Synthesis and characterization of hydrophobically modified polymeric betaines

Keywords: polymeric betaines, vesicles, micelles, pour point depressants

Abstract

Polymeric betaines containing long alkyl chains C12H25, C14H29, C16H33 and C18H37 were synthesized by Michael addition reaction of alkylaminocrotonates and methacrylic acid (MAA). They were characterized by FTIR, 13C NMR, DSC, DLS, GPC, cryo-TEM, viscometry and zeta-potential measurements. The polymers were fully soluble in DMF, THF and DMSO, partially dissolved in aromatic hydrocarbons (benzene, toluene, o-xylene) and formed colloid solutions in aqueous KOH. In aqueous KOH and DMSO solutions, hydrophobically modified polymeric betaines behaved as polyelectrolytes. The average hydrodynamic size and zeta potential of diluted aqueous solutions of hydrophobic polybetainess containing dodecyl-, tetradecyl-, hexadecyl-, and octadecyl groups were studied as a function of pH. Anomalous low values of the isoelectric point (IEP) of amphoteric macromolecules were found to be in the range of pH 2.7-3.4. According to DLS data, the average size of macromolecules tends to decrease with dilution. Zeta-potential of amphoteric macromolecules in aqueous solution is much higher than that in DMSO. The cryo-TEM results revealed that in both aqueous KOH and DMSO media, the micron- and nanosized vesicles existed. The structural organization of vesicles in water and DMSO is discussed. The wax inhibition effect of hydrophobic polybetaines at a decrease of the pour point temperatures of high paraffinic oils was better in comparison with commercial available ethylene-vinylacetate copolymers (EVA). 

Author Biographies

Zhanar Nurakhmetova, Laboratory of Engineering Profile K.I. Satpayev Kazakh National Reserach Technical University, Almaty

Institute of Polymer Materials and Technology, Almaty

Gulnur Tatykhanova, Laboratory of Engineering Profile K.I. Satpayev Kazakh National Research Technical University, Almaty
Institute of Polymer Materials and Technology, Almaty
Sarkyt Kudaibergenov, Laboratory of Engineering Profile K.I. Satpayev Kazakh National Research Technical University, Almaty
Institute of Polymer Materials and Technology, Almaty

References

1 Kudaibergenov S (2002) Polyampholytes: Synthesis, Characterization and Application. Kluwer Academic/Plenum Publishers, New York, USA. P.1-214. ISBN 030646781X

 

2 Johnson K, Fevola MJ, McCormick CL (2004) J Appl Polym Sci 92:647-657. http://dx.doi.org/10.1002/app.13646

 

3 Kudaibergenov SE, Jaeger W, Laschewsky A (2006) Adv Polym Sci 201:157-224. http://dx.doi.org/10.1007/12_078

 

4 Dimitrov I, Trzebicka B, Müller AH, Dworak A, Tsvetanov CB (2007) Progress Polym Sci 32:1275-1343. http://dx.doi.org/10.1016/j.progpolymsci.2007.07.001

 

5 Smith AE, Xu X, Kirkland SE, Savin DA, McCormick CL (2010) Macromolecules 43:1210-1217. http://dx.doi.org/10.1021/ma902378k

 

6 Strauss UP, Chiso YC (1986) Macromolecules 19:355-358. http://dx.doi.org/10.1021/ma00156a020

 

7 Tanchuk YV, Yablonko BM, Boiko VV (1982) Ukrainian Chemistry Journal 48:871-876. (In Russian)

 

8 Tanchuk YV, Yablonko BM (1984) Ukrainian Chemistry Journal 50:88-92. (In Russian)

 

9 Tanchuk YV, Yablonko BM (1988) Ukrainian Chemistry Journal 54:1099-1102. (In Russian)

 

10 Laschewsky A, Zerbe I (1991) Polymer 32:2081-2086. http://dx.doi.org/10.1016/0032-3861(91)90176-J

 

11 Anton P, Laschewsky A (1991) Macromol Rapid Comm 12:189-196. http://dx.doi.org/10.1002/marc.1991.030120307

 

