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Synthesis and application of a cyclopolymer bearing a propylphosphonic acid and a propylcarboxylic acid pendants in the same repeating unit

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Abstract

Diallyl[3-(diethoxyphosphoryl)propyl](3-ethoxycarbonylpropyl)ammonium chloride [ (CH2CH=CH2)2N+{(CH2)3PO3Et2} {(CH2)3CO2Et} Cl−], a new diallyl quaternary ammonium salt, has been cyclopolymerized to its cationic polyelectrolyte having pyrrolidine rings embedded in the polymer backbone. The polymer represents the first example of a cyclopolymer in which each repeating unit contains a propylphosphonate as well as a propylcarboxylate pendant. The hydrolysis of one, two or all the three-ester groups in the polymer afforded a series of pH-responsive macromolecules having identical degree of polymerization, which permitted a meaningful comparison of their solution behaviors. Apparent pK as of the triprotic repeating unit have been determined to be 2.52, 5.32 for 9.02 for the functionalities –PO3H2, −CO2H, and –PO3H−, respectively. The completely hydrolyzed polymer containing PO3H2 and CO2H groups demonstrated remarkable antiscalant behavior; at a concentration of 10 ppm, it inhibited the scaling of CaSO4 from its supersaturated solution with an inhibition efficiency of 100 % for over 500 min. The polymer may thus be exploited as an antiscalant in reverse osmosis plants.

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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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Authors and Affiliations

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

    Shaikh A. Ali

  2. Department of Basic Sciences, College of Engineering, University of Dammam, Dammam, Saudi Arabia

    Shamsuddeen A. Haladu

  3. Chemistry Department, University of Dammam, Dammam, 31113, Saudi Arabia

    Asma M. Z. El-Sharif

Authors
  1. Shaikh A. Ali
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  2. Shamsuddeen A. Haladu
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  3. Asma M. Z. El-Sharif
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Correspondence to Shaikh A. Ali.

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Ali, S.A., Haladu, S.A. & El-Sharif, A.M.Z. Synthesis and application of a cyclopolymer bearing a propylphosphonic acid and a propylcarboxylic acid pendants in the same repeating unit. J Polym Res 23, 167 (2016). https://doi.org/10.1007/s10965-016-1006-5

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  • DOI: https://doi.org/10.1007/s10965-016-1006-5

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