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Journal of Material Cycles and Waste Management

, Volume 20, Issue 1, pp 568–577 | Cite as

Degradation of anhydride-cured epoxy resin using simultaneously recyclable solvent and organic base catalyst

  • Lipeng Zhang
  • Jie Liu
  • Weidong Nie
  • Kai Wang
  • Yanhui Wang
  • Xiuyun Yang
  • Tao Tang
ORIGINAL ARTICLE
  • 241 Downloads

Abstract

Alkaline catalyst is usually used for solvolysis of thermoplastic and thermoset polymers containing ester bonds. However, inorganic catalyst is difficult to remove from products of resin degradation. Here, we reported an efficient and mild degradation method using an organocatalyst, N-methyl-4-piperidinol, in ethylene glycol to degrade methylcyclohexene-1,2-dicarboxylic anhydride (MeTHPA)-cured epoxy resin. N-Methyl-4-piperidinol and ethylene glycol were simultaneously recovered by vacuum distillation. The effects of reaction temperature and catalyst concentration on the reaction rate and kinetics of the degradation reaction were analyzed. The recovery and reuse of ethylene glycol and the catalyst for three cycles were also demonstrated. The degradation products from the epoxy resin were identified by electrospray ionization-mass spectrometry (ESI-MS), and a transesterification mechanism for the degradation of epoxy resin was proposed.

Keywords

Epoxy resin Organic base Recyclable Ethylene glycol Degradation 

Notes

Acknowledgements

The work is financially supported by the National Natural Science Foundation of China (NSFC 51103154), the Main Direction Program of Knowledge Innovation of Chinese Academy of Sciences (KGCX2-YW-230 and KGCX2-EW-211) and Jilin Province Science and Technology Development Program (20140204057GX).

References

  1. 1.
    Grause G, Buekens A, Sakata Y, Okuwaki A, Yoshioka T (2011) Feedstock recycling of waste polymeric material. J Mater Cycles Waste Manag 13:265–282CrossRefGoogle Scholar
  2. 2.
    Lopez-Fonseca R, Duque-Ingunza I, Rivas BD, Arnaiz S, Gutierrez-Ortiz JI (2010) Chemical recycling of post-consumer PET wastes by glycolysis in the presence of metal salts. Polym Degrad Stabil 95:1022–1028CrossRefGoogle Scholar
  3. 3.
    Nunes CS, da Silva MJV, da Silva DC, Freitas AD, Rosa FA, Rubira AF, Muniz EC (2014) PET depolymerisation in supercritical ethanol catalysed by [Bmim][BF4]. RSC Adv 4:20308–20316CrossRefGoogle Scholar
  4. 4.
    Kamimura A, Kaiso K, Suzuki S, Oishi Y, Ohara Y, Sugimoto T, Kashiwagi K, Yoshimoto M (2011) Direct conversion of polyamides to ω-hydroxyalkanoic acid derivatives by using supercritical MeOH. Green Chem 13:2055–2061CrossRefGoogle Scholar
  5. 5.
    Pinero R, Garcia J, Cocero MJ (2005) Chemical recycling of polycarbonate in a semi-continuous lab-plant. A green route with methanol and methanol-water mixtures. Green Chem 7:380–387CrossRefGoogle Scholar
  6. 6.
    Okubo K, Sugeno T, Tagaya H (2015) Chemical recycling of poly(p-phenylene sulfide) in high temperature fluids. Polym Degrad Stabil 111:109–113CrossRefGoogle Scholar
  7. 7.
    Oliveux G, Dandy LO, Leeke GA (2015) Degradation of a model epoxy resin by solvolysis routes. Polym Degrad Stabil 118:96–103CrossRefGoogle Scholar
  8. 8.
    Ibarra RM, Sasaki M, Goto M, Quitain AT, Montes SMG, Aguilar-Garib JA (2015) Carbon fiber recovery using water and benzyl alcohol in subcritical and supercritical conditions for chemical recycling of thermoset composite materials. J Mater Cycles Waste Manag 17:369–379CrossRefGoogle Scholar
  9. 9.
    Okajima I, Hiramatsu M, Shimamura Y, Awaya T, Sako T (2014) Chemical recycling of carbon fiber reinforced plastic using supercritical methanol. J Supercrit Fluids 91:68–76CrossRefGoogle Scholar
  10. 10.
    Kamimura A, Yamamoto S, Yamada K (2011) Depolymerization of unsaturated polyesters and waste fiber-reinforced plastics by using ionic liquids: the use of microwaves to accelerate the reaction rate. Chemsuschem 4:644–649CrossRefGoogle Scholar
  11. 11.
    Liu Y, Liu J, Jiang ZW, Tang T (2012) Chemical recycling of carbon fibre reinforced epoxy resin composites in subcritical water: synergistic effect of phenol and KOH on the decomposition efficiency. Polym Degrad Stabil 97:214–220CrossRefGoogle Scholar
  12. 12.
    Nie WD, Liu J, Liu WB, Wang J, Tang T (2015) Decomposition of waste carbon fiber reinforced epoxy resin composites in molten potassium hydroxide. Polym Degrad Stabil 111:247–256CrossRefGoogle Scholar
  13. 13.
    Morin C, Loppinet-Serani A, Cansell F, Aymonier C (2012) Near- and supercritical solvolysis of carbon fibre reinforced polymers (CFRPs) for recycling carbon fibers as a valuable resource: state of the art. J Supercrit Fluids 66:232–240CrossRefGoogle Scholar
  14. 14.
    Gersifi KE, Durand G, Tersac G (2006) Solvolysis of bisphenol A diglycidyl ether/anhydride model networks. Polym Degrad Stab 91:690–702CrossRefGoogle Scholar
  15. 15.
    Nakagawa M, Kuriya H, Shibata K (2009) Characterization of CFRP using recovered carbon fibers from waste CFRP. In: The 5th symposium on feedstock and mechanical recycling of polymeric materials (ISFR 2009), Chengdu, China, pp 241–244Google Scholar
  16. 16.
    Kamimura A, Yamada K, Kuratani T, Oishi Y, Watanabe T, Yoshida T, Tomonaga F (2008) DMAP as an effective catalyst to accelerate the solubilization of waste fiber-reinforced plastics. Chemsuschem 1:845–850CrossRefGoogle Scholar
  17. 17.
    Fukushima K, Coulembier O, Lecuyer JM, Almegren HA, Alabdulrahman AM, Alsewailem FD, Mcneil MA, Dubois P, Waymouth RM, Horn HW, Rice JE, Hedrick JL (2011) Organocatalytic depolymerization of poly(ethylene terephthalate). J Polym Sci Part A Polym Chem 49:1273–1281CrossRefGoogle Scholar
  18. 18.
    Pinero-Hernanz R, Garcia-Serna J, Dodds C, Hyde J, Poliakoff M, Cocero SMJ, Kingman S, Pickering S, Lester E (2008) Chemical recycling of carbon fibre composites using alcohols under subcritical and supercritical conditions. J Supercrit Fluids 46:83–92CrossRefGoogle Scholar
  19. 19.
    Liu J, Wang K, Ma L, Tang T (2016) Insight into the role of potassium hydroxide for accelerating the degradation of anhydride-cured epoxy resin in subcritical methanol. J Supercrit Fluids 107:605–611CrossRefGoogle Scholar

Copyright information

© Springer Japan 2017

Authors and Affiliations

  1. 1.School of Chemistry and Environmental EngineeringChangchun University of Science and TechnologyChangchunChina
  2. 2.State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied ChemistryChinese Academy of SciencesChangchunChina

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