Skip to main content
SpringerLink
Log in

Olefin metathesis meets rubber chemistry and technology

  • Review
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

This article summarizes possible applications of olefin metathesis in rubber chemistry and technology. There are three main research directives with valuable contributions to the synthesis, recycling, and characterization of elastomers. First, ring opening metathesis polymerization as well as acyclic diene metathesis polycondensation yields polyalkenamers with cross-linkable double bonds, and thus can be used for the synthesis of defined rubbers serving as raw materials in rubber technology. Secondly, by cross metathesis reaction, natural rubber (and synthetic rubber) can be functionalized resulting in telechelic polymers or small molecule specialty chemicals. Thirdly, olefin metathesis offers the possibility of degrading the cross-linked rubber network into smaller soluble pieces, enabling different analytical possibilities such as characterization of cross-linking sites, determination of rubber, rubber additives and carbon black, and exploration of the rubber–metal adhesive interface. Additionally, this route can also be used for recycling of rubber products.

Graphical abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12
Fig. 13
Fig. 14
Fig. 15
Fig. 16
Fig. 17
Fig. 18
Fig. 19
Fig. 20
Fig. 21
Fig. 22

Similar content being viewed by others

References

  1. Grela K (2014) Olefin Metathesis: Theory and Practice. Wiley, New Jersey

    Book  Google Scholar 

  2. Grubbs RH, Wenzel AG, O’Leary DJ, Khosravi E (2015) Handbook of Metathesis, 2nd edn. John Wiley & Sons, New Jersey

    Google Scholar 

  3. Leitgeb A, Wappel J, Slugovc C (2010) Polymer 51:2927

    Article  CAS  Google Scholar 

  4. Banks RL, Bailey GC (1964) Ind Eng Chem Prod Res Dev 3:170

    Article  CAS  Google Scholar 

  5. Mol JC (2004) J Mol Catal A: Chem 213:39

    Article  CAS  Google Scholar 

  6. Schuster M, Blechert B (1997) Angew Chem Int Ed 36:2036

    Article  Google Scholar 

  7. Bose S, Ghosh S (2014) Proc Indian Nat Sci Acad 80:37

    Article  CAS  Google Scholar 

  8. Goodyear C (1844) Improvement in India-Rubber Fabrics. US Patent 3633 A, Jun 15, 1844

  9. Natta G, Dall’Asta G, Bassi IW, Carella G (1966) Makromol Chem 91:87

  10. Schrock RR (1990) Acc Chem Res 23:158

    Article  CAS  Google Scholar 

  11. Vougioukalakis GC, Grubbs RH (2010) Chem Rev 110:1746

    Article  CAS  Google Scholar 

  12. Kress S, Blechert S (2012) Chem Soc Rev 41:4389

    Article  CAS  Google Scholar 

  13. Schrock RR, Hoveyda AH (2003) Angew Chem Int Ed 42:4592

    Article  CAS  Google Scholar 

  14. Deraedt C, d’Halluin M, Astruc D (2013) Eur J Inorg Chem 4881

  15. Dall’Asta G (1974) Rubber Chem Technol 47:511

  16. Dounis P, Feast WJ, Kenwright AM (1995) Polymer 36:2787

    Article  CAS  Google Scholar 

  17. Katz TJ, Lee SJ, Acton N (1976) Tetrahedron Lett 47:4247

    Article  Google Scholar 

  18. Schleyer PvR, Williams JE, Blanchard KR (1970) J Am Chem Soc 92:2377

  19. Allinger NL, Sprague JT (1972) J Am Chem Soc 94:5734

    Article  CAS  Google Scholar 

  20. Hérisson PJ-L, Chauvin Y (1970) Makromol Chem 141:161

  21. Dimonie M, Coca S, Teodorescu M, Popescu L, Chipara M, Dragutan V (1994) J Mol Catal 90:117

    Article  CAS  Google Scholar 

  22. Keitz BK, Fedorov A, Grubbs RH (2012) J Am Chem Soc 134:2040

    Article  CAS  Google Scholar 

  23. Bielawski CW, Grubbs RH (2007) Prog Polym Sci 32:1

    Article  CAS  Google Scholar 

  24. Streck R (1989) ChemTech 19:498

    CAS  Google Scholar 

  25. Warel S (1987) Erdöl Erdgas Kohle 103:238

    Google Scholar 

  26. Evonik Industries, Vestenamer 8012: The rubber additive with unique properties, http://www.struktol.com/pdfs/Vestenamer%208012-Evonik.pdf (05.05.2015)

