Latent catalytic systems for ring-opening metathesis-based thermosets

Journal of Thermal Analysis - Tập 96 - Trang 705-713 - 2009
T. C. Mauldin1, M. R. Kessler2
1Department of Chemistry, Iowa State University, Ames, USA
2Department of Materials Science and Engineering, Iowa State University, Ames, USA

Tóm tắt

Synthesis and curing activity of latent ring-opening metathesis polymerization (ROMP)-based catalytic systems are reported using polydicyclopentadiene (pDCPD) as a model system. Differential scanning calorimetry (DSC) is used to monitor the ROMP reactions and to characterize the cured networks. These systems are either slow or completely inactive at ambient temperatures, yet at high temperatures the superior curing activity of other ROMP catalysts are retained. The resulting thermosets show glass transition temperatures from 10 to 25 °C higher than when cured with other ROMP catalysts.

Tài liệu tham khảo

Ivin KJ, Mol JC. Olefin metathesis, metathesis polymerization. San Diego, CA: Academic Press; 1997. Bielawski CW, Grubbs RH. Living ring-opening metathesis polymerization. Prog Polym Sci. 2007;32:1–29. Grubbs RH, Tumas W. Polymer synthesis and organotransition metal chemistry. Science 1989;243:907–15. Rouhi AM. Olefin metathesis: big-deal reaction. Chem Eng News. 2002;80:29–33. Rouhi AM. Olefin metathesis: the early days. Chem Eng News. 2002;80:34–8. Nguyen ST, Johnson LK, Grubbs RH. Ring-opening metathesis polymerization (ROMP) of norbornene by a group VIII carbene complex in protic media. J Am Chem Soc. 1992;114:3974–5. Nguyen ST, Grubbs RH. Syntheses and activities of new single-component, ruthenium-based olefin metathesis catalysis. J Am Chem Soc. 1993;115:9858–9. Dias EL, Nguyen ST, Grubbs RH. Well-defined ruthenium olefin metathesis catalysts: mechanism and activity. J Am Chem Soc. 1997;119:3887–97. Grubbs RH. Olefin-metathesis catalysts for the preparation of molecules and materials. Angew Chem Int Ed. 2006;45:3760–5. Scholl M, Ding S, Choon WL, Grubbs RH. Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands. Org Lett. 1999;1:953–6. Jones AS, Rule JD, Moore JS, White SR, Sottos NR. Catalyst morphology and dissolution kinetics for self-healing polymers. Chem Mater. 2006;18:1312–7. Sanford MS, Love JA, Grubbs RH. A versatile precursor for the synthesis of new ruthenium olefin metathesis catalysts. Organometallics 2001;20:5314–8. Bolton SL, Williams JE, Sponsler MB. Stablilization of (Trialkylphosphine)ruthenium alkylidene metathesis catalysts using phosphine exchange. Organometallics 2007;26:2485–7. Ozawa T. A new method for analyzing thermogravimetric data. Bull Chem Soc Jpn. 1965;38:1881–6. Flynn JH, Wall LA. A quick, direct method for the determination of activation energy from thermogravimetric data. Polym Lett. 1966;4:323–8. Sanford MS, Love JA, Grubbs RH. Mechanism and activity of ruthenium olefin metathesis catalysis. J Am Chem Soc. 2001;123:6543–54. Hong SH, Day MW, Grubbs RH. Decomposition of a key intermediate in ruthenium-catalyzed olefin metathesis reactions. J Am Chem Soc. 2004;126:7414–5. Hong SH, Wenzel AG, Salguero TT, Day MW, Grubbs RH. Decomposition of ruthenium olefin metathesis catalysts. J Am Chem Soc. 2007;129:7961–8. Metton® and Telene® brochures. Brochures downloaded from http://www.metton.com and http://www.telene.com. Sanford MS, Ulman M, Grubbs RH. New insights into the mechanism of ruthenium-catalyzed olefin metathesis reactions. J Am Chem Soc. 2001;123:749–50. Bielawski CW, Grubbs RH. Highly efficient ring-opening metathesis polymerization (ROMP) using new ruthenium catalysts containing N-heterocyclic carbene ligands. Angew Chem Int Ed. 2000;39:2903–6. Kessler MR, White SR. Cure kinetics of the ring-opening metathesis polymerization of dicyclopentadiene. J Polym Sci Part A. 2002;40:2373–83. Choi T-L, Grubbs RH. Controlled living ring-opening-metathesis polymerization by a fast-initiating ruthenium catalyst. Angew Chem Int Ed. 2003;42:1743–6. Crabtree RH, editor. The organometallic chemistry of the transition metals. 4th ed. New York: John Wiley and Sons; 2005. p. 104–11.