 205, 1155 (2004)

[25] Pearson JF, Slifkin MA, Spectroc. Acta Pt. A-Molec. Biomolec. Spectr., 28, 2403 (1972)

[26] Butler GB, Angelo RJ, J. Am. Chem. Soc., 79, 3128 (1957)

[27] DeVynck V, Goethals EJ, Macromol. Rapid Commun., 18(2), 149 (1997)

[28] Everaers R, Johner A, Joanny JF, Europhys. Lett., 37, 275 (1997)

[29] Candau F, Joanny JF, in Polyampholytes (Properties in Aqueous Solution), Salamone JC, Ed., CRC Press, Boca Raton, FL, 1996, Vol. 7, pp 5462-5476.

[30] Wittmer J, Johner A, Joanny JF, Europhys. Lett., 24, 263 (1993)

[31] Wielema TA, Engberts JBFN, Eur. Polym. J., 26, 415 (1990)

[32] Al-Muallem HA, Wazeer MIM, Ali SA, Polymer, 43(15), 4285 (2002)

[33] Reitz RL, in Proceedings of the Water Supply Improvement Association, Development of a Broad-Spectrum Antiscalant for Reverse Osmosis Systems, 1984, pp 1-26.

[34] Liu D, Dong WB, Li FT, Hui F, Ledion J, Desalination, 304, 1 (2012)

[35] Hasson D, Shemer H, Sher A, Ind. Eng. Chem. Res., 50(12), 7601 (2011)

[36] Davey RJ, in The Role of Additives in Precipitation Processes, Industrial Crystallization, 81, Jancic SJ, de Jong EJ, Eds., North-Holland Publishing Co., 1982, pp 123-135.