  27. Meisenheimer H, Steiger R, Marbach A, Diedrich KM, Dunn J, Karall G (2011) Encyclopedia of industrial chemistry (Rubber, 6. Synthesis by Radical and Other Mechanisms). Wiley-VCH Verlag, Weinheim

  28. Slugovc C (2014) Industrial Applications of olefin metathesis. In Grela K (ed), Olefin Metathesis: Theory and Practice. John Wiley & Sons, New Jersey, p 329

  29. Dräxler A (1981) Kaut Gummi Kunst 34:185

  30. Calderon N, Ofstead EA, Judy WA (1967) J Polym Sci, Part A: Polym Chem 5:2209

    Article  CAS  Google Scholar 

  31. Katz TJ, Han CC (1982) Organometallics 1:1093

    Article  CAS  Google Scholar 

  32. Preishuber-Pflugl P, Buchacher P, Eder E, Schitter RM, Stelzer F (1998) J Mol Catal A: Chem 133:151

    Article  CAS  Google Scholar 

  33. Shea KJ, Kim JS (1992) J Am Chem Soc 114:3044

    Article  CAS  Google Scholar 

  34. Walker R, Conrad RM, Grubbs RH (2009) Macromolecules 42:599

    Article  CAS  Google Scholar 

  35. Delaude L, Szypa M, Demonceau A, Noels AF (2002) Adv Synth Catal 6:344

    Google Scholar 

  36. Martinez H, Ren N, Matta ME, Hillmyer MA (2014) Polym Chem 5:3507

    Article  CAS  Google Scholar 

  37. Scheider WA, Mueller MF (1988) Makromol Chem 189:2823

    Article  Google Scholar 

  38. Anderson AW, Merckling NG (1955) Polymeric Bicyclo-[2.2.1]-2-heptene. US Patent 2,721,189, Oct 18, 1955; (1956) Chem Abstr 50:14596

  39. Ohm RF, Vial TM (1987) J Elastom Plast 10:15

    Google Scholar 

  40. Banasiak DS, Mozdzen EC, Byers JD (1987) Metallotetradecadiene compounds. US Patent 4,687,867 A, Aug 18, 1987; (1987) Chem Abstr 106:32344

  41. Kress J, Wesolek M, Osborn JA (1982) J Chem Soc Chem Commun 514

  42. Kress J, Osborn JA, Greene RME, Ivin KJ, Rooney JJ (1987) J Am Chem Soc 109:899

    Article  CAS  Google Scholar 

  43. Schrock RR, Feldman J, Cannizzo LF, Grubbs RH (1987) Macromolecules 20:1172

    Article  Google Scholar 

  44. Floros G, Saragas N, Paraskevopoulou, Psaroudakis N, Koinis S, Pitsikalis M, Hadjichristidis N, Mertis K (2012) Polymers 4:1657

