Abstract
Resins obtained from Pinus genus species have been widely used in very different fields throughout history. As soon as the resins are secreted, molecular changes start altering their chemical, mechanical and optical properties. The ageing processes are complex, and the chemical and structural changes associated with resin degradation are not yet fully known. Many questions still remain open, for instance changes happening in pimaranes, one of the two diterpenoid constituents of the resin. A systematic study of the ageing process of Pinus resins is done through Fourier transform infrared spectroscopy (FTIR) using chemical standards and complementing the obtained results with gas chromatography coupled to mass spectrometry (GC/MS) analysis when necessary. Moreover, long-term degradation processes are also investigated through the analysis of a selection of dated historical resins. This study overcomes the limitations of GC/MS and brings new information about the reactions and interactions between molecules during Pinus resin ageing processes. It also provides information about which bonds are affected and unaffected, and these can be used as specific markers of the degradation and of the resins themselves.
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References
Richardson DM. Ecology and biogeography of Pinus. Cambridge: Cambridge University Press; 2000.
Belgacem MN, Gandini A. Monomers, polymers and composites from renewable resources. Oxford: Elsevier; 2008.
Fiebach K, Grimm D. Resins, natural. In: Ullmann’s encyclopedia of industrial chemistry. 7th edn. Weinheim: Wiley; 2007.
Langenheim JH. Plant resins: chemistry, evolution, ecology, and ethnobotany. Cambridge: Timber; 2003.
Mills JS, White R. Organic chemistry of museum objects. New York: Butterworth-Heinemann; 1999.
Mills JS, White R. Natural resins of art and archaeology their sources, chemistry, and identification. Stud Conserv. 1977;22(1):12–31.
Colombini MP, Modugno F. Organic mass spectrometry in art and archaeology. Pisa: Wiley; 2009.
Pastorova II, van der Berg KJ, Boon JJ, Verhoeven JW. J Anal Appl Pyrol. 1997;43:41–57.
Osete-Cortina L, Doménech-Carbó MT, Mateo-Castro R, Gimeno-Adelantado JV, Bosch-Reig F. J Chromatogr A. 2004;1024:187–94.
Berg KJ, Boon JJ, Pastorova II, Spetter LF. J Mass Spectrom. 2000;35(4):512–33.
Steigenberger G, Herm C. Anal Bioanal Chem. 2011;401(6):1771–84.
Abdel-Ghani M, Edwards HGM, Stern B, Janaway R. Spectrochim Acta A. 2009;73:566–75.
Chiavari G, Fabbri D, Prati S. Chromatographia. 2002;55(9–10):611–6.
Osete-Cortina L, Doménech-Carbó MT. J Chromatogr A. 2005;1065(2):265–78.
Anderson KB, Winans RE. Anal Chem. 1991;63:2901–8.
Prati S, Smith S, Chiavari G. Chromatographia. 2004;59:227–31.
Osete-Cortina L, Doménech-Carbó MT. J Anal Appl Pyrolysis. 2006;76:144–53.
Derrick MR, Stulik D, Landry JM. Infrared spectroscopy in conservation science. Los Angeles: The Getty Conservation Institute; 1999.
Beltran V, Salvadó N, Butí S, Cinque G. Microchem J. 2015;118:115–23.
Font J, Salvadó N, Butí S, Enrich J. Anal Chim Acta. 2007;598(1):119–27.
Bertrand L, Robinet L, Cohen SX, Sandt C, Le Hô AS, Soulier B, et al. Anal Bioanal Chem. 2011;399(9):3025–32.
Robinson N, Evershed RP, Higgs WJ, Jerman K, Eglinton G. Analyst (Cambridge, U K). 1987;112:637–44.
Derrick M. J Am Inst Conserv. 1989;1:43–56.
Derrick M, Stulik DC, Landry JM, Bouffard SP. J Am Inst Conserv. 1992;2:225–36.
Daher C, Paris C, Le Hô A, Bellot-Gurlet L, Échard J. J Raman Spectrosc. 2010;41(11):1494–9.
Brody RH, Edwards HGM, Pollard M. Biopolymers. 2002;67(2):129–41.
Vandenabeele P, Wehling B, Moens L, Edwards H, De Reu M, Van Hooydonk G. Anal Chim Acta. 2000;407:261–74.
Prati S, Sciutto G, Mazzeo R, Torri C, Fabbri D. Anal Bioanal Chem. 2011;399:3081–91.
Doménech-Carbó MT. Anal Chim Acta. 2008;621(2):109–39.
Scalarone D, van der Horst J, Boon JJ, Chiantore O. J Mass Spectrom. 2003;38:607–17.
