Advertisement

Acrylate copolymer-based super oil absorption resins: effects of steric hindrance of the monomer

  • Feng Zhou
  • Jie Zhang
  • Peng-fei Xie
  • Yu LiEmail author
Original Paper
  • 9 Downloads

Abstract

This work reports the relationship between monomer composition of typical acrylate copolymers and their oil absorption behaviors, considering the steric effects of isobornyl methacrylate (IBOMA) or reactive silica nanoparticles. With a molar ratio of stearyl acrylate (SA): butyl acrylate (BA): IBOMA = 1:1.2:0.3, the random copolymers exhibited absorbency of more than 30 mL/g for benzene, xylene, and other common fuel oils. The copolymers of SA and BA synthesized in the presence of 2% reactive silica nanoparticles (R-SiO2) showed further improvement in oil absorbency, reaching 39.5 mL/g, 43.6 mL/g, and 40.7 mL/g for benzene, xylene, and CCl4, respectively. Compared to copolymers of SA and BA, copolymers formed using IBOMA or R-SiO2 mainly hindered the diffusion of viscous oils such as kerosene or diesel, leading to decrease in absorption rate. All the prepared copolymers exhibited oil retention up to 99% for gasoline, kerosene, and CCl4 after saturation of absorption, after centrifugation at 3000 rpm for 5 min, which is attractive for practical applications.

Keywords

Oil absorption resin Acrylate copolymers Steric effects Isobornyl methacrylate Reactive silica nanoparticles 

Notes

Acknowledgements

This work was supported by National Key R and D Program of China (No. 2017YFC0806600).

Supplementary material

11696_2019_997_MOESM1_ESM.docx (79 kb)
Supplementary material 1 (DOCX 78 kb)