  45. Murdzek JS, Schrock RR (1987) Organometallics 6:1373

    Article  CAS  Google Scholar 

  46. Bazan GC, Schrock RR, Cho HN, Gibson VC (1991) Macromolecules 24:4495

    Article  CAS  Google Scholar 

  47. Heroguez V, Fontanille M (1994) J Polym Sci (Part A) 32:1755

    Article  CAS  Google Scholar 

  48. Hatjopoulos JD, Register RA (2005) Macromolecules 38:10320

    Article  CAS  Google Scholar 

  49. Schwab B, France MB, Ziller JW, Grubbs RH (1995) Angew Chem Int Ed 34:2039

    Article  CAS  Google Scholar 

  50. Hafner A, van der Schaaf PA, Mühlebach A (1996) Chimia 50:131

    CAS  Google Scholar 

  51. Truett WL, Johnson DR, Bobinson IM, Montague BA (1960) J Am Chem Soc 82:2337

    Article  CAS  Google Scholar 

  52. Gilliom LR, Grubbs RH (1986) J Am Chem Soc 108:733

    Article  CAS  Google Scholar 

  53. Wallace KC, Liu AH, Dewan JC, Schrock RR (1988) J Am Chem Soc 110:4964

    Article  CAS  Google Scholar 

  54. Brumaghim JL, Girolami GS (1999) Organometallics 18:1923

    Article  CAS  Google Scholar 

  55. Dall’Asta G, Mazzanti G, Natta G, Porri L (1962) Makromol Chem Rapid Comm 56:224

  56. Natta G, Dall´Asta G, Porri L (1965) Makromol Chem 81:253

  57. Wu Z, Wheeler DR, Grubbs RH (1992) J Am Chem Soc 114:146

    Article  CAS  Google Scholar 

  58. Flook MM, Jiang AJ, Schrock RR, Müller P, Hoveyda AH (2009) J Am Chem Soc 131:7962

    Article  CAS  Google Scholar 

  59. Wu Z, Grubbs RH (1994) J Mol Catal 90:39

    Article  CAS  Google Scholar 

  60. Natta G, Dall´Asta G, Mazzanti G (1964) Angew Chem Int Ed 3:723

  61. Günther P, Haas F, Marwede G, Nützel K, Oberkirch W, Pampus G, Schön N, Witte J (1970) Angew Makromol Chem 14:87

    Article  Google Scholar 

  62. Dall’Asta, Scaglione P (1964) Rubber Chem Technol 18:1235

  63. Trzaska ST, Lee L-BW, Register RA (2000) Macromolecules 33:9215

  64. Haas F, Nützel K, Pampus G, Theisen D (1970) Rubber Chem Technol 43:1116

    Article  CAS  Google Scholar 

  65. Hejl A, Schermann OA, Grubbs RH (2005) Macromolecules 38:7214

    Article  CAS  Google Scholar 

  66. Vasile C (2000) Handbook of Polyolefins, 2nd edn. Marcel Dekker, New York, p 131

    Book  Google Scholar 

  67. Baughman TW, Wagener KB (2005) Adv Polym Sci 176:1

    Article  CAS  Google Scholar 

  68. Bachler PR, Wagener KB (2015) Monatsh Chem. doi:10.1007/s00706-015-1479-7

    Google Scholar 

  69. Wagener KB, Boncella JM, Nel JG (1991) Macromolecules 24:2649

    Article  CAS  Google Scholar 

  70. Wagener KB, Nel JG, Duttweiler RP, Hillmyer MA, Boncella JM, Konzelman J, Smith DW, Puts R, Willoughby L (1990) Rubber Chem Technol 64:83

    Article  Google Scholar 

  71. Zuech EA, Hughes WB, Kubicek DH, Kittleman ET (1970) J Am Chem Soc 92:528

    Article  CAS  Google Scholar 

  72. Dall’Asta G, Stigliani G, Greco A, Motta L (1973) Chim Ind 55:142

  73. Brosse JC, Campistron I, Derouet D, el Hamdaoui A, Houdayer S, Reyx D, Ritoit-Gillier S (2000) J Appl Polym Sci 78:1461

    Article  CAS  Google Scholar 

  74. Maughon BR, Grubbs RH (1997) Macromolecules 30:3459

    Article  CAS  Google Scholar 

  75. Perrott MG, Novak BM (1996) Macromolecules 29:1817

    Article  CAS  Google Scholar 

  76. Schneider MF, Gantner C, Obrecht W, Nuyken O (2010) Macromol Rapid Commun 31:1731

    Article  CAS  Google Scholar 

  77. Smit T, Müller K, Dahmen S, Negrete L, Sturm B (2012) Rubber material with barrier material made of cycloolefin copolymers. WO 2014026865 A1, Feb 20, 2014; (2014) Chem Abstr 160:311898

