Advertisement

Colloid and Polymer Science

, Volume 296, Issue 6, pp 1005–1016 | Cite as

Tailoring the morphology and epoxy group content of glycidyl methacrylate-based polyHIPE monoliths via radiation-induced polymerization at room temperature

  • Song Yang
  • Yipeng Wang
  • Yunzhen Jia
  • Xuehui Sun
  • Peijian Sun
  • Yaqiong Qin
  • Ruyang Li
  • Huarong Liu
  • Cong Nie
Original Contribution

Abstract

Glycidylmethacrylate (GMA)-based poly(high internal phase emulsion) (polyHIPE) monoliths were prepared using a HIPE template via radiation-induced polymerization at room temperature. The effects of surfactant content, cross-linking degree, water fraction, and porogen content on the surface area, average void diameter, distribution of void diameter, average interconnection diameter, average pore diameter, and epoxy group content of GMA-based polyHIPE monoliths were investigated. The morphology and epoxy group content of GMA-based polyHIPE monoliths may be tailored by tuning each of the factors above according to the requirements of specific applications. Finally, the different morphology and epoxy group content of GMA-based polyHIPE monoliths were applied in phenol removal from cigarette smoke (CS) through a reaction between the epoxy group and phenol. The results showed that GMA-based polyHIPE monoliths with the higher content of epoxy group and bigger surface area showed the higher rate of phenol removal.

Keywords

High internal phase emulsion Glycidyl methacrylate PolyHIPE Monolith Morphology Epoxy group content Porous polymers 

Notes

Acknowledgements

The authors thank the National Natural Science Foundation of China (no. 51003122), the Dean Science and Technology Development Fund Project of Zhengzhou Tobacco Research Institute (no. 332016CA0210), the Key Science and Technology Projects of CNTC (no. 312010AA0040), and the National Science and Technology Project of China (no. 322012AK0030) for their financial support.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

