Skip to main content
SpringerLink
Log in

Hydrogenation of Indene–Coumarone Resin on Palladium Catalysts for Use in Polymer Adhesives

  • Macromolecular Compounds and Polymeric Materials
  • Published:
Russian Journal of Applied Chemistry Aims and scope Submit manuscript

Abstract

Hydrogenation of indene–coumarone resin on commercial palladium catalysts, including crusted catalysts, was studied. The process parameters were optimized to reach the maximal hydrogenation of aromatic fragments with minimal thermal degradation of the macromolecules. The optimum conditions are as follows: temperature 230°C, pressure 3 MPa, resin concentration in the solvent 10–25 wt %. Comparative analysis of the activity of the tested catalysts shows that palladium on activated carbon exhibits the highest activity. The use of indene–coumarone resin as an adhesive component of polymer hot-melt and pressure-sensitive adhesives was considered. The rheology of the initial resins and adhesives based on them, the phase state of the formulations, and their adhesiveness were compared. The advantage of using the hydrogenated resin for preparing polymer adhesives based on styrene–isoprene–styrene triblock copolymer was demonstrated.

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

Similar content being viewed by others

References

  1. Mildenberg, R., Zander, M., and Collin, G., Hydrocarbon Resins, Weinheim: VCH, 1997.

    Book  Google Scholar 

  2. Dumskii, Yu.V., No, B.I., and Butov, G.M., Khimiya i tekhnologiya neftepolimernykh smol (Chemistry and Technology of Petroleum Polymer Resins), Moscow: Khimiya, 1999, pp. 249–259.

    Google Scholar 

  3. Dumskii, Yu.V., Neftepolimernye smoly (Petroleum Polymer Resins), Moscow: Khimiya, 1988, pp. 131–138.

    Google Scholar 

  4. Poh, B.T. and Chee, C.L., Int. J. Polym. Mater. Polym. Biomater., 2007, vol. 56, no. 3, pp. 247–255.

    Article  CAS  Google Scholar 

  5. Slavgorodskaya, O.I., Bondaletov, V.G., Tulina, N.L., Ustimenko, Yu.P., and Zombek, P.V., Fundam. Issled., 2013, no. 8-3, pp. 726–730.

  6. Carmody, W.H., Ind. Eng. Chem., 1940, vol. 32, no. 4, pp. 525–527.

    Article  CAS  Google Scholar 

  7. Coca, J., Rosal, R., Diez, F.V., and Sastre, H., J. Chem. Tech. Biotechnol., 1992, vol. 53, pp. 365–371.

    Article  CAS  Google Scholar 

  8. Carmody, W.H. and Kelly, H.E., Ind. Eng. Chem., 1940, vol. 32, no. 6, pp. 771–775.

    Article  CAS  Google Scholar 

  9. Carmody, W.H., Kelly, H.E., and Sheenan, W., Ind. Eng. Chem., 1940, vol. 32, no. 5, pp. 684–692.

    Article  CAS  Google Scholar 

  10. Patent US 2139722, Publ. 1936.

  11. Patent US 2266676, Publ. 1938.

  12. Patent US 2319959, Publ. 1941.

  13. Hatano, A., Iwase, Y., and Ashida, K., J. Macromol. Sci., Part A: Chemistry: Pure Appl. Chem., 1978, vol. 12, no. 5, pp. 647–659.

    Article  Google Scholar 

  14. Carmody, W.H., Ind. Eng. Chem., 1942, vol. 34, no. 1, pp. 74–78.

    Article  CAS  Google Scholar 

  15. Patent US 2416903, Publ. 1943.

  16. Patent US 2416904, Publ. 1943.

  17. Patent US 2416905, Publ. 1943.

  18. Xu, D., Carbonell, R.G., Kiserow, D.J., and Roberts, G.W., Ind. Eng. Chem. Res., 2003, vol. 42, pp. 3509–3515.

    Article  CAS  Google Scholar 

  19. Ness, J.S., Brodil, J.C., Bates, F.S., Hahn, S.F., Hucul, D.A., and Hillmyer, M.A., Macromolecules, 2002, vol. 35, pp. 602–609.

    Article  CAS  Google Scholar 

  20. Han, K., Zuo, H., Zhu, Z., Cao, G., Lu, C., and Wang, Y., Ind. Eng. Chem. Res., 2013, vol. 52, pp. 17750–17759.

    Article  CAS  Google Scholar 

  21. Sae-Ma, N., Praserthdam, P., Panpranot, J., Chaemchuen, S., Dokjamp, S., Suriye, K., and Rempel, G.L., J. Appl. Polym. Sci., 2010, vol. 117, pp. 2862–2869.

    CAS  Google Scholar 

  22. Fuentes-Ordonez, E.G., Salbidegoitia, J.A., GonzalezMarcos, M.P., and Gonzalez-Velasco, J.R., Ind. Eng. Chem. Res., 2013, vol. 52, no. 42, pp. 14798–14807.