  78. Buchmeiser MR, Ahmad I, Gurram V, Kumar PS (2011) Macromolecules 44:4098

    Article  CAS  Google Scholar 

  79. Bornand M, Chen P (2005) Angew Chem Int Ed 44:7909

    Article  CAS  Google Scholar 

  80. Torker S, Müller A, Sigrist R, Chen P (2010) Organometallics 29:2735

    Article  CAS  Google Scholar 

  81. Lichtenheldt M, Wang D, Vehlow K, Reinhardt I, Kühnel C, Decker U, Blechert S, Buchmeiser MR (2009) Chem Eur J 15:9451

    Article  CAS  Google Scholar 

  82. Cetinkaya S, Karabulut S, Imamoglu Y (2007) NATO Sci Ser 243:355

    CAS  Google Scholar 

  83. Cetinkaya S, Karabulut S, Imamoglu Y (2005) Eur Polym J 41:467

    Article  CAS  Google Scholar 

  84. Karabulut A, Cetinkaya S, Imamoğlu Y (2005) Appl Organometal Chem 19:997

    Article  CAS  Google Scholar 

  85. Hino T, Inoue N, Endo T (2005) J Polym Sci A Polym Chem 43:6599

    Article  CAS  Google Scholar 

  86. Gringolts ML, Denisova YI, Shandryuk GA, Krentsel LB, Litmanovich AD, Finkelshtein ES, Kudryavtsev YV (2015) RSC Adv 5:316

    Article  CAS  Google Scholar 

  87. Otsuka H, Muta T, Sakada M, Maeda T, Takahara A (2009) Chem Commun 1073

  88. Ast W, Rheinwald G, Kerber R (1976) Makromol Chem 177:1341

    Article  CAS  Google Scholar 

  89. Tian Q, Larock RC (2002) J Am Oil Chem Soc 79:479

    Article  CAS  Google Scholar 

  90. Spurcaciu B, Buzdugan E, Nicolae C-A, Dragutan I, Dragutan V (2007) NATO Sci Ser 243:347

    CAS  Google Scholar 

  91. Jeong W, Mauldin TC, Larock RC, Kessler MR (2009) Macromol Mat Eng 294:756

    Article  CAS  Google Scholar 

  92. Caster KC, Walls RD (2002) Adv Synth Catal 344:764

    Article  CAS  Google Scholar 

  93. Hillmyer MA, Grubbs RH (1993) Macromolecules 25:872

    Article  Google Scholar 

  94. Thomas RM, Grubbs RH (2010) Macromolecules 43:3705

    Article  CAS  Google Scholar 

  95. Ji S, Hoye TR, Macosko CW (2004) Macromolecules 37:5485

    Article  CAS  Google Scholar 

  96. Pitet LM, Hillmyer MA (2011) Macromolecules 44:2378

    Article  CAS  Google Scholar 

  97. Annunziata L, Fouquay S, Michaud G, Simon F, Guillaume SM Carpentier J-F (2013) Polym Chem 4:1313

  98. Mathers RT, McMahon KC, Damodaran K, Retarides CJ, Kelley DJ (2006) Macromolecules 39:8982

    Article  CAS  Google Scholar 

  99. Brzezinska KR, Wagener KB, Burns GT (1999) J Polym Sci A Polym Chem 37:849

    Article  CAS  Google Scholar 

  100. Nubel PO, Lutman CA, Yokelson HB (1994) Macromolecules 27:7000

    Article  CAS  Google Scholar 

  101. Tamura H, Maeda N, Matsumoto R, Nakayama A, Hayashi H, Ikushima K, Kuraya M (1999) J Macromol Sci A Pure Appl Chem 36:1153

    Article  Google Scholar 

  102. Brzezinska KR, Deming TJ (2001) Macromolecules 34:4348

    Article  CAS  Google Scholar 

  103. Schwendeman JE, Wagener KB (2009) Macromol Chem Phys 210:1818

    Article  CAS  Google Scholar 

  104. Ast W, Hummel K (1970) Naturwissenschaften 57:545

    Article  CAS  Google Scholar 

  105. Seyferth K, Taube R, Dahlke M (1981) Ester group-terminated polyolefins. Ger. East Pat. 146,053, Jan 21, 1981; (1981) Chem Abstr 95:43978

