Abstract
In order to attain the controlled release of fragrance, the intercalation of cyclodextrins (CDs) and fragrance in layered double hydroxides (LDHs) was examined. Carboxymethyl-β-CDs (CMCDs) of various degrees of substitution as well as Mg–Al support were synthesized. CMCDs were intercalated into LDH by the reconstruction method. Powder X-ray diffraction, thermal gravimetric analyses and Fourier transform infrared indicated a successful intercalation of CMCDs into the LDH gallery. The retention capacities of the hybrid materials were investigated in aqueous phase and in gaseous solution by static headspace gas chromatography and multiple headspace extraction. The functionalization of the LDH with CMCD allowed the encapsulation of various organic guests and could prolong the fragrance release time in comparison to that from LDH without CMCD, which can be attributed to the inclusion of the fragrance compound in the CMCD cavity.
Similar content being viewed by others
Abbreviations
- β-CD:
-
β-Cyclodextrin
- CDs:
-
Cyclodextrins
- CMCD:
-
Carboxymethyl-β-cyclodextrin
- DS:
-
Degree of substitution
- FT-IR:
-
Fourier transform infrared
- LDH:
-
Layered double hydroxides
- MHE:
-
Multiple headspace extraction
- SHGC:
-
Static headspace gas chromatography
References
Evans, D.G., Slade, R.C.T.: Structural aspects of layered double hydroxides. Struct. Bond. 119, 1–87 (2006)
Genty, E., Cousin, R., Gennequin, C., Capelle, S., Aboukaïs, A., Siffert, S.: Investigation of Au/hydrotalcite catalysts for toluene total oxidation. Catal. Today 176(1), 116–119 (2011)
Sels, B.F., De Vos, D.E., Jacobs, P.A.: Bromide-assisted oxidation of substituted phenols with hydrogen peroxide to the corresponding p-quinol and p-quinol ethers over WO4 2− exchanged layered double hydroxides. Angew. Chem. Int. Ed. 44(2), 310–313 (2004)
Choy, J.-H., Choi, S.-J., Oh, J.-M., Park, T.: Clay minerals and layered double hydroxides for novel biological applications. Appl. Clay Sci. 36(1–3), 122–132 (2007)
Khan, A.I., Ragavan, A., Fong, B., Markland, C., O’Brien, M., Dunbar, T.G., Williams, G.R., O’Hare, D.: Recent developments in the use of layered double hydroxides as host materials for the storage and triggered release of functional anions. Ind. Eng. Chem. Res. 48(23), 10196–10205 (2009)
Markland, C., Williams, G.R., O’Hare, D.: The intercalation of flavouring compounds into layered double hydroxides. J. Mater. Chem. 21(44), 17896–17903 (2011)
Nakayama, H., Kuwano, K., Tsuhako, M.: Controlled release of drug from cyclodextrin-intercalated layered double hydroxide. J. Phys. Chem. Solids 69(5–6), 1552–1555 (2008)
Liu, X.L., Wei, M., Wang, Z.L., Evans, D.G., Duan, X.: Controllable nanocage structure derived from cyclodextrin-intercalated layered double hydroxides and its inclusion properties for dodecylbenzene. J. Phys. Chem. C 112(45), 17517–17524 (2008)
Mohanambe, L., Vasudevan, S.: Inclusion of poly-aromatic hydrocarbon (PAH) molecules in a functionalized layered double hydroxide. J. Chem. Sci. 118(1), 105–115 (2006)
Szjelti, J.: Introduction and general overview of cyclodextrin chemistry. Chem. Rev. 98, 1743–1753 (1998)
Connors, K.A.: The stability of cyclodextrin complexes in solution. Chem. Rev. 97, 1325–1357 (1997)
Singh, M., Sharma, R., Banerjee, U.C.: Biotechnological applications of cyclodextrins. Biotechnol. Adv. 20, 341–359 (2002)
Decock, G., Fourmentin, S., Surpateanu, G.G., Landy, D., Decock, P., Surpateanu, G.: Experimental and theoretical study on the inclusion compounds of aroma components with β-cyclodextrins. Supramol. Chem. 18(6), 477–482 (2006)
Decock, G., Landy, D., Surpateanu, G., Fourmentin, S.: Study of the retention of aroma components by cyclodextrins by static headspace gas chromatography. J. Incl. Phenom. Macrocycl. Chem. 62, 297–302 (2008)
Ciobanu, A., Mallard, I., Landy, D., Brabie, G., Nistor, D., Fourmentin, S.: Inclusion interactions of cyclodextrins and crosslinked cyclodextrin polymers with linalool and camphor in Lavandula angustifolia essential oil. Carbohydr. Polym. 87(3), 1963–1970 (2012)
Martel, B., Morcellet, M., Ruffin, D., Vinet, F., Weltrowski, M.: Capture and controlled release of fragrances by CD finished textiles. J. Incl. Phenom. Macrocycl. Chem. 44(1–4), 439–442 (2002)