References

  1. Barbon SM, Rolland M, Anastasaki A, Truong NP, Schulze MW, Bates CM, Hawker CJ (2018) Macrocyclic side-chain monomers for photoinduced ATRP: synthesis and properties versus long-chain linear isomers. Macromolecules 51:6901–6910.  https://doi.org/10.1021/acs.macromol.8b01509 CrossRefGoogle Scholar
  2. Bu X, Lu Y, Chen S, Li D, Zhang Z, Qian P (2019) Fabrication of porous carbon nitride foams/acrylic resin composites for efficient oil and organic solvents capture. Chem Eng J 355:299–308.  https://doi.org/10.1016/j.cej.2018.08.088 CrossRefGoogle Scholar
  3. Chen XL, Deng LC, Wang XF, Guan S (2014) Synthesis and properties of high-oil absorption resin modified with organic bentonite. Chem J Chin Univ-Chin 35:2510–2515.  https://doi.org/10.7503/cjcu20140817 CrossRefGoogle Scholar
  4. Duan Y, Bian F, Huang H (2016a) Facile fabrication of porous oil-absorbent microspheres with high oil absorbency and fast oil absorption speed. Polym Adv Technol 27:228–234.  https://doi.org/10.1002/pat.3625 CrossRefGoogle Scholar
  5. Duan Y, Bian F, Huang H (2016b) A novel composite microsphere as a highly efficient absorbent for oils and organic solvents. Polym Adv Technol 27:1494–1500.  https://doi.org/10.1002/pat.3819 CrossRefGoogle Scholar
  6. Fang P, Mao P, Chen J, Du Y, Hou X (2014) Synthesis and properties of a ternary polyacrylate copolymer resin for the absorption of oil spills. J Appl Polym Sci.  https://doi.org/10.1002/app.40180 CrossRefGoogle Scholar
  7. Ge J, Wang F, Yin X, Yu J, Ding B (2018) Polybenzoxazine-functionalized melamine sponges with enhanced selective capillarity for efficient oil spill cleanup. ACS Appli Mater Interfaces 10:40274–40285.  https://doi.org/10.1021/acsami.8b14052 CrossRefGoogle Scholar
  8. Hai J, Bai B, Ding C, Wang H, Suo Y (2018) Removal of oil from water surface by novel composite NSM-g-P(MMA-co-BA) super oil-absorption resin. Polym Compos 39:1051–1063.  https://doi.org/10.1002/pc.24032 CrossRefGoogle Scholar
  9. Ho YS, McKay G (1999) A kinetic study of dye sorption by biosorbent waste product pith. Resour Conserv Recycl 25:171–193.  https://doi.org/10.1016/s0921-3449(98)00053-6 CrossRefGoogle Scholar
  10. Ji NY, Chen H, Yu MM, Qu RJ, Wang CH (2011) Synthesis of high oil-absorption resins of poly(methyl methacrylate-butyl methacrylate) by suspended emulsion polymerization. Polym Adv Technol 22:1898–1904.  https://doi.org/10.1002/pat.1689 CrossRefGoogle Scholar
  11. Ji NY, Chen H, Zong GX, Wang DJ (2012) Synthesis of novel high oil-absorption resins of poly(methyl methacrylate-butyl methacrylate) by surface-initiated atom transfer radical polymerization using activators regenerated by electron transfer for efficient removal of oil. Polym Int 61:1786–1791.  https://doi.org/10.1002/pi.4286 CrossRefGoogle Scholar
  12. Kunisada H, Yuki Y, Kondo S, Wada K (1991) Side-chain crystallization of comb-like copolymers obtained from isopropenyltriazines with comonomers having octadecyl group. Polym J 23:1365–1370.  https://doi.org/10.1295/polymj.23.1365 CrossRefGoogle Scholar
  13. Li J (2005) Super water absorbent and super oil absorbent resin. China Machine Press, BeijingGoogle Scholar
  14. Liang Y, Wang D, Chen H (2013) Preparation of high oil absorption resins by suspended emulsion polymerization and their properties. Sep Sci Technol 48:1977–1981.  https://doi.org/10.1080/01496395.2013.791696 CrossRefGoogle Scholar
  15. Mi H-Y, Jing X, Politowicz AL, Chen E, Huang H-X, Turng L-S (2018) Highly compressible ultra-light anisotropic cellulose/graphene aerogel fabricated by bidirectional freeze drying for selective oil absorption. Carbon 132:199–209.  https://doi.org/10.1016/j.carbon.2018.02.033 CrossRefGoogle Scholar
  16. Soliman FM et al (2016) Synthesis and characterization of an ionic liquid enhanced high oil absorption resin of P (BMIm-MMA-BA) and its oil absorption performance. Sci J Chem 4:61–68CrossRefGoogle Scholar
  17. Song C, Ding L, Yao F, Deng J, Yang W (2013) beta-Cyclodextrin-based oil-absorbent microspheres: preparation and high oil absorbency. Carbohydr Polym 91:217–223.  https://doi.org/10.1016/j.carbpol.2012.08.036 CrossRefPubMedGoogle Scholar
  18. Sun JM, Xu YY, Chen H, Tan Z, Fan LJ (2014) Synthesis and properties of high oil-absorbing resins with long chain by high internal phase emulsions as template. Sep Sci Technol 49:2518–2524.  https://doi.org/10.1080/01496395.2014.928322 CrossRefGoogle Scholar
  19. Wang XP et al (2018) Synthesis and absorption organics of biomorphic hollow fibers Al2O3 and acrylic ester-based crosslinked resin composite. Polym Compos 39:1988–1993.  https://doi.org/10.1002/pc.24158 CrossRefGoogle Scholar
  20. Wu Y, Zhang H, Zeng K, Lin Y, Zheng Z, Ding X (2018) Oil-absorbing polymers from poly(lauryl methacrylate). Chem Res Appli 30:285–289Google Scholar
  21. Xu T, Wang Z, Ding YC, Xu WH, Wu WD, Zhu ZT, Fong H (2018) Ultralight electrospun cellulose sponge with super-high capacity on absorption of organic compounds. Carbohydr Polym 179:164–172.  https://doi.org/10.1016/j.carbpol.2017.09.086 CrossRefPubMedGoogle Scholar
  22. Xue F, Jia DM, Li Y, Jing XL (2015) Facile preparation of a mechanically robust superhydrophobic acrylic polyurethane coating. J Mater Chem A 3:13856–13863.  https://doi.org/10.1039/c5ta02780b CrossRefGoogle Scholar
  23. Yue X, Zhang T, Yang D, Qiu F, Rong J, Xu J, Fang J (2017) The synthesis of hierarchical porous Al2O3/acrylic resin composites as durable, efficient and recyclable absorbents for oil/water separation. Chem Eng J 309:522–531.  https://doi.org/10.1016/j.cej.2016.10.049 CrossRefGoogle Scholar
  24. Zhang T, Hu F, Zhang C, Yang D, Qiu F, Peng X (2017) A novel multi-wall carbon nanotubes/poly(n-butylacrylate-co-butyl methacrylate) hybrid resin: synthesis and oil/organic solvents absorption. Fibers Polym 18:1865–1873.  https://doi.org/10.1007/s12221-017-7461-8 CrossRefGoogle Scholar
  25. Zhang N, Zhou Y, Zhang Y, Jiang W, Wang T, Fu J (2018a) Dual-templating synthesis of compressible and superhydrophobic spongy polystyrene for oil capture. Chem Eng J 354:245–253.  https://doi.org/10.1016/j.cej.2018.07.184 CrossRefGoogle Scholar
  26. Zhang T, Nie X, Zhang C, Yang D, Qiu F (2018b) Novel flower-like ZnO hybridized with acrylic ester resin for enhanced oil absorption properties. Polym-Plast Tech Eng 57:1665–1675.  https://doi.org/10.1080/03602559.2017.1419485 CrossRefGoogle Scholar
  27. Zhang T, Zhang C, Qiu FX, Yang DY, Shi SN, Shi TH, Nie XB (2018c) Enhancement of oil absorption properties of acrylic ester resin hybridized with well-organized sea urchin-like MnO2. Polym Compos 39:4041–4049.  https://doi.org/10.1002/pc.24460 CrossRefGoogle Scholar
  28. Zhang HY et al (2019a) Super light 3D hierarchical nanocellulose aerogel foam with superior oil adsorption. J Colloid Interface Sci 536:245–251.  https://doi.org/10.1016/j.jcis.2018.10.038 CrossRefPubMedGoogle Scholar
  29. Zhang XM, Fu F, Gao XM, Hou XF (2019b) Magnetically driven superhydrophobic polyurethane sponge for high efficiency oil/water mixtures separation. J Bio Eng 16:38–46.  https://doi.org/10.1007/s42235-019-0004-9 CrossRefGoogle Scholar
  30. Zheng W, Liu P, Wang Y, Li Y, Yu H (2013) Preparation and oil-absorbting properties of Poly(Lauryl Methacrylate). Polym Mater Sci Eng 29:5–8Google Scholar
  31. Zhu M, Hu P (2015) Instruments Analysis. Higher Education Press, BeijingGoogle Scholar

Copyright information

© Institute of Chemistry, Slovak Academy of Sciences 2019

Authors and Affiliations

  1. 1.Shanghai Fire Research Institute of MEMShanghaiPeople’s Republic of China
  2. 2.Department of Applied Chemistry, Xi’an Key Laboratory of Sustainable Energy Materials, School of ScienceXi’an Jiaotong UniversityXi’anPeople’s Republic of China
  3. 3.Petrochina West–East Gas Pipeline CompanyShanghaiPeople’s Republic of China

Personalised recommendations