  106. Marmo JC, Wagener KB (1993) Macromolecules 26:2137

    Article  CAS  Google Scholar 

  107. Marmo JC, Wagener KB (1995) Macromolecules 28:2602

    Article  CAS  Google Scholar 

  108. Chasmawala M, Chung TC (1995) Macromolecules 28:1333

    Article  CAS  Google Scholar 

  109. Solanky SS, Campistron I, Laguerre A, Pilard J-F (2005) Macromol Chem Phys 206:1057

    Article  CAS  Google Scholar 

  110. Sadaka F, Campistron I, Laguerre A, Pilard J-F (2013) Polym Degrad Stabil 98:736

    Article  CAS  Google Scholar 

  111. Tlenkopatchev MA, Gutièrrez S (2009) Rev Latin Am Metal Mater S1:1463

    Google Scholar 

  112. Saetung N, Campistron I, Pascual S, Pilard J-F, Fontaine L (2011) Macromolecules 44:784

    Article  CAS  Google Scholar 

  113. Martìnez A, Gutièrrez S, Tlenkopatchev MA (2013) Nat Sci 5:857

    Google Scholar 

  114. Martìnez A, Gutièrrez S, Tlenkopatchev MA (2012) Molecules 17:6001

    Article  CAS  Google Scholar 

  115. Fomine S, Tlenkopatchev MA (2010) Organometallics 29:1580

    Article  CAS  Google Scholar 

  116. Gutìerrez S, Tlenkopatchev MA (2011) Polym Bull 66:1029

    Article  CAS  Google Scholar 

  117. Thorn-Csanyi E, Ruhland K (1999) Macromol Chem Phys 200:1662

    Article  CAS  Google Scholar 

  118. Thorn-Csanyi E, Hammer J, Zilles JU (1994) Macromol Rapid Commun 15:797

    Article  CAS  Google Scholar 

  119. Reyx D, Campistron I (1997) Angew Makromol Chem 247:197

    Article  CAS  Google Scholar 

  120. Tlenkopatchev MA, Barkenas A, Fomine S (2001) Macromol Theo Simul 10:441

    Article  CAS  Google Scholar 

  121. Fainleib A, Pires RV, Lucas EF, Soares BG (2013) Polìmeros 23:441

    Article  CAS  Google Scholar 

  122. Obrecht W, Müller JM, Nuyken O, Berke H, Meca L, Triscikova L (2008) Method for the degradation of nitrile rubber by metathesis in the presence of Ruthenium- or Osmium-based catalysts. US Patent 7,470,750 B2, Dec 30, 2008; (2007) Chem Abstr 146:296420

  123. Guèrin F (2004) Process for the preparation of low molecular weight hydrogenated nitrile rubber. US Patent 6,673,881 B2, Jan 6, 2004; (2002) Chem Abstr 138:40520

  124. Stelzer F, Hobisch G, Pongratz T, Hummel K (1988) J Mol Catal 46:433

    Article  Google Scholar 

  125. Zhan Z-YJ (2012) Methods of modifying polymers with highly active and selective metathesis catalysts. US 2012/0252982 A1, Oct 4, 2012; (2012) Chem Abstr 157:549087