12 Koberle P, Laschewsky A, Lomax TD (1991) Macromol Rapid Comm 12:427-430. http://dx.doi.org/10.1002/marc.1991.030120709

 

13 Laschewsky A (1991) Colloid Polym Sci 269:785-794.  http://dx.doi.org/10.1007/bf00657445

 

14   Anton P, Koberle P, Laschewsky A (1993) Macromol Chem Physic 194:1-27. http://dx.doi.org/10.1002/macp.1993.021940101

 

15   Anton P, Laschewsky A (1993) Macromol Chem Physic 194:601-624. http://dx.doi.org/10.1002/macp.1993.021940221

 

16    Favresse P, Laschewsky A (1999) Macromol Chem Physic 200:887-895. http://dx.doi.org/10.1002/(sici)1521-3935(19990401)200:4<887::aid-macp887>3.0.co;2-#

 

17    Favresse P, Laschewsky A, Emmerman C, Gros L, Linsner A (2001) Eur Polym J 37:877-885. http://dx.doi.org/10.1016/s0014-3057(00)00215-9

 

18    Cardoso J, Manero O (1991) J Polym Sci Pol Phys 29:639-647. http://dx.doi.org/10.1002/polb.1991.090290601

 

19   Kujawa P, Rosiak JM, Selb J, Candau F (2000) Mol Cryst Liq Cryst 354:401-407. http://dx.doi.org/10.1080/10587250008023632

 

20    Kujawa P, Rosiak JM, Selb J, Candau F (2001) Macromol Chem Physic 202:1384-1397 http://dx.doi.org/10.1002/1521-3935(20010501)202:8<1384::AID-MACP1384>3.0.CO;2-1

 

21   Didukh AG, Koizhaiganova RB, Bimendina LA, Kudaibergenov SE (2004) Appl Polym Sci 92:1042-1048. http://dx.doi.org/10.1002/app.20075

 

22    Kudaibergenov SE, Didukh AG, Ibraeva ZhE, Bimendina LA, Rullens F, Devillers M, Laschewsky А (2005) J Appl Polym Sci 98:2101-2108. http://dx.doi.org/10.1002/app.22007

 

23   Koromilas ND, Lainioti GC, Oikonomou EK, Bokias G, Kallitsis JK (2014) Eur Polym J 54:39-51. http://dx.doi.org/dx.doi.org/10.1016/j.eurpolymj.2014.02.009

 

24    Ahmed S, Hayashi F, Nagashima T, Matsumura K (2014) Biomaterials 35:6508-6518. http://dx.doi.org/10.1016/j.biomaterials.2014.04.030

 

25    An H, Liu C, Wang P, Li W, Tan Y, Xu K, Liu Ch (2011) Polym Bull 67:141-158. http://dx.doi.org/10.1007/s00289-011-0465-4

 

26    Sitnikova T, Rakhnyanskaya A, Yaroslavova E, Melik-Nubarov N, Yaroslavov A (2013) Polym Sci Ser A+ 55:163-170. http://dx.doi.org/10.1134/s0965545x13030061

 

27   Che Y-J, Tan Y, Cao J, Xin H, Xu GY (2011) Polym Bull 66:17-35. http://dx.doi.org/10.1007/s00289-010-0255-4

 

28   Liu C,  Hong B, Xu K, Zhang M, An H, Tan Y, Wang P (2014) Polym Bull 71:3051-3065. http://dx.doi.org/10.1007/s00289-014-1237-8

 

29   Kudaibergenov SE, Bimendina LA, Yashkarova MG (2007) J Macromol Sci A 44:899-913. http://dx.doi.org/10.1080/10601320701407995

Published
2015-09-30
How to Cite
Shakhvorostov, A., Nurakhmetova, Z., Tatykhanova, G., Nuraje, N., & Kudaibergenov, S. (2015). Synthesis and characterization of hydrophobically modified polymeric betaines. Chemical Bulletin of Kazakh National University, (3), 10-20. https://doi.org/https://doi.org/10.15328/cb645
Section
Organic and Polymers Chemistry