References

  1. 1.
    Cameron NR, Sherrington DC (1996) High internal phase emulsions (HIPEs)—Structure, properties and use in polymer preparation. Adv Polym Sci 126:163–214CrossRefGoogle Scholar
  2. 2.
    Hainey P, Huxham IM, Rowatt B, Sherrington DC, Tetley L (1991) Synthesis and ultrastructural studies of styrene-divinylbenzene polyhipe polymers. Macromolecules 24:117–121CrossRefGoogle Scholar
  3. 3.
    Barbetta A, Cameron NR, Cooper SJ (2000) Chem Commun 221–222Google Scholar
  4. 4.
    Zhang H, Cooper AI (2005) Synthesis and applications of emulsion-templated porous materials. Soft Matter 1:107–113CrossRefGoogle Scholar
  5. 5.
    Menner A, Powell R, Bismarck A (2006) Open porous polymer foams via inverse emulsion polymerization: should the definition of high internal phase (ratio) emulsions be extended? Macromolecules 39:2034–2035CrossRefGoogle Scholar
  6. 6.
    Cameron NR (2005) High internal phase emulsion templating as a route to well-defined porous polymers. Polymer 46:1439–1449CrossRefGoogle Scholar
  7. 7.
    Busby W, Cameron NR, Jahoda CA (2001) Emulsion-derived foams (PolyHIPEs) containing poly(ε-caprolactone) as matrixes for tissue engineering. Biomacromolecules 2:154–164CrossRefGoogle Scholar
  8. 8.
    Christenson EM, Soofi W, Holm J, Cameron NR, Mikos AG (2007) Biodegradable fumarate-based polyHIPEs as tissue engineering scaffolds. Biomacromolecules 8:3806–3814CrossRefGoogle Scholar
  9. 9.
    Akay G, Birchand MA, Bokhari MA (2004) Microcellular polyHIPE polymer supports osteoblast growth and bone formation in vitro. Biomaterials 25:3991–4000CrossRefGoogle Scholar
  10. 10.
    Bokhari M, Carnachan RJ, Przyborski SA, Cameron NR (2007) Emulsion-templated porous polymers as scaffolds for three dimensional cell culture: effect of synthesis parameters on scaffold formation and homogeneity. J Mater Chem 17:4088–4094CrossRefGoogle Scholar
  11. 11.
    Zhao C, Danish E, Cameron NR, Kataky R (2007) Emulsion-templated porous materials (PolyHIPEs) for selective ion and molecular recognition and transport: applications in electrochemical sensing. J Mater Chem 17:2446–2453CrossRefGoogle Scholar
  12. 12.
    Small PW, Sherrington DC (1989). J Chem Soc-Chem Commun 21:1589–1591CrossRefGoogle Scholar
  13. 13.
    Ottens M, Leene G, Beenackers ACCM, Cameron NR, Sherrington DC (2000) PolyHipe: a new polymeric support for heterogeneous catalytic reactions: kinetics of hydration of cyclohexene in two- and three-phase systems over a strongly acidic sulfonated polyHipe. Ind Eng Chem Res 39:259–266CrossRefGoogle Scholar
  14. 14.
    Zhang S, Chen J, Perchyonok VT (2008) PolyHIPEs as novel media for conventional free radical chemistry. Lett Org Chem 5:304–309CrossRefGoogle Scholar
  15. 15.
    Su F, Bray CL, Tan B, Cooper AI (2008) Rapid and reversible hydrogen storage in clathrate hydrates using emulsion-templated polymers. Adv Mater 20:2663–2666CrossRefGoogle Scholar
  16. 16.
    Barbetta A, Cameron NR (2004) Morphology and surface area of emulsion-derived (PolyHIPE) solid foams prepared with oil-phase soluble porogenic solvents: span 80 as surfactant. Macromolecules 37:3188–3201CrossRefGoogle Scholar
  17. 17.
    Barbetta A, Cameron NR (2004) Morphology and surface area of emulsion-derived (PolyHIPE) solid foams prepared with oil-phase soluble porogenic solvents: three-component surfactant system. Macromolecules 37:3202–3213CrossRefGoogle Scholar
  18. 18.
    Carnachan RJ, Bokhari M, Przyborski SA, Cameron NR (2006) Tailoring the morphology of emulsion-templated porous polymers. Soft Matter 2:608–616CrossRefGoogle Scholar
  19. 19.
    Mao DL, Li TT, Liu HR, Li ZC (2013) Colloid polymer. Science 291:1649–1656Google Scholar
  20. 20.
    Cameron NR, Sherrington DC (1997) Preparation and glass transition temperatures of elastomeric polyHIPE materials. J Mater Chem 7:2209–2212CrossRefGoogle Scholar
  21. 21.
    Edwards JC, Gregory DP, Sharples M, Eur Pat 239360, 1987Google Scholar
  22. 22.
    Edwards JC, Gregory DP (1988) Sharples M. US Pat 4788225Google Scholar
  23. 23.
    Bayramoğlu G, Kaya B, Arica MY (2005) Immobilization of lipase onto spacer-arm attached poly(GMA-HEMA-EGDMA) microspheres. Food Chem 92:261–268CrossRefGoogle Scholar
