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A novel twin-tailed hydrophobically associating copolymer: synthesis, characterization and solution properties

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Abstract

Novel twin-tailed hydrophobically associating copolymers (DDSPAM) were prepared by micellar copolymerization of acrylamide (AM) and sodium vinylsulfonate with N,N-didecyl-N-methyl-N-(4-vinylbenzyl)ammonium chloride in an aqueous solution. The structure and composition of DDSPAM were characterized by 1H-NMR and elemental analysis. While the molecular weights of the copolymers were obtained via static light scattering, the hydrodynamic radius of aggregates was investigated using dynamic light scattering. The critical micellar concentration cmc and γ cmc values of DDSPAM were measured using fluorescence and later correlated with the values obtained from surface tension measurements. In addition, the viscosity stability studies of DDSPAM and hydrolyzed polyacrylamide (HPAM) revealed that DDSPAM, with twin tails of hydrophobic groups, exhibited better salt tolerance as well as temperature resistance compared to HPAM.

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References

  1. Shalaby SW, McCormick CL, Butler GB (1991) Water-soluble polymers: synthesis, solution properties, and applications. J Am Chem Soc 467:523

    Google Scholar 

  2. Glass JE (1989) Polymers in aqueous media: performance through association. J Am Chem Soc 223:576

    Google Scholar 

  3. Li WB, An HY, Tan Y, Lu CG, Liu C, Li PC, Xu K, Wang PX (2012) Hydrophobically associated hydrogels based on acrylamide and anionic surface active monomer with high mechanical strength. Soft Matter 8:5078–5086

    Article  CAS  Google Scholar 

  4. Evani S, Rose GD (1987) Water soluble hydrophobe association polymers. Polym Mater Sci Eng 57:471–481

    Google Scholar 

  5. Argillier JF, Audibert A (1996) Solution and adsorption properties of hydrophobically associating water-soluble polyacrylamides. Colloid Surf A 113:247–257

    Article  CAS  Google Scholar 

  6. Rodriguez M, Xue J, Gouveia LM, Müller AJ, Sáez AE, Rigolini J, Grassl B (2011) Shear rheology of anionic and zwitterionic modified polyacrylamides. Colloid Surf A 373:66–73

    Article  CAS  Google Scholar 

  7. Blagodatskikh IV, Vasil’Eva OV, Ivanova EM, Bykov SV, Churochkina NA, Pryakhina TA, Smirnov VA, Philippova OE, Khokhlov AR (2004) New approach to the molecular characterization of hydrophobically modified polyacrylamide. Polymer 45:5897–5904

    Article  CAS  Google Scholar 

  8. Jiménez-Regalado EJ, Cadenas-Pliego G, Pérez-Álvarez M, Hernández-Valdez Y (2004) Study of three different families of water-soluble copolymers: synthesis, characterization and viscoelastic behavior of semidilute solutions of polymers prepared by solution polymerization. Polymer 45:1993–2000

    Article  Google Scholar 

  9. Masotti A, Vicennati P, Boschi F, Calderan L, Sbarbati A, Ortaggi G (2008) A novel near-infrared indocyanine dye-polyethylenimine conjugate allows DNA delivery imaging in vivo. Bioconjugate Chem 19:983–987

    Article  CAS  Google Scholar 

  10. Xue W, Hamley IW, Castelletto V, Olmsted PD (2004) Synthesis and characterization of hydrophobically modified polyacrylamides and some observations on rheological properties. Eur Polym J 40:47–56

    Article  CAS  Google Scholar 

  11. Johnson KM, Fevola MJ, McCormick CL (2004) Hydrophobically modified acrylamide-based polybetaines. I. Synthesis, characterization, and stimuli-responsive solution behavior. J Appl Polym Sci 92:647–657

    Article  CAS  Google Scholar 

  12. Hill A, Candau F, Selb J (1993) Properties of hydrophobically associating polyacrylamides: influence of the method of synthesis. Macromolecules 26:4521–4532

    Article  CAS  Google Scholar 

  13. Xue W, Hamley IW, Huglin MB (2002) Rapid swelling and deswelling of thermoreversible hydrophobically modified poly(N-isopropylacrylamide) hydrogels prepared by freezing polymerisation. Polymer 43:5181–5186

    Article  CAS  Google Scholar 

  14. Volpert E, Selb J, Candau F (1996) Influence of the hydrophobe structure on composition, microstructure, and rheology in associating polyacrylamides prepared by micellar copolymerization. Macromolecules 29:1452–1463

    Article  CAS  Google Scholar 

  15. Volpert E, Selb J, Candau F (1998) Associating behaviour of polyacrylamides hydrophobically modified with dihexylacrylamide. Polymer 39:1025–1033

    Article  CAS  Google Scholar 

  16. Castelletto V, Hamley IW (2009) Self assembly of a model amphiphilic phenylalanine peptide/polyethylene glycol block copolymer in aqueous solution. Biophys Chem 141:169–174

    Article  CAS  Google Scholar 

  17. Candau F, Selb J (1999) Hydrophobically-modified polyacrylamides prepared by micellar polymerization. Adv Colloid Interfac 79:149–172

    Article  CAS  Google Scholar 

  18. Hill A, Candau F, Selb J (1993) Properties of hydrophobically associating polyacrylamides: influence of the method of synthesis. Macromolecules 26:4521–4532

