Acrylate copolymer-based super oil absorption resins: effects of steric hindrance of the monomer Original Paper First Online: 25 November 2019 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-SiO
2) showed further improvement in oil absorbency, reaching 39.5 mL/g, 43.6 mL/g, and 40.7 mL/g for benzene, xylene, and CCl 4, respectively. Compared to copolymers of SA and BA, copolymers formed using IBOMA or R-SiO 2 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 CCl 4 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 Electronic supplementary material
The online version of this article (
) contains supplementary material, which is available to authorized users. https://doi.org/10.1007/s11696-019-00997-2 Notes Acknowledgements
This work was supported by National Key R and D Program of China (No. 2017YFC0806600).
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
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 CrossRef Google Scholar
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 CrossRef Google Scholar
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 CrossRef Google Scholar
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 CrossRef Google Scholar
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 CrossRef Google Scholar
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 CrossRef Google Scholar
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 CrossRef Google Scholar
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 CrossRef Google Scholar
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 CrossRef Google Scholar
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 CrossRef Google Scholar
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 CrossRef Google Scholar
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 CrossRef Google Scholar
Li J (2005) Super water absorbent and super oil absorbent resin. China Machine Press, Beijing
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 CrossRef Google Scholar
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 CrossRef Google Scholar
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 4:61–68
CrossRef Google Scholar
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 CrossRef PubMed Google Scholar
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 CrossRef Google Scholar
Wang XP et al (2018) Synthesis and absorption organics of biomorphic hollow fibers Al
and acrylic ester-based crosslinked resin composite. Polym Compos 39:1988–1993.
https://doi.org/10.1002/pc.24158 CrossRef Google Scholar
Wu Y, Zhang H, Zeng K, Lin Y, Zheng Z, Ding X (2018) Oil-absorbing polymers from poly(lauryl methacrylate). Chem Res Appli 30:285–289
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 CrossRef PubMed Google Scholar
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 CrossRef Google Scholar
Yue X, Zhang T, Yang D, Qiu F, Rong J, Xu J, Fang J (2017) The synthesis of hierarchical porous Al
/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 CrossRef Google Scholar
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 CrossRef Google Scholar
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 CrossRef Google Scholar
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 CrossRef Google Scholar
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 MnO
. Polym Compos 39:4041–4049.
https://doi.org/10.1002/pc.24460 CrossRef Google Scholar
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 CrossRef PubMed Google Scholar
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 CrossRef Google Scholar
Zheng W, Liu P, Wang Y, Li Y, Yu H (2013) Preparation and oil-absorbting properties of Poly(Lauryl Methacrylate). Polym Mater Sci Eng 29:5–8
Zhu M, Hu P (2015) Instruments Analysis. Higher Education Press, Beijing
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