  126. Hummel K (1985) J Mol Catal 28:381

    Article  CAS  Google Scholar 

  127. Thorn-Csanyi E, Perner H (1979) Makromol Chem 180:919

    Article  CAS  Google Scholar 

  128. Hummel K, Ast W (1973) Makormol Chem 166:39l

    Article  Google Scholar 

  129. Lorber F, Hummel K (1973) Makromol Chem 171:257

    Article  CAS  Google Scholar 

  130. Thorn-Csanyi E, Perner H (1986) J Mol Catal 36:187

    Article  CAS  Google Scholar 

  131. Hummel K (1982) Pure Appl Chem 54:351

    Article  CAS  Google Scholar 

  132. Thummer R, Stelzer F, Hummel K (1975) Makromol Chem 176:1703

    Article  CAS  Google Scholar 

  133. Stelzer F, Hummel K, Graimann C, Hobisch J, Martl MG (1987) Makromol Chem 188:1795

    Article  CAS  Google Scholar 

  134. Ast W, Bosch H, Kerber R (1979) Angew Makromol Chem 76:67

    Article  Google Scholar 

  135. Kumar VNG, Hummel K, Hönig H (1981) Angew Makromol Chem 96:93

    Article  CAS  Google Scholar 

  136. Korshak YV, Tlenkopatchev MA, Dolgoplosk BA, Avdeikina EG, Kuterov DF (1982) J Mol Catal 15:207

    Article  CAS  Google Scholar 

  137. Hummel K, Kiattanavith N, Bernard E (1993) Angew Makromol Chem 207:137

    Article  CAS  Google Scholar 

  138. Alimuniar A, Yarmo MA, Rahman MZA Kohjiya S, Ikeda Y, Yamashita S (1990) Polym Bull 23:119

  139. Wagener KB, Puts RD, Smith DW Jr (1991) Makromol Chem, Rapid Commun 12:419

    Article  CAS  Google Scholar 

  140. Thorn-Csanyi E (1994) Rubber Chem Technol 67:786

    Article  CAS  Google Scholar 

  141. Craig SW, Manzer JA, Coughlin EB (2001) Macromolecules 34:7929

    Article  CAS  Google Scholar 

  142. Sedransk KL, Kaminski CF, Hutchings LR, Moggridge GD (2011) Polym Degrad Stabil 96:1074

    Article  CAS  Google Scholar 

  143. Sashuk V, Peeck LH, Plenio H (2010) Chem Eur J 16:3983

    Article  CAS  Google Scholar 

  144. Wolf S, Plenio H (2011) Green Chem 13:2008

    Article  CAS  Google Scholar 

  145. Ouardad S, Peruch F (2014) Polym Degrad Stabil 99:249

    Article  CAS  Google Scholar 

  146. Hummel K, Groyer S, Lechner H (1982) Kaut Gummi Kunst 35:731

    CAS  Google Scholar 

  147. Grießer H, Hummel K (1980) Colloid Polymer Sci 258:467

    Article  Google Scholar 

  148. Stelzer F, Hummel K, Sommer F, Baumegger E, Lesiak MC (1987) Rubber Chem Technol 60:600

    Article  CAS  Google Scholar 

  149. Hummel K, Raithofer G (1976) Angew Makromol Chem 50:183

    Article  CAS  Google Scholar 

  150. Hummel K, Stelzer F, Hobisch G, Hartmann B (1987) Angew Makromol Chem 155:143

    Article  CAS  Google Scholar 

  151. van Ooij WJ, Harakuni PB, Buytaert G (2009) Rubber Chem Technol 82:315

    Article  Google Scholar 

  152. Leimgruber S, Kern W, Hochenauer R, Melmer M, Holzner A, Trimmel G (2015) Rubber Chem Technol. doi:10.5254/rct.14.85.946

    Google Scholar 

  153. Zümreoglu-Karan B, Bozkurt C, Imamoglu (1992) Polymer J 24:25

  154. Demel S (2003) PhD Thesis, Graz University of Technology, p 116

  155. Wolf S, Plenio H (2013) Green Chem 15:315

    Article  CAS  Google Scholar 

Download references

Acknowledgments

A part of this work was performed at the Polymer Competence Center Leoben GmbH (PCCL, Austria) within the framework of the COMET-program of the Federal Ministry for Transport, Innovation and Technology and Federal Ministry for Economy, Family and Youth with contributions by Graz University of Technology and Semperit Technical Products GmbH. The PCCL is funded by the Austrian Government and the State Governments of Styria, Lower Austria and Upper Austria.

Author information

Authors and Affiliations

  1. Institute for Chemistry and Technology of Materials, Graz University of Technology, Stremayrgasse 9, 8010, Graz, Austria

    Simon Leimgruber & Gregor Trimmel

  2. Polymer Competence Center Leoben GmbH, Leoben, Austria

    Simon Leimgruber & Gregor Trimmel

Authors
  1. Simon Leimgruber
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Gregor Trimmel
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Gregor Trimmel.

Additional information

Dedicated to our mentor Franz Stelzer.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Leimgruber, S., Trimmel, G. Olefin metathesis meets rubber chemistry and technology. Monatsh Chem 146, 1081–1097 (2015). https://doi.org/10.1007/s00706-015-1501-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-015-1501-0

Keywords

Search

Navigation