The Effect of Various Additives on the Kinetic and Reaction Mechanism between Ethanol and Phenylisocyanate

High Performance Polymers

Volumn 19, Issue 5, 2007, Pages 520-530

  Coseri, Sergiu ^a  

^a PETRU PONI INSTITUTE OF MACROMOLECULAR CHEMISTRY   (Romania)

Author keywords

Alcohol association; Hydrogen bond; Phenylisocyanate; Reaction mechanism; Urethane formation

Indexed keywords

ADDITIVES; AROMATIC HYDROCARBONS; HYDROGEN BONDS; HYDROXYLATION; NUCLEOPHILES; OXYGEN; REACTION KINETICS;

HYDROXYL HYDROGEN; ISOCYANATE GROUP; PHENYLISOCYANATE; REVERSIBLE PROCESS; UNPOLAR MEDIA; URETHANE FORMATION;

ETHANOL;

EID: 34748911705     PISSN: 09540083     EISSN: 13616412     Source Type: Journal    
DOI: 10.1177/0954008306081194     Document Type: Article

References (20)

1. Kresta, J.E. and Hsieh, K.H. (1978). The Co-catalytic Effect of the Carbamate Groups in Cyclotrimerization of Isocyanates, Macromol. Chem., 179: 2779 - 2782.
2. Flynn, K.G. and Nenortas, D.R. (1963). Kinetics and Mechanism of the Reaction between Phenyl Isocyanate and Alcohols. Strong Base Catalysis and Deuterium Isotope Effects, J. Org. Chem., 28: 3527 - 3530.
3. Xu, L., Li, C. and Simon Ng, K.Y. (2000). In-Situ Monitoring of Urethane Formation by FTIR and Raman Spectoscopy, J. Phys. Chem. A, 104: 3952 - 3957.
4. Krol, P. and Gawdzik, A. (1995). Basic Kinetic Model for the Reaction Yielding Linear Polyurethanes. II, J. Appl. Polym. Sci. 58: 729 - 743.
5. Kogon, I.C. (1959). Near Infrared Studies. Rate Constants for the Alcohol/Aryl Isocyanate Reaction, J. Org. Chem., 24: 438 - 440.
6. Van derWeij, F.W. (1981). Kinetics and Mechanism of Urethane Formation Catalyzed by Organotin Compounds. I. The Reaction of Phenyl Iisocyanate with Methanol in Dibutyl Ether under the Action of Dibutyltin Diacetate, J. Polym. Sci., Polym. Chem. Ed., 19: 381 - 388.
7. Borkent, G. (1974). Advances in Urethane Science and Technology, Frisch, K.C. and Reegen, S.L. (eds), Technomic, Westport, CT, Vol. 3, p. 1.
8. Gambiroza-Jukic, M., Gomzi, Z. and Mencer, H.J. (1993). Kinetic Analysis of Bulk Polymerization of Diisocyanate and Polyol, J. Appl. Polym. Sci. 47: 513 - 519.
9. Dyer, E. and Pinkerton, R.B. (1965). Kinetics of the Tin-catalyzed Reactions of Phenyl Isocyanate with Ureas, J. Appl. Polym. Sci. 9: 1713 - 1729.
10. Duong, H.A., Cross, M.J. and Louie, J. (2004). N-Heterocyclic Carbenes as Highly Efficient Catalyst for the Cyclotrimerization of Isocyanates, Org. Lett., 25: 4679 - 4681.
11. Frisch, K.C., Reegen, S.L., Floutz, W.V. and Oliver J.P. (1967). Complex Formation between Catalysts, Alcohols, and Isocyanates in the Preparation of Urethanes, J. Polym. Sci. A-1, 5: 35 - 42.
12. Reegen, S.L. and Frisch, K.C. (1970). Isocyanate-catalyst and Hydroxyl-catalyst Complex Formation, J. Polym. Sci. A-1, 8: 2883 - 2891.
13. Kogon, I.C. (1959). Chemistry of Aryl Isocyanates: Rate and Equilibrium Constants for the Formation of Ethyl,-Diarylallophanate, J. Org. Chem., 24: 83 - 86.
14. Furukawa, M. and Yokoyama, T. (1979). A New Method for the Determination of Allophanate Concentration in Polyurethane Networks, J. Polym. Sci. Polym. Lett. Ed., 17: 175 - 180.
15. Sumi, M., Chokki, Y., Nakai, Y., Nakabayashi, M. and Kanzawa, T. (1964). Studies on the Structure of Polyurethane Elastomers. I. NMR Spectra of the Model Compounds and some Linear Polyurethanes, Makromol. Chem., 78: 146 - 156.
16. Okuto, H. (1966). Studies on the Structure of Polyurethane Elastomers. II. High Resolution NMR Spectroscopic Determination of Allophanate and Biuret Linkages in the Cured Polyurethane Elastomer: Degradation by Amine, Makromol. Chem., 98: 148 - 163.
17. Caraculacu, A.A. and Coseri, S. (2001). Isocyanates in Polyaddition Processes. Structure and Reaction Mechanism, Prog. Polym. Sci. 26: 799-851.
18. Caraculacu, A.A., Agherghinei, I., Baron, P. and Coseri, S. (1996). Hydrogen Bond Self-association and Chemical Reactivity. I. Kinetic Study of Reactions between Glycols and Phenylisocyanate, Rev. Roum. Chim., 41: 539 - 549.
19. Caraculacu, A.A., Agherghinei, I., Baron, P. and Timpu, D. (1996). Hydrogen Bond Self-association and Chemical Reactivity. II. Relations between Hydrogen Bond Association Degree and Isocyanate-alcohol Reaction Rate, Rev. Roum. Chim. 41: 725 - 731.
20. Caraculacu, A.A., Agherghinei, I., Prisacariu, C. and Cozan, V. (1990). Dibenzyl Structures in a Macromolecular Chain. III. Dibenzyldiisocyanates reactivity, J. Macromol. Sci. Chem., A27: 1547 - 1570.