    Article  CAS  Google Scholar 

  19. Bakshi MS, Kaur R, Kaur I, Mahajan RK, Sehgal P, Doe H (2003) Unlike surfactant-polymer interactions of sodium dodecyl sulfate and sodium dodecylbenzene sulfonate with water-soluble polymers. Colloid Polym Sci 281:716–726

    Article  CAS  Google Scholar 

  20. Branham KD, Davis DL, Middleton JC, McCormick CL (1994) Water-soluble polymers: 59. Investigation of the effects of polymer microstructure on the associative behaviour of amphiphilic terpolymers of acrylamide, acrylic acid and N-[(4-decyl) phenyl] acrylamide. Polymer 35:4429–4436

    Article  CAS  Google Scholar 

  21. Feng YJ, Billon L, Grassl B, Bastiat G, Borisov O, François J (2005) Hydrophobically associating polyacrylamides and their partially hydrolyzed derivatives prepared by post-modification. 2. Properties of non-hydrolyzed polymers in pure water and brine. Polymer 46:9283–9295

    Article  CAS  Google Scholar 

  22. Wu JL, Wang YM, Hara M, Granville M, Jerome RJ (1994) Salt-free polyelectrolyte behavior of polystyrene-based telechelic ionomers in a polar solvent. 1. Viscosity and low-angle light scattering studies. Macromolecules 27:1195–1200

    Article  CAS  Google Scholar 

  23. Che YJ, Tan YB, Cao J, Xu G (2010) A study of aggregation behavior of a sulfobetaine copolymer in dilute solution. J Polym Res 17:557–566

    Article  CAS  Google Scholar 

  24. Huang XL, Tan YB, Zhou QF, Wang YX, Che YJ (2008) Aggregation behavior of sodium alginate with cucurbit [6] uril in aqueous solution. Carbohyd Polym 74:685–690

    Article  CAS  Google Scholar 

  25. Singh T, Kumar A (2007) Aggregation behavior of ionic liquids in aqueous solutions: effect of alkyl chain length, cations, and anions. J Phys Chem B 111:7843–7851

    Article  CAS  Google Scholar 

  26. Che YJ, Tan YB, Cao J, Xin HP, Xu GY (2011) Synthesis and properties of hydrophobically modified acrylamide-based polysulfobetaines. Polym Bull 61:17–35

    Article  Google Scholar 

  27. Che YJ, Tan YB, Ren XN, Xin HP, Meng FJ (2012) Solution properties of hydrophobically modified acrylamide-based polysulfobetaines in the presence of surfactants. Colloid Polym Sci 290:1237–1245

    CAS  Google Scholar 

  28. Mozumder MS, Alnaizy RS, Umar Y, Ali SA, Abu-Sharkh BF (2005) Influence of hydrophobe content and salt concentration on dilute solution behaviour of hydrophobically modified ionic polymers from diallylammonium salts/sulfur dioxide cyclocopolymerization: LIGHT scattering and fluorescence spectroscopy. Eur Polym J 41:2224–2231

    Article  CAS  Google Scholar 

  29. McCormick CL, Salazar LC (1992) Water-soluble copolymers. 43. Ampholytic copolymers of sodium 2-(acrylamido)-2-methylpropanesulfonate with [2-(acrylamido)-2-methylpropyl] trimethylammonium chloride. Macromolecules 25:1896–1900

    Article  CAS  Google Scholar 

  30. Kathmann EE, White LA, McCormick CL (1997) Water soluble polymers: 69. pH and electrolyte responsive copolymers of acrylamide and the zwitterionic monomer 4-(2-acrylamido-2-methylpropyldimethylammonio) butanoate: synthesis and solution behaviour. Polymer 38:871–878

    Article  CAS  Google Scholar 

  31. Gao B, Jiang L, Liu K (2007) Microstructure and association property of hydrophobically modified polyacrylamide of a new family. Eur Polym J 43:4530–4540

    Article  CAS  Google Scholar 

  32. Yahaya GO, Ahdab AA, Ali SA, Abu-Sharkh BF, Hamad EZ (2001) Solution behavior of hydrophobically associating water-soluble block copolymers of acrylamide and N-benzylacrylamide. Polymer 42:3363–3372

    Article  CAS  Google Scholar 

  33. Wu D, Xu G, Sun Y, Zhang H, Mao H, Feng Y (2007) Interaction between proteins and cationic gemini surfactant. Biomacromolecules 8:708–712

    Article  CAS  Google Scholar 

  34. Zhang L, Lv X, Zhu YJ, Zhang J, Wang H, Tan YB (2011) Synthesis and properties of new polymeric surfactant with quaternary ammonium salt. Colloid Polym Sci 289:1579–1587

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors gratefully acknowledge the financial support from Major Research of Science and Technology, China (Grant No. 2011ZX05024-004-08) and National Basic Research Program of China (973 Program, 2009CB930103).

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Correspondence to Bo Wu or Yebang Tan.

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Kuang, W., Zhang, J., Li, R. et al. A novel twin-tailed hydrophobically associating copolymer: synthesis, characterization and solution properties. Polym. Bull. 70, 3547–3562 (2013). https://doi.org/10.1007/s00289-013-1039-4

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  • DOI: https://doi.org/10.1007/s00289-013-1039-4

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