European Forest Genetic Resources Programme (EUFORGEN). http://www.euforgen.org/distribution-maps/ (2015). Accessed 14 Jan 2015.
Merrifield MP. Medieval and Renaissance treatises on the arts of painting: original texts with English translations. New York: Dover; 1999.
Eastlake CL. Methods and materials of painting of the great schools and masters. New York: Dover; 2001.
Smith CS, Hawthorne JG. Mappae Clavicula: a little key to the world of medieval techniques. Philadelphia: American Philosophical Society; 1974.
Thornton J. J Am Inst Conserv. 1998;37(1):3–22.
Dardes K, Rothe A. The structural conservation of panel paintings: proceedings of a Symposium at the J. Paul Getty Museum, 24–28 April 1995. Los Angeles: Getty Conservation Institute; 1998.
Jones R. Carbon with two heteroatoms with at least one carbon-to-heteroatom multiple link, vol 5. In: Katritzky AR, Taylor RJK, editors. Comprehensive organic functional groups transformations II. Cambridge: Elsevier; 2005.
Flett M St C. J Chem Soc. 1951;962–7.
Bratoz S, Hadzi D, Sheppard N. Spectrochim Acta. 1956;8:249–81.
Bellamy LJ. The infra-red spectra of complex molecules. London: Springer; 1975.
Blout ER, Fields M, Karplus R. J Am Chem Soc. 1948;70(1):194–8.
Hadzi D, Sheppard N. P R Soc A. 1953;216:247–66.
Hadzi D, Pintar M. Spectrochim Acta. 1958;12:162–88.
Lin-Vien D, Colthup NB, Fateley WG, Grasselli JG. The handbook of infrared and Raman characteristic frequencies of organic molecules. London: Academic; 1991.
Katritzky AR. Q Rev, Chem Soc. 1959;13:353–73.
Arrabal C, Cortijo M, Fernandez de Simon B, Garcia Vallejo MC, Cadahía E. Biochem Syst Ecol. 2005;33:1007–16.
Arrabal C, Cortijo M, Fernández de Simón B, García-Vallejo MC, Cadahía E. Holzforschung. 2002;56(3):261–6.
Rezzi S, Bighelli A, Castola V, Casanova J. Ind Crop Prod. 2005;21(1):71–9.
Mosini V, Samperi R. Phytochemistry. 1985;24(4):859–61.
Joye Jr NM, Lawrence RV. J Chem Eng Data. 1967;12(2):279–82.
Gref R. Eur J of Forest Pathol. 1987;17(4–5):227–30.
Gören AC, Bilsel G, Öztürk AH, Topçu G. Nat Prod Commun. 2010;11:1729–32.
Azémard C, Vieillescazes C, Ménager M. Microchem J. 2014;112:137–49.
Doménech-Carbó MT, Osete-Cortina L, de la Cruz CJ, Bolívar-Galiano F, Romero-Noguera J, Fernández-Vivas MA, et al. Anal Bioanal Chem. 2006;385(7):1265–80.
Romero-Noguera J, Bolívar-Galiano FC, Ramos-López JM, Fernández-Vivas MA, Martín-Sánchez I. Biodeteriorat Biodegrad. 2008;62(4):427–33.
Scalarone D, Lazzari M, Chiantore O. J Anal Appl Pyrol. 2002;64:345–61.
Ménager M, Azémard C, Vieillescazes C. Microchem J. 2014;114:32–41.
Ménager M, Perraud A, Vieillescazes C. Archéosciences. 2012;37:7–17.
Tirat S, Deganod I, Echard JP, Lattuati-Derieux A, Lluveras-Tenorio A, Marie A, et al. Microchem J. 2016;126:200–13.
Acknowledgements
We acknowledge the financial support received for the development of this study from MINECO (Spain), grant MAT2013-41127-R and Generalitat de Catalunya, grant 2014SGR-581.
We would like to thank the Centre de Restauració de Bens Mobles de Catalunya (CRBMC) for their help with the chromatographic analysis and for supplying the artwork samples. Also we would like to thank David Bertran Chavarria, curator of Jardí Botànic de Barcelona, for supplying the fresh resin samples and the Economic Botany Collection of the Royal Botanic Gardens, Kew, in London, for supplying dated ancient resins.
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Beltran, V., Salvadó, N., Butí, S. et al. Ageing of resin from Pinus species assessed by infrared spectroscopy. Anal Bioanal Chem 408, 4073–4082 (2016). https://doi.org/10.1007/s00216-016-9496-x
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DOI: https://doi.org/10.1007/s00216-016-9496-x