  24. 24.
    Bayramoğlu G, Akgöl S, Bulut A, Denizli A, Arica MY (2003) Covalent immobilisation of invertase onto a reactive film composed of 2-hydroxyethyl methacrylate and glycidyl methacrylate: properties and application in a continuous flow system. Biochem Eng J 14:117–126CrossRefGoogle Scholar
  25. 25.
    Benčina M, Benčina K, Štrancar A, Podgornik A (2005) Immobilization of deoxyribonuclease via epoxy groups of methacrylate monoliths. J Chromat A 1065:83–91CrossRefGoogle Scholar
  26. 26.
    Zhang X, Guan RF, Chan DY (2005) Enzyme immobilization on amino-functionalized mesostructured cellular foam surfaces, characterization and catalytic properties. J Mol Catal B: Enzymatic 33:43–50CrossRefGoogle Scholar
  27. 27.
    Petro M, Svec F, Frèchet JM (1996) Immobilization of trypsin onto “molded” macroporous poly(glycidyl methacrylate-co-ethylene dimethacrylate) rods and use of the conjugates as bioreactors and for affinity chromatography. Biotechnol Bioeng 49:355–363CrossRefGoogle Scholar
  28. 28.
    Godjrvargova T, Kousolov V, Dimov A (1999) Preparation of an ultrafiltration membrane from the copolymer of acrylonitrile–glycidylmethacrylate utilized for immobilization of glucose oxidase. J Membrane Sci 152:235–242CrossRefGoogle Scholar
  29. 29.
    Svec F, Frèchet JM (1995). J Chromat A 705:89–103CrossRefGoogle Scholar
  30. 30.
    Svec F, Frèchet JM (1995) “Molded” rods of macroporous polymer for preparative separations of biological products. Biotechnol Bioeng 48:476–480CrossRefGoogle Scholar
  31. 31.
    Luo Q, Zou H, Xiao X, Guo Z, Kong L, Mao X (2001) Chromatographic separation of proteins on metal immobilized iminodiacetic acid-bound molded monolithic rods of macroporous poly(glycidyl methacrylate–co-ethylene dimethacrylate). J Chromatogr 926:255–264CrossRefGoogle Scholar
  32. 32.
    Majer J, Krajnc P (2010) Amine Functionalisations of Glycidyl methacrylate Based PolyHIPE Monoliths. Macromol Symp 296:5–10CrossRefGoogle Scholar
  33. 33.
    Sprob J, Sinz A (2012). Anal Bioanal Chem 402:2395–2405CrossRefGoogle Scholar
  34. 34.
    Jia M, Qin L, He XW, Li WY (2012) Preparation and application of lysozyme imprinted monolithic column with dopamine as the functional monomer. J Mater Chem 22:707–713CrossRefGoogle Scholar
  35. 35.
    Su RH, Ruan GH, Nie HG, Xie T, Zheng YJ, Du FY, Li JP (2015) Development of high internal phase emulsion polymeric monoliths for highly efficient enrichment of trace polycyclic aromatic hydrocarbons from large-volume water samples. J Chromat A 1405:23–31CrossRefGoogle Scholar
  36. 36.
    Van Berkel PM, Punt M, Koolhaas GJAA, Driessen WL, Reedijk J, Sherrington DC (1997) React Funct Polym 32:139–151, Highly copper(II)-selective chelating ion-exchange resins based ion bis(imidazole)-modified glycidyl methacrylate copolymersGoogle Scholar
  37. 37.
    Hainey P, Sherrington DC (2000) Oligoamine-functionalised poly(glycidyl methacrylate-ethyleneglycol dimethacrylate) resins as moderate base extractants for gold from cyanide solutions. React Funct Polym 43:195–210CrossRefGoogle Scholar
  38. 38.
    Bicak N, Sherrington DC, Sungur TS, Nükhet T (2003) A glycidyl methacrylate-based resin with pendant urea groups as a high capacity mercury specific sorbent. React Funct Polym 54:141–147CrossRefGoogle Scholar
  39. 39.
    Beneš MJ, Horák D, Švec F (2005) Methacrylate-based chromatographic media. J Sep Sci 28:1855–1875CrossRefGoogle Scholar
  40. 40.
    Krajnc P, Leber N, Štefanec D, Kontrec S, Podgornik A (2005) Preparation and characterisation of poly(high internal phase emulsion) methacrylate monoliths and their application as separation media. J Chromat A 1065:69–73CrossRefGoogle Scholar
  41. 41.
    Yao CH, Qi L, Jia HY, Xin PY, Yang GL, Chen Y (2009) A novel glycidyl methacrylate-based monolith with sub-micron skeletons and well-defined macropores. J Mater Chem 19:767–772CrossRefGoogle Scholar
  42. 42.
    Barbetta A, Dentini M, Leandri L, Ferraris G, Coletta A (2009) Synthesis and characterization of porous glycidylmethacrylate–divinylbenzene monoliths using the high internal phase emulsion approach. React Funct Polym 69:724–736CrossRefGoogle Scholar