    Article  CAS  Google Scholar 

  23. Shabtai, J., Xiao, X., and Zmierczak, W., Energy Fuels, 1997, vol. 11, pp. 76–87.

    Article  CAS  Google Scholar 

  24. Zmierczak, W., Xiao, X., and Shabtai, J., Fuel Process. Technol., 1996, vol. 49, pp. 31–48.

    Article  CAS  Google Scholar 

  25. Dong, L.B., Turgman-Cohen, S., Roberts, G.W., and Kiserow, D.J., Ind. Eng. Chem. Res., 2010, vol. 49, pp. 11280–11286.

    Article  CAS  Google Scholar 

  26. Shirai, M., Torii, K., and Arai, M., Stud. Surf. Sci. Catal., 2000, vol. 130, pp. 2105–2110.

    Article  Google Scholar 

  27. Malkin, A.Y., Ilyin, S.O., Arinina, M.P., and Kulichikhin, V.G., Colloid Polym. Sci., 2017, vol. 295, no. 4, pp. 555–563.

    Article  CAS  Google Scholar 

  28. Brantseva, T., Antonov, S., Kostyuk, A., Ignatenko, V., Smirnova, N., Korolev, Y., Tereshin, A., and Ilyin, S., Eur. Polym. J., 2016, vol. 76, pp. 228–244.

    Article  CAS  Google Scholar 

  29. Ilyin, S.O., Kulichikhin, V.G., and Malkin, A.Y., Polym. Sci., Ser. A, 2013, vol. 55, no. 8, pp. 503–509.

    Article  CAS  Google Scholar 

  30. Ilyin, S.O., Arinina, M.P., Malkin, A.Y., and Kulichikhin, V.G., Colloid J., 2016, vol. 78, no. 5, pp. 608–615.

    Article  CAS  Google Scholar 

  31. Mironova, M.V. and Ilyin, S.O., Fuel, 2018, vol. 232, pp. 290–298.

    Article  CAS  Google Scholar 

  32. Van Puyvelde, P., Vananroye, A., Cardinaels, R., and Moldenaers, P., Polymer, 2008, vol. 49, pp. 5363–5372.

    Article  CAS  Google Scholar 

  33. Ilyin, S.O., Kostyuk, A.V., Ignatenko, V.Y., Smirnova, N.M., Alekseeva, O.A., Petrukhina, N.N., and Antonov, S.V., Russ. J. Appl. Chem., 2018, vol. 91, no. 12, pp. 1945–1956.

    Article  CAS  Google Scholar 

  34. Ilyin, S O., Malkin, A.Y., Kulichikhin, V.G., Denisova, Y.I., Krentsel, L.B., Shandryuk, G.A., Litmanovich, A.D., Litmanovich, E.A., Bondarenko, G.N., and Kudryavtsev, Y.V., Macromolecules, 2014, vol. 47, no. 14, pp. 4790–4804.

    Article  CAS  Google Scholar 

  35. Benedek, I. and Feldstein, M.M., Technology of Pressure-Sensitive Adhesives and Products, Boca Raton, FL: CRC, 2008.

    Book  Google Scholar 

  36. Creton, C. and Shull, K.R., Handbook of Pressure-Sensitive Adhesives and Products: Fundamentals of Pressure Sensitivity, Benedek, I. and Feldstein, M.M., Eds., Boca Raton: CRC, 2009, ch. 6, pp. 6–1–6–26.

Download references

Funding

The study was performed within the framework of the government assignment for the Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences.

Author information

Authors and Affiliations

  1. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, Moscow, 119991, Russia

    S. O. Ilyin, N. N. Petrukhina, A. V. Kostyuk, M. P. Filatova, S. V. Antonov & A. L. Maksimov

  2. Gubkin University, National University of Oil and Gas, Moscow, 119991, Russia

    E. G. Dzhabarov

  3. Moscow State University, Moscow, 119991, Russia

    A. L. Maksimov

Authors
  1. S. O. Ilyin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. N. N. Petrukhina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. V. Kostyuk
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. E. G. Dzhabarov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. M. P. Filatova
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. S. V. Antonov
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. A. L. Maksimov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to N. N. Petrukhina.

Additional information

Conflict of Interest

A.L. Maksimov is the Editor-in-Chief of Zhurnal Prikladnoi Khimii/Russian Journal of Applied Chemistry. The other authors have no confl ict of interest.

Russian Text © The Author(s), 2019, published in Zhurnal Prikladnoi Khimii, 2019, Vol. 92, No. 8, pp. 1051–1060.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ilyin, S.O., Petrukhina, N.N., Kostyuk, A.V. et al. Hydrogenation of Indene–Coumarone Resin on Palladium Catalysts for Use in Polymer Adhesives. Russ J Appl Chem 92, 1143–1152 (2019). https://doi.org/10.1134/S1070427219080135

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070427219080135

Keywords

Search

Navigation