Zhao, H., Vance, G.F.: Molecular inclusion properties of hydrophobic organic compounds by a modified β-cyclodextrin intercalated within a layered double hydroxide. J. Incl. Phenom. Macrocycl. Chem. 31(4), 305–317 (1998)
Mohanambe, L., Vasudevan, S.: Insertion of iodine in a functionalized inorganic layered solid. Inorg. Chem. 43(20), 6421–6425 (2004)
Park, S.Y., Park, J.K., Park, J.H., McNeff, C.V., Carr, P.W.: Separation of racemic 2,4-dinitrophenyl amino acids on carboxymethyl-β-cyclodextrin coated zirconia in RPLC. Microchem. J. 70, 179–185 (2001)
Ravoo, B.J., Darcy, R., Mazzaglia, A., Nolan, D., Gaffney, K.: Supramolecular tapes formed by a catanionic cyclodextrin in water. Chem. Commun. 9, 827–828 (2001)
Gennequin, C., Barakat, T., Tidahy, H.L., Cousin, R., Lamonier, J.-F., Aboukaïs, A., Siffert, S.: Use and observation of the hydrotalcite “memory effect” for VOC oxidation. Catal. Today 157(1–4), 191–197 (2010)
Gennequin, C., Cousin, R., Lamonier, J.-F., Siffert, S., Aboukaïs, A.: Toluene total oxidation over Co supported catalysts synthesised using “memory effect” of Mg–Al hydrotalcite. Catal. Commun. 9(7), 1639–1643 (2008)
Nakayama, H., Wada, N., Tsuhako, M.: Intercalation of amino acids and peptides into Mg–Al layered double hydroxide by reconstruction method. Int. J. Pharm. 269(2), 469–478 (2004)
Kolb, B.: Headspace sampling with capillary columns. J. Chromatogr. A 842(1–2), 2163–2205 (1999)
Snow, N.H., Slack, G.C.: Head-space analysis in modern gas chromatography. Trends Anal. Chem. 21(9–10), 608–617 (2002)
Kolb, B., Ettre, L.S.: Static Headspace-Gas Chromatography Theory and Practice, 2nd edn. Wiley, Hoboken (2006)
Dron, P.I., Fourmentin, S., Cazier, F., Landy, D., Surpateanu, G.: Cyclophanes or cyclodextrins: What is the best host for aromatic volatile organic compounds? Supramol. Chem. 20(5), 473–477 (2008)
Blach, P., Fourmentin, S., Landy, D., Cazier, F., Surpateanu, G.: Cyclodextrins: a new efficient absorbent to treat waste gas streams. Chemosphere 70(3), 374–380 (2008)
Fourmentin, S., Outirite, M., Blach, P., Landy, D., Ponchel, A., Monflier, E., Surpateanu, G.: Solubilisation of chlorinated solvents by cyclodextrin derivatives. A study by static headspace gas chromatography and molecular modelling. J. Hazard. Mater. 141(1), 92–97 (2007)
Landy, D., Fourmentin, S., Salome, M., Surpateanu, G.: Analytical improvement in measuring formation constants of inclusion complexes between β-cyclodextrin and phenolic compounds. J. Incl. Phenom. Macrocycl. Chem. 38(1–4), 187–198 (2000)
Mohanambe, L., Vasudevan, S.: Structure of a cyclodextrin functionalized anionic clay: XRD analysis, spectroscopy, and computer simulations. Langmuir 21(23), 10735–10742 (2005)
Zhao, H., Vance, G.F.: Intercalation of carboxymethyl-β-cyclodextrin into magnesium–aluminum layered double hydroxide. J. Chem. Soc. Dalton Trans. 11, 1961–1965 (1997)
Salmones, J., Zeifert, B., Garduño, M.H., Contreras-Larios, J., Acosta, D.R., Serrano, A.R., Garcia, L.A.: Synthesis and characterization of hydrotalcites by mechanical milling and conventional method. Catal. Today 133–135(1–4), 886–890 (2008)
Ladaa, T.I., Lee, C.M., Coates, J.T., Falta, R.W.: Cosolvent effects of alcohols on the Henry’s law constant and aqueous solubility of tetrachloroethylene. Chemosphere 44(5), 1137–1143 (2001)
Kashiyama, N., Boving, T.B.: Hindered gas-phase partitioning of trichloroethylene from aqueous cyclodextrin systems: implications for treatment and analysis. Environ. Sci. Technol. 38(16), 4439–4444 (2004)
Acknowledgments
UCEIV participates in the Institut de Recherche en ENvironnement Industriel (IRENI) which is financed by the Communauté Urbaine de Dunkerque, the Région Nord Pas-de-Calais, the Ministère de l’Enseignement Supérieur et de la Recherche, the CNRS and European Regional Development Fund (ERDF).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Ciobanu, A., Ruellan, S., Mallard, I. et al. Cyclodextrin-intercalated layered double hydroxides for fragrance release. J Incl Phenom Macrocycl Chem 75, 333–339 (2013). https://doi.org/10.1007/s10847-012-0227-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10847-012-0227-4