  43. 43.
    Yang S, Zeng L, Wang YP, Sun XH, Sun PJ, Liu HM, Nie C, Liu HR (2014) Facile approach to glycidyl methacrylate-based polyHIPE monoliths with high epoxy-group content. Colloid Polym Sci 292:2563–2570CrossRefGoogle Scholar
  44. 44.
    Wang XB, Zhang ZC, Chen J, Wang SJ (2007) Preparation of charged polystyrene microlatexes by emulsion polymerization induced by gamma rays. Mater Lett 61:2662–2666CrossRefGoogle Scholar
  45. 45.
    Wu DZ, Ge XW, Zhang ZC, Wang MZ, Zhang SL (2004) Novel one-step route for synthesizing CdS/polystyrene nanocomposite hollow spheres. Langmuir 20:5192–5195CrossRefGoogle Scholar
  46. 46.
    Yang S, Liu HR (2006) A novel approach to hollow superparamagnetic magnetite/polystyrene nanocomposite microspheres via interfacial polymerization. J Mater Chem 16:4480–4487CrossRefGoogle Scholar
  47. 47.
    Yang S, Liu HR, Zhang ZC (2008) A facile route to hollow superparamagnetic magnetite/polystyrene nanocomposite microspheres via inverse miniemulsion polymerization. J Polym Sci Pol Chem 46:3900–3910CrossRefGoogle Scholar
  48. 48.
    Yang S, Liu HR, Huang HF, Zhang ZC (2009) Fabrication of superparamagnetic magnetite/poly(styrene-co-12-acryloxy-9-octadecenoic acid) nanocomposite microspheres with controllable structure. J Colloid Interf Sci 338:584–590CrossRefGoogle Scholar
  49. 49.
    Li TT, Liu HR, Zeng L, Yang S, Li ZC, Zhang JD, Zhou XT (2011) Macroporous magnetic poly(styrene–divinylbenzene) nanocomposites prepared via magnetite nanoparticles-stabilized high internal phase emulsions. J Mater Chem 21:12865–12872CrossRefGoogle Scholar
  50. 50.
    Mao DL, Li TT, Liu HR, Liu ZC, Shao H, Li Min (2013) Colloid Poly Sci 291:1649–1656Google Scholar
  51. 51.
    Wang SF, Zhang ZC, Liu HR, Zhang W, Qian Z, Wang BB (2010) One-step synthesis of manganese dioxide/polystyrene nanocomposite foams via high internal phase emulsion and study of their catalytic activity. Colloid Poly Sci 288:1031–1039CrossRefGoogle Scholar
  52. 52.
    Atawodi SE, Preussmann R, Spiegelhalder B (1995) Tobacco-specific nitrosamines in some Nigerian cigarettes. Cancer Lett 97:1–6CrossRefGoogle Scholar
  53. 53.
    Health Canada Test Method T-1140-Determination of Phenolic Compounds in Mainstream Tobacco Smoke, 1999Google Scholar
  54. 54.
    Williams JM, Wrobleski DA (1988) Spatial distribution of the phases in water-in-oil emulsions. Open and closed microcellular foams from cross-linked polystyrene. Langmuir 4:656–662CrossRefGoogle Scholar
  55. 55.
    Williams JM, Gray AJ, Wilkerson MH (1990) Emulsion stability and rigid foams from styrene or divinylbenzene water-in-oil emulsions. Langmuir 6:437–444CrossRefGoogle Scholar
  56. 56.
    Cameron NR (2005). Polymer 1:107–113Google Scholar
  57. 57.
    Barbetta A, Cameron NR (2004) Morphology and surface area of emulsion-derived (polyHIPE) solid foams prepared with oil-phase soluble porogenic solvents: span 80 as surfactant. Macromolecules 37:3188–3201CrossRefGoogle Scholar
  58. 58.
    Barbetta A, Cameron NR (2004) Morphology and surface area of emulsion-derived (polyHIPE) solid foams prepared with oil-phase soluble porogenic solvents: three-component surfactant system. Macromolecules 37:3202–3213CrossRefGoogle Scholar
  59. 59.
    Cameron NR, Barbetta A (2000) The influence of porogen type on the porosity, surface area and morphology of poly(divinylbenzene) polyHIPE foams. J Mater Chem 10:2466–2471CrossRefGoogle Scholar
  60. 60.
    Xie JP (2008) CORESTA congress. Shanghai, ChinaGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2018

Authors and Affiliations

  • Song Yang
    • 1
  • Yipeng Wang
    • 1
  • Yunzhen Jia
    • 1
  • Xuehui Sun
    • 1
  • Peijian Sun
    • 1
  • Yaqiong Qin
    • 1
  • Ruyang Li
    • 1
  • Huarong Liu
    • 2
  • Cong Nie
    • 1
  1. 1.Key Laboratory of Tobacco ChemistryZhengzhou Tobacco Research Institute of CNTCZhengzhouPeople’s Republic of China
  2. 2.Department of Polymer Science and EngineeringUniversity of Science and Technology of ChinaHefeiPeople’s Republic of China

Personalised recommendations